How to Fail and Feel Good About It

I speak from recent experience. Watch me spill my guts.

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to be successful and satisfied at work — and build a career or company you love.

Today’s one thing: Succeeding.

That one thing, better: Failing first.

Made with DALL-E

You want success. So why won’t it just come... easier?

Haven’t you put in the work? The time? The agony? Why isn’t the reward just there already!?

I’ll be honest: This subject is raw for me. Last week was tough. I wanted success and I fell on my face.

I was crushed for a minute. Then I found something to pick myself back up.

This is what I want to give you today — the way to pick yourself back up. To feel better. To see better. To become better.

Maybe it’s not perfect, but it’s the push I needed... and I think it’ll help you too.

So let’s get personal.

There’s no good way to say this, so here it is: Last week, I launched a premium version of this newsletter — and it did not go as I’d hoped.

At the start of 2023, I set a goal: I wanted my newsletter to be very valuable to people, and to also be financially self-sustaining. The first part went great — I’ve built an audience of 45,000, and have been gratified by the many personal responses I get.

People often email me questions, so I built a premium offering to be more directly helpful: I’ll write more newsletters — including an advice column, often based on reader questions — as well as host monthly “office hours” video calls. On Thursday, I nervously sent out my launch announcement.

A total of 14 people opted to pay.

Let me honor the importance of this: These 14 people bought something they’ve never experienced before. In fact, they’re just buying the idea of something. They’re paying because they trust me. That is humbling. It is an honor. I never, ever want to forget or diminish that — and I’ve written them directly to say so.

But if we’re talking pure numbers, 14 is 0.031% of my newsletter subscribers. So as grateful as I am, I just… thought it would be more.

To be clear, I am NOT here to make you feel guilty. I am instead here to commiserate with you — because I’m sure you’ve felt this too, when your own efforts fell short of your expectations.

Like you, I felt a wash of panic and embarrassment. Maybe I’d miscalculated? Maybe I’m just not good enough?

Then something changed everything.

I went to LinkedIn. I started scrolling. I was looking for... I don’t know. Distraction?

I came upon this post from Kara Goldin, the founder of Hint Water, who I’m friendly with. It read in part:

“I needed to hear that today,” I thought to myself.

And then I thought: OMG. OMG!!!!!!

Because here’s the thing: People often say that to me, after they read something I wrote!

But if I’m being honest, it’s been a while since I felt like a failure — which means it’s been a while since I could deeply, emotionally relate to what my readers were saying.

That’s when I thought three magic words — the words that make all this better.

I thought: This is useful.

This failure is useful! It helps me relate more to the people I serve! It gives me new ideas. New insights. And it gives me a mission — to do even better. 

Now, here’s the question to ask yourself:

What is your failure for?

Really emphasize that word — for. What purpose can it serve?

Failure can feel like a dead weight you carry around. As if you swallowed it whole and must let it sit inside you. This kills you because you — because we! — are people of action. We want to do things. But failure feels like the end of action.

So what if it’s not?

What is failure for?

I guarantee it is for something. It serves some purpose. It is a key designed for a specific keyhole. The new tool that completes your mission. The weapon that slays the next beast.

Some founder friends have told me, “You didn’t actually fail.” Launches are hard, they say. People need time to decide. And 14 is pretty good for a new product! I acknowledge all this. And again: I am so incredibly grateful to those 14 people. But it just goes to show — failure is a matter of perspective, and I needed to fix mine.

So, uhhh, should I have written all this?

Some could argue no. But here’s why I did.

Last week, just before my launch, I interviewed a leadership expert named Jacob Morgan. His new book is called Leading with Vulnerability, and he says we have vulnerability all wrong.

We’ve come to lionize vulnerability at work — to treat it like a form of currency. If I’m vulnerable, the thinking goes, people will like and trust me more.

Jacob surveyed 14,000 employees and found something more complex. “Purely being vulnerable at work can cause you far more harm than good,” he told me. “But leading with vulnerability is different.”

What’s that? It’s admitting a weakness, and then following it with a plan. “Vulnerability creates connection, but you must also demonstrate competence,” Jacob says.

This is the final lesson I draw from this experience. I would not have simply told you that I failed — because that’s selfish and unfair. So instead, I’ll tell you my plan. I’m going to start exploring a few things, including:

  • The offer. Maybe it missed the mark. Should I just write more regular newsletters? Do people want an advice column and video chats? What do you think? Reply and tell me!

  • The pitch. I paired my newsletter announcement with a second one. Maybe that was too confusing. I’ll refine how and when I talk about my offerings.

  • Time. Maybe my expectations were off. I wanted a big pop, but perhaps this business just grows best over time.

My goal is to build something that helps people — and I have that chance! It starts by serving those 14 people, who I owe so much to. And as I get it right, they’ll grow to 140. Then 1,400. Then more. (Want to get in early? Upgrade here — I will go all out for you.)

Because that’s what we do when we fail, right? People of action do not just sit around, inactive. No. We figure it out. We use everything we have, even when it’s hard, especially when it’s hard. We take the long way there, because the short way doesn’t exist. This stuff sounds cliché, I know, but that’s because hard is hard is hard, and everyone’s experienced it, and the best of us put it to use and live to tell the tale, and that’s what you and I will do too. 

That’s how to do one thing better.

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P.S. Miss last week’s newsletter? It was about how to be happier with what you have. Read!

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