Taking a Break From Employment After 9 Years At Uber

Jan 15, 2025

Note: For the past couple of months since I’ve launched this Substack I’ve written very sporadically. Since I will soon be without a job, I want to try and make a more focused effort to publish more consistently in 2025. As part of that this will (hopefully) be the first of a series of posts to be written and published every two weeks. Thanks for reading!

All good things must eventually come to an end. This week I am leaving my position at Uber after just over 9 years at the company. The vast majority of my decade of professional experience has been at Uber and it will be a time that I look back on fondly. I had the privilege of working with some extremely smart and driven folks on a very unique team that gave me the opportunity to tackle some interesting problems at the intersection of tech, policy, economics, and transportation. I’m very proud of some of the projects I was able to contribute on which include:

Developing and implementing the initial methodology for calculating Uber’s “carbon intensity” which has been used in every edition of Uber’s climate reporting.
Collaborating with outside academics to study Uber’s impact on automobile fatalities that resulted in two papers published by researchers at UC Berkeley and UT Austin.
Assorted research on how Uber has provided additional transportation options across the US.
And finally, spending my last stint at Uber on the Marketplace Fairness team studying and working with product, legal, and policy to mitigate sources of discrimination on the platform.

In almost every way the job I had at Uber is, and was, a dream job. As someone who does a little recruiting every year I can somewhat confidently say that if I wanted to be employed full time, this is the team that I would want to work on. I was very privileged to be on a team where the people from ICs up to executive management were all incredible, work life balance was by any measure reasonable, and compensation has been great over the past few years.

So why leave? It is a question I have grappled with over the past couple of years. I think there are two related catalysts for not only leaving Uber, but potentially taking a long term stint away from full time employment:

I had a taste of the unemployed life through a one month paid sabbatical that Uber provided me in March of 2023. It differs, critically, from actual unemployment in that I was paid and vesting equity through that time period, was more or less guaranteed a job when I returned, and it had a defined end date. The sabbatical did give me a taste of what life could be like if I didn’t have full time work commitments. I distinctly remember after my sabbatical ended thinking “I’d like to have more of that please” and that impulse has only gotten stronger over time.
Over the years I’ve cultivated a few hobbies. Some of them are income generating and over time have become more and more viable to be “lifestyle businesses”. I don’t think any of them are going to make me life changing amounts of money, but enough to support my day to day expenses and allow me the freedom of not having to work for an employer.

So why now? I recently turned 32 and the next couple of decades should be a peak earnings period for people in my position. The thought of giving up a significant amount of compensation and career experience, especially when you project out the compounding interest of savings in a retirement account for the next 35 years, feels a little irresponsible. On the other hand, the early 30s are where I expect to be the most physically and mentally capable and I’d like to leverage that to see what I can achieve outside of a full time job.

It is also, obviously, an incredible position to be in which is something that can be hard to appreciate in the moment. I have found myself frustrated at times with feelings of being “trapped” and not able to structure my life the way I want to. It’s important to remind oneself that anyone who has a financially viable choice to indefinitely voluntarily leave full time employment should consider themselves very lucky. It’s also a reminder to those in that position that in the end you do, indeed, have a choice to actively make these types of changes in your life.

Below are some of the things that I thought about before making the decision to take at least a year off from full time employment. A lot of these things are idiosyncratic to my personal situation, but I hope that some of it might be useful to others contemplating doing something similar. I’ve broken it down into a few categories summarized here and in more detail below:

Financials: A very long runway built from a decade of employment invested into a massive bull market and lucking into lower than average housing costs in San Francisco.
Personal Life Situation: Just turned 32 in good health with no significant other nor other familial obligations. Strong desire to at the very least take a break from full time employment.
Outside Options: Poker, sports betting, and Twitch streaming plus other non-income generating hobbies. I’ve developed a foundation in a few income generating hobbies that I really enjoy and hope to effectively run those as a lifestyle business for as long as possible.

Financials

I am very grateful to have my current financial situation. This includes:

Graduating college with no debt in 2014 into an insane 0 interest rate job market and having continuous employment since then. Clearly the key to success is to choose to be born such that you coincide your entering the labor market during a generational bull market.
Choosing Uber as my second employer and staying for long enough to see significant appreciation of my stock based compensation since I joined and the additional refreshers issued from the rock bottom of the Covid days.
Purchasing an apartment in San Francisco at both historic lows for interest rates and a lull in San Francisco’s housing market during peak Covid in the fall of 2020.
Saving 50%+ of my post-tax income into an S&P 500 bull run that has appreciated by roughly 200% since I entered the workforce.

