
> See [2023 in review](https://youngkim.co/writing/2023-in-review) to see my goals/thoughts for last year.

## Some thoughts on 2024

### On Ramp



Career-wise, 2024 was largely defined by my promotion from staff engineer to director.

I've gone through a number of "career resets" in my life. Once from middle → high school, again from high school → college, and a final time from college → graduation. Each time, I found that credibility I had built up at the prior stage was forgotten, and I needed to prove myself anew to my peers. Upon graduation from college, I remember feeling tired since this was the third reset in 10 years, yet excited for the pressure of a new and final challenge. Whereas in school I only had four years to prove myself to my peers, after graduation I knew this would play out over the course of an entire career – easily 10+ years.

I mention the above to remark on how strange it is to hit this career milestone so early. I routinely ask my reports what their career goals over the next 3-5 years are, and occasionally they ask me the same. I always try to answer truthfully – but as of late the genuine answer has been that "I'm not sure". It's a relief to not navigate more awkward career conversations with my own managers and anxiously await performance cycle results, but there's a lingering question of "is this it?" in my own mind. I believe an easy measure of career-based success is the title/company on your LinkedIn (at least that's how I judge my peers), but realistically I've reached a summit for the foreseeable future.

As mentioned in [last year's review](https://youngkim.co/writing/2023-in-review), to close 2023 I was the Tech Lead Manager of both Procurement and Bill Pay, managing a total of seven people. Procurement was still a month away from its [public launch](https://ramp.com/blog/ramp-procurement), and Bill Pay was drowning in customer escalations and bandwidth constrained by recent turnover. Much has changed over the last year – Bill Pay has stabilized and its TPV (total payment volume) has grown 4x YoY, Procurement has grown to a sizeable customer base, and we've spun up a third team for Vendor Management. I manage a team of fourteen engineers now, and expect that it'll grow to twenty by the end of next year.

Looking back, it's been a remarkable year. I'm still coming to terms with the knowledge that decisions I make can cause a meaningful delta in Ramp's potential outcome, and I've seen this play out over the last year. From recommendations for team leadership, performance related feedback (both positive and negative), and architectural design decisions, I feel a burden to make correct decisions over and over again. In hindsight, it becomes apparent what the right choice was, but in the moment it's incredibly ambiguous. This pressure is also isolating – no one has the full context that I possess, and although I can seek advice, ultimately the decisions are mine to own.

I'm grateful to Max, Nik, and Karim (my own management chain) for trusting and believing in me, and I'm especially thankful to all the teams I work with. I recently wrote some of my [management learnings and takeaways here](https://www.youngkim.co/writing/musings-as-a-manager), but I still have a long way to go to become the manager I always I wanted to have – so thank you to everyone I work with for bearing with me. I'd like to close on [a note](https://morepablo.com/2016/08/six-months-of-managing.html) that Pablo, my first manager at Ramp, wrote in a section titled "Remember who does the work".

> The fact is, many of the people working for you are spending most of their waking hours in their one life making people up the chain disproportionately wealthy, often doing a high-skill thing they themselves couldn't do (very obvious in the case of tech workers). Apparently it's a thing to not know anything about a craft (e.g. computers), bark at people who've dedicated years of study, crack a whip behind them demanding underspecified output (remember: you don't know their problem domain like they do), then feeling entitled to orders of magnitude from the wealth that work creates. I… just can't understand that mentality. You're managing people. They trust you. Keep them safe, guide them to fulfilling work, try to make them happy. What's the point of having any power in a structure if you're not going to make it great for the people most impacted by your actions?

### On reading

After reading 52 books in both 2020 & 2021, I had a bit of reading burnout (unsurprising, I know) that lasted from 2022-2023. I've primarily read non-fiction after college, picking up the occasional fiction book as a palette cleanser.

I started out 2024 binge-reading books by Brandon Sanderson, who is on pace to be one of the most prolific fantasy authors of all time. I decided afterwards that this would be a year of reading primarily fantasy, a genre that I loved growing up, but one that I had tabled in favor of more "grown-up" non-fiction books. And what a year it's been! I've been reinvigorated by reading once more, reading 45 books for the year.

I'm excited to bring back a tradition of announcing my top reads for the year, which I skipped last year:

- [The Will of the Many | Hierarchy #1](https://www.goodreads.com/book/show/58416952-the-will-of-the-many)
  - The best book I read this year. Fantasy can be a chore to read, with endless chapters devoted to world-building and giving the reader context to understand what's happening. This book defies those stereotypes with relentless pacing from the first chapter, an intuitive yet layered power system, and twists and turns that keep readers on their toes throughout.
- [Jade Legacy | Jade War #3](https://www.goodreads.com/book/show/51057191-jade-legacy)
  - A thrilling conclusion to a remarkable series. A satisfying ending is the most difficult feat for an author to pull off, yet Fonda Lee takes the myriad threads building throughout the series and nicely ties them together.
- [The Way of Kings | Stormlight Archive #1](https://www.goodreads.com/book/show/7235533-the-way-of-kings)
  - Journey before destination. The first book of Brandon Sanderson's magnum opus series, the Stormlight Archive. I love the way character development is woven into the power system itself, and I found the writing deeply meaningful.
- [Babel](https://www.goodreads.com/book/show/57945316-babel)
  - The only standalone book on this list, Babel features a brilliant magic system – power is derived from the meaning lost in translation between two languages. Despite having weaker character work than the rest of the books featured, Babel leverages its terrific premise to explore nuanced topics like colonialism.

Honorable mention:

- [Mistborn | Mistborn #1](https://www.goodreads.com/book/show/68428.Mistborn)
  - Another book by Sanderson, Mistborn is narratively simpler than other books on this list, but has great character work and compelling narrative points underpinning it.

As always, I track all recommendations [here](https://www.youngkim.co/books), with proper ratings on my Goodreads.

## 2024 Goals: A Review

**✅ Have better work + life balance.**

I certainly have better work-life balance than I did while working on Venue, but I don't know that it's "good" in the traditional sense. My manager, Max, has an intuitive framework for thinking about burnout – everything you do at work is either energizing or takes away energy. As long as the total energy from a work day nets out to positive, you won't burn out.

There's still plenty of days where I feel stretched, given the sheer number of meetings I'm in. According to Google Calendar, I average ~2.6 hours of meetings daily, and they're largely clustered in back-to-backs on Tuesdays/Thursdays. Fortunately, meetings are less draining than I originally expected, and I've built up stamina over time to survive these. I haven't done serious IC work in nearly a year, and although I spend ~10% of my week coding, it's spent on small side quests that help me stay in touch with the codebase.

After typical work hours, I'm online most days in case anything explodes or if I get an urgent ping. Bill Pay's product revolves around money movement, and the thought of a potential unbounded loss to Ramp's business causes me some existential dread. Outside of incidents, since nearly all the value I bring is in meetings, it's hard for me to do productive work outside of business hours, which works to my benefit since I can be a workaholic.

**✅ Become a better manager.**

I've gone into plenty of detail above, so I'll refrain from expanding further here. I believe managing is largely experiential, and there isn't any substitute for going through situations first-hand.

## 2025 Goals

**Try therapy**

Over the last ten years, I've grown somewhat detached from my daily life. I have emotions like everyone else, but the degree to which I feel any emotion is noticeably less than when I was younger. It's as if I live in an emotional fog, and anything I experience is blunted. To be clear, I don't think I'm depressed – I consider myself happier than most of my peers, and I do feel happy and grateful nearly everyday.

My belief is that this stems from the realization that most things in life are mediocre. I remember being awed by the first expensive restaurant I visited, but at this point I've been to too many to count, and that initial wonder is gone. I feel the same way about books, music, movies, products, video games, technology, and nearly everything else – greatness is rare. I'm continuously disappointed by the low standards others have (yes, I'm judging your Beli scores), and over time I've come to take recommendations from others with a grain of salt.

The last time I felt truly alive was when I went on the [Angel's Landing hike](https://youtu.be/jy6K0KoMrco?si=psMAk36HI7gbH6dM&t=41) in 2022 – a hike where on average, someone dies every year (watch the video and it'll be obvious how). Being so close to my own mortality on the hike cleared the emotional fog for weeks, but over time that fog returned, and it's been here since.

Rather than continue to psycho-analyze myself, I want to try therapy. Many of my friends and peers have spoken highly of their experience, and I think it'll be a good learning experience regardless of any result. Expect a writeup on this next year!

**Exercise regularly**

Since running a [half marathon](https://www.youngkim.co/writing/half-marathon) in 2022, I haven't exercised regularly since. I'll leave the exact details of "regularly" off this site, but I plan to hold myself to this goal this year.




2024 in review


> See [2022 in review](https://youngkim.co/writing/2022-in-review) to see my goals/thoughts for last year.

## 2023 Goals: A Review

**Find clarity on what to work on.**

Kevin, TK, and I started Venue in September of 2022. When I was writing my annual reflections and contemplating goals for 2023, Venue was unsurprisingly top-of-mind.

At the time, we had finished the inaugural Sequoia Arc Americas program and pivoted through a number of problem spaces, but still searching for the one we would commit to. Last year, I wrote:

> Starting a company, especially VC-backed, is unfortunately rooted in realism. For any dream we might desire to pursue, there's an omnipresent reminder that it needs to be a viable business. We're looking for something at the intersection of idealism and reality (sorry, I know this is corny) – but we'll see how it goes.

Shortly after the time of writing, we committed to procurement as the problem space we were willing to invest in. For a number of different reasons, I'll refrain from publicly sharing more details, but we were acquired by Ramp to build out the procurement product in September.

**✅ Wake up earlier (concretely, at or before 8:30AM).**

I've been consistently waking up earlier, typically between 7:30AM – 8AM. On the weekends, I typically sleep in until 9AM.

**❌ A few personal goals...**

I accomplished two of my personal goals, and failed the last one by a long shot.

**✅ Manage my time better.**

In 2022, I wasn't thrilled with how I spent my time, namely by spending way more time watching YouTube than I would've liked.

## Some thoughts on 2023

### Venue → Ramp

2023 was largely defined by the trials and tribulations we went through for Venue. Working on a startup was far more stressful than I had anticipated – I remember feeling naseous on "Day 1" knowing that there wasn't any safety net to fall back upon. If we failed (as most companies do), we'd need to accept that _we_ were directly responsible  and cope with bruised egos.

With any other job, it's easier to decouple yourself from where you work, but with a start-up every criticism feels personal. When I was at Facebook, it was easy to disassociate and distance myself from the company as a whole, but with Venue, I found people were engrossed with the idea of being a founder.

We received some press in January for the acquisition and the launch of Ramp Procurement ([Fortune](https://fortune.com/2024/01/30/young-entrepreneur-sequoia-thrive-capital-ramp-sale/), [Techcrunch](https://techcrunch.com/2024/01/30/fintech-ramp-acquires-another-ai-powered-startup/amp/), [Ramp blog post](https://ramp.com/blog/ramp-procurement)), and I'm genuinely happy to be back at Ramp. I was a full-time IC for two months before transitioning fully into people management, and at the moment I have seven direct reports. The role change was unexpected yet necessary given some turnover & performance-related changes, but it's been a massive opportunity for me to grow. I'm excited to make the most of this through 2024 and help accelerate Ramp's growth.

