Sept. 8, 2025

Permission to Thrive and to Redefine Your Midlife, with Dr. Wendy O'Connor

Permission to Thrive and to Redefine Your Midlife, with Dr. Wendy O'Connor

(Episode 48) Ever find yourself asking, “Is this really it?” You’re not alone—and you’re not stuck. In this empowering episode of Mind Your Midlife, Cheryl Fischer sits down with Dr. Wendy O’Connor, a Stanford-trained positive psychologist and success coach, to talk about what it truly means to thrive as women over 40. We dig into the difference between success and happiness, how to stop living by everyone else’s “shoulds,” and why giving yourself permission to thrive may be the most importan...

(Episode 48) Ever find yourself asking, “Is this really it?” You’re not alone—and you’re not stuck.

In this empowering episode of Mind Your Midlife, Cheryl Fischer sits down with Dr. Wendy O’Connor, a Stanford-trained positive psychologist and success coach, to talk about what it truly means to thrive as women over 40. We dig into the difference between success and happiness, how to stop living by everyone else’s “shoulds,” and why giving yourself permission to thrive may be the most important self care decision you make in midlife.

Dr. Wendy brings deep insight into why so many midlife women feel unfulfilled even after achieving all the traditional milestones—and how to finally shift your mindset so you can live with confidence, joy, and meaning.

BY THE TIME YOU FINISH LISTENING, YOU’LL DISCOVER:

✔ Why success and happiness are not the same—and why both matter for midlife women
 ✔ How “shoulds” and old roadmaps keep women over 40 and 50 stuck in self-doubt
 ✔ The mindset shift that helps you give yourself permission to thrive without guilt
 ✔ How to move through regret and create your next chapter with clarity and self confidence

🎯 OMG Moment: Happiness is not a luxury—it’s a foundation. Giving yourself permission to redefine your life now is the next step to creating the life you really want.

Take Action

Notice the “nudge.” That little voice inside that asks, Is this really it? or Could life feel better than this? Instead of ignoring it, honor it. That’s your intuition guiding you toward your next chapter.

Connect with Dr. Wendy at drwendyoconnor.com or on Instagram.

Listen to the 'second act' episode with Shannon Russell (episode 32).

Why This Episode Matters

For too long, midlife women have followed a script of “success” that doesn’t always bring fulfillment. This episode is your reminder that midlife is not a crisis—it’s your chance to redefine success, reclaim joy, and create a life that feels meaningful to YOU.

🎧 Hit follow now so you don’t miss a thing!

 

 

Text me to ask a question - I'll answer on the podcast!

Support the show

🌸 Liked this episode? Share it with fellow midlife women over 40 navigating hormone balance, an empty nest, and self-confidence!

🫶 Love this show? Leave a review to help more women over 50 find us.

💡Want support through menopause, mindset shifts, or midlife transitions?

Let’s talk self-care, self-talk, and owning your next chapter—without the “midlife crisis” narrative.

Connect with Cheryl: Instagram | LinkedIn | Website

00:00 - Permission to Thrive Introduction

01:15 - Challenging Conventional Success Definitions

04:32 - Happiness vs. Success: Breaking False Dichotomies

08:57 - Giving Yourself Permission to Want More

12:03 - Confronting What-Ifs and Fear

16:16 - Designing Your Next Chapter

WEBVTT

00:00:01.060 --> 00:00:19.966
If I say the phrase permission to thrive to you, I wonder what comes to mind, because when I work with clients on mindset, we're digging into what's all that stuff we're telling ourselves inside our head.

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A lot of it tends to be messages that absolutely are not permission to thrive.

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It's self-criticism, it's worries, it's what ifs, and that's what we want to talk about today.

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You get permission to thrive.

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Let's talk about it.

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Welcome to Mind your Midlife, your go-to resource for confidence and success.

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One thought at a time.

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Unlike most advice out there, we believe that simply telling you to believe in yourself or change your habits isn't enough to wake up excited about life or feel truly confident in your body.

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Each week, you'll gain actionable strategies and oh my goodness powerful insights to stop feeling stuck and start loving your midlife.

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This is the Mind your Midlife podcast.

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Our brains are wired to keep us safe.

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I feel like I've said that sentence so many times.

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I should have a dollar for every time I say that sentence.

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Our brains are wired to keep us safe, and that's a good thing, and yet in our everyday lives, we're not facing danger typically as if we were running from a wild animal or something like that.

