Finance Sabbatical / Career Change

Gonna probably call it quits soon a handful of years into my IB career. I’ve saved enough money and been lucky to make a bunch in the market where I can support my lifestyle and travel for at least 2-3 years before having to think about the next step. 
 

After this job, I’m sure that I want to exit finance industry. Wife works in tech and her lifestyle is unreal (good cash too). Tech is attractive to me.


Has anyone had experience with a long travel sabbatical followed by a career change? How was it? Business school is off the table. 
 

Thanks.
 

 

Following, might also be semi-retiring from traditional finance soon.

 

I think traveling is good - it might give you time and space to clear your mind. I’d recommend a tiny moleskin book to carry with you to jot some ideas down.

You have the rest of your life in front of you - find out what you’re passionate about - this should be in your mind while you’re on the journey.

Also, the feeling of leaving the corporate world and starting your own new path is the best feeling in the world. Embrace the excitement of new beginnings. Have fun. Good luck.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee
 

Thanks bud. I can't possibly imagine what I would do for a living after this period of post finance floating. If it ends up being working for someone else, it would almost 100% have to be for a super early-stage startup that gives me complete flexibility over my life and time. Of course would happily take the trade off in pay.

 

Dude, nice job with the trading wins. I took a sabbatical after leaving PE but definitely not as long as you are thinking (6 months). I had a lot of fun wake and baking whenever I wanted to, traveling, and working on some side hustles, but there were definitely a couple drawbacks. 

1. No one else is free. You should do some planning ahead, be it with your wife or other buddies, cause otherwise you're going to be doing a lot of shit alone since everyone else has jobs and is working. 

2. You have to tailor the length of your sabbatical to what you wanna do after. Like if you want to re-enter the corporate world, anything less than a year is probably fine, but I think you are going to run into some obstacles if you're talking 2-3 years. Obviously if you're going to do something else then it's not as important. 

 

Thanks, this is helpful. Not so concerned about #1 -- my wife knows that it's been something of a dream of mine to travel the world immersively (as opposed to a week here, a week there) and her job is fully remote indefinitely. 

#2 is the real issue here. I have no fucking clue what I want to do after. Finance was always the carrot on the stick because of the financial security it offers, but I think given how much I've saved at a relatively young age, after the time off, the prime motivator for what direction I decide to take in life won't be driven by concerns over financial security. I think leisure, lifestyle and enjoying my work would be most important to me. That is why it seems that a flexible early stage startup would be the ideal fit for me.

 

Maybe you can set checkpoints every few months to re-evaluate and take stock of your options. Might also just have a good cadence of convos with people in interesting jobs to you. 

One note on early stage startups if you are looking for work / life balance - depending on how early stage we're talking (and role, to some extent), you may find yourself on the wrong side of the work/life balance equation. 

 
Most Helpful

You have achieved financial independence. Congratulations. It's impressive, and I want to tell you it will also be kind of isolating. 

No one in your current life is going to relate to you much from here on out. Their life circumstances mirror yours in no way any longer. Always keep that at the front of your mind. Advice you get, reactions you receive, all need to be viewed through a lens of 'how relevant is this to me.'

There is no playbook given to you when you make money at a young age. 

What's interesting in reading your comments is how you haven't really wrapped your arms yet around your independence. You don't need to ever plug into someone else's system again. I would focus less on a job that gives you the lifestyle you want and more on what things interest you enough to warrant your attention.

There are so many fascinating things happening in the world today that you could (and I argue should) do nothing other than follow your natural curiosity to whatever topics are most interesting, develop a basic knowledge base, begin speaking to the best people you can meet related to those topics, and begin putting your money to work around them.

This can take so, so many forms. If you think the future of finance is one where democratization creates sweeping changes in how markets function and assets are held, you could travel the world indefinitely while beginning to dedicate your time to that. Read the entire blogging history of the fintech-focused venture investors on the Midas List. Look up the hundreds of portfolio companies between them. Watch and read every interview with those founders. Play the LinkedIn and Twitter game of finding common connections with people who have or still work at those companies. Ask about their business model, roadblocks, strategy, team, culture, product philosophy, ugly problems.

