Journal Entry

30 Brutal Truths I Wish I Knew in My 20s

For years, I thought I was doing everything right.

I read the books.

Set the goals.

Hustled hard.

But no matter what I did, I felt stuck.

Spinning my wheels.

Second-guessing every move.

Turns out, I wasn’t missing more motivation…

I was missing the truth.

The brutal, uncomfortable truth that nobody tells you. The kind that stings at first but sets you free forever.

At 33, looking back at my 20-year-old self, I see a kid who needed fewer inspirational quotes and more reality checks.

If I could go back, here’s what I’d tell him.

Welcome to Refusing to Settle Saturday. Where we talk about transforming your life and unlocking You 2.0.

Here’s what we’ll cover

The surprising reason you’ll regret inaction far more than failure
Why “healthy” looks boring and why that’s exactly what you need to embrace
The 10% “tax on yourself” that would have made me rich by 30
My hot take on burnout that nobody tells you
Why you need to stop waiting for life to get easier
The Best Relationship Advice no one ever told you

1. Don’t kill the part of you that’s cringe, kill the part that cringes

Those who never experience anything cringe are trapped by their own judgmental inner critic, and I promise you, they’re never going to create anything remarkable. I’ve seen this firsthand with so many talented people who never ship their work because they’re afraid of judgment.

Be easier on yourself. Embrace the cringe, don’t take it too seriously, and life will be more fun.

2. If you’re thinking too much, you’re not acting enough

It’s tempting to think, “If I can prepare a little more, do a little more research, then I can avoid failure or looking dumb.” But it’s the thinking that’s causing problems.

You overthink what to say and come across as awkward. You overthink what to write and it doesn’t sound like you. You overthink what to do with your life and you remain stuck while others pass you by.

You can never overthink your way out of action-based problems. Try creating something, anything, to get you unstuck. Action is the only way you escape overthinking.

3. Get insanely good at something

I got obsessed with drums, got good, and ended up touring the world with a band.

I got obsessed with content creation, got good, ended up making it my full-time job.

When you get good at something, you’re learning the meta-lessons of how to learn. And while it might not be the thing you do forever, you get to take all the skills you earn into your next thing. So dive into something: coding, design, art, sales, content, fitness. Pick something and have fun learning how to learn.

4. Stop waiting for life to get easier

The trick your mind plays is thinking, “I just need to get through this stage… the next one will be better or problem-free.”

But EVERY stage of your life has its own set of problems. Teenage years, college, adulthood, retirement.

And I guarantee you once wanted to be at the stage you’re in right now at some point in your past. Remember when you couldn’t wait to be an adult? Then you’re an adult and wish you were a kid again.

So the brutal lesson I’ve learned is to stop waiting for life to get easier. Life never gets easier… you get better with more experience.

5. You will regret inaction more than failure

For every person who regrets a failed business, there are a thousand who regret not even trying.

For every person embarrassed for asking someone out, there are 10,000 kicking themselves for not shooting their shot.

The only way your life can drastically change is by embracing rejection as part of success. The people you look up to have one thing in common: they’ve failed more.

So next time your fear of failure creeps in, remember this: at the end of your life, you won’t regret what you did… you’ll regret what you didn’t do.

6. The most important thing for happiness is relationships

The longest study on happiness spanned over 80 years and tracked over 700 people, asking them one question: what truly makes us happy?

You know what they found? It wasn’t fame, wealth, or hotness. Time and time again, it was the quality of your relationships.

And it’s not about having hundreds of them but having a few very close people you go through life with. So prioritize people, not things, to be truly happy.

7. People aren’t against you, they’re just for themselves

Did they not text back because they hate you, or do they just have their own things going on?

We’ll never know for sure, but the point is not to waste energy coming up with reasons why people did things.

The quicker you stop taking things personally, the faster and more energy you’ll have for yourself.

8. Burnout isn’t about doing too much, it’s about doing too little of what actually matters

If we never do what we love, who wouldn’t be burnt out?

My hot take on burnout:

you’re not burnt out from doing too much, you’re burnt out from doing too little of what matters.

When I was stuck in jobs I hated, even 20 hours felt exhausting. Now I can work 50 hours on things I love and feel energized.

9. You teach people how to treat you

It can feel uncomfortable to advocate for yourself, and setting boundaries can feel awkward or intense at first, but you get what you tolerate. Whether that’s at work not advocating for yourself, in relationships letting people walk all over you, or friends letting them flake.

This works in the affirmative too – praising the qualities you want to see growing in people. Be sure you’re rewarding the right behaviors from others.

10. Keep a journal

I’ve invested in therapists, coaches, programs, live events, and masterminds… but I’ll let you in on a little secret. The best self-growth came from sitting down with my journal. Learning to coach yourself is invaluable. You develop this through journaling.

