8 Ways For Men NOT TO Screw Up Their Twenties

Samuel Joseph
Unstoppable Masculinity
10 min readJul 20, 2022

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On my 29th birthday, I felt it…

My 30s loomed over me like a shadow.

I started to think about how much I missed out, all the things I never got to do, and all the straight jackets on my time.

That’s the vast majority of people.

But there are some people who aren’t too bothered about hitting the BIG THREE-ZERO.

These people have set themselves up to reap the rewards of working smart in their twenties.

There are a few critical things men need to figure out in their twenties, so they can hit their stride in their thirties.

For men, there are different rules than there are for women.

Abiding by these rules isn’t obligatory. They are completely voluntary.

Now that I’m moving out of my twenties, something is gnawing at me to leave some lessons for the young men who will follow.

I wish someone sat me down and told me this stuff when I turned 20. But then again, would I really have listened and taken it in?

Probably not.

But I have more faith in you, dear reader, than I do my twenty-year-old self.

(And, if you’re in your 30s, don’t worry… Don’t judge yourself. Just pick up where you left off…)

There are very few things you do that are completely fatal in life. Wherever you are now, you are completely redeemable.

So long as you know what to look out for.

And if I’m being completely honest, there are a couple things on this list that I am still working on, too.

But I’m a hell of a lot further than I was ten years ago… and richer for it.

The most important thing is to be aware of these lessons, and take a little step toward them every day you can.

You may not know this… But it’s critical to realise that…

Men typically peak in their 30s.

A man’s life in his twenties is a process of getting his 💩 together, building skills and becoming capable.

Here are some critical lessons for men in their twenties…

1. Pick something you want to get good at

Lots of people think following their passions means they can avoid the drudgery of a 9 to 5 office job. I feel sorry for them… because they are in for a shock.

It’s much better to pick a purpose first. The passion comes later.

Think about it: Everything you are passionate about is something you are GOOD at.

At its basic level, it’s something you know a heck of a lot about.

That’s because when we get good at something, we always enjoy it.

So pick a career that lets you get better at something you care about. For me, that career is writing.

You won’t feel “passionate” about it when you start. But your will grow as your skills do.

2. Figure out your strengths

Good ‘ol Peter Drucker famously said never work on your weaknesses, increase your strengths instead.

If you focus all your time and effort trying to get better at something you suck at, you’ll have spent all your energy being mediocre at best.

Now, this doesn’t mean you should ignore a weakness that’s causing you pain… But it does mean you should patch it up fast so it’s not a hindrance anymore…

Then get back to working on your strengths.

If you don’t know what your strengths are, a good way to find out is to ask your friends and family…

“What do you think my 3 biggest strengths are?”

Another thing that I’ve found helpful is taking a “Strength Finders” test and a personality test at Psychology Today.

These tests aren’t free… But I can tell you they are worth their weight in gold.

3. Reach for competence and the status will follow

This is gonna sound sexist… But I gotta be honest with you….

A big part of a man’s value is due to what he can provide.

That means it doesn’t really matter how great your personality is, how handsome you are, or how much intelligence you have.

All those things mean nothing unless they are making you money.

Sorry. It sucks, but it’s reality.

Competent men get paid the most. They have more women chasing them. They have less stress and high social status.

What that means for you as a young 20-year-old is…

You gotta put in the work to be really good at your career.

If you don’t, you’ll be fine for a little while.

But you will find that when you hit 30… There will be a big glass ceiling on your progress.

Opportunities will start to dry up. Women will stop showing interest in you, and your career will stagnate.

*Note: Chase a career! A job is what you get paid to do. A career is what you do to become something better. And careers always pay more than jobs.

4. Think about what 30-year-old you would ‘high five’ you for — and do it

People love to procrastinate.

Evolutionary biologists claim that it’s our lizard brain trying to get us to conserve energy.

Now, I’m not telling you to avoid procrastination. But I am saying that there needs to be something that is sacred — that you never put off for any reason.

This concept is called delayed gratification. It means you exchange a small payoff now for a bigger payoff in the future.

How this works for you is…

Say you want to learn a new skill that will give you a leg up in your career.

You’ve found a course that will teach you the skill, but it’s a hefty $1,000. On top of that, you’ll need to dedicate a couple hours each week to learn the material.

What’s the cost? $1,000 plus 5 hours a week, for 6 weeks.

But there are unseen costs too…

That $1,000 for the course means you can’t spend that on a new suit, going out with friends or taking your girlfriend out for fancy dates.

The 5 hours a week means you can’t watch Netflix, flip around on YouTube or go pub crawling with your bros for 2 and half months.

Are you willing to sacrifice all those fun things now, to get the skills that will let you have more money and time in the future?

That’s for you to decide.

Remember, when you’re 30 years old and thinking back on your life.

What will you want to ‘high five’ your 20-year-old self for?

