A Letter to My 22 Year Old Self on Entrepreneurship

[I was inspired to share this after I saw @lurens post asking for advice—I wrote this post 6 years ago, hence the reference to being "32" below. I still hold these things to be true as I get closer to 38 now. Enjoy!]

In a few months from now I’ll be 32 and at that point I’ll feel well on my way to the big Four-Oh. At this point in time I feel like I have had the amazing blessing of experiencing so much and yet, at the very same time, I feel ill-equipped for most everything.

It’s as if the first 30 years have been generally inadequate at preparing me for the next 30. I think I could argue pretty substantially about why but I’ll save that for another post.

But as I look back on the last decade I can see a few things that I have picked up specifically as it relates to entrepreneurship and startups. In many ways there is very little preparation that anyone can do to prepare oneself for such a lifestyle (although I’ve attempted to jot a few things down here) and I’m going to try again to provide some helpful thoughts to a younger version of myself.

So here are 7 things that I wish my 22-year old self had known (and perhaps you can glean a thing or two here for yourself):

1. It’s a Muscle

I’ve shared this so many times in real-life that it’s hard to imagine that I haven’t shared it explicitly on the blog but the reality is this: Entrepreneurship isn’t a skill, a talent, or something that you’re necessarily born with. It’s a muscle, something that must be used, constantly.

It’s like many things in life where you must work at it, grow it, refine your approach to entrepreneurship and you must be committed and dedicated to the continual growth of that muscle.

Practice liberally, practice often. I wish I could have started even sooner although at the time I really had very little idea about entrepreneurship proper. But, I wish I could have started practicing it explicitly when I was 22.

John, you were given some pretty shitty advice when you first left college – I’m sorry that you listened to it but you could have been much more intentional. And, if I’m bold enough, you would be so much farther in your career than where I am today (as a near-32 year old) if you had started sooner.

That guidance counselor fucked you over but it’s your fault to not have invested in that muscle sooner. It’s okay, don’t feel too bad about it.


2. It’s Dangerous to Go Alone

Entrepreneurship is more about working with great people and less about the problem that you’re trying to solve, even though the problem that you might be trying to solve could be world-changing.

Dear naive and egotistical 22-year old John… you are not that smart, not that great, not that technically-gifted to do this by yourself. Learn to work well with others, to compromise, to negotiate the complexities of human relationships just as much as you were investing in your own ideas.

Learn to partner, find great people, spend less time alone and more time with others that are much, much smarter than you. I know you think you’re a badass but you’re not. You are simply not that great, nor special, nor talented. You need help, so get some.

3. Mentorship

In light of the previous point, you need to go find a mentor – and sooner the better. You will eventually do this but much later in your 20’s and you’ll end up regretting not starting sooner.

These people are not only available but interested in investing in you. They want to help and they don’t have any ulterior motives. They just want you to succeed and do not necessarily need anything specific in return. Be willing to trust these people more and to seek their counsel often.

And if you have some time (make it regular), go talk to your dad every other week. He’s a genius, trust me on this. He knows more about running a company and being an entrepreneur than you know or believe.

4. Money

John, you will make a number of catastrophic blunders over the next 10 years that will be primarily motivated by your wallet. Please, please, please do not choose the options that will make you more wealthy. The reality is that you won’t come out as well as you think you will and it’ll cause you more heartache than you could possibly imagine.

You family, your friends, your children, and your relationship with your wife will be tested to the very brink. You will discuss divorce multiple times because of some of these decisions and it will be your own fucking fault. Yours. Just you.

Instead, choose the options that will grow you professionally, that’ll test the really important things in who you want to be as a professional, grownup, and leader. Choose the path less traveled and cast off the American Dream of wealth and prosperity. It’s mythological – you just don’t know that yet. It will never be worth it.

10 years from now, today, you have finally woken up to this reality and you may even regret. You never want to regret.

5. Friendship

You don’t have many friends and you won’t have that many friends 10 years later. That’s okay and there’s nothing wrong with that. You’re going to learn some very important things about yourself, like this here, which will dramatically change your life and give reason for many of your struggles as a person and as a professional.

