I always laugh when I hear someone ask, “What was your most embarrassing moment?”
Do you seriously think I would ever tell you?
For normal people, their most embarrassing moment involves shitting their pants at the age of 26, getting brutally rejected when proposing to their girlfriend of 3 years in front of a crowd at Central Park, or quitting their job and showing up to the new, better job on the first day, only to find out they never actually got the job.
I know people who have done all of these things. You should have seen me laughing as I wrote that last paragraph. God I love it (also, I’m going to hell).
So while I really like you, I’m sure as hell not going to tell you my most embarrassing moment.
But I WILL tell you some things that have gone wrong recently.
Failure #1 – I royally screwed up my chance to talk at TED
A few months ago, I got introduced to the woman who chooses the speakers at TED. I couldn’t wait to talk with her — speaking at TED has been a dream for years. So I got ready, took a taxi to the meeting, and waited in the lobby to meet her. When she came out, we made small talk, then she said, “OK, what do you have for me?”
I had come up with a few ideas over the past couple of days, and I pitched her. As soon as the words came out of my mouth, I could tell it was over. There was zero reaction. She said, “As you know, our audience includes people like Bill Gates…how would this appeal to him?” My response was as weak and sickly as a Russian orphan. As she walked me out, she didn’t even say, “Let me know when you have a better idea.” Instead, she said: “Nice to meet you. Thank you for coming in.”
It wasn’t her fault. It was MINE. I hadn’t done my normal level of preparation, and it showed.
Failure #2 — Brutally rejected at a bar
I hit on a woman at a bar, only to find out that she wasn’t interested. Here’s why.
Failure #3 – An IWT product you’ve never heard of
Earlier this year, I came up with an awesome idea for a new course. My modeling indicated it would generate over $1mm/year. It would be totally new, but pull from a genius business model invented decades ago. And it would be massively scalable.
I spent 3 months doing my own research, then I excitedly turned it over to the IWT Product Team. I told them to look into it and build off of what I’d initially done.
They came back about 2 months later with one recommendation: NEVER DO THIS.
This has happened before. On our team, we have a nice balance of “Irrationally Optimistic” (me) and “Extremely Guarded And Wary Of Ramit’s Crackpot Ideas” (my team). However, I usually get together with them and it ends up working out.
This time, they put their foot down. They showed me 10 different reasons why this would never work. They showed me more sophisticated models than mine. And they showed me several points I hadn’t thought of.
Finally, after investing 6 months of heavy research, with a heavy heart (just kidding, I have no heart), I killed the project. They were right. I was wrong.
There’s no happy ending to the story. THAT’S IT! I didn’t turn it around and make it into a charity benefit that helped poor Korean kids. We just spent $50,000+ and our research is now shelved away, probably never to see the light of day. Damn that sucks.
Why I’m sharing these failures with you
As you may remember, I keep my failures logged in a Gmail folder. I did not wake up today and plan to share my failures with 500,000+ readers. Shit, I’d rather spend all day writing about how great I am. Wouldn’t you??
But I’ve also learned that the most successful people are counterintuitively the most open about their weaknesses.
For example, if you ask a top performer, “What are your weaknesses?” they’ll laugh and say, “How long do you have?”
Then they’ll be brutally honest about the EXACT shortcomings they have: They have trouble prioritizing. They are struggling with work-life balance. They tend to rush things when it gets stressful.
Notice that less experienced people will instinctively try to hide their weaknesses. As if we can’t spot them from a mile away.
Why we hide our failures
As a guy who became expert at hiding my weaknesses (“Skinny Indian guy…” “Will she like me because I have hair on my chest?” “Lowest math grade in my class…again…”), I understand WHY we don’t like to share.
I’m reminded of one of my favorite speeches from the West Wing, where presidential candidate Santos talks about how we’re ALL broken.
And yet over time, I came to LOVE and SEEK OUT failure.
Because each time I failed, I learned something new. And with each failure, I broke through a small barrier, which cumulatively helped me achieve mastery.
Without failing 2, 3, 100 times, I couldn’t be successful. In fact, I still fail at over 50% of new initiatives. And I’m good at what I do!
I want to show you one technique that’s been instrumental in my life when I’m facing the fear of failure or even judgment from other people.
Warning: This technique is deceptively simple but can completely change your mindset.
How to handle fear of failure and judgement
When we’re facing the possibility of failure, our minds go in a hundred different directions to try and convince us to take a different path. You can calm your inner critic by using the “What if I Were Perfect?” Technique.
To do it, you trick your mind by thinking about how a perfect, competent, confident person would handle this situation.
- You might say, “I’m not sure if this job is something I want to do for the rest of my life.” You doubt applying, then decide not to do it, then stay miserable in your current job…and miss out on a potential dream opportunity.
- Using the “What if I Were Perfect?” Technique, you could tell yourself, “I know this decision isn’t permanent and I could easily change course if this one isn’t right for me.” You apply, and maybe it doesn’t work out, but maybe it does and you find a new job you love.
You can use this new technique EVERYWHERE. Your love life (asking someone out), your job (approaching your boss about a raise), or your social life (going to that new painting class even if you don’t know anyone).
This technique will help you become aware of your mental barriers and defeat them before they hold you back.
Your challenge: try the “What if I Were Perfect?” Technique to overcome your fear of failure
Now, I want you to think of one thing you want to try this month…but you haven’t done it yet because you’re scared of failing. Tell me how you’d typically respond, then give an example of how you could use the “What if I Were Perfect?” Technique.
I’ll start with one that got to me for years, hosting events:
Typical approach: “What if I hold this event and nobody comes? That would be embarrassing. Forget it. Maybe I’ll host a party next year when my audience is bigger.”
WIIWP: “I’m going to make this a can’t-miss event. Even if hardly anyone comes, the people who ARE there are going to talk about it for months.”
Your turn. Leave a comment below with one way to use the “What If I Were Perfect” technique then check out what other people have to say. Let’s see how many examples we can come up with.
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