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We've learned not to touch the hot stove and to look both ways when crossing the street, and we're handling those dangers, but we're not facing overarching danger, and yet our brains and our nervous systems are wired to keep us safe from dangers like that.

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So sometimes we do what maybe I'm going to call an over safety.

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We make ourselves smaller to keep even more safe from things that feel like a challenge.

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And so today, my guest, dr Wendy O'Connor, and I are going to be talking about giving yourself permission to thrive, and we have to then also talk about what in the world does that mean?

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What does success mean?

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What does happiness mean?

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Are they the same thing?

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How do you decide?

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Is it what somebody told you to do, is it not?

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That's a lot of stuff.

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So Dr Wendy O'Connor is joining me.

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As I said, she is a Stanford trained positive psychologist and success coach.

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She helps women exactly as we would love to do design meaningful, intentional and fulfilling lives.

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So let's chat.

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Welcome, wendy.

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Thanks for joining me.

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Defining what success means, I know, is a powerful topic for you, so let's talk about why it is that we each need to decide that for ourselves.

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I went through a period of time where I realized I had checked all the boxes.

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Everything on paper looked exactly how we would typically define success.

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You should go to school, then you should go to college, then you should get a job, a good job, a secure job, then you should get married and buy a house.

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Yet why am I not happy?

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So defining your own terms of what success and happiness mean to you are pivotal to you feeling successful and happy.

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Yeah, it's such a good point and if I'm hearing you correctly, it's not that you're saying I regret going to grad school.

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You're saying I want to make my own decision and do my thing because I want to do it.

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Is that fair?

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So once you're in a situation and you wake up to the reality that what life feels like isn't how life looks and there's a discrepancy that we could heal or up, level or change, there's a discrepancy that we could heal or up, level or change, that's when it becomes our responsibility, then, to take ownership over that and to make some changes.

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But when I realized, oh, I'm not happy because I'm just following a roadmap that's more prescribed and not mine by design, that's the answer, and so then I make decisions appropriately at the time.

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We have a moment to sit and think and we go oh why?

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Did.

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I do that thing 10 years ago, and if we get stuck in that it becomes a problem.

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Yeah.

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The biggest sources of regret are what are women regretting?

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A lot of times it's revolving around kids, because at this point in life our kids are leaving, as they should be.

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That's healthy and good, and that's also really hard and emotional, and we're losing control, if you will.

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I don't know how much control we had even in high school ages, but that feels like a lot.

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And so there's.

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I don't know why I didn't do this.

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Why are they not wanting to be around me?

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It just, I mean, could be a million things related to that.

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Maybe I made bad decisions when they were growing up, just questioning, questioning, questioning.

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And then the other thing is, I think, whether you've had kids or not, when retirement starts to be a little bit closer and it seems a little bit more real and it's not like 20 years down the road, it's kind of like we look at our career path and go, huh, like what'd I do that for?

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I gotcha.

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Yeah, I think it's a really it is an interesting conversation, because the life that we want to live is a life without regret.

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We want a life that reflects what we value, where we derive meaning, what makes us truly fulfilled, so we can be our best for others as well.

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Yeah, and to your point, if we're realizing it now, then okay, let's shift it now.

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Like, don't worry about that, we didn't realize it before.

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Right, correct, correct, okay, excellent, excellent framing of the issue.

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I also heard you say in there a couple of shoulds, and so I think when we're talking about success, that's probably always going to come up, because to me the should is like what does I don't know who I'm looking at, but what does the world say would be success for a woman with my education, or whatever, whatever.

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And that's, it's still a should, right?

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What I believe is a more beneficial, powerful question to ask ourselves is what do I want to be doing?

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And the shoulds really just get woven in there because, again, we're following these conditioned roadmaps, assuming there's a right way to go through life, and so when there is in our minds a right way, then the question is the should.

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There's a right way.

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But the question that's more powerful and leads you to more fulfillment is how do I want life to feel next and what do I most want?

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And that's where we start taking into account happiness in addition to just what is the definition of success.

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I mean in my personal and professional life, which are woven deeply together.

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I won't feel successful if I'm not enjoying this, if I'm not enjoying what I'm creating, how I'm living in my business, how I'm supporting my clients, if I'm not happy, that's not success to me.

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Because, we are conditioned to follow this path towards success.

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That's what you need.

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That's why there's such a disconnect.

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I want and this is the way I look at success.