## 2024 Goals

**Have better work + life balance.**

I tend to obsess about work. I'd like to dedicate more focus time for non-work: this includes taking PTO, disconnecting properly on the weekends, limiting the number of hours I spend after dinner, and spending more time connecting with friends + family.

**Become a better manager.**

I'm lucky to have a significant responsibility and trust at Ramp. I currently manage a team of seven people, and I'd like to become the manager I wish I had earlier in my career.

There's specific areas I want to focus on:

- Being more honest around areas for improvements, and when performance is lacking.
- Explicitly calling out what's going well.
- Collaborating better cross-functionally with others in the org chart.

**A few personal goals...**





2023 in review


> See [2021 in review](https://youngkim.co/writing/2021-in-review) to see my goals/thoughts for last year.

## 2022 Goals: A Review

**✅ Run a half-marathon.**

I'm proud that I was able to do this, given that I was not in good shape heading into last January. I've documented the journey fairly extensively [here](https://www.youngkim.co/writing/half-marathon).

I'm disappointed that I didn't continue running regularly afterwards, but alas, life had other plans for me. Hopefully I'll be able to squeeze more runs in this year!

**❌ Write + publish at least once a month.**

Unsurprisingly, I failed to hit this goal (for the second year in a row). I published 7 times this year which is the furthest that I've made it, but I won't be renewing this challenge for 2023. I want to continue writing and documenting my thoughts in public, but I don't think setting a numeric goal is the right way to encourage this.

**✅ Read 25 books this year.**

I barely made it to the finish line this year. I had some favorites, though:

- [A Little Life](https://www.goodreads.com/en/book/show/22822858)
  - Brutal and heartbreaking, this book is the among the best fiction I've read in my life. Not for the faint of heart.
- [Our Missing Hearts](https://www.goodreads.com/book/show/60149573-our-missing-hearts)
  - Celeste Ng is a remarkable writer – I loved this book because the themes hit home for me. It's an opinionated commentary on the state of the world and the characters shine throughout.
- [The Upside of Stress](https://www.goodreads.com/book/show/23281639-the-upside-of-stress)
  - This reads like a classic self-help book (not in a good way – self help books suffer from being long & didactic), but I found the underlying message compelling. Stress is often unavoidable, but your attitude toward it can make all the difference.

**✅ A Few Personal Goals...**





I had three personal goals (sorry friends, these are for my eyes only). I made serious progress on goal one and three, and generally hit goal two, so I'm going to chalk all three of these as successes.

## Some Thoughts on 2022

All things considered, 2022 was one of the most eventful years of my life. I've documented certain parts earlier ([here](https://www.youngkim.co/writing/on-leaving-ramp), [there](https://youngkim.co/writing/starting-something-new), and others), but here's a quick TLDR of notable events:

- Ran a half-marathon
- Shipped Ramp Flex as one of three founding engineers (see [launch post](https://ramp.com/blog/announcing-ramp-flex))
- Left Ramp (additionally shipped the most code at Ramp during my tenure, which I'm proud of)
- Participated in the inaugural [Sequoia Arc](https://arc.sequoiacap.com) program

Despite all of the chaos and the uncertainty that starting a company brings, I'm proud of how the year went.

In 2020, as my #1 goal, I wrote:

> Find clarity on what I want to work on in 2022. I know this is vague, but I want to take the time to find conviction in where my career is heading.

In 2021, I wrote:

> I felt disillusioned working at Facebook. It was hard for me to believe that my work made a positive impact on society or that working at Facebook was the best use of my talent. The compensation, perks, and brilliant coworkers all sugarcoated the truth that no one at Facebook fully believed that they were achieving the vision of "making the world more open and connected". Overall, my time at Facebook reminds me of [an essay I wrote](https://youngkim.co/writing/the-crowd) while still in college.
>
> I switched companies and joined [Ramp](https://ramp.com/) in October, and it's been an amazing two months so far. The engineering talent is phenomenal, and being part of this all-star team reminds me of my time on [Cornell AppDev](https://www.cornellappdev.com/). I remember people on AppDev always lamented "I wish we could just start an AppDev company after graduation instead of joining [Company]", but Ramp has come pretty close (and in some ways surpassed!) my vision of what that might look like.

In 2022, I think I've taken this philosophy to the logical extreme, in a way that my younger selves would be happy with. No matter the outcome the company has, I'd like to put on the record that I have no regrets about venturing down this path.

## 2023 Goals

1. Find clarity on what to work on. \
  Funnily enough, this is a callback to my 2020 goal. There's some irony in the fact that after you make the difficult decision of pursuing your own dreams, you then have to make the more difficult decision of _which_ dream is worth pursuing. \
  \
  Starting a company, especially VC-backed, is unfortunately rooted in realism. For any dream we might desire to pursue, there's an omnipresent reminder that it needs to be a viable business. We're looking for something at the intersection of idealism and reality (sorry, I know this is corny) – but we'll see how it goes.

2. Wake up earlier (concretely, at or before 8:30AM). \
  The first essay I ever published was about [the importance of sleep](https://www.youngkim.co/writing/sleep), so this is another goal rooted in the past. I've been sleeping around 9-9.5 hours over the last year, and I don't think this is because I need to sleep so much, but more so because it's just become a habit. I think sleeping less shouldn't affect my health, but will buy me more time in the day.

3. Manage my time better. \
  This goal isn't as measurable, but I want to be better about where I spend my time. Once work picks up I'll be much more busy with work-related tasks, but I want to be more intentional about what I get done on a day-to-day basis.

4. A few personal goals. A bit like last year, we'll see if/when I choose to reveal these – but fingers crossed, these will go as well as they went in 2022!






2022 in review


> See [2020 in review](https://youngkim.co/writing/2020-in-review) to see my goals/thoughts for last year.

## 2021 Goals: A Review

**✅ Find clarity on what I want to work on in 2022. I know this is vague, but I want to take the time to find conviction in where my career is heading.**

This was my main priority heading into 2021. In last year's goals, I refrained from elaborating on this as I was still employed at Facebook, but I'd like to explain this a bit further now.

I felt disillusioned working at Facebook. It was hard for me to believe that my work made a positive impact on society or that working at Facebook was the best use of my talent. The compensation, perks, and brilliant coworkers all sugarcoated the truth that no one at Facebook fully believed that they were achieving the vision of "making the world more open and connected". Overall, my time at Facebook reminds me of [an essay I wrote](https://youngkim.co/writing/the-crowd) while still in college.

I switched companies and joined [Ramp](https://ramp.com/) in October, and it's been an amazing two months so far. The engineering talent is phenomenal, and being part of this all-star team reminds me of my time on [Cornell AppDev](https://www.cornellappdev.com/). I remember people on AppDev always lamented "I wish we could just start an AppDev company after graduation instead of joining [Company]", but Ramp has come pretty close (and in some ways surpassed!) my vision of what that might look like.

Overall, I'm proud that I was able to navigate these murky waters and achieve this goal. Major thanks to [TK Kong](https://tkkong.com/) who sold me on Ramp, Kevin/Omar who listened to my never-ending thoughts on FB, and everyone else who supported me through this decision.

**✅ Read 52 books this year.**

For the second year in a row, I've read 52 books! I feel very fortunate to have enjoyed so many reads this year; here were some of my favorites:

- [Foundation Trilogy](https://www.goodreads.com/book/show/46654.The_Foundation_Trilogy)
  - A masterclass in science fiction. The plot twists throughout are incredible; it's one of those series where I wish I could forget the plot so that I could experience it again.
- [All the Light We Cannot See](https://www.goodreads.com/book/show/18143977-all-the-light-we-cannot-see)
  - I loved reading this – the writing is somehow both incredibly poignant yet unsentimental. I typically don't enjoy books with dual perspectives, but this book executed the concept perfectly.
- [Homeland Elegies](https://www.goodreads.com/book/show/50358133-homeland-elegies)
  - I thought this was a perfect book for the current political climate and state of the country. Each chapter felt carefully constructed, melding truth and fiction to create incredibly thought-provoking situations.

As usual, I've noted all my recommendations for this year [here](https://youngkim.co/books).

**❌ Write + publish at least once a month.**

I unfortunately only published a total of six times last year. My excuse is that this was my stretch goal, but the truthful answer is that I simply didn't make enough time for this.

## Some Noteworthy Events

- As mentioned above, my major life update is switching jobs and joining Ramp. It's only been two months since I've joined, so I'm sure I'll have much more to discuss next year!
- I worked on [Crypto Wrapped](https://twitter.com/CryptoWrapped/status/1475971984383168514)! It's a miracle that this went from ideation to launch in a few weeks, as we severely underestimated how difficult getting everything production-ready would be. Regardless, it was incredibly exciting to ship something in ✨web3✨ and see it be well-received.
- This site is now hosted on [Netlify](https://youngkim.co) and off Squarespace! I've honestly meant to do this for years but never had the discipline to go through with it. The most important part of this change (for me) is that I can now write posts in markdown! Squarespace's web editor was incredibly unoptimized and did not auto-save changes, leading to frustrating situations where my browser tab would freeze and I'd lose all my drafted changes.
- After over 190 hours of playing Smash Ultimate, I've finally reached Elite Smash! Yes, this is noteworthy enough to mention here 🤣

## Some Thoughts on 2021

This year flew by. I'm not sure if my memory is deterioriating or if this is because of COVID-19, but in my mind 2020 + 2021 have combined into a single year. Some days I wake up convinced I'm still 22; other days I wake up thinking I'm already 24; usually sometime throughout the day I remember that I only turned 23 a month ago. I'm curious if other recent new-grads are feeling this way, or if it's just me.

The fact that this year has flown by has reinforced how important focus is. The unfortunate truth is that I only have 7 more years' worth of goals left to write before I turn 30. Even worse, I only get one chance to choose the correct goals. To be fair, this knowledge might be more of a blessing than a curse - as Socrates said, "The unexamined life is not worth living".

## 2022 Goals

1. Run a half-marathon.\
   \
   Running a half-marathon has always been on my life bucket list, and something I want to achieve sooner than later (I realized that I'll be approaching my athletic peak in a few years). I've already started training for this – I'm using Nike Run Club to track my progress, and I'll be sure to write a reflection on the training process. If everything as planned, I'll accomplish this halfway through 2021!

2. Write + publish at least once a month.\
   \
   How hard can this be? I'm already starting the year publishing this, so just 11 more posts to go 😉. Jokes aside, my motivations for this goal are the same as last year – I simply have so much I want to write about.

3. Read 25 books this year.\
   \
   Although I was able to achieve my goal of reading 52 books two years in a row, I feel a bit burnt out from reading. I started the year with momentum – comfortably ahead of the one book a week pace, but as the year went on reading felt more like a chore and not something I genuinely wanted to do.\
   \
   Nevertheless, I want to continue reading and crossing books off my bucket list. I've found that books have been far more impressionable on me than anything I've watched. I think setting a more reasonable goal will prevent any burnout, and will incentivize me to take on more challenging reads.

4. A few personal goals – if they go well, I'll discuss these next year!






2021 in review


## Reading

My only goal for 2020 was to read 52 books for the year. This was my second year chasing after this milestone – and I’m proud to say that I read 53 books in 2020!

I originally set this as my goal for 2019, when I realized I had an ever-increasing list of books I wanted to read, while reading less books each year than ever before. I set the audacious goal of reading 52 books in 2019 (not even reaching 40), but I think the habits I created were instrumental to creating a rhythm in 2020.

