25 Lessons I Wish I Learned Earlier

Growth, Fear, Death, etc.

I turned 25 years old yesterday. 🎂 (I’m still alive—go me!)

So here are 25 quick lessons that I wish I had learned earlier:

(If you’d prefer to watch the video instead)


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1. We live many lives, we die many deaths. 🪦

We go through lots of stages in life from childhood, going to school, college, entering the workforce, and old age. And recently, it’s been helpful for me to think about these stages as separate, individual lives.

I am not the same person that I was when I was 18. The childlike wonder, lack of true responsibility, and seemingly endless possibilities of what my life would look like at 24 are gone — and it genuinely feels like that part of myself is dead.

We learn, grow, and fundamentally change throughout these stages of life and that’s okay. But it also lets you see how important it is to really take advantage of every stage of life.

I missed having a traditional college experience. (Here’s the video I made about why I dropped out) And while I think this was still the right choice for me, I can’t go back to being 18 and leaving home for the first time to make friends, party, and “discover myself”. But part of me wishes that I would’ve done these things when this stage of my life was still active.

This also works with time going in the opposite direction. I’m probably not going to be able to climb mountains, land kickflips, and go out partying until 2 in the morning when I’m 65 years old. You’ve got to accept and take advantage of the stage of life that you’re in.

2. Growth Mindset 🌱

This idea is so simple but it has changed my life.

Having a growth mindset is simply believing your talents or skills can be developed through hard work, good strategies, and input from others.

People with this mindset tend to achieve more than those with a fixed mindset — those who believe their and others' talents are innate gifts.

Imagine a person seeing a professional musician and thinking:

“They must’ve been born to make music, I could never do that”

versus a person who thinks:

“This person learned a skill like anyone else and, theoretically, I could too if I put in the amount of time and effort they did”.

It’s a simple difference but the second person is going to get much further in life. I wrote an entire article about mindsets if you want to learn more. This mindset pairs perfectly with the next thing I wish I’d learned earlier.

3. Internal Locus of Control 🎮

Locus of control is the degree to which people believe that they, as opposed to external forces, have control over the outcome of events in their lives.

People with a strong internal locus of control believe events in their life are primarily a result of their own actions. When receiving exam results, people with an internal locus of control tend to praise or blame themselves and their abilities. Opposed to those with an external locus of control, who tend to praise or blame external factors such as the teacher or the test.

Having an internal locus of control means that you take accountability for the fact that you alone are in control of your life and your destiny.

When combined with a growth mindset, it allows you to accept your situation while knowing that you have the power to change it.

4. You will never arrive 🌀

Everyone is working towards something. A goal they want to achieve, a job they want to get, a person they want to date.

In the moment, it can seem like getting that thing is all that matters and that you won’t be happy or fulfilled until you get it.

This, unfortunately, is never true.

You will never arrive at a perfectly happy, fulfilled, and totally satisfied state from trying to achieve your goals.

Everything is fleeting — accomplishments, items, and people.

When you accept that you’ll never arrive, it’s much easier to enjoy the journey and allow yourself to be happy in the moment.

And after 24 years of trying to figure out what life is all about — it seems like enjoying this bizarre, beautiful journey is kinda the whole point.

5. Question your emotions

I’ve felt a lot of very strong emotions in the 25 years that I’ve been alive.

And I think the most powerful way to understand yourself as a person is to dig deep into why you feel something.

Love, anger, fear, jealousy, judgment — all mean something.

Next time you get hit with a strong emotion, especially a negative emotion, really examine it and try to understand where this feeling is coming from. What did you learn or what happened in your life that is causing you to feel that?

I’ve had to unlearn a lot of judgment and self-consciousness that I never would’ve realized I had without really diving deep into where my emotions are coming from.

Every emotion has a source. If you can find those sources, you’ll understand yourself better than 99% of people.

6. Therapy will give you superpowers 🧘

Understand your mind or become a slave to it.

Going to therapy was one of the best decisions I have ever made and it taught me the most important skill there is — understanding how my mind works.

