High-Paying Semi-Retirement Jobs

by yourfinanciallever_com

High-Paying Semi-Retirement Jobs
SeasonalFIRE is a different kind of semi-retirement: you work through the bad-weather months and enjoy your time off when the weather is nice.

I’m excited to write about this because I’ve been thinking about it since summer started.

Living in the Upper Midwest gives you extreme seasons. Winter is unmistakable—cold, dark, snowy. Summer gets hot and humid enough to complain about. Spring feels like a junior winter, and fall is basically winter with leaves. It can feel like you only get six or seven months without a parka.

What does that have to do with working less and enjoying life more? Just this: could you work full-time through the rough months and take late spring through early fall off? If you’re nervous about fully retiring early, like I am, SeasonalFIRE might be worth considering—especially if you crave being outside on a perfect August weekday or get cabin fever during a January deep freeze.

Google can turn up seasonal jobs that pay decently. See any that catch your eye? Anyone have a spare Santa suit?

One seasonal job I know well is river rafting guide. A friend of my wife spent her post-college years guiding trips in Moab in summer, then traveling all winter like a vagabond. It sounded amazing, but the pay doesn’t leave much for comfort in expensive places like Moab. Our friend shared a small rented house with five other guides—nice spot, but very messy housemates (maybe a rock-climber thing).

Now approaching 40, she and her husband still love the outdoor life. They work in a beautiful place during the season, then pick up side jobs overseas to fund long trips—hiking in Thailand for a few months, working on a hobby farm in Britain for a while. Hardly a bad life.

The downside: being a guide won’t usually get you to FIRE. Guides often make $70–$100 per day before tips, barely covering rent. That’s partly why some friends ended up living in a van. On the flip side, you could start a seasonal business—one of our friend’s bosses left Wall Street to start a rafting company. Running a business has risks, but the off-season freedom could be worth it if you’re willing to take the leap.

There are other ways to find seasonal work that use your office skills. SeasonalFIRE is closely related to SemiFIRE, especially with consulting. For me, consulting is the ideal step down from full-time cubicle life. I know how to organize corporate chaos, build teams, and get people moving in the same direction. Companies will pay for short-term help—anything from a week to six months—and I wouldn’t be tied down.

Maybe I could offer consulting work in the fall, then relax in spring, work on rental properties, and take summer trips with the kids. Reading about how easy it can be to start part-time consulting has me itching to form another LLC. My LinkedIn network gives me a decent starting point for clients.

One great idea came from Carl H., a member of my Facebook group, the Cubicle Survival Smarts Club Band. He stretches the idea of “seasonal” a bit, but for the past ten years he’s worked as an AP exam grader during testing season. It pays well, they feed you and put you up in a good hotel, and they cover travel. He gets to nerd out with other stats lovers for a week. Pay is about $1,600 for seven days, or $2,400 if you’re a table leader (two extra days of work). Not bad.

Some people could use SeasonalFIRE and still choose to work year-round. The Wealthy Accountant replied to a recent question that he started as a seasonal tax preparer 38 years ago, but now works all year because he enjoys it and clients keep asking. That’s a perfectly fine outcome.

Raina from Start Living Richly pointed out a different problem: in Texas the “bad” season is summer, which is also when kids are out of school. That makes working seasonally harder. She and her husband have talked about telecommuting from somewhere cooler in summer or slowly extending his remote work time to prove it works. They also discussed renting their house as an Airbnb in summer, though sweltering Houston summers aren’t exactly tourist draws—maybe business travelers or traveling nurses could use it.

If you read between the lines, you’ll see I’m still wrestling with the idea of leaving Cubicle Hell. It’s hard to walk away from recognition, a big paycheck, and great benefits. I can handle losing the money and perks; what worries me more is feeling less useful and losing the status that came with the job. I’d miss the camaraderie, and that makes leaving feel daunting.

You get better at the game as you stay in it. If you retire at 30, you might not have learned the ropes or adapted to the work world the way you do in your mid-30s or 40s. That makes retiring in your 40s different mentally from retiring at 30.

Seasonal work might be the bridge to letting go of those ingrained drives. There’s nothing wrong with being driven, but at some point it would be nice to regain time for health, writing, and fresh air. SeasonalFIRE could be a gentle way to get there.

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