"Dilemma": The Defining "D" Word

My career dilemma focuses on two more "D" words: "difference" and "dollars."

I need both. I need to know that I'm making a difference in the world, that my contribution somehow enhances others' lives, because that's what will keep me motivated and driven. And I need to make money doing it, because that's just the reality of our lives, with three more kids headed to college in September, '08.

Most of the jobs I'm looking at now are executive level jobs, and in most cases that satisfies one of my requirements. Most of the executive level jobs I'm looking at (not that they're looking at me...) pay quite well and have a great amount of authority as well as, I'd hope, the opportunity for me to use my team-building and leadership skills. But with the exception of a few executive level positions in nonprofit organizations, I wouldn't be able to say that I make much of a difference in the world or that I better people's lives in those positions.

Plus, I've come to the conclusion that I really have to force myself to think like an executive. I can do it, but usually it doesn't come naturally. I'm a great manager and team leader, but not the best "boss." I have a great amount of empathy for "the worker," and I believe that as a manager my primary responsibility is to support my team. But I'm not great at bossing employees around based on policy, ROI, or "bottom line." In other words, I'm good at team leadership thinking, but not necessarily executive leadership thinking.

And here's another dilemma: most of the products I've designed and developed have been delivered in a technical format -- mostly PC software, but also videos, websites, etc. Only a few of my products have been completely non-technical (a Colorforms-type weather activity, a few educational table-top games, and classroom curricula), but I prefer to work in a less technical environment with less technical media and with less technical people. I'd love, for example, to be a librarian at a neighborhood elementary school, or to work with teens as THEY develop their own media and programs, or to be a mid-wife. I have no passion for technology for the sake of technology -- though I find technology hugely helpful as a tool.

And yet, because I've worked among technologists and designed products that are delivered through technical media, I am often assumed to be far more technically oriented than I actually am.

So back to the "D" words. (I promise, by tomorrow I'll have put the whole silly alphabet thing behind me...) My dilemma is how to find a job that contributes in a positive way to kids' lives, a job that I love and in which I can lead a passionate team, a job that isn't highly technical, and that makes the big bucks. Does such a job exist? I'd even be happy to create it -- if I knew what it was!

In the meantime, I'll continue to field job listings that come to me, insisting that I'm a perfect fit (an insurance agent... yeah right!) or that appeal to part of my passion (education, teaching, kids) but require a strong focus on an area I have no passion for, like this job at Microsoft that I actually applied for today. (Me... considering heading back to Microsoft?!)

I'm in the odd position of having a career focus that is both broad-based (education/media) and niche (activism, youth, non-profit), and perhaps it'd be wise for me to either give something up (the educational technology or the non-profit focus) or gain something (more technical expertise).

The answer often seems to be to start all over again with something completely different -- for example, midwifery -- but that's just not one of my options at this point, with Tom having recently started over again in his career (something which I completely support, by the way). Not if we want to send three more kids to college, pay a mortgage or... oh, say... buy groceries.