Early career advice
2025 August
I've been commonly asked what advice I have for ambitious engineers early in their career. I've found that the real question they're asking is "how can I have an outlier career?".
Unsurprisingly, there isn't a single playbook to follow, though I've found a few guiding principles helpful. Most of my advice comes from resources that I've read over the years – these are linked at the bottom.
Seek arbitrage (seek suffering)
Pre-watch: anecdote from Jeff Bezos
Everyone realizes one day that there are people much smarter than them. Growing up, I thought I was better than my peers at math, until I realized in high school that there were others so much smarter I could never catch up.
If you follow the footsteps of those smarter than you, you'll fall further and further behind. The solution is to seek arbitrage and find opportunities that others are undervaluing. I've observed most people avoid jobs correlated with suffering, because there are often easier & similarly prestigious ones available.
As an example, I went through team selection at Facebook after graduating college. Everyone knew that there were specific teams (Ads) where people worked longer hours, but could demonstrate more impact and get promoted more quickly as a result. Despite that, most people avoided Ads because they wanted to work less.
You'll build resilience through these opportunities regardless of whether you succeed, and over time I've found that true resilience is increasingly rare as I've advanced in my career.
Where to work
Pre-read: Play for the front of the jersey
As Ravi mentions above, the most important thing to optimize in your career is to play for winning teams.
First, there are few true winners. Technology is continually a shifting landscape, but there are only a handful of companies that survive decades. As an example, despite the number of competitors that previously existed in search (Yahoo, Jeeves, MSN search, Google) or food delivery (GrubHub, Seamless, Postmates, Doordash, Uber Eats), value ultimately accrues into one or two companies for each vertical/industry.
Identifying winners among public companies is straightforward, since information about these companies is well-publicized – everyone agrees on FAANG + trading firms + "Big N". The smaller the company though, the more challenging it is to identify whether they're a future winner. I generally see this on a spectrum:
- Large company: easy to tell if they're a winner, less upside/learning/opportunity/risk
- Small company: hard to tell if they're a winner, more upside/learning/opportunity/risk
My general advice is to go to the smallest possible company where you have high confidence that they're a winner, to maximize opportunity while minimizing risk. Early in your career, a safe bet is to join a pre-IPO company. As you advance in your career, you'll expand your network and accumulate more insider knowledge, which will reduce the risk of going to earlier stage companies. You'll also be able to meaningfully inflect the trajectory of a company yourself.
If you want to go earlier stage, my suggestion is to start with a company's investors. VC firms do this for a living, and use insider knowledge & due diligence to decide what companies to invest in. It is nearly impossible that you're identifying an opportunity that VC firms are missing. Put simply – if a company does not have strong investors, regardless of what stage they are at, you should not join them.
There are "tiers" of VC firms online, and each firm generally publishes its investments online (this won't include companies in stealth). I suggest looking at companies Tier 1 firms invested in as a starting point. As mentioned above, you should seek arbitrage – if you find that you're unable to land opportunities at your wishlist companies, you should work your way earlier & through investor tiers.
Humility
“You are what your record says you are.” - Bill Parcells, NFL coach
I've talked to a number of students that want to work at X company, lament that they're unable to get hired, but are also unable to recognize that they don't meet the bar from an experience / technical perspective. My diagnosis is that they're lacking enough humility.
Experience and prestige generally snowball, and everyone starts somewhere. My suggestion is to get your foot in the door somewhere, no matter the company, and prove you are as good as you say.
Be your biggest critic, and this will keep you grounded as you accumulate more experience & success.