Unlocking Midlife Reinvention (Without Burning It All Down) with Ashley Jablow

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Timestamps:
00:00 — Cold Open & Intro
04:00 — Why Happiness Isn’t Constant (and That’s Okay)
07:05 — Laid Off After “I’ve Arrived”: The Wake-Up Call
10:25 — The Power of Onlyness: Owning Your Unique Story
13:52 — Stop Fixing Your Life. Start Designing It.
16:20 — The Four Steps of Life Design (Discover, Define, Imagine, Iterate)
23:41 — Midlife Crisis or Midlife Reinvention?
26:18 — The Real Risk of Staying Stuck
32:52 — The Learning Loop: Plan → Act → Update
40:12 — Clarity vs Certainty: The Mistake Every Leader Makes

Ashley Jablow (00:02.00)
And essentially the idea is that nobody shares the same Onlyness and that in fact when we can stand in our Onlyness, we can bring ideas into being in ways that no one else could.

And you think about it, like the LinkedIn update, right? I’ve got the new job that everybody’s oohing and aahing over and now suddenly it’s gone and how do I explain myself? And actually, you know…

Skot Waldron (00:36.00)
When I’m not hosting Unlocked, I’m speaking at events all over the world. I’m helping leaders and I’m helping teams communicate better. I’m helping them build trust faster and actually enjoy working together. I’ve spoken for companies like The Home Depot. I’ve spoken at national architectural firms. I’ve spoken for pharmaceutical company offsites. I’ve spoken at associations, you name it.

With 99% of attendees of all those events, over 1800 people have reviewed me at this point. 99% of them saying they got some value. That’s pretty awesome. Even the caterers have thanked me. And if they are thanking me and they’ve heard a lot of talks and they’re busy doing their jobs, that’s saying something. If you’re an event planner looking for a speaker who’s really easy to work with, trust me, I want to be the last thing you’re worried about on event day. I’m going to take care of you. And who actually delivers value for your audience that they are going to use on Monday morning when they return to the office, then let’s talk.

We all experience something in our, well, I’m going to say all. I’m going to say most of us. Maybe most of us experience this kind of mid-career crisis, midlife crisis is what we like to call it. This, I don’t know, people that jump out of airplanes or that go climb a mountain or that, you know, by a motorcycle and learn how to do wheelies. I don’t know. That might be you. I went to the hairdresser, and I told them to do whatever they wanted with my gray hair. And I was there like, what do you want to do with it? I said, “I don’t care, do whatever you want.” They said, “Do you want to like color it, like darken it?” And I was like, “I don’t care.” So, she started doing it only to find out that all the, her coworkers in the back were like, “Why are you changing the color of his gray hair?” Everybody wants the gray… So, anyway, people are jealous. They got mad at her because they were trying to take the gray out of my hair. Anyway, I digress.

But the thing here is that we all go through this moment of wanting something. We were questioning what we’re doing in life. Are we making an impact? Are we creating the thing that we want to create? And is this transition moment important for me and what I’m doing in life? And what are my kids going to think about me and my family? Like, there’s all this stuff that goes through our minds.

Ashley is going to be on today. Ashley Jablow and she’s done some pretty cool thinking around what we call life design. Life design and we’re going to talk about that concept. I have a question about that in a little bit. She’s done some pretty cool things around this. And I want you to listen up. This is going to be a conceptual reflective episode that I hope that you’re going to get something out of. If you listen and take away some of the nuggets she puts in here, she gives you some questions, some actions you can actually take.

Ashley Jablow (Jab-lo) is the founder of Wayfinders Collective and creator of Life Design School, a creative studio for people in career and life transition. A seasoned facilitator, keynote speaker, coach, and design strategist, Ashley blends design thinking, authenticity, and creative tools to spark clarity and action. She’s also the artist and author of 100 Days of Designing My Life. We’re going to tell you about that. It’s really cool. Actually, I like it. A guided journal series for reflection and reinvention.

So, y ‘all ready to get reinvented? Here we go.

Hello, Ashley. It’s good to see you.

Ashley Jablow (04:03.00)
Hello. It’s so great to be here with you. Thank you for having me today.

