| Was he wacky or eccentric? Did he live here by choice or was the choice foisted on him? Was he rich and didn’t give a $#%& or down and out on his luck? Who was he and why did he live here? I’d ask a few questions… and listen as we sat at the hippie bar (as locals called it).
He was a boomer with a ponytail, maybe 63-64 years old. The tail part of the pony wasn’t at the end of a balding pate, you know, the look of a boomer trying a bit too hard. The ponytail was legit. His name was David.
 David lived in a 450-square-foot cabin on a bay adjacent to the hippie bar. I asked him why. He replied, “I’m living my life backwards.
Sittin’ in the mornin’ sun
I’ll be sittin’ when the evenin’ comes
Watchin’ the ships roll in
Then I watch ’em roll away again
I’m sittin’ on the dock of the bay -Otis Redding
 He wore sandals, was dressed in tattered Patagonia shorts, and wore a t-shirt that said “Smell the horse on this one.” It would be easy to pass judgment and see a man down on his luck. A small cabin, worn clothes and no 9 – 5 gig that I could tell. He wasn’t down on his luck; he was recovering from living a forward life.
He’d graduated college (St. Thomas) and worked in 3 or 4 jobs before settling into a career. The job dictated his life: how to dress, what car to drive, where to live and what type of home to live in. He bought into the plan. It was the way forward, wasn’t it?
He’d sold his home 16 months ago, one of 4 in his career – each larger than the former. He started with 1,500 square feet and ended with a home of 3,500 square feet. It was the way forward, wasn’t it? At age 62 he awoke and asked, why?
 Over the years he’d made money in his job and real estate purchases. With the sale of his final home he’d cleared close to $500,000 (tax free). Now this.
“This” was a 450-square-foot cabin from May – October at the water’s edge. From November through April he travelled. He needed to be needed so he worked odd jobs wherever he landed. His May to October gig was stocking the hippie bar by 10:00 a.m. each morning.
He was living life backwards. He needed less.
David’s idea of a backwards life was to do the things he neglected when he was young, when he was trying to move forward. I asked him what advice, real estate or otherwise, he’d have for younger souls. He rattled off a few ideas:
1. Know that someday you will want to stop working or work less, which will require money. I saved a little along the way and bought homes to live in. The homes I bought provided money long term. Some of it was luck and some of it was because I took the modest risk to buy. The $500,000, after 35 years of owning homes, has helped fund my present lifestyle. I’d tell ‘em to buy a house.
2. Don’t be concerned with what your friends or neighbors have. Define your happiness. You probably need a place to live and a car (I suggested a bicycle) and some clothes. Good enough is good enough. Don’t “try to keep up with the Joneses,” better to fall behind and live life at your pace…with an eye to the future.
3. To the extent possible don’t allow life to be thrust upon you. Pause periodically and think about what is important. Know what is being shaped by ego and appearance and fight that like a bad cold. Live your life…with an eye to the future.
 I’d bumped into David while kayaking. We finished our beers and went our separate ways. I returned to my kayak and he returned to his cabin, maybe to read Thoreau or plan his next backward move.
I hoped I was as successful as David, absent the pony tale. I’m balding.
Thanks for reading,
Michael D. Holloway
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