Remote Pep Talks with Ryan Millar
Episode: Setting Sail on New Ventures

Episode Summary
Ryan once dismissed sailing as an elitist pastime. But after stepping aboard tall ships at SAIL Amsterdam, he discovered something else entirely: sailing is rebellion, discipline, and freedom all at once. In this episode, Ryan unpacks how the craft of sailing offers powerful lessons for launching new ventures — including his own with Dashwell, a company helping people communicate with clarity, presence, and impact.

What You’ll Learn in This Episode

• Why real freedom is built on discipline, competence, and teamwork.
• How to “put miles beneath the keel” when starting something new.
• What sailing can teach us about leading, adapting, and showing up fully.

Key Quotes

• “Sailing is the ultimate ‘forget convention’ move — it’s freedom earned through skill.”
• “Even in calm waters, you’re always working your ship. Progress never happens on autopilot.”
• “Launching something new means casting off — even if the horizon feels uncertain.”

Your Pep Talk
Whether you’re sitting on an idea, halfway through a project, or ready for a new chapter, this is your invitation: cast off, adjust your sails, and set your course. The discipline and craft you bring will carry you further than you think.

Ryan’s New Venture
This episode is also the beginning of Dashwell — Ryan’s new coaching and training company that blends improvisation, storytelling, and presence to help professionals thrive when it matters most.
👉 Learn more at www.dashwell.org

Credits
Sailboat sounds: Studio Nowhere
Music: Josh “Bone 40”

We're going back into the vault and reissuing some old episodes. Enjoy this one in which Ryan dives into the topic of imposter syndrome, which let's be honest, is probably something you've wrestled with in the past. Hopefully successfully, though it's likely an ongoing battle.

This is not just about turtles, it's about memorization, persistence and meaning making.

Also, here's the poem Turtle, by Kay Ryan

Who would be a turtle who could help it?

A barely mobile hard roll, a four-oared helmet,

she can ill afford the chances she must take

in rowing toward the grasses that she eats.

Her track is graceless, like dragging

a packing-case places, and almost any slope

defeats her modest hopes. Even being practical,

she's often stuck up to the axle on her way

to something edible. With everything optimal,

she skirts the ditch which would convert

her shell into a serving dish. She lives

below luck-level, never imagining some lottery

will change her load of pottery to wings.

Her only levity is patience,

the sport of truly chastened things.

Sometimes events can bum us out, big things out of our control. In that case, let's focus on what we can manage. In this episode, which happens to take place on the sidelines of a community football match, Ryan lays out three things that you can focus on to help you power through.

Ryan talks the importance of finishing work, and to prove the point he shares a rap song he made a few years ago, that actually turned out to be pretty good. Finish your things. Not all of them, of course.

Ryan takes a walk in the woods and discusses the importance of taking steps, both physical and figurative.

Topics covered include podcasting, push-ups, housework and parenting.

A delightful, wide-ranging and in-depth chat with the fascinating and delightful Jillian Vorce of the Jillian Group.

In addition to being an exceptionally good hang, Jillian is a B-Corp consultant, podcaster, and speaker with a heart for sustainability. In this episode we look back at how she started her agency, grew it so rapidly, and how and why she ended up changing directions in her personal and professional life, and what all of that has taught her.

In this episode Ryan sits around the campfire and discusses sticking with projects even during the time when they start to get tricky, and the initial enthusiasm wanes. It's short and sweet with lots of useful reinforcing ideas about the value of sticktoitiveness, which is incidentally a great word.