Don’t dwell on the losses

This is part I of a III-part series, in my Unforgettable Faces column, where I interview someone close to me who has continuously offered me guidance along the way.


“Can you remember a time when you just completely fucked up? To the point where it haunted you months later?”

I was on the phone with my friend-slash-mentor Amanda, the first supervisor I ever had in my career, and someone I still called for advice years later.

“Ummmmmm,” she said, “Not really.”

Never? A simple text or email asking, “What’s the status of this?” or “Have you started on that?” can spin me into a dimension of PTSD I can barely explain. It reminds me of nights I once laid awake at 3AM, thinking of all the projects I was either A) behind on or B) forced to completely ignore due to other priorities. I would lay there in sheer panic, thinking about whatever nightmare deliverable or due date awaited me in the morning.

“You’ve never been screamed at or ripped apart in a meeting before?” I asked.

“Well that’s the thing about Jon,” she said, referring to the CEO of the company that gave me my first internship—the same company she still worked for. “He lets you know when you haven’t done your best work, but he won’t scream at you. Everything comes from a coaching mentality.”

I thought of the times I witnessed an executive throw what could only be referred to as a two-year-old tantrum. Episodes so outrageous they made you paralyzed and inefficient in your work, with all mental resources spent dreading the moment you made a mistake.

“I don’t like to dwell on failures or losses,” she said. “I block them out of my mind. I just say, ‘Well, that sucked,’ and, for whatever reason—I just move on.”

When she said it, I realized that’s what I wanted.

When I worked for—under?—Amanda, I was twenty-one years old. Hired for a three-month internship, Amanda was the one who pushed the company to keep me on for the duration of my senior year of college. I learned so much at that place. And they put way more trust in me than someone with zero experience deserved.

And I fucked up. Ohhhhhhh did I fuck up. So much so it’s almost comical. I once deleted all the CRM activity data in the entire company. If you don’t speak Salesforce, that means I deleted ALL record of EVERY CONVERSATION between a sales rep and a prospect—EVER.

Yes I did.

But, to Amanda’s point, I never dwelled on it. I dwelt less on those mistakes than on mistakes I’ve made in more recent jobs—with half the magnitude.

I guess you could chalk it up to a difference in company culture. Amanda’s employer embraces losses and learns from them. I went on to work for companies where mistakes were a burden—something covered-up and hidden from the leadership team, so no one got the end-benefit of learning from mistakes and everyone ran the risk of repeating them.

But let’s be real here: Company culture plays into roughly ten percent of it. The other ninety is me.

Somewhere in the six-plus years that I left that internship, I learned to dwell on and fear my losses.

I learned to regret my mistakes, to the point where I would rather avoid confronting an employer, collaborator, client, or colleague. I would rather hide from the situation than throw up my hands and say, “Not going to lie here, I’m  slammed and I just haven’t gotten to it yet.”

I learned to dread the repercussions of a failure or loss, rather than take a risk and say, “Well. That sure as hell didn’t work.”

But it’s those risks that teach us how not to do something. It shows us which strategies don’t work.

It gives us a better estimate on how much preparation goes into a project. It narrows down, out of the hundred ways to tackle a problem, which ninety-eight won’t get us toward our end solution.

If I haven’t done the prep work I promised to a colleague, I overestimated by bandwidth. If I spend triple the amount of time as predicted on a project, I didn’t do my research. If I write ten iterations of copy and none of them stick, I need to dig into the client and find out what I’m missing.

Our mistakes and losses are nothing to fear. They’re nothing to hide from. They’re certainly not something that should cause a visceral reaction from a text or email. That does nothing but prevent us from tackling new challenges going forward.

Just throw up your hands, say that sucked, and move on.



More about Amanda: Amanda was the first manager I ever had in my life. At just twenty-five years old, she carved out a brand new department (with me as their intern!); and before age 30, she was pitching Fortune 500 companies. For the past seven years, she has worked for the fastest-growing company in Iowa, which has grown from just north of 100 employees in 2011 to nearly 800 today. 

Tomorrow’s advice from Amanda: Be 100% in it.

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For All the F Words
You have flaws. You f-up on a daily basis. And that should be ok.