Quitting and skibum it?

Has anyone considered quitting the rat race and taking up an easy remote or skibum type job? I feel very fortunate to make the money I do and am pretty sure I won't be able to get back on the horse once I quit, but it doesn't fulfil me (although I do like parts of it and I happen to be pretty good at it), I don't like the hours and frankly I don't care about money as a goal. I care about money because I like the (idea of) freedom that it buys and I'm uninterested in material possessions (shocker). I've been in finance for about 5 years and slowly going grey at this rate. It feels like a waste to slave away on deals for the next 5-10 years while I'm still young

I have low single digit carry vested (assuming the new cost of debt doesn't destroy valuations / we do get to 2x MoM somehow) and I'm expecting a mid single digit allocation in the next 12-18 months. I'm considering working until this is partially vested (maybe 50%) and then throwing the hat in the ring. I won't be rich, but I will be able to spend my late 20s / early 30s as a skibum in winter and lifeguard in summer (or something like that - or maybe a freelance consultant or whatever, let me know if you have ideas). I'm not from a rich family so I'm entirely on my own and have no safety nets or secret stashes of money awaiting me

I feel like if I don't do it now then I'll be mid-30s, at which point you'll probably want to settle down, have a kid and be tied up for another 18 years - at which point you might as well just keep at it in a corporate job. And most of my 20s is already gone

General open discussion, but to start off: has anyone done this and did it work out / are you happy? If it didn't work out were you able to get back on the wagon? Am I crazy to consider foregoing an exponential earnings ramp I've sacrificed a lot for? Are you comfortable betting your carry will hit (even the current covid vintage) so you have some sort of nest egg? Sorry for the ramble. Any input much appreciated as obviously this is a pretty career limiting thought and can't really discuss it elsewhere

 

Being a ski bum is an attractive lifestyle for early 20s, but it’ll get old. your money will burn down and if working a normal ski bum job it’ll only just get you by in this day and age. That’s cool for a few years but as you get older and your priorities will change and if you want a family you’ll need money. Maybe look into buying/starting a business in a ski town or getting a remote job 

 

Thanks. To clarify - the point is not so much specifically being a ski bum but more so switching from PE to a low/no stress, fun job. Whether that’s being a skiing instructor, boat driver in summer, or even ‘digital nomad’ / freelance consultant for a couple months a year, you name it matters less

 

I think the spirit of the response was right though; that is, a low / no-stress fun job might become old within a few years, however green the grass looks now. A potentially very happy medium could be to do something a little entrepreneurial like buying a business in a ski town which would keep you engaged mentally.

One of the risks here is that after many years of banking / PE, you're very accustomed to a faster pace of life with frequent challenges and stimulus, and moving to something so different could leave you feeling disengaged or bored. The other risk is leaving yourself exposed if your priorities do change towards, say, having your own family, and your new role in a fun job doesn't leave you equipped to support kids.

If you're feeling this way though, something might need to change. Maybe you could look into a sabbatical if that's something your firm would accommodate? Otherwise you could just resign, live out the lifestyle a year or so, and then think about what next (curious as to why you're so negative about your ability to come back to PE) - I know people who have done / are doing this.

 

Fully advisable for a period of your life. 

Used to work at MF and quit pretty early in my career - have managed to make a good living while actually enjoying life. 

 

Travel as much as I can and spend quality time with friends. Consult a variety of private businesses on strategic decisions on an hourly basis to cover expenses.

I think you figure it out as you go along given you have the motivation and pre-req skills which considering your background, I would assume that you do. 

 

Thank you, very helpful. Some questions if you don't mind: at what age / seniority did you do it? Any regrets? Do you travel around and work from there and what do you do with your housing in your 'hub' (if you have one)? How much can you reasonably make per month? 

 

I never tried what you are describing but I’m in my late 30’s with a family so will give opinions based on that. 

