Feb. 24, 2026
Mapping Change With Courage; Life Design For Real Life with Ashley Jablow
Transitions can arrive by choice. And sometimes they arrive without asking our permission. In this episode of Connect Inspire Create, I chat with Ashley Jablow, founder of Wayfinders Collective and creator of Life Design School, to explore what it means to redesign your life during seasons of change. So what is Life Design, really? In our conversation, we explore: • How Life Design differs from traditional goal setting • How to begin when the ground feels unfamiliar • How cl...
Transitions can arrive by choice. And sometimes they arrive without asking our permission.
In this episode of Connect Inspire Create, I chat with Ashley Jablow, founder of Wayfinders Collective and creator of Life Design School, to explore what it means to redesign your life during seasons of change.
So what is Life Design, really?
In our conversation, we explore:
• How Life Design differs from traditional goal setting
• How to begin when the ground feels unfamiliar
• How clarity and courage coexist with grief
• Why community matters in seasons of reinvention
• What real-life courage actually looks like
I also share, gently, that I am newly navigating widowhood — a word I am still learning to say. Some transitions are chosen. Some are not. Both ask something of us.
If you’re in a season where the old map no longer fits, this conversation may feel steadying.
Ashley is generously offering her free Clarity Kit — a 30-minute on-demand workshop to help you diagnose where you’re getting stuck and get clear about the change you want to make.
If you’re feeling stuck or at a crossroads, this is a beautiful place to begin.
And as always, I’ll leave you with this:
If you chose one gentle, meaningful step this week… what might you focus on?
Thank you for slowing down with us.
Connect with Ashley Jablow
I’m Carol Clegg, your host, an accountability coach and curious conversationalist inviting guests from a wide range of backgrounds to share insights on how they live, think, and navigate change.
Here, we explore:
• living with intention and self-trust
• alternative ways of thinking and being
• creativity, purpose, and personal growth
If you enjoy reflection, fresh perspectives, and honest dialogue, this space is for you.
If you’d like to experience this work in community, I host a complimentary monthly Accountability Circle a supportive space to pause, gain clarity, and choose a gentle next step forward. More info at https://carolclegg.com/accountabilitycircle
For those ready for deeper, more consistent support, I also offer a 90-day Accountability Package, designed to help you move from scattered ideas to steady, sustainable momentum.
You can learn more at carolclegg.com,
Let’s connect on LinkedIn and Instagram, or join my LinkedIn Group Flourish: A Community for Women Business Owners
I am your host Carol Clegg. As a small business coach, I partner with women solopreneurs in midlife, to confidently step out of overwhelm and create a fresh path to success through tailored accountability and mindset coaching, integrated with the powerful Positive Intelligence program. Struggling with procrastination, finding balance in your business and personal life, and cultivating a positive mindset?
Let’s chat!
BOOK your ✅ 30 minute complimentary discovery call
carolclegg.com or book your call here https://bit.ly/discoverycallwithcarol
Chapters
00:00 - A Slower Season Begins
00:49 - Meet Ashley And Her Story
02:28 - Becoming An Artist In Midlife
04:49 - The Layoff As A Turning Point
07:40 - Defining Life Design
10:55 - Courage, Risk, And Perfectionism
14:45 - Right-Sized Experiments Over Big Bets
18:08 - Clarity Before Solutions
20:45 - A Gentle First Step And Where To Connect
29:56 - Host’s Closing And Invitations
Transcript
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Welcome everybody to Connect Inspire Create, a podcast exploring meaningful conversations about life, work, creativity, and the ways that we can grow.
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As I step into this new season seven, my show is actually taking a fresh direction.
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Connect Inspire Create is now focusing on slowing down the conversation just enough to notice what inspires us and how these insights can help shape what we create in our lives.
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So I am Carol Clegg, your host.
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I call myself your gentle accountability coach.
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And I'm inviting my guests now from a wide range of backgrounds to just share insights on how they live, work, think, and navigate the wonderful challenges of just being a human in our world.
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So joining me today is my guest, Ashley Jablot.
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And Ashley, I never asked you, I wanted to how to pronounce your surname.
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I said surname, last name correctly.
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So I hope I didn't butcher it.
