The top 10 business mistakes I’ve made

This was tough because I had so many errors to choose from

A client read one of my blogs where I 'fessed up to something stupid that I’d done and suggested I create a top 10 list, so here it is. This was an extremely difficult exercise — not because I couldn’t come up with 10 or bare my soul, but because I had so many to choose from!


  1. I once went into business with a guy whom I didn’t trust. It ended badly, cost me a lot of money and caused many sleepless nights. I didn’t listen to the little voice in my head!


  1. This one should’ve gotten me fired. I left a voice mail for a peer, answering a question that he’d asked me. Then, in the same voice mail, I went on a rant about our mutual boss. My colleague only listened to the first part of my message and then passed it along to a distribution list that — wait for it — included our boss! My co-worker called in a panic after realizing what he’d done, just as I was about to enter a meeting with … our boss. Fortunately, my boss accepted my apology (I don’t think he’d actually heard the message, because it was bad)!


  1. I could use this for the next seven, but I’ve too often feared failure and loss of face, causing me to slow down my success. If I could multiply by 10 the number of failures I have, I’d have 50 times more success!


  1. Several times in my career I became emotionally attached to direct reports whom I shouldn’t have supported. Although I don’t often avoid conflict, I’ve let affection for people overshadow their business faults.


  1. For a period, I put my work life ahead of my family. If you asked me, I would’ve said my family was first. If you looked at my behaviors and calendar, you would’ve said I was lying.


  1. During that same period, I had occasions to broaden my experience (e.g., executive peer group invitations, board position offers, personal development opportunities) that I turned down because I was “too busy.” If I’d had a coach to force me to look at my values and think about my career in totality, I wouldn’t have made the same decisions.


  1. Growing up in a home with a strict parent where humility was overvalued, I didn’t learn how to self-advocate until later in my career. As a mentor of mine says, “If you don’t blow your own horn, there ain’t no music!” Somewhere on the spectrum north of Mother Teresa and well south of The Donald might be advisable. It’s not enough (I now say to myself) to do good work. You need to make sure that you accept your success as well as failure.


  1. When I was an executive at Kinko’s, we were a successful company focused on the college and small office/home office (SOHO) crowd, but we wanted to continue our rapid growth. As we started to get large jobs in our stores, I hired an extremely talented sales executive to build out a commercial sales program. But I didn’t think hard enough about the operational challenges of running big commercial jobs in retail environments (a bit like McDonald’s offering filet mignon!). We took corrective action, and many of my colleagues wouldn’t call this a mistake, but I didn’t stop to think through the unintended consequences.


  1. I invested in two companies because I liked the founders, but I didn’t do enough due diligence. As you might imagine, the fact that I’m listing them here means that I didn’t get much of a return. I’d do the math for you, but the formula “zero divided by something” doesn’t seem to compute. Likewise, years ago I owned a couple of shares of Berkshire Hathaway (Class A shares) but sold them in 1995 because Warren Buffett was getting old.


  1. I’ve worked with some brilliantly talented people whom I learned much from, but I only took the time to adequately thank a handful of them.

I think that’ll do!

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