People dream of getting to do what I'm about to do. But what about what comes next?
People dream of getting to do what I'm about to do. But what about what comes next?
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People dream of getting to do what I'm about to do. But what about what comes next?

🕒︎ 2025-10-29

Copyright Slate

People dream of getting to do what I'm about to do. But what about what comes next?

Pay Dirt is Slate’s money advice column. Have a question? Send it to Kristin and Ilyce here. (It’s anonymous!) Dear Pay Dirt, I work in a highly specialized, highly compensated field—and it’s more stress than it’s worth. I have 99 percent decided I’m going to leave my job next year to do something most people only dream of—but there’s something holding me back. I want to spend a year or two doing “dad” stuff with the kids, fixing up the house, actually going to the gym, and that kind of thing. I have no plan on what kind of work I’ll eventually stumble into later, but the intention is it won’t be in my current field. I’m pretty certain I’m not nuts, but with any big decision like this it’s nice to have additional viewpoints. Assuming no complete market meltdowns, we’ll have about $1 million in retirement and $1.3 million net worth. My wife (also 44) will keep working and is on track to receive a pension in retirement that would cover about half our expected expenses. We can pare back our current expenses to match her income, but it will mean zero additional savings for the two kids’ college funds (we have about $25,000 total now), plus lots of little lifestyle changes. I’ll presumably eventually wind up with some kind of job one or two years later, but nothing approaching my current income. Am I setting us up to screw up the ability to retire? For the kids to launch without crushing debt? The math says it’s fine but the fear of scarcity makes a lot of noise. —This Is OK? Dear OK, You’re asking permission, but the math speaks for itself. The real issue seems to be that fear of scarcity you mention. So the real question is, what can you do to make things less scary—and scarce? Let’s look at the trade-offs. You can afford to step back, but, yes, it will come with some opportunity costs. Namely, slowing your retirement savings and limiting what you can put toward college funds. College, in particular, is where you might feel the pinch. With rising tuition costs, $25,000 won’t stretch far for two kids. The good news is, it sounds like you still have plenty of time to save. You just may need to think about future conversations with them about loans, scholarships, or more affordable schools. On the retirement side, you’re in a much stronger position than most of us. With a million dollar nest egg, plus your wife’s pension, plus the likelihood that you’ll eventually get another job—all of this suggests you’ll be just fine. One option to consider is picking up part-time work—freelancing in your field, ride sharing, grocery delivery, that sort of thing. You might not make all that much, and it might cut into some of that precious dad time, but having even a small income stream could make things feel less scarce. You mention it’s likely you’ll end up with another job a couple of years from now. Maybe it would help to have a plan in place—some kind of timeline. Are there classes you can take? Ways to keep your resume fresh, maybe with volunteer work? Are there conferences or networking groups you can join? I’m not sure what that plan looks like, but the mere process of mapping it out could help overcome the mental hurdle of not knowing what the future holds. It’ll make you feel a little more in control, which, again, could help ease the anxiety. My sense is that you’re having a case of cold feet. Which is totally normal—this is a big leap! My two cents? Focus less on what could go wrong and more on everything that will go right. You’ll have more time with your kids, you’ll make more memories, and there will be much less stress in your daily life. Think about all the reasons you’re doing this in the first place. And once you embark on this new adventure, I bet the scarcity will subside and you’ll be glad you took the leap. —Kristin Classic Prudie Should I help my uncle slash my family’s inheritance? My uncle inherited all of my grandmother’s estate about 20 years ago. (Grandma cut my mother out entirely—we’ve always suspected that my uncle pressed his advantage while Grandma’s mind was going.) Since then, he has lived solely off the estate’s dividends. Even though the estate is now worth several million, he’s chosen to live EXTREMELY frugally. Imagine the modern equivalent of one of those famous Victorian misers.

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