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It's very close.
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It's very close.
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I'm Ashley Jablo.
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And Carol, it's so great to be here with you today.
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And I just need to kind of name when you said we're here to slow down the conversation.
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I felt myself take a really deep exhale.
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So I really appreciate you naming that.
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It just felt good to kind of ground and be here with you.
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Thank you.
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Yeah, I think that's important, you know, that we do take that time and just not rush into these conversations because they're so precious and important.
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And I'm thrilled that you're here today to join me.
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So I wanted to just give a brief introduction.
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So Ashley is the founder of Wayfinders Collective and the creator of Life Design School.
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And she helps people reimagine what's possible, both in work, leadership, and life.
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And I like to share that your work lives, as you said, at the intersection of innovation, creativity, and practical change.
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And Ashley is combines her formal training as a coach and now guides people to apply the methods and mindsets of innovation to their own career and life design.
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So actually, that's kind of the official introduction, but I would love to just start with something a little more personal.
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When people first meet you, what is one thing that they're often surprised to learn about you?
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Oh, that's a good one.
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I was actually imagining the question you were going to ask me is what's one thing people always learn about you?
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And my answer to that is that I'm a mom.
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Being a mom is a very big part of my identity, my daily life, my routine.
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But one thing that people are surprised, I think it's my own journey with becoming an artist.
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Especially people who have known me for a long time.
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I've I've sort of uncovered a side of myself in my 40s that I didn't expect.
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And that is, I am someone who loves to create art.
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I've always been creative, but I grew up with a very talented artist mother.
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And I think that I have so much appreciation and gratitude for my mom.
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And I think also in our family, she sort of held that role.
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And so as I'm growing into myself at this stage of my life, I have really started to express myself creatively through tangible art.
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And that's not something, again, especially people who've known me for a long time would say, Ashley, doing art, that's unexpected.
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Wonderful.
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That just brings such a warm feeling to me because I think it's such a gift to find an outlet where you can just explore and then embrace and get joy out of that.
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Yeah, and practice, practice the discomfort of learning something and the discomfort of having an idea in your mind or your heart, and then figuring out how to translate that into something that you feel um represents your vision.
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I mean, it's a kind of a microcosm for personal growth in many ways.
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Yeah.
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No, I love you know what you said because I think often we stilt ourselves or hold ourselves back because I love creating, but I always tell them, you're not good enough.
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You know, you can't do this.
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So what you just said there about learning, you know, we often think we just have to be gifted artists to be able to play in the art realm.
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And why not learn, like we do in so many other areas of our lives.
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So that's where I'm going to bridge over to let's talk about life design during the seasons of transition, especially when the old map no longer fits.
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And I know that transitions can arrive by choice, and sometimes they arrive without asking our permission.
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And I did notice on your website that you mentioned in 2017, you shared that you were laid off from what you thought was your dream job, and that opened up a whole new pathway for you.
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Can you share just a little bit about that revelation?
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Oh, absolutely.
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And it's it's so true that sometimes we we pick our heads up and look around and realize there needs to be a transition, there needs to be change.
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And then other times it's foisted upon us, right?
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With or without our consent, really.
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And so, yes, my experience getting laid off in 2017, I really thought I had arrived when I took on that job.
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I had worked in really prestigious organizations.
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I had kind of climbed the professional mountain that I thought I was meant to climb.
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And very unexpectedly was told, no, actually, you have not been successful here, and uh, we need to let you go.
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And it's funny.
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Carol, I see you rolling your eyes, and I I I feel that way now for sure.
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At the time, it was such a gut punch.
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And in fact, I I really I've learned to think about getting laid off a bit like getting dumped in a romantic relationship.
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You know, there's, and actually, if you map kind of a romantic relationship along with professional ones, there's often that honeymoon phase.
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There's that, like, oh, he leaves his dishes in the sink, but I still love him.
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And then there's sometimes that like something has changed and I'm not sure what it is.
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And I had those feelings before I got laid off, but I really was blindsided.
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I didn't expect to get dumped.
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And so I went through a period of grieving, I went through a period of real questioning, you know, not just what do I do now, but importantly, how do I explain what's just happened to me?
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It was a real bruise, not just to my ego, but my sense of self.