I’ve touched on some of my [motivations for reading here](https://youngkim.co/writing/reading), which largely haven’t changed. I still stand by the Kindle, and halfway through the year I started writing more extensive reviews on Goodreads.

I’d like to share some of my favorite reads of 2020 (in no particular order):

- [Good Economics for Hard Times](https://www.goodreads.com/book/show/51014619-good-economics-for-hard-times)
  - A must-read from the authors of the 2019 Nobel Prize in Economics.
- [The Defining Decade: Why Your Twenties Matter](https://www.goodreads.com/book/show/40603783-the-defining-decade)
  - I felt this was particularly apt for me as a 21-year-old; practical and helpful.
- [Minor Feelings: An Asian American Reckoning](https://www.goodreads.com/book/show/52845775-minor-feelings)
  - A beautiful and raw set of essays describing what it means to grow up an Asian in America.

## Life Updates

- I graduated from Cornell University earlier this year, with both a M. Eng and B.S. in Computer Science in four years.\
   \
   I was able to do this through the Early M. Eng program, which allows students to start their M. Eng in the final semester of their Bachelor’s. I plan on writing about the pros/cons this year, but the TLDR is that it’s not worth it – and I certainly wouldn’t have done it if it meant staying another semester.

- I started at Facebook on June 8th, joining the Resource Delivery team, which handles static resource delivery (HTML/CSS/JS) for clients on the web.\
   \
   I originally planned on traveling after the school year and starting at Facebook in August, but changed my start date in early March. Cornell had just declared classes would be remote for the remainder of the semester, and it was clear that there was no chance it would be safe to travel in June-August. Luckily, my timing worked out – a week later, recruiters froze start dates for any new hires.\
   \
   I’d like to write about both my internship experience + my recruiting experience, so when I get to that I’ll link to them here.

## Minor Life Updates

- Worked on Hub with the incredible team of TK, Kevin, and Omar for a CalHacks hackathon, winning prizes from Unusual Ventures and Village Global. [Check out TK’s fantastic write-up on this](https://tkkong.com/work/hub).
- Made some everyday-usage upgrades:
  - Dell 4K Monitor. I went with the one suggested by [Wirecutter](https://www.nytimes.com/wirecutter/reviews/best-4k-monitors/) (Dell Ultrasharp) and I’ve loved it since.
  - Herman Miller Aeron. Is it worth the price? The cliche advice is to invest the most in what you use everyday. All I know is that my back used to hurt sometimes after sitting the whole day, and now it doesn’t.
  - [Autonomous Desk](https://www.autonomous.ai/standing-desks/smartdesk-2-home). I left this in my cart for a day, and they sent me a discount code. I hardly ever use the “standing” feature, but assembly was straightforward and the desk room is great.
  - Converted this website to a dark color scheme. I’ve felt my eyes straining more and more as the year has progressed, and getting [DarkReader](https://darkreader.org/) and investing in simple solutions like lowering monitor brightness have paid dividends.

## 2021 Goals

1. Find clarity on what I want to work on in 2022. I know this is vague, but I want to take the time to find conviction in where my career is heading.
2. Read 52 books this year.
3. Write + publish at least once a month.\
   \
   This is something I’ve wanted to do since I started this website, and reading so much has made me appreciate good writing even more. Like my ever-increasing list of books I wanted to read in 2021, I’ve accumulated an endless list of subjects I want to touch on.\
   \
   There’s plenty of articles on Hacker News about why writing is so important (check out [this](http://www.paulgraham.com/writing44.html) or [that](http://paulgraham.com/useful.html) from Paul Graham), and improving as a writer & taking the time to formulate thoughts into writing are areas I want to improve on.\
   \
   I don’t think sharing writing is as crucial as _simply writing more_, and I’ve always felt that I’ve written for myself.


2020 in review


> "Knowledge is the mother of fools", he said.
> "Remember, the greatest part of wisdom is in recognizing your own ignorance."
> 
> -*Empire of Silence, Christopher Ruocchio*

I've observed a pattern of behavior at work recently, aptly summarized by the quote above: the more senior someone gets, the more likely they conflate knowing more with being less ignorant. 

It's easy to see how someone takes on this mindset. They've been rewarded for their knowledge with promotions and more responsibility. These people _are_ right most of the time, and often times they've been proven correct on some contrarian opinions. This can result in them becoming increasingly stubborn – why should they back down if this is another instance where everyone else is wrong?

### Navigating disagreements as a peer

When you inevitably get into disagreements with people like this, there's generally two paths forward. You can cooperate to avoid conflict (majority case) or escalate (should be used sparingly). We'll also assume that you've spent sufficient time with them directly to convince them otherwise, but they're unwilling to budget for the reasons above.

In my experience, this trend only manifests for tenured folks, as newer team members are more open to feedback from peers/managers. Given they're tenured, you should find others in an organization who've had to navigate similar situations. If no one else has had this problem, that's a red flag – the problem either lies with you, or you lack a network of peers willing to tell you the truth.

Next, be strategic about which battles you choose to fight. It should be high-priority to the business and important that that it's resolved now. If it's minor, I'd suggest sharing the feedback (could be directly, with their manager, your manager) and moving on.

Finally, assuming that you've gone through the steps above, get counsel from others who've had similar experiences. You should understand what approaches have worked and which ones haven't, and come up with a strategy that fits your situation. Depending on how senior the person is, you may also need leadership buy-in.

### Navigating reports as a manager

The best way to deal with these situations as a manager is to avoid hiring people like this in the first place, but interviews are lossy, and it can be difficult to gauge this in advance.

Warning signs that someone falls into this category: 
- Causing unnecessary interpersonal conflict justified because "they were right".
- Making incorrect assumptions because they can't recognize their blind spots (unable to recognize ignorance).

Navigating these situations can be difficult, because these folks are typically both senior + tenured. As a result, they do great work most of the time, and losing them may be leave a short-term hole for the team & company. However, if reports are not coached out of this pattern of behavior, they typically continue down this path and their behavior continues to worsen.

First, recognize that this behavior is a serious issue, and needs to change. You should document evidence from peers & cross-functional partners, and also recognize that because they may be the most senior person on the team, feedback may be less obvious. Often times though, you'll get warning signs in 1:1s and by observing their behavior yourself.

Next, once there's sufficient evidence, this feedback should be communicated directly to the person, with the caveat that this needs to improve. Behavioral issues like these can exist outside the scope of a leveling guide, but regardless there should be organizational alignment on productive ways to disagree. 

Bringing up this subject can be a sore spot for those exhibiting this behavior, and as a result, you should come to terms with the possibility that they may leave. However, ignoring these signs as a manager can lead to far worse outcomes long-term, and it's best to address any constructive feedback as soon as possible – this is no exception. Ultimately, if it doesn't improve, you may need to part ways, which can be an unpopular decision (as mentioned, they're productive team members most of the time).

### Closing thoughts

As I've progressed in my own career, the mistakes I've made have larger consequences, and I've been painfully humbled by each one. Paradoxically, the more I learn, the more I realize the breadth and depth of my ignorance. I've heard cliches about "the beginner's mindset" for most of my career, but it's only recently that I've appreciated the wisdom in the saying.

Knowledge and ignorance


In ["The Real Competition is the Water"](https://www.rkg.blog/water.php), Ravi Gupta wrote:

> James Astill wrote a [piece](https://www.economist.com/1843/2016/10/24/american-children-are-drowning-in-self-esteem) that I think about all the time. In the article, he wonders why American children are so good at swimming and so bad at math. He comes to the conclusion that schools are too busy teaching kids to feel good about their math performance rather than actually teaching them how to do math. At the same time, he notices that his children’s swim instructors are similarly supportive to the math teachers, but with completely different results. He observes that the swim instructors have an advantage over the math teachers. They have been blessed with an unforgiving standard: the water. Here’s the closing sentence from his piece: “If their instructors had focused on making them feel good about swimming, instead of on making them swim, they could have drowned.”

As a manager, I've realized cultivating career growth is the job of a lifeguard. Reports will often struggle in the middle of the pool – your job as a manager is to determine whether they're drowning or they want to be rescued because swimming is hard. Helping reports too often will stunt their ability to get better at swimming (career growth, promotions), although not recognizing that reports are drowning can be worse (low morale, burnout).

I've observed attentive managers are good at detecting drowning, but less good at determining when they should let their reports struggle. Although solving your reports' problems may keep them happy in the short-term, it'll prevent them from building long-term resilience by figuring it out themselves. This cycle also leads to more work for managers – reports will continue asking for help in situations when they don't fully need it.

Letting reports struggle doesn't mean reports feel unsupported. Managers should be lifeguards: providing encouragement on the sidelines, and ready to intervene if their reports start to drown.


Managers as lifeguards


There's an unbelievable amount of advice and content online on finding the right startup idea. Unfortunately, I thought most of it was too noisy. We've been going through the ideation maze for a bit over a month, and here's some learnings, advice, frameworks, and resources on finding and validating the right idea.

# Finding Ideas

## Be comfortable with being uncomfortable

A close friend in college had the mantra of "seek discomfort". It may be depressing to be stuck in the ideation maze, but it's infinitely better than dedicating time to the wrong idea.

## Fragmented, Low NPS Market

Keith Rabois (from Founders Fund) has a [legendary tweet](https://twitter.com/rabois/status/870673635375104000):

> Formula for startup success: Find large highly fragmented industry w low NPS; vertically integrate a solution to simplify value product.

I like this quote because of its simplicity. In established markets, this is a good strategy, but it doesn't apply as nicely to emerging markets.

## Insider vs. Outsider

Stephen Ango wrote a very insightful [article on this topic that I recommend](https://stephanango.com/solving-problem-finding), but I'd like to highlight a specific portion:

> Common wisdom encourages us to solve the problems we see in our immediate surroundings — in writing it’s distilled as “write what you know”, but it can be generalized as “do what you know”.
>
> Without deep experience in a specific field, this approach rarely yields good problems to solve, usually for one or both of these reasons:
>
> (1) The problem is very personal, it doesn’t help very many people (2) The gains to be made are small
>
> ...
>
> Every complex system has problems. Most industries are complex and ripe for problem-finding. The challenge is knowing enough about the domain, yet retaining the beginner’s mind necessary to actually see the problem.

Simply, you're an insider if you're building in an area of deep expertise, and an outsider otherwise.

There's examples of both types of founders, but my general recommendation is to spend more time thinking about areas where you're an outsider.

Most great founding teams are highly technical and capable of building the product themselves. Because of that, the first idea they think of is an improvement on a product that they themselves have used. There's category-defining companies that have come out of this approach (Notion, Linear) but my opinion is that these markets are significantly more saturated, and the potential differentiators are far more limited.

## Framework

Here's the steps you should work through, in order, when finding an idea:

1. Customers
2. Problems
3. Solution

There's a really great resource written by Erik, co-founder of Vanta, that I'd be happy to share over e-mail, but I'd like to quote him here:

> When you skip steps, you bundle multiple assumptions together — you’re validating a problem, solution, and implementation all at once. If the probability of being right about one of those is 1% and you guess a problem, solution, and implementation — what’s the probability that you’re right about all three simultaneously?
>
> Yeah, it’s 1%^3, or a one-in-a-million chance of success. If you take those problems in sequence, you can attempt each stage 100 times to expect success once for a total of 300 total attempts. That’s not only better, it’s the difference between a chance of success and deterministically setting yourself up to fail.

