My 6 Worst Career Moves (And What I Learned)

My 6 Worst Career Moves (And What I Learned)

career mistakesI'm marching toward 20 years in the IT media market. I still spend most of my time looking forward. But sometimes you'll catch me looking back (however briefly) in a bid to learn from my mistakes. Here are six noteworthy career blunders -- and what I learned from them.

My mistakes included...

6. I did it for the money

In 1996 I jumped from InformationWeek to Cheyenne Software -- a backup and recovery company later acquired by CA Inc. I made the move for financial reasons and made some great friends at Cheyenne. But ultimately my heart was in IT media.
  • Outcome: Less than three months after joining Cheyenne I jumped back to CMP Media (InformationWeek's parent at the time).
  • What I learned: Do what you love. Love what you do. But constantly reinvent your skill sets.

5. I assumed I knew a market

In 2000 or so I tried to reinvent a print magazine amid the dot-com implosion. I had ideas for a redesign and a new market position -- heading upstream to serve big integrators.
  • Outcome: The publications' core reader base served small VARs. And the readership was moving online. Too bad I didn't spend enough time listening to those core readers and business owners.
  • What I learned: Fast forward to the present and I spend the bulk of my time listening to readers. Do the same with your customers and you'll be fine.

4. I gave away my ideas

I spent 1992 through about 2004 sharing lots of ideas with lots of people. Some of the ideas were lame. But some were pretty good.
  • Outcome: I really didn't control whether my ideas put real money back in my pocket.
  • What I learned: By 2004, I was working more closely with sales- and business-minded folks. Smart move. By 2007, I was discussing a business venture with Amy Katz, whom I'd known since 1998. Amy understood how to build businesses and assets while I noodled around with some content management systems. We ultimately co-launched Nine Lives Media Inc. Now, we control our own destinies.

3. I tried to beat "the competition"

A lot of people spend a lot of time trying to figure out how to destroy their rivals. I was obsessed with media competition in the 1990s. What were our rivals doing? How should we react?
  • Outcome: I spent too much time focused on competitors and too little time focused on customers, and some of my efforts therefore failed.
  • What I learned: When we launched Nine Lives Media Inc., we didn't really think about entrenched IT media companies. Rather, we were out to (A) define emerging markets or (B) disrupt established markets. If we can't do A or B, we don't do it.

2. I got too busy to travel

At one magazine, I got bogged down running day-to-day operations, managing staff and focusing on production issues. It was a great position and a great team. But I never found the time to look up and see the bigger picture.
  • Outcome: I didn't build my own personal brand in the market.
  • What I learned: Travel as much as you can to the right gatherings. Stay front-and-center in the industry you serve.

1. I ignored my gut instincts

Generally speaking, I usually know when the s*** is about to hit the fan. And I can generally sense when a business is about to tank. But sometimes, we're all guilty of ignoring the warning signs.
  • Outcome: I wound up out of a job once. Alas, I had tried to save a business that I knew couldn't be saved.
  • What I learned: Be loyal to a business -- within reason. Take care of yourself and take care of your family first.
No doubt, I'll be making some stellar mistakes in 2010. Hopefully, none will be career-threatening.
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