The right wrong turns

Hi, 

These past couple weeks have been really interesting for me. I keep finding myself picking up books reading 10-15 pages and then setting them down and moving to a different one. Everything has been interesting, but nothing has really made me want to lean in. 

That being said, my browsing brought me to a passage in the Creative Way of Being by Rick Rubin, “Taking wrong turns allows you to see landscapes you wouldn’t otherwise see.” 

I really like this quote, but it got me thinking, are all wrong turns something worth celebrating? 

After a think, I don’t think they are. Let’s dive in. 

Fortunately for all of us, Amy Edmondson wrote a book all on this topic called The Right Kind of Wrong. In the book, she talks about how not all failure is good failure, but there is a specific kind of failure that can lead to new innovations and breakthroughs. 

If the wrong kind of failures interest you, I would read the whole book. What I am focused on today is the right kind of failure. 

Not just the failures that push us to see new landscapes, but the failures that push us to see the landscapes that we need to see. The landscapes that fill in our understanding gaps and help us see the bigger picture. 

So her definition of a good failure is what she calls: Intelligent Failure. 

Intelligent Failures occur in new territory (something new to you) in pursuit of a goal. 

Failure has almost become trite in recent years with startup culture using popular idioms like: Build the plane while flying it, Fail fast, Fail upwards, and many more. 

It is important that we do not let the cliché steal the value of failing from our lives. 

The message of this newsletter is pretty straightforward this week, so I am going to end with a couple of tips on ways you can explore new territory in meaningful ways, a couple of things you can ask yourself when you do fail, then give two examples of failure (one good and one bad), and then call it a day.  

Exploring Tips

My personal favorite way to explore new territory in a way that stretches you is to find projects at work that either are understaffed or are stuck. When I was working at a health care startup early in my career, the head of billing for my department went on maternity leave. The second that she announced her leave, I put time on her calendar to see if I could take over billing in her absence. 

During the 4 months that she was gone, I had the chance to do all the billing for our clients and work with the finance team to make sure that all our accounts were square. The first month I did it, I did the process completely wrong. Like I pulled our CFO into a room to show him my team's billing, and he said that this makes no sense, and walked out. Obviously, it was scary at first, but I fixed it and was able to turn it around to him by the next day. 

Although there was an embarrassing moment, I also got a chance to work alongside a CFO when I was 24 years old. Not to mention 12 months later, I was doing a majority of my financial work for a million dollar company. The confidence wasn’t all the way there, but it started building with that failure. 

The next one is with hobbies. The key is hobbies that there is no necessity for you to be good at. Let’s be honest, we all waste time on Youtube, Instagram, TikTok, or whatever your vice is. I am not telling you to stop doing those things, but maybe start watching content on a hobby that is interesting to you. Watching content about your hobbies is still brain rot, don’t get me wrong, but what those videos do that your mindless videos don’t is that they lean you towards action. This morning I watched 45 minutes of coffee content, then I got up and made coffee and tried to use some of the things that I learned. 

Am I better now than I was before? Not really, but I tried something new, and I put my body and attention into motion. My day was much more productive because of it. 

Tips for how to reflect on failure

The thing about failure is that there are probably a ton of diamonds sitting somewhere in your experiences that you haven’t farmed up because the shame of the experience is blinding you from seeing the yield. 

So here are a couple of questions that help me process failure in a way that helps me harvest the diamonds. 

1. What is the story of this failure? ← this is more than just how much of an ass did you make yourself out to be. What are the catalysts that started me down the road? Where did I get off course? Who could have helped me avoid this? Who did try to help me avoid this? 

2. What are other examples of people doing something similar to me? What did they do? ← you aren’t the first person to feel the way you feel and experience what you have.

3. What did I experience that I wouldn’t have if I hadn’t gone down this path? ← you saw this with the CFO story. 

4. What did I learn? ← super obvious. 

Examples:

Good Example: this week there was big news in the world of the NBA, Dusty May (former head coach of the Michigan Wolverines Basketball team) is leaving college and has accepted a role coaching the Dallas Mavericks. On one of the talking head sports shows, one of the talking heads mentioned that the reason Dusty May was so successful in his short 2 year tenure at Michigan was because he created a culture of failure at practice. 

Why would a culture of failure at practice make a college basketball team better? 

You do not want a player’s first experience with failure to be in the biggest moments. You want them to go through the process of transforming failures into lessons in a controlled environment where they can continue to explore. 

The key is that the culture of failure was still built around exploring unknown territory. I am sure that failing to show up on time, not trying hard enough, or forgetting your shoes were tolerated. 

Bad example: one time, Casey was flying home from a work trip and I picked her up from the airport. I had the bright idea to take a “new way home from the airport.” Trust me, when you are the person picking someone up from a work trip, that is not the time to add 30 minutes to the commute home. 

Wrong kind of new landscapes. 

This is a super big topic, let me know if you want to explore it further with me. I can always do a part II.

Kyle