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The byproduct gets to be success, Right, and that's not the way we've been taught.

00:12:42.389 --> 00:12:42.929
You're right.

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Success, I think, has been probably taught to most of us, as, as you said, milestones or labels or you know achievements that you need to check off, and happiness is like a touchy, feely thing that you can do on the weekend.

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That's exactly why we wake up one day going this is as good as it gets.

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The more beauty, the more abundance, the more gets to appear in our lives as a result of living that way.

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And so I'm not even sure what my question is.

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Just tell us more about what happens when we talk about this permission to thrive idea and when women don't give themselves that permission.

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And so permission to thrive, permission to be happy, permission to be your best lit up self has to start with what you are even going to allow yourself to consider in front of you what's happened in the past, what they've been taught, what they have believed, what they've been shown, what people are doing around them, instead of taking these moments of transition in life or moments of growth or different chapters or seasons in life to simply ask themselves what am I wanting, what am I longing for, what am I wishing for?

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That's what you need to know.

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00:16:50.945 --> 00:16:55.811
You know, as you were saying that, I was just sort of realizing that.

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I wonder if it's also because maybe deep down somewhere we're thinking that if we're trying to be happy then we're taking away from someone else's happiness that we care about.

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It's like a zero sum game thing, like how can we be trying to be happy?

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We're supposed to be making sure our families are happy.

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I just wonder if we feel like we're kind of taking away from someone else sometimes too.

00:17:26.316 --> 00:17:26.938
I don't know.

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We've got a lot of nurturing tendencies within us.

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I will tell you from firsthand my own experience.

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I'm a different mom.

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That's not it.

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Who, by the way, no one else is doing that for you, but you yes.

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And so, looking at happiness and I strongly encourage my clients and women in general to look at happiness as not a luxury, it's a non-negotiable, it's a building block, it's foundational.

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If those parts of us are not tended to, not nurtured, not cared for, we will not be showing up as our best selves for other people.

00:19:23.972 --> 00:19:34.787
And honestly, I think that the most the fear isn't so much that we're going to truly become these selfish witches of humans Right, I think the fear is that, more often than not, women aren't in touch with what truly makes them happy, and doing that work is not appealing, not exciting and not in the comfort zone that we primarily live in.

00:20:03.971 --> 00:20:14.413
Yeah, I think you've hit something, because we can say, oh, maybe it's selfish to take care of ourselves and not take care of other people, and that's not even what we're saying.

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Still, you can take care of other people.

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But that's the surface level.

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I think you might have hit on something very interesting there.

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The deeper level and this is what I end up coaching people on a lot is really deep, deep, deep in our heads.

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What do we really think that we could maybe do and what are we willing to try, with maybe the risk that we won't like it or we won't be able to do it as well as we had hoped, or it won't work out like?

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We think that sometimes those things are really scary, and maybe that is underlying a lot of this.

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There's a big fear of failing, and there's a big fear for a lot of women of having chosen the wrong choice, and so that can be a big factor in how we make decisions.

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To do it, you need to believe that you can handle it.

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Comfortable, you need to believe it's worth trying, it's worth fighting for it's worth it.

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I should be able to believe that it's mine already, and we hear about this.

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Your brain hasn't contemplated this before.

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But what you do need to believe is that you're willing to try and that if you were to achieve it, it would be worth it, and you're going to get uncomfortable and you're okay with having your own back.

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I think it's worth it.

00:22:43.064 --> 00:23:02.997
So it reminds me of a coach that I once was talking to years and years ago, who was saying that one thing that she asks her clients sometimes to do is figure out, okay, what would the worst case scenario be, what's the worst thing that could happen when you start this or go for this or whatever?

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And I was like, really Like, should we be focusing on the worst thing?

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But the point was, if that worst thing happened, you'd be okay.

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The point was, if that worst thing happened, you'd be okay.

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Right, like, how would you handle it?

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Let's talk about it, would you be okay?

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And 99% of the time, yes, I would be okay.

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So then, all right, let's do it, we can figure it out.

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So I call the what ifs the cliff.

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What if it doesn't work?

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What if it goes this way?

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What answer it get to the conclusion that you're most afraid of.

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Is fear, and so you're letting fear make a decision.

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What if?

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Fill in the blank, finish the sentence.

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How significant of a drop is that really?

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So this is something that has been such a game changer for my clients is realizing that they're not looking over the edge.

