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Success: My Open Letter to 22 Year Olds


Hi Friend,

Thanks for stopping by. I’m writing you the letter that I didn’t get 20 years ago. Thankfully I did enjoy the benefit of some amazing mentors along the way, along with some great books, that helped me find my way. I’m a success today because of them. And I’d love for you to look back on two decades as equally satisfied.

You’re tired of hearing about how young you are, so I won’t start there. Instead, I want you to look back on the two decades you’ve lived already. I want you to notice three themes that you already know to be true.

Your Path to Success

1: Success on the playground was a matter of chance…and teams

If you think back to your earliest kickball, and dodgeball days, you’re likely to admit that the days you won were less about you and more about the teams you found yourself on. And more than likely, that was chance. Sure, maybe you got to be team captain a few times. But the rest of the time, it was chance.

Success going forward will also be a matter of chance. Keep your eyes open. People who tell you that you can plan everything are lying (to themselves, and then to you). But you will improve your chances if you hang out with remarkable people. So join smart teams where you can learn. Be the dumbest in the room as often as possible.

2: There was homework every day…but it didn’t have to take up your day

Yes, life has been filled with homework. Every. Single. Day. But – if you were smart and a tiny bit crafty – you could get it done during class as the teacher repeated things for the third or fourth time. And if you did that, your afternoons were yours.

Success going forward will take work. Hard work. But it doesn’t have to take over your life. Spending an afternoon hanging out with a few friends (or making friends) may have a greater impact on your future success than sitting at the computer for another hour. Get out. See the sun. Spend time with friends and family. You can’t predict the relationship that will bring success.

3: We tell stories. We listen to stories. Craft our life’s narrative.

Whether you enjoy streaming movies from Netflix or Hulu, or you go to the actual movies – you and I both know great stories are amazing things. If you look back on your life, you can easily remember some of your favorite stories – whether it was a great book or a movie rendition of the book (come  on, you know you did it too).

I want to encourage you to think twenty years out. I know, it’s a crazy exercise. It’s virtually impossible to know what things would look like. But do it for a second. Now imagine that you’re sitting in an office being interviewed for a position. The person in front of you asks you to explain your work history in a few minutes.

At that moment, I want you to think about your answer in the form of a story.

To help you, I want you to think about your story in this shape – we meet you, we see a problem, we see how you’ve been battling that problem over xx years, we learn the result.

When you think about things that way, you think about the big problems, not the little ones. You think about the mission, not the tasks. You think about the cause, not the role.

The result of this approach is powerful.

If you do that work now, twenty years from now, answering will be easy. But way more importantly, it will help you make decisions today. The decisions you make over the next twenty years can either be part of a single, cohesive narrative, or they can be an aimless scattershot of random events that happened to you. The only one who decides is you.

I read a book in my 20’s. It said that Microsoft had a horrible time filling one particular role – what they called a program manager. It was halfway between the product marketing folks and the development folks. I’ve spent the last twenty years living in that tension, being a connector – connecting marketing and development teams. The results have been fun. I’ve helped run several startups, launched tons of online software solutions, and become someone who helps others with their new product development.

That’s my story.

Ready to Write Your Story?

But more importantly than me telling you my narrative is the fact that these few sentences help me regularly determine several things, like:

  1. Where I work

  2. Who I work with

  3. When I’m willing to work for free

  4. Who I want to meet

  5. Who I don’t waste time with

If I told you that six sentences could do all that, wouldn’t you want to sit down and do some writing?

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