It may seem obvious, but the solution should never precede the problem. It's an easy trap to fall into, especially when you're constantly looking at other successful companies for inspiration.

We did this often, when we would think about "What about this AI product" or "Toast for Y vertical" and realize in customer interviews that their problems were totally different than the hypothetical ones we had imagined.

# Validating Ideas

## Can you work on this for 5-10 years?

In general, I don't think founders are fully honest with themselves when answering this question (us included, at first).

If your startup does well, you'll be working on this idea for the next 5-10 years of your life (at least). Even if the idea is something you'd be able to sell customers, talent, and investors on, at the end of the day you're the one who has to believe in the idea more than anyone else.

## Wave Hunting and Why Now

Ayo of kunle.app has written a [fantastic article on this topic](https://kunle.app/june-2020-wave-hunting.html):

> If you’re optimizing for impact, choosing a material problem matters far more than your personal effort and your ability to execute.
>
> ...
>
> This resonated as I thought of what didn’t work at my last startup and where we could have done better. We spent 4 years building an incredible amount of things and doing a (in my opinion) better than average job of micro-optimizations to make the product and business work. We read all the things, worked all the hours, spent all our savings and it still didn’t matter.
>
> I think our biggest headwind was working on something that didn’t matter, in a domain that wasn’t growing in any macro sense.

Many investors will emphasize that there should be a "why now" for what you're building, but I prefer the "wave hunting" analogy.

First, is your TAM large enough? If it isn't, is it growing exponentially? If the answer is "no" to both of those questions, the hard truth is that you should find a different idea.

You want to have the strongest possible tailwinds possible when you're picking an idea. Since most startups fail, your job is maximizing your chance of success over all else. For some ideas, the "why now" won't be apparent until much later, but in general, I believe that all successful companies realize their "why now / wave" at some point.

## Storytelling and Founder-Market Fit

My (perhaps contrarian) opinion is that story is the single greatest factor that determines whether a startup succeeds or fails. The story you tell is how you get investments, it's how you close candidates, and how you convince customers to use your solution over everything else in the market.

Most of the company story is built up over time, but having a strong founder-market story can exponentially increase your chance of success. (Startup success, like many things in life, is compounding – having a stronger story to start will itself compound over time).

## What is the scale of your ambition? Or, is your idea actually insane?

There's a quote from the Arc program that really stuck with me:

> As a founder, it's equally as difficult to make a restaurant successful as it is to make the next Tesla successful. The main difference is that no talented person wants to work at a restaurant.

What I took away from this is that it's harder to get funding, harder to attract talent, and strangely harder to succeed the less ambitious your idea is.

If the odds are already so stacked against you, and success is so improbable, why not shoot for the moon?

# Other Helpful Resources

- [Unusual Ventures Field Guide](https://www.field-guide.unusual.vc/chapters-enterprise/start-your-company)
- [Sam Altman Playbook](https://playbook.samaltman.com)
- [Michael Seibel: Should You Follow Your Passion?](https://www.youtube.com/watch?v=KWNNmPCF-Xs)
- [Michael Seibel: Why Should I Start a Startup?](https://www.youtube.com/watch?v=qh8sHetf-Nk&t=586s)


Finding and validating startup ideas


I don't think people ask enough stupid questions, where a stupid question is one that challenges a core underlying assumption in the situation. For example, if people were arguing over how to put a fire out, one stupid question would be "why do we need to put the fire out in the first place?". This question might seem fairly stupid, but note that in the case of controlled forest fires, someone had to ask this before we began _intentionally_ starting forest fires.

From what I've seen at work, people seem hesitant to ask stupid questions because they are afraid of being perceived as stupid by others. Ironically, I've observed that those seen as the smartest by others are in fact the ones who ask the highest frequency of stupid questions. Questions like "why are we doing this in the first place?" or "can you explain why we're doing X instead of Y?"

Taking this even further, I've found that there's value in asking stupid questions in my own life. Simple questions like "why am I doing X everyday?" or "why do I even work at this job?" can act as a forcing function to revisit core assumptions about what makes us happy (or unhappy) in our daily lives.

There's a pertinent fable on this topic:

> An American investment banker was at the pier of a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellowfin tuna. The American complimented the fisherman on the quality of his fish and asked how long it took to catch them.
>
> The fisherman replied, “only a little while.”
>
> The American then asked why didn’t he stay out longer and catch more fish?
>
> The fisherman said he had enough to support his family’s immediate needs.
>
> The American then asked, “but what do you do with the rest of your time?”
>
> The fisherman said, “I sleep late, fish a little, play with my children, take siestas with my wife, Maria, and stroll into the village each evening where I sip wine, and play guitar with my friends. I have a full and busy life.”
>
> The American scoffed. “I have an MBA from Harvard, and can help you,” he said. “You should spend more time fishing, and with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, and eventually you would have a fleet of fishing boats. Instead of selling your catch to a middle-man, you could sell directly to the processor, eventually opening up your own cannery. You could control the product, processing, and distribution,” he said. “Of course, you would need to leave this small coastal fishing village and move to Mexico City, then Los Angeles, and eventually to New York City, where you will run your expanding enterprise.”
>
> The fisherman asked, “But, how long will this all take?”
>
> To which the American replied, “Oh, 15 to 20 years or so.”
>
> “But what then?” asked the fisherman.
>
> The American laughed and said, “That’s the best part. When the time was right, you would announce an IPO, and sell your company stock to the public and become very rich. You would make millions!”
>
> “Millions – then what?”
>
> The American said, “Then you could retire. Move to a small coastal fishing village where you could sleep late, fish a little, play with your kids, take siestas with your wife, and stroll to the village in the evenings where you could sip wine and play guitar with your friends.”

It's been scary to see how fast time has gone by since graduation. Asking stupid questions has helped me to focus on what's important, both at work and in my broader life.


The importance of "stupid" questions


The problem with crowdsourced reviews is two-fold. People refuse to admit that most experiences that they have are average (by definition), and additionally refuse to use the entire range of ratings at their disposal.

Dunkey described the problem [eloquently and comically in _Game Critics_](https://www.youtube.com/watch?v=lG2dXobAXLI), but his criticisms are valid for every kind of crowdsourced reviews.

Let's assume that we're rating restaurants on a five-star scale. Most people think that the average restaurant they go to deserves three or four stars. A good restaurant? Four stars. Slightly worse than average? Three stars.

Let's formalize this method of rating restaurants:

- 1/5: Unused
- 2/5: Unused
- 3/5: Worse than Average, Average, Good.
- 4/5: Average, Good, Great.
- 5/5: Great, Amazing.

The issue with the above system is that even with a large sample size, nothing useful can be gleaned. Not only that, the lack of one and two-star reviews imply that no restaurants are bad! It's astounding that people rarely complain about food they've **spent money on**, but this problem exists in nearly every other category as well.

Here's a much more sane way of rating restaurants:

- 1/5: Below average. A small minority of restaurants fall in this category.
- 2/5: Average. The majority of restaurants fall in this category.
- 3/5: Better than average, worth another visit.
- 4/5: Great. Worth recommmending to others.
- 5/5: Amazing. I'd recommend this to everyone I know.

This system of reviewing uses all five ratings, notably accepting the truth that the majority of restaurants that we go to are average, which is true by definition.

Why is this better? Currently, when I check the reviews for a restaurant in NYC, I always see a number between 4.0-4.4. It's gotten to the point where my brain doesn't even register the rating, as it carries absolutely no meaning despite the thousands of people who have "contributed".

If we all used the rating system described above, it would be possible for our collective crowdsourced opinion to matter.

> Note: Restaurants are just an example. This applies to any crowdsourced vote with a non-binary voting option.


The problem with crowdsourced reviews


In Drake’s song [Is There More](https://genius.com/Drake-is-there-more-lyrics), he laments over the simple question – is there more?

> Is there more to life than digits and bankin' accounts?
> Is there more to life than sayin' I figured it out?
>
> Am I missin' somethin' that's more important to find?
> Like healin' my soul, like family time
> Is there more to life than just when I'm feelin' alive?
> Is there more?

It’s fascinating that Drake, widely considered the most successful artist of all time, is asking this question. Drake isn’t an outlier in the music industry. Avicii committed suicide at 28, Frank Ocean and Kendrick Lamar disappeared from society after releasing #1 albums, and Taylor Swift and countless others have shed light on their mental disorders.

This trend is omnipresent – the most successful YouTubers are depressed, [America’s professional elite are miserable](https://www.nytimes.com/interactive/2019/02/21/magazine/elite-professionals-jobs-happiness.html), and those at the top tech companies increasingly suffer from burnout. Sports are no exception, with players across the major leagues coming forward to speak about mental health. Kevin Love, a NBA player, recently wrote about [suffering a panic attack during a NBA game](https://www.theplayerstribune.com/articles/kevin-love-mental-health).

It seems that as a society, we’re avoiding the important questions. Why is success in the career paths we value leading to severe anxiety and mental health issues?

Though this question merits endless debate, the answer might be that there is no meaningful value to be found in the work we do. Derek Thompson aptly said that the “conception of work has shifted from _jobs_ to _careers_ to _callings_”.

Work is expected to bring meaning to our lives. Meanwhile, study after study has shown that pouring our lives into work shortens our lifespans, makes us unhappy, and deprives us of quality time building relationships.

Since the most successful in any field are the ones who’ve devoted their lives to their craft, is it a surprise that so many are miserable?

We need to stop pushing this mindless agenda of working more and hustling harder, and make time to be happy in our short lives.


Is there more?


I’ve been obsessed with personal finance since starting full-time work last June. I’m going to cover FIRE here – but I plan on covering more topics in the future.

## What are tax-advantaged accounts?

First, let’s establish that if you’re investing your money, it gets taxed twice. When you get your paycheck, it’s already been taxed by the government. Let’s say I deposit that into my preferred broker and buy some stocks. Eventually, when I sell those stocks, the profits get taxed once more.

As the name suggests, tax-advantaged accounts let you avoid one of the two taxations, either pre-tax (when you get your paycheck) or post-tax (when you sell your investments). It’s straightforward to conclude that investing in a tax-advantaged account is always better than investing in a regular account.

## What accounts are tax-advantaged?

Unfortunately, for most Americans, only retirement accounts are tax-advantaged. Everyone can contribute up to $6,000 annually in an IRA, or if your employer has a 401k plan, an additional $19,500 annually.

The main reason younger people don’t contribute to these accounts is that the money isn’t accessible until you retire, or the old age of 65. [This is completely false](https://www.google.com/search?hl=en&q=how%20to%20withdraw%20from%20retirement%20accounts%20early).

In addition, there’s plenty of ways to avoid penalties on early withdrawals. Not only that, long term capital gains tax (the least tax you can pay on your investments) is 15%, while the early withdrawal penalty is 10%.

To make this more concrete, let’s say I bought stocks on Robinhood and sell the next year. I’d be taxed 15%, whereas if I had bought those same stocks in an IRA, I would only be taxed 10% if I withdrew the profits.

This means that it never makes sense to invest through normal accounts if you haven’t hit the contribution limit for retirement accounts first, regardless of when you withdraw.

