7 Steps To Take In Your 20s To Live With Fewer Regrets In Your 50s

What I’d do differently if I could go back in time

Licensed from Shutterstock // PheelingsMedia

On my 21st birthday in 1992, I went out to a bar, legally, for the first time. I remember that night vividly, everything from the doorman wishing me a happy birthday after checking my ID to the woman who kissed me after buying me a Jagermeister shot.

I wish I could forget the following morning — waking up on my friend’s floor, still wearing my bar clothes, now saturated with a noxious mixture of dried sweat, cigarette smoke, stale beer, and an invisible but surely present remnant of vomit.

Adulthood started with a bang, but the years that followed were full of disappointments, missed opportunities, and embarrassing miscues that I would come to regret.

As the years turned, I learned from my regrets, making small changes to how I approached decisions, fear, relationships, and passions. And now, in the waning days of my fifth decade, I can proudly say that my forties were awesome.

If I could go back in time to my 21st birthday, I’d scale back on the alcohol, but more importantly, I’d embrace these seven changes which came late in life for me.

Deal with life challenges instead of running from them.

On a whim, I moved from New York to Las Vegas after I graduated from college. It didn’t work out, so I moved back a year later. Then I hopped from career to career on the pretense my adventurous spirit needed constant change.

Years later, I realized I wasn’t an adventurer. I wasn’t gutsy. All those job changes and the cross-country move stemmed from the desire to run away from struggles and problems instead of facing them.

If you’re constantly switching jobs, cities, friends, lovers, and surroundings, question whether it’s a lust for the unknown driving you or a quest to escape confrontation and problems.

It took me decades to understand this.

Your scenery may change. Your new partner may inject excitement. Your new career may offer unique experiences. Newness and novelty serve as effective distractions. When the honeymoon period wanes, your old challenges will re-emerge. They follow you wherever you go until you learn how to navigate them.

Take ownership of your shortcomings and the problems that result. See those issues to their resolution. That’s the only way to grow.

Hone a money skill.

Shortly after I turned 23, I put aside my nascent writing career. I had decided it wouldn’t make me rich, so why bother?

I regretted that decision for eighteen years.

In a moment of inspiration (or maybe desperation), I restarted my daily writing practice. That skill now generates a solid second income, which would have come in handy back when I flirted with bankruptcy.

Everyone who’s not rich needs a money skill — something that you can use to make money anywhere without the aid of an employer.

The specialized skills I’ve acquired from my day job lack utility outside a handful of employers, rendering them worthless. If you work a white-collar job, it’s likely the skills you’ve acquired aren’t transferable either.

For your own sanity and financial well-being, hone a skill that will earn you money.

The ability to generate income outside your main employment reduces the uncertainty and anxiety of being dependent on an employer for your financial livelihood.

Become a health freak.

Taking care of my health was one of the few decisions I got right in my twenties.

It happened by accident. Years ago, my roommate remarked that I had put on some weight. I was 26 years old and had never been overweight. It freaked me out enough to join a running club. Within months, it turned into a benign addiction.

To boost my performance, I took a keen interest in improving my diet and have continued that quest ever since, following the science, instilling harsh discipline in food and lifestyle choices.

Today, I enjoy the benefits of that decades-old decision, while some of my old friends now regret how they abused their bodies with drugs, alcohol, unhealthy diets, and lack of exercise.

Sadly, some are no longer around to regret youthful mistakes. Nothing will make you feel old like reading death announcements by family members of old high school friends.

“With a heavy heart, I must announce <insert name> has died from a sudden heart attack.”

There are no guarantees, but being maniacal about your health in your twenties and thirties will pay dividends in your forties and fifties.

Prune dead relationships regularly.

If you’ve lived a life dedicated to exploring new interests, visiting new places, and embracing new ideas, there’s an inevitable outcome.


Our worldviews shift, and we grow apart from the people in our lives. Even if you resist efforts to grow, circumstances will push and pull you in different directions.

That’s true of our friends and lovers too. Our lives diverge. In time, friendships and relationships become untenable due to growing differences.

When the time comes, it’s best to move on. Everyone knows the folly of sticking with a dead romantic relationship, but the same is true of friendships.

The wrong friends can hold you back. There, I said it.

You don’t need to cut friends out of your life forever, but you can relegate them to legacy friendships — people you engage with a few times a year but move outside your immediate circle.

Most friendships come with best used by dates. You can hold on past the recommended date, but the quality declines with each passing day.

Resist environmental brainwashing.

Before I found my professional footing, I secretly harbored extreme jealousy of friends who would show up to a bar at 11 PM, lumbering over straight from work, rubbing the bags under their eyes, crumbling inside on the verge of a nervous breakdown.

They’d bail on Sunday brunch to go into the office. The super cool ones would bring a suitcase of papers on weekend ski trips.

To an outside observer, that might sound like an awful life. Not so when you’re immersed in that scene. I felt insignificant and resentful because I lacked a soul-sucking job.

Seventy-hour work weeks signaled success and importance. On dates, you’d score bonus points if you spun a good story about your toxic job that spiked your blood pressure and sent you to a hospital. Tell your date that you were home by 6 PM every night, and they’d deem you a shiftless loser.

Finally, at the age of 31, I landed a job that deprived me of daylight. I had made it, joined the scene, and adopted a false belief of superiority.

Within a few years, I recognized what a load of bullshit these life-stealing workweeks were. I quit my job and found one with reasonable hours. Sure, I had to endure some of those stupid jokes from idiots who believed you were a loser if you weren’t working yourself to an early death.

By then, I didn’t care. I had learned a valuable lesson. Your environment influences your desires, beliefs, and worldview. Don’t underestimate its power.

Take a step back every so often, and ask yourself why you believe what you believe and why you desire what you desire.

Take advantage of desperate situations.

When I struggled as a salesman in my early thirties, I hired a mentor to help me. In one of our first exercises, he noticed my apprehension and fear.

He temporarily convinced me if I didn’t improve my skills, I’d lose my girlfriend, get evicted from my apartment, and wind up on the street. Once in that mindset, my submissive attitude transformed into one of assertiveness.

In the real world, it’s near impossible to sustain that kind of fake urgency. You can’t fool your brain. But as you progress through life, you’ll experience moments where losing equates to going broke, ending a relationship, or some other unfathomable loss.

During these times, we cling to safety, a lifeline, but that’s the wrong path. When you’re desperate to survive, act boldly.

In normal times, fear keeps us from taking giant leaps. We invent reasons to play it safe. That’s why you need to exploit situations where you can’t lose, where you must persevere. That’s when your survival instinct overrides your fear. Use those moments to your advantage.

You’ll still screw up. Don’t dwell.

No matter how well you play the game of life, you’ll blow opportunities, say things you wish you hadn’t, and play it safe when you should have gone bold.

Despite your best intentions, you’ll lose months, maybe years coasting through life instead of exploiting your fleeting existence. Acknowledge your mistakes, make amends, and do better the next day. That’s the catch-all solution to living a life without regrets — recognize the fallibility of being human.

Experimenter in life, productivity, and creativity. Work in Forge | Elemental | Business Insider | GMP | Contact: barry@barry-davret dot com.

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