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Learning from Failure: Things don’t always work out perfectly…

“We learn wisdom from failure much more than from success. We often discover what will do by finding out what will not do; and probably he who never made a mistake never made a discovery.” ~ Samuel Smiles

I was listening to Alex Blumberg interview Nina Jacobson on the podcast WithoutFail when she mentioned the idea of a failure resume. She said she was inspired by a professor who found that “failures sort of define who you are and what you’ve learned and how you’ve really sort of been impacted in many respects more than your successes do. And that owning those failures and embracing them is sort of a critical component to successful people.”

That professor is Tina Seelig and she’s the ED of the Stanford Technology Ventures Program! She assigned students to write a failure resume so that they will “come to terms with the mistakes they have made along the way and to extract important lessons from them.

She highlights two potential pitfalls we have with failure, either we don’t “come to terms with it” and so our fear of experiencing it again colors all our actions from that point on; or we fail to learn from our mistakes, and make the same mistakes over and over again.

So, in the spirit of going first, here’s my top business failures from the last few years. (I have innumerably more personal failures, but that would make for a LONG blog post.)


I invested 3 years and at least 6 figures of cash into my first attempt at an “online membership site” for small business owners. After creating hundreds of “tools and exercises”, writing about 1000 blog posts, sending just short of 10,000 tweets and all the SEO/promotion tricks I know, it attracted not a single paying customer.

I was later told that “resource libraries” like what I created at EnMast hardly ever work. It was a great education for me in online marketing; but I keep thinking I could have got a couple University degrees for that price!

Lesson Learned: Start small. Only invest in an idea if you can get some early conversion. Also, online businesses face a lot different challenges that offline businesses do not. Just because you know how to run a business in the meat space doesn’t mean you know anything about cyber space.

Key Hire for a client

We do a lot of recruiting for clients, mostly of high level people. The vast majority of those hires work out well, but there’s one that we did this year that was a spectacular failure and it still smarts!

There were lots of early warning signs. For one thing, we didn’t attract as many candidates as we usually do, so we presented just a few candidates. One was much better than the others – to the point where we jumped at him. The client said they would do the background check (something we usually do), and so we didn’t dig deeply into his background.

He turned out to be a cancer in the office, an addict away from the office, and was fired within the first month! I was embarrassed and the client was no better off than when we started.

Lesson Learned: Never skip a step in the process, no matter how big a hurry everyone’s in. The bigger the hire, the longer it’s going to take!

Took on work that I should have turned down

Sometimes I’m meeting with a prospect and they are so excited to work with us that I get caught up in their excitement. We do our best work when we are helping businesses transition from a system where the owner is orchestrating 8 – 15 folks in the office to a team of experts, each responsible for their own department. This prospect was smaller than that. He needed more technical, specific help. But he promised that he had the bandwidth to do the work and I could see how just a little bit of help would make a big difference for his company, so we got started.

But the work didn’t progress – he just didn’t have the support he needed to make the changes we were recommending. After two months we agreed it was a good experiment – but not worth continuing.

Lesson Learned: Stay disciplined. Know what you’re good at and don’t let the prospect’s enthusiasm influence you to do something outside of your area of expertise.

Pivot to Video

Video is what the kids are doing these days (or so I hear). We’ve got a few videos on our site that are getting pretty long in the tooth. (Looking at our YouTube channel we haven’t uploaded anything for 7 years! :–0)

So 2018 was the year I was going big into video. I researched cameras, and lights, I started watching a bunch of YouTuber’s that I respect and who’s work might be inspiring. I made plans, I wrote scripts, I even shot some video! But I didn’t upload anything!

While you have to make something terrible in order to make something great, all I managed to do in 2018 was make some terrible stuff. Nothing made it out the door.

Lesson Learned: It’s easy to get lost in planning. Execution is what leads to success. When the success of a project isn’t tied to success in someone’s job, that project is a lot less likely to get done. It’s simply not that important to anyone.

Now it’s your turn. What are some of your biggest failures? Have you got past them, or do they still haunt you? What’s the lesson you need to learn from each?

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