Looking Back, Racing Toward Retirement Was a BIG Mistake
I never dreamed I’d retire before I hit 34. But I did.
After graduating with an engineering degree and then an MBA, I worked at Ford Motor Company in Detroit for five years. Then I had the good fortune to team up with Barry, the top student in my Ohio State MBA class, to launch our own company. Barry had also gone to Ford, but out of boredom with the corporate world, he only lasted 13 months.
My First Business Venture
Barry and I launched a staffing firm that provided outsourced HR services for lots of small companies in metro Detroit. Also known as a PEO (professional employer organization), our clients loved us since we took many of the burdens of payroll, taxes, benefits, and insurance off their shoulders.
One of our clients nominated me for Ernst & Young’s Michigan Entrepreneur of the Year, and I was a finalist for that award in 1996 and 1997.
Wall Street was enamored with the PEO business in 1996 through 1998, and many companies went public. We caught the attention of one that was awash in cash, and suddenly, in Fall 1997, I had a few million dollars in my bank account and the freedom to go anywhere I wanted—and to do whatever my wife and I chose.
We had two young children, and we lived 2.4 miles from the Detroit border (on 8-Mile Road. Did you see the movie?). Detroit was imploding, and we were tired of seeing our kids’ toys get stolen from the yard and having our car stereos removed at night. We wanted something different for our two (eventually four) children.
My Next Business Venture
In a perhaps knee-jerk reaction, we acquired 120 mountaintop acres in the Blue Ridge Mountains of Southwest Virginia. We built a new home and invited quite a few friends to do the same. Many eventually built nearby.
I was gonna be living the dream.
I was always troubled by the long hours I worked, and I knew I could be a much better husband, father, and friend if I could find a way to slow down. But I had been living by an entrepreneurial mantra:
Entrepreneurs are free! We have the freedom to work any 80 hours per week we choose.
While I don’t recommend this to anyone, that was my reality up to that time, and when we moved to Virginia, I truly was free from that daily grind.
We started a non-profit organization to reach out to international students studying in the U.S., but that was low pressure and low time commitment. Now I was free to become the best version of myself.
The best husband. The best father. The best friend.
But that’s not how it worked out. I became the worst version of myself.
The worst husband. The worst father. The worst friend.
Oh, and I told people, “I’m an investor now.”
My First Stab at Being an Investor
I didn’t know the first thing about investing. I was a speculator, and my bank account paid a dear price for my folly.
What’s the difference between investing and speculating?
Want more articles like this?
Create an account today to get BiggerPocket's best blog articles delivered to your inboxSign up for free
Investing: When your principal is generally safe, and you have the chance to make a return.
Speculating: When your principal is not at all safe, and you have the chance to make a return.
But that’s another story.
Anyway, what went wrong? Why did my ambition to be the best version of myself turn out so poorly? And what did I learn in the process?
Why I Think Retirement Is Overrated
OK, so I didn’t necessarily retire in the traditional sense. But I did get a taste of what it could be like. And trust me, it was miserable. For me at least.
Yes, I had the freedom to do whatever I wanted. Freedom of time. Freedom to travel. Freedom to sleep in. Freedom to invest (or speculate). Freedom to move to a mountaintop.
(By the way, as I’ve often shared, I wasn’t a bit happier the day after selling the company than the day before. Money really doesn’t bring happiness. For this reason, I recommend that everyone have a big “why” that they are living for. But that’s another story for another day.)
Anyway, I wasn’t created for all of that freedom. Yes, I was designed to be free. But I got really bored. Really quick.
I knew I wasn’t supposed to be bored (who told me that anyway?), so I had to act happy. I had to act like I was enjoying my freedom.
But I was a high energy entrepreneur. And to go from 100 miles per hour to just above zero was no fun at all.
Like I said, for me at least, and for others I’ve spoken to, retirement is overrated.
Now, I know that many of our loyal BiggerPockets readers have a goal to create a passive income stream so you can retire early. So I hope this doesn’t offend you. But this is my experience, and from what I’ve heard, the experience of many others.
Do Early Retirees Really Live Longer?
When I was at Ford, my boss told me that the company statisticians calculated these figures:
- Those who retire at 65 have a life expectancy of 11 months.
- Those who retire at 64 are expected to live 5 more years.
- Those who retire at 63 are expected to live another decade.