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Right, but if we really let ourselves be paralyzed by what if we'd never leave the house?

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What if I run over somebody?

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We wouldn't leave.

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Answer your own questions, look at the likelihood of any of those things actually happening, create a reality around that possibility, but don't let fear make your decisions for you without letting yourself feel more informed by looking over that edge.

00:25:19.550 --> 00:25:32.962
Such a great point and, and I would add to that, I can see that this is something I mean you're a coach, I'm a coach that is worthwhile for someone to do with a coach, because when we start down the what if?

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Path, then a coach is going to help us to maybe not get so stuck in that that we're like now everything is terrible and I'm telling myself I'm an idiot all the time, which is the way the brain sometimes goes.

00:25:46.613 --> 00:25:55.931
But, yeah, very powerful to realize that we can handle what comes and it's going to be okay, agreed, Okay.

00:25:55.931 --> 00:26:05.280
So now that I'm on this topic, let me remember to ask you how can people find you if they want to learn more about what they, what you're doing?

00:26:05.942 --> 00:26:19.046
I love to meet new people, so that's a great way for us to connect and, of course, if I can ever support any of your listeners, I'd be happy to, so that's the best way for me.

00:26:28.135 --> 00:26:30.799
Yeah, perfect, and I'll make sure that's in the show notes.

00:26:30.799 --> 00:26:38.721
So I find that when I'm listening to a podcast, I am thinking, wow, good point, wow, good point, wow, good point.

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And then I don't necessarily remember it all because I was doing the laundry or driving the car or whatever at the same time.

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So I always want to ask, as we reach toward the end here, what is the one thing that somebody who's listening you really want them to remember?

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This thing and take it away from this discussion?

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I might call it the OMG, like I have to remember this one thing.

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What would you say that is?

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To redesign your life.

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Whenever you wonder how can I live happier, answer those questions.

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Let yourself instead use this blank canvas of your next chapter as an opportunity to truly script it the way you want to, not the way you've been conditioned to.

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I love it and I love that you said when you hear or feel that nudge, because that's our intuition, which usually is right on the money for sure, and always good to listen to that.

00:27:56.734 --> 00:27:58.880
Absolutely Well, Wendy.

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Thank you so much for joining me.

00:28:00.303 --> 00:28:01.992
It's been a great discussion.

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00:28:03.696 --> 00:28:06.041
There's so much fun here to discuss, so I really appreciate you having me on today.

00:28:10.821 --> 00:28:13.127
So I really appreciate you having me on today.

00:28:13.127 --> 00:28:23.101
Wendy and I are continuing the conversation over on Patreon specifically with some tips she is giving for that emptiness phase that you heard me talking about.

00:28:23.101 --> 00:28:29.250
That is one of the sort of emotional, I'm not sure what to do struggle periods.

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So make sure that you have joined me in the Patreon midlife pivot community, patreoncom slash mind your midlife and you will grab that as well.

00:28:40.039 --> 00:28:43.513
Hope to see you there and I love that.

00:28:43.634 --> 00:28:47.461
Wendy's OMG was number one.

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Notice the nudge that's intuition, gut feeling so powerful.

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And then give yourself permission to investigate.

00:28:55.433 --> 00:29:16.549
Let's look forward, as opposed to always turning back forward to say, okay, now I see, now I know, now I recognize, or maybe even, as you heard Shannon Russell some episodes ago when we talked about your second act, I'll make sure that's in the show notes.

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Also, as you heard her say, maybe you're just a different person now than you were when you made a different choice.

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That's okay.

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Let's go forward.

00:29:26.576 --> 00:29:31.760
Give yourself permission to follow that and see where the path goes.

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Fantastic way to leave this episode.

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If you're listening on Apple podcasts, it would be so amazing if any episodes have been meaningful to you, if you would go and leave a five-star rating and write a quick review.

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It helps so much to get the podcast out to the people who will really appreciate it and benefit from it.

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So thank you for that and, in the meantime, make sure you remember to slow down, maybe take a breath, notice what's around you, what's going on in your head, and let's create something amazing.

Dr. Wendy O'Connor Profile Photo

Dr. Wendy O'Connor

Positive Psychologist + Life Strategist for Women

Dr. Wendy is a Stanford trained positive psychologist and success coach. She helps women design their most meaningful, intentional, and fulfilling lives. Utilizing her evidenced-based success method, Dr. Wendy has helped thousands of women worldwide live a life they're obsessed with.