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I've always been very ambitious, I've been a high achiever.
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And so to be kind of knocked off that pedestal that I had put myself on was really bruising in so many ways.
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And at the same time, I knew that I really, like deep down, there was this kernel of truth.
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I knew I had been given a gift because when I really stopped to consider it, I could see that the path I was heading down was not truly an authentic or even like integrated path.
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I often felt that my work life and my real life were two separate things.
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And I did even in that moment know that I was craving bringing them more closely together.
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And so, boy, I mean, you know, seasons of transition, they take as long as they're gonna take.
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I made some quick progress.
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And also, in many ways, I feel like I'm still in the midst of that transition.
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But it has been a hugely instrumental uh experience for me that has informed my understanding of what it's like to navigate change, particularly as an established professional, as an established person, and how to do it with integrity and intention and creativity.
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And I just, you know, as I shared with you earlier, but now for myself as someone who is newly navigating widowhood, even that word is something I haven't even said a whole lot of times.
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So I'm still learning to talk about that.
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But just as we said, some transitions are chosen and some are not.
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And so if we come back to, you know, what is life design really?
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How does life design apply when these changes feel imposed on us?
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Yeah, yeah.
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Well, first I just want to acknowledge again how honored I am to get to be here with you today as you navigate this transition yourself.
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And, you know, the way I think about life design is that it really is a curious and intentional and creative approach to understanding who you are at this stage in your life, really defining what matters to you, imagining a resonant and authentic future for yourself, and then taking iterative, consistent, kind of incremental steps every day to get yourself to that future, to realize that future.
00:10:08.000 --> 00:10:24.639
And I think it's particularly important to go through the process, the experience of life design when you have found yourself in a place where life is telling you you have to change, even if you don't want to.
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Threats.
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Because I I really believe that this is, you know, I mean, we could get really deep here, Clara, Carol.
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I really believe that this is the one shot we've got in this lifetime, right?
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And so whether it's imposed or it's by choice, recognizing that we are always gifted opportunities to recalibrate.
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We are always gifted opportunities to learn more and to deepen our sense of purpose and meaning in this one life that we have.
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And so I believe life design as as I've designed it, as I've defined it, is a way of supporting people and guiding people to do that.
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Whether, again, whether you've chosen to transition or if the universe has decided, it's time.
00:11:20.960 --> 00:11:27.519
And that, yeah, I love what you share because having somebody to walk alongside you, to pull out courage.
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Courage suddenly was the word that came to me a little yesterday.
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And I was like, you know, what does courage look like?
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And you don't sit with this, you know, I'm feeling courageous and I can take on anything, but just bringing it back gently as a reminder that look for courage in certain situations.
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And as you said, sort of small incremental, you know, one little step and you're gonna fall way back again, but then you know, picking yourself up.
00:11:52.559 --> 00:11:55.759
So that brings me to a question about you know, redesigning.
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Why does redesigning your life in community matter?
00:12:01.919 --> 00:12:02.720
Oh gosh.
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Well, I mean, just purely knowing that you are not alone is so important.
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Like I I'll I'll share from my own story.
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When I got laid off, I did a lot of walking.
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I did a lot of walking just to pound the pavement and figure out like, how do I make sense of this?
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And I would put in podcasts actually, and I would carry a little notebook in my back pocket.
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And I mean, I literally I would stop wherever I was listening to something and make notes and write it down.
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And I felt very alone.
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I felt really isolated in this experience of this thing has just happened to me.
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I'm devastated, I'm embarrassed, I'm confused, I'm not feeling brave at all.
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Where do I even go from here?
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And so, as much as the walking and the quiet solitude and reflection was important, I also spent a lot of time when I got laid off talking to other people and asking them, like, how did you navigate these moments?
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What, you know, I'm I love learning about people's stories.
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I love looking for connections and and and lessons, right?
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So I would have coffee with people and I would say, How have you navigated getting laid off or a tough transition?
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And the thing that I learned was that actually they would say to me, Well, how are you doing it?
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Because I'm struggling here and I actually have this thing that I'm working through, and I don't know how to do it.
