After a tech windfall: the challenge of what's next

Tom and Leslie hiking in France; traveling is great, but not enough

On our recent hiking vacation in France, with Sherpa  Expeditions, I heard of a transitioning problem that I had never imagined. What if you were one of those brilliant and/or lucky tech folks who got in on the ground floor of a company and, at age 55 or so, exited your job with a pile of money?
  No problema! you might say. No more work for me!
That’s what happened to many of Tom’s friends, who, like him, retired early after the telecommunications bubble burst and had to figure out what to do with the rest of their lives. Some of his colleagues tried creative approaches to their new reality. One retrained as a Cordon Bleu chef and opened a restaurant. Another started a sports software company. Others became property developers or launched new business ventures. Some started over in new careers in different industries such as bioscience or the energy field.  While many of these people have been successful,  for most it has been difficult to capture the excitement and financial success of the work they did in the heady, early times.  For many, especially those with young families, the idea of not working -- even if they are financially secure -- was a non-starter.
What would you do all day?
 Tom, who wasn’t senior enough to leave with piles of money but with enough to stop working, says it hasn’t been quite as difficult for him and his wife Leslie. But it hasn’t exactly been a cruise in LaLa Land either. More  accurately, they’re feeling challenged in finding their way.
Retiring “takes a long time to figure out,” said Leslie, whose bonds with Tom run long and deep.  When Leslie was a teenager, her family moved to the Philippines, but she wanted to finish high school back home in Vancouver. Her parents sent her to live with family friends, and right there in their house, she fell in love with their son Tom.
They spent most of their working lives in Ottawa and a few years after Tom "retired,"  Leslie did, too. Then the couple, who have no children, moved back to Vancouver,  where they had grown up and where both their mothers still live. They’re working to befriend neighbors and reconnect with old high school friends.
 “We’d been gone for 25 years,” said Leslie. “The people that we knew have other lives, other friends. They’ve had  kids…. They’re hockey moms and dads--a circle we’re never going to break into.”
It doesn’t help that the couple loves adventure: they travel about five months a year -- in three-week blocks,  about the amount of  time they can live out of a suitcase.
 When in Vancouver, when they’re not renovating the family cottage -- an adventure that could be featured in a “how not to renovate” show --they “spend a fair bit of time with the two  moms who have a build-up of needs that they save for the couple's return.
"My mom saves all her computer problems," said Leslie. "Tom’s mom just
 loves to go for coffee. We take them to appointments, stuff the other siblings are doing when we’re gone. We pick up the slack. Then we’re anxious to leave again.”
 Sometimes, it's just not very fulfilling.
At one point, Tom and some old tech buddies decided to plunge into a major robotics competition and build an autonomous car. It took almost two years. The team qualified but didn’t make it into the top 10.
And that was that.
Said Leslie, “I think we are going to have to give some more thought to what we want here to establish a life --  or maybe live somewhere else five  months of the year and establish a life there."