## FIRE

The FIRE (Financial Independence, Retire Early) movement was eye-opening for me. Before learning about it, I assumed what everyone else does: we’ll be working for the next 30-40 years of our lives.

The movement isn’t just FI (Financial Independence), because FI+RE are intertwined. You can only truly be financially independent if you don’t need to work for money ever again, hence the “RE” part.

When I was in high school and I learned that index funds averaged 10% return, I realized that someone with 1 million dollars in the stock market could live off a salary of 100k a year indefinitely.

This is incorrect for a few different reasons, but FIRE is rooted in this basic idea: with X amount of capital, we can withdraw Y dollars indefinitely.

## Okay, how much can I withdraw each year?

Clearly, it’s not safe to withdraw 10% each year. In the case of a recession, we’d run out of money before the market recovered.

We won’t dive too far into the math, but even accounting for the worst recessions in U.S. history, the [“safe withdrawal rate” for early retirees is 4%](https://www.investopedia.com/terms/s/safe-withdrawal-rate-swr-method.asp). Feel free to research more, but yes, this means that you can live off of 4% of your investments indefinitely.

## What does FIRE mean for me?

Given what we’ve learned, the formula for FIRE is simple.

annual-income = (total investments) \* (safe-withdrawal-rate)

Let’s say you hypothetically want to live in NYC your whole life, and let’s assume you’ll rent a place for 2.5k a month. Allotting $30 for food each day (a bit extravagant) and $5000 for annual miscellaneous costs, we get:

(30 \* 365) + (2500 \* 12) + (5000) = 45,590

To achieve FIRE an annual income of 45,590, you would need 45,590 \* 25 = 1,139,750 in investments. With that amount, you could live off 45,590 for the rest of your life and never have to work again!

## How fast can I FIRE?

Here’s some projections for how fast someone could reach this with varying annual contributions, assuming a 8% stock market growth rate:

$30k: 18 years

$40k: 14 years

$50k: 13 years

$60k: 11 years

$70k: 10 years

Of course, extremely high earners can find ways to net even more in savings each year, but we’ll save these loopholes for another time.

The most common counter-argument I’ve heard at this point is “well, spending your money is more valuable when you’re younger”. I’ll point them to the book that many consider the genesis of FIRE – [Your Money or Your Life](https://www.amazon.com/Your-Money-Life-Transforming-Relationship/dp/0143115766).


Personal finance: FIRE


> Golden State Warriors power forward Draymond Green considers himself the greatest defensive player in NBA history.
>
> "The best defender ever? Me", Green said. [...]
>
> "That's what I believe," he added. "Wholeheartedly."

I know what you’re thinking. This is _arrogant_ on so many levels – how can a player say this before they’ve even retired? Besides, Draymond is clearly not the best defender of all time. I mean, have you seen [insert name] defend?

Well, let’s pretend that Draymond goes on to be the unequivocal greatest defender in history.

We’d look back at this quote and say that this was a sign of greatness. That despite all the haters, this _confidence_ propelled him past everyone else.

I think this example describes an important problem: we recharacterize arrogance as confidence after success. Why is this problematic? Confidence is universally agreed as an essential component of success, but we constantly discourage arrogance, when in reality the two mostly overlap.

I think the advent of social media has made this worse; phrases like “weird flex but okay” entering teen lingo show how omnipresent this confidence-cancel-culture has gotten, with studies showing younger generations are more insecure than ever.

This isn’t something that has an easy fix but something to be cognizant of. We shouldn’t seek to impulsively shut down someone for something sounding mildly arrogant, and instead remember that putting yourself out there is already difficult enough.


Confidence or arrogance?


I read a book earlier this year titled [How To Do Nothing](https://www.goodreads.com/book/show/42771901-how-to-do-nothing), which describes how we can take a break from the omnipresent attention economy, and take time to develop more meaningful connections.

However, I think the sentiments in the book are more applicable today than ever before. With millions in mandated quarantine, many of us are turning to our devices to simulate the connections that we had prior to isolation.

Apps like Facebook are [“just trying to keep the lights on”, as it “[strains] to deal with skyrocketing usage”](https://www.nytimes.com/2020/03/24/technology/virus-facebook-usage-traffic.html), while Netflix and YouTube have lowered their default quality on videos to deal with immense traffic. We can only imagine how much TikTok’s metrics have increased, with its short-form video keeping users hooked for hours at a time.

In some ways, it’s ironic that society as a whole is becoming its least introspective when we are all separated. Instead, we seek to resolve our anxieties by looking outward – consuming an endless stream of news articles, statistics, and data – only to avoid digesting what we’ve seen by inundating our minds with entertainment and social media.

This is dangerous for a number of reasons. Any app with an infinite feed only becomes more addictive the more its company learns about us, and the algorithms that back content engines continue to improve each day.

We risk diving deeper into our own bubbles, as we are fed content that already falls in line with what we believe. As Peter Thiel wrote, “the most contrarian thing of all is not to oppose the crowd but to think for yourself”.

However, thinking for yourself isn’t possible without introspection. This isn’t a plea to be more productive or to “make the most of each day”, but rather to take the time to disconnect. No matter how appealing the digital world may be at times, all we are staring at are pixels. Would we even notice if our feed were autogenerated, instead of being filled with actual content posted by real people?

It’s important to avoid deluding ourselves into believing that this facsimile of meaningful connection is the real world. Although this has been an increasingly prevalent problem, it’s been exacerbated further by current circumstances.

Instead, we should ask ourselves – can we take some time each day to do nothing?


How to do nothing


I've been asked how I find the motivation to do everything I want to. At least for myself, I think I've figured it out. Just have someone come up to me and tell me that whatever I’m planning is impossible, and you can be sure that I will put in 110% effort into proving that person wrong.

I guess this approach to finding motivation led me to always take more and more on. Over time, I redefined others' expectations of me – as my successes mounted, people doubted my abilities on fewer and fewer occasions. I began to expect more of myself as well, having faith that I would always be able to "figure it out".

Admitting that I couldn't do something seemed antithetical to my own beliefs – I imprinted the notion that I could always sleep less, focus more, and be more efficient with my time. I refused to deviate from these ideas, even when I thought that I couldn't take it any more. Ironically, surviving these situations only increased my faith in myself.

So naturally, coming into this semester, I had higher expectations for myself than ever before. I was enrolled in 21 credits, started the first semester of a Masters program, served as the Team Lead of Cornell AppDev and the Music Director of Absolute A Cappella, recruited for full-time opportunities after securing a return offer from Facebook, worked on shipping a [social polling app](https://cornellsun.com/2019/11/07/turning-idks-into-choices-students-launch-new-app/), and consulted for a [friend's startup](https://www.tryresponse.com/). Ironically, I'm writing this at 3:00AM on the plane ride back from the Y-Combinator Hackathon.

Turns out, this approach only worked to a certain extent. Although my success didn’t lead directly to more stress per se, it instead culminated in increasing levels of pressure. For me, it seemed that to everyone else my successes were preordained, which only furthered the fear of letting everyone down.

Throughout the semester, I would wake up after a full night of sleep feeling drained, something that I dismissed as a mental roadblock and not a symptom of something more serious. I only realized that something was seriously wrong when I couldn’t remember the last time I woke up not feeling completely exhausted.

I know what you're thinking – good job, you realized burnout exists 21 years after everyone else has. Why even share this?

Throughout my time in college, I never knew that other people felt this way. I assumed that my peers and the people that I looked up to simply persevered through their struggles – I thought that what I was dealing in the moment wasn't even that bad, that I lacked the willpower necessary to succeed, and that ultimately I was making a big deal out of nothing.

I guess I hope that sharing this helps someone somewhere feel less alone with what they might be going through. Feeling stressed and lonely is honestly the worst feeling in the world, and it's oppressing to believe that there isn't anyone who can relate.

For me, I've learned that it's harder to admit that I can't do something, rather than taking on more and trying to be the hero. People who care about you will ultimately understand, and being honest and opening up helps so much more than you might think.


Burnout


I played a computer game called _Darkest Dungeon_ in high school. You can take a look at the picture below to get a good sense of what the game is like. Simply put, it’s stressful.

![Darkest Dungeon Logo](Darkest_Dungeon_Logo.png)

Ironically, stress while playing the game is almost always caused by your _characters_, who are stressed as well. Stress is one of the defining mechanics of the game – when a player’s heroes encounter particularly disturbing enemies, barely survive a battle, or see their allies meet their end – the individual heroes get stressed as well.

Just as in the real world, stress has a cost in _Darkest Dungeon_. Reaching 100 stress (the cap) leads to devastating consequences for a hero. They develop afflictions, ranging from becoming masochistic, developing phobias, or refusing to follow directions that the player inputs.

However, there is a small chance that instead a hero will develop a **Virtue**, a positive affliction that gives them greater confidence and strength than those around them. Reaching their breaking point suddenly grants them greater resolve, and those who survive these high-stress moments become the leaders of future expeditions.

This system for describing stress is remarkably realistic. Forgive me for being morbid, but life is similar to _Darkest Dungeon_.

In the game, it’s emphasized that heroes willingly volunteer to venture into dungeons and confront their fears. The price they pay is the same price we pay in our own lives for taking risks – high stress, our fears, and sometimes even our own health.

The reward? A select few are able to thrive in these stressful conditions. Even as others around them become paralyzed by the challenge, some have the resolve to ultimately overcome their obstacles.

So why write this? Isn’t this something we know already? There’s a widespread notion that in order to be successful, we need to be “comfortable with being uncomfortable”.

Well, I think there’s more behind this: I believe that the price of taking risks is the same as in _Darkest Dungeon_. As we surmount more obstacles in our everyday lives, we continue to seek out new ones – more challenging and difficult than before. Mounting successes make us numb to the risk, but every challenge has its price, and just as in _Darkest Dungeon_, no hero is infallible.

It’s important to be mindful of the risks we take in confronting new obstacles: the price of failure can often be masked, and only upon failure can we comprehend the cost.

Unlike the previous essays, I’m not sure what the point of this one is.

On one hand, I feel that it’s necessary to push ourselves to confront new challenges; surviving from the brink leads to growth like nothing else in life. Many of the most successful people I know are survivors of high-stress all-or-nothing scenarios; I would ascribe much of my success to the same.

On the other hand, I’ve found it depressing to see my peers take on risks without knowledge of the consequences. Losing motivation, imposter syndrome, and the feeling that one’s best isn’t enough, are among the many costs that I’ve seen others pay.

Just as in _Darkest Dungeon_, these beliefs need treatment and recovery time, and attempting to disregard our afflictions can lead to disastrous consequences.

Put simply, I think stress is something that is trivialized in modern day society, and has evolved to become something that we don’t weigh enough in our risk assessments.


Stress


There's a short story called There's No Such Thing as a Dragon, by Jack Kent.

> A small boy, Billy Bixbee, spies a dragon sitting on his bed one morning. It's about the size of a house cat, and friendly. He tells his mother about it, but she tells him that there's no such thing as a dragon. So, it starts to grow. It eats all of Billy's pancakes. Soon it fills the whole house. Mom tries to vacuum, but she has to go in and out of the house through the windows because of the dragon everywhere. It takes her forever. Then the dragon runs off with the house. Mom still insists that the dragon does not exist, but Billy, who's pretty much had it by now, insists, "There is a dragon, Mom." Confronted with something that cannot be explained otherwise, Mom is forced to admit that the dragon must exist.

