Early retirement is within reach.
Heard that before? Yeah, me too.
I could be out of the rat race in less than a year. But I don’t want to retire to boredom—I want something to keep my brain active and my days useful. Would starting a business after retirement be a good move?
I’ve got time and energy to spare. The question is what kind of business would be low-stress, rewarding, and flexible enough to fit a semi-retired life.
Starting any new business is tough. Usually you need startup cash (often a loan) and a lot of time to keep things running. Start-up survival stats are sobering: if you dream big—restaurant, specialty shop, magazine—your odds of making it five years aren’t great.
So what about aiming smaller? What if the goal is steady cash flow with limited startup costs? That’s where service-based side hustles shine.
Independent contracting or consulting feels like the lane I’m heading into. Time to do some homework.
I’m not opening a brewery. That market is crowded, expensive, and brutal. Craft brewers deserve respect—seriously hard work—but taprooms and equipment scare off most lenders. Same goes for food businesses—too much overhead and too much risk. Even if our Airbnb reviews suggest I could run a great dining room, I’ll pass.
Blogging? Low overhead and easy access to readers, sure. You just have to write something useful and a bit entertaining. The catch is monetization: you need products or services to promote. Some bloggers do very well with recipes, wellness, or personal finance courses and books. This blog earns a bit from referral links, but it was set up as a nonprofit channel—Cubert Enterprises donates to Children’s Heartlink—and I want to keep it that way.
I could start another blog—“Gentrified Cubicle,” anyone?—but one is probably enough for me. There are lots of other online money-making paths besides blogging.
Real estate looks promising—people always need places to live. Markets vary and bubbles happen, but real estate can be a steady business. What if I combined disciplines—property management plus home inspections, for example?
I already rent single-family homes, and I enjoy house hunting. Since 2012 my agent and I have toured maybe fifty homes. You see all kinds of things: ancient furnace monstrosities, sketchy DIY wiring, and yes, weird finds like a dead squirrel stuck in a dryer vent. You also find charm—houses with no shower stalls, tons of wallpaper, the works.
The problem is I don’t like heights. Home inspectors need to climb roofs. I’m fine on a single-story ranch, but a three-story house would have me shaking. Maybe time to get back to the climbing gym?
Real estate feels like the most likely path—about 90% sure. The other 10%? I might take a part-time role doing what I do now: managing corporate chaos. Not as appealing as some other ideas, but it’s an option.
Next: business structure. Common choices are sole proprietor, LLC, and S-Corp. We’ve run side gigs long enough to know the basics.
LLCs are easy to form—file with your state and pay a small fee. The big plus: they protect your personal assets if the business gets sued. Just don’t “pierce the corporate veil.” Keep business money and assets separate from personal use.
S-Corps can cut self-employment taxes, but they add complexity. You’ll need an accountant to make sure you pay yourself a reasonable salary and report taxes correctly. The tax savings can be real, but accounting costs add up.
My plan is to combine the two: LLC for liability protection, taxed as an S-Corp for the tax benefits. My wife’s business uses this setup and it works well. For now, though, until my new venture clears maybe $20K a year, I’ll stick with a plain LLC.
Practical questions remain: will I need employees? Expensive. Can I avoid equipment costs? With real estate, probably. Market research? Crucial.
Employees bring payroll, benefits, and legal obligations, so early on contractors are usually the smarter move. Pay them fairly, and hire employees once revenue is steady.
I’ll research local property managers and maybe do a short internship or shadowing gig to learn the ropes before diving in. Google the competition, talk to local pros, and learn from the inside first.
KPIs matter. Revenue is great, but profit is better. Take my Airbnb side gig: it brought in solid revenue in year one, but setup costs trimmed profits. So it’s back to accounting basics—balance sheets, cash flow, forecasts. You’ve got to track everything. QuickBooks is handy, but for now I’ll use Excel and build a few forecast models.
From a FIRE perspective, the goal is part-time work—semi-retirement, not full-time grind. I want something that brings in decent cash—say $2,000 a month to start—without eating every hour of my day. Success looks like freedom: travel when we want, sleep through the night without 2 a.m. emergency calls.
Do the research. Read, learn, and find good mentors—learning works long after college. Carve out hours to set up your LLC or S-Corp. Shadow a property manager on weekend mornings. I have a few home inspection contacts from those past house tours—maybe they’ll let me tag along and ask a million questions.
The main point: just do it. Remove distractions, prioritize your time, and get out there. That’s how ideas become real businesses.
Share your ideas for starting a business after retirement in the comments below.
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