5. Pick a hobby

“All work and no play makes Jack a dull boy” — The Shining

You need something that you do for yourself, just for the pure enjoyment of doing it.

Some people like exercise, others like art, playing a musical instrument, or whatever…

The truth is, you need a creative outlet to engage your brain in a different way.

There needs to be something in your life that brings a bit of stillness and joy.

Something restful and NOT career driven.

A hobby gives you a framework to deal with life.

It gives you metaphors and perspective… And more importantly, it fills you up with energy to face the tough parts of life again.

6. Decide what kind of partner you want

As a man who has goals and is chasing a purpose…

You have to be picky about what kind of partner you let into your life.

I’m talking about a long-term partner here. Have flings and relationships with whomever you please.

But if you are picking someone to do life with… They better be someone who won’t detract from your purpose.

Often, men will get a partner because they’re ‘HOT’ and ‘FUN’ to be around.

Then, their partner will start requiring more time, attention and focus… leaving the man to ditch a lot of his goals and spend his energy on her.

I’m going to tell you something that possibly flies in the face of ‘modern virtuous wisdom’…

Here it is:

As a man, your first priorities are your goals, purpose and growth.

Then far back in second (maybe third) place is your partner.

Your partner SHOULD NOT be the centre or the focus of your life.

If you make them your focus, they lose all respect for you and see you as a chump with no vision.

And the truth is… if you let that happen, you are a chump with no vision.

You’ve abandoned what’s important in your life for someone else’s whims.

That’s not being virtuous — it’s being weak.

If you want a woman of value, you have to be a man of value first.

Sorry for that harsh medicine, boys…

But I’m just telling you what I would tell my 20-year-old self if I had a time machine.

Just think of all the years of heartache you’ll save if you take this advice and live by it.

7. Tell the truth and stick to your word

When you’re in your twenties, you tend to be a people-pleaser.

It’s natural.

But be careful you don’t slip into being flimsy with your words. It’s ok to say yes to things and have a ‘can do’ attitude. But you gotta know your limits and stick to them.

For instance, you can’t do more than you can do. So don’t try to impress people by giving them the impression you are more capable than you are.

You may not know it… But you have a lot of leeway in your twenties. People tend to cut you some slack and forgive more mistakes.

You’re in the best position you will ever be in to say “I DON’T KNOW.” Use that advantage.

The other part is, you don’t want to break promises, especially in your career.

If you say you’re going to get something done… and you’ve drastically under-estimated the size of the task…

Guess what? You are going to have to work overtime, likely with no extra pay to get it done.

You need to back yourself when you give someone your word.

Otherwise, you will be BRANDED as someone who is flimsy and unreliable.

Telling the truth is more than about doing what’s right. It’s about protecting your reputation.

It’s also very difficult, because you may have to tell people things they don’t want to hear.

This may give you some heartache when you first do it.

But the older you get, you soon realise that it’s far better to be known as someone who tells the truth than someone who tells you what you want to hear.

8. Speak less — Now’s not the time for your opinions

There’s a lot of empowerment and self-help speak that tells people to LET THEIR VOICE SHINE.

What a nice fluffy message. But there’s one caveat…

How do you know that you have something valuable to say?

For men in their twenties… I’m sorry, but it’s likely you don’t have much value to add. Especially if all you have is an opinion.

I know you FEEL like you want to contribute. But don’t contribute with words, do it with actions. They are far more valuable when you have limited skills (which you do in your twenties).

And by all means, ask questions. But don’t believe that adding in your opinion has any kind of worth.

You have not had any kind of skin in the game. Most of your life has been sheltered, and you rely on someone else to pay you — from a business they created.

So don’t get too self-inflated. Your opinion doesn’t mean squat.

You have to earn that right And it takes years.

And you will earn it over time — be confident about that! People always need help, and it’s a special privilege to be asked for advice.

When your advice is solicited, you want to be confident you know what you’re talking about.

Don’t let your un-tested opinions steer some poor soul into an abyss.

More pressingly, don’t let your limited view of the world steer you into one either.

Life is long… especially if you’re not prepared

The period between 20 and 30 is the ‘apprenticeship’ stage for men.

We all want ‘success’ as fast as possible… But what I’d have you think about is this…

Success is merely the symptom of your skills and attitude.

That means, your REAL success comes later. Don’t sell yourself short by settling for what you can get now!

Build your foundation. Take your time, and make yourself into someone you can rely on.

A house built on sand can’t stand up in the storms. But a house built on stone can face a hurricane.

And there are lots of hurricanes in life.

When you’re young, dumb and full of gusto…

You can forget life is long and difficult, especially if you don’t have most of these lessons under your belt.

But I believe that once you know what to aim for, you can achieve anything you want.

I’ve proven it in my life.

And there’s no reason you can’t prove it for yours.

Get rid of a crippling habit most men will carry for life

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