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July 21, 2025 By Barry Bright

Vacation Mai Tais vs Office Calls

Two weeks.

When David Whitwell* asked the question, “Can you go on vacation for two weeks uninterrupted?” I was struck.

Because at that moment, for me and Bright Orange Thread, the honest answer was a resounding no.

A thriving business is one with processes and teams so robust that they can operate independently of you.

This isn’t just about sipping mai tais on a beach (though that’s nice).

It’s about a company operating seamlessly, even when you’re completely disconnected.

It means:

  • Empowered Leaders & Team: Your leaders and individual contributors have the authority and abilities to troubleshoot the unexpected. They can solve problems not explicitly covered by your documented processes.
  • Aligned Problem-Solving: Crucially, their solutions align perfectly with your company’s goals and personality. They “get” how you do things, even when improvising.
  • Reduced Dependency: Your business isn’t a house of cards, where one person’s absence brings everything to a halt. It signifies a robust system, not a single point of failure.

As David put it, “It’s building a system so robust that the CEO’s two-week absence is barely a ripple.”

It means you’ve built a team with shared understanding and the autonomy to act within your established framework.

It means you trust them.

It means they’re capable.

If the thought of a two-week, no-contact vacation sounds like a fantasy (to you or your significant other), it is time to look at your operational foundations.

Reply to this email with your thoughts. I’d love to hear from you.

*David Whitwell is a fractional CFO with 15 years of experience working on numerous executive teams to help them go from good to great

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