Life Lessons Learned in My 40’s That I Wish I Could Tell My 20-Year Old Self

6 min readDec 27, 2020


Have you ever said words to the effect of If only I knew then what I know now?
You’re not the first person to express such thoughts, and you certainly won’t be the last.
Many of us are convinced that if we could go back in time and have a chat with our 20-year old selves, then we could absolutely kill at adult-ing and beyond.
A lot of growth occurs in our 20s. Yet, at 20, we convince ourselves we know everything we need to know and we’re ready to nail it.
It does beg the question, though, what would you tell your 20-year old self if you had the opportunity to speak to past you?

Debt Isn’t Normal
Let me finish! Of course, there’s normal debt, like your monthly mortgage repayment, car payments, etc. However, excessive personal loans and credit cards are not the way forward.
If you can’t afford to buy it with cash, then you have to ask how badly you need it. A credit card will help you build your credit score, but if you don’t know what you’re doing it will destroy it just as easily.
If I could advise my 20-year old self? Well, I’d tell him to educate himself about debt, finances, and money management.
Friends > Relationships
We’ve all been in relationships that absorbed us entirely. Suddenly, you have no time for friends or anyone other than this new romantic partner.
By the time you get to your 40s, you realize that you lose friends every time. You put them down, but when you try to pick them up again, they’ve already moved on. Then, it feels as though it’s worth it because you think you’re in love and you want to spend all of your time with that person.
The reality is that your romantic partner should want you to spend time with your friends because they should take time with their friends, too. If neither of you is doing this, then there’s a larger underlying issue.
Know What You Want

You can save yourself a lot of heartache if you take time to know what you want in a romantic partner, and don’t settle.
Movies and television give us this idea that love will be enough to get any relationship through everything. Those niggling doubts don’t matter, the annoying habits will fade into the background. However, little things like that start to become major issues when you’re with the wrong person.
What traits do you look for in someone else? Someone trustworthy, healthy, positive, and shares your core values?
Know what you want and don’t settle for less.
It’s been three months since you met up with your good friend, but you know they’re still your friend because you both try your best to keep in touch despite how busy life has become.
I wish I’d realized that sooner. That despite the fact that you see friends less often as you reach peak adulthood, your bond remains regardless. A friend’s a friend forever if you’re willing to put the work in.
As we grow older, people move away, they get married, they have kids, and they immerse themselves in their lives. While your inner circle might shrink, the other people aren’t just gone. You’ll be able to pick up right where you left off as soon as you meet up.
The Overrated Big Wedding

Yes, you want a major celebration. Yes, you want to make memories that last a lifetime.
But weddings get really expensive and no one should start a marriage in debt. There’s also the stress that wedding planning creates, which isn’t a great way to start a life together.
I’d tell my 20-year old self to curate the guest list to death and focus on a meaningful wedding and a great honeymoon.
Less Stuff Is Better
Do you hold onto old stuff just because you can’t bear to throw it out? Me, too. I’m guilty of collecting a lot of different things — shot glasses, ball caps, mugs from my travels… it doesn’t mean anything. It doesn’t add anything to my life.
You don’t need a closet packed with labels. You don’t need dozens of watches or a different pair of shoes for every day of the week.
Less stuff is better. Life is more meaningful than the things you own.
Manage Health
Your body is the only one you’ll have for life. It’s much easier to stay in shape when you were in shape to begin with. It’s much more difficult to get in shape when you’ve let yourself go a bit.
If I could, I’d tell my 20-year old self to be more careful weight training, kickboxing, playing soccer, and football. My body has taken a lot of hits over the years and because of that, I’m guilty of gaining more than a few extra pounds that I can’t shift.
This doesn’t mean I’m desperate to get ripped like The Rock. I’d just like to get up off the couch without every joint in my body crunching and cracking. If only I’d taken care of myself earlier.
Career Patience

This isn’t the best time to be starting a career. It wasn’t particularly great in my day either. I knew what I wanted to do, but my college career didn’t reflect that. That left me at a bit of a disadvantage.
I did get to where I wanted to go, but it took a lot longer than I expected it to. I struggled with anxiety and depression trying to catch my big break, and that negatively affected my relationship with my partner.
I’d tell my 20-year old self to be patient when it comes to career progression. Of course, I might also suggest studying something more appropriate at college, since I pursued what I wanted to do despite my degree.
There’s No Such Thing As Perfection
People brag about being perfectionists, myself included. But if I could go back in time and advise my 20-year old self, I’d tell him to knock it off because there’s no such thing as perfection.
It creates an impossible goal. One you’ll never achieve because you’ll never achieve perfection.
Chasing perfection will only lead you to one end, and that’s burn out. It may also prevent you from taking risks, too, because the fear of failure is too great.
Quick Lessons
It might hurt, but you should always tell the truth.
Not everyone will be as respectful and honorable as you.
No more hair gel!
Tell your parents you love them as often as possible, one day they’ll be gone.
You’re going to be fine!
Drink more water.
time you leave the house.
It’s okay to put yourself first and say no to the things (or people) that drain your energy.
Be open and honest about what you want, no one will read your mind.
Listen when people show you who they are.
You can have a degree and still be stupid.
You can’t get back the time you spend worrying.
Do what’s right for you, not what’s right on paper.
Some people will like you, some people won’t like you. That’s fine, you’re not for everyone and you don’t have to be.

Don’t forget to wear sunscreen every
Let yourself make mistakes, it’ll be okay.
Be tough.
Don’t waste your time on toxic people.
It isn’t things that matter, it’s people.
Be kind.
Before you go, grab a pen and index card, and take note:
“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.” — Steve Jobs