The first thing is that it doesn’t sound like you are happy in your job and that’s a big thing. You don’t have to love every minute of it, but if it doesn’t get you excited then it’ll probably be a grind for a long time. It also seems like it is impacting your overall happiness (probably because the job is so many hours) and my worry would be that you are equating more time/different job with more happiness and that may not be the case. There are many people I’ve met who are retired or have a lot of free time who just don’t know what to do with it. Do you feel confident that the ski bum (or similar) life is what you want? Have you tried it for a month (take a sabbatical or extended vacation?). 

I’ve also met many people who put unreasonable expectations on their work hours, and rather than “work smart” and take time off when they want/need it, will always be online, always working, always stressing. I’m mostly pointing out that some of this might be self imposed, when I was relatively junior in finance I took a lot of time for myself and it wasn’t an issue as long as I performed  

The other thing I’d ask is what you want your life to be like in your 30’s and 40’s. Do you want a partner? Children? What do you want their lives to be like? Will it work with this lifestyle or not? Not giving a view one way or the other, just asking you to think down the line. 

And finally, as someone who is almost 40 with a family, you aren’t tied down or anything like it during this time. As long as you can advocate for your time off, the financial freedom a career can give you actually let’s you enjoy a lot of the time the same way you could when you didn’t have a family. 

 

Thank you, very helpful. I think a sabbatical would be a good idea. Or I can quit, get a new fund / job lined up and then negotiate a very late start date - if I like the lifestyle I'll just not show up for the job, big deal. One of these is probably the way to go. A sabbatical will probably hurt my career significantly so might as well pack up my bags altogether potentially

On the hours, noted but to be honest I think I've already optimized that. Frankly I work fewer hours than peers as I'm pretty comfortable taking shortcuts. Unfortunately despite that I'm at a place with a serious amount of face time (even when off deals) and a total meatgrinder during deal time. Most of my friends have the same experience or worse (large cap)

Appreciate the points around kids etc. but frankly I'm not sure I want them (and probably not in the next 5 years minimum if not longer. I'm pretty comfortable on male fertility being able to hold out long enough should I want to pull the trigger at some point - realize you need a counterparty for that but that's a seperate discussion

 

Why not do an MBA? It won’t fully give you the same amount of free time as going full ski bum (or whatever), but you’ll have a lot more flexibility for travel over breaks (and long weekends depending on the program). The cost is high, but you’ll still have the option to stay “on track” if you do end up deciding that you want to stay in finance, even if it’s in a role with more manageable hours.

 

I don't think I'd enjoy it and it'd require me to go back to the grind. I don't have enough money to just pay for it and then decide to hang up the cleats if I like the lifestyle

 

I've always thought of my nuclear option as being a jet-ski tour guide in any one of St. Maarten / Turks & Caicos / Anguilla etc and the types for whatever it's worth. So I definitely sympathize with the thought of quitting the rat race and doing just that as it sounds super fun. But then I go to these places and actually go on the jet-ski tours or the yacht charters and I'm always thankful that I am ending it and that I'm "going back to reality" as it were. I found it's easy to fantasize about leaving the industry but as someone who actually likes my job and enjoys the fact that I'm able to afford doing what my escapism option is for fun, it helps bring me back to the reality that I want to keep working as I am, with a small part of that derived from the fact that I can have fun that way. 

This may not fit you but as someone who is extremely career driven, obviously my answer may differ from yours but just food for thought! 

 
Most Helpful

Fun topic! So I had many of the same dreams as you did when I was in my 20s and contemplated the various different pros/cons of exiting the rat race early, moving to a low cost of living area, and enjoying life rather than grinding away at PE. I finally pulled the ripcord when I was 35 and felt like I had enough savings to live my desired life without the need for the supplemental income / remote job. Some thoughts now that I am over a year into it:

1 - Freedom is glorious. It is every bit as glorious as you are probably imagining it to be. Not having to wake up and go into the office every day, not having to be anywhere in particular on any particular day is liberating. You can make any plans that you want and 100% keep them without fear of something coming up at work. You can participate in activities without the mental weight of having to prepare for a meeting, respond to a meeting, or anything else. You can truly focus on living in the moment and disconnect from everything else without fear. This is the most valuable part of unplugging from the rat race. However, this sort of freedom is only achieved if you go independent and don’t take up another job (ski instructor is won’t check this box, but something similar to my career guidance consulting does).

