Riffing Off the Past: How Some Boomers Stay Relevant

Jan 18, 2009; Glendale, AZ, USA; NFL on FOX analyst Terry Bradshaw during the trophy presentation following the NFC Championship Game between the Philadelphia Eagles and the Arizona Cardinals at University of Phoenix Stadium. The Cardinals won the game 32-25 to advance to Super Bowl XLIII. Mandatory Credit: Chris Morrison-US PRESSWIRE [Via MerlinFTP Drop]

Mandatory Credit: Chris Morrison-US PRESSWIRE [Via MerlinFTP Drop]

If I were a famous retired pro athlete trying to figure out what to do with the rest of my life, I might consider a career in sportscasting.

I’d have immediate sponsorship interest, and therefore, a viable shot at chapter 2 of an already illustrious career.

I could also have a home life and time to travel, given the fact that sportscasting isn’t exactly a 9-5 job.

We see this all the time within the ranks of the rich and famous.

In fact, some say “once famous, always so.”

America loves underdogs, particularly those who’ve already climbed the mountain and are ready to do it all over again.

But what about a guy who was successful in something that didn’t earn him international fame, notoriety, and thus, cultural relevance?

His commodity value is now relative to what he did, not what he wants to do now that his career is, for all intents and purposes, over.

And people wonder why so many successful older men freak out.

I’ll elaborate…[and offer a few solutions].


The 45 to 64 group that makes up nearly half of all new startups in the country, increasing 19 percent since 1996. The older market has seen the most significant growth over the last 15 years.

But as we all know, starting up a new business isn’t a cakewalk for most.

For one thing, there’s FUNDING.

If you’re not famous, you’re less likely to have sponsors beating down the doors.

Adding fuel to the fire, you got your butt kicked in the downturn and are less willing to risk retirement savings on a new venture that’s by it’s very nature, risky.

The next issue is WORK-LIFE BALANCE.

Rigid schedules, family sacrifices…the realities of doing what you had to do at the beginning of the journey.

If you’re not Terry Bradshaw, you need to know that no one’s doing anything but you – probably 12 hours a day.

This dovetails nicely with the final issue: BOUNDARIES.

You may be good at one thing, but not something else…like managing people.

You could outsource, but that’s not cheap and you still have to oversee the work.


If you’re not already rich and famous, get used to the IRS considering anything you do a hobby.

They’re not dumb.

They know you won’t risk more than you absolutely have to, and that after a certain point you see it as something you enjoy that also helps defray taxes.

This is why they assess a “hobby” tax on successful older people who try to start new businesses and then write off the losses.

No one in their right mind wouldn’t do this since so much money is already being spent trying to make something work.

From personal experience, all I can tell you is this:

1] If you’re not rich and famous and had a career that is still viable, try consulting.

I know lots of retired lawyers who do freelance consulting on the side.

All you need is a cellphone and list of contacts – not a brick and mortar structure filled with expensive equipment and people.

2] If you don’t mind breaking even, or operating at a slight loss, understand that eventually you will have to pay the IRS for your indulgences.

3] If you are rich and famous, do whatever the hell you want.

While you’ll still have to show up once in a while, you’ll still feel relevant.

Just ask Keith Richards.