Every time we scream from the rooftops that you can retire several decades early by working a middle-class job, living frugally, and investing in passive index funds, we get a few common objections yelled back at us.

One of those complaints is actually super reasonable: “I don’t want to stop working forever when I’m 30 years old; that sounds boring.”

Fortunately, there are a million beautiful shades of gray between “perpetually working 50-hour weeks to climb an endless corporate ladder” and “laying in bed collecting dividend checks, watching TV until you die.”

In the past, we’ve talked a lot about how you can take inexpensive “mini retirements” (aka extended sabbaticals) during your career — with or without your employer’s permission. For example, we took 6 months off work to explore Hawaii back in our mid-20s, and another 7 months off to visit every National Park in the United States.

For the last 3-4 years though, neither of us has really had a “career” to take a break from. Although we’ve enjoyed a little part-time freelance work, it hasn’t added up to many hours or been financially necessary, so the label “retired” has felt like a pretty good fit.

Photo of Lauren and Steven in Australia
Enjoying a 3-month break from our nonexistent jobs earlier this year in Australia.

Early retirement has been awesome. But recently, an interesting business opportunity fell in my lap, and it made me consider something new: In the same way that we used to take “mini retirements” from our full-time careers, what if I tried taking a “mini un-retirement” from my post-work life today? So, I’m going for it (at least for a little while)…

Reasons to Consider a Mini Un-Retirement

If you’ve already followed the advice on this blog and no longer need to work for a living, or you’re just wondering what goes on in the head of someone who hasn’t had a full-time job for several years, here are a few reasons someone might actually want to “un-retire” for a short period:

1. You want a mental (or physical) challenge.

Most people who choose to work when they know there’s no financial need for it are probably just looking for an obstacle to overcome, mainly because it feels good. It’s the same reason people go rock climbing.

My friend Jon (who incidentally enjoys climbing rocks) says that the secret to happiness is solving interesting problems. I’d say there is a lot of truth to that, and it’s pretty easy to find interesting problems to solve in the world of business.

2. You miss the social interactions you got from work.

When most of your friends have 2 free days per week and you have 7, loneliness has the potential to creep in. Having a partner to retire and travel with helps a lot, but not everybody stops working at the same time as their spouse. Fortunately, there are lots of ways to make new friends who share your schedule, and interacting with customers and coworkers is one of them.

3. You want to make a positive difference in the world.

Arguably, any business with a product that people are happily forking over cash for has a positive impact on those people (otherwise, why would they buy it?). But I have to imagine that some work — like practicing medicine or taking care of the elderly — probably feels especially good. I can understand why someone might want to return to a job like that, regardless of the financial benefits.

There’s also a group of people who practice “earning to give” (part of the effective altruism movement) — where you earn money beyond what you need for the sole purpose of giving it to highly effective charities. I have to admit that this idea appeals to me and Lauren more each year, and we’ve taken some baby steps in that direction recently.

4. Your retirement savings are disappearing faster than expected.

This is probably the explanation that will flood our social media comments after we publish this blog post. For some reason, there seems to be a dedicated group of internet trolls who don’t want to believe that early retirement is a real thing.

In truth, our net worth has grown by several hundred thousand dollars over the past few years of early retirement — even while taking expensive vacations — thanks to gains in our investment portfolio and home equity. We are not running out of money.

We’ve also continued to maintain very modest living expenses (somewhere in the vicinity of $30k/yr combined when not traveling, as of 2023), making us feel truly financially invincible.

With that said, “running low on money” is a perfectly legitimate reason to start working again if it applies to you. One of the biggest benefits of retiring young is that if your investments don’t cooperate, you have tons of time to work a little more to make up for it. That’s a feature, not a bug!

5. You want to chase a dream that you never took the chance to pursue before.

And here it is — the biggest reason for my new venture (and maybe yours!). Let me explain…

My History with Entrepreneurship

Back in early 2016, Lauren and I had just returned from our honeymoon, and I was starting a small business as a private physics tutor at the University of Florida. After just a few months, I was already making decent money (a rate of about $50k/yr) with a full schedule of clients.

Since I only had so much time to sell each day, I started developing products to sell, too — in an attempt to make my business more scalable. I started selling homemade exam review PDFs to my existing clients for $20 a piece. That’s when I got an unsolicited phone call.

It was a (much bigger) local tutoring company, asking to interview me for a job that I never even applied for. I decided to hear them out, and when they offered me a starting salary of $70k/yr as a tutor, I felt like I’d hit the lottery (especially because we didn’t need anywhere near that much money to live in a mortgage-free condo in low-cost Gainesville, Florida).

