Chasing Failure - Doing Hard Things

Writing this article is going to be uncomfortable for me because I am publicly talking about a goal I have for myself with a high risk of failure but also full of learning opportunities.?My hope is that my journey can help someone else along theirs.?

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Early in my career I spent a lot of time working on my job and my craft, but not a lot of time working on me. As a result, I tried my best not to make a mistake, and when I did, I didn’t want anyone to know about it.?I felt that any mistake I made was a direct reflection of my worth as a human being. Have you ever felt that way??Have you ever felt like your mistakes make you a failed person??In my experience having that mindset was difficult to deal with because it’s impossible not to make mistakes.??More importantly it contributed significantly to my lack of growth. I was progressing in my career but slowly.?I wanted to grow but I wasn’t embracing failure enough to reach my potential.?

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My mindset began to change when I attended my first Mind the Product Conference in 2016.?I was a product manager for a mid-market company helping to move their product to the cloud.?I didn’t realize it at the time, but that conference planted the seeds for growth and a complete change in my mindset. For the first time I heard from other product leaders like Ken Norton , Dan Olsen and Martin Eriksson talk about what world class product management looked like. I also heard a lot about imposture syndrome and failure.

Many of the speakers talked about how important failure is for learning. Learning as individual product managers, as product teams and as a company.?Not to avoid failure but to fully embrace it as a prerequisite to doing anything meaningful. After this experience I begin to read more than I ever had before. I realized that I wasn't working hard enough on me. I also wasn't giving myself enough grace for failure. I wanted to consume everything I could about the journey others have been through. What worked, what didn’t and why. Successful people were writing publicly about the mistakes they made so others could be given the opportunity to avoid making the same mistakes. What a gift! We often focus on success, but I’ve found the most valuable lessons are in the failures.?

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This change in mindset helped me make the jump to a startup after spending most of my career working for large enterprise companies.?I had no idea what I was getting into, but I wanted to put my new approach to the test. Startups are VERY different than enterprise companies.?Long story short I got lot of opportunities to make mistakes and learn from them. The lessons were hard, but the learning was abundant.?This further fueled my desire to read, listen and consume information from other people to learn and grow. At that point I started looking for the hardest problems to solve because they represented the biggest opportunities to both grow and have an impact.?This was difficult and scary for me to do!

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After leaving the startup I wanted to double down on this mindset, so I decided to begin doing harder things to increase my learning rate. This led me to training for and completing my first marathon. After finishing my 2nd marathon, I decided to double down again and begin training for my first full Ironman.?The Ironman requires you to swim 2.4 miles, bike 112 miles and run a full 26.2-mile marathon at the end. ?In addition to being a difficult goal I've had a livelong childhood fear of water especially open water that I would have to overcome. I knew I couldn’t do this alone, so I hired a full time Ironman coach to both help me and hold me accountable.?I am in year two of training for Ironman Arizona which takes place in November 2023. I can tell you firsthand that learning how to swim, bike & run long distance has been full of failures. Lots of them!! There has also been a lot of growth. I am not an endurance athlete (more on this in a follow up article).

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As of this year I’ve completed 2 Olympic distance triathlons and I am preparing for my first ? Ironman in Oregon later this month.?Am I scared??You bet but my desire for growth is stronger than my fear of failure.?I am learning so much about myself in this process.?I am learning to push through discomfort, how to deal with my inner critic, discipline, problem solving and rebounding from small failures to name a few. ?The key is learning from each mistake and coming back the next day stronger.?Accepting the fact that failure will happen and being resilient enough to focus on what can be learned and continue moving forward the next day.?I am also learning how valuable it is to share growth experiences with others.

For the rest of the year, I’ve committed to writing about my journey towards Ironman Arizona.?You are more than welcome to come along side me and see the good, the bad and the ugly! There has been a lot of ugly so far let me tell you.?I’ve found that learning with others makes the process much more enjoyable.?We are all learning so why not do it together??Let’s give each other a safe place to try new things regardless of the outcome. Let’s help each other grow.