10 Things I Wish I Knew at 20: Life Lessons Every Man Should Know

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by  Jack Garden | Last Updated: 

Hindsight is a wonderful but frustrating thing.

There are a ton of things I’ve learned since turning 20. Things that I’ve discovered in hindsight and wish I knew five years ago.

Unfortunately, that’s no use to my 20-year-old self. And without the invention of time travel, it never will be. 

And though I’m hardly a wise old sage at 25, I know a thing or two about growing up as a millennial and the transition into adulthood.

So here’s 10 things that I wish I knew at 20. 

Take Your Time

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I get it. 20 is a stressful time.

With pressure and options coming from all sides, it seems counterintuitive to slow down.

The world is telling you to get your ass in gear but I guess what I’m telling you to do is put your foot on the brake a little.

When I was 20, I rushed off in the wrong direction (career wise). 

But if I’d slowed down and taken some time to really assess myself and what I wanted to do. Maybe I wouldn’t have spent two years chasing the wrong dream.

After all, what’s the rush?

You may as well take your time now, while you have it on your side. 

This way you’re more likely to pick a pursuit you actually enjoy. Rather than getting stuck in a career you hate.

Take your time, live a little and have some fun. You’ll figure out the big stuff later.

It’s OK to be Lost

You don’t know what you want to do?

So what?

Who does at the age of 20?

Most people think they do but most people are wrong. You’ll likely change direction multiple times throughout your life.

I’m only starting to truly settle on my passions at 25. And even now, I’m far from certain.

I must’ve been through close to 10 career ideas in my life already. From wanting to be a soccer player as a kid, to an actor at 20, now a writer at 25.

A few other honorable mentions include ski instructor, the army, a model and a hermit living in the wilderness. 

I can’t lie, that last one still appeals to me but where’s the common ground between any of those? I’ve been all over the place with my career.

But you know what? 

It doesn’t matter.

All of us get lost sometimes. It’s perfectly normal. 

Not knowing what you want at 20, 25, 30 or even 40. Is perfectly fine. 

Super frustrating, but fine.

Knowing that when I was 20 would’ve really taken the pressure off. And knowing that I wasn’t alone would’ve been a comfort.

Be a Little Selfish

I’m guessing that you’ve got a lot of opinions in your life right about now? 

Parents, grandparents, aunts and uncles all offering their two cents on what’s best for you.

While it’s important to respect these opinions—most people are just trying to help you. The only person who ultimately knows what’s best for you is you.

Now, I’m not saying don’t listen to your parents. Turns out they do often know what they’re talking about. Who’d have thought it?

But don’t do what others are telling you to do simply because they’re telling you to do it.

A big part of being happy comes from trusting yourself. Knowing that you know what’s best for you.

Whether that’s following an unpopular career path or turning down an invite to that party for a little you time. 

Essentially, you do you.

You’re Going to Fail Sometimes—But That’s a Good Thing

Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing and being nothing. Denis Waitley

We all fall down. The important thing is that we get back up.

At 20, you have a lifetime of failures ahead of you. 

Exciting stuff, right?

You’ve got mistakes to make but also lessons to learn.

Failing is the only way in which we grow.

So don’t be afraid to fail. Welcome a mistake because you’ll learn from it and become a better man.

And through becoming a better man, you’ll drastically improve your life.

School is Not the Best Time of Your Life

Did your teachers ever say that to you? Mine certainly did.

But you know what. It’s BS.

School has a lot of good things going for it, but the best time of your life? C’mon.

Truth is, life gets way better after school with a little hard work and the right choices. 

So don’t buy into that trash about school being the best thing ever. There’s plenty more excitement on the way.

Stick at Things

Some things are worth sticking at.

I look back on the last 10 years of my life and wish I’d stuck at a few more pursuits during that time. Because they’d be useful to me now.

You’re going to change constantly throughout your life. Never more so than when you’re young.

Something that 20-year-old you thinks is pointless now, might be super useful for you at 22, 23 or 24.

Take me as an example. 

I ran a website for over a year before giving up on it. Now it’s getting a ton more traffic but is inactive.

If I’d have stuck at it for another year, that website could easily be making me money by now.

You Don’t Need to be in a Relationship Yet

The pressure to have a girlfriend/boyfriend at this age can feel huge. But you really don’t need one.

You still have so much development ahead of you, and in all likelihood, you’re not the best version of you.

Looking back now, to 18, 19 or 20-year-old me. I can’t help but think—god, that guy wasn’t ready for a relationship!

I wanted one desperately, but I would have been a terrible boyfriend. 

I still had a lot of growing up to do, and a relationship would have been more of a burden than anything else.

Look at the Big Picture More Often

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At 20, life seems so zoomed in and pressurized.

Everything is about making key decisions that will influence the rest of your life.

It’s easy to get caught up in the stress of these seemingly huge decisions. So it can be a relief to take a step back and look at the big picture.

These decisions you’re making now, these actions you’re taking. Aren’t the be all and end all.

Looking at the big picture makes you realize life isn’t as serious as you think.

Your life is going to be fine regardless of what you do when you’re 20.

That’s not to say that you can’t mess up your life at this age. You certainly can.

But know that you can always fix it.

Be Grateful for What You Have

20 is a time of wants. 

I want to get into this college. I want this job. I want to be in a relationship.

But it’s also a time to be grateful for.

While you’re busy thinking about everything you don’t have, it’s easy to neglect the things you do.

Being grateful for what you have will not only attract more of the same, but it’ll boost your mood and give you a more positive outlook on your life.

You’re Not Special

The younger generations—mine included, are generally raised with the belief that they can have anything they want in life.

There’s a famous talk on this by Simon Sinek.

He gives several of the reasons in the video above, and I have to agree with him.

As a 20 year old, I was entitled. I thought I was special.

I had these huge ambitions but wasn’t doing any work towards them. I guess I thought they would just land in my lap.

Of course they didn’t.

Turns out I have to work hard to achieve anything in life. 

Who knows where I’d be now, if I’d learnt that at 20.


I have much more to learn, but these are the 10 lessons I wish I had learnt a little earlier in life.

Check out our Lifestyle category for more actionable life lessons that you can apply today.

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