Find Your Why

How to abandon the superficial to find a truly fulfilling career.

This is an excerpt from my newsletter about getting hired, Launchpad. For more of this every week, click here to subscribe (it’s free!).

(Also, thank you to the following people for helping me proofread and edit this piece: Teresa Pho, April Shin, Brian Chan, Anna McMurchy, Danil Kolesnikov, Charlotte Chen, Jessica Zhou, Samuel Stowers, Akshay Chalana, Jasmine Sun, Emily Huang, and Angela Liu.)


Everyone seems to have a different set of rules to "be successful" in life.

Some, believe in maximizing short-term gains to achieve long-term flexibility (think working at a company with awesome pay but bad work culture or mission because, well, the pay is awesome).

Others believe in maximizing long-term happiness through chasing a social mission, like working for Doctors Without Borders instead of joining the Mayo Clinic.

As a former debater (lol), I'm going to firmly argue that everyone - no matter your background or field of study - ought to be a member of the latter camp, but not necessarily for moral reasons.

To be clear: I believe that everyone should care about solving a meaningful problem in this world, and they should either be working towards understanding what problems they want to solve, or be actively solving them at all times.

This is actually a quite contrarian position. If you read through student forums on the hiring process, it becomes clear quite quickly that they focus heavily on concrete things such as how to effectively negotiate salary offers, craft cover letters (I'd argue incorrectly, but more on that later), and optimize for the most prestigious jobs, which in tech means jobs at Google, Facebook, Apple, and others.

The default position, if I were to summarize it briefly, is this:

  • Your job, from high school onward, is to survive the next round of "the tournament," a process that involves constantly culling the weakest competitors among you with the eventual goal of getting that cushy Google job.
  • From here, you have to make it into a great college, one with a terrific brand name and lots of alumni working in your field (like MIT, or Stanford, or Waterloo).
  • Then, if you're at a large school (like Berkeley), you need to compete to get into the best CS clubs, because they give you access to recruiters and direct connections into the top companies. If you're at a small school, you might focus on joining certain academic frats/sororities that have people who "get in" to the top places.
  • You'll need to get at least one solid brand name internship on your resumé,and probably work in a major tech hub, like San Francisco/San Jose. While you're at your internships, you'll spend most of your time networking instead of doing work, going to as many events as possible in an effort to meet the kid who'll get you that "in" to the next opportunity.
  • You'll go back to school, trudge through classes you might not care much about, and keep crafting a "unique narrative" of being a CS genius who's more experienced than their age would suggest, a member of the elusive "top 10%" that companies want to hire.
  • You might start a startup, because it "shows you can take initiative," and apply to your college's startup accelerator. The company won't go anywhere, but you're now a "founder," and you'll display that proudly on your resumé.

By the end of four years, you'll have club leadership titles, a fancy degree, "founder" status, and a brand name internship, if you play your cards right.

And even then, you still might not get the job.

Your Google internship might not turn into a return offer.

You might not get all those leadership titles.

You might have a bad quarter and get a lower-than-expected GPA.

You might not get into the fancy CS clubs.

You might not get into MIT.

And, as the traditional narrative would dictate, if any of those things fail to materialize, if any of those 'steps' are missed, you won't be "happy."

The problem is, this model just doesn't fit reality.

I know plenty of [insert large company name here] engineers who hate their jobs. I also know plenty who love them.

I know people who work on startups who honestly shouldn't, because the stress is insane, but I know many who enjoy it every day.

There are people from MIT, Stanford, and along prestigious institutions whose students are deemed some of the most talented and intelligent people in the world. Then there are those from the same population that fall short of their peers. And there are CC transfers and community college students that far outshine their four-year counterparts.

Since moving to San Francisco, I've been truly privileged to learn from and hang around people that have inspired me so much whether that be 17 year olds working on brain-computer interfaces or Google developers leading initiatives to make tech more accessible.

Many of them went to prestigious schools, worked prestigious jobs, and "won" the so-called "tournament." But many didn't.

And whether or not they were "happy" with their current state had little to nothing to do with what school they went to or what job they had.

There was a commonality, though.

The people I found to be most "satisfied" with their career paths cared primarily about one thing: impact.

  • Some greatly enjoyed difficult engineering and design challenges, and found companies like Tesla and Impossible Aero - who are taking on massive problems in the world - fascinating.
  • Others cared about social impact, and enjoyed working at companies with a primary social mission: Khan Academy, Quizlet, Jopwell, the list goes on.

Companies like Google, Facebook, Apple, etc fit in that mix as well.

Some of the happiest Apple employees I know believe that Apple's business model of charging customers upfront for hardware to preserve customers' data privacy to be a moral good.

Meanwhile, some of the happiest Facebook employees I know believe the opposite, that advertising-fueled business models benefit the world by increasing access in a way making money off of $1500 iPhones cannot.

I'm not weighing in on these debates, I'm just pointing out that of all the people I've met in this city, the people most happy with their status and work are engaging in them.

They're not just showing up every day to get in, do a job, and get out. They're not just investing time to build up their 401k.

They want to build up a base of knowledge in something they love, and apply it to problems they find challenging, relevant, and impactful.


Last week, Patrick Collison (CEO of Stripe) published an article on his website entitled "Advice" where he talked about this very thing.

If you're between 10 and 20 years old, Patrick recommends to "go deep on things [...] become an expert," to "make friends over the internet with people who are great at things you're interested in," and "make things."

Most importantly, he says this:

"If you're in the US and go to a good school, there are a lot of forces that will push you towards following traintracks laid by others rather than charting a course yourself. Make sure that the things you're pursuing are weird things that you want to pursue, not whatever the standard path is. Heuristic: do your friends at school think your path is a bit strange? If not, maybe it's too normal."

