There’s something about looking backward that changes the way we look at our younger selves.
At 20, we think we’re grown. We may have a job, be in college, serving in the military, building a relationship, or trying to figure out what we’re going to do with our lives. We make decisions based on what we know at the time, what we want, and sometimes what the people around us expect from us.
Then life happens.
Responsibilities get bigger. Families are built. Careers take unexpected turns. Money gets tight. Dreams get put on hold. And sometimes, before we know it, we’re much older and wondering what happened to some of the things we once imagined for ourselves.
So I decided to ask four Gen X men a simple question:
If you could sit across the table from your 20-year-old self, what advice would you give him?
Their answers weren’t complicated. In fact, they were practical and some made me think about how much hindsight can teach us.
Jamal (52)~ “Finish school ASAP. Focus on your money and being a millionaire by 30 years of age. Don’t listen to people that are afraid and don’t share the vision you have. Find a mentor! Find a mentor! Find a mentor! Stay grateful! You and Family are always number two. God is always number one. Oh! and don’t chase a woman. Only pursue a woman that is aligned to your principles and wants to join you in your life journey.”
Kevin (59)~ “Slow down and take your time so you’ll fully understand instead getting it done like it’s a race. Microwaved meals done in 5 minutes will never taste better than dish from the oven.”
Jaysun (50)~ “Stay in the army and let them pay for your education. Streets will be dead in 10 years.”
Julien (45)~I regret that I didn’t take playing Basketball more seriously. I would tell my younger 20 year old self to work on your jump shot and take basketball seriously because I had the height and work ethic to achieve. I just didn’t take it seriously.”
Sometimes, our biggest regrets aren’t the things we couldn’t do. They’re the things we believe we could have done.
And that made me think about how many people reach midlife carrying a list of “what ifs.”
What if I had finished school?
What if I had started the business?
What if I had taken my talent seriously?
What if I had saved more money?
What if I had listened to myself instead of everybody else?
What if I had pursued the thing I really wanted instead of choosing the safer path?
And that brings me to the part of this conversation that I find especially interesting as a woman looking at the lives of men in my generation.
The weight of being “the man”
I don’t want to speak for every Gen X man, because everyone’s story is different. But I do think it’s worth acknowledging the cultural expectations many men grew up with.
Be the provider.
Be the protector.
Be the head of the household.
Take care of your family.
Be strong.
Figure it out.
Don’t complain.
Don’t let anybody see you struggling.
That’s a lot to put on one human being.
For some men, those expectations may have been motivating. For others, they may have created pressure that affected everything from career choices to relationships to their mental health. What happens when the man who is expected to provide doesn’t know what comes next? What happens when he wants to change careers but has children depending on him? What happens when he wants to start a business but doesn’t have the financial cushion to take the risk? What happens when he’s struggling mentally but has spent his entire life being told that asking for help isn’t what strong men do? What happens when the dream he had at 20 conflicts with the responsibilities he has at 40 or 50?
These aren’t questions I can answer for the men I interviewed, and I wouldn’t want to assume their individual experiences.
But they’re questions worth asking.
Because finances and mental health can have a tremendous impact on the choices people make. And when you add the pressure of being responsible for a household, a partner, or children, sometimes survival takes priority over fulfillment. You may not abandon the dream because you stopped caring about it. You may simply put it on the shelf because somebody needs you.
There’s a difference.
Maybe this is what getting older teaches us.
We don’t always become the people we thought we’d become at 20, however, some people do by finding their way back to an old dream, or discovering an entirely new one. And some are still figuring it out.
Some are finally giving themselves permission to admit that the definition of success they inherited isn’t necessarily the definition they want anymore.
Maybe success at 20 was about making a certain amount of money. At 50, it might be about having peace.
Maybe it was about being the provider. Now it might include learning how to receive.
Maybe it was about proving yourself. Now it’s about knowing yourself.
Maybe the goal was simply to survive.
Now the question becomes: What do I actually want to do with the life I have left?
And I think that’s where this conversation gets really interesting.
Because these four men didn’t just give advice to their younger selves. Their answers revealed four different lessons about adulthood:
- Take your gifts and opportunities seriously.
- Don’t let other people’s fears dictate your vision.
- Slow down enough to actually understand your life.
- Seek guidance instead of believing you have to figure everything out alone.
- Pay attention to your money because financial freedom creates choices.
- Don’t lose yourself while fulfilling your responsibilities to other people.
- And perhaps most importantly, don’t assume that getting older means it’s too late to change direction.
Sitting across the table from our younger selves
As a Gen X woman, I can’t help but think about what I would tell my own 20-year-old self, because I have my own list.
There are things I know now that I couldn’t have possibly understood then, aAnd that’s the strange gift of getting older. We finally have enough experience to see the decisions we made with more compassion. We were young and didn’t know everything. We were trying to make good decisions with the information we had.
The same can be said for these men.
That 20-year-old man didn’t know what his 40- or 50-year-old self would need.
He didn’t know which opportunities would matter.
He didn’t know which dreams would stick around.
He didn’t know which responsibilities would eventually compete with his own desires.
He was just trying to figure it out.
Aren’t we all?
Maybe the point of asking what we would tell our 20-year-old selves isn’t really about wishing we could go back, because we know we can’t. It’s about listening to what that younger version of us might still have to say.
Maybe he would remind you about the dream you abandoned.
Maybe he’d tell you to take yourself more seriously.
Maybe he’d tell you to slow down.
Maybe he’d tell you that money matters, but it isn’t the only measure of success.
Maybe he’d remind you that you’re allowed to ask for help.
Or maybe he’d simply say, “You still have time.”
And perhaps that’s the message I take away from this conversation.
We’re Gen X.
We’ve already lived through enough to know that life rarely follows the plan…but we’re also not done. There are still dreams to explore, mistakes to learn from, opportunities to recognize, and chapters to write.
So maybe the question isn’t only:
What would you tell your 20-year-old self?
Maybe we should also ask:
What is your 20-year-old self still waiting for you to do?
