Meet Your Decision Coach

Bring me a choice you’re struggling with. I’ll help you move forward in one focused conversation, so you can get on with your life.

One conversation with a decision coach.

It doesn’t matter if you’re thinking of buying a houseplant or starting over. Any decision that holds you back is a big one.

When a choice has you all tangled up, you don’t need another course, book, or journaling app. You need a real conversation — with someone who can help you see what matters most and guide you toward a grounded, confident decision.

Book Your Decision Coaching Session

North of Maybe provides a space for you to explore one important decision at a time. Sessions last approximately one hour but we’re not watching the clock. The emphasis is on getting to clarity. Visit my private office in Toronto, or I’ll meet you virtually wherever you are.

What Decision Coaching Solves:

You’re not stuck. You’re stacked.

Making one choice — especially an important one — can feel impossible when it’s actually five decisions tangled together. Logistics layered over emotions. Shoulds tied up with wants. It all starts to blur into something unmanageable. The harder you pull, the tighter it gets. But even the messiest problems can start to make sense once you slow down and tease apart the threads with an objective decision coach.

Some decisions don’t look big from the outside, but they hang heavy. Saying no to someone. Admitting what you really want. Letting go of a plan that made sense five years ago, but doesn’t fit anymore. These are the kinds of choices that hum in the background, taking up mental space. And they’re rarely just about practical stuff. They’re about who you are and where you’re heading next.

By the time we talk, you’ve probably heard a lot of advice. Some good, some less so. But most of it isn’t built around you. And instead of helping, it often just adds more layers to an already crowded head.

That’s where I come in. As a decision coach, I help you get clear on what’s really going on: what you want, what’s getting in the way, and how it all fits into the bigger picture. In one session, we’ll figure out how today’s decision lines up with your short-term needs and your longer-term direction — so you can stop spinning and actually move forward.

David Bester, Decision Coach at North of Maybe.

Meet David Bester, Decision Coach

I’ve had a lot of titles over the years, but “decision coach” feels the most like me. I’m wired to listen closely, ask the right questions, and root hard for people as they
move toward the life they actually want.


Whether you’re weighing a personal project, a career shift, or something that’s just been eating at you quietly for a while, I want to know what’s on your mind – and help you stop it from keeping you up at night.


This isn’t a program or a plan. It’s one real conversation about one decision. No pressure, no endless process. Just forward motion.

David Bester, Decision Coach at North of Maybe.

Meet David Bester, Decision Coach

I’ve had a lot of titles over the years, but “decision coach” feels the most like me. I’m wired to listen closely, ask the right questions, and root hard for people as they move toward the life they actually want.

Whether you’re weighing a personal project, a career shift, or something that’s just been eating at you quietly for a while, I want to know what’s on your mind – and help you stop it from keeping you up at night.

This isn’t a program or a plan. It’s one real conversation about one decision. No pressure, no endless process. Just forward motion.

Decision Coach Client Stories

Better Decisions Blog

Latest from Your Decision Coach

3-Second Decision Tips - Free guide to making clearer choices.
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