But entrepreneurs need friends, people who aren’t aligned with your business and who don’t care what you do to earn a living. You will want, even more so 10 years later, people that just love you for who you are and not what they can get from you (or what you can give them).

Start today – learn what it means to be a real friend. I know it’s tough and I know you’re more interested in your work; that won’t change much, but you can start learning much sooner that friendship matters.

This also means that being a friend to your direct family and your brother, especially, will be vitally important. It will be tested, it will be tried. You will fail, but it will save your life.

6. Your Health

Your health is paramount. Right now I’m in the best shape of my entire life but it wasn’t always this way. For instance, you take your own health for granted and treat your body like a wasteland. You feed it anything you want and do not get nearly enough sleep. Your exercise is spotty and you simply don’t give a shit.

Can I clue you in? You’re going to pay for that. Your body is going to collapse and you will find yourself in the hospital. You will have to shutter a startup and you will lose a ton of time as you recuperate. It will be a lengthy recovery, by the way, and you will hate yourself for a long time.

It’s because you didn’t care and because you didn’t listen to your body and it’s because you didn’t listen to your wife. You had a “ton” of reasons not to care but they were paper thin. You know that, though, but you’re just lying to yourself. Please, get your health in order.

Entrepreneurship is about self-mastery, mortification, and leadership. You’ll thank me for the results and your teams and those that you lead will trust you more because of your investment.

7. Your Faith

Over the next decade you will be tested emotionally, physically, mentally, and spiritually. You’ll find that your personal faith will change so dramatically that it might be generally unrecognizable to the faith that you have today.

Yes, you will finish two Masters degrees (oh, didn’t know that was on the agenda? Hah. You’re fucked! … In a good way.) and you will come out knowing less about the spiritual life than when you started but you won’t regret it.

What you will regret is some of the seasons of investment (or lack thereof) where you decided to spend more time building software than investing in this part of your own life (and your family’s).

All I can say is that you haven’t given up and thank God for that. But you will encounter some really tough stuff that’ll beg life-sized questions on whether or not it’s even worth the effort. Please don’t quit. Please fight hard. Don’t stop asking the big questions.

And it’s okay to doubt. This is a very necessary and healthy thing. You’ll be a doubter for the rest of your life I imagine.

Good luck John. You’re going to need it. You’ll make it. And you’re going to have a hell of a time.

John, your bud and almost-32-year-old.

  1. 12

    Totally agree with everything here.

    I can, unfortunately, add another perspective. On July 26th, 2016 I was hit while cycling home from work. I had a Glasgow Coma Scale (GCS) of 1 (7 is fully conscious, 0 is dead) and I was not breathing. By pure luck I was hit 1-block from a hospital AND during shift change so the first people on scene were an ER nurse and a neurology nurse. They got me breathing again and into the ER quickly.

    Prior to my crash I had been willing to put in long, hard hours at work with the goal of being a CTO/CIO/CISO of an insurance company. That crash made me realize that those long hours are not worth it. It's not worth the negative impact on my own life or my friends and family. It's a cliché but on the hospital bed I wasn't thinking I wish I had spent more time at work, I was grateful for the amazing friends and community I've built who came to visit me and have supported me post-crash.

    1. 4

      Wow powerful stuff, and powerful take away. I feel like we hear this same advice over and over and over again (nobody wishes they had worked more when on their death bed), and yet for some reason it seems so fresh and eye-popping every time.

      I hope your recovery went (or is still going) well.

      1. 3

        Thanks, it took 2.5 years before the medical/legal team finally said "oh, maybe this is chronic pain so maybe we need to teach/support you in dealing with chronic pain for the rest of your life".

        Part of what motivated me to create https://trauma.chat was the idea of crowd-sourcing recovery info. I would have loved to been somewhat prepared for chronic pain 2+ years ago, which would have allowed me time to accept the changes in life going forward..

        1. 2

          Tagging @c0nsilience as I think he might find this thread interesting.