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And what I started to realize, and what really became kind of the genesis of Wayfinders Collective, my business, was this notion of navigating, whether it's navigating the open ocean like a traditional wayfinder, or navigating the pathways of our lives, it is perhaps one of the most universal human experiences.
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And yet we so often do it in isolation.
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We don't look around, you know, again, to extend that metaphor of navigating the ocean in our boat, right?
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We don't look around and realize that everyone is in a boat next to us.
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The whole ocean is filled with people, yeah, right?
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And so that was really my intention with starting Wayfinders Collective.
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And it's taken me a number of years to realize that community piece.
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Because as much as people are craving doing this work and learning about themselves and feeling less alone in community, it's also a very private experience, right?
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And so, how do you balance, even dance with we are all in this together?
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And also, this is a really sacred personal journey.
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So I would say you have to dance with that, but knowing that you are not actually alone, if you're being faced with questions and doubts and uncertainty, whether it's about work, it's about something in your family life, it's about your purpose, right?
00:15:26.159 --> 00:15:29.360
It can be about, you know, who am I becoming?
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Just know that as much as that feels really private and individualized to you, everyone is walking around asking these questions.
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And when you can turn towards someone you trust and say, can we talk about this together?
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You'll find the whole experience is so enriching and resonant and connecting.
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So I love that's that just absolutely resonates with me because it's so easy to put up the wall and go, this is such a private experience.
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And then I don't want to burden somebody with my over-emotional state.
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But what you said spoke about is approaching them and asking them for advice on how they walk their road, walk their journey, experience that I think that opens up for instead of dumping, you come straight forward and go, This is me, and then then sort of expecting, you know.
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So those are just those were very helpful words for me to hear today, is then approaching others, you know, to support you on your journey.
00:16:32.159 --> 00:16:37.840
Because, you know, being laid off and becoming a widow, we're not the only ones.
00:16:38.639 --> 00:16:52.159
As I said, there's many other people that, you know, walk this road, and we do need community, but in the right space, the right time to be vulnerable and to trust somebody to to walk that journey with you.
00:16:52.320 --> 00:17:04.799
So I wonder if there was anything that you could share just on saying, you know, we talk about courage, the word courage, and it's it's we kind of know what it is, but what can that really look like in real life?
00:17:05.519 --> 00:17:06.319
I love that.
00:17:06.480 --> 00:17:12.000
So I'm smiling because when I think about courage, I think about risk.
00:17:12.160 --> 00:17:15.519
Like, you know, they they they go together, right?
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If we need courage, it's because we are preparing to approach something that feels risky, feels hard, feels unknown, feels uncertain.
00:17:29.759 --> 00:17:34.240
And I have come, you know, and again, I said I was a high achiever.
00:17:34.559 --> 00:17:46.960
What I mean more directly is that for most of my life I have been a raging perfectionist, which is probably why I'm just only now coming into myself as an artist, right?
00:17:47.119 --> 00:17:52.000
Because the idea of perfection and art, they sort of don't go together.
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And so I have had a lifetime of avoiding risk because you can't expect to get things perfect when you're approaching something that's unknown.
00:18:05.920 --> 00:18:07.759
You've never done it before, right?
00:18:07.920 --> 00:18:22.160
And so a lot of my work with my clients and just personally myself is about reframing risk and really examining what it is and what it isn't.
00:18:22.480 --> 00:18:29.599
So when I think about risk, generally, when, you know, if I asked you like, what does risk look like?
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What does it feel like?
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Like we kind of immediately in our heads go to, I'm jumping out of an airplane without a parachute, right?
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Or I've taken my life savings and I'm going to the casinos, right?
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Really big, scary, dangerous risk.
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That's not the kind of risk that I think any of us really want to be taking, need to be taking, right?
00:18:57.359 --> 00:18:59.680
It those are not safe risks.
00:19:00.000 --> 00:19:17.279
But I think when we're talking about courageously facing transition, we need to be talking about safe, productive, even helpful risks that we can start practicing having courage around, right?
00:19:17.599 --> 00:19:38.160
So great example is, or just one example that comes to mind, is let's say that you are thinking of starting a new retail store, like downtown somewhere, and there are all these products you love, and you just couldn't, you get so excited thinking about, I want to be a shop owner, right?