2 - You need to be very comfortable being independent and alone. When I was still living in London full-time but not working, all of my friends had demanding full-time jobs. They weren’t available during business hours except when they were working from home and wanted to grab a coffee. Your “9-5” is very likely to be spent by yourself and your social activities will still be evenings and weekends. Even when I left London for Sardinia (Italy) where almost no one had an office job, people still worked during daylight hours. You need to carve out exceptions (such as I befriended a teacher in his 50s (guessing here) who wasn’t working during the summer, so we would play ping pong on Wednesday mornings for literally three hours. I was also able to do day trips to the beach, go hiking, etc. with people who had taken the day off work, but this was the exception rather than the norm. If you aren’t retired and actually have a job, try to find something that can be done on regular business hours.

3 - I had the same mentality of ‘I want to experience the best parts of life while I’m still young.’ The good news is that even late 30s is still young, and I’m guessing my 40s will be fantastic as well. If you take care of your body, you’ll be fully capable of doing all the active things in life well into your 40s. I played on multiple soccer (football / calcio) teams when I was in London, Italy, and at the moment Florida. Don’t feel you MUST do this in your 20s because it is still great as you get older — the key is to make sure you maintain your fitness. It’s a whole other topic, but being physically fit / attractive will also make it easier to move to a new city, make friends, and be invited to participate in activities. You also need to be a bit extroverted, or in my case, be introverted but have the ability to ‘turn on’ the social skills as needed.

4 - I know you don’t want kids (I don’t either) and aren’t looking for a partner, but a few things to note here. I’ll be making huge generalizations so don’t take these as a hard and fast rules: (1) You will no longer be appealing to women who enjoy fine dining, cocktails, designer anything, or ‘reputation.’ You cannot provide any of these things. As you don’t care about material things, you probably don’t want a woman with these characteristics, but just know that this group of women who most likely love you right now will lose interest. (2) You’ll be significantly more appealing to the creative types who don’t care so much for a high class life, but you’ll need to win them over with your charm because the ‘big time career and cash’ are no longer there. I hope you have confidence in your personality and are an interesting person (only kinda joking here). All this said, attracting women shouldn’t really be a concern if you go down this path and you are probably more likely to find someone who is aligned with your same values.

5 - Money matters and return on time invested matters. Even if you’re doing something you absolutely love (as a digital nomad), work is still work. There will be days that you didn’t sleep well and while you can probably take a nap at your leisure, at some point you need to put in the hours. One of the hardest things to overcome is the thought that you’re making so much less money for your time. When I retired, I was making multiple millions annually (at a much better tax rate). If I had worked one additional year in PE, it would equate to my working for 20 years doing my current career consulting. The only thing that gets me comfortable with this dynamic is the fact that I feel I have enough money and that my career consulting business is truly optional (and I’m only doing it part-time, so it doesn’t hinder other aspects of my life).

6 - If you were to quit now, I think you would have to go with the digital nomad approach rather than the ski bum approach because I think you still need the cash. However, working as a digital nomad only gives you geographic flexibility, but not all the freedoms that I think you desire. Realistically, I think you don’t have enough experience to truly go the independent consulting route. No company that can afford to pay you well is going to want a former junior finance guy on their board of directors and you don’t have any great differentiators. I’m not saying it is impossible, but I was speaking to a McKinsey friend of mine last week who said that the MBB people who quit to become consultants often struggle to secure clients because they lack any type of differentiation / specific knowledge.