          And on my own note: <3

          1. 2

            Thanks @heylorenzut

            This is definitely my cup of tea.

            @8bit very succinct and to the point! Thanks for sharing with all of us!

            1. 1

              thanks for reading it!! anything i can do for you?

              1. 2

                Not that I can think of. I just appreciate the insight. 👍

                1. 1

                  cool! you know where to find me!

          2. 1

            appreciate you being here @heylorenzut! :)

    2. 4

      omg friend! what?!


      (i made that for you.)

      i'm so glad you're here and made it! we're like the same age too!

      1. 3

        Thanks. Even 3.5 years post-crash it was hard to write that 1 paragraph (and has now caused a headache so I guess I need to drink water and put the computer down).

        1. 1

          i had a major migraine today and had to lie down on my rug, literally where i was standing. ugh. fuck me.

          1. 1

            Really sorry to hear! Do you find they increase with stress? We're in quite a bit of stress these days. If it helps, I've created something to track my own symptoms.

            1. 1

              i think it really is. this covid19 thing is really messing me up.

    3. 2

      this hit me. Hope you're well now. :D

  2. 3

    Really appreciate the perspective John! I don't dream of riches, I dream of a quiet life with a wife and kids that I love, reasonable or beyond reasonable work hours, and financial independence.

    1. 1

      i dig that so hard. yes. thank you for commenting!

  3. 3

    Waow. That's just... amazing.

    "Entrepreneurship isn’t a skill, a talent, or something that you’re necessarily born with. It’s a muscle, something that must be used, constantly." ; I couldn't agree more. Entrepreneurship is a Game.

    You can read all the books you want, be prepared for everything, you will never know what to do until practicing. That's why it's important to practice, and learn from others. Entrepreneurship is very hard, and a lonely journey.

    This is why you need to make Friends. Friends that are sharing the same passion than yours. You will help each other, without expecting anything in return. That's really what Entrepreneurship is.

    1. 2

      100% — building community isn't just good for business... it's just good for life! i mean, and my mental health and everything.

      omg. yes.

  4. 3

    You really made my day, thanks so much! I'm currently 22 and this post helped me a lot!

    Since the last half year I'm trying to sort out my situation:
    -Got double bachelor Math&CS
    -Going to top tier University for CS Master since 6 months
    -Doing somewhat stable business with 2 other friends since I'm 18 and making around 500k$/year & seems like there is even more upside (unfortunately currently in Trap like #2., doing too much & not relying enough on other people, also feels like a bit like #4.)
    -Definitively trying to get a mentor now (#3.)

    Kinda got burned out since I started master since I have near 0 freetime left(#6.!). Thinking of either quitting university or businness, It feels like I can only do one, but I cannot choose one of it.

    Since I feel inspired by your post, can I ask you what your choice would be?

    1. 1

      ooph. wow. i'm so thankful for the question!

      (and gosh, you're username is...)...:



      anyways, in terms of your question... it's ultimately up to you.

      but, here's one thing that i've realized in my own life that hasn't steered me wrong:

      choose relationships over opportunity.

      just like i said in my post, our relationships drive a great deal of satisfaction (and misery) in how we conduct and experience life. choose the pathway that optimizes for the relationships that mean the most to you.

      if that means hanging with your friends for a bit longer, then, great. if that means that there are some other folks that you'd like to work with or feel compelled to "sit under" (be coached and mentored and lead-by) then go do that.

      for instance, i was a late-addition cofounder in my last startup and i said "yes" because i simply wanted to sit under the leadership of a long-time mentor. i couldn't believe that i had an opportunity to learn from him full-time... i mean, that felt like a dream!

      i was compensated fairly but the biggest wins were my chance to watch him, up-close and personal, as he built a company from nothing into a venture-backed company (raised $3M seed, $13.5M series A) that's currently doing > $3M in ARR.

      everything that i'm apply now, as a leader in my own startup, i owe in great deal to him.

      i followed the relationship.