Your mind controls everything you do, every thought you think, and every emotion you feel. If you can learn about how your mind works you can work with it instead of constantly fighting against it.

Fighting your mind only in anxiety, depression, and addiction. Go to therapy and learn to work with it. It’s likely the best thing I’ve done in my life to benefit my overall health and I recommend it to everyone.

7. The Spotlight Effect 🔦

The spotlight effect is the psychological phenomenon where people tend to believe they are being judged or noticed more than they really are.

We’re all constantly in the center of our own world so we almost always overestimate the amount of attention people are giving us.

People give up or straight up don’t even try to learn new things or have new experiences because they’re afraid of what other people might think. But the truth is that nobody actually cares what you’re doing. Everyone is the main character of their own story and they are definitely not thinking about you.

This was really challenging for me when I started my YouTube channel because I was genuinely worried about what other people would think — that my family, friends, and strangers would be making fun of me for trying something new — but then I got like 10 views on my first video and realized that nobody actually cared and that this fear was all in my head.

This actually goes really well with the next lesson I learned…

8. Embrace the Cringe 🫂

The curse of being a beginner — Learning something new is ALWAYS awkward. You’re likely not going to be good at it, know what you’re doing, or feel like you belong.

But your biggest critic and the only person who can truly stop you from growing and learning new things… is you.

If you can learn to silence your inner critic and allow yourself to be a beginner, learn, and fail without self-judgment, you will grow so much faster than anyone who is self-conscious about trying something new and looking weird or failing.

Trying and failing is the most effective way to learn — Be okay with being a beginner, be okay with failing.

9. You attract the energy you put into the world

The people you meet and the experiences you have are directly correlated with the energy and attitude that you put out into the world.

If you want to attract positive and energetic people then you need to literally give those vibes out to the universe.

The more loving you are, the more love you’ll have in your life.

And on the flip side, the more of an asshole you are, the worse your life and the people in your life are probably going to be.

10. When looking for love, don’t wear a mask 👺

Pretending to be someone you’re not will only attract people who like the person you’re pretending to be.

If you want to make real connections with people who can see and love the REAL you, you need to be that person and refuse to hide it.

I used to have a real problem trying to portray myself as cool, serious, and distant because, for some reason, that’s what I thought would attract people. But anyone I met while wearing this mask of a personality — I just couldn’t truly connect with. They didn’t know or like the real me.

After realizing this and actively trying to be my true self regardless of judgment or acceptance — I found the love of my life not long after.

Everyone deserves to be with someone who loves them for who they are but you’ll never find that person if you never show the world who you really are. And sometimes it really does take courage to do that.

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11. Fear is your friend 😱

Fear is the best teacher I’ve ever had.

In a world where many of us are safe from evolutionary threats and don’t constantly fight for our survival, fear is not designed to keep us safe.

It’s designed to show you what you think your limits are.

If you’re afraid of something that has no real life-threatening consequences, this is just fear telling you that this is somewhere you need to grow as a person.

There’s nothing inherently dangerous about public speaking but so many people are absolutely terrified of it — I call these “unreasonable fears” because failure has basically no pain involved. If you can find and overcome these “unreasonable fears”, your skills and confidence will grow faster than you thought possible. And you’ll start actively seeking out these fears just to destroy them.

In your own life, try to find something you’re afraid of that doesn’t have serious repercussions if you fail, and do it. You can thank me later.

12. Don’t forget about the side quests 🛡️

It’s easy to get caught up chasing your goals and zeroing in on your career, your finances, and your journey to self-realization — but remember that there are so many amazing people, places, and activities out there.

Recently I got a commercial drone pilot's license for pretty much no reason.

I had to take an online course, and learn a bunch of stuff about airspace, weather patterns, and regulations. Absolutely nothing I learned will help me advance in my career or achieve my goals — BUT IT WAS FUN AS HELL.

