u/firey-wfo

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.

Should I quit my comfortable job for a high risk startup? I’m currently a PM in the defense industry with a technical background. Currently with @ $135k/yr in a low cost of living area. My current company is going through a lot of spin and leadership shifts. Have the ifnancials are great and support the other struggling half. My position is in high demand. I’ve been there 1 year and have seen 3 bosses and now absentee leadership. A new pmo organization that only exist on. Paper. I have an opportunity that will require a move from the mtns to Florida at a similar col. Salary would be $180-$200 base plus $45k stock options at a start up reporting to the founder. I’m really excited about the opportunity, but it is a high risk high reward. Currently I have a lifestyle spend of about $50k and about $1.1 in assets with a FIRe target of ~$2.5m -$3m. Which I should reach in 3-8 years. The math for this opportunity barely moves the needle for investment timelines. Is it worth it to take the risk of this opportunity?

There are massive cultural differences that I’ll face. My partner may not come and it could’ve the break the relationship needs.

I’ve been windsurfing for years and just recently hit a breakthrough in skills. Lots of sub planing short boarding slogging and practicing skills. I had an 2000 era sporty freeride 150. I recently upgraded to a modern 130 volar. Night and day sudden jump in skill progression.

Me ~190 dry and fit~ish 5’11”

Skills: confidently planing, in the straps and harness, pumping onto plane, riding wind and nasty chop to a ~4.2 as comfortable as possible in a nasty rodeo, little chop hops on waves, confidently water starting everything from a 9.5 cammed to a 3.2 wave on a 93 wave( was a little underpowered and didn’t get the drive for the 93), entering gybes planing with a little carve but loosing plane through the gybe (no longer rodeo weight transferred in the middle of the gybe), gybes stay smooth and consistent, confident with foot pressure steering and sail rig, able to feel the fin load up/ unload as it cuts through swell, limited straight blasting and slogging on some old narrow (57) b&J boards

My local spot is an inland desert lake; it’s either light and drifty or strong and gusty. No breaking waves. Lots of mixed chop and poorly structured wind swell that gets up to 4 ft.

My goal is progressing and ability to handle the chop at high speed while carve, gybe, jump (just straight air), swivel through the swell while planing, gybe off the swell. If I was in a location with better wind/water I would push progression on the volar. However this fits a difficult spot in the kit, the volar hunts for puffs early, then wind picks up, chop comes up and the volar can become a rodeo. I’m thinking of a 115 dyno . Open to inputs.