Photo via Will Clayton

Last weekend I went on a midnight walk from my Orcas Island hotel room. Down at the nearby marina, I listened to saltwater lap the wooden dock and rigging gently knock against sailboat masts. Suddenly a leathery shape glided from beneath my feet and out through the water.

Spotted, with touches of light brown and cream, I recognized the sea lion. It swam and played near me for twenty minutes. The time was so peaceful and intimate. It reminded me that I haven’t depleted my life’s allocation of magic moments.

As I write this, I’ve been 30 years old for about a day. Turning thirty is no more significant than turning 29, just like passing one mileage marker on a road trip isn’t any more significant than passing the one prior. But it is more symbolic. It’s the difference between passing the mileage marker that says, “Welcome to Oregon” and “Rest Area: 52 miles.”

What does it mean to be thirty in a culture (and industry) that covets youth so dearly? Am I too old to have good startup ideas? Too old to put in the startup hours? Too old to inspire and change the world around me? I don’t think so. But I do have a plan to guard against it.

Donald DeSantis

It’s simply this: Do the crazy thing.

In any situation, when posed any question, what would be the crazy choice? Try that one. You will meet amazing people. And these people keep you young, curious, and strong.

For me doing the crazy thing meant leaving some great people and great teams. It meant traveling on last minute notice to places I’d never been to stay with people I’d never met. It meant thinking I could start a company, believing in myself despite all of my flaws, weaknesses, and simple adequateness.

Doing the crazy thing may ultimately end in my untimely destruction (there have been a few close calls), but so far it has never done me wrong. It delivers the moments of magic, danger, and adventure that keep life from becoming a boring slog, a routine. It’s a gift that, on my birthday, I’d like to give to everyone else.

Take it. Try it out. Let me know how it goes.

Donald DeSantis is a user experience designer and partner at LIFFFT, a product studio focusing on innovation and design.

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  • Paul Payne

    Happy Birthday, Donald. Welcome to the old entrepreneurs’ guild. I’m looking forward to more crazy.

  • Alan Ho

    Stay hungry , Stay foolish

  • grist_olof

    Happy birthday.  This whole cult-of-youth thing will change eventually.  

  • Dennis Ferrer

    Do it now because once the wife and family become dependant on the big company medical plan it makes doing the crazy thing tough.

    • Jen Zug

      Don’t blame the wife and kids. Blame the fearful state of mind and lack of adventure. @bryanzug:twitter happened to marry someone who embraces the crazy life and told him to quit his W2 job because the startup life is more fun.

      • Sick of the Self Indulgent

        BS. commitment to wife and kids means time and focus on them. plus financial security, health insurance, saving for college, being there at soccer games and helping with homework. you’re just self-indulgent and justifying it with a culture of “adventure” to look cool. get real. family is cool too – but it means a different lifestyle that startups discredit. Chrissy Hynes figured it out years ago: Pretenders – Middle of the Road► 6:40►

  • Guest

    Do you have a wife and kids?

    • donalddesantis

      Hi guest – I don’t have kids. But I do have a wife and mortgage. My wife is an awesome resource and partner. My mortgage is… a mortgage. :P

  • Poop

    Always really awesome to be on the receiving end of people doing crazy things!

  • Image Masking

     Happy Birthday Donald and i think you really enjoy that craziness :)

  • Tony Gavilanes

    Well said! I want sea lion interactions and foreverness.

  • It’s all good

    I just turned 30 and I’m trying the crazy things and move on. You make it seem so easy and it sounds great when reading it. I’m gonna try harder. Guess it may be different for the ladies.

    • donalddesantis

      Go for it. I try to do one thing that makes me uncomfortable, or is just unusual each day. One thing a day is a reachable goal. :)

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