Career Advice That Doesn’t Suck

Work harder, bet bigger

I’ve taken a lot of career and financial risk, more than almost all of my peers. While I view my decisions as largely rational and effective, I tend to keep most of my decision rationales and work habits to myself.

Much of my decision to take early career risk can be attributed to select blogs, books, and talking with a lot of people, especially older mentors. Since most of my friends already think I'm pretty weird, I figured I'd open-source some of my work habits and decision rationales that have shaped my approach:

• Working multiple jobs for a period of time and using the earnings to have a period of unemployment (what I’m doing currently). This has enabled me to prevent myself from (1) being anesthetized by my job and becoming complacent, and (2) giving myself full latitude to work on projects in-depth, not as perpetual half-assed “side projects”.
• Two super intense deep work days per week where I go zero to one with no distractions. This is usually Sunday and Tuesday, where I work with the aim of having the highest output day possible. The other days are spent largely editing the work product from these days or otherwise lighter work modes.
• Doing way more and trying way harder; no one is even trying. Successful people just have way more output than their peers who are often equally as smart and capable. “Work smarter not harder” is some of the worst advice I’ve received. You need to put in the hours and understand the context to determine what’s important and what’s not. July was a particularly high-output month for myself, writing 50k+ lines of code and 10,000 words, averaging 4 hours of deep work for 6 days a week.
• Reading long-form books regularly, with 1-3 intensive subject deep dives per year on specific topics or classics. I schedule reading during lighter work periods since books become a major distraction during my high-output deep work sessions.
• Not working on the hardest thing I can. You can make large contributions to many fields and working on the hardest thing is often irrational. My driving thought process is asking myself where I think I can make a large marginal contribution with my skill set.
• Writing on the internet to sharpen my thinking and increase the surface area of serendipity. I write across a variety of topics and personas which allows me to have edges and peer groups at the frontiers of different subject areas. Take the initiative to meet people in person and learn about their production functions.
• Understanding the long-term games worth playing. Becoming the best badminton or chess player is impressive but very capped. Think about playing in positive-sum environments where you can own a unique spot on a growing frontier.

I certainly do not advocate for most people to follow my work habits or career choices. It is best interpreted as real work habits from your friendly internet anon who isn’t successful (yet) and who has no incentive to lie. (If I really was successful, would I really be toiling away writing this blog?)

Lessons from Kelly

The Kelly Criterion is utilized in binary outcome environments and describes how much to wager for a bet given certain constraints. It is used to optimize long-term expected value of your bankroll. The inputs are:

• The size of your current bankroll
• If your bankroll is replenishable
• The probability of an event occurring
• Your edge in the market

In kind environments where feedback is honest and frequent, Kelly is a useful model. You can place 1 million sports bets and determine if you are a winning or losing player on average and use Kelly or fractional Kelly to give pointers on how much you should bet.

Kelly formalizes the natural intuition that you should bet larger when you have a bigger edge and less when your edge is smaller. The less intuitive part is how the math works out:

For even money (1:1) odds, Kelly suggests:

1. 80% market probability, 10% edge → 50% of bankroll
2. 50% market probability, 10% edge → 20% of bankroll
3. 10% market probability, 10% edge → 11% of bankroll

The overwhelming majority of people would not bet 50% of their net worth on a single binary event that is priced at 80% with a 10% edge. These numbers are amplified when the payouts follow power law outcomes, as career outcomes do. If your YouTube channel or startup succeeds, the payout is more like 100:1 in finances and time reclaimed.

Under the same conditions but with 100:1 payout odds, Kelly suggests:

1. 80% market probability, 10% edge → 90% of "life bankroll”
2. 50% market probability, 10% edge → 60% of "life bankroll"
3. 10% market probability, 10% edge → 20% of "life bankroll"

Kelly tells us that we should bet 90% of our life bankroll on something the market prices at 80% when we have a 10% edge. “Life bankroll” refers to a combination of your finite time and resources.

To most, these numbers seem absolutely insane and it probably is. People willing to do this are generally regarded as insane and only retroactively lauded: Elon parlaying all his PayPal earnings into Tesla and Fred Smith playing blackjack to save FedEx from bankruptcy.

To be sure, I’m not advocating for these decisions, as there is massive survivorship bias here. Furthermore, there are practical limitations to directly applying Kelly to career decisions:

• Kelly assumes infinite future opportunities. Most opportunities in life are scarce and only available for a short period of time (job offers, university decisions, etc.).
• Kelly assumes independent bets, but career outcomes are highly correlated.
• Payouts are typically not defined or known in advance.
• You don’t know your edge. Worse, you may delude yourself for years thinking you have an edge when you don’t.

However, it is clear that if you are seeking outlier success, you will need to allocate a disproportionately large portion of your life bankroll relative to what most people’s intuitions suggest, increasing your variance and probability of outlier success. You can think of your career as a portfolio but any one position at a given point in time should be concentrated and high-conviction.

Generating Edge and Life Bankroll Bets

You are only able to generate outlier success when you have an edge. Most people either never develop an edge or waste it once they have it.

There are thousands of writers who write 1000 words per day on useless marketing copy, thousands of senior engineers pushing 1000 lines of code per day tweaking button sizes. Most will spend their life not really working, getting anesthetized, never expending any of their life bankroll.

The internet is one mechanism that enables you to develop an edge through quick feedback loops. Early achievements (high chess ELO, USTA ranking, League of Legends rating) are signals that (1) you have an aptitude for certain abilities and (2) you are capable of generating an edge.

Other forms of edge can also derive from increasing your skill set, which typically occurs as you get older, accrue more tacit knowledge, and gain a larger network. Most people don’t do the work over long time horizons – there is an edge to be had in every field by compounding long-term conscientious behavior.

Developing an edge is only half the battle. You’re probably not thinking hard enough about applying your edge. There are countless ways to make life bankroll bets:

• Write one of the most read tech blogs from Taipei instead of Silicon Valley, enabling a unique worldview and insight into Asian economies.
• Commit to making a marketing movie for Nike. Spend the entire budget flying around the world with a friend for 10 days to create an insanely viral YouTube video, then leverage that success to popularize a new content format called vlogging.
• Write a definitive critique of leading sleep research and leverage your network to start a parallel institution for funding New Science.
• Leave your cushy job and relocate your family from California to an abandoned island in Malaysia to start a new YC for dark talent (and maybe a new country).
• Take more flights. Relocate to a frontier hub for a few months when you're young, at high energy and at peak fluid intelligence. You might not have the financial capital, but you can often compensate by convincing benefactors, participating in fellowships, or raising VC money.

The Cost of Underbetting

When talking to mentors and people older than myself, they almost universally cite that they wish they had taken more risk. Often, this sense of regret manifests itself in leaving their previous job sooner, getting divorced earlier, or moving cities earlier.

This sentiment aligns with the universal takeaways from Kelly:

• People undervalue the cost of inaction (not moving cities, staying in bad relationships), wishing they had done it sooner or at all.
• Bet sizing scales with edge, not absolute opportunity size. Many people make the mistake of betting more on safer opportunities without considering their own edge.
• Care less what people think. You have worked to accrue context-specific edge, don’t let others talk you out of it.

Half the time I look back on my own decisions and cringe. But when I zoom out, the only choices I regret are the ones where I let fear or other people’s opinions shrink my bet size. The moments I went all-in still feel like the right calls.

Losing hurts less than never betting. Variance smooths out, regret doesn’t.