Photo of the Bull Gator at UF

I rode that job out to a top-end salary of $90k/yr, saved and invested 80%+ of my salary along the way (while Lauren did the same), and quit in 2020 to retire from full-time work at age 29 (Lauren retired first at the end of 2018).

Life is good, and I have no complaints, but I’ve always wondered: Did I ditch my small business right on the edge of a major breakthrough? I gave up entrepreneurship (which was really interesting and exciting) for the certainty of a steady paycheck, and part of me thinks, “Could I have pulled off something bigger?”

Recently, my friend Marty (a coworker from the aforementioned tutoring company) joined me for a walk on the beach (a good place to convince me of anything) and persuaded me to give it a go with him.

Just last week, we launched a company together.

Introducing CramBetter

The new business is CramBetter, a college math and science tutoring company focused on efficiency — helping students learn more, in less time, for less money (because if we’re being honest, the last thing most college students want to do is study and go to lecture, and most are broke 😅).

The magic of this business is that it allows us to serve an unlimited number of customers via automated online content delivery. We don’t have to be present at the same time as our students. So, instead of charging obscene amounts of money to privately tutor a few rich kids, we can charge a monthly rate that’s less than we used to charge for one hour of our time.

CramBetter is currently priced at $40 per month to students at basically any college or university who are taking one of the following five courses:

If you are a college student (or a relative of a college student) taking one of those courses right now, please feel free to use the coupon code TRIPOFALIFESTYLE for 90% off (ninety percent; not a typo) the first month of tutoring. Thanks for reading the blog. You can sign up here. Please take the other $36 and invest it in an index fund. 🤑

Tips for Starting a Post-Retirement Business of Your Own

If you’re an early retiree who’s thinking about getting a fun and interesting job for a little while, go nuts. It’s not complicated. Just do it until it stops being fun, and then quit. No worries, since you don’t need the money! But starting a business requires a little more consideration.

Part of the beauty of the business I chose — and the only reason I let Marty talk me into it — is that I truly believe my full-time role can be very temporary if desired.

I’m enjoying almost every second of entrepreneurship right now, but I feel pretty sure that I’ll want to get back to early retirement soon enough. For anyone who is thinking about a business venture as a mini un-retirement, here are some tips to make sure it stays as “mini” as you want it to be:

1. Manage your capital risk.

If you’re happily retired and starting a business, please — PLEASE — don’t invest so much money that it could jeopardize your financial independence. The idea is for it to be an interesting challenge, not a requirement to make a living. Why would you risk what you already have for more money that you don’t need?

I’ve put a lot of sweat equity into this new venture, but Lauren and I have only invested a low four-figure sum of cash into it, with no plans to put significantly more money at risk. If the business fails (which is always a very real possibility!), I plan to go back to being happily retired again.

2. Build something that can eventually be made passive.

If my business partner had told me he wanted to start a one-on-one, in-person, private tutoring company, I would have said, “I wish you the best of luck.” That was awesome when I was 25 and hustling to get ahead, but I’m just not interested in a job with an hourly wage any more.

In this business, we can front-load the work of building a library of content, and that content can theoretically be re-curated as necessary and sold for years to come. I think this has the potential to become a 4-Hour Workweek-style business in a relatively short period of time. That’s exciting to me.

3. Make sure the recurring tasks are the ones you find fun.

Not every part of building a business can be fun every day. That’s unrealistic. But when you’re designing a post-retirement business, you should at least make sure that the things you’re most excited about are the ones that might need to continue indefinitely.

Personally, I’ve never gotten to do much marketing or sales in my life, and it’s one of the most novel parts about running this business to me. That’s good, because I think that once our content library is built, marketing and sales is one of the only things that will be left to do continuously!

4. Maintain your freedom to quit.

Obviously, you’re always free to quit doing anything you don’t like, but it’s important to make sure you’re realistic about the commitments you’re making to other people and the consequences of quitting.

If you have a business partner, talk to them about when you expect to want to scale back on work again, and what would happen if you decided to exit the business entirely. These are conversations I had with Marty before we even got started. Plus, he reads this blog, so he kinda already knows my disposition toward long-term, full-time work. 😛

Photo of Lauren in Alaska at sunset
Lauren is helping out a lot with CramBetter (actually, she is a part-owner of the business), but she’s also nowhere near full-time and is maintaining her carefree “retired girl” status. I’m pretty sure she’ll want me to rejoin her before too long. (Photo from a stop into Haines, Alaska, on our Canadian National Parks trip last year.)

Lastly, I want to mention that this entire experience is an experiment to me. Truthfully, I might just have no idea what I’m talking about, so don’t be surprised if I’ve changed my mind about any of this stuff a year from now. But, I think the “unknown” aspect of this whole thing is exactly what makes it all so exciting. Wish me luck!

— Steven

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