My Biggest Professional Mistakes

Recently I saw Jason Lemkin tweet his answer to “What Has Been Your Biggest Career Mistake?“, and it got me thinking about my own. I’m not quite a decade into my own professional experience, but after seven jobs and numerous positions, promotions, and a layoff I’ve made my share of mistakes. And what’s more fun than baring your soul to the world?

Here are my biggest professional mistakes:

  1. Always thinking I’m right. Like many founders who were employees once, I hate being told what to do or that I should focus on something else. In hindsight, I probably should have listened more carefully to that feedback because it would have saved a lot of heartache and hard conversations that didn’t necessarily have to happen.
  2. Thinking everything would work out when I lost my internal advocate. We all have them in jobs – whether it’s a boss, a potential boss, or even a friend in another department who has the leverage to stick up for you and remove roadblocks from your path. I’ve lost my internal advocate three times (boss moving on mostly) and each time, it was the harbinger of eventually leaving the company. If I could go back, I would’ve moved on as quickly as possible after that happened.
  3. Being too transparent. Transparency is touted, especially these days in the entrepreneurship world, as being a primary good. As a manager though, I wish I had been less transparent with my team about the storm going on all around us. I thought that being transparent would help us get through it better together, but I’ve since learned that really what my old team wanted from me was for me to hold up an umbrella that they could be safe under.
  4. Playing politics. Politics are a killer of companies. I’ve been caught up in them too many times and to my chagrin even tried to use them to my own good. Never again.
  5. Being too willing to move on. This one cuts both ways, because I’ve also been very fortunate to work for some great companies. In hindsight, though, I should have been less impetuous to take a specific gig when another position internally was offered to me. I probably should have stayed at that company and done the new gig, but my arrogance got in the way. So I guess the real lesson is being arrogant and letting professional things get personal.
  6. Not admitting my mistakes sooner. This goes with #1, but along with always thinking I’m right comes a tendency to not admit my mistakes, say sorry, and make amends. Too many bridges burned.

Careers are long and I am sure there will be many many more lessons along the way. My hope is that being aware of your shortcomings, and seeking to learn from them, compounds over time.

2 thoughts on “My Biggest Professional Mistakes

  1. I think it’s admirably that you are publicly admitting these “mistakes” and I’m sure you’ve learned a lot from them. This offers us all a chance to learn something and try to acknowledge our own shortcomings. I totally get the “being too transparent” thing. There is a thin line between being ok transparency wise and just being way too much.

  2. Hi John,
    Great article.
    I think it would do everyone good at taking a step back and taking stock. It’s something i do every so often. I highlight my past errors, what i could have done differently, how could i make it better.
    It makes us grow as people, and if the same happens again then at least we are armed with enough info to punch it in the chops and move on.

    Thanks for sharing this with us John.

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