Wait, dragons don’t exist. Does this story even have a purpose? Here's my take.

As humans, we simply can't take in everything. The weight of the world upon us, _everything_, all at once, would be enough to drive us insane. To compromise, we focus on one detail at a time, taking what we observe and fitting the pieces into preexisting narratives. We choose to ignore what doesn't make sense, rather than question our own beliefs.

However, by ignoring what we see in front of us we often exacerbate smaller problems, and when we confront the "dragons" in our lives it's already too late. As people, we have strong tendencies to ignore warning signs and to brush off symptoms, choosing instead to believe that everything will be alright if we pretend it will be.

Jordan Peterson states this aptly: don't ever underestimate the destructive power of sins of omission.

One might ask, to call them sins – isn't that too harsh?

Consider a married couple, happily married three years. The wife of this couple begins to notice oddities in her husband's behavior. He spends more and more time away from home, conversations and intimacies become more abrasive and cold, and he spends all of his time with a new “friend” from work. Clearly, there's a dragon in her house. Confronting the warning signs would require, well, the same amount of courage as confronting a real dragon. Her perception of him would be shattered, consequently throwing her own identity into flux. She would no longer be in a happy marriage, losing a critical part of who she is. But with cognizant omission, when the truth eventually is revealed, the pain is so much worse.

Consider your own happiness. You've just began work at your dream job, and after a few weeks, you realize that you don't enjoy it as much as you thought you would. Your coworkers aren't the interesting folks you thought you would meet, your mentor seems disinterested, and the work just isn't fulfilling. You talk to your friends and family, the people you trust the most.

Oftentimes we only seek advice because we secretly want others to say something that's impossible to admit to ourselves, and this case is no different – but everyone knows how much this meant to you, and they assuage your fears. Ultimately, rather than confront the truth, you choose to stay and not question the bubble you live in.

The examples are never-ending. From personal health, to financial decisions, to our addictions, whatever they may be, we must be willing to ask what seems impossible and question ourselves honestly.

The moral of the story, then? Confronting a cat-sized dragon is certainly daunting, but even Billy knows to confront it before it grows bigger than the house.

At that point, you admit either that dragons exist or insist that your house walked away on its own - which is worse?

_Note: Inspired by 12 Rules for Life, by Jordan Peterson_


Self-deception


Following the crowd is easy. Too easy. While reading _Becoming_ by Michelle Obama, one of its passages struck a chord with me.

> This may be the fundamental problem with caring a lot about what others think. It can put you on the established path – the _my-isn’t-that-impressive_ path – and keep you there for a long time. Maybe it stops you from swerving, because what you risk losing in terms of other people’s high regard can feel too costly.
>
> For some, [law] might be truly interesting, but for you it is not. Maybe during those three years you make friends you’ll love and respect forever, people who seem genuinely called, but you yourself are not called. Your passion stays low, yet under no circumstance will you underperform. You live, as you always have, by the code of effort/result, and with it you keep achieving until you think you know the answers to all the questions – including the most important one. _Am I good enough? Yes, in fact I am._
>
> What happens next is that the rewards get real. You reach for the next rung of the ladder … at the age of twenty-five, you have an assistant. You make more money than your parents ever have.
>
> Is there anything to question? It doesn’t seem that way. You’re a lawyer now. You’ve taken everything ever given to you – and converted it to this. You’ve climbed the mountain.

There’s a common trope in childhood stories. Choose between someone who has money and is unhappy, or someone without much but is happy with what they have. Easy choice, right?

We’re told to “follow our dreams” and “pursue our passions”, but somewhere along the ride we realize that what we were told was just a white lie. Our peers who fail to follow the crowd and fail to excel at standardized tests are left behind, while those adept at staying ahead see their successes snowball.

But once you’ve climbed the mountain, led the crowd, what is there left to do? As Michelle Obama asked above, _is there anything to question_? Do we ever have room for our own passions?

It’s a question that I’ve been juggling over the last year. There isn’t a one-word answer or even a one-page answer. It’s a question that takes a lifetime to answer.

I believe that ultimately we innately know. Happiness is a _truth_, as subjective as it seems. Chasing our passions and dreams empowers us and drives us like nothing else. No matter how real the rewards get, nothing can fill the void of an unfulfilling career and life. Confronting the white lie “I’m happy” is something we’d rather avoid with endless perks and money, choosing to follow others as all of us have over the years.

If what we desire is nothing more than success in the eyes of the crowd, is it even success?


Following the crowd


Having the correct mindset is one of the most amazing tools we have access to. Let me explain.

Let’s say I believe that I’ve learned everything that I can at Cornell.

Every day I wake up with the mindset that my time is wasted, that I could accomplish so much more if I could slug through these required classes any faster. What could I possibly have to learn from professors who aren’t qualified, my peers who don’t understand what I know, from organizations that have nothing to offer? And guess what? Every night, I go to sleep with my assumption confirmed.

Not only is my brain wired to seek evidence that supports my claims, every situation I’m in is viewed through the lens that an opportunity to learn simply doesn’t exist. So, what does this mean?

If you believe you have nothing to learn, you have nothing to learn.

It’s an incredible self-fulfilling prophecy.

By believing that you know the most about some “subject A”, you have prevented yourself from every learning more. You’ve limited yourself and will never know more. Even if someone comes along who is smarter that challenges your assumption, you will be quick to dismiss their logic as unfounded.

How can we prevent this from happening? It happens to the best of us – the more we know about a subject, the easier it is to fall into this trap.

It’s essential to stay focused on this truth at all times. Wake up with the mindset that you have so much yet to learn, listen to your peers, and challenge your own assumptions.

Simply believing that you have something left to learn will allow you to learn more.


Mindset


Growing up, I used to devour books. The local library contained a treasure trove of entire universes to lose yourself in, and my mom made sure that we paid a visit every week. I remember when I held my first library card in my hands – it meant that _I could check out books myself_.

Near the start of high school I discovered the wonders of the Internet and I stopped reading as much.

From there, it only went downhill. Assigned readings in school never ceased to impress me with their dullness, it was as if teachers **wanted** students to lose the little interest they had in reading. “Wow, I can’t remember the last book I read” was common, even among my peers at Stuyvesant High School.

Recently, however, I’ve rekindled my passion for reading.

Want to learn something new? You can read significantly faster than you can understand a podcast or a TED Talk, and you can probably read much faster than you think (check out [this site](https://spritz.com/) to see).

Books written by industry leaders can distill years of research and experience into a few hundred pages. Sure, reading involves putting time aside, but consider it an investment for your future self. Would you decline having lunch with Peter Thiel or Michelle Obama?

The question is laughably ridiculous – who would say no? Then why not set aside some time to read what they believe is so important that this knowledge had to be shared with everyone? Despite this, we still find it difficult to pick up a book, and even more difficult to reach the last sentence.

I’ve found success by setting aside a small part of my day to dedicate to reading. Reading during a 30-minute commute twice a day results in 5 hours of reading, and that’s _just_ during the work week.

I also use a Kindle to read, which has many benefits: easy highlighting of pages, not having to carry around heavy books, being able to preview and buy books quickly, and having my collection live on the cloud.

Reaching out to friends and asking for recommendations can be a great resource as well. I was surprised to learn that nearly everyone I know has a favorite book, and by simply asking I found a curated list of books to start with.

I keep my reading list updated [here](https://youngkim.co/books), and I’m always open to any recommendations.


Reading


Something that I’ve noticed about the most successful people I’ve met is that they understand the value of sleep.

There are countless studies showing the detrimental effects of not getting enough sleep. I’ve recently read [Why We Sleep](https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144316), a book by Matthew Walker, and the consequences of not sleeping enough are brutal.

> Sleeping less than six or seven hours a night can increase your risk of cancer by 50%.
>
> Driving without sufficient sleep causes more accidents than alcohol and drugs combined.
>
> The physical and mental impairments caused by a single night of bad sleep dwarfs those caused by an equivalent absence of food or exercise.

It’s amazing that we live in a society where not getting enough sleep is the societal norm. Although sleep is clearly necessary, we do anything and everything to spend more hours awake.

This trend has been omnipresent throughout my life, and I’ve seen it reach its peak while attending high school and now college.

Because of this, it almost makes sense that with everyone coveting the same two goals – success and more time in the day – that the two would be closely knit.

I’ve found that it is the complete opposite. The most successful people I’ve met understand the value of giving their minds and bodies time to recover.

Rather than bending the constraints of our bodies through caffeine and other stimulants, they focus instead on making the best use of their time.

Adequate sleep has been proven time and time again to increase focus, creativity, and productivity: take some extra time tonight to invest in your tomorrow.


On sleep


Last August upon my return to Ramp, I was tasked with hiring for Procurement. At the time, the engineering team was comprised of myself, Kevin (one of my co-founders from Venue), and PaulS on FE.

My scope has expanded since, and as of the time of writing, I lead the Procure-to-Pay org comprised of three teams – Procurement, Vendor Management, and Bill Pay. I currently manage a team of 12 backend engineers.

All managers were once first-time managers, but the start of the management journey is especially challenging. Many smaller companies, including Ramp, avoid hiring for external people managers (a subject we'll leave out of scope here). At these companies, the main pre-requisite to having a report success as an IC. However, unsurprisingly, being a good manager requires a completely separate skillset from being a strong IC.

Prior to taking on reports, I solicited advice from more experienced people managers at Ramp, and a consistent recommendation was [The Manager's Path](https://www.goodreads.com/book/show/33369254-the-manager-s-path). I recommend this book to most engineers who ask for advice, since it covers all stages of an engineer's career from IC → manager → engineering leader.

With all of that said, we can get into an assortment of subjects below.

## An unreasonable ideal

In a perfect world, your management career would be filled with ideal reports. These reports would be self-sufficient, be receptive to feedback, surface how they're doing proactively, crush it at their jobs, and make your life simple as a manager.

In practice however, most of your time is spent coaching and working with others, approaching but never fully reaching the ideals above. Frankly, I think management is the ultimate "journey before destination" job. The joy derived as a manager is from the slow and steady growth you help others achieve.

## Guiding principles

I had a manager at Facebook who summarized their management philosophy as prioritizing "you (the report) first, then the team, then the company". My manager even explicitly mentioned that if I wanted to leave either the team or the company, they would do their best to support me on that path.

I generally agree with the philosophy above – as a people manager, your responsibility is to help your report grow and achieve their career goals, while balancing them with the company's goals as much as possible. Although it may seem counterintuitive, I strongly believe that prioritizing in the order above leads to better outcomes for both the report and the company.

## Notes and 1:1s

Have regular 1:1s. This is the simplest thing you can do to ensure your report feels supported and has a place to voice their feedback.

Take notes in the tool of your choice (at Ramp, we use Google Docs or Lattice). These notes should be date-stamped, contain an agenda of topics discussed, and have enough substance to recall what was discussed. These are crucial when you inevitably reckon with performance problems, and is also good to keep for your own sake.

## Feedback, aka being honest

The crux of being a manager is giving feedback to help your reports grow. If you don't give feedback, your reports don't know where they're doing well vs. where they can improve. Giving feedback on what's going well is easier but still important – for me, it's an exercise in paying attention and remembering to share it regularly. Giving constructive feedback is the real challenge.