I did this to remind myself of the endless options of what we can do and be in this life. It’s the same reason why I randomly went to LA to take a surf lesson earlier this year. Neither of these things will help me with my career as a data analyst or make me any more successful in life but they were unique experiences that have genuinely enriched my life.

Variety is the spice of life and these little side missions can really make it feel more fulfilling.

13. Baseline Theory 📈

Baseline Theory is a term I created to describe the work you need to do on yourself before you can really start enjoying everything that life has to offer. Your life stats need to be at a baseline before you can really take off.

It’s hard to take advantage of life if you are physically or mentally unwell. Or if you’re deeply in debt.

Mental, physical, financial, social, and spiritual health need to be taken care of. Once you’ve gotten all your stats to a healthy baseline, life starts to open up for you and you can start to “play the game”.

14. Evolutionary skills 🧗

Evolutionary skills are things that our species learned how to do in order to evolve and survive.

Running, climbing, swimming, and fighting are all examples of evolutionary skills. And while in modern life most of these skills are pretty much obsolete in terms of survival, the better you get at these skills the more innate confidence you have when interacting with the physical world.

The more of these skills you learn, the more your mind is able to trust your body to overcome any challenge the physical world throws your way.

15. Meditate on your death every day 💀

“Let us prepare our minds as if we’d come to the very end of life. Let us postpone nothing. Let us balance life’s books each day. … The one who puts the finishing touches on their life each day is never short of time.” — Seneca

Memento Mori is a phrase that I talk about a lot. It’s Latin for:

“Remember that you have to die”

It is a reminder that we won’t be around forever so we need to live with urgency and live as if we could be gone at any moment.

Remember that you and everyone you love are mortal — so take advantage of the time you have, do good, and tell the people close to you that you love them.

As my girlfriend would say, “Memento mori” is a more productive yolo.


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16. Humans aren’t meant to be alone 😔

In the periods of my life where I’ve been the most depressed, I’ve also been the most alone. There is a direct correlation between isolation and sadness. I’m a very introverted person and even though I really love spending time by myself, it’s not even healthy for me to be alone for extended periods of time.

The pandemic lockdowns taught us this firsthand. Don’t doubt the value of community — even if you’re a self-proclaimed “lone wolf” like I was. People are stronger together.

17. Storytelling is one of the most valuable skills you can learn 📖

We have adapted as a species for millions of years to absorb information through stories. We are captivated and compelled by them much more than any other way to convey information.

If you can learn to tell good stories you’ll become a more interesting person, you’ll be able to better communicate and convince people of your ideas, and you’ll be able to find more meaning in your life and in everything you do.

18. Get off the Hedonic Treadmill 🏃

The hedonic treadmill is a metaphor for the human tendency to pursue one pleasure after another.

It’s super easy to get caught up in wanting the next best thing. A new car, a fancier apartment, a better phone or computer — I say while writing this on my new Macbook Air…

This happens because the surge of happiness that’s felt after a positive event, like sitting in that new car for the first time, is likely to return to a steady personal baseline over time — so back to how you felt before buying the car.

Perusing more pleasures will only make you happy for a moment and then you’ll feel normal again. This is why there are still depressed millionaires — because no pleasure will ever “be enough”.

If you can realize this and get off the endless treadmill of hedonism and wanting the next best thing — you’ll be happier than most people.

Hint: Gratitude is the answer.

19. Creating is better than consuming 🎥

One thing I wish I learned earlier is how much better creating is than consuming. Consumption, of food, content, or other stuff feels good at the moment but overindulging can leave you feeling empty.

Creation is much more difficult but so much more rewarding. And unlike consumption, the joy you get from creating things lasts much longer than consuming them.

The happiness and confidence you get from learning to cook a new recipe typically last longer than the happiness from eating the food. This is especially true on the internet. You can waste hours at a time watching YouTube videos but no video that I’ve ever watched has come close to making me as happy as when I finish an edit and get to upload my own.

20. Books aren’t sacred 📚

I was scared of books for a long time. Once I started reading a new one I felt like I was obligated to finish it or that there was some intellectual high ground to reading a book cover to cover — especially with nonfiction.

