Retirement Begins Long Before You Retire

Including my time delivering newspapers, I’ve had a total of ten different employers in my life. Some jobs were more memorable than others. One of my early roles was at a company that created merchandise catalogs for department stores.

I was twenty—shy, insecure, and working part-time while attending college. I mostly did the tasks no one else wanted: vacuuming, taking out the trash, cleaning the bathrooms. Yet, two women at that company saw potential in me that I couldn’t yet see in myself.

One was Leni, the owner. She encouraged me to switch my major from history to business and promised that if I earned a business degree, she would make me her right-hand person. The other was Jodi, my age, who worked on staging photo shoots—and sometimes modeled herself. Fred from shipping insisted she liked me, but I never had the courage to find out.

I never took Leni up on her offer. Perhaps it was because her son, who also worked there, didn’t like me. Or maybe I simply didn’t believe in myself. As for Jodi, I never asked her out. I couldn’t imagine someone like her being interested in a guy who cleaned toilets and had no plan for his life. My shyness held me back, too.

These days, I’m no longer that shy, self-doubting kid. I tend to speak my mind—which brings me to retirement. Looking back, I realize that the habits I struggled with in my early jobs—self-doubt, hesitation, and risk avoidance—can have real consequences later in life, especially as we approach retirement. Some of what I’m about to say might be uncomfortable, but it’s important.

Here are three ways people sabotage their own retirement:

1. Neglecting our health
On a seven-hour flight to Amsterdam, the man next to me drank two regular Cokes, a glass of orange juice, and capped it off with a slice of chocolate cheesecake. It made me think about friends who never reached retirement—or whose retirements were cut short—because they didn’t take care of themselves.

I recently had lunch with my high school friend, Mark, who has diabetes. His doctor told him, “I can see from your bloodwork that you’re not following my advice. Why do you even come in if you won’t listen?” Even so, Mark still ate rice with his meal, a reminder that good intentions alone aren’t enough.

2. Divorce
I’ve seen how relationship stress can impact retirement. A couple I knew spent years arguing over blame and unmet expectations. Their inability to communicate and compromise eventually led to separation, which not only caused emotional pain but also financial strain—an example of how personal choices can shape the quality of retirement.

3. Not avoiding unnecessary risk
I was amazed at the number of people riding bikes in Amsterdam, especially the elderly, none of whom wore helmets. While biking may not seem dangerous, even small risks can have major consequences.

Take Dave, my former coworker. He planned to retire after paying off his four-year truck loan. But during a charity ride, he went headfirst over the handlebars, ignoring warning signs from earlier falls during training. The accident left him unable to work, and cost him not only his job but also his marriage.

Each of these examples—poor health choices, failed relationships, and avoidable risks—serve as reminders that retirement isn’t just about money. It’s about arriving at that stage of life with your body, relationships, and peace of mind intact.

Looking back, I often wonder how things might have turned out if I had taken more chances when I was younger—if I had believed in myself the way Leni and Jodi did. But perhaps those missed opportunities helped shape my awareness now. They taught me that the decisions we make—or avoid—don’t just affect our careers. They ripple into our later years, into our health, our relationships, and the freedom we hope to enjoy when we finally stop working.

If you still have time ahead of you, don’t wait. Take care of your body. Nurture the relationships that matter. And think twice before taking unnecessary risks that could derail your future. Retirement is not just a destination—it’s the result of a thousand choices we make along the way.

If you’re like me—no longer twenty—remember: it’s never too late to make better choices. We can’t rewrite the past, but we can shape what comes next.