A strongly held belief I have is that establishing transparency with your reports lead to much better outcomes. This is cultivated by regularly soliciting feedback on yourself, consistently checking in on how they're doing, remembering to follow up on any requests they have, and being there for them whenever tricky situations arise.

Assuming you & your report feel comfortable being transparent, sharing constructive feedback is much easier. Delivery of feedback is equally as critical as the message itself, but if I had to choose, the latter is more important. One mistake I made early on was overly softening critical feedback – this caused the severity to be misjudged, leading to misalignment on both sides. One way to sanity check this is to ask reports to summarize the feedback after delivery, to make sure nothing has been lost.

From what I've seen, a manager's inability to deliver constructive feedback is the most common reason for departures from a company. The most common failure mode here is falsely promising promotions (root cause: avoiding hard conversations), leading to extreme loss of faith afterwards.

In terms of how to deliver constructive feedback, always do the due diligence. Solicit supporting feedback from others and have specific examples in mind. You should never feel that you're having to make up examples on the spot – it's obvious to everyone if you haven't done your homework.

To summarize - be honest. Put in the work to have the hard conversations. They never get easier, but you're doing your report a disservice by avoiding them.

## Performance management

All people managers have to performance manage at some point. As mentioned above, the best preparation is consistently taking notes. These should also include any feedback shared above (Lattice has both shared & private notes, and I keep track of feedback delivery & reception in the private notes).

Ravi Gupta has a [great article on this subject](https://www.rkg.blog/rehiring.php) that I wholeheartedly agree with, and we'll be using this as the starting point for the rest of this section.

First, I think the above is something to aspire towards, more than something we can all immediately put in practice. There's plenty of reasons why we wouldn't enthusiastically rehire someone, but also continue to work with them because the company is a better place with with them there.

In my experience, most companies tend to be too lenient with performance management, which can lead to unnecessary layoffs and your most talented members feeling frustrated. [Amp it up](https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115) goes into detail on how companies are sports teams, not families. Great people want to work with great people, and when you don't hold the standard, it's easy to fall into mediocrity.

Assuming you're giving regular feedback, haven't been avoiding the hard conversations, and you've been taking notes, you're already on the right path. One piece of management advice that resonated with me was that most of your time, your gut instinct is right. When someone's underperforming, you probably know, but you avoid the signs because of the implications: performance management has a lot of friction, necessitates extremely hard conversations, and can reflect poorly on the manager. Despite this, it's important to follow through and help the people you work with grow.

Poor performance shouldn't be a surprise for your report. As a manager, avoid the pitfall of observing behavior and either not delivering the feedback or not giving your report time to improve.

## Hiring

First, I would recommend understanding the entire hiring pipeline end-to-end. How many candidates are getting hired on a monthly/quarterly basis, who's involved in the interview process, and how do prospective hires get assigned to teams?

Bad hires are incredibly expensive for a company, but even more so for the manager who needs to performance manage the report. Unfortunately, hiring is incredibly subjective, and it's more of an art than a science.

Here's some general advice I have:

- In my experience, communication is the least coachable attribute. I've never worked with someone who went from a poor communicator to a mediocre one. The ability to effectively communicate ideas is foundational to being successful, and being misunderstood (from poor communication) can lead to all kinds of downstream problems.
- Hire for slope over intercept. Regardless of seniority, willingness to grow is directly connected with open-mindedness. This can take many shapes – those willing to put in extra hours, those who want new challenges, or those who are always open to new suggestions to improve.
- Keep archetypes in mind. Part of good hiring is recognizing the gaps in your team. This isn't always about leveling – it can be [engineering archetypes](https://x.com/thiagoghisi/status/1572407124390445056?lang=en) as well. Although most companies don't think about this until IC6, you should consider the trajectories/archetypes of the members on your team when determining who to hire.

## Everything else & resources

This is by no means an exhaustive list, and there's far more that goes into management. Here's some resources that I've found helpful:

- [The Manager's Path](https://www.goodreads.com/book/show/33369254-the-manager-s-path)
- [Rehiring: Ravi Gupta](https://www.rkg.blog/rehiring.php), along with everything else on Ravi's blog ([here's another favorite](https://www.rkg.blog/play.php))
- [The Making of a Manager](https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0735219567)


Musings as a manager


For some reason, I'm oddly productive on plane rides.

It's no surprise to me that my most productive stretch for both writing/reading were in the last two months. As part of the Sequoia Arc program, we had to fly a total of three times to the West Coast and back. This phenomenon isn't a recent trend for me either – I distinctly remember writing [Burnout](https://www.youngkim.co/writing/burnout) at 3:00AM on a plane ride back to NYC, but I've had countless other examples like this in the past.

In [Deep Work](https://www.goodreads.com/en/book/show/25744928), Cal Newport mentions the prolific author Peter Shankman who took this to another level:

> And I brought my laptop and a sweatshirt and a power cord and my headphones. And I got on the plane and I wrote chapters one through five on the flight to Tokyo, I landed into Tokyo, went to the lounge, 14 hours, had a cup of coffee and a piece of sushi, took a shower, got back on the same plane, same seat, two hours later, and wrote chapter six through 10 on the flight home. I didn’t even clear immigration. I landed 34 hours like that later with a book. And then got held up Homeland Security for five hours because I didn’t actually clear immigration in Tokyo. But literally I spent $5,000 and everyone was like, “Oh my God, you’re crazy. You spent $5,000 to go nowhere.” I’m like, “No, I spent $5,000 to write a book because I know how my brain works.”

At least for me, on a plane, there's literally nothing for me to do. Falling asleep causes my legs to cramp, watching a movie on the tiny screen doesn't appeal to me, and the wifi has never been good enough to do any real procrastination.

A more interesting question I'd like to answer is how I might find the same level of focus without actually having to board a flight. I find that at home, I'm easily distracted by everything on the internet. I've purged consuming social media from my life, but I feel like I've replaced the time spent on social media with supposedly "better" sources (YouTube, Hacker News, NBA blogs, NYT).

Overall, I think that I just need to be more intentional with dedicating time to either read or write, especially on the weekends - but I've found this is much easier said than done. The end of the year is quickly approaching, and I'm behind my yearly goals (as usual) for both reading and writing. I'm hoping that blocking off time will be enough, but I guess we'll see in January of 2023.


Musings on productivity


Today is Day 26 of something new. TK, Kevin, and I are participating in the inaugural [Sequoia Arc Americas](https://arc.sequoiacap.com) program.

It's a bit insane to have those words on paper – starting a company has felt infinitely far from reach but something we've always wanted to do in our lifetimes.

## Why Now?

I don't think there's ever a great time to take the leap.

Most founders are outliers even prior to starting a company, and their career trajectories far outpace their peers. Therefore, they're already successful in their current role, making it irrational to justify taking such a large risk.

Ramp has a dense concentration of entrepreneurial talent, and my older coworkers remarked that past a certain age (28-30), it became far more difficult to start a company. Unless you were already well-off in life to begin with, getting married and having finanical dependents made the risk near-impossible to justify. Something else I heard at Ramp was that (1) it was hard to find the right co-founders, and (2) even once you knew who your co-founders would be, the timing rarely worked out between all the co-founders.

Given that information, here was my thought process: I'm almost 24 (at the time of writing), giving me a 4 year window to make the leap. There would likely never be a good time for me to start a company, but it was also unrealistic to expect that the timing would work out between Kevin/TK/myself in the future.

## Why Us?

It's a bit curious that we were accepted into Sequoia Arc, given that we got in with nothing more than an idea. The majority of pre-seed and seed investments are a bet on the team more than the idea (companies are expected to pivot while searching for PMF), and I think the same applies to us.

TK, Kevin, and I have known each other for over 10 years. We attended Stuyvesant High School before we were roommates at Cornell Engineering. We were finalists at YC's 2020 Hackathon, co-founded a company while in college (Pixelcode), and have worked on countless other side projects together (IDK, Hub, Crypto Wrapped). I also strongly believe that TK/Kevin were outliers before becoming founders: Kevin went from IC3 → IC5 in 3 halves in Facebook, while TK was Employee #20 and PM of the core product at Ramp. More impressively, they've displayed consistent grit and tenacity despite difficult times and failures.

This heavy emphasis on founding team makes sense. Companies are largely a reflection of the founders' beliefs and personalities, and the #1 cause of company failure stems from co-founder breakups. Someone told us that co-founder relationships are like "marriage without the sex", which I think is both funny and accurate.

## Why Arc?

When we sought out advice on starting a company, many people warned us that it would be impossible to do while having another full-time job.

We agreed that the ideal/unrealistic option would be having a blank check while we worked through the idea maze, but the second-best option would be to join an accelerator like YC as a catalyst to leave our full-time jobs.

We looked at a few – we considered YC, a16z Start, South Park Commons, the Neo accelerator. For reasons I'd like to avoid elaborating on here, we didn't apply to any of these (happy to explain over email for those curious). While we were looking at these, someone in our network told us about Sequoia Arc, a program that Sequoia was running for outlier founders at the pre-seed/seed stage for the first time. We put together the application over the next few weeks, eventually submitting on the day it was due.

We had a few interviews with a few folks on the Sequoia Early team, and were accepted into the program a few weeks before it started.

Participating in Arc was ideal for many different reasons, but I'd like to mention a few here:

1. Sequoia is arguably the most legendary VC firm
2. The 7-week Arc curriculum sounded invaluable as first-time founders
3. We wanted to meet other founders at the pre-seed / seed stage
4. Participating in the first Arc Americas cohort had asymmetric upside (similar to participating in the first YC batch)
5. We were excited to partner with Josephine/Alfred.

## Why?

I've saved the most interesting question for last – why desire to start a company in the first place?

I think everyone's motivations for starting something are rather different. For me, there's a few factors:

### Team

I was part of a project team at Cornell called Cornell AppDev, full of truly incredible people. We used to lament that after graduation, it seemed inevitable that you would work with people you didn't like, at a company you didn't care much about.

TK and Kevin are genuinely my version of a dream team. I'm also incredibly excited to create a team of world-class group of people that I'm excited to work with every day.

### Purpose

In my 2021 In Review, I wrote:

> I felt disillusioned working at Facebook. It was hard for me to believe that my work made a positive impact on society or that working at Facebook was the best use of my talent. The compensation, perks, and brilliant coworkers all sugarcoated the truth that no one at Facebook fully believed that they were achieving the vision of "making the world more open and connected".

Since graduation, I've leaned further and further into this ideology. Starting a company comes with innumerable burdens, but it's incredibly rare to have the opportunity to leave any imprint on the world we live in. I want to continue to search for meaningful purpose in my life, and starting a company is another step in that direction.

### Family

My parents have had an outsized influence on what I believe today. They've sacrificed tremendously to ensure that my sister and I would have access to the opportunities that they did not, and it's a responsibility that I do not take lightly.

I've spent a long time thinking about what it would mean to best repay them for their sacrifices, and I've realized over the years that access to opportunity is so critical because it affords you the luxury of choice. Whereas my parents had many paths in their lives closed off to them, I've consistently had the freedom to choose.

I've been successful in my career thus far, and I don't think I've hit the limits of what I can do yet. Ironically, I don't think I'm searching for success – I'm searching for failure on the largest stage possible. Until that point, I don't plan to reduce the scale of my ambition.


Starting something new


Last Friday, September 9, was my last day at [Ramp](https://ramp.com/). It was by far the best place I've worked in my short career.

