In this episode, Jenna breaks down the hidden identity tax most entrepreneurs are unknowingly paying — and how staying in the wrong environment is quietly capping your income, confidence, and expansion.
She shares why growth often stalls not because of strategy, but because your identity hasn’t caught up to your ambition. From the power of upgrading your environment, to why becoming the smallest fish in the room collapses timelines, this episode reframes what real expansion actually requires.
If you’ve been doing “all the right things” but still feel stuck, flat, or like you’re circling the same level — this conversation will land deeply.
What You’ll Learn
💡 What the identity tax is — and how it silently drains revenue, confidence, and momentum
💡 Why upgrading your environment creates faster growth than new strategies
💡 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 moved Jenna from steady months to a £101K surge in 24 days
💡 Why keeping yourself “comfortable” is often the most expensive decision you’re making
💡 How luxury retreats function as accelerators, not indulgences
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 often avoidance of fully claiming authority.
👉 The real 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] Recording content in the rain & the spontaneous Dubai decision
[1:30] The identity tax explained
[4:00] Why being the biggest fish keeps you stuck
[7:30] What an identity activator really is
[9:30] The three identity shifts that changed everything
[12:00] Why upgrading your environment costs money (and why that’s a good thing)
[13:30] How luxury rooms collapse time
[16:00] What’s your “Dubai” moment?
Resources Mentioned
✨ The Expansion Retreat
4 days in Crete, Greece designed to help you step fully into the version of you your next level requires.
📅 20th – 23rd May 2026
👉 Join the Retreat Waitlist:
https://jennaokeefe.co/the-expansion-retreat
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