Bob Cramer's Blog

With the first half in the books, and our halftime now complete, the question on the field is the strategy for finishing the game.  Where do we go from here?  What is the definition of winning?   How do we use our remaining time to not only end victorious, but personally satisfied, financially content, with a legacy good enough to qualify for our own hall of fame?

These are big questions.  All around me, men my age, in their 50’s and who have worked in technology-related fields, are in a period of professional transition, facing a tight economy not to mention even tighter hamstrings.  With non-stop digital and medical advances, we work differently, communicate instantly and hopefully live longer, dishing up intriguing complexity that makes defining our go-forward career path a bit of a head scratcher.

Working for one company for long periods of time is the exception and not the rule.  Changing jobs and careers is more the norm.  While our wives and our bank accounts tell us we are too young or too poor to retire, today’s workplace is not that hospitable to us.  Yes, while this five years and counting tough economy has taught us to be agile, inquisitive and opportunistic, that can only get us so far.

We are in a bit of bind.  People work differently today: 9 to 5 is a relic of the past on par with a three-martini lunch, secretaries and pensions; physical offices may be next.  We are not that comfortable camping out at Starbucks or Panera all day.  It is not good for our nerves, blatters or waistlines.  If we do have an office, we are not that accustomed to going in around 11am and working late into the night like the younger people do.  I’m not saying we can’t do it, but it interferes with our well-established sleep patterns, work-life balance and semi-fragile physiques.

Workplace technology also represents a challenge. We grew up on email, Microsoft Office and Blackberries, and while we may have upgraded to Gmail, an iPad and a LinkedIn profile, most of us remain behind the curve on using Twitter hashtags, integrating Dropbox or Google Drive or, at our lowest moments, connecting to the right wireless printer or successfully orchestrating an online conference (ok, maybe that’s just me).

Dressing for work too is not that easy. Business casual is great but leaves a lot for interpretation.  Should I tuck my shirt in or leave it out?  Is it OK to wear the same pair of khakis more than one day at time, how about three in a row?  Do I wear blue jeans some time or shorts in the summer time?  So many questions that my dear wife paid real money at our school’s recent gala to buy me a wardrobe makeover with a consultant who threatens to spend two hours in my closet or take me on an equivalent shopping spree.  Our fathers never had these problems.

Despite these potential pitfalls, we do have a lot to fall back on: our experience, our contacts and our levelheaded maturity.   After years of economic uncertainty, we are no longer intimidated by the prospects of not having traditional work, and we can use this time and our flexibility to our advantage.  We can multi-task, take on assignments out of sheer interest, volunteer, teach, go back to school, start our own business, become a consultant, read, write, retrain, or go into politics or public service.

Maybe it is time to rip up that AARP card invite, join an association for people not ready to retire, and mobilize, online and off.  As the youngest members of the baby boomer generation, we are tweener: not born with a cell phone permanently attached to our hands but not so far gone that we shouldn’t even bother trying to learn.  We can adjust, adapt and add tangible value to all we do.  We are men in our 50’s and damn proud of it.