Mapping New Experience to Past Failures – Extracting the Lessons

A new experience with this piece of armor that can help win future battles.

January 09, 2022

Take this opportunity to reflect.

I am where I am today because I failed.. over and over again. And most importantly, didn't stop. I learned and kept going. I would argue I have failed more than the average person. ?

A big part of that is I tried to do a lot of things in my life I probably had no business doing or was out of my depth. I don't often think about what I ‘should' do. I just dive in with both feet and learn as I go. Sometimes that leads to bad endings. But it never ends without lessons.

But as your life moves along.. years go by.. I think it's healthy to think back and ask tough questions.

Some of these memories may be painful so it's important to enter them from the perspective of the observer; you aren't that person anymore. See that person who did ‘those things' as someone else; an old friend maybe. Don't be invested in the actual outcomes that occurred or dwell on the ‘feelings' you felt.

In other words, don't beat yourself up.

This is an exercise to apply what you know today to understand why you failed and ask:

  1. Where did I go wrong?
  2. What steps could I have taken to get a different result?
  3. What was I missing that I didn't know then but know today?
  4. Any lessons from this analysis you should be sure to apply today?

That 4th point is important. We're doing this to hopefully remind us of our flaws or potentials for failure so we don't repeat the past! Something we could learn in a lot of areas of life, right? 😉

To give you an example of this applied, I'll talk about 2 times in my past where if I'd have made better decisions, I would be in an entirely different place today. But.. I learned.

Matt the Artist

The picture to the right was one of my art shows in the early 1990s.

I didn't know anyone in the business or any opportunity to show art (beyond malls, haha). I planned, organized and put these on myself. You can't see it in this picture (this is my artwork).. but I had a few artist friends that showed there stuff too.

I'd send out flyers, invite everyone I knew. Family and friends attended. This was in the mid-90s.. before the Internet!

I even bought the wood and built the stands you see in the picture! ? ?

And I sold some art!

I did commissioned work over those years as well.

But I never made a living at it. At best, I paid for my materials.. I stretched my own canvas, used acrylic or oils. It was pricey.

I bartended to support myself as a struggling artist.

As I Look Back at Those Days

This was my first business. Launching out into this space when I was 18-19 years old. No formal schooling beyond one class, the one semester I attended college at UW Eau Claire.

I won't get into the whole story, but there are a couple things I did wrong or could have done better.

Self-taught was cool and all (and believe me, I spent years learning my craft.. from books and working on it), but I could have really benefited from getting a degree of some kind in art or at least taking more ‘classes'.

Besides just getting better at my craft, there's another thing that I could have greatly benefited from.

Making contacts and becoming part of a community.

Today I know the power of ‘networking' and knowing people.

That is something I sorely, sorely missed in those days. I met some artists over the 8 or so years I pursued art, but I never really mingled or found myself in the art community as a whole. I was an outsider.. unknown.

School may have helped with my skills, but more importantly, it would have introduced me to people that may have helped tremendously in my career/business. I didn't have a mentor or anyone to really guide me.

So the biggest lesson for me is not the art itself or that I didn't try hard enough. It was that I lived in a bubble and never made any meaningful connections.

Matt the House Painter

Well, maybe why I started a painting and repair business makes more sense now that you know my art background. 🙂

Circa 2001. Not a great picture, but this is one of many painting projects.

I painted a lot of houses (interiors, exteriors), and did a lot of drywall repair.. started MPR Remodeling. Built a 4-5 man team to help me.

It went GREAT that first year.

This time it was different though! I did have a network and knew people. I had sales experience at this point and knew the power of building relationships and ‘getting out there'.

But with my success and still being naive about people, I fell into some really bad partnerships.

I had some good partnerships and work.

But I also had a couple of bad ones.

One, in particular, became a nightmare.

I met this person at a morning breakfast club for businesses. And from what I could tell this person had a good reputation. They were also a contractor with many, many more years of experience than I had.

He was impressed by how quickly I built a team. For some reason, he couldn't retain a team and he had ‘ALL THIS WORK'. We could team up! I had the team.. he had the work. What an amazing partnership!

Lesson one: I should have asked more questions or got to know him better. Why couldn't he keep employees?

Fast forward 4-5 months and…

  • I wasn't paid on projects which put me further and further in debt…
  • He somehow stole my only carpenter to work on his projects.. that I knew nothing about!

I was blindsided and had no experience to deal with it.

That wouldn't be the only bad partnership over the years, but I've thought back on these experiences and there are obvious lessons. The one above is one.

Fully vetting someone before jumping into a relationship. Testing the waters. Not just jumping in with both feet and going nuts.

Contract lessons.. to protect my assets and what I'd built.

I'd have more confidence today and experience to deal with this situation. At the time I was green and was only focused on getting work done and finishing projects – completely missing other details or how to actually run a partnership.

So Many Lessons

The above only scratches the surface of all the lessons running multiple businesses over 3 decades.

Do I have regrets? On the one hand, I do! But I don't regret trying and putting myself out there.

All the experiences, good and bad, make me who I am today.

I wasn't savvy, I was naive.. when I first started in business (due to my upbringing and integrity) I trusted everyone. Why would anyone want to do bad things to me? I wouldn't do it to them!

I learned just how many predators exist in business. On one hand, this has hardened me.. I can be overprotective. But it also has made me a better business person. All those experiences inform me.

Just as my extensive sales training and experience helps me read people .. people selling me don't know I know the techniques they're using on me (it's fun sometimes). My experience in business has given me the tools and insights I need to ‘do better'.

I'm still learning. Always will be. That's why I love hosting ‘The Builders' podcast. I still have so much to learn and love talking with others in different businesses and with different experiences.

It's Your Turn to Think Back Or…

Through today's lens do you have any past experiences you could analyze and learn from? What would you have done differently? Anything you can apply today so you don't repeat those mistakes?

If not, if you are younger and don't have much to learn from, sometimes the only way to have those experiences is to get out there and get your feet wet.

It can be scary. You will fail; you will regret it. Or you may be overconfident (like I've been) and may even think you know enough.

But through all that diversity and those struggles, you'll come out the other end wiser and more prepared for that next great opportunity or business.

Taking risks does build character. And each experience gives you another piece of armor or weapons that can help you win future ‘business' battles.

Matt Levenhagen


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