You'll know it when you feel it. There will be one or more you feel really excited about. Write a check. $50k, $250k, whatever. You might have to do that via a secondary. You'll probably have to convince the founder(s) to let you write an angel check alongside whatever next financing they do. It's possible to convince them to just take a SAFE so you don't have to wait on the round happening.

There are limitless other paths. Life sciences, hard sciences (medical devices, foods, space exploration), engineering (robotics, IoT), consumer (brands, products), education, data ... anything that interests you is something that you can apply the same formula to.

You could try a different formula. Instead of investing, acquiring. You can find a business that fits your interests well enough to own. If the check required is larger than you're able to write, you can speak to other people to get them to join you. That might be another financially independent person. It might be a decision-maker at a place that is in the business of writing checks. In either case, it's up to you to decide whether to give them a free ride in the thing you want to run or to charge them. If the latter, put together some kind of performance fee. 

I get the appeal of the flexibility, but beyond that, why would you want a job at a super early stage startup? You answer to someone else. If you took a little more expansive an approach to the diligence you'd do on deciding whether to work at one, you could create a comfort level with investing in one. At that point, your 'job' is undefined and limitless; it's about creating and delivering value on behalf of the company you're now financially motivated to care about.

Now you need to decide what to do with your principal while you're still searching and studying how to deploy it. You've proven to be remarkably successful in the public markets. Continue that. Or de-risk by moving to a non-concentrated approach (your own) or product (someone else's). 

Your time is now your most valuable asset. There is zero, literally zero reason to take a 'job' somewhere. You have given yourself your first footing. You accomplished that while plugged into an 80-hour workweek. Imagine what you can do with full control over your time.

This circles back to how I began.

You're thinking of taking 2-3 years, then going back to work. I want to tell you you'll likely be a bit unfulfilled.

The people you want to catch up with will cancel or push last-minute. The ones who don't cancel will be late, or they'll be distracted on the call, or they'll have to leave early. Makes sense, they're still in the 80-hour seat.

When you interrupt your day in the sun on the beach, finish your workout a bit faster than you otherwise would, interrupt the book you're engrossed in, or whatever, you feel way less happy when someone disrespects your time like that. If your alternative is to click back into your inbox or open the file back up, who cares if someone missed the thing. When your time is yours alone, it's different.

A much healthier model is to work one-quarter as much as you used to, and do it forever. If you find something really engrossing, you'll naturally get drawn into it. The cool thing is that you don't have to if you don't want to. Sometimes you'll have to remind yourself of that. If you're a driven person, it's easy to overtax yourself. 

Find what works for you. It's entirely possible to travel for extended periods of time, be productive with reading and conversations with relevant people, and devise actions that produce meaningful financial returns on any money you decide to put to work.

Good luck. I'm really happy for you. 

I am permanently behind on PMs, it's not personal.
 

Interest viewpoints, great comment. Only thing I wonder, is 2-3m is enough for such an adventure? Reason I am asking is 2-3m is definitely an achievable goal, albeit on a longer timescale for most. So trying to gauge how relevant this reply is to people falling in the bucket “will likely have 1m+ in several years”. Thanks.

 

Following. Absolutely incredible story. Most valuable commodity in this world is time. Going into my 3rd year of IB and feel like this story is the ultimate goal. Make enough to do whatever you want.

Curious to hear your investment process and how much due diligence you did to have comfort with such a concentrated position. Thanks!

 

Going to slow you down for a minute: can I ask what you mean by travel/what you plan to do during the interim? 

I'm in a somewhat similar position to you and about to transition from banking to YOLO my mid twenties. After thinking about it a lot myself, what you come back to do as well as who you come back with/as will be wholly dependent on your next two or three years. In fact, those years will probably dictate how fulfilling the rest of your life will be.

For context, I plan on pursuing an interest that I've had since middle school. It's nothing crazy, but it will lead to a new life in a new place for a couple of years. Even if this blows up in face, I would regret never doing it. 

Would love to know what your plan is. But, in any case, congrats.

 

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