In 2007, my wife and I sold our 2,300-square-foot Ottawa home, opted for the world of self-employment and moved to a smart new condo on a charming small-town harbour an hour east of Toronto. Soon, we learned that we had been so mesmerized by the sparkling waters of Lake Ontario, we had overlooked the perils of living in a space half the size of our single-family house while trying to work from home.

Beware, all fiftysomething baby boomers preparing for retirement: There is a world of enticing downsizing options out there and somewhere there is one that fits your needs. But look beyond the convenience and the view. Think long and hard before you choose, and make sure the choice you make offers ample space to live the life you plan.

Originally, we intended to rent out our condo until we retired, but its magnificent location seduced us to move in while we worked from home as freelance editors and writers.

Our rude awakening came the first Saturday morning in our “dream home.” My wife stepped out to the balcony in her bathrobe to enjoy the activity in the bustling marina. All seemed well with the world until a neighbour shouted from the other side of the courtyard: “Oh, I see you’re just getting up!”

Welcome to life in a 1,165-square-foot condo: There’s often no private space to escape.

That’s not to say you should put off selling the family home, the empty nest that is too large for just the two of you. Maybe there are too many rooms, the yard is too big or you don’t want to bother with maintenance.

Downsizing to a condo could be just what you need. Your monthly fees pay for the upkeep and maintenance of the common areas, and if you head south in the winter, all you need to do is shut the door and go.

But before you decide on whether to downsize, by how much and to where, you need to be brutally honest with yourself. Draw up a list of must-haves, then make sure your selection meets your criteria. For example, if retirement preparation involves self-employment and/or working from home, make sure your new home gives you enough elbow room and privacy.