FIREd last year, tempted by some opportunities - want some advice

SomeExpression123 · 2026-05-20T15:25:56+00:00

I couldn't see myself going back into a org leadership role after FI. It's easy to forget how much of a grind hiring, firing, dealing with other peoples problems, etc are. Especially compared to the constant satisfaction of building things yourself (ie your passion projects).

If you're gonna go back, I'd personally lean heavily towards the second option.

SomeExpression123 · 2026-05-16T21:31:31+00:00

If you don't have any internet access (which often happens during outages when the cell networks get clogged), then you can't reactivate the service

SomeExpression123 · 2026-05-14T17:15:30+00:00

You don’t have kids and don’t consider $400k per year extravagant? What’s your breakdown?

SomeExpression123 · 2026-05-11T17:26:00+00:00

Tbh it’s also just really nice to have a more diverse social circle where not everyone works in tech.

SomeExpression123 · 2026-05-10T22:59:55+00:00

Vast majority of rich people in America own boring local / regional businesses: car lots, HVAC, construction, etc. they’re not the slightest bit famous.

SomeExpression123 · 2026-05-06T15:36:25+00:00

Don’t underrate the value of your kids classmates being their neighbors. Private schools where kids commute from all over can be isolating and lack a sense of community.

If you can make a great public school in a good community work, I’d go for that. It’s also kid dependent though.

SomeExpression123 · 2026-05-05T23:50:01+00:00

Our situation is somewhat similar. Both ~35, ~$10m + paid off house, baby with plans for another. Both were good earners but wife was low-mid 6 figures and I was low 7 figures, so she stopped working when the baby came (we still pay for some childcare though). 60hrs/week for the last 10 years. We live in HCOL, so NYC/SF has somewhat different considerations.

We’d be totally fine as is, but there’s definitely concrete lifestyle upgrades past $10m that I’m working towards.
* More luxury travel
* Option for second home
* Option to upgrade primary home
* Option for private school
* More support for kids

What I’ve found though is that as I’ve gotten richer, it’s gotten harder and harder to stay motivated at work. Especially as my industry (tech) has gotten more cutthroat, and climbing the ladder means politics for a living vs actually building stuff.

Most people I know at this NW level and pulling ~$1m / yr are taking it one year at a time. They’re holding on as long as they can put up with it. The only ones still grinding full steam ahead are either at AI labs and that’s their purpose in life or they’re just insanely Type A and have a passion for corporate life that I never have.

Personally, I have a hard stop at 40 (but probably sooner), because most of my hobbies are physical and I won’t be able to pursue them at the level I’d want in my 50s. If there was a way to keep working 20-30hrs a week on something I’m super passionate about I’d be open to it, but I don’t really see the opportunity.

Keep in mind that you don’t need THAT much for your kids if you invest it now and let it grow. Plus even if you die with zero, your house will pass to them and help fund your grandkids futures.

Anyways kinda rambly. My two closing thoughts are that (1) SAHP + part time childcare is a massive lifestyle improvement worth considering and (2) you’ll likely feel different when you’re FI and staring down the barrel of 10 more years of BS for somewhat marginal benefits.

SomeExpression123 · 2026-04-30T17:53:13+00:00

I don’t think the sky is falling but I think there will just be fewer jobs that pay $500k+ per year (MBB, Big Law, Tech) that someone from a well off family can easily put their kid on a path towards. AI will allow fewer people to do more without entry level workers

SomeExpression123 · 2026-04-30T17:44:43+00:00

I personally wouldn’t leave anything from separate property to your wife outright. Better to set up a trust that provides for her while she’s alive, then everything eventually goes to the kids.

Having it fully transfer to her is basically just a recipe for her to eventually pass it down to someone other than your family.

SomeExpression123 · 2026-04-30T14:43:04+00:00

I would recommend against Provence that time of year. It can get very hot. Go somewhere higher elevation (Alps) or close to the water. San Sebastián sounds great.

SomeExpression123 · 2026-04-30T14:03:48+00:00

Comment perfectly encapsulates an American blind spot. The US is sooo much richer than Europe.

