How Solopreneurs Can Prep Their Business for Vacation (So It Runs Without You)

I solemnly swear I’ve never worked on a family vacation. Can you honestly say that? I can’t.

From checking emails in Magic Kingdom to recording podcasts at the beach, I've been guilty of putting work before family time, even on vacation. After some not-so-great experiences (including a previous Disney trip that didn't go as planned), I've decided my upcoming Disney vacation with my family will be different.

This time, I'm setting firm boundaries by not bringing my laptop, using devices like Brick to physically prevent me from checking emails in the parks, and setting clear expectations with clients. The truth is, most of us aren't handling truly mission-critical work—the world won't end if we're unreachable for a week. My kids are excited about this trip, and I refuse to be that parent staring at my phone while standing in "the happiest place on earth."

Top Takeaways

• I'm leaving my laptop at home and only bringing an iPad with keyboard for genuine emergencies, making the "pain" of working greater than the "pain" of the emergency itself.
• Using tools like the Brick app and Focus mode lets me physically block myself from checking work communications while at Disney, helping maintain boundaries during family time.
• Setting proper expectations with clients in advance is crucial—I've already notified everyone I'm actively working with that I'll be completely unavailable and explained why.
• Practicing "willful forgetfulness" about work matters helps reduce anxiety—most things that feel urgent aren't truly emergencies, and my business is designed to function if I step away briefly.

Show Notes

• Brick App - App used to block distractions during vacation
• Joe's Audio Notes - For follow-up thoughts after returning from Disney
• Newsletter Signup - To stay updated with the latest content
• Streamlined Feedback - To share how you handle work during vacations

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Streamlined Solopreneur helps solopreneurs decide what to use and what to build, so they can stop spinning their wheels and get their time back.

Each week, Joe Casabona shares one practical idea — a system, tool, or strategy to help you get your time back without having to make another decision, hire employees, or sell your soul to AI.

Looking for a place to start? Take the Solo Systems Starter Quiz. 60 seconds, 8 questions, and I will tell you what system you should build first, and exactly how to build it (so YOU don't need to make another decision). https://streamlined.fm/quiz

Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/