A decent amount of where I am at financially can be attributed to the timing of when I entered the workforce, picking the right company to work for, and never really having any debt both financially and otherwise. I’ve started from a pretty advantageous position and have been lucky to maintain that momentum throughout my career. That’s not to say I didn’t work very hard at times - certain 80 hour weeks in economic consulting come to mind - which helped set me up for financial success, but if you shifted when I entered the labor market a few years earlier in the middle of the housing financial crisis or a few years later in the post covid slump, my financial outcomes would have likely been far worse than they are today.

The toughest thing from a financial perspective to work through is the opportunity cost. An extra $100k in income and savings this year is worth roughly ~$320k in real terms after 30 years assuming a 4% annual inflation adjusted growth rate. That is… potentially a lot to give up, but, at least for me, once I’ve reached a certain level of financial stability the marginal dollar is worth a bit less and I am willing to give it up to see if I like striking it out on my own. What has also been a bit of a forcing function is the fact that the bulk of my equity issued when Uber stock was at rock bottom has vested and I am facing a compensation cliff this year which has made it a little easier to leave.

Overall I have a pretty long runway assuming modest annual expenses and my lifestyle not significantly changing. My goal is to see if I can make a version of “Coast FIRE” work. I have roughly enough saved that will grow into a retirement account once I hit retirement age, but need to cover living expenses until I get there.

Personal Life Situation

I am, for better or worse, a recently turned 32 year old who is not currently in a long term relationship nor has any family to care for. This makes it quite a bit easier for me to engage in a bit of risk taking and to be a bit “greedy” in what I want for myself. Is it possible that my life situation can change in the future? Absolutely. And that has been top of mind on the timing of leaving full time employment. I feel like I am in a somewhat unique era of my life where I don’t have any “real” responsibilities, am in reasonably good health, and have a bit of freedom to explore the “what ifs” which I may not be able to do later in life.

Taking this time off may also provide me with some much needed perspective. I wouldn’t exactly characterize myself as “burned out”, but over the years the excitement I’ve had for working has gradually diminished over time. My undergrad self would have been ecstatic if you told me that I would have the opportunity to do what I did at Uber, but a little bit of Covid lockdown dissociation and other factors has tempered my drive to work at any company. Again, there was not anything in particular about my job at Uber that resulted in this disinterest in work. If I ever feel motivated to be a W-2 employee again I think I would gladly go back to that team if they would have me. It was more of a mismatch between full time employment in general and the other ways I could be spending my time.

In any case, I’m hoping the next few months will provide me with a refresh such that if I choose to return to employment I’ll regain some of the excitement required to make the full time grind more fun. That or there’s a possibility that the self-employed lifestyle ends up working out as both personally enjoyable and financially viable such that I will not have to return to being an employee.

The Outside Options

The broader team I was on at Uber did a lot of labor economics adjacent work and a recurring theme in understanding how Uber’s contractors were compensated revolved around the idea of “the outside option” - that is the next best thing that one could be spending their time on. For most people who leave an employer their outside option is another employer.

For me, the outside options consist of a few income generating hobbies that I’ve invested in over the past few years. It also cannot be understated that part of the allure of turning my hobbies into self-employed work is the flexibility it commands. I will be dependent on these activities for money, however being your own boss and having the choice at any time to take a break or pivot to something else is something that I value.

Poker

As we went over in some detail in my first post on this Substack, poker can be an extremely profitable game with some insane swings. I am fairly confident in my abilities to be a winning player in most live tournaments and cash fields at the stakes I play and would like to be able to dedicate enough time and energy to put in enough volume to have the results match my abilities. It is also something that I currently also enjoy a lot even with its ups and downs having probably played a couple of hundred hours live over the past year. We shall see if that passion is still there after a few months of effectively playing full time.

Additionally there are a few reasons why I think the timing is good for playing full time. Overall poker has been undergoing somewhat of a mini-boom aided by all time highs in crypto markets. More money in the ecosystem means more opportunities for sharp players to profit. More specifically:

Live poker may be the softest it will ever be right now unless there’s another Chris Moneymaker level event or if there’s a broad legalization of online poker in the US. With the advent of solvers and proliferation of poker training sites, I think fields are on average only going to get tougher over time1 and now is a good time to chase tournament poker glory.
Online poker in the US may have an opportunity to grow. WPT is getting into the “sweeps” model of online poker with the release of their ClubWPT Gold site. If that survives legal scrutiny, it may be a great opportunity to get in a ton of online volume. There are also a number of crypto offerings that have come online which have the potential to draw more people into the game. Also, contrary to popular belief, online poker, especially tournament poker, is very much beatable right now if you know where to look.
I am personally most capable of physically and mentally playing right now. Sitting at a poker table for 10+ hours a day is extremely draining on body and mind. While there are older players performing at an extremely high level (see my favorite poker player David Stamm), I imagine my ability and will to play and study the game will only get worse over time.

