The Cost Of Caring Deeply — And Why It’s Still Worth It

There’s an art to having skin in the game

One thing I remember about middle school gym class is that the cool kids never tried. Though I could sense the reason then, I did not have the vocabulary that I do now. The cool kids didn’t try because they were insecure. Many adults are the same. It is an easy trap to fall into.

Not giving your all on something you care deeply about can be a way of copping out. It gives you an excuse if things don’t go how you want them to. Giving your all, leaving every bit out there, exposes you. It makes you vulnerable. But that’s the point. This is what gives texture — highs, lows, and everything in between — to life.

It is a lot easier to give your all if you are okay with failing. If you are not okay with failing, you’ll protect yourself, you’ll do what the cool kids did in middle school gym class. If you are okay with failing, you’ll be more likely to put your skin in the game because your ego is safe regardless of the outcome. Herein lies a big paradox: being okay with failure makes you more likely to succeed, because being okay with failure gives you permission to not hold anything back.

This is a topic on which “soft” or “hard” dualistic thinking completely falls short. By being “soft,” in this case, being okay with failure, knowing you are enough regardless of the outcome, you are able to be “hard” and give everything you got, exposing yourself all the way.

My newsletter is the Growth Equation. My Twitter is @Bstulberg. My new book is The Practice of Groundedness: A Transformative Path to Success that Feeds — Not Crushes — Your Soul.