12/07/2014 08:45 am ET Updated Dec 06, 2017

Old Dog, New Tricks: Three Strategies For Retirement Bliss

I found my bliss leading bicycle tours.

I pedaled up the hill and emerged on a bluff overlooking the Pacific Ocean. Rugged cliffs plunged a hundred feet into the foaming surf. The climb had been exhilarating and I took a deep breath; the air was like scentless perfume. I watched the seabirds swoop and dive; their white forms were etched against a cloudless sky. Farther out fishing boats -- appearing as toys from this distance -- rolled lazily on giant swells. One of my guests rode up and gave me a hug. "Fantastic," Alice said, a wide grin spreading across her tanned face, "thank you so much for bringing me here!"

It was Alice's first taste of the California coast. It was my fourth time leading the tour but I shared her elation. No matter how often I experience the ride it never fails to blow me away. I feel so lucky to have discovered this place and time; to be living my own personal retirement bliss.

It wasn't easy getting here, though. I had to change the way I thought about such cornerstones as wealth, security, success, home and family. I made sacrifices but they were few and now, looking back, seem trivial. Change was hard but it was much better than the alternative -- stagnation. I figured that just because I was an 'old dog' it didn't mean I had to roll over and play dead.

And it all paid off. Life is good. I get to meet interesting people and share my enthusiasm for travel by bike. I make a positive impact on people's lives and that gives me a sense of relevance, something I had missed since I retired as the head of a marketing firm a few years ago.

I began wrestling with the idea of retirement in my late 50s. Sure, I was looking forward to the freedom it would provide but with my kids grown and no job to go to I was worried about becoming isolated. Plus, how would I find meaning in the empty hours? I had fretted over those and a hundred other thorny questions to the point that I almost dreaded retirement.

My situation was not unique. Millions of baby boomers still struggle with a common dilemma every day; how do I stay relevant in a culture obsessed with youth? For me the answer was to reinvent myself. If you're a baby boomer the concept is not new. Our generation has experienced many social upheavals; from the Vietnam War to the Internet and through each economic downturn and uptick, we've changed and adapted to keep from being left behind. And now our generation faces another unique challenge.

Many of us boomers are still strong, healthy and physically active far into our 60s and beyond. When we reach retirement age and either choose to leave -- or are forced out of -- the job market, we're too often left with decades of potentially productive life and little or nothing to do.

So what do you do if you're near or have reached retirement age and are unsure about how to navigate these new waters? You're ready to cast off the old workaday world but you don't want to trade it for the couch and TV. Here are three strategies that worked for me and I hope will help you adapt and remain relevant during your 'retirement' years.

1. If it's not fun, why do it?
Before I decided to apply for a bicycle-guide position, I spent more than a year riding my bicycle around the world. I wanted to make sure it was really what I wanted to do. I imposed no limit on this research phase. I was prepared to spend as much time as necessary.

2. Don't let your ego get in the way
My bicycle-guide mentor was half my age and at times I found it hard to defer. I just kept reminding myself that he really did know more about the activity than I did. I kept my eye on the prize and put any temporary loss of face in perspective.

3. Let go
Finding your retirement bliss will probably require that you get rid of some (or all?) of your stuff. This might be the hardest part but it opens you up to a whole new world of possibilities. Rule of Thumb: If you have more than two keys, you have too much stuff.

It's important to recognize that retirement need not be the end of a relevant life. The possibilities really are endless; just focus on something you love, don't let pride sabotage your chances for success and let go of the past. Embrace change and the odds are good that you too will find your own personal retirement bliss.

Darby Roach is a writer and professional bicycle-touring guide. He recently rode his bicycle around the world and has written two new books about the odyssey, Right Lane Ends and How To Ride A Bicycle 'Round The World.

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