There’s a trend with accomplished high achievers. Mistakes haunt us like banshees and we never feel like we are good enough. Hating ourselves can be motivating (fail fast, move forward faster?) but can also debilitate us. Sometimes I wallow in a well of self disgust so deep that I cannot climb out to brush my own teeth.

Apparently, there are a lot of other ‘well dwellers’ out there too.

I was recently at a global conference for overachievers. It was at a far away place where we could come together to create companies, films, funds, and discuss our personal neuroses while clinking cocktail glasses, some half empty.

My longest term relationship is with a lady called self-loathing,” a prominent producer told me. “We take romantic getaways to very dark places.”

“Dark? Oh I know dark. After my divorce, I debated suicide,” confided a female entrepreneur. “I had clearly fucked up my personal life while fundraising and felt I wasn’t worthy of the capital.”

“I feel dark as part of my career,” said a musician. “Before going on stage, I vomit. I always come to the realization that my work is total shit and I’m duping the audience.”

From the outside view, these people appeared to have it all-talent, success, and community. However, if you journeyed inside their heads, you’d find they were holding their happiness hostage, shackling it with chains of unforgiving insecurity. They flogged themselves for never reaching an impossible projection of themselves.

The management consulting firm McKinsey is known for hiring what it calls“insecure overachievers” — people that get straight A’s in everything including self doubt. Perhaps McKinsey thinks this trait makes people work harder. After all, no one, especially insecure overachievers, wants to be ‘found out’ that they’re not perfect. Most overachievers hail from the land of Lake Wobegon — where everyone is all above average, all of the time.

However, I’m not sure habitual self flogging leads to grandiose work. Some insecurity does help us keep our edge, providing a helpful snort of adrenaline laced with humility. But just like party drugs, too much can be self-destructive to both achievement and personal health.

We need to hold onto our personal spirit to take risks, see new paths, and know when to say “Fuck work — I’m going on vacation with my family.” Self loathing shouldn’t blind us to life. If we can make peace with what we don’t do well, maybe we can double down on what we’re awesome at, career or otherwise.

Plus, every time I beat myself up, my friends point out that I’m being a bit selfish. “You’ve forgotten all the things you’ve done,” said one.

“Worse, you are neglecting all the things you can do because you’re too busy complaining,” said another.

They were right-there was a better way to channel my energy.


The first step in remedying our feeling of ineptitude is to take our projected ideal off of the pedestal and start eating a little humble pie. We are all human, after all. We need sleep, make mistakes, and are slaves to emotion.Even the greek gods screwed up, turning each other into inanimate objects out of storms of jealousy. Anytime I feel bad, I remember that at least I haven’t turned someone (or been turned into) a stone, stag or laurel tree.

When I am open about my mistakes, I give permission for others to be open about theirs too. Other designers and I unite in our trials and tribulations. Some call it vulnerability. I call it just being honest. Honesty fosters trust, connection, and positive impact.


Uniting over ineptitude only gets us so far. We still need to climb out of that well to brush our teeth and get on with our days. It is important to recognize the positive we DO create in the world, because let’s face it, we do, even if it isn’t as delicious to wallow in.

My good friend Plum decided that instead of commiserating over terrible things that happened to us, we should celebrate the positives. When we travel, she mandates that we count our daily “wins” as we toast each other at dinner. “Wins” could be good things that happened during the day, or good deeds performed, even if it was as simple as drinking enough water. At first, I complained. It was easier to focus on the glass half empty and lament how we messed up. Then she asked me, “What would you rather drink? A glass half full — of champagne — or half empty?” Right.


If you are a religious sort, you will take your body and mind as a gift given to you by whatever Supreme Being you worship. It’s an amazing thing, to be alive. For those of us born into secure socio-economic stratas, we have a lot to be grateful for. Instead of spending our time thinking about ourselves, we should start thinking about leveraging our position of privilege for others. High achievers that have figured out how to be happy spend time outside of their own lives. Some, like Plum, volunteer with the SPCA. Others teach ESL students or spend time in retirement homes. They tell me that every time they do something for another living being, their energy focuses outward. It’s hard to stay mired in self loathing while you are seeing an elderly person smile while petting a dog.

According to research, people that volunteer are happier than the rest of the population and may have a 22% longer life. Of course. They aren’t wasting their free time thinking of themselves. Instead, they’re actively making someone else’s life better, increasing positive energy in the world

It’s not necessarily a bad thing to feel like a failure on occasion. It’s human. It’s also a basis for a lot of my poetry.

But I’ve found that I can achieve more in life when I make peace with my shortcomings and harness positivity to leap forward.

Often the better way to live isn’t to improve ourselves, but to seek to improve the world around us. We could spend an hour reading a self help book, or we could spend an hour actually DOING something. As a side benefit, we’ll also be able to drink a full glass of champagne at the end of the day.

**originally posted on Medium here

(Visited 132 times, 1 visits today)