If You Want To Be Happy In Your 40’s…

Learn from the subtle “life” mistakes of your 20's

Photo by Ben White on Unsplash

Life is a succession of lessons which must be lived to be understood — Ralph Waldo Emerson

It’s a common trope in sitcoms, movies and plays. A supernatural being gives you a chance to go back in time and change an event from your past. Most choices center around a missed opportunity, the avoidance of a painful experience or a decision with devastating consequences.

If someone gave me that choice, I would try a different approach. Instead of changing a past event, I would transfer my accumulated wisdom to my twenty-one-year-old self. Perhaps that would have enabled me to make better decisions in my twenties and thirties.

The most important lesson you learn as you near fifty is that your worst mistakes aren’t those individual decisions where you turned left instead of right.

Arrogance, stubbornness, fear, and closed-mindedness caused the most misery for me in my youth.

I feel fortunate to have recognized these problems and rectified them. I see other people my age clinging to the same arrogance they possessed as young twenty-somethings, fearing the same things, closing their minds to new ideas and perspectives, and always trying to keep the world from changing.

These peers don’t look happy. They sport a look of resignation like they missed their chance at life and now they’re holding on for survival.

These lessons have helped me stave off that demise.

1) Don’t let people take advantage of you

During my early twenties, I let everyone in my professional life take advantage of me. It was a near epidemic.

I worked at a hotel, making a decent hourly wage. They promoted me to a manager title to avoid paying me overtime and then bumped my hours up to sixty per week. It was exploitive but common practice at this hotel.

But then they promoted me again. They “rewarded” me with a salary increase of $1,000 per year. (it wasn’t much, even back in the 90s). I was soon working seventy hours a week. I complained to my boss, and she said, “we gave you an extra $1,000 per year, and now you’re complaining.”

I apologized and nearly killed myself working insane hours.

My next boss decided to waive my annual review and merit increase because I was new to his department. It was against corporate policy, but I acquiesced with barely an objection.

My frustration mounted and I quit abruptly. I gave two weeks notice but didn’t show up to my scheduled shifts. When my boss called after a no show at work, I vented my frustration at him.

Everything I had wanted to say to him for months came out in a flurry of tongue lashings. That’s what happens when you let people walk all over you for too long. The pent up energy escapes like a popped champagne bottle.

Why was I so submissive?


I feared losing my job.

I feared a disparaging reputation.

I feared they would label me a problem.

When I quit, I hustled my way to a new career at a company with nicer people. It may not have been the best way to find my backbone, but it worked.

Stand up for yourself once, in a situation where you have something to lose. Assertiveness will come easier to you from that moment on.

2) Understand the real value of passion

The pursuit of a passion brings you happiness, fulfillment and purpose.

I started to write my first book at the age of twenty-three. I gave up on it after six months, frustrated by my perceived lack of progress.

“It’s not making me any money,” I decided.

I concluded that my petty passion was a waste of time. Back then, I believed that if it didn’t bring in revenue, it was a hobby, and hobbies were for losers.

I thought that money was the only form of currency worth pursuing.

Three years later, I made a pact with my friend. We both decided to train for a marathon. My friend quit after a month, but I stuck with it. For the first two years of my running career, I ran alone.

A combination of boredom from solo running, a lackluster social life and non-existent dating life prompted me to join a running club. I was twenty-nine at the time, and it was one of the best decisions I ever made. Running became a passion, a lifestyle. I met some of my best friends and my future wife from my running world.

It taught me a valuable lesson about passion.

Money is just one form of currency. Connection, love, fulfillment, belonging and self-awareness are all valid forms of reward for pursuing your passion.

3) Don’t take friendships for granted

I’m still grappling with this mistake over twenty years later. I had a lot more friends when I was younger, tons in my twenties. Today, I have lots of acquaintances and only a few close friends.

Friendship is a two-way street. The responsibility falls on both parties to maintain it. Still, I could have done more to keep some of those lost friendships. I always thought there would be more opportunities for friendships like it was a spigot you could turn on and off as needed.

It doesn’t work that way, especially as you age and take on more responsibilities. Nurture your friendships. Don’t take them for granted.

4) Let go of arrogance

The older I get, the more I become aware of my ignorance. God, I miss my twenties. I knew everything with a surety that bordered on arrogance.

If you expose yourself to new information, new people, new perspectives and new experiences, you’ll realize you were wrong about things you were once sure about.

You’ll realize that some of your deeply held beliefs originated from your childhood and teenage years. You’ll understand that those beliefs were never vetted or verified.

You’ll poke around and find contradictions. At some point, you’ll experience that epiphany. “What if everything I’ve been taught is bullshit?”

At that point, you have two choices. Ignore the dissonance and continue your life as though you were still a know-it-all.

I hope you’ll take the second path.

Question your deeply held beliefs and scrutinize them. It’s uncomfortable, time-consuming and tedious, but the joy of enlightenment makes it worth it.

5) Don’t let an unsuccessful relationship deter you from trying again

We were friends first and then dated briefly. I was in love; at least I thought I was. Then she dumped me for someone more culturally aligned with her.

“We come from two different worlds,” she said. “It’ll never work.”

She still wanted to be friends. I told her I would never speak to her again.

I vowed to myself I was done with relationships. “That’ll show her,” I said to myself. Never mind that she had no clue I had made this secret vow to myself.

The only one who suffered was me. I’m happily married now, but I wish I hadn’t been so childish back then.

We reconnected years later, and now we’re Facebook friends (if that really is such a thing).

6) Don’t hurry your way through life. Savor it

Everything had a deadline in my twenties (and thirties).

I had mapped out how much money I wanted to make every year for ten years. I penciled in the job titles I would notch and the material goods I would acquire.

My running passion turned into an obsession at times. It irked me when someone had run more races than me, faster times than me, or traveled to exotic running venues.

The occasional injury from my obsession brought me back down to earth, but I wish I had spent more time savoring and enjoying the fun times rather than rushing through them and checking off imaginary boxes.

I did fun things in my twenties, but I rarely had fun.

I spent too much time trying to achieve arbitrary goals by arbitrary deadlines. It made for a stressful life, always worried and fretful over a missed goal. It wasn’t until my late thirties that I learned to step back and enjoy the small moments.

Enjoy the small moments, they’re the only ones you’ll remember twenty years later.

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

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