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What do you do when your project, business, or startup fails?


how do you react when your business or startup fails?

I received a letter tonight

I don’t know why I did it. Really, it wasn’t something I normally do. But I noticed I’d not received any emails from my website’s contact form. So I headed to the form plugin directly and exported the entries.

Maybe, I thought, no one is emailing me. But I was wrong.

There was two months of contact forms filled out that for some reason hadn’t reached me.

And in there was a special email from a stranger.

It was from someone who saw me speak

They had been to a WordCamp where I had spoken earlier this year. They’d heard me talk about the impostor syndrome (video link).

In it, I share a part of my own story – where I quit several times (my six year old son, watching me give this talk turned to the person next to him and said, “He sure quits a lot.”) And each time, I quit because I was afraid of being caught. A fear that existed because I was unable to internalize any of the success I’d had.

As it turns out, this person had been at one of my impostor talks. They’d heard it. And they’d appreciated the honesty of my story.

They were fighting their own impostor syndrome

As it turns out, they were fighting it in their own life. And they were especially feeling it now, because their business had failed.

That’s the worst, isn’t it? You already feel like failure is just around the corner and then when it happens, you have no trouble believing you are the reason it all fell apart – regardless of the truth of the situation.

It’s depressing and painful.

How do you respond when your startup fails?

I don’t know about you but the fear of failure, a big enough thing to deal with, is only exacerbated by the reality of failure, especially when you’re dealing with the impostor syndrome.

Have you been there? Have you ever been facing the situation where your business, your freelance effort, or your startup fails?

It’s not fun. And if you were the person in charge, it can leave you immobilized, paralyzed by the fear that others will find out.

One of my five startups failed.

I’ve told you before that I was a part of five startups before I joined my current employer – a non-startup. Four of the five times, the results were pretty good – we were able to sell the first two, and the third and fifth went on to be sold after I left (but used technology solutions I’d been a part of designing and building).

But that fourth one. That was brutal. We worked like mad. Educated a market as a first mover. And we spent time and money building a reputation.

Eventually it was clear that the US market wasn’t going to adopt our approach to the problem we were solving. Others came in and won the market, leveraging much of our educational materials. And we closed down shop in the US.

Failure sucks. Until it doesn’t.

It took a long time to get past that failure for me. It’s not that I thought everything I touched would work – remember, I struggle with internalizing success.

No, the issue for me was that I struggled to take away any good lessons learned. And because of that, I feared that I would find myself in the same spot again.

Who knows, maybe one of the underlying reasons I’ve stayed in the enterprise and corporate world this long has been driven (deep down) by a desire to first “understand” the failure, before taking the risk of entrepreneurship again.

Ironically, it was in coaching other startups over the last decade that I found my answer.

There aren’t perfect formulas for failures. The truth is that we don’t control nearly as much as we sometimes think we do.

And in the end, failure is just a way to develop empathy for another person who will find themselves in that same place later.

This person’s next step inspires me.

Me? I was pretty quiet about that fourth startup. Never really talked about it. Didn’t mention it to friends.

I quickly joined another, worked hard for a year, and then moved on as my wife and I had our first child.

The last eight years have been here at Emphasys, while I’ve worked in my spare hours coaching and helping WordPress companies with product development and strategy.

But this email I got took a different road than I took.

They owned their situation. Talked about it up front. And then went on to ask me something.

If you’re like me, you would have guessed they were looking for some kind of hookup. Some trading on the fact that they started out by complimenting me, or the loosely related fact that we attended the same event together.

But that’s not what they asked. Instead, what they asked inspired me in its simplicity and power.

“How can I serve you today?”

What about you?

I don’t know about you, but I get a lot of emails that try to have me pitch someone else’s products to you. I get a lot of emails that ask me detailed project questions that they’re getting paid to solve. I get a lot of gibberish.

But every now and then I get an email like I did tonight that challenges me.

Sure, I like helping people. But that’s from the comfort of accomplishment, stability, and reputation.

Here, from a position of humility, honesty and failure came a question that shook me.

“How can I serve you today?”

So let me ask you two questions as I end this post.

  1. How can I help you?

  2. How will you react to your next failure?

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