What if the biggest breakthrough in your leadership journey—or your next bold career move—won’t come from working harder, writing more code, or consulting on a project?

What if it comes from one meeting—an internal one—with every version of you?

Stay with me. Imagine this.

You walk into a boardroom. Every seat is filled by a different version of you. Child-you. Teenage-you. The early-career, eager version. The one who’s burned out. The parent. The version that wore masks to fit in. The one who doubted everything. And then—your future self. The version who’s made it, who’s calm, wise, and deeply grounded.

They’ve all been waiting for you to show up and lead this meeting.

To help you guide that conversation, here are six questions that can change everything—not just personally, but in how you lead, show up at work, and make decisions:

1. What does each of you need to hear right now? Some parts of us need reassurance. Some need permission. Some just want to be acknowledged. Listening deeply is leadership—especially when it’s your own voice.
2. What have I been carrying for too long, and who asked me to carry it in the first place? We often take on expectations, roles, or pressure that was never ours. Letting go might free you up for better choices and clearer boundaries.
3. If I fully trusted this was all going to work out, what would I do next? Let your future self answer this. The one who’s already made the hard decisions and is thriving. They know.
4. Which version of me have I been ignoring—but they hold the key? Sometimes we silence the most honest, courageous part of ourselves. That voice might be exactly what your team—or your life—needs right now.
5. What have I been too afraid to say out loud, because once I do, it changes everything? Naming truth is a catalyst. Whether it’s to yourself, a colleague, or a boardroom, the first person who needs to hear it is you.
6. Are there any beliefs that each version of myself have that are different to now? Why? Have they changed for the better or worse? Have I grown up or grown afraid? What does my future self believe that I currently struggle to?
7. What does the future version of me no longer tolerate—and why am I still tolerating it today? Burnout, toxic meetings, unspoken conflict, outdated beliefs. Whatever it is, future-you has already moved on. Why haven’t you?
8. What message does my future self have for me today as her past self?

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This is the meeting most professionals never schedule—but it might just be the most important one of your career.

So here’s a question for you: If your future self was leading your next strategy session, what would they say you’re overdue to address?

I’d love to hear your thoughts. Have you ever done something like this—personally or professionally? What shifted for you?