I'd rather regret the things I've done than regret the things I haven't done.

Throughout our working lives, we look forward to the day when our bank account finally has the amount of money the financial planners tell us we need to retire. Years of planning, saving, and thinking about money has finally paid off. But what about the rest of our retirement journey? What kind of planning have you been offered? What have you done on your own to assure that the days, months and years of your adventure takes the shape that you dreamed of? It is easy to say what we’re retiring from, but how many of us know what we’re retiring to?

No one would start off on a sailing journey without having done considerable planning, but so many of us leave the harbour of work and head for the open waters of the rest of our lives without so much as a life jacket! This next stage can be one of frustration, disenchantment, anxiety, depression and ill-health—or it can be mapped out to put in place all the things that will raise the probability of having a wonderful, enriching, enchanting voyage. Which will yours be?

This book started percolating in my head (Rachel) more than five years ago after talking to a friend about his much-awaited retirement. He was excited to take on several long-delayed projects around his home and finally had the time to do it. After completing his objective-based projects, he found the time heavy on his hands. He’d applied to and been refused a job at one big box hardware store for which he was more than qualified, and hired at another, only to find that it was a miserable place to work, and so he left that job. 

We had our conversation about a year after his retirement, when he confessed to me that, the projects completed, and nothing on the horizon, he felt lost and unanchored. Some years later, even though he found some seasonal work he liked well enough, he’s still uncertain about his purpose and direction.

As the conversation evolved, I began to realize that there is so much more to a successful retirement than financial planning, and that almost no one talks about it. I brought this idea to lisa Schmidt, an executive coach, co-member of the Montreal Writer’s Collective and friend, and together, we decided to create a workshop in which exploring and talking about all the aspects of retirement that have little to do with finances was the main goal. 

Our reasoning was based on the idea that designing this aspect of our lives is as important as leaving home, getting married, starting a family, choosing a career or buying a house—ALL the big life events. Further, both lisa and I have lived through the closing of our professional doors and having entered a period of wondering how to find fulfillment in the next chapter of our own lives, could not easily locate resources that would have helped guide our path. We both knew what we were walking away from, but what was less clear is what we were walking towards.

So, we started talking to other folks about it and there was general agreement about the need for a workshop like that, especially with the huge numbers of Baby Boomers, and right behind them, GenXers, heading toward or already in retirement. Need is not sufficient, however, there must be demand. But to have demand, people need to know that such a thing exists. 

The purpose of this book is to start this important conversation.