Over the course of my career I have indulged in a rich collection of corkers of mistakes. Like the rest of you ‘orrible lot, I am human, and indeed, to err is to be human.

Mistakes are one thing, but what I think is especially important in the interests of blind-faced redemption is to be able to look back on these mistakes, understand what lessons can be learned, and to learn about the overall journey through your life and career.

So, in the interests of said redemption and sharing, I decided to put together a collection of seven notable mistakes I have experienced in my life. They include:

  1. The Danger of Ego – how ego can sometimes spiral out of control, especially when you are thrust into the limelight for the first time.
  2. The Risks of Shipping Merch – we all love merch, right? Of course we do. The challenge though comes with shipping, and more importantly, making sure it gets there. I discovered this the hard way at XPRIZE, as you will find out.
  3. Not Focusing on Metrics – earlier in my career I was not focused enough on measuring my work and that of my team. Why? Fear. This was a huge mistake: if we don’t measure it, we don’t improve it.
  4. Novel vs. Short Story Authors – ooh, this is a juicy one. I completely screwed up a huge keynote opportunity in front of all my peers. The mistake? Misunderstand the role of being able to craft content for different formats and lengths. This is critical, especially in today’s enormously content-rich environment.
  5. The Feature Suggestion Snafu – many communities have been tempted by the idea of letting your community members suggest product features. Be careful though: it can result in a mishmash of unmet expectations and problems the size of a small city that are difficult to ever fix. Ooof, this one sucked.
  6. The Danger Of Leaderboards – huh? Leaderboards? They seem simple enough surely, Bacon? Well, under the covers there are significant challenges with meritocracy, equality, and the visibility of your broader tent of users. Be sure to tread carefully here.
  7. Knowledge vs. Anxiety – possibly the most critical of these lessons was the role of balancing a thirst for growth with the fear of failure due to anxiety. This came bounding into view shortly before I hung my shingle and started my own business.

So, for each of these, I decided to look back on what happened, why it happened, and share some key lessons that I think will be useful to you lovely people.

This is a very personal story, and at times a little embarrassing to share, so go easy on me. 🙂

Check out the video here (and be sure to share your thoughts, feedback, and your own mistakes in the video comments):

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