ACT III: Don Olson

‘If I can make one person smile a day, I’m happy.’

Don Olson at Slice of Life in Oak Bluffs. - Sam Moore

The Island’s first baby boomers turn 70 this year. Our 65-plus population is growing far faster here on the Island than in the of the rest of the U.S., and by 2030, they will represent nearly a third of our population. So who are these folks, and what do they mean to the Vineyard? Over the coming year, we’ll be taking a closer look at people who are in “Act III” of their lives, and as you’ll see, they’re far from a monolithic group.

If you don’t know Don Olson yet, don’t worry, you will eventually. Don and his wife Joan own the last house on the right on Seaview Avenue as you leave Oak Bluffs heading toward Hart Haven and First Bridge. If you’re a down-Islander, you’ve been by it a million times.

The house is pristine, well-maintained, pleasing to the eye. The rolling lawn reaches from the road down to Farm Pond. A porch, often filled with family members of all ages, runs along the front. An American flag flutters atop a stately pole. You’ll also notice three golf holes dotting the landscape, complete with flags and small greens.

According to at least one Oak Bluffs resident, the house is, in fact, perfect. As Don tells it, “I was at a party for a friend and didn’t know many people. So I started chatting with this woman, talking about one thing or another. Well, when she found out which house was mine she just about flipped: ‘The Perfect House is yours?!’ Then she calls her husband over and introduces me. ‘Honey, this man lives in the Perfect House. This is Mr. Perfect.’ To be honest, it was embarrassing.”

The anecdote captures more than the creativity and skill that have been invested in the house and grounds. It also captures Don’s impulse and ability to turn strangers into friends. He does it every day, and he does it with ease and purpose. A trip to Tony’s Market with Don provides Exhibit A. At the counter, Don offers friendly greetings all around, introduces himself to a new worker, asks a few questions, makes a self-deprecating joke, and heads for the door. By the time we leave, everyone behind the counter is smiling.

“You never know what a person is going through, what they might be dealing with in life. Maybe they just feel alone or that nobody gives a damn about them. So I have a goal: If I can make one person a day smile, I’m happy. Sometimes it’s just noticing them and saying hello. If I can’t get a smile the first day, I’ll keep working on it.”

All of the above speaks to Don’s passions and values. A trompe l’oeil decorator and interior designer by trade, Don puts great and loving care into the house. And while he and Joan — married 52 years — are unquestionably a team, it’s Don who more frequently sneaks away from their home in Natick to spend time on Martha’s Vineyard. Simply put, the Island embodies Don’s most cherished passions and values.

“I first came here in the late ’70s to do some interior work on a guy’s house. I had been in the Navy years earlier, and had seen 60 or 70 ports around the world. But when I walked off the Island Queen, I was blown away by what I saw. First of all, there was an incredible mix of people — white, black, young, old, neat, scruffy. There was a hustle and bustle, people talking and laughing, no one standing apart. Then my client, a very wealthy man, picked me up, and he was driving a real clunker of a car. I was hooked. And I still say that the biggest attraction of Martha’s Vineyard, even more than the natural beauty, is the genuine mix of people. The idea of live and let live. That’s the way it should be.”

Don knows firsthand the feeling of being on the outside looking in. He grew up in a community outside Boston where most families led comfortable lives and most kids belonged to one of the golf clubs. Don and his eight siblings fit neither category. Their house had crude plumbing and cramped quarters. The children’s clothes were hand-me-downs or ill-fitting remnants.

“We all shared bedrooms,” says Don. “I had a room to myself for a while, but it was basically part of the bathroom. We had none of the things other kids had. I knew we were poor. I never once invited a friend to my house.”

Worse were the looks Don received from both peers and adults. He vividly recalls the sting of disapproving stares from several teachers. It angers him to this day. “What could a grownup possibly be thinking to look at a young kid that way? Because I wasn’t all neat and clean, they thought I wouldn’t notice?”

Don’s stint as a caddy at one club only reinforced his disdain for the elite set. The caddies were kept at a distance and beckoned when needed. “Most of those guys treated you like dirt,” recalls Don. “They’d barely look at you. It was Do this and do that. The women were better, but not much.”

On one occasion, when money had been stolen from the men’s locker room, the caddies were questioned aggressively, some of them more than once. “You could actually feel their prejudice,” says Don. “They were accusing us for no reason other than being caddies.” The fact that the culprit turned out to be a member’s son was almost beside the point.

Before his 10th-grade year, Don’s family moved to a more working-class town. Although he fit in better with his classmates, Don had developed an attitude that did not endear him to teachers. “I hated school. I wasn’t a reader, and I didn’t like being told what to do. Being a wiseass was all I could offer. So that’s what I did.” Before his senior year, at the age of 17, Don dropped out of high school and joined the Navy. It was a good move.

“I’d never been away from home. It was a shock. I was still a wiseass, so I spent some time in the brig. But I gradually came around. I learned how to get along with people. When you have 90 guys crammed into the barracks, you better figure out how to deal with each other. The Navy taught me discipline. I still speak my mind and I still have a hell of a temper, but I don’t lash out.”

