Seasonal Semi Retirement Jobs That Pay Well

SeasonalFIRE…

It’s a different flavor of semi-retirement that allows you to work during the crummy weather months and enjoy your free time during the rest of the year.

I’m excited about this post because it’s something I’ve been scheming over for a few months now. Ever since summer began.

Would You Work Seasonal Jobs to Jettison the Cubicle?

One of the lovely features of living in the Upper Midwest is our highly disparate seasons. When it’s winter, you KNOW it’s winter. Cold. Dark. Snow.

And in the summertime, it gets so hot and humid, we dare to complain. Spring is like Winter Junior, and our autumns are Winter Senior. Yeah, it feels like you can’t win when only 6 or 7 months of the year are Parka-free.

What’s all that got to do with “work less, enjoy life more” you ask? Simply an observation I’ve been mulling…

Could there be such a thing as seasonal work in retirement where you pound it out working full-time for six or seven months during the crappy seasons, then take late spring through early fall off??

If you’re like me – nervous about fully retiring early as FIRE looms close, you might want to consider something like this SeasonalFIRE concept. Especially if, like me, you’re “blessed” with weather dynamics that leave you longing from the office on a gorgeous August weekday, or bored as heck from home during a January deep freeze…

Semi Retirement Jobs that Pay Well

Thanks to Google, we can dig up some useful data on seasonal jobs that pay well enough. See any here that entices you?

• Customer Service Representative (No way. Been there, done THAT. Too stressful.)
• Tutor (Interesting, actually!)
• Tax Manager (Has potential. I do enjoy spreadsheets and have a modest knowledge of tax preparation.)
• Technology Retail (Nope. Not wearing the royal blue polo. Not going to try to explain technology with sales pressure behind it.)
• Social Media Assistant (Basically, blogging for someone else. Nah.)
• Market Coordinator (Maybe? Not sure why this is seasonal though…)
• Photographer (This feels like a glutted market to me. Either way, I have no interest in making the baby smile while sitting on Santa’s lap!)
• Decorator (This could be jolly! Set up trees, ornaments, and other dust gatherers in August, in anticipation of the Holy Shopping Season… NOT.)
• National Park Service (LOVE this one. The only hitch is I’d reckon the NPS wants more seasonal help during the summer, which is when I DON’T want to be working…)
• Fitness Trainer (Seasonal, since fall and winter are when most people visit the gym. I’d need Mrs. Cubert to whip my behind into shape before I could ever hope to teach someone else though. We can have goals though, right??)
• Seasonal Recruiter (Meh. means having to listen to others sell me on why they’d be a good fit after I’ve chased them down to talk to me. BORING.)
• Event Planner (This one sounds kind of cool. Holiday parties, galas, and events are more concentrated during the colder months. And I could use my project management skills…)
• Golf Caddy (A summer seasonal job that would be a test of wills. Get a few Judge Schmales and it’s all over for me… Pass.)
• Personal Gift Shopper (Here we go… Spend OTHER peoples’ money!! Sign me up! You can earn $100 an hour. We are living on the decay side of the civilization curve, but let’s shop till we drop, okeydokey??)
• Santa (Too skinny to take this on. But the pay is darn good. And it pulls in $100 – $200 an hour. I suspect the bushy beard and mustache serve as germ and virus protection, along with the gloves…)

Anyone got a spare Santa beard and suit lying around?

SeasonalFIRE Jobs in the Great Outdoors

One other super fun seasonal gig I’m more familiar with is the river raft guide. A friend of Mrs. Cubert has spent her post-collegiate years leading rafting tours in Moab during the summer months, then takes a long winter break to travel like a vagabond, ala Anthony Bourdain.

The only hitch with that lifestyle (we saw it firsthand) is you don’t get paid enough to live cozy and cushy, especially in an area as pricey as Moab, Utah. Our friend shared a rented small house with five other river guides. The place was nice enough, but the tenants were absolute SLOBS. (I think it’s a rock-climber thing…)

At any rate, closing in on age 40, she and her husband are happy to keep up the tradition and live out their dream lives working outdoors in a beautiful landscape, and then picking up side hustles overseas to fund some amazing adventures. A few months hiking and exploring in Thailand / SE Asia? A few months in Britain working a hobby farm? Sounds terrible!

The only OTHER hitch? I’m not sure you can reach FIRE if this is your primary career gig (as is the case with our friend). Guides make $70 – $100 per day (before any tips) and that’s barely enough to cover rent. This is, I suspect, why our friends eventually found a van to live in.

