A Letter to My 22 Year Old Self on Entrepreneurship

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.