Aug 6, 2026 · 35 min · 9 segments
Gail O'Halloran is a Wayfinder Life Coach and a speaker who helps women move from self-doubt to self-trust — especially when they're standing at a crossroads that matters. She didn't take the obvious…
Gail O'HalloranGuest
Katie WinchenbachHostAnd tell me a little bit more about the Martha Beck Wayfinder philosophy, not only kind of how that helped you, but also now how does that guide how you're coaching the women that you're working with?
Martha Beck helped me learn, which I wasn't aware, about noticing the thoughts that are driving decisions, especially under pressure, especially in a leadership role.
And so I help women rebuild that internal authority that got calibrated away from years of performing and leading.
And I help them make decisions they can actually live with versus decisions the room decides.
Yeah, I think the most practical thing I can offer is that women to start noticing when they're calibrating versus when they're choosing.
Like calibrating has a slight tension to it, but choosing just feels lighter and more natural and more authentic.
It sounds so simple to say out loud, but when you catch yourself saying, I should handle this a certain way, or I have to present this differently, to just pause, just take a breath and ask yourself, why do I think I have to? And more importantly, what am I afraid of if I don't?
It's a simple thing to do, but to really help us get in touch with what's going on inside.
Yeah, because usually underneath it is a fear of being judged or dismissed or seen as difficult.
And once you name that fear and you can say, oh, I am afraid I'm going to be judged or I don't want to be difficult, but then you're not trapped by the thought anymore.
Like then you can choose, okay, well, if I am afraid of being judged, what can I do differently? Yeah.
me? Or how can I get clarity? Or what can I do to make this situation work for me that feels good? And that's honestly, Katie, that's the difference between like reactive leadership and what I like to call a creative response and asking, what do I actually want to do here? And what else is possible? What am I not thinking of that could be done differently?
And tell me a little bit more about the Martha Beck Wayfinder philosophy, not only kind of how that helped you, but also now how does that guide how you're coaching the women that you're working with?
Martha Beck helped me learn, which I wasn't aware, about noticing the thoughts that are driving decisions, especially under pressure, especially in a leadership role.
And so I help women rebuild that internal authority that got calibrated away from years of performing and leading.
And I help them make decisions they can actually live with versus decisions the room decides.
Yeah, I think the most practical thing I can offer is that women to start noticing when they're calibrating versus when they're choosing.
Like calibrating has a slight tension to it, but choosing just feels lighter and more natural and more authentic.
It sounds so simple to say out loud, but when you catch yourself saying, I should handle this a certain way, or I have to present this differently, to just pause, just take a breath and ask yourself, why do I think I have to? And more importantly, what am I afraid of if I don't?
It's a simple thing to do, but to really help us get in touch with what's going on inside.
Yeah, because usually underneath it is a fear of being judged or dismissed or seen as difficult.
And once you name that fear and you can say, oh, I am afraid I'm going to be judged or I don't want to be difficult, but then you're not trapped by the thought anymore.
Like then you can choose, okay, well, if I am afraid of being judged, what can I do differently? Yeah.
me? Or how can I get clarity? Or what can I do to make this situation work for me that feels good? And that's honestly, Katie, that's the difference between like reactive leadership and what I like to call a creative response and asking, what do I actually want to do here? And what else is possible? What am I not thinking of that could be done differently?
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