Were you told that in middle school, in high school, in college?

Was that the path you chose?

If you're like most people, there's a good chance the answer is NO, because you were told that following the dreams and aspirations of your childhood was childish, that you ought to just follow the perfectly defined, perfectly reasonable traditional path in front of you.

So, I want you to ask yourself: how's that path been so far? Are you enjoying it? Are you doing fine?

If so, there's no need to read further. You'll be fine. You know what you need.

After talking with hundreds of students at the 30+ schools I visited over the past few years, though, I feel like I can say with some confidence that most of you would answer those questions with no, I'm not fine.

No, this path isn't working.

I'd argue, though, that the core problem is that you've been optimizing for the wrong stuff. You don't need to jump through more hoops, chase more meaningless emblems of prestige, and do things for the sole purpose of "advancing your career", whatever that means.

Because if you do - "advancing your career" for your "career's sake", you'll forget to actually do things for you.

You are not defined by how interested your aunts and uncles are in your job title at Thanksgiving dinner. You are not defined by your salary, or your vacations, or your Instagram feed.

Have any of these things actually made you happy? Actually happy? In a way that was sustained beyond a momentary dopamine hit followed by a crash?

But let me tell you the real kicker: not only is a mission-driven career more impactful, not only is it more rewarding to you, personally…

…but it’s also more likely to earn you those very “emblems of prestige.”

It’s more likely to get you the sort of job your family will “approve of.”

It’s more likely to result in you starting the company of your dreams.


When I started building a hiring platform for students almost three years ago, my first step was talking to as many recruiters as I could to try and understand the hiring process as clearly as possible.

So, I did: I talked with recruiters big and small, from large companies like Facebook and Google to hiring managers at small 20 person startups emerging from accelerators like Y Combinator, 500 Startups, Techstars, and more.

I’d even go to tech conferences like GitHub Universe where I knew recruiting staff would be and probe them with questions. I had a similar opening each time, with the intention of catching them off guard:

“Hi, I’m a college student, but I’m actually not interested in applying for a job at GitHub. I actually run a company called SolverIQ and we connect students with jobs. Could we chat for a few minutes?”

It was through those conversations that I began learning more about the mindset and process recruiters use to actually evaluate applications.

I would learn that mission fit and culture fit are among the most important factors in a junior candidate’s hiring, because of their impacts on the candidate’s likelihood of staying for a longer period of time (maximizing ROI), as well as the frequent calls from the C-Suite to “improve company culture.”

I would learn that companies hired by referral not because they truly believed that “hiring through your friends” gave them the best chance at identifying ALL of the best talent, but because since everyone writes the same damn things on their resumés and cover letters — “a swarm of carbon-copied robots,” one recruiter told me — most cold applications are virtually unidentifiable from each other.

But, most importantly, I would learn that the second recruiters saw an ounce of humanity in a candidate, a shred of evidence of real passion for the work the company does (or even just real passion for anything!), the candidate was shortlisted.

If you believe any of the following things:

  • That your starting salary (unless it’s below the baseline for your region, so $100k in San Francisco for CS) actually matters at all;
  • That you ought to prioritize working at a brand name company because it’ll make you “more valuable” in the long run;
  • That your own dreams, passions, and desires — including those you had as a child — are the work of a child, and thus not relevant to the needs and wants of an adult, to achieve a higher level of professional prestige;

…then I don’t blame you!

We’ve all been brought up to prioritize these things.

But, based on everything I’ve seen thus far, it doesn’t seem those ideas are actually true.

If you know what problem in the world you want to solve, then go out and solve it. Find people solving that problem already, and ask to join them — or better yet, if you’re earlier in your career, ask how you can be of value.


There’s no better example of this than Laura Deming, the founder of Longevity Fund, the first VC firm dedicated to “curing aging” and a Thiel Fellow and Forbes 30 under 30 recipient.

Here’s her story:

“For starters, the 23-year-old, New Zealand native was home schooled, developing along the way a love of math and physics and, perhaps most interestingly, the biology of aging. In fact, she became so preoccupied with the latter that at age 11, Deming wrote to Cynthia Kenyon, a renowned molecular biologist who specializes in the genetics of aging, asking if she could visit Kenyon’s San Francisco lab during a family trip to the Bay Area. Kenyon said yes. When, soon after the visit, Deming asked if she could work in the lab, Kenyon said yes again. (…) by age 14, Deming was a student at MIT, and two years after that — at the tender age of 16 — she was a college drop-out, having been accepted into Peter Thiel’s two-year-old Thiel Fellowship program (…) Deming pitched the idea of a venture fund that would support aging-related startups, and has since turned that early concept into Longevity Fund, an early-stage venture outfit that just closed its second fund with $22 million.”

Some of you are probably thinking, “That could never be me.” And that’s probably true! Laura’s one of the most brilliant people her age.

But that process is replicable. When people have genuine passion for things, people are attracted to them. They want to help them.

There are people at giant prestigious companies and awesome prestigious schools who are happy, and there are people who are not. If we’re examining the correlation between prestige and career satisfaction, it doesn’t seem that one exists — or at least, it isn’t a strong one.

My argument is that among those who make lots of money and those who make little, among those who lead and those who follow, it is almost always true that those who (in the words of Simon Sinek) start with why — with a purpose and reason for being — are those who live the happiest, most fruitful, most fulfilling, and most productive lives.

If you’ve made it to the end, thank you — I’m so happy you’re here.

You’re going to do great things.

🚀


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