The experience did not lack for excitement. In February 1962, Don’s ship, the supercarrier U.S.S. Forrestal, was designated to retrieve John Glenn’s Mercury capsule after splashdown in the Atlantic. The crew practiced the procedure for months, but when the capsule overshot its mark, another craft got the job. The experience would come into play in 1969 after Neil Armstrong became the first American astronaut to walk on the moon. Don’s sons’ fascination with the event inspired Don to build a replica capsule the only way he knew how — meaning down to the finest detail. It was so realistic, in fact, that several neighborhood kids refused to enter the small, pitch-black chamber.

Don left the Navy in 1963 with an adjusted attitude and a newly acquired skill — decorative painting. Needing work, he took a factory job at General Motors. “I lasted about 45 minutes,” he recalls. “Are you kiddin’ me? Standing in one place doing the same thing over and over? No thanks.” Other jobs lasted anywhere from 36 hours to a week. Eventually, Don turned to painting.

“I did a house in Dover, a high-end community. The house was included on a tour. Word spread, and next thing I know, people are calling me all the time. It just kept growing.” By then he and Joan had two children. Then came a call from a new client, a man with a large house in Edgartown on Martha’s Vineyard. Don was curious; he drove to Falmouth, then hopped on the Island Queen and into that clunker of a car. Martha’s Vineyard had become part of their lives. After 10 years of renting on the Island, they attended a home auction in 1991. Up for grabs was the last house on the right on Seaview Avenue. It needed some work; Don and Joan knew just the man for the job.

Don’s natural interest in people has never wavered; nor has his contempt for pretension or intolerance in any form. A passionate Boston sports fan, Don tuned in when Boston radio station WEEI changed to an all-sports format in the early ’90s. He didn’t always like what he heard.

Don’s first call to the station was prompted by a radio host’s negative comments about a black fan who was seen on TV talking during the national anthem. Don made the point that a black person in our country might have very different day-to-day experiences, and therefore a different attitude toward the flag, than whites. Many calls have followed, all on the same theme of how to treat people.

But the pleasures, the contentment of their new life superseded all. For Don in particular, Oak Bluffs provided a haven. Here he is truly in his element. So keep your eye out for a guy with silver hair and a warm smile. He’s about 5’ 7” and might be sporting a short-brimmed cap that he wears backwards. You might spot him cruising in a yellow convertible or taking a leisurely stroll to Slice of Life. Or you might see him on the beach, regaling people with a story. He’s 74 going on 50, and he cuts quite a figure. You really can’t miss him. But if you do, he’ll find you sooner or later.

On enjoying life

First of all, I can’t believe how fast it’s gone by. Are you kidding me? Like a blink of an eye. I swear I was just 10 years old. But Joanie and I are very lucky. We found this amazing Island, and we have a home here that our family loves as much as we do. You can see it in their faces. I still enjoy my work but I only do three days at a time. Then it’s back to Natick or Oak Bluffs. Three days. That’s it. I tell my clients, and they understand.

On people

I’ll tell you, I meet a lot of people in my work and other places that I just don’t care for. They’re either full of themselves or they look down on people. They act like junior executives, got it all figured out. In fact, I can tell in 30 seconds if someone is a total jerk or not. It’s the way they talk and the way they look at you. If I don’t like what I’m seeing, I’m gone — I don’t care who it is. If you’re not a decent human being, I’m not wasting my time.

On family

There’s nothing more important. Joanie and I got married in 1964. That’s hard to believe. And you know what? We’re like one person. Really. After all this time, knowing each other so well, you become the same person. We’ve got two sons and three grandsons, and they are a joy. I feel the same about my daughter-in-law; she works with me sometimes. Grandchildren are a gift. You love being around them, watching them grow. You can teach them things; you can joke with them, act crazy, show them wonderful places. I love every minute.


Look, I love my country. I’m proud to be an American. But prejudice is common, and you have to speak out. My parents taught us to respect everyone. My father didn’t care who you were; if he liked you, you were his friend. My mother taught us right from wrong. She’d say, If you do something that’s wrong, you’ll know you’ve done it. It’ll be on your conscience.

On the Red Sox

I go way back with that team. Ted Williams was my hero. One time I skipped school to see an afternoon game, and I actually caught a ball he hit. I met him once at a banquet and heard him speak. Typical me, I went right up to him and asked for his autograph. He signed a ball for me. When I joined the Navy, I gave it to my brother, who promised to take care of it. My first time home, the ball’s gone — they played baseball with it and lost it. I was livid.

On his typical Island day

You know, people at home ask me, “So, what do you do down there?” I say, “If I try to tell you what I do in Oak Bluffs, I’d bore you to death.” Honestly, how can you explain it? I swear, this is the only place I’ve ever seen where you arrive and time just stops. It’s like another world.

But to answer the question, I get up at five every morning and head to the Inkwell. I’m not a big swimmer, but I like to go in and relax and paddle around. After a while the Polar Bears start showing up. I know most of them, so we chat and enjoy the view. I’ll make three or four trips to the Inkwell during the day.

Then, if the family’s around, we might play some golf in the yard. Or just sit around the porch talking. At some point I’ll put in a few hours working on the house or yard. Although I don’t call it work, because I love doing it. Dinner will be a barbecue — which we all enjoy — and usually a walk into town after. At night we’ll play some board games or cards. One game we made up is Low Point, High Point. Very simple. We take turns telling about the best and worst thing that happened to us during the day.