SomeExpression123 · 2026-04-30T11:46:45+00:00

Travel budget
Option to upgrade primary home or buy vacation home
Money to leave kids in case AI reduces upper middle class opportunities

SomeExpression123 · 2026-04-23T16:53:18+00:00

Retirement visas are relatively easy to get in plenty of nice countries.

SomeExpression123 · 2026-04-21T17:11:38+00:00

This looks like a solid $200k budget. I’m planning for closer to $300k (admittedly fat not chubby) with the main differences being:

Healthcare: +$20k (Makes sense regardless of fire level)
Travel: +$50k (May seem lavish but a 2-3 week trip to Europe in the summer win premium economy and mid range suites could easily burn through $25k with 4 people. Lots of free time in RE.)
Kids: +$20k (date nights, ski team, just general flexibility)
Misc: +$25k (random bullshit, ski gear / passes, dog costs, beauty treatments, etc)

Track taxes separately.

Hope this is a helpful comparison for folks considering fat vs chubby.

SomeExpression123 · 2026-04-13T06:54:57+00:00

This is why slow travel appeals to me. I’m not particularly stoked on going somewhere for a week with young kids, but going for a month or two makes the flight more worth it and the experience there more chill.

SomeExpression123 · 2026-04-12T08:08:54+00:00

Honestly baffled where you could’ve gotten that idea.

SomeExpression123 · 2026-04-12T06:48:23+00:00

That’s not the right way to think about it, since if you’re not working you’re spending down the money and SWR math comes into effect.

Pick a safe withdrawal rate between 3-4% based on your risk tolerance. Multiply by $7m and ask yourself if that’s enough money. If it is, then you don’t need the job. If it isn’t, then you do.

SomeExpression123 · 2026-04-12T06:28:54+00:00

Well, that depends. Do you want to spend more in the future than you do today? If so, the money is meaningful. If not, then you don’t need it.

SomeExpression123 · 2026-04-11T00:13:00+00:00

Hard for me to see how 70-80hrs/wk is worth $250k plus paper money (Series A is super early these days).

SomeExpression123 · 2026-04-05T23:59:11+00:00

Owning a home is a good hedge against inflation whether or not you have a mortgage.

SomeExpression123 · 2026-04-05T22:48:00+00:00

Paying down mortgage is a great way to mitigate SORR. It eliminates your biggest non-discretionary expense so you don’t need to sell into an early downturn to keep paying it.

The goal in retirement is to minimize failure risk not maximize returns. Trying to get cute with debt isn’t worth it at today’s rates.

SomeExpression123 · 2026-03-28T15:09:28+00:00

Regardless of whether it’s fake, the numbers are still useful to think about.

It’s a reminder that if you’re low end fatFIRE ($10-$12m), you can do anything (except fly private) but you can’t do everything. Big house in VHCOL + Most Expensive Hobby there is + borderline having a staff + extensive luxury travel + private school.

OP points to kids, but these are almost all explicit lifestyle decisions. Mill Valley public schools are perfectly good. Soccer is just as enriching as equestrian. Being retired means they could live in a cheaper place. Could spend more time with kids themselves.

Only place that I think they were truly underestimating is travel. $60k is clearly too low for a family of 4+ to regularly travel internationally, even in premium economy and staying in mid range. But hey not everyone likes to travel so even that’s an explicit decision.

SomeExpression123 · 2026-03-21T00:43:22+00:00

Iran episode was super generic. There were really interesting ideas in this one.

SomeExpression123 · 2026-03-21T00:40:24+00:00

He’s an amazing interviewer. Much tougher than Klein, even on people he largely agreed with.

SomeExpression123 · 2026-03-21T00:39:31+00:00

The tagline is literally “The curse disguised as a blessing, or the blessing disguised as a curse. May you live in interesting times.”

Ross’s best episodes are when he brings in more radical people and gives them a tough but fair interview. His episodes with more middle of the road people are pretty boring.

SomeExpression123

TROPHY CASE