Rob, founder of SIDETRAKKED, at home in Chilliwack BC

My name is Rob, and I built SIDETRAKKED to help me, and people like me, make the most of retirement: travelling well, staying healthy and active, and keeping life interesting. It started with wanting to make our own trip planning easier, and grew from there.

I’ve spent thirty years planning long, independent trips with my wife, and for most of that time it meant doing the research myself, one browser tab at a time. Before I retired, I worked in senior logistics and supply chain management with a major western Canadian grocer. Attention to detail wasn’t optional there, and neither was catching the thing about to go wrong before it did. That’s just how I’m wired, and it turns out it’s exactly what a good trip needs too.

I’m not really a beach person. I like seeing things, moving through a place, being active in it. Cross-country trips, new cultures, meeting people who see the world differently than I do: that’s what pulls me back to travel, not sitting still for two weeks.

Building SIDETRAKKED has taken a lot more work than I expected going in, but now that it’s close to finished, I get to use it myself, which was the actual starting point. If it also helps other people plan better trips, and if I earn a little bit of money doing that, I think that’s a good outcome. I like learning, and I like challenging myself, maybe more than I realized until I started this. Going in, I had no real experience building a website, working with AI, or running a business. None of it. That’s one of the better things about being retired: I finally have the time to explore and push my own boundaries, instead of just reading about how other people do it.

Travel is only part of what I care about at this stage of life. I want to live long, and I want to live well, and I’ve come to see those as two different things. Health and finances matter, but the piece I think about more is staying socially connected and capable. I’ve watched what happens when people start losing physical ability, even in small ways. It’s rarely just physical. It brings stress and anxiety with it, and a real change in how someone sees what they’re still able to do.

That’s what SIDETRAKKED is about underneath the travel content: helping people stay active, connected, and mentally engaged as they get older, so they’re capable of doing what they actually want to do, for longer. Learning belongs in that too. Keeping your mind challenged is part of staying capable.

In practice, that means multiple sides to this site. One is the Travel Better side, which includes the travel articles and tools; the Trip Audit, the hands-on planning work I do for people taking on a big, independent trip. The other is the Living Better side: the articles, tools, and considerations regarding health, finance, purpose, and community in this stage of life. In the future, I may include more core pillars within the website. All of this comes from the same place, wanting to live well.

I’m based in the Fraser Valley in British Columbia, so everything here (the costs, the insurance guidance, the flight logistics) is built from a Canadian point of view. I don’t have this all figured out, and I’m not pretending to. But I’ve done the travel, made the mistakes, and I’m doing the work now to build something useful out of it.

If you’re planning a big trip, or just thinking seriously about what the next chapter of your life should actually look like, you’re in the right place.

Travel and retirement: practical, sincere and to the point

An occasional email with planning tools and practical ideas for travelling and living well in retirement.