Walking the tightrope

Trusting yourself again after a big mistake

Hello, I’m Suzan. Thank you for reading Observations and Annotations — a newsletter exploring leadership, psychology and organizational dynamics through real life stories. I try to make this one of the best emails you get this week. It’s one of my favorite things to write. If you enjoy the content, please like and share it.

This is the third in a series on how leaders learn on the job. We looked at feedback loops as a mechanism for leader learning, then on the role of shame, guilt and perfectionism. This edition the focus is on how leaders can trust themselves after a costly mistake or after a series of them.

We moved 10 days ago so I’m composing this from my new space. As you likely know, moving is one of the top stressors for most. Not far behind the death of a loved one and divorce. Then add timing — in the waning days of a year-long pandemic and we had a recipe for a fraught move. The actual move part was pretty easy. The before part was fraught, especially the decision making.

This past year was hard for everyone, ours compounded by a bad apartment. We were moving just as the pandemic was settling in. We didn’t have time for both of us to see the place and our neighborhood has limited options so I went to see the place alone. He trusted me, agreeing to a lease before even seeing the place. There were three bedrooms so we could each have our own office. The location was close to the subway and all our favorite places. We knew the neighborhood so that would make the transition less demanding.

But.

There were bugs everywhere. My partner was bitten by a bug so bad I worried I'd have to transport him to the hospital. My office on the first floor looked out onto the street. As I worked, people talked to me through the window like I was an animal in the zoo. In my perch I saw every ambulance and fire engine go by, jangling my nerves. I had to retreat to the dark basement to get any privacy. Finally, the apartment was so dark it felt like being trapped inside a tomb. Oh, and our rent was increasing at the end of our lease too. It was the worst place I’ve ever lived. Well, tied for the worst. The “winner” of worst places had a string of break-ins and a bathroom that looked like it belonged in the film The Silence of the Lambs. I finally left when the cops told me it was a matter of when I’d have another break-in, not if. Despite this, I still had a tiny amount of nostalgia for that place. I felt zero nostalgia for our current one.

Though normally I dread moving, this time I counted the days. We started looking early. We thought we'd get a sense of the market. Give us time to assess, build a spreadsheet, carefully sort through options. We sat down one night, side by side searching on our computers. An hour in, I saw it: 2BDR, 2BA with hardwood floors, ample closet space, flooded with sunlight on a tree-lined street in our neighborhood. I knew immediately. This was our place. No matter that it was much smaller or that it was three months before our lease ended. I recognized it like when my friend told me she met this cute dog named Maddie who needed a new home. I knew she was mine before I even set eyes on her.

We made an appointment for the first time it was shown. As we walked in, that familiar feeling returned. This was our place. As we left, a string of couples lined the street waiting to see the apartment. This one was going to go fast.We raced down the block stopping on a corner to put in a deposit taking it off the market, dashing their hopes. I was giddy. We did it. We were really leaving our terrible apartment for better environs.

That night fear sunk in. I worried it was a mistake. After all, my track record with places wasn't great lately. We didn’t have a spreadsheet, we only looked at one other place. We made the decision too quick. I called four people to talk it through, to make sure I was thinking clearly and hadn't made yet another apartment mistake. I went over the details: on a leafy street, four minutes from two train lines, with loads of light and closet space, 30% cheaper than our current place. It wasn't all upside. It was much smaller which meant every single item mattered and we'd have to get rid of five pieces of furniture. We'd be further from our favorite places and have to leave behind our beloved neighbors, the ones we'd commiserated with throughout the pandemic. We'd have to sleep in the living room. Not such a big deal for New Yorkers and we'd done it before. It would allow us to each have a private office but this place would take some creative thinking to make it feel spacious. And, we’d have to pay double rent for two months. Ouch.

Every single one of them told me I was indeed sane. I wasn’t making a mistake. I could trust myself. I'd like to say that my worry evaporated after those reassurances. My mind eased but the nerves didn't fully go away.

Could I trust myself? What if I'd made a mistake again?

I had to trust myself at a time when my trust was the lowest, after making an ill-advised decision. In New York City you have about 10 minutes to look at a place and decide if you want it. There are always downsides you don't anticipate -- loud neighbors, unexpected construction or little creatures who become your uninvited roomates. You have to take what you can observe, knowing it won’t be perfect and then listen to your instincts. Pretty much everyone has a renting horror story. Renting an apartment in New York City is not unlike the conditions leaders face, especially when it comes to mistakes.

The responsibilities pile up when you’re in charge of an area. You don't want to disappoint others. Your mistakes have consequences not just for you but many others. This makes you cautious, careful. At first the mistakes are easy to overcome, then they pile up or you make a really big one that costs the company a quarter of their revenue or results in losing the team’s confidence. Your trust in yourself erodes.

Worrying you can’t trust your gut, you become more analytical. You try to root out every single fact, relying on spreadsheets and hard data. When responsibility weighs heavy, it's easy to get your thoughts tangled, to confuse over thinking for being analytical. When leading you can't eliminate uncertainty or ambiguity. You will never have enough data. You can never guarantee an outcome. You can't spreadsheet your way to certainty. Uncertainty will always remain.

The one certainty? You will make mistakes — maybe even many of them. After each mistake you’ll have to trust yourself again despite this. If you don't trust yourself, you won't trust others. They probably won’t trust you either. That trust bank will grow grim, eating into your confidence. Decision making will slow as you try to identify every speck of information to make sure-thing decisions.

You have to know you have enough information to trust the patterns you’re seeing, to listen to that instinct luring you in one direction. You need to find the balance between having enough data, trusting your instincts and not letting your fear of making a mistake rattle you. Unless you learn to trust yourself after a mistake both perceived and real, leadership is going to be mighty uncomfortable.

Postscript

After a bit of fretting, I started to focus on all the past decisions I made that were great —the apartment that helped us get out of debt, adopting my dog, saying yes to husband on a park bench in Central Park. It eased the nerves. The moment I stepped into the new place on moving day I felt buoyant. Despite standing in a sea of haphazard boxes, those frazzled nerve endings became still. My instincts were right. The new apartment is lovely. We’re 100% happier. It’s clean, no bugs. It’s so bright we don’t turn on the lights until after dusk. The neighbors are friendly and helpful. Sleeping in the living room is actually pretty great. I feel so relaxed I took my first nap in months. That extra money in our account every month will help us get closer to the goal of buying our own place. I’m so glad I trusted myself.

Here’s a peek at my new work space.

What else to read

Good leaders are good learners.

Research on learning from errors.

My biggest leadership regrets.


Written by Suzan Bond, a leadership coach and former COO. Based in Brooklyn. You can find me elsewhere on Twitter and Medium. Comments or questions about leadership or scaling startups? Send me a note.