I’m going to stop there because I could easily go on to bullet 100 with various musings about lifestyle, mentality, tax implications, risk, etc. Distilling this all into a conclusion: Don’t quit yet, wait until you have a lot more realized carry and treat the unrealized carry as upside. A few more years of grinding could eliminate 1-2 decades of working and there is a HUGE difference between being semi-retired and being a digital nomad.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

How did your first year out coinciding with a down market impact you, if at all? Where have your parked your wealth - what % in stocks, bonds, privates, paper income not yet paid etc.? One of my fears of quitting early (again assuming no partner and kids, as that will significantly increase the number), is market fluctuations if the nest egg isn't big enough. For someone in mid-30s that didn't get the carry you did, or let's just say for people broadly (not even in PE), what do you think is the minimum number to walk w/o stress while living the kind of lifestyle you are? 

 

I went into 2022 expecting the market to go south. As a result, I started dollar-cost-averaging into the market, but very very cautiously — at the most heavily invested point my liquid assets were 80% cash and maybe 20% stocks. I tended to throw more money in when the market dipped and from time to time pulled out some cash. Fortunately, I took a hit during the early summer but managed to sell off most everything when it rebounded in August. The only thing I have remaining is a few insurance stocks that are up a good 25 - 40% (i haven’t checked in a few weeks). I had some major wins (H&R Block was up 95% at one point, but I think I sold it at +80% or so) — but overall I ended the year up … was only slightly on my total net worth, but was up about 5% on the amount that I actually invested into the market. Given how tough the year was overall, I’m considering it a huge win to have not lost money. My strategy is to wait (hope?) that the market continues to collapse in 2023 and I can start dollar cost averaging into the market when I feel that we are nearing a bottom. I don’t have a specific number in mind, it will be more about the general state of the economy and whatever else is going on in the world at that point. I don’t need to time it perfectly, but it would be painful to take a big hit to my life savings literally the first couple of years after retiring (google Sequence of Return Risk).

In terms of where I’ve parked my wealth, right now I own a condo, have unrealized carry, and the rest is cash / 401(k). My plan is to sell the condo (mortgage is paid off, i rent it at the moment) and go pretty much 100% into a self-selected diversified portfolio of stocks. Likely will be a few years before I get to this steady state.

In terms of minimum walkaway number without stress? It is SO dependent on the person and their lifestyle. I’m also now supplementing my lifestyle with my career consulting business (which is admittedly a pittance, but it helps me avoid drawing down principle). I think having at least $5.0m is a pretty good floor unless you are single and very frugal. If you go as high as $10m you’ve probably eliminated any stress or risk of Sequence of Return Risk ruining your retirement. Remember, time value of money works both ways — having that big a nest egg early in your career creates some unreal opportunities in terms of compounding. I’m only counting on a 2-3% annual return on my investments, which is unreasonably conservative.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

Incredibly useful. I’ve read this a few times now over the last days. It has also motivated me to put an excel together with a pretty detailed and more conservative cash need overview. (Sadly) you are right and I’ll need more money. I need to have a very serious think about the return on time. It seems indeed that c.35 should be doable if I stay the course. I’m not sure if I want to do that but let’s see. The other important thing is to see how carry will materialise - in my current forecast if one of the funds disappoints it’d be annoying but not devastating, if it’s a donut im toast and if it outperforms it materially drags things forward. I assume you were in an outperforming or high velocity fund (whereas mine is quite slow but steady and low risk…)

If you don’t mind I might message you next week when I’m less busy with a few slightly more personal questions 

Thanks again

 

Glad to hear you found it useful. In terms of your questions, I was fortunate enough to have a good allocation of carry through multiple funds, each of which performed well. I did better by most people who were 35, but will never come close to the people who stick it out in PE. Part of what made it possible is that my funds went into the carry rather quickly, so I didn’t have as much uncertainty about future performance as most people face.

If you have more questions, I’d generally prefer them to be asked on the forums because that way everyone can benefit from my responses. If you are looking for something super bespoke / customized to your situation, I’m mostly handling those requests through my consulting platform on a paid basis nowadays. Annoyingly, I just scheduled a $350 initial doctor visit for a soccer injury. I’m self-insuring for healthcare at the moment (I don’t recommend this) and I’m now getting a real life lesson on why one should make sure to conservatively estimate healthcare expenses in their retirement calculator. :)

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

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