I think there’s something so cool in a digital age having an analog system where you can see your handwriting, it’s unplugged, you can take it everywhere with you, and you can look back on it in 10 or 20 years. Imagine that.

(Our journal program drops next month, so stay tuned for launch details!)

11. Focus on big wins around money in your 20s

Earning more money is way easier than saving money.

Can you negotiate your salary every 6 months, earning a couple extra grand each time?

Can you get a side hustle making $200-300 extra weekly?

If you’re stuck in a low-wage job, can you learn a trade and be making six figures in a couple years?

Sure, cutting out $5 lattes helps, but not spending an extra $10-20K on a new car when a used one works fine helps even more.

The point is, give your energy to the big money things, and the small things start taking care of themselves.

12. Starting today, put a 10% tax on yourself

Ready for another financial brutal truth?

By the time I was 25, I had worked over 20 jobs and you know how much money I had saved up? Zero. In fact, I was negative net worth… I was over 30k in debt.

That’s when I had a hard reality check: why did I work to begin with? It was to get ahead, but I wasn’t.

That was my wake-up call. I made a commitment that no matter what my financial situation was, I’d find a way to at least put something aside. Even if it was a hundred bucks a month.

I definitely could have lived on 90% and saved the other 10%.

Look into compounding and investing and the benefits you have of being young. No matter how much or little you make, put away 10%. View it as a tax on yourself so you’re always building and getting ahead.

13. Be incredibly mindful of alcohol

I’m not saying you shouldn’t drink. I did in my 20s and made some memories I’ll never forget (and a lot I can’t remember lol). But partying has an expiration date, and those who stay at the party too long get left behind in life.

Going sober for me was the best decision I could have ever made. You’ll grow in ways you don’t expect, you’re going to make real friends (not just drinking buddies), and you’ll build a life you actually love, not one you need to escape from. So it’s okay to go to the party, just know when it’s time to leave.

14. Accept that healthy looks like boring

Long-term healthy relationships can seem boring compared to the exciting short-term fling that’s toxic.

Long-term healthy diets that are good for you can seem boring compared to the latest trend where you lose a bunch of weight and gain it back, which looks exciting.

And the routine you need to save your first $100K looks really boring compared to the latest meme coin pump.

The point is, that there’s excitement and buzz you will hear in extremes, but most of the time, your results are in sustainability. So accept that healthy looks like boring, but that’s totally okay.

15. Life’s too short for bad slee

Invest in blackout curtains, wear an eye mask, wear a tracking device so you get data on your sleep (I use Oura Ring.)

Since taking my sleep seriously the last 5 years, I’ve never averaged below an 80 sleep score. Gamify the process of sleep, make it fun, and watch your energy go through the roof.

16. You’ll never be good enough for the wrong person

Relationships aren’t 50/50, they’re 100/100.

If someone doesn’t see your worth, stop trying to convince them. I spent years trying to prove my value to people who couldn’t see it, and all it did was drain me. Save your energy for those who already recognize what you bring to the table.

17. You don’t need energy to work out, you get energy by working out

Your body is designed to move, so even something as simple as a 30-minute walk or standing for a few hours a day can drastically boost your energy levels. The key is finding exercise for you that doesn’t feel like work and that you have no resistance towards.

Join a rec sport, go to the gym, try a class. The secret is finding the kind of movements that you have zero resistance to doing.

18. You are the main character of your movie. Document it.

I don’t mean for social media, I mean for yourself! All your cool behind the scenes moments. Document more, take more photos, record your thoughts in your journal.

Here’s an easy habit you might consider picking up: Every birthday, sit down with a camera and for 20 minutes just process through your life. Talk about three things: highs, lows, and changes.

I get so much out of reading old journals and watching my old videos. And 20 years from now, looking back on those, you’re going to be so glad you did.

19. Stop looking for the right person and start trying to become the right person.

This is the best relationship advice I ever got in my 20s: Tens attract tens. Like attracts like. If you want to attract someone on a higher level, you need to raise yourself up to a higher level as well.

When you stop looking and searching and you worry about becoming, you find that that person magically comes into your life.

20. Get a dog

This is the sign you’ve been waiting for. Dogs force you to live in the moment, get outside, meet people, and pick up poop at 6am. I got mine at 28 and honestly, I wish I hadn’t waited so long – the reward outweighs the work tenfold. Taking care of something and putting the focus off of you is great for your mental health.

21. If you’re going to compare, you need the full context

Social media has made it literally impossible for you not to compare yourself to others, and if you’re not careful, everyone’s hot, everyone’s successful, everyone has tons of money, doesn’t work, and can travel all the time.

But when we compare, we’re never getting the full story. I’ve seen so much behind the scenes – like the couple who everyone admires that can’t stop fighting when the cameras are off, or the fitness influencer who’s “all natural” but is taking a little “special sauce” behind the scenes, or the entrepreneur who works all the time whose kids barely even know them.