00:19:38.319 --> 00:19:42.640
And actually, my mom has had a retail store for 40 plus years.
00:19:42.720 --> 00:19:44.799
So this is an example I know well.
00:19:45.200 --> 00:19:49.519
So let's imagine you say, okay, I want to open up this retail store.
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I know all the products I'm interested in.
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I'm gonna go down, there's a space that's open for rent, and I'm gonna sign a 10-year lease and I'm gonna open my doors in six weeks, right?
00:20:01.119 --> 00:20:03.119
Ah, I saw your face, right, Carol.
00:20:03.200 --> 00:20:08.960
It's like, oh my God, I can even feel like in my stomach that doesn't feel safe, right?
00:20:09.359 --> 00:20:25.279
So the question becomes what are some small, fast, inexpensive risks that you can take that can help you learn about whether this is a good idea, right?
00:20:25.920 --> 00:20:30.640
One potential idea might be, well, there are a few products I like.
00:20:30.799 --> 00:20:34.480
I'm gonna sign up to sell at a pop-up market.
00:20:35.119 --> 00:20:35.599
Right.
00:20:36.079 --> 00:20:43.119
Now that might be the right size risk, and you might have the level of courage ready to match that.
00:20:43.279 --> 00:20:49.039
But I would offer that that's not even the smallest, fastest, least expensive thing you could try.
00:20:49.200 --> 00:20:49.519
Right.
00:20:49.759 --> 00:21:01.440
Maybe the actually the smallest thing you could do is say, there's one product I really like, and I'm gonna invite 10 friends over to my house for a glass of wine.
00:21:01.599 --> 00:21:05.599
I'm gonna show them what I've got, and I'm gonna ask them for their feedback.
00:21:05.920 --> 00:21:06.319
Right.
00:21:06.559 --> 00:21:11.279
That's the kind of risk that is absolutely something new.
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It's something unknown.
00:21:12.799 --> 00:21:16.000
We don't know if people are gonna like this, right?
00:21:16.400 --> 00:21:22.400
But it's like the level of courage required for that is much more manageable.
00:21:22.799 --> 00:21:26.319
And on top of that, you're going to learn, right?
00:21:26.480 --> 00:21:37.680
And I just really believe that when you can frame any risk in service of your learning, it starts to feel easier to be courageous about it.
00:21:38.000 --> 00:21:43.039
Because once you've tried it and you've learned, like, oh, they loved this product.
00:21:43.200 --> 00:21:47.680
And actually they'd be willing to pay more than I thought they would.
00:21:47.920 --> 00:21:48.240
Right.
00:21:48.480 --> 00:21:50.880
Now, what's the next thing I could do?
00:21:51.039 --> 00:21:56.319
The smallest, fastest, least expensive investment I could make, right?
00:21:56.880 --> 00:21:58.799
To help me learn more.
00:21:58.960 --> 00:22:03.839
And ultimately, You ladder your way up, perhaps, to that retail space.
00:22:04.079 --> 00:22:11.839
You may not, though, but either way, you have gotten smarter and you've practiced taking action.
00:22:12.000 --> 00:22:15.119
You've practiced building those courage muscles.
00:22:15.359 --> 00:22:18.319
And suddenly risks feel purposeful.
00:22:18.559 --> 00:22:20.559
They don't feel dangerous.
00:22:21.440 --> 00:22:30.160
Beautiful, beautiful picture explanation, how to take these just these small action steps without overwhelming yourself.
00:22:30.400 --> 00:22:49.680
And then bringing the community in, be that, you know, in a in whether it be even, you know, when you spoke about that and bringing people in, I sort of thought of the benefits of even a mastermind where you can explore the waters with people that you might know and get some feedback before, as you say, jumping into a 10-year lease.
00:22:49.759 --> 00:23:02.400
I mean, that always breaks my heart when I see small businesses in our area and they jump in and that, you know, there's in a couldn't you have taken a smaller step before jumping in into that huge big step.
00:23:02.480 --> 00:23:07.920
So Ashley, I know that you have a Clarity Kit workshop that you talk about.
00:23:08.160 --> 00:23:12.880
And I'd love to you to just tell me a little bit more, and I'll make sure that to put that link in.
