The Art of Sucking at Things. Learning to Have Compassion No Matter What.

Recently, I was listening to what my friends refer to as "one of my bro podcasts", not that bro podcast, but the business and entrepreneurship kind, and the guest said something that stuck with me: "Sucking really sucks." Then he asked, "But what's the alternative? Never trying anything? Never taking a risk or learning a new skill?"

This hit me because I've been in what I can only describe as a season of aggressive growth. And with growth comes exposure. Lots of it.

In the past three years, I ran the NYC Marathon, bought a 100-year-old house that's still under renovation, and got married, all in the same year. I enrolled in a trauma training program at the Somatic Experiencing International Institute in a different state, requiring travel and time away from my practice. I wrote a chapter for a book on trauma. I expanded my business, hired multiple clinicians, and yes, had to let some go. I built out and decorated a much larger office suite and coordinated moving everyone there. This past fall, I gave multiple lectures, taught a psychoanalytic continuing education course and a dream workshop, all the while battling a full 6 weeks of a mysterious cold.

If it sounds like a lot, it was.

But here's the point of this braggy paragraph: I wasn't great at all of it. In fact, some of it I was objectively bad at.

The Discomfort of Being Seen

I really hate sucking at things. Especially things other people can clearly see me sucking at.

I hate the feeling of knowing something could have been better. I hate getting negative feedback that, if I'm honest with myself,  has merit. It feels awful. Like that lecture where I rushed through slides because I misjudged my timing. Or the first few months of managing a larger team, when I was clearly figuring it out as I went. Or presenting recently when I was sick and should have probably cancelled, instead showed up a little feverish, sounding much less confident than I actually was about the material. 

But as my bro podcaster alluded to, being bad at something, failing, sometimes publicly, is the only way to learn, grow, and eventually get better.

What The Research Says About Learning

Organizational psychologist Adam Grant writes extensively about what separates people who continue learning from those who plateau. In his book Think Again, he argues that the key isn't being right more often - it's being comfortable being wrong more often. He writes: "We learn more from people who challenge our thought process than those who affirm our conclusions."

Grant's research on "originals",  people who champion new ideas, shows that they don't actually have more good ideas than anyone else. They just have more ideas, period. Which means they also have more bad ones. The difference is they're willing to put those ideas out there, get feedback, fail, adjust, and try again.

He cites a study of highly creative individuals across fields, from scientists to artists to entrepreneurs. The most prolific innovators didn't have a higher success rate than their peers. They simply produced more work, which meant they failed more often in absolute terms. But those failures were the price of admission for their eventual breakthroughs.

Grant also emphasizes the importance of what psychologist Carol Dweck calls a "growth mindset" - the belief that abilities can be developed through dedication and hard work. People with growth mindsets see failure as information, not identity. They ask "What can I learn from this?" instead of "What does this say about me?"

Real Failures That Led to Success

Take Sara Blakely, founder of Spanx. Her father used to ask at dinner: "What did you fail at today?" If she didn't have an answer, he was disappointed. He taught her that failure wasn't the opposite of success; it was a prerequisite. When she pitched her idea for footless pantyhose to hosiery manufacturers, she was rejected repeatedly. One executive literally laughed her out of his office. She had no experience in fashion or business. But she kept going, eventually building a billion-dollar company.

Or consider Oprah Winfrey, who was fired from her first television job as an evening news anchor in Baltimore. Her producer told her she was "unfit for television news" and tried to change everything about her - her appearance, her delivery, her emotional investment in stories. She was devastated. But that failure pushed her toward talk shows, where her emotional authenticity became her greatest strength. She's said that getting fired was one of the best things that happened to her because it forced her to find a format where she could actually be herself.

In therapy, I see this play out constantly with clients learning to set boundaries. The first few attempts are usually clumsy, they either under-communicate or over-explain, they back down too quickly or come on too strong. They feel terrible about it. But each awkward conversation teaches them something about their patterns, their triggers, what works, and what doesn't. By attempt five or six, they're often quite skilled. But they had to be willing to be bad at it first.

Getting Comfortable With Discomfort

So how do we master the art of failure? How did I get through three years of enormous effort with mixed results?

First, we need compassion for ourselves. This doesn't mean lowering standards or pretending everything is fine. It means talking to ourselves the way we'd talk to someone we care about who's learning something difficult.

Second, we need to reality-test instead of catastrophize. When I got critical feedback about my pacing in that lecture, my initial thought was "I'm terrible at teaching and everyone knows it." The reality? I misjudged my timing on one section. Totally fixable. Useful information for next time. Not evidence that I should never teach again.

Third, we need to separate failure from identity. I gave a lecture that had rough moments. I didn't become a bad lecturer. I had an experience, got feedback, and now have data to work with.

The truth is we all make mistakes. We need to fail to succeed. And the more we try, the more we fail in absolute terms - but also the more we eventually succeed. The faster we can recover from a failure and integrate what we learned, the better off we'll be.

The Practice Principle

Here's where I'm going to do something out of character. I'm not a huge sports person (meaning I know very little about sports), but bear with me.

When Kobe Bryant was asked what made him one of the greatest basketball players of all time, he didn't just point to natural talent. He famously practiced longer and harder than anyone else on his team. There's a story about him showing up to the gym at 5 AM for additional shooting practice, making 400 shots before his teammates even arrived. He made countless bad throws in practice, thousands of them. He missed shots in games. He had entire games where nothing seemed to work. But he showed up, practiced through the failures, and kept refining his technique. This story has really stuck with me, and I admire the lesson in it. Do I know what team he played on? Not without double-checking on Google. Forgive me, basketball fans.

The same principle applies whether you're learning to play basketball, run a business, teach a class, or set boundaries with your mother. You have to be willing to be bad at it first. You have to practice in public. You have to miss some shots.

So What's The Alternative?

Going back to where we started: What's the alternative to sucking at things? It's staying exactly where you are. Never expanding. Never risking exposure. Never learning something new that might not come naturally.

That feels safe in the short term. But in the long term? It's a different kind of discomfort, the slow realization that you're capable of more but too afraid to try.

I'll take the acute discomfort of failing at something in front of people over the chronic discomfort of wondering what I might have been capable of if I'd been willing to suck at it first.

Because here's what I've learned from these past few years of aggressive growth: Sucking really does suck. But getting better? Well, I imagine that’s going to feel great.