How Many Times Can You Embarrass Yourself Today?

Fellow Riskologist,

How many times can you embarrass yourself today?

If something’s important to you, are you willing to set aside all the funny looks and remarks of disapproval you might get by making it a priority in your life?

I ask for a very important reason. You see, the better able you are to ignore feelings of embarrassment, the better you’ll be at taking smart risks. And the better you are at smart risk-taking, the more good things will come to your life and work.

Don’t believe me? Just ask yourself: “Did my life get better the last time I passed up something important to me because I was embarrassed to do it?”

I think I know your answer. But let me illustrate my point with a, well, embarrassing story.

How a Newbie Embarrassed Himself Into a New Business

Earlier this year, I launched—and then eventually sold—a coffee subscription service.

I have never learned so much about business (or coffee!) at any other time of my life. And the reason is because in starting a coffee business, I had to push through so many embarrassing moments for the success of the company.

Two particular instances come to mind.

The first came when my partner and I were just starting to reach out to all the Portland coffee roasters to try to recruit them to work with us. Neither of us had any previous experience in the coffee industry, and learning how to talk to and meet with these kinds of people turned out to come with all kinds of embarrassing learning experiences.

The first roaster we met was Nossa Familia in NW Portland. I’d emailed the owner to tell him about our business and our wish to work with him. He followed up immediately, inviting us to come down to his roasting facility and do a “cupping” with him and his roastmaster.

If you don’t know, a cupping is a ritual that coffee connoisseurs do. It’s a pretty involved process that includes blind-taste-testing a number of coffees in a number of states of preparation.

When you know what you’re doing, it’s a pretty fun experience. When you don’t, it’s intimidating.

I was excited, but there was a problem: I’d never done a cupping before, and Augusto—the owner—was going out-of-town, so we had to meet soon.

I looked up some articles online about how a cupping works, but I was pretty unprepared when we arrived.

As soon as the cupping started, everyone was acutely aware that I’d never done one before. I knew I was going to be embarrassed. And I was embarrassed.

Augusto—being the nice guy he is—lead me through the process and now I’m totally familiar with how a cupping works.

I knew going into the meeting I would be embarrassed. But what was my other option? Say no to the meeting? Put off my dream of starting the company even longer?

Hell no! This was important. I went to the meeting, embarrassed myself, learned a lot, and moved to the next thing.

The second embarrassing moment came just before we launched. We were opening shop the next morning, and we still hadn’t figured out the best way to ship our coffee.

The problem was that there were so many options. I had at least 10 boxes from USPS to test different packing styles, but somehow it was now 7:00 PM and we didn’t have any coffee in the house to actually test with.

This was critical. We had to figure something out! Where could I find enough bags of coffee on short notice to test different packing styles? The grocery store, of course!

I knew I was about to embarrass myself, but the success of the business had to come first. I grabbed four or five different boxes and headed to the store. I went directly to the coffee aisle, pulled about 20 bags off of the shelf and proceeded to sit on the floor stuffing boxes and taking pictures.

Thanks to Murphy’s Law, the store was packed, and people were walking up and down the aisle staring at me, wondering what the hell I was up to. I didn’t lift my eyes even once.

Pro tip: This actually helped. People seem to pay less attention to you when you act like the weird stuff you’re doing is no big deal.

I was so embarrassed, but I continued to stuff box after box until I’d tested every possible option. And guess what? That embarrassing trip to the store saved us a bunch of money in shipping costs because I found a way to pack a smaller, less expensive box than I originally thought we’d have to use.

I could have let my fear and embarrassment stop me, but successfully launching the business was more important.

Engineering Embarrassment: One Easy Hack to Overcome Discomfort

In your day-to-day life, there are probably many things you tell yourself are important. But do you actually do the things necessary to act on those things you say are important? If yes, congrats! You win! But if not…

Check yourself. If you’re afraid to do something important because you’re afraid it’ll be embarrassing, it’s not actually important to you. What you spend your time on is what’s actually important to you.

And at some point in the past, those things were also embarrassing because you were new to them and didn’t know what you were doing. Yet here you are today.

If you want to take smart risks in your life, it’s imperative you learn to deal with embarrassment.

The way I like to do it is by harnessing it in my favor and using it to motivate myself. If there’s something I want to do, but I know I’ll struggle to get over the embarrassment of starting, I’ll engineer an even bigger embarrassment that will come to play if I don’t do it.

My method to do this is public accountability. I absolutely hate telling people about something before I’m ready to, but I know if I commit to something, I’ll do whatever it takes to keep that commitment. I’ve learned that missing a commitment ends in much worse embarrassment than anything I’d have to do to keep it.

Going back to my examples of launching the coffee company, we’d announced a launch date for it, and I was fully committed to meeting that date.

Missing a launch date—for me—would result in unfathomable embarrassment. With that reality circling daily in my brain, there was simply no way I was going to let the embarrassment of not knowing how to do a coffee cupping or stuffing boxes on the floor at the grocery store stop me from coming through.

Your Homework Today

Today, I want you to ask yourself: “What is something that would be incredibly embarrassing to me?” Then, engineer that embarrassment into the things in your life that you say are important but that you’re not taking action on.

The goal is to give yourself a sense of scale and perspective. It becomes easier to do the little things standing in your way when not doing them becomes much worse.

Feel free to share your plan of action in the comments.

Yours in risk-taking,

Founder, Riskology.co