As a startup founder, I wore a lot of hats and I made a ton of mistakes. I was a typical first-time, 20-something entrepreneur with tremendous pressure to scale with the team and business.
At night, I found myself awake agonizing over the mistakes I could see myself making — not letting go of ideas that I liked but that weren’t good for the business, not presenting my ideas effectively in group meetings, or not saying no to projects when I was already overwhelmed. However, I found that if I wrote down my mistakes in a bedside journal, I could return to sleep and revisit my mistakes in the daytime.
The journal grew and grew. And when I started hiring a team, I saw my team members make the exact same missteps. At first, I was relieved. I no longer felt like I was the worst contributor, manager, director, or VP! But I also wanted to compile my mistakes and share my perspective with them.
At first, I tried giving new managers and directors my bulleted list. However, that was horribly ineffective. No one wants to be handed a list from their manager of all the ways they’ll inevitably fail!
So instead, I started focusing on telling stories and setting the scenes for these mistakes. I sketched the scenes of all of the mistakes and started weaving them into a story that showed the professional journey that everyone makes from their first day on the job as a fresh grad to leading the company as a C-level executive.
It’s an illustrated story that I’ve been narrating and sharing with other startups and organizations. I presented the story at South by Southwest a few months ago. Since then, it’s been mentioned in the Wall Street Journal, Business Insider, and this morning, I presented a few of the mistakes on the CBS Morning Show.
Originally, this was a fun side project that I enjoyed sharing with other startups and the feedback that I’ve heard is that it should be a book. I’ve just started considering that in earnest. If you want to know where you can get a copy of 100 Mistakes, please bear with me — you’ll need to wait a little bit longer!
And at the end of the journey, I’m just grateful to have been a part of a team that allowed each other to grow and to learn from our mistakes. With a little bit more perspective, I am overwhelmed by how much everyone genuinely wants to do well by others and to create something meaningful together. However, old habits, misplaced exuberance, and role ambiguity sometimes get in the way.
Looking forward to sharing more soon!