What I Wish I Knew at 22


The kid in that picture was ferocious, principled, and clueless. He rarely took advice and insisted on forging his own way. But here is what I would tell him if he just paused and listened for a minute.

1. Your large life decisions will be surprisingly easy.

At 22, my common worry was: is it the right girl? Is it the right job? Don’t fret over any yes/no decision that unfurls over a large time segment. Walking across the aisle with your bride, the next new job opportunity, those binary decisions will be made clear in gentle nudges to the summit of certainty. The truly hard decisions are flashpoint ones made with limited data, analysis, and unknown ramifications.

2. Acting bigger than you are is a garbage philosophy.

You will practice “fake it till you make it” for years and think nobody catches on. As a nascent technical writing firm, don’t position your team as the second coming of Hemingway and Steinbeck. How about just saying, “Hey, we are two guys with some ability to craft the English word. We are hungry for experience and will burst our hearts to get the job done.” Here’s the deal: nobody values a 22 year old for experience. Few value a 30 year old for experience. You are valued for your brain, your willingness to work hard, to be unruffled by trivialities, and to be pliable.

3. Build things that don’t scale. 

This is a common refrain for startup product development and wholeheartedly applies to career pursuits. At 22, I believed the jump to entrepreneurship would be a 1,000 feet leap. A certain lever is pressed and a magical product appears to the sound of a thousand investors applauding. It doesn’t work like that. You work hard and nothing happens. And work harder, and maybe a few doors creak open when the wind is blowing in the right direction. An outsized leap from average to tremendous is a media embellishment. Greatness is earned and lost every single day.

4. Be selectively competitive. 

When I was 22, I wanted to win at everything. Ping-pong, dancing, golf, horseback riding, Skeeball…it didn’t matter. Lay low and take a breather son. Pick your spots. The old guy at the gym repeatedly striping 17 footers is infinitely more valuable than the Walmart knockoff of Russell Westbrook careening from place to place. Efficient and highly targeted expulsion of energy works wonders.

man playing pingpong
Really…it might be ok if you lose.

5. Chunking all your spare cash in a 401K is highly overrated.

Sure, save some money for retirement, but don’t expect a faceless board of directors to risk mitigate your life. Taking all of your hard-earned funds and pitching it into a market that unapologetically is measured by greed and fear is betting an Ace hits on the river. On second thought…

6. Set up a DBA, dump some cash into an account.

Go down to the courthouse, pay $25, and head to your bank to open a business account. Redirect some of that retirement cash to your DBA and spend it unapologetically on your side hustle. It doesn’t matter what you do: create websites, build fences, DJ, or write policies and procedures. This is your hustle account for you to get smarter, wiser, and eventually, to mitigate life risk.

7. Live here now.

Being 22 was a juxtaposition between the carefree days of youth and the hope of accomplishments yet to come. At times, my focus meandered excessively into daydreams or nostalgia. The past is a compelling teacher and the future’s possibilities are alluring, but life is only lived in the present. Arrest those meandering thoughts. Be here now – no matter where you are.

8. Leading people is fraught with uncertainty, circumstance, and nuances. And the moment you think you are good at it-that’s the moment you have failed. 

At 22, I had this one figured out because I was cool with everyone. I had friends across the spectrum, and being a boss was basically being a cool friend who helped them out, right? No, not in the slightest. Anytime I felt a skin of certainty crawl over my perceptions or abilities of people, a humbling experience was soon to follow. 

Ego is the enemy of what you want and of what you have… Of working well with others. Of building loyalty and support.” 

Ryan Holiday

Be humble. Listen. Listen some more.

woman walking alone in the snow road

9. Be source apathetic. 

Be gracious, but don’t bow to titles and organizationally imposed authority. A good idea is a good idea whether it is presented by a CEO in a boardroom or a homeless person screaming hacksawed sentences in the middle of a vacant lot. I met that person eight years ago and my crew shied away from her yelling. I diverted straight to her and said, “What is it that you are supposed to tell me?” She said, “Remember the Alamo!” I still carry that sentiment with me because…

10. You are going to die. 

I know it doesn’t feel that way at 22, but death is coming for you. Hold that gently in your mind every day and without fear. Death is not a burden, but simply a design feature of the human experience. From dust you have come and to dust you shall return. Work a job you love, design a life you want, and tweak as required. Hug your friends and family and tell them you love them. Even if it makes them or you uncomfortable.