All that said, one could follow the path of our friend’s boss, who left Wall Street in his 30s to start a rafting company of his own. Running a seasonal business is full of risks, but that freed-up time during the offseason would be mighty appealing. All you need is a little pluck to start your own business.

Are There Seasonal Jobs that Pay Well and Use My Current Skills?

There are several options for finding gigs that use your cubicle job skills on a seasonal basis. SeasonalFIRE is a close sibling of SemiFIRE, particularly where consulting is concerned. I believe for me, the ideal off-ramp from full-time cubicle craziness to early retirement is consulting.

Here’s why: I know how to organize corporate chaos and build consensus on direction. I know how to establish strong and effective teams. Why wouldn’t companies A, B, or C need a little spot work to help solve their problems? It could be a one-week stint or a six-month gig. Either way, I’m not locked in forever.

Maybe I could put out my shingle every fall, then kick back come springtime and work on the rentals. Seek adventures with the kiddos while they’re on summer break, etc., etc.

Reading this short and sweet article about how easy it is to dive into part-time consulting has me energized to fire up yet another LLC and start this new side gig. Having built a pretty solid LinkedIn network over the years, I have an okay starting position for potential clients.

Examples of Season Work in Practice

I love this idea shared by Carl H., a member of my Facebook Group – the Cubicle Survival Smarts Club Band:

Forgive me if I stretch the idea of seasonal a bit, but I make a nice little piece during the testing season. I’ve been an Advanced Placement (AP) exam grader for the past ten years. It’s pretty good money, they give you three squares a day, put you up in a good hotel, and pay for all your travels. The best part is that I get to geek out with fellow stats nerds for a week. 

$1600 for seven days; $2400 if you are a table leader (two days extra work…you essentially check that the graders are staying on the rubric)

Not too shabby, huh? $2,400 bucks for whapping kids’ wrists with a lacquered ruler when they try to cheat? Okay, okay, it’s not Catholic School, but still. How hard can it be to make sure students simply follow exam rules? I might look into this, especially if there are options that don’t require as much travel.

Interestingly, some individuals could easily adopt SeasonalFIRE but choose to keep plugging away throughout the year. The Wealthy Accountant had this to say in a Twitter response to the question “Any of you have experience with seasonal work you’d want to share?”:

I started with that premise 38 years ago when I became a tax preparer. Now I work year-round because I enjoy the work and people keep asking. That isn’t the worst thing that could happen.

I can appreciate and respect that. But I’m pretty sure my accountant drops off the face of the earth shortly after the April filing deadline – probably resurfacing from some Caribbean island around August…

In another response to the same question, Raina from Start Living Richly had this to offer:

We have thought about this before…but the challenge for us (Texas) is the crappy season here is summer. This is also when your kids are out of school, making working difficult. We’ve been toying with the idea of eventually just leaving to go someplace nice in the summer.

This is the inverse situation of the Upper Midwest — climate-wise. But how nifty would it be to have the option to telecommute from a cooler clime during summer, if you could swing some affordable seasonal housing? Send the kids off to play while mom and dad dial in to work remotely… Raina offered up:

I think that’s the goal we’re slowly moving toward. My work is already remote, but the hubs, are not so much. He’s hoping to slowly extend the time he’s out of the office and working remotely to show it can be done over the next couple of years.

There was a final exchange on turning her Texas home into an Airbnb during the summer months. Which could potentially work for business travelers, traveling nurses, etc? Not many tourists will be looking to escape to the cauldron of blazing hot Houston summers!!

SeasonalFIRE as an Off-Ramp to Early Retirement?

Reading between the lines, you’d get the impression that I’m dancing around the fear of retiring early from Cubicle Hell. Yeah, I’m still working through this process.

It’s tough when you’ve been in a good groove for so long, and have the recognition and rewards, only to put it all behind you. If I walked out the door tomorrow, sure, I’d miss the big paycheck and the sweet benefits package.

I think I can overcome those things. What I don’t think I can easily overcome is the prospect of feeling less useful (i.e., loss of prestige). Couple that with missing camaraderie with colleagues, and leaving this phase of life all of a sudden feels quite daunting.

See, things start to click in once you hit your mid-30s, 40s, and so on. Retire at 30 and you haven’t given yourself enough time to adapt to the hamster wheel and master “the game”. So it’s easier to retire early at 30, then, say, 40, from a mindset perspective at least.

The hope is that perhaps seasonal work is the bridge to eventually and fully letting go of those silly, seemingly ingrained motives. Nothing wrong with being a “swami”, but at some point, wouldn’t it be great to reclaim a little time for health, writing, and enjoying some fresh air?