We never get the full story to compare to. You might actually have a better, well-rounded life than the people you’re comparing to who’ve achieved one-dimensional success.

So use success as inspiration, but not as ammunition to feel bad about yourself.

22. Start making weekly to-do lists

If you have five things you need to get done that week, and they’re the only five things on a list, it’s very hard to procrastinate. When I switched to weekly to-do lists and only put on there what I needed to get done for the week, my productivity skyrocketed.

23. Practice zero-based thinking.

Ever stick with something because you put so much time into it already? Anytime you feel yourself feeling stuck, stop and ask yourself this question:

“Knowing what I know now, if I could start over today, would I still _______?”

Would I still be in that same relationship?

Would I still choose the same career path?

Would I still live in the same city?

If the answer is no, it’s time to switch things up. Don’t ever let momentum carry you away in a direction you don’t want to go.

24. Find a way to travel

In my 20s, I backpacked solo through 12 different countries, toured the world in a rock band, and had the adventures of a lifetime. I was able to meet incredible people, and experienced firsthand how traveling changes your worldview. Yes, I had to work odd jobs and save up money, and yes, it probably set me back in my career a bit, but looking back, I wouldn’t trade that for anything.

You can travel at any time in your life, but later down the road when you have a mortgage, kids, a spouse, and an adult career, the excuses not to get more legitimate. So scratch the itch now while you’re free, and you won’t regret it later.

25. It’s totally okay if you don’t know what you’re doing with your life

Here’s a hot take: I think you should throw out the idea of seeking a purpose.

Not only is it vague, but it creates so much pressure where you’ll cut yourself off from otherwise good opportunities that could lead you to something purposeful.

What do you do instead? Just pursue curiosity. What are you excited about? Let’s try that. And what you’ll find is that your purpose will find you.

26. Your biggest problems in life cannot be solved, they can only be outgrown

Some challenges don’t have simple solutions. Often, the answer isn’t to fix the problem directly, but to grow beyond it. When you evolve into a bigger version of yourself, problems that once seemed insurmountable become stepping stones in your journey.

27. Don’t believe everything you think

You need to hear this:

Because you have negative thoughts does not mean you’re a negative person.

Because you got rejected does not mean you’re a reject.

And because you failed does not make you a failure.

Start learning to distinguish between facts and stories you tell yourself.

So don’t believe everything you think. Most of the time, it’s not even true.

28. Credit cards are more than just IOUs

I know firsthand the weight of financial stress that credit can put on you, and I’ve seen people close to me in their 30s still affected by the decisions on credit they made in their 20s. The best advice for credit is: never carry a balance and always pay off your cards. I also live by the rule: If you can’t afford five, you can’t afford one.

Even when I was making 2M/ year I was still renting, AND my rent was barely over 2k/mo. Why didn’t I upgrade? Because I had the thing most people never feel: enough.

29. Hard choices, easy life. Easy choices, hard life.

Things that are good for you in the long term often feel hard in the short term. Take exercising – the days you don’t want to do it or you’re too tired, yet you never regret the days where you push through and do it.

Things that are bad for you in the long term feel kind of cool in the short term – like binge eating, procrastinating, and putting off responsibilities. But building a life you love long-term takes discipline, and discipline is sacrificing what you want now for what you want most.

30. How you make your money is more important than how much money you make

You can have the highest-paying job in the world, but if you lose your soul or your family in the process, is it worth it? Money is important, but it’s only one currency. There’s psychological freedom, time freedom, and emotional freedom.

When you factor in all of those instead of just one and base your decision holistically, you’ll realize that how you make your money is a hell of a lot more important than how much money you make.

Couldn’t stop at 30. Here are 3 bonus ones…

31. Anxiety is living in the future, depression is living in the past

The only place you’ll find relief is when you bring yourself back to this present moment. Learning to be present through meditation, mindfulness, or simply engaging fully in what you’re doing right now, is one of the best skills you can develop for your mental health.

32. Holding onto resentment is like drinking poison and expecting the other person to die.

Yeah, it’d be great if we got closure and they’d apologize, but understand that you don’t have to have an apology for you to let go of things. I wish I would have forgiven quicker and let go sooner. There’s such a lightness when you don’t carry around things from your past.

33. Advice is just opinions. Yes, even this advice!

I have seen people waste years of their life following advice they got online from gurus. Only in looking back years later did they realize, that probably wasn’t the best hill to die on, or base their big life decisions on it.

So next time you hear something being discussed on a podcast with great audio and convincing opinions, know that it’s just that: opinions!

The best skill you can learn in your 20s?

Your ability to think for yourself.

What’s one lesson here that hit home for you? Reply to this email and let me know – I read every response.

See you next Saturday!

stop settling, start living

Weekly Strategies to Unlock the 2.0 You

Drop your email to join my newsletter and I’ll shoot you “The 11 Questions to Change Your Life” as a bonus (it’s free btw) 🙌

Clark Kegley