There’s something about living through decades of cultural shifts, economic booms and busts, and technological leaps that teaches you a thing or two, right?

For those of us who came of age well before smartphones and social media, life wasn’t always laid out as neatly as it seems to be today. Many of us (myself included) had to stumble, get scraped up, and figure things out the old-fashioned way—through trial and error.

Today, I share five lessons that my generation—the Baby Boomers—had to learn the hard way. These aren’t abstract concepts. They’re lived experiences, the sort you only gain by taking a few lumps and growing wiser for the wear.

1. Life doesn’t follow a straight line

When I was a teenager, the expectation was pretty straightforward: get a job (or go to college if you could afford it), work hard, buy a home, and keep going until retirement. That was the path. 

But life doesn’t stick to neat outlines, does it?

I still remember watching my father work the same job for three decades and assuming I’d do the same. Turns out, by the time I was in my late twenties, industries were shifting, factories were shutting down, and people were being laid off left and right. The “straight line” approach—that tidy plan we all believed in—fell apart for a lot of folks in my generation.

Some found themselves starting over, maybe even multiple times. I had a couple of friends who had to move across the country for brand-new careers they’d never even heard of in their youth. The lesson? Expect the unexpected. Life is rarely as predictable as we’d like.

Winston Churchill famously said, “To improve is to change; to be perfect is to change often.” While I’m not sure perfection is attainable for any of us, I do think he was onto something. If you cling too tightly to a single vision of how life should go, you may miss out on better opportunities or be left unprepared when change hits you square in the face.

For many Boomers, learning to be flexible was a must and it’s probably just as important today. So, if things aren’t unfolding exactly as planned for you, take heart. Change can mean growth—even if it’s uncomfortable at first.

2. Relationships matter more than rigid independence

I grew up in an era that prized self-reliance. You looked after yourself, and that was that. But as time went on, I realized there’s a difference between healthy independence and shutting out the support of others.

There was a period in my thirties when I tried to handle every obstacle on my own. I didn’t want help with finances, job decisions, or even emotional struggles. I was determined to shoulder everything. It took a near-burnout episode for me to open my eyes.

I recall reading an older psychology book—“The Road Less Traveled” by M. Scott Peck—where the author touched on how genuine growth often emerges in the context of community and honest relationships. And it’s true: none of us truly thrive in isolation.

Modern research backs this up. One well-known Harvard study found that the quality of our relationships is one of the biggest factors for long-term happiness and health. It’s not about having a massive circle of friends but about cultivating meaningful connections—people who’ll be there when it really counts.

The lesson here? Achieving things solo might feel rewarding in the short term, but it’s building real bonds that pays dividends for a lifetime.

3. You can’t bank on material success alone

Remember the “yuppie” culture of the 1980s—endless talk of big business, bigger houses, and the biggest possible bank accounts? Many of us Boomers got swept up in that, chasing symbols of success we thought would make us feel fulfilled. New cars, high-paying jobs, corner offices.

As the years rolled on, though, reality hit. We witnessed recessions, layoffs, downsizing, and entire companies vanishing overnight. Suddenly, all those material tokens we’d pinned our identities on felt precarious.

I’ve mentioned this in a previous post, but it’s worth repeating: there’s nothing wrong with enjoying your money or celebrating financial milestones. The problem is when you equate your entire self-worth with your net worth.

As Bill Gates once observed, “Success is a lousy teacher. It seduces smart people into thinking they can’t lose.” And let me tell you, I’ve seen plenty of folks who seemed invincible during economic upswings suddenly lose everything when the market dipped. It’s humbling—and for many, it was downright traumatic.

In my case, I remember hitting a financial roadblock when my company restructured. The scramble that followed taught me that money can help you get by, but it won’t always guide you to genuine fulfillment or security. That depth comes from personal growth, supportive relationships, and a sense of purpose beyond the next paycheck.

4. You’re never done learning (and unlearning)

In my twenties, I assumed learning ended with a diploma. You got your degree (if you were lucky enough to go to college) or your job training, and that was it. Little did I know how fast the world would keep spinning—and how outdated certain beliefs or skills could become if I didn’t stay curious.

At one point, computers were like foreign objects to me. I’d tap at the keyboard, half hoping I wouldn’t break something. Fast-forward to the present, and our lives practically revolve around technology. If I hadn’t embraced new tools and new ways of thinking, I’d be lost.

Einstein said, “Once you stop learning, you start dying.” It’s a statement I took for granted for too many years. 

But learning isn’t just about technology; it’s about staying mentally limber, being able to update your viewpoints, and welcoming fresh insights—even if they challenge what you’ve believed for decades.

Of course, unlearning is equally important. Sometimes we hold onto attitudes that might have made sense in the past but no longer serve us. A small example: I once thought you had to maintain an almost stoic rigidity to be taken seriously in the workforce—no showing vulnerability. Over time, I’ve discovered it’s okay, even beneficial, to show more empathy and authenticity. People respond to realness, not a stiff upper lip.

5. Health is everything

We like to glorify the past, but the truth us many of us Boomers grew up chowing down TV dinners and thinking minimal exercise was fine as long as we weren’t visibly overweight. Smoking was common, too—some folks didn’t even consider it a health risk until later public awareness campaigns hit full force.

Let me tell you, many of us learned the hard way that your body eventually tallies up all those late-night indulgences, lack of movement, and accumulated stress. I’m in my sixties now, and I see friends and acquaintances grappling with health issues that might have been preventable if we’d paid attention sooner.

Sure, healthcare has improved leaps and bounds, but the best medicine is still prevention. Something as simple as daily walks can keep your joints and heart in good shape. I also discovered the value of mindfulness practices—a concept that might’ve sounded too “new age” to me when I was younger. 

Brené Brown (a researcher I admire) once wrote, “Daring to set boundaries is about having the courage to love ourselves, even when we risk disappointing others.” It applies not just emotionally but physically, too. Prioritizing sleep, taking time off work, or saying no to certain demands might ruffle some feathers, but it’s essential for long-term well-being.

Wrapping it up

These five lessons come straight from the experiences of a generation that’s had more than a few bumps along the road. 

We’ve seen periods of great prosperity and times of serious hardship. We’ve chased illusions of success, neglected our health, and learned that true happiness often lies in connections and curiosity.

The question I’ll leave you with is this: which of these lessons do you feel you need to work on the most right now? 

Life never stops teaching, and each new chapter brings a fresh set of challenges. The key is to remain open—open to changing circumstances, open to people, open to continuous growth, and open to the fact that you might need to pivot from your current path at any moment.

After all, lessons learned the hard way are some of the most impactful ones. If my generation can lend you a map so you don’t fall into the same ditches, so much the better. 

Stay curious and keep moving forward. And remember, it’s never too late—or too early—to embrace these truths.