Announcing “Ask Jerry”

TLDR — Jerry Colonna, the author of Reboot: Leadership and the Art of Growing Up and CEO of executive coaching and leadership development firm Reboot, is teaming up with Andy Sparks, coach-in-training and co-founder of Holloway and Mattermark, to write a weekly advice column that explores the psychological patterns that cause our highs and lows, and wins and losses.

To celebrate Jerry and Andy’s launch day, we’re offering 25% lifetime discounts for the next 24 hours.

Lately I’ve been crying a lot. But not in a bad way. In a healing way.

Take, for example, the Ted Lasso incident. One minute I’m sipping a malbec, enjoying what I thought was a vapid goofball comedy — and the next I’m sobbing into my wife’s shoulder, confessing that I’m often more focused on the goal than on the team, and that I often inhabit a sort of hyper-rational mode because I’m afraid to show the people I work with how much I care about them.

Maybe I just need more sleep. Ok, I definitely do. But also, I think something deeper is going on.

I’ve come to believe that work is more emotionally difficult than our culture makes it out to be. We’re supposed to just plug in, but it rarely works that way. Instead we feel resentful, or scared, or bored.

The common solution is to stop caring so much, to not invest so much of yourself in your work. But that’s not what most of us really want. We want to bring our whole selves to work. To see our fingerprints in what we produce. To feel a kinship with our team.

So the choice is either to push it down and cope with the feeling that we’re missing something, or to investigate it. Jerry calls this latter path “radical self-inquiry.”

The premise, as I understand it, is simple: the more you understand your feelings, the less your feelings control you.

The more we can identify and work with emotions — inside ourselves and inside of others — the more rewarding work can be. Often this is what’s really going on inside teams that win. They’ve figured out how to click into gear because they understand themselves and each other.

But this clicking thing doesn’t happen automatically. It’s not cheap or easy. It requires work — work that’s often painful. It requires courage, insight, and honesty.

And