The Control Freak's Guide to Letting Go (Sort Of)
- Cassie Wilson
- Mar 7
- 2 min read
Me and you. You and me. We’re the type of friend who colour-codes the group chat, creates detailed itineraries, and has everyone's shit memorized. When we’re involved in something, considered it handled (shoutout to Olivia Pope).
I used to pride myself on being the Ultimate Planner™. Need a reservation at that impossible-to-book restaurant? I'm your girl. Group trip coordination? Already made a spreadsheet. Birthday surprises? Check out this Pinterest board.
Signs You're The Always-In-Charge Friend
You've never met a Google Doc you couldn't organize
Your friends literally say "Just tell me when to show up and what to bring"
The thought of someone else booking the Airbnb gives you hives
You have everyone's coffee orders saved in their contact (including their backup choices)
The problem? It's exhausting. And sometimes, just sometimes, you dream about being the friend who just... shows up. But then you remember that one time Amanda was in charge and booked a "beachfront" hotel that was actually a 45-minute walk to the ocean. Never again!
The Art of Strategic Delegation
Start small: Let someone else pick the restaurant. Yes, their taste might be questionable, but you won't die from one mediocre meal.
Create foolproof systems: Share your tried-and-true planning templates. It's like training wheels for your less organized friends!
Work WITH the people: Keep in mind everyone’s strengths and weaknesses when asking for help
What If Everything Goes Wrong?
Sometimes it will. And you know what? Those disasters often make the best stories. There was this one time, me and my girls ended up at this spooky-ass hotel in Detroit (or “inn”, who am I kidding, it was probably an inn). The decor, the staff, everything about the spot felt like we had time travelled to the 1910’s. None of us will EVER forget those shared moments. Ever.
Baby Steps Toward Freedom
Next group dinner? Let someone else handle it *
Create a rotation system for planning duties (with very detailed handover notes, obviously)
Practice saying "Whatever you think is best" without immediately following up with suggestions
Sometimes the best thing you can do is sit back, relax, and watch chaos unfold with a handful of popcorn and a bottle of Perrier.
Can I be a Hypocrite?
For the moments that REALLY matter. The moments that REALLY count. The trips over a thousand dollars. Forget EVERYTHING I just said. Do it all yourself, lol.
*this is kinda toxic, but I usually make a back-up reservation at a nearby restaurant or at the very least, keep a running list of better choices.
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