Sometimes, It's OK to Get Lost (In Business And Life)

Rewind to my junior high and high school years and you'll discover that I was largely lost -- caught between the worlds of athletics, computers and parties. I got largely lost again in the early 2000's, caught between careers just when my wife and I were starting a family. At times, I felt overwhelmed during my "lost" years. But here's the lesson -- especially for those who are feeling lost right now: You may actually look back on your lost years as unexpected blessings. Here's why.

Let's start with some context. I'm now in my mid-forties. My wife and I now have two sons in high school, and one in grammar school. One is an athlete and musician; one is a caring, loyal friend to his peers; the third is fiercely independent. All are solid students.

That Was -- And Wasn't -- Me

As I watch my oldest ("the athlete") compete, I deeply respect his hard work and also regret some of the athletic talent I squandered. In my childhood, I had trouble focusing on specific tasks for the long haul. Sports seasons were too long. Classes were too dull. But there were these things called computers... And at times, hacking around on early computers (Atari 800, to be exact) pulled me away from other loves like football, football and football. 

On the one hand, I wish I had my oldest son's work ethic when I was starting my journey in athletic fields. But as I look back now, my lack of focus -- and the constant pull in other directions like computers -- was a blessing. I bounced around and made some great lifelong friends (like my second son), and also developed an independent streak (like my third son). The result was an entrepreneurial spark (working with great people) that has served me well the past couple of decades.

Fact is, I was never lost during those formative years. I just didn't realize that I was in transition -- from running with a football to diving into code. Sounds corny, but the current clarity has helped me to look back on my high school years without being quite so hard on myself anymore. And of course, it helps when you get a few big breaks -- like meeting my future wife the first week of college.

The Lost Years, Part II

I experienced another round of "lost years" in my early 30's. The IT media market -- print magazines -- imploded and I got laid off from Ziff Davis shortly after the Sept. 11 Terror Attacks in 2001. 

I survived by freelancing and by also exiting the industry I loved. (Or was I kicked out of the shrinking club?) Rather than looking for work with IT media -- a market in serious transition -- I took shelter at NYIT, a college in New York that needed help building out web sites and alumni communications.

At the time, I felt lost. Really lost. NYIT was very good to me, but I was at a crossroads -- constantly worried about what I wanted to do "next." I didn't realize that each day, I was actually preparing myself for that next move.

Another Lucky -- Or Timely -- Break

After doing some work together in our Ziff Davis days, Amy Katz and I reconnected during my time at NYIT. We partnered up on a range of content projects for Fortune and other mainstream media giants. For the next few years, I bounced around a bit -- returning to Ziff Davis to build IT conferences, then joining a third-party startup with Amy to focus on the municipal broadband industry.

Somehow, my wife and fast-growing children put up with me -- a media guy who was on a perpetual journey without a clear destination.

Each individual leg of the journey didn't look like much:

  • Launching email, web and digital products at a college.
  • Building business-oriented content for Fortune and others.
  • Moderating CIO and IT events at Ziff.
  • Assisting entrepreneurs with a small, niche community web site.

But wait: Those four bullet points actually snap together into a bigger skill set. I didn't really realize it at the time, but each step in this "lost" journey actually gave me a new skill or capability for my future work with Amy in the IT media market.

Never Lost, But Always On the Move

Like I said: I finally realized I was never really lost during those "lost" year. Each time my career is in transition, I now realize the journey -- rather than the destination -- really is worth enjoying. You just have to convince yourself that it's all going to work out in the end. 

As you face life changes or career changes, I hope you're able to realize you're not lost at all. Just be sure to drop some breadcrumbs along the way. Then, take the time to look back... and see just how far you've come. And definitely be sure to enjoy the small milestones along the way.

Now, go get lost but please be sure to report back on your journey. I'd love to hear about it.

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