Blessings of a Headwind


I had lunch today with a friend with whom I had worked at Xbox.  We hadn’t seen each other since I left the company six months ago, so there was plenty to catch up on. 

In his world, so much has changed, including a promising new CEO, revolving leadership chairs, and more people stepping away from the business.  And as we talked about all the change and challenges, twinges of emotional trauma crept into my gut like ashes resurrecting from my burnout.   

Interestingly though, the trauma was quickly snuffed out by a soothing peace that has come from the distance of half a year – perspective of the kind you get from a satellite’s snapshot of our planet. 

But this peace wasn’t just from the healing of distance, time and a replenished tank.  It was a peace rooted in gratitude – gratitude for having had the privilege of working with incredibly talented and smart people, for a truly good company, on intriguing and gnarly challenges.

As I sit here in my kitchen in the early afternoon of a weekday, dog by my side, avocados in the fruit bowl looking at me asking what I’ll do with them for dinner, I am replaying something my friend said during our lunch. 

With empathy for my decision to revive by taking an indefinite career break, he told me of the time he took a two-year corporate time-out to sail the waters of the world. As refreshing and wonderful as it was, what he found that he missed most were the challenges.  Not the ones like figuring out how to fix his refrigerator miles and miles from land, but the ones that really squeeze the neurons.  It’s the headwinds, he said, that enable us to cut through the water with speed and power.  The headwinds give us strength.

Yes.  The headwinds…

I miss those gnarly challenges.  Not only do I miss them, I love them.  And not only do I love them, I need them. 

Like most everyone I suppose, I am at my best when I push, strain, and drive with might across a finish line that matters to me. Perhaps this is why I’ve always needed sports in my life.  Every single second on the field, course or court is a challenge, and knowing I left it all on the field, not an ounce of fuel left in the tank – well that IS fuel.

So I suppose the question for me now is which worthy challenge will I pursue next?  Which headwinds should I chose?  When do I venture away from shore?  Because staying in safe harbor too long, while lovely and so incredibly needed thus far, will be a slow atrophy of my strength and value.

I challenge you all to ask this question of yourselves…

What are you choosing?  Are you opting to play things safe in the calmest waters you can find?  Or are you pushing yourself into the headwinds, strengthening your muscles, fine-tuning your mind, and being the very best authentic version of you that you possibly can.

This matters more than almost anything I can think of. Creating you, the very best you, is your life’s most noble pursuit. 

Find your headwind.



3 responses to “Blessings of a Headwind

  1. I love that you recognize the danger of too-much safety and recognize the importance of stretching and growing yourself! And even if you don’t choose wisely, the beauty is you can always just choose again (I think you may have taught me that too!)

  2. Love the photo, the quote. And I loooove the title. I feel something really special and unique when you write. And it feels good, keep writing, por favor 🙂


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