  5. 3

    Sooo good @8bit. I resonated with so many parts of that, but felt a specific pit in my stomach when reading:

    Learn to partner, find great people, spend less time alone and more time with others that are much, much smarter than you. I know you think you’re a badass but you’re not. You are simply not that great, nor special, nor talented. You need help, so get some.

    I'm sure that pit means something.

    1. 1

      i've continually been driven by this! and, it's lead me in a very clear and much more consistent path.

      betting on relationships has been the ultimate win in my life.

  6. 2

    Keep writing, keep sharing. You're helping many.

    1. 1

      thanks friend! i'm very much enjoying this community!

  7. 2

    John, it's time to write a letter to you +10 years old self! :) You'll learn from it in both times, now and then.

    I still regret I didn't write a letter to my +10/+20/+30 old self in my twenties, when I really wanted to. I had a lot to say.

    1. 1

      this is a really neat idea...! perhaps i will write this!

      1. 2

        Have you ever thought that the aged self will need an advice from you? .)

        I'm convinced most people think they have got enough to teach "that young idiot" from the past, the thing which will never happen.

        1. 1

          i oftentimes think that these types of posts are more for the writer... and not the reader.

          as i processed this post, anew and with fresh eyes, i realized that i've gotten many things right but also a few things slightly wrong.

          that's okay. it's not supposed to be prescriptive or perfect. it's supposed to be perspective-changing.

  8. 2

    Each of these points hit home, given that I'm 25 right now.

    It's making me realize a lot that I'm probably going to regret later down the road...

    Thanks for posting this man.

    1. 1

      you have plenty of time to move things around... getting a mentor or some other folks around you, though, would do a world of good!

  9. 2

    not gonna lie, you had me at 6.

    1. 1

      7 meant nothing? :P

      1. 2

        maybe I'm reaching there... :P

  10. 2

    Thank you very much, John. I'm 19years of age and this post is very useful to me. I just started my entrepreneurship journey. I will send you an email later. I'm also on my way to the big Two-Oh

    1. 1

      thank you! can't wait to hear from you!

  11. 2

    amazing story I'm extremely glad that you've shared this with the community. Im currently 20 years old at a university studying business and this type of conversation is exactly what I love to hear. I did not take this one lightly.

    1. 1

      let me know if there's anything i can do to help you!

      college and university was a very hard time for me... i was never more confused than when i was 18-22 years old...

  12. 2

    I'm really glad that you shared this. This reflection is so important and a lot of the lessons that you mention have been crucial for my growth. Thank you for sharing!

    1. 1

      you're welcome and thanks for checking it out!

  13. 2

    I really appreciate your post. Something I have been struggling with is how long a road it can be to be an entrepreneur. Even these ideas that we have right now - if you took the best one, it may not start to realize huge profits for 5-10 years.

    That's why it's important to be in this game for the long haul. Also, it is important to have an idea that you are interested in so that you don't just jump off the wagon.

    I also like your comment about finding a mentor. I have found someone who I look up to who has been successful in entrepreneurship. I will have to focus on cultivating this relationship further.

    I wanted to ask about your comment about money. To what are you referring if you can provide some more information? I too have had opportunities to make more money and have chosen the paths that I felt will build my career more in the long run. It is hard to see at this time how that is the right choice.

    1. 1

      well, i took some jobs because of the paycheck, pure and simple. i didn't care about the people or really the project. i just wanted as much money as i could get.

      those jobs didn't end very well (they didn't start very well either—🤦🏻‍♂️)!

      in some other examples, i said yes to a job that my wife told me not to take. i took it anyway. that was the first and last time i'd ever make that mistake... but, again, it was because i just wanted to make more money... and it cost me a fuckton of trust between my wife and i that i then had to spend years repairing.

      i should have just said no... because my best friend really believed it was a bad idea. i'm an idiot sometimes!

      1. 1

        Interesting. Thanks for the information. It seems it’s always better to follow your heart in the end and heed the advice of those who care about you!

        1. 1

          your head will alway compete with your heart. that's the way of things.

  14. 2

    This comment was deleted a year ago.

    1. 1

      :) thank you for commenting!

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