COACHING IN LESLIEVILLE, TORONTO
Think it through,
on foot.
Walk-and-talk coaching for professionals working through a decision, transition, or thought you just can’t push past.
Leave each session with a clear next step.
HOW IT WORKS
One hour, on foot, in Leslieville.
01
We meet in Leslieville.
Most sessions start outside Pilot Coffee near Queen and Carlaw. If the weather’s bad, we grab a table inside, move to Zoom, meet at my office, or reschedule—your call.
02
We walk and talk for an hour.
You bring whatever’s on your mind. I ask questions, push where it’s useful, and stay quiet where it’s not. Walking helps us think clearly and get our blood flowing.
03
You get actionable clarity.
You’ll leave with a clear next step: a decision made, a draft of an email, a plan for the week, a question to sit with.
HOW WE HELP
A neutral thinking partner, outside of your work, family, and friends.
Stuck in your own head.
A decision that’s been looping for weeks. A conversation you’ve been avoiding. A question you can’t seem to answer alone.
At a career crossroads.
Considering a move, a pivot, or a leap, and want to think it through with someone outside the situation.
Building something of your own.
Founders, freelancers, and side-project people who need a sounding board that isn’t a co-founder, spouse, or friend.
ABOUT ME
Hi, I’m David.
I help people think through hard things, on foot.
I've spent the last fifteen years working with smart people under pressure—first as a lawyer, then in business and coaching. I've learned that most of the time, people don’t need advice. They need a thinking partner who asks the right question at the right moment, and gets out of the way.
My background is in law, business, and coaching, with training in positive psychology and yoga. But what you’re really getting is someone who listens carefully, asks the right questions, and helps you see what you already know.
I live in Leslieville. The walking routes are good!
SESSION OPTIONS
Simple pricing, no paperwork required.
20-Minute Intro Call
Free
An opportunity to hop on a quick call and meet each other. No pitch, no pressure, just a chat to see if we’re a good match.
Most Popular
Single Session
$135
One hour walk-and-talk (or coffee, or Zoom). Good for a specific question or a one-off check-in.
Four-Session Package
$480
Four one-hour sessions. Save $60 vs. booking individually. Best for working through something over a few weeks.
Payment by credit card upon booking. Free cancellation until 24 hours before start time.
FAQ
Common Questions
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We move to a coffee shop, Zoom, my office, or reschedule. You can decide the morning of our session. No rescheduling fees for weather.
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Research has shown that our brains work more thoughtfully and creatively on the move. Plus, it’s healthy. And sometimes it’s hard to carve out an hour to do something just for you, so let’s take double advantage of it.
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Bring a water bottle if you like, and wear whatever you’re already wearing. This is meant to fit into your day, not complicate it.
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Coaching and therapy are different tools. Therapy helps you understand and process. Coaching helps you decide and act. If you're working through grief, trauma, or mental health challenges, therapy is the right call. If you're working through a decision, transition, or stuck point, that's where I can help.
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Yes, and as a lawyer, I take confidentiality seriously. Our walking routes use quieter side streets, and our conversations remain between us.
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I don't accept insurance, and coaching generally isn't covered by health benefits plans. That said, if you're self-employed or have a professional development budget at work, you may be able to expense sessions as a business or development cost. I'm happy to provide a receipt for any session.
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Every session is structured to lead you to an actionable outcome. Some projects have more than one step and need multiple sessions. We can start with one session and then add on as needed, or scope out a full series at the outset. Whatever works for you.
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Yes — and the structure is what makes it work. You bring what's on your mind, we walk and talk it through, and you leave with a clear next step. Most clients are surprised by how much progress an hour can produce when it's focused, uninterrupted, and outside the usual environments where they get stuck.
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If you don’t feel the session was worth your time, I’ll refund it. No forms, no questions. I believe in win-win, so if you’re not happy, I’m not either. We win together.
Book a session.
Reserve your one-hour session now, or scroll down to schedule an intro call.
If you have any questions before booking, please feel free to reach out anytime at david@openairthinking.com
After you book, I’ll send a confirmation with the meeting spot and my mobile number.
I’m looking forward to meeting you!
Or, want to chat first? We can hop on a quick call to see if we’re a good fit.