So I took his counsel and retired at 28. (That should give me 150-year or so lifespan, right?)
But seriously, this rumor about those retiring early has made its rounds throughout American culture. It originated with a supposed study by Boeing. There’s only one problem with this study…
Boeing says it’s not true. 
Why Is Retirement Overrated?
Here are some reasons that retirement is overrated:
1. It can lead to unnecessarily deferred dreams. Some people plan their lives around a future someday, and they defer their fun and enjoyment of life ’til then. But we have no guarantee of tomorrow. We don’t know about the future of our health, economy, or relationships.
I was talking to the wife of a good friend yesterday. They have always been role models of scrimping and saving and penny-pinching. She’s often told my wife how she goes to three grocery stores to shop (in one day!) to make sure she gets all the best deals. My friend, her husband Doug, was a highly paid consultant—until he got dementia in his mid-50s. Now she’s checking him into a memory care facility, which will pillage their finances. And she’s looking at an uncertain, lonely future.
A wise man once said: “Why do you boast about tomorrow? You don’t even know what will happen tomorrow. You are but a mist that appears for a little while and then vanishes.” (This is paraphrased from St. James.)
2. Not working just doesn’t work for many people. I admit I haven’t done an exhaustive search of history, but as far as I can see, the concept of and obsession with retirement is a recent Western phenomenon. It is not something that our forefathers over thousands of years of earth history seemed familiar with.
So it makes me question whether it is even part of our design. Were we designed and programmed to retire at all? You logic scholars can probably destroy my argument, but I really do question this concept. Personally, I never plan to retire—but I do plan to shift my focus as I grow older. Perhaps this is why it doesn’t work for so many people.
3. Most people aren’t prepared for retirement. Did you know that 10,000 Americans turn 65 each day? But up to half of those have less than $10,000 saved for retirement. With the average Social Security check running under $1,500 per month and the prospect that the system will go broke within a few decades, many have not counted the cost to prepare. (This is one of the reasons we invest in mobile home parks.)
Would you build a house without calculating the construction costs? Yet many people give more thought to the cost of their upcoming vacation than the cost of their decades-long retirement.
I know that is not the readers of BiggerPockets, of course, because you all are the smartest, most ambitious people I know in terms of planning for your futures—seriously. That is why you are here. I wish I would have had BiggerPockets when I sort of tried to retire 22 years ago.
4. The convergence principle. Each one of us has unique DNA. But it’s clear that we’re more than just physical beings. What if there is programming in your soul that defines the ideal course of your life? Your destiny? What you are supposed to be doing with the best years of your life?
Some researchers and teachers call this The Convergence Zone. It is based on the principle of convergence. I learned this from an interesting teacher named Dr. Lance Wallnau.
Convergence is when you’ve reached the place in your life where all of your strengths, all of your successes, all of your talents and abilities and gifts, all of your education and training align. All of your history, passions, desires, and dreams, your employment and your recreation, all that you have a knack for align.
This is the place where you find out what you were called to do.
When You Reach Your Full Potential
When you’ve reached that place, you find yourself saying things like:
- I’m in “The Zone.”
- I’ve found my sweet spot.
- This is too much fun to be called work.
- I constantly lose track of time.
- Those around me are really benefitting from the fruit of my labors.
- I feel so fulfilled. Finally!
- I feel fully authentic. I don’t have to wear a mask anymore.
- I feel 100% alive!
You’ve certainly experienced moments like these, right?
The problem is that most people don’t get to the place of convergence until they are in their 50s—or even their 60s. Do you see the problem with this?
If you retire early, you may be robbing the world and yourself of your very best, most productive, and most fulfilling years. I think—actually I’m sure—that would have happened to me if I had not made so many investing, errrr speculating, mistakes in my 30s and if I would have stayed in my so-called retirement.
I’m thrilled to have the opportunity to be talking to so many of you and to be writing, podcasting, and managing two commercial real estate investment funds.
And now that I’ve traveled the world, with my mid-50’s lens, I have seen the massive pain on this planet. Pain that I have vowed to do something about, as long as my heart is beating and I have air in my lungs. (You can read my profile for more details.)
I wouldn’t have it any other way.
What about you? Have you really thought through this retirement thing? Are you sure you’re on a path that will lead to you enjoying life to the fullest and making the maximum possible contribution to this planet?
Let’s chat in the comment section below.