Lost in Transition


I’m 45. I’m in transition in my career at the same time that all my children are creating their own lives.

Empty Nester

Now that the 5 of the 6 children I’ve been busy raising since I was 19 are graduated, employed, and in charge of their own lives, I am looking at the future wondering what comes next. Their achievements make me feel whimsical and proud, and a little rudderless.

This is occurring at a time when I am wondering what I want to do when I grow up. My career so far has been based on expediency, doing what needed to be done to have enough to support a young family. Now that the children are leaving, I find I don’t need to focus on pay as the number one reason to take a particular job.

Mid-career Crisis?

In April, I quit my sales job. I had good reasons, I suppose. I didn’t have another “real” job lined up when I quit. I’m currently doing freelance work, but it doesn’t really pay the bills. Back in March, I looked out at three months of busy personal life that was going to intersect with high stress and budget requirements at my sales job — and then made the only rational choice: I walked away.

I was sad about it because I really liked the job and the people who were my co-workers. But, a generalized feeling of disconnection from my industry (media / marketing / advertising sales) had begun to settle in to my psyche and I don’t miss it at all. The idea of taking another job in that industry makes my skin crawl.

After 25 years of selling for organizations spanning a variety of industries, I have worked in media sales for the last 7 years. Nice people, but brutal requirements and. Zero celebrating. Antiquated management of sales teams with sales managers operating with an Old School / Mad Men mentality. ( I learned a long time ago to instantly distrust any one who cracks a joke about the film Glenngary Glen Ross or thinks that is a good movie. ) I’ve had my fill of misogynistic managers (they aren’t all men, by the way) who think that grinding people down is the only way to produce results.

The disconnect is that I’m good at selling. Really good. I am trustworthy and genuine, and clients tell me what a breath of fresh air it is to work with someone who values them, and doesn’t try to force them in to a solution they don’t want or can’t afford. However, I find sales managers do not value my human connections as true contributions, and are often frustrated at my seemingly carefree manner when it comes to closing business. I’m in it for the long haul. Almost every sales manager I’ve ever worked for can only see the month in front of them. I recognize their shortsightedness and cognitive dissonance, and while I had moments of loving the work, I find that it didn’t satisfy my need to connect, partner, or create positivity. Because at the end of every day, it’s all about what revenue was produced and I’ve come to see the world in a much more holistic way than that.

The Road Not Traveled?

I wonder if I missed some career calling along the way. Should I have become a teacher or gone in to corporate training? What about all the travel I wanted to do? Should I have gone into the travel industry? When I take a Myers Briggs test, I find that my type is The Coach, and Sales & Marketing is a career fit for me. Other tests show I should be an entrepreneur, but the last few months of “freelance” work has shown me that I get sidetracked by organizing my office or talking with people about business ideas or event planning on the phone and not closing revenue-generating business.

How do I figure out what’s next?

I have been fortunate in my life to have a set of skills and experience that allows me to obtain employment easily. For the first time in my life, I have had time to reflect on my choices and consider what my next career step might be.

What I know is that I keep getting jobs I don’t like because those are the ones I am applying to. I’ve walked down so many dead ends, career-wise. I really want to find that thing I can throw my passion and enthusiasm behind. Where my contributions can be celebrated. Is this too much to ask? The thing I can retire from in 20 years.

Thoughts? I am considering:

  • Sales
  • Teaching
  • Development ( non-profit )
  • Operations
  • Marketing
  • _______________