While beer-storming (that’s beer-sipping + brainstorming) over the holidays with dear friend and Meet, Plan, Go! rock star Sherry Ott, we discussed the Wall Street Journal’s recent article on Baby Boomers and career breaks—and what a potential movement (literally) may happen if, indeed, Boomers begin breaking.

From that chat was borne my 2014 mission. For the next year, every month, I will write a column about Baby Boomers for the briefcase-to-backpack site.

They’ve kindly published it already, but these days, who doesn’t believe in multi-purposing? So let’s get off our Boomer big butts and get this show on the road!

• Not the greatest generation?

We Boomers are a mystifying bunch. I say “We” because I was born in 1960—toward the end of the Baby Boom (1946 – 1964) and have loved riding the surge that followed. We sprang to life during an era of relative convention and conservatism. Then we boisterously rejected all that and, as lore has it, sold our souls to sex, drugs, and rock & roll.

We still like those things (and, increasingly, Viagra, hearing aids, and legalization). But as history writes our story, there’s often a lingering haze of disappointment about what we accomplished with our passion and promise. After all, we preached peace but have enabled costly wars that drag on for decades. We marched for equality yet bitter human-rights fights rage on. We imagined a world less ruled by The Man, Big Brother, and Uncle Sam—yet fear for our freedoms, privacy, and jobs.

Now we’re 50 – 68 years old. If we still fantasize about running away to Woodstock or San Francisco, we probably lack the means and zeal—or are afraid someone might steal our job. Hell, two-thirds of us (in North America) don’t even use all of our modest vacation allocation. Is that a buzzkill or what!?! A haze of disappointment, indeed.

• Let’s change the world—one (vacation) day at a time

But it’s not too late, right? If you’re reading this—Boomer or not—you’re not dead yet. And the best time to take an extended journey is…anytime! Like, when the stars finally align! When you’ve saved some money! Gotten divorced or widowed! Watched your nest (or nest egg) go empty! Or gotten fired or learned you have just one year to live.

In other words, perhaps there’s no perfect time for anything. Yet somehow we find time to fall in love, get an education, buy and sell homes, raise families, manage careers, and move around. If you hang out on this site, you’re likely thinking about moving around.

So we’ll explore what it means to prioritize long-term travel—and the whys and hows and more. We’ll revive forgotten promises and unfulfilled fantasies. We’ll celebrate trips we’ve taken, probe vital topics, and ask the big questions like…

If we’re afraid to go, how do we face down fear and build up faith?

What’s money got to do with it?

What about options like staycations, couch-surfing, and home exchanges?

How will we redefine retirement?

Can we embark on ambitious adventures while managing a health condition?

Why do we work so hard and long—and how can we escape that blessed curse?

How do we keep hope alive through mini-breaks, vacations, and leisure?

Have we become immobilized by our families, homes, gadgets, and stuff?

What are pros and cons of going solo, with a partner, or the whole famn damily?

Since we might live beyond 100, how do we make a work/life plan for that?

As our travels may suggest, why are less fortunate cultures often happier than U.S.?

Shall we start scheming for a Boomers on BreakAway Summit?

• Up, up, and away…

We’ll check out some stats and facts, and get lost in far-out places like Bequia. We’ll share tips and tales from been there/doing that sources like http://travelpast50.com. And above all, we’ll laugh at ourselves and yet hope to inspire each other to go up, up, and away—whether it’s the adventure of a lifetime, or simply using all our vacation days.

P.S. What do YOU want Big Boom RoadShow to explore? Please add your comment below, or send me a private email through my website. Thanks!