00:23:13.039 --> 00:23:15.680
But that's for my listeners to explore.
00:23:15.759 --> 00:23:17.279
So tell us more about it.
00:23:17.680 --> 00:23:18.319
Absolutely.
00:23:18.480 --> 00:23:18.799
Yes.
00:23:18.960 --> 00:23:24.559
So so I I think you mentioned Carol, I've worked in innovation for many years.
00:23:24.799 --> 00:23:46.960
And so a lot of the coaching and teaching I do is about taking the methods and mindsets of innovation that companies, brands, even governments use to apply them to our own career and life decisions, our career and life crossroads.
00:23:47.200 --> 00:24:13.680
And one of the things that things that I learned working in innovation, you know, sitting inside federal agencies, for example, and helping them design and deliver new innovative services for citizens, is that often we jump right into solution mode without clarifying what problem we're actually trying to solve.
00:24:15.119 --> 00:24:17.599
And, you know, you see this a lot, actually.
00:24:17.759 --> 00:24:26.160
I see this a lot in coaching conversations where people say, I hate my job, and so I need to go get a new one.
00:24:27.359 --> 00:24:33.359
Now, the thing is, it's gonna sound kind of cliche and maybe even obvious, but it's worth stating.
00:24:33.599 --> 00:24:43.119
If you don't have the right problem, if you don't know the correct problem, you're not going to get to the right solution.
00:24:43.359 --> 00:24:50.400
And that's true in a job search, that's true in government agencies, that's true in any aspect of our lives.
00:24:50.640 --> 00:25:02.000
And so actually pausing to consider what is the problem I'm trying to solve is hugely important because almost like you imagine a big cruise ship, right?
00:25:02.160 --> 00:25:11.839
Where like you set out in a direction, and if it's not the correct direction, even by like one degree, you're gonna end up in the wrong place.
00:25:12.240 --> 00:25:20.720
So pausing to get clarity, which is the purpose of this workshop, so that you can really say, this is the problem I want to solve.
00:25:20.960 --> 00:25:29.599
So in the case of a job, for example, maybe it's you learn that it's not that I hate my job and that that's the problem.
00:25:29.920 --> 00:25:33.599
Maybe the problem is actually that you're not growing, right?
00:25:34.160 --> 00:25:43.200
That ultimately with doing the work of life design, that might lead you to say, well, the solution actually is still to get a new job.
00:25:43.440 --> 00:25:44.799
But it might not.
00:25:44.960 --> 00:25:51.359
It might look like any other number of solutions to solve for I'm not growing.
00:25:51.599 --> 00:25:51.839
Right.
00:25:52.160 --> 00:26:04.880
That you could still, you know, you can look for other opportunities or have conversations right where you are, as opposed to uplifting yourself and having to move and change, that there could be solutions right under your nose.
00:26:05.359 --> 00:26:06.000
Absolutely.
00:26:06.160 --> 00:26:08.079
So that's the intention of the workshop.
00:26:08.160 --> 00:26:09.440
It's totally free.
00:26:09.680 --> 00:26:14.880
It's a 30-minute video with me where I walk you through some life design exercises.
00:26:15.039 --> 00:26:24.880
Again, with the goal of by the time you're done, you can really say, this is the problem I want to solve, and feel really confident that that's the direction you want to head in.
00:26:25.119 --> 00:26:25.519
Lovely.
00:26:25.599 --> 00:26:33.119
And I've got that at lifedesignschool.co backslash kit, and I'll make sure that that is in the show notes.
00:26:33.359 --> 00:26:37.599
Ashley, as we close out our wonderful conversation, and thank you.
00:26:37.839 --> 00:26:47.279
If somebody listening wanted one just very gentle, meaningful step to take this week, what would you invite them to focus on?
00:26:47.759 --> 00:26:49.759
I love the idea of gentle.
00:26:50.319 --> 00:26:55.839
I'm I'm a very sensitive person, so gentle is like a word that speaks to my heart.
00:26:56.480 --> 00:26:57.119
I think.
00:26:58.799 --> 00:27:12.319
Oh, there's so many lovely things I would say, but I think if I could offer just one thing to do this week in and in in a gentle way, it would be to get some fresh air.
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