Learning to treat books more like articles was the best thing I’ve ever done for actually extracting information and learning from books. It’s okay to skip stuff, it’s okay to skim and read the parts that are interesting to you, and it’s even okay to read half and never finish the rest.

I just skipped the first few chapters of “Building A Second Brain” because I already know the author’s backstory and the premise of the book. I want info on tools to do personal knowledge management so that’s what I’m going to read and I’ll skip the rest.

Treat books more like articles and you’ll end up reading way more plus you won’t waste time reading things that aren’t relevant. (You don’t get a special prize for reading the entire book.)

21. Grit wins every time 💪

Luck, talent, and circumstance are often the main things attributed to success, but one trait outweighs them all — grit.

“Grit is about having what some researchers call an “ultimate concern”–a goal you care about so much that it organizes and gives meaning to almost everything you do. And grit is holding steadfast to that goal. Even when you fall down. Even when you screw up. Even when progress toward that goal is halting or slow.” — Angela Duckworth

Successful people just keep trying. Over and over again regardless of failure or discouragement. If you can set a goal and show up every single day with an unwavering belief that you will one day achieve it — You will win at everything you do.

22. Travel alone at least once 🌎

Solo traveling is one of the most rewarding experiences you can have. Being in a completely new place, alone and left to your own devices will force you to grow no matter what.

Along with the absolute freedom to explore a new place exactly how you want to, traveling alone will put you out of your comfort zone and force you to interact with local people, try new things, and open your eyes to a way of living that is likely very different than what you’re used to.

You’re also free to be whoever you want to be and in a place where nobody knows who you are. This locational anonymity is great for growing and learning more about yourself.

23. Show your work 📝

Learning something new is fantastic but I firmly believe that it is always better to learn in public.

Even if you’re an absolute beginner, share what you’re learning and what you’re working on — online.

I’ve been learning how to make videos for around a year now — teaching myself how to use a camera, how to write scripts, how to edit — and if I waited until I learned all of these skills to upload my first video…

I would have 0 videos uploaded instead of 40.

Sharing your journey is way more powerful than sharing your final result. Try, fail, learn, and grow in public and you’re skills and success will increase so much faster.


I use the phrase “KEEP SEARCHING” in my writing and videos a lot. And this is kind of the philosophy that I live by.

In the search to find out who we are and what we love to do is where I feel most alive. When you’re engaging in an activity that makes everything around you fade away leaving you perfectly in flow is what I live for.

In psychology, a flow state, also known as “being in the zone”, is the mental state in which a person performing some activity is fully immersed in a feeling of energized focus, full involvement, and enjoyment in the process of the activity. I use this phrase in my videos because this is the feeling I get from making them — the search, the process is paradise.

It’s never been about arrival or completion, it’s always been about the search.

KEEP SEARCHING is a reminder to me to stay in this state. Not looking for an ending or to complete a goal but to become fully present in what I’m doing because that’s where the best parts of life are.

25. You Don’t Need Clarity 🗺️

My final piece of advice is to myself.

I spend a lot of time stressing out about the perfect path I can take to achieve my goals instead of trusting my gut, diving into the murky waters, and doing the fucking work.

It’s easy to fall into the trap of overthinking, waiting for that moment of perfect clarity before taking action. But I’ve learned that most answers come through action, not prior to it. Searching for clarity has become an excuse (and an insidious form of procrastination) that has stopped me from moving forward.

And my hope is that this year, that ends.


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Thanks so much for reading another issue of The Jailbreak!

Til next time, Nomads. ✌️

- Jack Ross

Jack Ross (Data Engineer, Writer, Nomad)

Chat with me directly by replying to this email, follow me on Twitter for regular updates, and subscribe to my YouTube channel for travel vlogs, tips, and insights on unlocking freedom in the digital age. ❤️

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  • Increase strength 🏋️

  • Improve recovery ❤️‍🩹

  • Boost cognition 🧠

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