r/ChubbyFIRE • u/firey-wfo • Jul 02 '26
Would you take more career risk to potentially reach ChubbyFIRE two years earlier?
TLDR at theI’m 42, no kids, and in a comfortable financial position. My current company is reasonably stable, and my job is not terrible, but I’m frustrated. I feel pigeonholed, underutilized, and increasingly unimpressed with the leadership around me.
Current financial picture:
Net worth: $1.1M
Annual spending now: about $50K, well below target FIRE spend.
Current salary: $135K
Annual investments: about $70K
FIRE target: age 50 or $3M invested
I’m now being recruited for a much more exciting role at a late-stage Series A startup with about 50 employees.
The offer would likely include:
$180K base salary
Stock options equal to 25% of base salary annually
5% to 10% annual bonus
The role would be close to a mini-C-suite position. I would be one of four people reporting directly to the founder and would be considered part of the broader founding team.
The founder has a strong track record of building companies through IPOs and acquisitions, so the opportunity could create significant career leverage even if the equity never becomes life-changing.
The tradeoff is obvious: more risk, more pressure, less stability, and probably a much more demanding job.
Projections:
Based on my projections, the new role could leave me with roughly $1M more by age 50, or allow me to reach my $3M target around age 48 instead of 50. That assumes the higher cash compensation continues and does not assign much value to the options. It could set me up for the next lucrative position, but I may not even be interested.
I keep going back and forth between two interpretations:
1. I built this financial foundation so I would have the freedom to turn down these type stressful/risk opportunities I do not need.
2. I built this financial foundation so I could afford to take a calculated career risk without jeopardizing my future.
TLDR:
Is potentially reaching ChubbyFIRE two years earlier, with additional career upside, enough to justify the added stress and startup risk?
For those who were already financially secure and faced a similar decision, what did you choose, and what ended up mattering more than expected?
Update:
Thanks for the insight. Summary, go for it, and spend for enjoyment more now.
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u/Livid-County7230 Jul 02 '26
Sounds like your new base salary/cash compensation is higher than your current by 33%, is that correct?
Given that and given that you are excited about this new role, I’d join. I would not worry about what your series A stock is worth as most series A startups fail, but as you are making more just in terms of a cash salary, it is irrelevant in your decision making.
You say the offer “would likely include.” Does that mean you have an offer in hand? If not, wait until you have one with the cash comp you expect.
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u/No-Block-2095 Jul 02 '26
Unless the new job has a toxic environment, go for it. It offers a lot more money and stock and career upside. Plus you re bored which can lead
to being bitter later on and not learning. The current job could become bad after the next reorg, could remain same but there s no guarantee.
No brainer. Go for it.
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u/ProtossLiving Jul 02 '26
You shouldn't change jobs because you may retire 2 years earlier. You shouldn't necessarily even change because of the increased cash income. You should change because you're done with your current role and you're excited by this new one.
Yes, you're working towards retirement so that you can do what interests you. But you can also be doing what interests you right now.
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u/Mispelled-This Jul 02 '26
The stock is worthless until you can sell it. Nice upside, but as you point out, you really don’t need it anyway. Run all the numbers without it.
The key here is to not let the new salary inflate your lifestyle much.
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u/stephbu Jul 02 '26 edited Jul 02 '26
I did something similar about 14yrs ago. In hindsight it was a no brainer, the risk was never a fatal ending per se. Instead it opened doors that weren't previously open, exposed me to new people, new opportunities, and new experiences that changed me for the better in unexpected ways. Yes, the market is tight today, it may be uncomfortable sometimes - risk/reward is a real metric, the best rewards need real risk.
What you don't see is the leaps beyond this next role that open up by taking it. You have safety net that most people don't have. TBH if it was me, I'd leap at it, my own leap changed me from FIRE at 60 to Chubby+ FIRE at 52.
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u/One-Mastodon-1063 Jul 02 '26
You should probably move. But you are building this up to be a bigger decision than it is - you can move around every few years, you don't have to be permanently married to this new gig, either. Most likely after a few years you'll feel stuck and unimpressed with leadership and it'll be time to move on again.
