EPISODE 15: 10 Questions to get your business ready for 2026
Before you rush into goal-setting, optimization, or “what’s next,” there’s something more important to do: integrate the year you just lived.
In this reflective year-end episode of The Experienced Entrepreneur, I guide seasoned business owners through 10 powerful questions designed to help you make sense of 2025 and move into 2026 with more clarity, steadiness, and intention.
This is not a productivity episode.
It’s an integration episode — created for entrepreneurs who have been in business long enough to know that insight doesn’t come from moving faster, but from listening more closely.
Through a series of thoughtful prompts, I invite you to reflect on the ways your business grew beyond revenue, the patterns that repeated themselves throughout the year, and the moments that revealed how much your capacity and maturity have expanded.
You’ll explore:
Where your business quietly grew in resilience, boundaries, and self-trust
Patterns in your metrics, energy, or decision-making that shaped your year
Wobbles you moved through with more steadiness than in past seasons
What you released in 2025 — and how letting go created space for something truer
How aligned your business felt with the life you’re trying to build
What steady growth could look like in 2026
Which parts of your business are asking to be tended to before your next step
How you want decision-making to feel in the year ahead
What kind of rhythms, boundaries, or structures will support the version of you you’re becoming
Which wobble you want to catch earlier next year — and what will help you steady it
I’ll also share an invitation to a live, waitlist-only focus group for The Monday Meeting, a new mentorship space designed for experienced entrepreneurs who want a steadier relationship with their business and clearer signals for navigating the year ahead.
If you’re craving reflection without pressure — and clarity without hustle — this episode offers a grounded place to pause before stepping forward.
Ready to steady your business for 2026?
Join the waitlist for The Monday Meeting and get invited to the private January 6th focus group.
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.
