Maycember Madness: Planning, Pressure, and the Myth of Doing It All

Cowgirls Over Coffee

May doesn’t come with twinkle lights, gifts, or permission to reset and yet it’s one of the most intense months on the calendar. In this unfiltered episode, I sit down with Meg to talk how we’re navigating this high-pressure month when you’re running a business, raising a family, and trying to stay sane in the middle of wind, branding season, and end-of-school-year chaos.

We chat candidly about how the myth of “doing it all” is still showing up in subtle ways, how systems become strategy when your whole life feels over-committed, and why managing your capacity has nothing to do with being less ambitious. This episode is equal parts coaching session, permission slip, and reminder that the goal isn’t to fix everything.

In This Episode

• Why May feels like December without the joy.
• The “net stress analysis” I use to make hard choices (like skipping a big award event).
• How to measure the real cost of saying yes: emotionally, logistically, and energetically.
• The myth of linear priorities and why “family over business” isn’t always a useful frame.
• How systems aren’t just about efficiency, instead they’re your lifeline in seasons of unpredictability.
• Why long-range planning creates margin.
• The difference between working in your life and working on your life.

Favorite Moments

• “If everything is getting done, why am I still overwhelmed?”
• “You’re the COO of your own life. You have departments and you need systems.”
• “Sometimes we live in a myth of overwhelm. And that myth is costing us margin.”
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Let’s Keep the Conversation Going

If you find yourself checking all the boxes and still wondering why you feel maxed out, we’d love to hear what part of this conversation hit home. Screenshot this episode, tag @cowgirlsovercoffee and tell us about it!

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