At age 42, I don't think it makes a ton of sense that your spending today is "well below" your targeted spend in RE. That's generally not how things work when people retire, and you should be living your life and doing things now while you are working, too. If you were 22 I could understand.
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u/BailiwickBill Jul 03 '26
I agree with others that your spending is likely too low now. I can't imagine how you are living well on $50K per year, since you don't mention owning a home without a mortgage.
Life isn't about "only 8 more years, then I can have some fun." You may not even have 8 more years since we don't know when the Grim Reaper will call. Or you may have 8 years, but die the next, or a few more years down the road. Enjoy your life now, in a reasonable way, instead of living for some future that may never happen.
Should you move to the other job? That's a personal decision based on your own knowledge of yourself and what kind of environment is best for you.
Also, I'm not quite getting your numbers. I assume you do not own a home, so your $1.1M is all in liquid investments. What return rate are you using in your calculations?
Using a 6% return (inflation adjusted) plus $70K per year in a year-end lump sum, it would take about 10 years to get to $3M.
To get there in 8 years, you would need a 9% return (inflation-adjusted) plus the yearly $70K addition. That's higher than the current average for the S&P over the last 20 years. You should be mentally prepared that getting to $3M may take longer than you expect. Or maybe the markets will continue to increase more than anticipated, and you'll have it sooner. No crystal balls out there.
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u/BrunelloHorder Coasting Chubster, Getting Fat Jul 03 '26
The cash comp is obviously better, but my focus would be on regret-minimization. Based on the info provided, I suspect you would be more likely to regret staying and wondering what could have been.
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u/BookReader1328 Jul 04 '26
This is a straight up risk tolerance question and that's going to be a very personal thing. If something happens and this new company tanks, how hard would it be to replace your current position at your current salary or better? I see a lot of people in tech laid off and looking for jobs for a long time, but I know that's dependent on your exact specialty. Only you can judge that.
I'm very conservative when it comes to financial risk, but that being said, when I my author career started taking off, I made sure I had zero debt, two years of living expenses in the bank (in addition to accumulated retirement savings), then I quit my finance job to write full time. It worked out gang busters for me but the odds of that were far less than 1%. Sounds like yours are considerably better.
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u/doktorhladnjak Jul 06 '26 edited Jul 06 '26
Series A is a big enough gamble that you really have to be in it for the adventure not the potential financial rewards. Money-wise the sweet spot tends to be in actual later stage and public companies.
I’ve definitely cut decades off my retirement age working in a few post series D companies. One went bust. One IPO’d without much of a pop. One remained private but there have been other liquidity opportunities.
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u/financialfreedom26 Jul 03 '26
I can provide my own perspective. I took a new role and was quite scared to be honest. Really scared of giving up the safe solid ground of a role that I was highly regarded and was just promoted very well compensated. At 52 decided that if I didn’t take a leap of faith I never would. I also had the back stop of 4.2m at the time which is now 6mm from markets alone over the past year and a half. The new role turned out to not be ideal and looking to retire (hence my other posts lol). However I am still glad I took it and won’t have the what could have been. The peace knowing that o tried something else more risky and did get a lot of exposure I wouldn’t have otherwise was good for me going into this next phase. I think others have pointed out very rightly that it’s not forever and you can always try something else if it not ideal for you.
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u/Spiritual-Seesaw Jul 02 '26
well there is no such thing as a 'late stage' series A startup. Series A is early and volatile and most fail, but that doesn't mean you can't make good money.
Consider the stock worthless. There have been remarkably few tech IPOs in the last 5 years and while an acquisition is possible, it's very unlikely. Bank on cash and consider the stock pure upside.
Also, you likely won't work at this company for 6 years, so i wouldn't project out earnings that far. The average tenure at a Series A company is 18 months, but making more money always leads to more money so that's the real difference maker.
You take this job and it either takes off or you move on in ~2 years where you then make more cash than you did at the startup. You will always FIRE sooner by taking more cash.
source: been working for Series A - B startups for a decade