I SAID GOODBYE TO my career in the retail industry nearly five years ago, at age 39. I’d had my eye on early retirement as soon as I entered the workforce.
My first job out of college was with an upstart retailer, where I worked 80-hour weeks for many years as I sought to improve my skills, knowledge and reputation. I did well, earned multiple promotions, and had high hopes for a life-changing payout from the company’s planned initial stock offering.
But instead, the business failed.
I started over, spending a decade climbing the corporate ladder at other retailers. I earned as much as I could, lived modestly and invested the surplus. Finally, deciding I had enough saved, I took the financial and emotional leap into the unknown.
I thought I had a vision for what early retirement would be. But five years after I left office work—what I now call “my first career”—my life, including my financial life, is quite different from what I’d imagined. Whether you’re planning an early retirement or a more traditional one, these surprises and the lessons they taught me may apply to you, too.
I’m busier than I thought I’d be. I never imagined sitting on the beach all day, every day—does anyone?—but I still thought the pace of retirement would be relatively leisurely. Instead, I’ve gotten so busy that I’ve already had to quit two different side hustles to regain control of my time.
In truth, I never stopped working. Here, in chronological order, are the jobs I’ve done since I “retired”:
Remarkably, none of this was envisioned at the time I retired. I still had the energy and desire to learn new skills and be a part of businesses, so when these opportunities knocked, I answered. For the moment, I like the balance I’ve achieved, but I wouldn’t be surprised if future circumstances force me to “rebalance my time portfolio” once again.
On top of all this, I’ve pursued personal projects and priorities since leaving the corporate world, including honing my classical piano repertoire, traveling, spending time with friends and family, and getting involved with the alumni organization for my college a cappella group.
My parents are traditional retirees who left their teaching careers decades ago. They’re fond of statements like, “We’re so busy now, I can’t imagine how we ever had time to work.” Before I left my job, I’d scoff at this. What could they possibly be so busy with?
Now, I get it.
The lesson: Sometimes, retirement isn’t “retirement.” We have more time, but not unlimited time. We may still have to protect our schedule, and prioritize the projects that are most meaningful. Some of those projects might even earn some money—which brings me to my next surprise.
I’m still making money. I didn’t quit my retail career until I had a high degree of confidence that our savings and investments, along with my spouse’s business income, would be sufficient to support us even if I never earned another dollar. Instead, to my great surprise, I’ve earned quite a few dollars. Looking at the jobs I listed above, each is or was a paying gig. From those that remain, I’m currently making almost half of what I was making when I left retail.
This, I’ve found, is common among early retirees, most of whom look back and wonder why they waited so long to leave their job. As a group, early retirees tend to be careful planners who are reluctant to take big risks. Still, it may be overly conservative for early retirees to assume zero future income. It certainly was in my case. Had I known I’d be earning my current income, I would have left the corporate world many years earlier.
The upshot: It’s possible, especially for early retirees, that you’ll keep earning a healthy sum after you retire. This might be cautiously incorporated into your retirement’s financial plan and into the decision of when to leave your job. Almost every early retiree will tell you they waited too long.
I’m spending money like crazy—or, at least, it feels that way. For decades, I was hyper-focused on accumulating savings. I made budgets, tracked income and spending to the penny, compiled reports, made projections, and looked forward to the day when all that effort would allow me to escape the office grind forever.
But after achieving my goal, I found it difficult to switch gears. Mathematically, my approach to money should have shifted significantly once I had enough for early retirement, particularly since I was continuing to earn more than I’d expected. Emotionally, though, I was stuck in the accumulation phase—buried in the numbers, reluctant to spend, and petrified of red numbers on the spreadsheet.
Five years in, I’m getting better at loosening the reins. We have plenty of money, so it makes sense to buy what we want and not sweat the small stuff. I’ve even flirted with shelving my detailed monthly expense tracking and reporting, but the idea makes me queasy. I’ll keep doing it for now, even if it’s little more than an exercise in self-soothing, and hope I’ll eventually muster the bravery to give it up.
What lesson can be learned here? Retirees who have been diligent savers may struggle to enjoy the fruits of their labor. The rationale for further wealth accumulation deteriorates as you get wealthier; the same is true as you get older. At some point, it’s fine to unlearn those strict saving behaviors.
More broadly, I think I was focused on the wrong thing. My vision of early retirement was limited to what I wouldn’t be doing, such as setting an alarm, reporting to a temperamental boss and dealing with corporate nonsense. I was right about all of that, thankfully.
What I lacked was a positive vision for what I’d do with the extra time that retirement created for me. This is a difficult question to contemplate as a hypothetical, though, and only becomes real after you leave work. If my experience is any guide, the best plan may simply be to stay open, curious and flexible when it comes to your life in retirement—and go where your mind and heart lead you.
Eric Hughes used his cash-generating rental properties to leave behind his corporate career at age 39. He now runs the website Rental Income Advisors, where he writes about rental property investing, publishes a monthly newsletter and serves as a private coach for new real estate investors.
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