The primary risk in playing poker is that I lose so much of my bankroll that I won’t be able to play the stakes I’d like to without getting a job. The nice thing about having a job in the first place as it relates to poker is that the bankroll is self replenishing and the guideline for bankroll management is “as long as it doesn’t affect your life finances”. The other “risk” is that I just end up hating playing as a primary source of income. Either way, these roads lead to just having to get a job again.

Sports Betting Syndicate

Over the past few months I’ve been dipping my toes into managing a sports betting syndicate. As we covered in my second post, there are opportunities for sharp bettors to profit from the current sports betting ecosystem in the United States. Forming a syndicate has allowed me to scale my strategies and being able to spend more time on managing this will improve potential earnings.

In terms of timing there are a couple of macro factors at work as well:

Sharp sports betting in the US will likely only get harder over time as books optimize their marketing promo spend and implement better strategies to kick sharp bettors off their platforms. From my experience right now, there are a lot of sports books in growth mode in the US and they are doing the bare minimum to limit sharp bettors while also providing very generous promotions for new users.
Access to sports betting on your mobile device turns out to be pretty bad for the average person. This study shows that having effective access to a casino in your pocket is absolutely detrimental to the average household in the US. There is a chance that sports betting becomes more restrictive in the coming years.

Thankfully the variance with sports betting is far smaller than poker even if the upside is a little more capped. This will probably be the most “work-like” thing I will have to manage post-employment. I wouldn’t say the day to day execution of the strategy is particularly satisfying, though it does provide me some happiness to beat the sportsbooks at their own game.

Similar to poker, if things go really wrong and the bankroll blows up then the worst case is I’ll just have to get a job again.

Twitch

I am very lucky to have built an audience on Twitch over the past couple of years. We achieved partner status in 2023 and this is something that I hope to continue growing by streaming more during my hiatus from full time employment. In the past the majority of my content has been sim racing, but there is an opportunity to also grow an audience streaming online poker.

In terms of timing I don’t think there is anything in particular that makes it a great time to stream right now. On a macro basis, total Twitch viewership peaked during the pandemic and has steadily been falling since. My expectations for Twitch streaming are that it is definitely still possible to build out your own community and niche, but getting the audience numbers to a self-sustaining “full time” level is very difficult. I currently average about 75 concurrent viewers a stream and financially this covers about 20% of my housing costs in San Francisco per month. Part of my time off will be spent streaming more and seeing if there’s a larger audience to be built.

In any case, the financial side is very much a bonus to me. Building any sort of audience on the internet is very difficult and requires a bit of luck. Being paid any amount of money to effectively play video games for an audience is still crazy to me and I’m forever grateful for the folks that watch and financially support the stream. It is simply very fun to do things with people that share similar interests.

What’s Next

I think the biggest takeaway I’ve had going through this process is to be thankful that I’ve had this choice in the first place and to be thankful for everyone who has enabled it. I’m thankful for my parents, their unconditional love, infinite patience, and who worked hard to put me through college debt free. I’m thankful for my brother who is responsible for getting me into poker in the first place and his coaching over the years. I’m thankful for my friends both new and old who have been supportive and provided me with many years of companionship. I’m thankful for my colleagues and bosses who have taught me a lot and grateful for their good humor even in times of crisis. And finally I’m grateful to everyone who has directly or indirectly supported my hobbies. From the poker friends who have been an invaluable sounding board for refining strategies, my partners who have helped make the sports betting syndicate a reality, anyone who has ever dropped by the Twitch streams (especially the regulars rudiscL), the very musically talented folks that I’ve performed or recorded music with, and anyone who’s ever read or reviewed anything I’ve written – I’m eternally grateful for you all showing me that there is more to life than work.

My final day at Uber is on Friday 1/17. If you are interested in my role, the backfill job posting can be found here. Once again, I cannot recommend the team enough if you’re looking to work with a group of brilliant economists and researchers on issues of algorithmic fairness at a company that has a wide breadth of challenging problems to tackle. Happy to answer any questions as a soon-to-be ex-employee.

There are a number of other things that I’ll be spending my newly found extra time on. I’d like to get into better physical shape, make more music, do more concert photography, write more, and spend more time with close friends and family. The first two months or so of my unemployed life will be spent traveling around the US following the poker tournament circuit. Afterwards I hope to settle into a bit of a rhythm streaming and hopefully making the most of my time off.

This, now perhaps inaccurately named, Substack will serve as a place for me to collect my thoughts and share any experiences that may be of interest to a broader audience. If you have made it this far, once again thank you for reading!

By “over time” I mean over a decades long time frame. The pool of recreational players, at least in the United States in person fields, is still pretty large and it will take a while before that player pool significantly shrinks.