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220 Pick a Damn Canoe. How to Make Hard Decisions When Every Option Costs Something

with

Dawn Andrews

Show notes

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Show notes

Indecision.

You’ve got one foot in each canoe.

You call it flexibility. You call it being thoughtful. You call it keeping your options open.

And you know exactly how this ends. The canoes drift apart, and you’re in the water anyway.

Here’s what Dawn sees in clients stuck in indecision: it’s rarely a shortage of information. It’s an attempt to keep every possibility alive so you never have to feel the loss that comes with choosing. A real decision closes something: an option, an identity, a relationship, a way you’ve always done business. The hard part isn’t always figuring out what you want. Sometimes it’s accepting what you’re willing to lose to have it.

Dawn tells the story of raising her prices about two and a half times when her roster was full, and the math did not work. The number wasn’t the scary part. What it risked was: the accessible one, the affordable one, the helpful one, the one everybody wanted. She grandfathered in some clients (a few still have versions of those rates 20 years later), drew a line for everyone new, and then hit a legit dry spell. What she walked away with wasn’t a magic price. It was self-trust. She can recalibrate her business on repeat.

Then the flip side: a founder, a longtime senior team member, and a role that outgrew them. She kept her feet in two canoes for years, and the business eventually organized itself around the decision she wouldn’t make. Payroll, roles, leadership capacity, her own time. All of it spent avoiding one uncomfortable loss.

In this episode:

  • Why a good decision isn’t a prophecy, and what you actually need instead
  • What avoiding one hard decision costs you structurally and financially, not just emotionally
  • How to tell a real pivot from second-guessing

The question worth saving:

What do I know now that I didn’t know when I made the decision?
New information, a changed assumption, a different business condition? That’s a pivot, and that’s leadership. Nothing changed except you’re uncomfortable that one door is closing? Don’t re-litigate it.

And a note on exceptions: commitment doesn’t require pretending the past never existed. The challenge isn’t having an exception. It’s having no discernible direction because you refuse to let go of anything.

Try this this week:

Write down the decision you’ve been circling. Finish this sentence: “To have this, I’d have to lose ___.” Say it out loud. Then make your choice.

Want the quick takes and the things Dawn is noticing before they become episodes? Get on the insider list at hellodawn.live/insider

Chapters

00:00 The cost underneath the indecision
01:45
The price raise that was really about identity
05:45
The business that organized itself around one avoided decision
07:50
Pivot or second-guessing?
09:15
Pick a canoe

 “Sometimes leadership isn’t choosing the option with no downside, it’s choosing the downside that you’re willing to own.”

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More about the “She’s that founder” podcast

Welcome to She’s That Founder, the podcast for ambitious women who are ready to stop drowning in decisions and start running their businesses like the confident CEOs they were born to be with the help of AI magic.

I’m your host, Dawn Andrews—executive coach, business strategist, and founder of Free Range Thinking. I’m also a proud female leader, mom, and mentor who believes scaling a business shouldn’t come at the cost of your sanity.

Each week, we dig into the real tools and strategies you need to scale smarter, not harder: faster delegation, systems that won’t collapse if you take a nap, and AI tools that actually lighten your load instead of adding to it.

You’ll hear proven revenue strategies, executive leadership frameworks, and practical tools to build a business that grows without burning you out.

We keep it real here—expect candid conversations, quick hits, and the occasional founder rant. Listener discretion is advised (because we don’t always bleep the swear words).

If you like what you hear, make sure to follow along so you never miss an episode. And before you go, leave us a review—it means the world and helps more women founders step fully into their CEO power.

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