Episode 47: When it's Time to Break the Rules

Featuring Lisa Jacobs

Personally, breaking the rules gives us the sweats. But after hearing from solo road traveler Lisa Jacobs, we might be convinced that there’s a time and a place for it: whether it’s personally, professionally, creatively, or romantically.

As you’ll hear, Lisa has been doing solo road travel for a couple of years now. As a former lawyer-turned- traveling content creator, Lisa knows what it’s like to defy the norm. And with pink hair and a large van she’s been traveling in, she already stands out from the crowd. But what I’ve loved about getting to know Lisa is that she’s not just about breaking the rules for the sake of rebellion or power or chaos. She’s in it to learn about herself.

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About Lisa:

Lisa Jacobs is a lawyer, interior designer, and writer who lives and travels full-time in her van Freebird. Lisa hosts vanlife events and creativity workshops across the country. She shares honest, practical solo vanlife advice on her Vacay Vans youtube channel.

In this episode, you’ll hear:

  • A bit about the unexpected former life Lisa’s van held

  • How Lisa made the switch to remote work from her office job

  • Why it’s okay to break the rules or do the unexpected

  • A few stories about Lisa’s experiences dating on the road

  • What “extreme dating” is

  • What Lisa thinks about all of the “rules” around being successful as a digital content creator

  • How The Artist’s Way has changed her life

  • What “morning pages” are

  • Lisa’s advice on why you should write more, plus her favorite writing app

Resources mentioned in this episode:


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Music is by Josh Woodward using a CC by A license.

WOTR podcast cover artwork designed by Dani Opal.

Hailey Hirst