EPISODE 11: The Answer to Self-Sabotage in your Business
If you’ve been in business long enough, you’ve faced this question:
“Do I stay the course… or am I self-sabotaging?”
In this week’s solo episode of The Experienced Entrepreneur, we unravel one of the most complex challenges seasoned business owners face — knowing when something in your business still has staying power, and when your desire to quit is actually coming from fear, fatigue, or avoidance.
This is not a beginner conversation.
This is a maturity conversation — one that honors both your intuition and your data.
For years, the online business world taught us that ease equals alignment, that discomfort signals misalignment, and that the moment something feels hard we should pivot. But the truth is far more nuanced for entrepreneurs who have been in business 5, 8, 10+ years.
In this episode, we explore:
How to distinguish intuitive guidance from self-sabotage
Not all discomfort is misalignment — some of it is growth.
Not all fear is a sign to stop — sometimes it’s a sign you’re on the edge of something important.
The difference between “bad vibes” and genuine misalignment
Most experienced entrepreneurs are either intuition-led or data-led — but neither alone is enough in your second decade of business.
How intuition + data work together to reveal the truth
We talk through the real interplay between gut instinct, metrics, and emotional maturity… and how blending these two creates the clearest decision-making you’ve ever had.
Why self-sabotage often appears right before a breakthrough
We break down the subtle forms self-sabotage can take — from calling fear “intuition” to reinventing instead of refining.
What staying power feels like inside your body and inside your business
This is the wisdom piece no one teaches: how the work that is still yours will continue to pull you forward even when it’s challenging.
How to avoid burning down something that still belongs to you
You’ll learn the signals of a wobble vs a warning — and how to see your business clearly again.
This episode is for you if:
You’re an established entrepreneur craving clarity in your next chapter
You’ve questioned whether you’re meant to stay or pivot
You’ve felt discomfort and weren’t sure if it meant misalignment or growth
You want to make decisions from wisdom, not fear or exhaustion
You’re ready to rebuild a steadier, more grounded relationship with your business
Listen to Episode 11: The Answer to Self-Sabotage in Your Business Now:
If this episode illuminated something for you — if it helped you see where you’ve been wobbling, or where you’ve been tempted to burn down something that still has staying power — I would love for you to join me for a focus group for my brand new offer The Monday Meeting.
It’s live.
It’s intimate.
It’s waitlist-only.
And it’s designed specifically for long-term entrepreneurs who lived through the unpredictability of 2025 and are craving a steadier, clearer, more grounded way to run their business in 2026.
We’ll talk honestly about what’s been missing from your business, what’s working and what’s not, and what kind of support actually feels nourishing in this season of your entrepreneurial journey.
You’ll also get a first look at how The Monday Meeting is being built for entrepreneurs who aren’t newbies anymore — the ones who are ready for less chaos and more clarity.
Get your personal invite by joining the waitlist.
