Candid and Cathartic

On taking career risk

As anybody who knows me can attest, I’m a conservative investor but extremely aggressive with my career.

From the early days, I’ve taken career risk.

Each job change was a step to something new, almost always taking me out of my comfort zone… and at times, letting me rise to the level of my incompetence.

This is not for everybody, and if you do it, expect people to tell you you’re making a mistake.

‘You’re Nuts’

Such as the time I left my job as a columnist for the San Francisco Chronicle to join TheStreet.com. I was one of the first mainstream “columnists” with a following to take that leap… leaving print for online, back in the days when there were still “deadlines,” when stories were held for publication until the next morning.

This was when newspapers had separate online operations, which were more like the farm team than the A-team.

I loved working at The Chronicle, where I wrote a six-day-a-week business column for 10 years, almost to the day. I bridged the world of pre-and-post creation of the Internet. That was back when you could write almost anything about any company without worrying whether anybody was reading it because nobody was counting “eyeballs.”

It was, without question, the best job I ever had. When I announced I was leaving, the typical response was something along the lines of, “You’re nuts.”

That turned out to be a risk worth taking because it changed the course of my career.

I’m a firm believer that switching things up is the only way to grow. For some people, it’s within an organization. For me, it was going elsewhere.

Notable Blunders

But it wasn’t without a few notable blunders, which I discuss in this interview with my friend and former colleague Enrique Abeyta, who recruited me to what turned out to be one of the worst. To watch or listen, just click on the image above.

When Enrique invited me to do his podcast, I told him that it was only under the condition that I could discuss what went wrong there… and why it didn’t work for me.

As it turns out, it was highly cathartic.

Enrique himself – a Wharton triple major who grew up as far from the Ivy Leagues as you can get – has also taken a lot of career risk… and has been through hell and back in the process. He recently launched his own newsletter company, HX Research.

One day maybe he’ll put in writing the lessons he learned… so others can benefit from his experience.

If nothing else, it’s healing.

Enjoy.

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I can be reached at herb@herbgreenberg.com.