The Biggest Mistake I’ve Made In My Career Is …

Top business leaders and entrepreneurs share their worst "f-up" stories of all time.

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If you’re in business, you will make mistakes — a fact of entrepreneurship that’s unavoidable. Most just hurt. But the best kind are actually beneficial in the long run, even if they come at a high cost. These top business leaders and entrepreneurs have shared the biggest mistake that they’ve made — and how it made them better at what they do. (Responses adapted for length and clarity.)

Tom Eddington, Managing Director at Eddington Advisory

My biggest mistake in business was thinking that working hard alone would bring success. Materially, yes, but I paid a price. Averaging four hours of sleep a night, I lost all cognitive ability and would often spontaneously lose my eyesight for an hour at a time. After four years of being housebound and unable to work starting at the age of 44, I reconstructed my life (and my non-functioning brain) through a series of steps that would ensure I would live — and lead — in a sustainable fashion. 

Kevin Groome, Founder of CampaignDrive by Pica9

My biggest mistake was not focusing soon enough on those things that I was uniquely qualified to do for the company. One of the benefits of being a hands-on founder was that I could respond to opportunities and threats with great speed and agility. But allowing my team to take ownership of certain high priority tasks means I can now focus on our company’s overall growth strategy and not get bogged down in the tasks that I have hired my very capable staff to handle independently or with my minor oversight. 

TaChelle Lawson, Founder and President of FIG Brand Strategy Firm 

I made the mistake of trying to be everything to everyone rather than focusing on my area of expertise. I was a new entrepreneur, determined to grow my business, so I was accepting any and all business. The mistake was two-fold. I did a disservice to the client by not fully understanding their respective industry and needs. But I also hurt my own confidence. I struggled for a while after that, constantly doubting myself, my knowledge and my skill set. Once I accepted the truth, which is that I’m not a generalist, I restructured my business. That decision made me much more efficient, focused, and effective as a leader because it forced me to say “no” when I knew my team and I weren’t the best fit. 

Nima Gardideh, Founder of Pearmill

My biggest mistake was avoiding building social capital in teams, being too focused on hitting goals, and not being conscious of the diverse motivations that team members have for work. We ended up losing many team members and having a low employee retention rate. Over the years, I’ve learned to practice conscious leadership and create an inclusive culture that’s focused on bringing the team together to not only hit the business goals, but to help with the growth of individuals. 

We’ve all got “f*ck up” stories. But the best mistakes are the ones that make us better entrepreneurs, leaders and people. What’s the biggest mistake you’ve made and how did it make you a better leader? Let us know in the comments.

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