SWM (Mature and Corporate) Seeks Free-Wheeling Start-Up for Fun and Profit

I counsel a lot of people who are interested in leaving fairly staid corporate jobs for greener pastures—namely start-ups or small agencies. They fantasize that these new environments will provide all kinds of fresh thinking and ways of doing business and that they themselves will be respected and appreciated as elder statesmen with the gravitas and savoir-faire that are just the thing that was missing.

Well, caveat emptor.

In my experience, it is very tough to make this transition at a late career stage and therefore few are successful at it. You may actually be one of the few and if so I applaud your flexibility. But before you start interviewing in earnest, consider the following questions:

-Have you ever had any entrepreneurial experience? Even if it was within the constraints of your corporate job? Definitely a plus.

-Do you gravitate to casual environments? Start-ups are always casual.

-How important is it for you to have a private workspace?

-Do you feel truly comfortable with Gen Y’s? Do you understand their priorities (hint: they may be at odds with yours)

-Are you good at giving regular, specific feedback, or do you tend to resist doing that?

-How do you feel about being respected as a member of the team, but not necessarily as a more senior person commensurate with your experience?

-Do you truly embrace the concept that good ideas can come from anywhere?

-Do you like the idea of working less conventionally, in terms of hours and location?

And frankly, this is just a start. If you go to work for an organization that has less of a hierarchy and is more open and creative, you will automatically be working with a younger group of people. And this could be a good fit for you, or not—what’s important is to be honest with yourself.