## The best of times

I joined Ramp last October (as briefly mentioned in my [2021 in Review](https://youngkim.co/writing/2021-in-review)) as the ~170th employee and the ~30th product engineer.

Ramp, for the uninitiated, is an all-in-one platform for finance teams, and its flagship product is  its corporate charge card. For much of its history, Ramp did not support disputing transactions in-app, and instead customers needed to file tickets with support.

A few months prior to my joining, Ramp finally added the ability to dispute transactions in-app and ever since, customers had been disputing an exponentially increasing number of transactions MoM (month over month). This put significant load on Risk Operators to (1) decipher whether the dispute was valid and (2) file the dispute with our card issuing partners via dashboard. To put it into perspective, this was taking 5-10 minutes per dispute, and it was untenable to have this much burden on Risk Ops as the company scaled.

The week I joined, my manager [Pablo](https://morepablo.com) told me that I would be singlehandedly staffed on solving on this problem and automating the workflow here. The end goal of the project was for (1) Risk Ops to crystallize the SOP (standard operating procedure) around determining valid disputes, and for (2) engineering to build tooling to one-click file disputes. With these combined, Risk Ops would be able to hand off disputes entirely to Support.

I was worried I wouldn't be able to ramp up quickly enough to the codebase and the necessary business context, never mind taking on a project like this solo. Nevertheless, the project was a perfect fit. I was well supported cross-functionally, and I was able to ship the project in a few weeks.

What was next? Pablo (my manager) mentioned a new greenfield project Ramp was considering named "Float". The idea was simple: Ramp had a [Bill Pay](https://ramp.com/bill-pay) product where businesses could pay invoices for their vendors directly on Ramp. We wanted to layer on a lending product on top, allowing businesses to get net-30/60/90 day terms. In retrospect, this was a brilliant idea. Ramp is uniquely well-positioned to underwrite businesses, as Ramp has extensive card history + other data (accounting, bank account data, etc) used to understand business health for the card product.

The team was lean from the start – Sam Packard on Product, Jason Li on Design, and three engineers – Max Lahey, Sashank Thukpari, and myself. The initial product spec was written by December 2021, and we began work in earnest after the start of the new year with the ambitious goal of shipping a MVP in March.

After two months of long-running Zoom meetings, shipping code as quickly as we could open pull requests, and a late name change to Flex, we shipped the MVP in mid-March. It wasn't obvious that Flex would be a success from the start. We outbounded to about X businesses (number hidden intentionally), and although we we were able to sign up a sizeable percentage, businesses weren't actually using the product and initiating loans.

We suspected that there could be a few reasons for this. (1) Flex had no PMF, (2) variability in when businesses sought out loans, (3) the interest rates we offered were not competitive enough. We sprinkled a few growth hacks for Flex throughout the product, such as interstitials deep-linking to the product or banners within the Bill Pay product.

After a few more weeks, our patience paid off - we had our first loan initiated on Flex. Over the next few weeks, it became clear that the product was incredibly sticky for businesses using the product, and that it was worth investing in this greenfield project further.

We ambitiously set a target date of August 15th to launch the product for GA (general audience), and began working on the necessary feature set to release to everyone. As Sashank noted in his [twitter thread](https://twitter.com/sthupukari/status/1562247342278860800?s=20&t=B2QR1vSUcsPl8LHA6VJ5uQ), this was a major cross-functional effort. It was my first time witnessing the level of coordination required for a large product launch, largely driven by Subham Agarwal and Serena Mackool. Ramp invested more engineering support for the GA launch, with Arnab Dey and Jack Chau (intern) contributing.

Despite some last-minute hiccups, we launched the product on time and bug-free (thankfully). [Here's the blog post](https://ramp.com/blog/announcing-ramp-flex) on the product launch for those interested.

I'm truly honored to have worked with such a brilliant group of people to make the launch happen. Although I'm biased, I wholeheartedly believe that the core team that shipped Flex is the most talented team at Ramp.

## Reflections on Ramp

It's certainly bittersweet to say that I'm leaving Ramp. There's definitely a world where I stay there for the rest of my career. Although no company is perfect, Ramp is far closer than any company I've seen.

I've been asked what made Ramp such a special place to work. I think like everything else, it always comes back to the people. Ramp is incredibly talent dense, and especially so in product/engineering/design. Assembling talent of this caliber is already rare, but it's even rarer to have a culture where everyone is highly motivated by what they work on.

During my time, I was particularly inspired by two people – Max (TL on Flex) and Sam (PM on Flex). Max is incredibly thoughtful and humble for someone who is correct nearly all the time, and I was awed by his ability to take complicated problems and eloquently communicate concrete paths forward. Sam is detail-oriented and can absorb information at an unbelievable rate. We used to joke at Ramp that Sam could be replaced by sentient AI, and we wouldn't be able to tell the difference. I'm certain they will continue to bring the best out of everyone they work with.

Karim/Eric/the rest of the leadership team have done an unbelievable job bringing Ramp this far, and I'm excited to finally be on the other side as a Ramp customer.


On leaving Ramp


I'm thrilled to say that on May 1st, 2022, I ran my first half-marathon.

![Half Marathon](half_marathon.png)

I ran at a 10'24" pace, a much better pace than for any long run that I've had so far. Kevin told me that the adrenaline on race day is like nothing else, and although I don't ever remember feeling the adrenaline, the atmosphere of the half-marathon was amazing.

My start time was at 7:00AM, which I didn't know is typical for most races. I carb-loaded the night before and attempted to sleep at 9:30PM, with the plan to wake up at 5:30AM and eat a small breakfast. I ended up not eating anything when I woke up, but this ended up being fine! (although I had some anxiety about this few miles into the race)

I was conscious of pacing myself for the first few miles – I'd seen plenty of warnings online cautioning against burning out at the very start of a race. After the first few miles I felt like I was warmed up, and I was able to maintain a steady pace throughout.

My parents + sister came to watch the last few miles of the race, which provided some much-needed motivation in the finishing stretch. I'm really proud that I didn't stop to walk once! This was unexpected – in all of my long runs, I'd always walked in the latter half.

Overall, I'm ecstatic that I was able to complete the half-marathon! I remember during my first run in December (only five months ago!), I couldn't even run half a mile without feeling like my heart was going to jump out of my chest.

In terms of what's next, I plan to continue running and perhaps fit in another half marathon this year. I want to continue improving my pace and target running a half-marathon at a sub 10' pace. Afterwards, I'll consider preparing for a marathon!

*The rest of this contains check-ins that I wrote while preparing.*

### December-January Check-In

- **December Summary** | 9 Runs &nbsp;| 17.3mi | 12'47" Pace | 3h41m Time Running
- **January Summary** &nbsp;| 14 Runs | 44.3mi | 11'44" Pace | 8h39m Time Running

In December I was running casually without any serious plan in-mind, whereas this month (January) I took running more seriously given my goal of running a half-marathon in May. I signed up for a race on May 1st, and I'm both happy with my progress so far but worried I won't be ready in time.

Here's some notable runs over the last two months:

- December 4 | First Run | 2.17mi | 12'51" Pace
- January 1 &nbsp;| First 5K &nbsp;| 3.13mi | 10'52" Pace
- January 28 | First 10K | 6.41mi | 11'47" Pace

Looking through training plans online, most recommended running 3-4x a week, with one long-run each week that increments by one mile. I've been trying to stick to that regimen, making sure to fit in a long run each week, and I'm proud that I capped off January with the longest run of my entire life.

**Goals for February**

- Long run of 10mi at 12'00" or under

I think the above goal will reassure my fears of being unable to finish the half-marathon, and from there I can continue to build up my pace. My goal is to shoot for 10'30", but we'll see how realistic that is as the weeks pass.

In the meantime, my biggest obstacle is the weather. I've been checking forecasts regularly and planning around single-digit temperatures and rain/snow, and I've been fairly lucky so far with timing. I've also picked up the habit of drinking protein shakes immediately after my runs, which I _think_ has been helping with my recovery.

### February Check-In

- **February Summary** | 14 Runs | 45.8mi | 10'48" Pace | 8h15m Time Running
- ❌ Long run of 10mi at 12'00" or under

I spent slightly less hours on the road than January but increased my mileage slightly, thanks to my improved pace. I struggled to have as much mileage as I wanted because of some inclement weather and only having 28 days in February, but overall I'm happy with where I ended up. I was able to improve my pace by nearly a full-minute, and I continued to push myself in my runs, especially towards the later half of the month:

- February 20 | 8.03mi | 10'35" Pace
- February 27 | 3.77mi | &nbsp;9'59" Pace

**Goals for March**

- Long run of 10mi at 10'40" or under
- Run 60mi

My half-marathon is slated for 5/1, and I'm starting to feel the time crunch. Recommendations are to run 11mi two weeks prior to the race (4/17), and I want to make sure I'm as prepared for April as possible. I'm planning to run as often as possible over March, ideally hitting 60mi this month.

The weather has been improving (which means I can run slightly lighter with less layers). I noticed during my 8mi run that my legs (especially my calves) were the limiting factor, so I'm going to focus on increasing mileage and ramping up the workload on my legs.

Finally, in terms of pace, aiming for 10'30" for the half-marathon seems realistic/likely at this point, but we'll see how things progress over this month.

### March Check-In

- **March Summary** | 15 Runs | 56.1mi | 10'48" Pace | 10h04m Time Running
- ❌ Run 60mi
- ❌ Long run of 10mi at 10'40" or under

I missed both my goals this month, but came fairly close in terms of mileage. I had some right foot sole pain during the second week of March that prevented me from running as much as I wanted, and I was in Utah 3/14–3/21. I realized that I was having sole pain due to lack of support in my shoes, and replacing the soles of my Nikes with some heavier-duty soles helped reduce the pain significantly.

Here's my notable run of March:

- March 6 | 9.12mi | 11'14" Pace

I wasn't able to get to the 10mi mark like I wanted, but I'm still happy that I was able to diagnose and figure out why I was having foot pain.

**Goals for April**

- Long run of 10mi

I'm being conservative with my goals this month since the plan is to taper off my mileage the last two weeks of April. Fingers crossed, everything goes well since April will be my last month of training!

### April Check-In

- **April Summary** | 14 Runs | 54.9mi | 11'12" Pace | 10h14m Time Running
- ✅ Long run of 10mi

Notable runs:

- April 9 | 10.31mi | 10'52" Pace


Running a half marathon


It's bittersweet to say that today is my last day at Facebook. I interned at the company twice and worked fulltime for about 18 months, and saying it was instrumental to my growth would be a major understatement.

Here's some lessons learned:

On ramping up...

- Read through as many pull requests as possible, it’ll help you understand what other people are working on.
- Don't be afraid to ask questions on pull requests. Often times an outsider's perspective is more valuable than someone already familiar with the codebase.
- Document stuff as you learn it, then you can teach it to others ramping up later on.

On coding...

- Read the documentation of the language you're using end-to-end. It'll save you so much time in the future.
- When reading new code, start with data structures & interfaces before diving into the actual code itself.
- If something feels wrong in terms of implementation, it's probably wrong.

On success...

- Great coders aren't necessarily great engineers. Code wins arguments in the short-term, but in the long-term relationships are key.
- De-risk as much as possible as early as possible.
- Help others as much as possible.
- Over-communicate, both your successes and when you need help.


Recent writing

Annual reviews

Reflections

Essays