In this episode, Jenna breaks down the hidden identity tax most entrepreneurs are unknowingly paying — and how staying in the wrong environment is silently capping your income, confidence, and expansion. She shares the real reason changing your environment accelerates growth faster than strategy, the power of becoming the smallest fish in the room, and the three identity shifts that took her from 8–10K months to locking in 101K in 24 days.

If you’ve been feeling flat, stuck, or like you’re circling the same level — this episode is your wake-up call.

What You'll Learn:

💡What the “identity tax” is and how it’s quietly draining your revenue

💡Why environment upgrades create faster growth than tactics

💡The power of intentionally becoming the smallest fish in the room

💡What an identity activator is and how to create one immediately

💡The three identity shifts that doubled Jenna’s income

💡Why investing in your environment is non-negotiable for expansion

💡How luxury retreats function as accelerators, not vacations

Key Takeaways:

👉 Staying in environments that reinforce your old identity costs you money, clients, and opportunities.

👉 Growth accelerates when you place yourself in rooms that stretch you — not where you’re the expert.

👉 Identity activators are bold decisions that draw a line between who you were and who you’re becoming.

👉 Keeping prices low isn’t generosity — it’s avoidance of claiming authority.

👉 The question isn’t “Can I afford this?” — it’s “What is staying here costing me?”

👉 The woman who waits stays stuck. The woman who moves collapses timelines.

Episode Timestamps:

[0:00] Walking home in the rain & booking Dubai
[1:30] The identity tax explained
[4:00] Why being the biggest fish keeps you stuck
[7:30] What an identity activator is
[9:30] The three identity shifts that changed everything
[12:00] Why upgrading your environment costs money (and why that’s good)
[13:30] The CEO’s Edge retreat as an identity activator
[16:00] What’s your “Dubai”?

Resources Mentioned:

✨ The Expansion Retreat: 4 days in Crete, Greece to become the version of you your next level requires

✨ 20th – 23rd May 2026

Join the Retreat Waitlist here: https://jennaokeefe.co/the-expansion-retreat

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