I’m a Boomer, and on the day I was born, Song of Saskatchewan, starring Allan Ladd and Shelly Winters, was playing at Loew’s Cinema in Toronto. That night,  tenor Jussi Bjorling missed his concert at Massey Hall (probably, in fact almost certainly, because he was too drunk to sing). These were the Canadian theatrical highlights in Toronto when Boomers were being born.
Among the many jobs and careers I’ve pursued, acting is the one that has lasted the longest. I got my union card in 1982, more than 30 years ago, and I’ve kept it up ever since, even during the 90s and 00s, when I was far away from the biz in corporate purgatory.
I was a spotlight hog at high school and won drama awards. I went to a college with a good drama program and a state-of-the-art theatre, modeled on Stratford’s (they all were in the 70s). I played some good roles there including Tom in Glass Menagerie by Tennessee Williams, a role just designed for a pompous post-teen. I did a better job as MacDuff in the Scots play, learning how to be still and silent on stage.
I left school without a degree, because I was working at acting jobs in the city, and didn’t see the need to study in the abstract what I was doing in the here-and-now. I did a small part in a terrible Canadian tax shelter film starring Kirk Douglas when he was at a low point in his career. This was (although I didn’t know it at the time) my first round of Six Degrees of Stanley Kubrick (who of course had directed Douglas in Spartacus and Paths of Glory). 
I did an episode of an old chestnut, Family Court. It was live improv TV. They gave you the first line of the scene and the last line and you had to improv the middle. The day it was broadcast, I brought home a girl I fancied for tea. I casually turned on the TV, and the timing proved to be propitious, because I got lucky. I was sold on acting from that day on. It was also the easiest money I had ever made.
A few years later, I found myself in Mexico, out of money and almost out of ideas. I ended up in Cuernavaca, a beautiful holiday town in the hills with a substantial expatriate population, most of them either retired CIA field officers or superannuated socialist veterans of the Spanish Civil War. They used to drink together in the Zocalo. This was fertile ground for an actor on the make.
I got a job with the local Canadian/US expat arts centre. We rented a church hall and made our own stage lights. We had casting calls. We produced about a dozen plays in two years, all starring and put on by the expatriate residents. I put together a one-man Shakespearean show with a girl I knew, a guitarist. I did the spoken bits, about a dozen of them, men and women, funny and dramatic, and she sang Shakespearean songs to her own tunes. Very refined, and actually pretty good. We toured that all over Mexico, playing Universities and getting honourary degrees in return.
By the time I was back in Canada, I had decided to be a struggling actor in Toronto. It turned out I didn’t have to struggle much. Five months in a long-running play, then auditioning for lots of commercials, many of which I got. It got to the point where casting agents were asking for my “type”, but not asking for me. 
I worked on that icon of Canadian TV, a rite of passage for every actor, The Littlest Hobo, playing second banana to a German shepherd. I worked with Keenan Wynn, another degree from Kubrick (Dr Strangelove). I got one US commercial that ran nationally for a year. That’s a BIG payout and I lived off the residuals for that year. When that came to an end, I turned to camera crew stand-in work, a little-known job in movie-making that can earn you a CEO’s salary for just standing around. A recurring role as a policeman in a cop thriller rounded out the fat years.
After a corporate hiatus (when we got married, my wife and I flipped a coin to see who would give up show business and get a real job, and I lost) which lasted 20 years, it became clear to me that I would be a better older white male than most of the older white male actors I was seeing on TV. I dusted off my union card, got an agent and started auditioning again.
Work came quickly. A worldwide Mcdonald’s commercial that kept playing and playing and paying and paying. I’d get cheques for runs in Australia, Thailand, England. My commercial traveled more than I ever did, and I traveled a lot. There is a definite niche for male actors in their 50s and 60s – erectile dysfunction aids, walk-in baths, reverse mortgages, no-medical life insurance, you’ve seen them all.

When I was working 30 years ago, I was described as brash. Now I’m 62 I get creepy roles. A motel manager nastier than Norman Bates, a syphilitic murderer, a shapeshifter in an alternate universe, a sketchy horse trainer, a mad presidential advisor.
The work isn’t steady, a few times a year. But it’s always fun, and I enjoy doing something I know how to do well, like remembering my lines and hitting my marks. I wish life were more like that.