Investing so you don’t get lost — or detoured by financial hitchhikers

By Darren Coleman

Special to the Financial Independence Hub

Investing is like driving a car. Every now and then you feel lost, and need to make sure you’re headed in the right direction:  your destination.

That’s why I wrote the book ‘RECALCULATING – Find Financial Success and Never Feel Lost Again’ which makes use of my years of experience counseling clients about their money and assets.

Indeed, when it comes to directions, a car’s GPS makes things easy if you get lost; it just says ‘recalculating’ and you’re off again, hence the title of the book. So while driving is something we all do, we often encounter obstacles: potholes, detours, flat tires, not to mention unexpected passengers.

Take a couple we’ll call Tim and Janet. They’re nearing 60: he’s a financial executive, and she’s been focused on raising their two children to adulthood; one of them they are helping with a down payment on a house and the other is still in university, and they pay the tuition. What’s more, Janet’s parents are in their mid-80s and their health is starting to fail. So, while this couple is on the cusp of their own retirement, they are still playing Mom and Dad, while also taking care of an elderly Mom and Dad.

And they feel lost.

During my almost 25 years as a professional Financial Advisor and Certified Financial Planner, I often meet people who aren’t where they thought they would be. That’s why they come see me. Some of them are off course and unsure of how to get back. They may be ahead of their plans, behind, or just not sure. Even people who are very successful in their careers are often stressed and much of that comes from a 24/7 financial news cycle that assumes we are more financially savvy than we really are.

Supporting financial hitchhikers

With Tim and Janet, the dilemma concerns ‘financial hitchhikers’ —  passengers they didn’t plan on taking along for the ride on that journey known as financial planning. In this case, their kids aren’t really hitchhikers because they’re already in the car, so let’s call them First Class Passengers and the journey is built around them. Janet’s parents we can call Second Class Passengers who may need temporary assistance.

Along with all that is Tim’s best friend Stephen who wants him to invest in a new business venture. He also wants Tim to advise on key aspects of the business as a favour. Tim is conflicted: he wants to help his friend but can’t spare his cash or his time to help. What should he do?

Financial hitchhikers are people you might encounter who need help to get where they’re going. When this happens, you have to decide to stop and help them, or let them fend for themselves and you continue on your merry way. Sometimes they jump right in front of you and appear out of nowhere, and other times you see them on the horizon from a long way off. In any event, you need a plan to deal with financial hitchhikers before you encounter them. The fact is you can only put so many people in the car and carry so much luggage in the trunk before that vehicle stalls.

These hitchhikers may be going the same way as you, and helping them is only a minor inconvenience. Indeed, helping a loved one can be very rewarding. But if helping them means getting off your own course to the point where your plans are in jeopardy, it is pretty serious stuff.

Know the difference between your financial passengers

For some people, their own financial car broke down and hitchhiking is a temporary solution. With your help, they will get going again and land on their own feet. But for others, hitchhiking is their normal way of getting around and if you don’t slow down to pick them up, they’ll just catch the next car coming down the road. Knowing the difference between these two types of passengers is critical for you!

What did my client Tim do? After reflecting on his relationship with Stephen, he felt more comfortable turning down his request to invest in the new business venture. He realized Stephen would simply move on to another ‘investor,’ as was his pattern. And the two will remain good friends.

The lesson learned here is that you can’t be a passenger in your own life. Know where you want to go, and have a plan to get there. And by all means, stick to it! Stick to it even if you encounter problems on the road, as we all do. This is what the book Recalculating is all about. So take the wheel and happy driving!

Darren Coleman is one of Canada’s most successful investment managers and one of the few who is fully licensed in Canada and the United States. His book ‘RECALCULATING – Find Financial Success and Never Feel Lost Again’ is available on Amazon and at


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