I’ve Retired Three Times; Here Are 5 Things I’ve Learned

I was 49 the first time I retired. After nearly 25 years in practice, I turned in my fountain pen at my law firm. Two years later, I retired again when I sold an online business I had built on the side. I retired a third time in 2020 as the Founding Editor of Forbes Advisor.

Here are five things I’ve learned as a serial retiree.

1. Spending Money In Retirement Is Scary

My wife and I were financially ready to retire. Whether you use the 4% Rule or some other rule of thumb, we had enough money for early retirement. Yet I was scared to death of spending money from my savings.

In fact, that’s why I took the job at Forbes Advisor, but please don’t tell my editor. I took great comfort in the salary and benefits. For some reason, getting healthcare through an employer is more comfortable than navigating the healthcare marketplace. It may be called the Affordable Care Act, but I think the “Affordable” part of the act’s title is an inside joke among some politicians.

Eventually, you get more comfortable living off your savings. It does help when the markets are going up, and it helps even more when you can earn 5% on T-bills.

2. Life Has Never Been Busier

I always imagined retirement as a life of leisure. Wrong. My wife and I regularly remark on how busy life is even though we are both retired. Whether it’s taking care of family, spending time with our granddaughter, or attending healthcare appointments that seem never-ending even when you’re healthy, we are just as busy in retirement as we were when we worked.

We have weekly “intentional living” meetings to sync our calendars. We fight to protect our own time against the outside world that demands so much of our time. We have no idea how those still working find time to do anything.

3. Hobbies Help, To A Point

Before I retired, I thought retirement would be easy. One reason is that I have many interests. I love to read, exercise, play chess, and write, which should be more than enough to keep my mind occupied. It’s worked out that way to some extent. But I’ve learned that hobbies only get you so far.

Golf was a lot of fun when it was a weekend escape from the 9 to 5. But try playing every single day, and the shine rubs off quickly. That’s particularly true if your golfing buddies are still working. In my case, many of my hobbies are solo endeavors. That’s fine to a point, but eventually, this introvert needs some human interaction. At times like these, I miss the camaraderie of a job. (Mind you, I don’t miss it enough to go get a job, but still . . . .)

4. Managing Money In Retirement Is Complicated

Managing your money in retirement is far more complicated than before you retire. You have a host of questions to answer that you could ignore during your working years. For example, you have to decide when you’re going to start taking Social Security benefits. If you’re not yet 65, you have to find healthcare insurance. If you are 65, you must make decisions about Medicare and related coverage.

Then there’s the question of how to invest your money. It seemed easy before retirement: Create a simple portfolio of mostly stocks and some bonds thrown in for safety. In retirement, investing becomes a lot more consequential as you begin to spend your money and watch your balance more closely. In addition to managing the portfolio, you must devise a plan to generate a paycheck from all your investments. This requires you to determine which account types to take your money from, which is challenging to figure out.

And then there’s the question of whether you should undertake Roth conversions. Roth conversions can lower your taxes by reducing your required minimum distributions. It’s a complicated question with imprecise answers at best.

Welcome to retirement.

5. Purpose Is Powerful

Finally, I’ve learned just how important having a life purpose in retirement is. In many ways, our life purpose before retirement just happened. We had children and they became a large part of our purpose. I had a career partly because you’ve got to pay the bills, which became part of my purpose. It happened day by day. After a while routine takes over and you just move through the years.

When you hit retirement, however, much of this comes to a stop. Your career is behind you, and the kids have moved out (hopefully). You’re left with a big question–now what?

Before retirement, I thought my interests and hobbies would answer this question. They didn’t, at least not completely. A big part of the answer was a YouTube channel I started to help others with retirement planning. The topic is fascinating to me, it connects me with thousands of people, and it brings in a side income.

If that sounds like a job, well, maybe it is. but I work from my basement, I work when I want to, and I love the work. So maybe in the end, the biggest thing I’ve learned about retirement is to just keep working.