7 things I learned in my 1st year of chasing a dream full time.


This week marks one year since Jenny and I launched the biggest career adventure we’ve ever gone on. After 15 years at big companies we decided to strike out on our own. (I say “we” because it was definitely a team adventure with both of us looking out over the same railing of the same boat over the same ocean horizon. Hannah Crosby captured that feeling perfectly in her painting above.)

In reflecting on that, I realized I’ve learned a few things these last 12 months. Here they are:

1. Never blame a boss for holding you back.
For a decade I told myself “Oh the things I could do if I didn’t have a boss!” Last year I became self employed and found myself technically without a boss. Suddenly this overwhelming sense of panic set in that said, “OK, there’s no one to blame except you. You’ve talked a big game all this time, let’s see what you’ve got!” Never blame your boss or job from preventing you from doing cool stuff. Just do cool stuff now. Be honest that most of the time the person holding you back is you. (I’m the greatest hindrance to my own adventures!)

2. You will feel like the only one who doesn’t have everything figured out.
This is a huge myth. There’s a name for people who tell you they have it all figured out, they’re called “Liars.” I don’t have it all figured out. The older I get the more I realize life is like jazz, not classical music. You don’t get perfect sheet music to follow step by step, you get skills that you improvise as everything constantly changes around you.

3. You need people.
Out of pride and fear, I sometimes hide. I hole up, afraid that asking for help indicates that I’m weak or dumb. Shouldn’t I have things figured out by now? Won’t people doubt all my ideas if I tell them I’m scared and need help with a project? If I was talented enough, smart enough and awesome enough wouldn’t I not need people? These are the fears I hear sometimes. The truth is, I can’t do this alone. Andy Traub and Shauna Callaghan for instance helped me get my blogs back up. They were and continue to be amazing. Working on your own is a lonely, isolating business if you’re not careful. I’m learning to ask people for help.

4. Some people won’t understand.
I feel like a confused loser when people at dinner parties ask me what I do. I love saying “I write books!” but their faces often say, “That’s not a real job or that’s not enough of a job.” I feel like I have to justify my existence in those moments and usually just ramble until I have finally worn them down through an onslaught of words and sweatiness.

5. It’s fun!
The highs are high and the lows are low and the middles are sometimes confusing, but it’s fun! Every day is different and the joy you get to experience is worth the fear you have to face. I’m getting to publish a book with Penguin! I get to go on tour with Orange! I get to do a weekly mastermind with a group of guys I love. Our family did a crazy four week summer vacation/work trip. All of those things are a by product of daring to go on a adventure.

6. It’s easier to write books telling other people to chase dreams than it is to actually chase one of your own.

7. You can become a workaholic in approximately 4 seconds.
Your day never ends if you’re not careful. You’ll check the weather on your iPhone at the dinner table and the next thing you know you’re completely ignoring your family as you catch up on emails.

It’s been a crazy scary awesome year, which I think was also the title of a TLC album. I guess what I’m trying to say is if you’ve got a dream, you should try. I don’t mean quit your job, I don’t mean start a business. I mean anything. Try. Just try. I did this year and it was like everything and nothing I expected. Also, don’t go chasing waterfalls.

What is one thing you’ve learned about your job or your dream in the last year?

What a soldier on a plane taught me about perspective.

Tickets 3


I fly a lot during the spring and fall as I travel to speaking events.

I often try to talk to the people sitting next to me unless they are enveloped in a cone of silence, AKA headphones.

On one flight I was sitting next to a network engineer who helped run the IT department at a large company.

As we talked about his job, I asked him if it was stressful. He was in charge of a huge network, the technology was changing constantly and it seemed like he had a lot of demands on him.

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Sometimes empathy is a can of paint.

We often think empathy is complicated.

It is not.

All it takes is caring about what people we care about, care about.

And sometimes, as this video for a German home improvement store shows, that’s as simple as a can of paint.

Announcing the title of my new book!

Do Over

When you write a book you tend to obsess about how you’ll announce it.

You craft a thousand perfect opening sentences in your head for that first blog post. Sentences that make people laugh, clap their hands and maybe even cry a little right on their iPhones as they read your announcement. You annoy your wife, rewriting the intro over and over again in the kitchen. Or maybe that’s just me.

On April 7, 2015 I will release a new book!

The title is:

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Why I can’t sleep some nights.


“You have to tire yourself out each day or you’ve got too much spare anxiety left over to sleep well.”

Jenny said this to me over breakfast last week.

She’s right. For years, she’s always compared me to one of those dogs that the dog whisperer works with on that TV show. He shows up at the house, finds a boxer that is bored and fixes the situation by giving him a job. He has the dog wear a vest where he carries water bottles for the family on walks. He gets him a better exercise program. He gives him tasks. And the dog stops freaking out when he sees a leaf fall outside the window.

Though it’s not a straight comparison, I never eat shoes, it’s pretty close.

There are mornings I wake up at 5:15AM not because I’m some sort of amazing hustler, but rather because I am some sort of amazing worrier.

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