Episode 8: Lessons Learned from My $24,000 Automation Mistake

In 2021 I spent $24,000 (almost a full quarter of my revenue at the time in my online business!) on a program to automate my online course enrollment. I ran it for a year, tore the whole thing down, and walked away with four lessons I wish someone had told me before I wrote that check. In this episode I get completely honest about what went wrong, why smart CEOs chase the wrong things too, and the question you should ask before investing in ANY program or system for your business.

In this episode:

• Why most business advice was NOT built for service-based businesses — and the one question you should ask before buying into any program or system

• The moment I realized the $24,000 system was costing me more than money… and what that actually means for your business decisions

• Shiny object syndrome at the CEO level — it doesn’t go away just because you’ve been in business for years (and I have receipts)

• Why knowing when to QUIT something is one of the most important skills you’ll ever build as a CEO

• The $12,000 investment I made in 2026 that I have zero regrets about — and why it’s completely different from the $24,000 mistake

Take Action:

Think about the last big investment you made in your business — a program, a system, a hire, a service you built. Ask yourself honestly: was it designed for a business like mine? Was it worth it, and why? If there’s something you’re still running because you already paid for it even though it isn’t working… decide today whether it’s time to cut it.

Resources from this episode:

• Well Women Business Assessment — free diagnostic tool to find where to focus in your business right now

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