When the Detour Becomes the Main Route
☕ Grab your favorite caffeinated beverage and join us for today’s episode, where we’re going behind the brew of issue #19: When “Under Construction” is an Understatement
What does it actually looks like when your business is “under construction” for real? Not just a cute rebrand season, but the kind where the platform shifts under your feet and the systems you built on suddenly stop cooperating.
In this episode, Bernie and I get into the very specific pain of rebuilding while you’re still delivering, still selling, still trying to act like you’re totally fine… while your brain is quietly running a demolition crew in the background.
We also pull apart that tricky question: is this broken, or is this just growth? And what do you hang onto as non-negotiable so you don’t rebuild the wrong thing.
And yes, we’ve both had a moments where we discovered “if the detour is better, you have to make that the main route” which is annoyingly true, but also kind of relieving if you’re in a season where the best next step isn’t the one you planned.
About your hosts:
Alison Leigh Simmons (The Caffeinated Entrepreneur) is the founder of Lead Smarter Co. She helps established service-based founders clean up their backend, build smart systems, and use AI in a way that actually reduces the day-to-day chaos.
🤝 https://www.linkedin.com/in/alison-leigh-simmons/
Bernie DeSantis (The Man Behind the Mustache) is a virtual event producer and owner of Insignia Training Partners. He helps businesses plan and run high-quality virtual events that feel smooth, professional, and human, without making it a whole stressful production.
🌐 https://insigniatraining.com/
thecaffeinatedentrepreneur.com 