Skot Waldron (04:08.00)
And if anybody is not watching this on video, I hope you see how happy Ashley is right now. Like, you know, it’s clearly not because of me. It’s just because of who she is. Right? Who she is. Yeah?

Ashley Jablow (04:24.00)
I’m not sure about that. I’m not sure about that. I’ve been looking forward to our
conversation for sure. But I am generally a smiley person. That’s just how I show
up in the world, I guess.

Skot Waldron (04:35.00)
Do you smile when you cry? Are you like one of those people that like smile cry?

Ashley Jablow (04:40.00)
Well, I, um, I cry when I’m happy. So probably.

Skot Waldron (04:45.00)
Okay. Fair enough. That’s okay. Um, yeah, that’s good. That’s good. So, well, I think this energy you have is a result of, you know, the work you’ve done and the work that you’re now sharing with other people. I mean, would you attribute it, some of it, to that? Yeah.

Ashley Jablow (05:05.00)
Oh, very much so. I mean, I think, you know, it’s that whole nature versus nurture conversation, right? I think I probably have always been an optimistic person. And I just sort of tend towards positive and happy. And I also think that the, I think you’re right that the ways I’ve learned both to work and to hold myself, right? So having worked in innovation, I have a set of tools in my toolkit that help me resolve life’s problems differently. And then training as a coach, I also have a set of methods and mindsets that really support me to stay resilient and grounded even during challenging times.

So, it’s probably a little bit like nature, this is me and also nurture, this is how I have evolved to move through the world. Yeah.

Skot Waldron (06:00.00)
Yeah. I mean, nobody told you that because it’s your nature, you have to be this way the rest of your life, you know? There’s a lot of things that can happen in life that will turn us around and stump us up and, you know, create situations where we don’t feel those happy feelings all the time.

And in fact, that’s where I kind of want to start with you. You had one of those moments when you were laid off. Many people have been in that same boat. So, can you tell us that story?

Ashley Jablow (06:33.00)
Yeah, absolutely. Well, and, you know, playing in the back of my mind, I know we’ve come today to kind of start around one of my own life crises, we could call it. And I’m reminded that life is always throwing us challenges. I mean, just this morning, I was working through some really pretty serious stuff with my family, right? Which we don’t need to get into today, but it’s just a reminder that there’s always stuff that comes up. You know, I’m happy in the midst of these challenges and, and I face them too, right? So, I don’t want anyone listening or watching thinking I have figured this all out, right? We are all going the same process.

Skot Waldron (07:18.00)
That’s why I had you on the show, Ashley. Never mind, everybody. I’m sorry. Let’s do it. No. I don’t think we, any of us, figured out, which is why people still listen to shows like yes because we’re all trying start figuring out. Okay, go ahead.

Ashley Jablow (07:34.00)
Absolutely. Yeah. So, yes. So, my career story very much is of a young, ambitious, high achieving woman who went out to try to get the biggest, baddest job she could find. And more often than not, I was really fortunate to be able to reach it. So, I have worked at some of the world’s most well-known and beloved brands and organizations. I worked at IDEO, kind of one of the originators of Design Thinking and Innovation. I had the privilege of serving in the Obama administration. I mean, I’ve really been in some incredible professional settings. And more often than not, I have found in many cases, I felt like a square peg in a round hole where I just knew almost immediately that it wasn’t a fit.

So fast forward, I left the White House. I had been working with a coach to find what I hoped would be my dream job, my next job after that experience. And I landed it. I found an incredible role working with a small Spanish design firm. I joined their executive team. And in many ways, I felt, you know, very much hand on hips. Like, I have arrived. And I mean, I’ll just, like, it was such a baffling experience to be at such a high height. And then shortly after, just about 10 months later, I got laid off. And I know looking back on it, there were signs, there were clues, but at the time, it felt really like the rug had been pulled out from under me. And I really had to reconcile not just what did this mean for my profession and for the story I would tell people about what happened, but what did this mean for me as a person? And I think it was really the beginning of my curiosity around how do I align, you know, my work life on the one hand and my real life on the other hand. You know, how might I bring those two pieces of me together so that I could feel more integrated, more aligned, more whole? And that has been, in many ways, the driver of the business I’ve built today.

Skot Waldron (09:59.00)
What did you make it mean about you as a person when that happened?

Ashley Jablow (10:03.00)
Well, I really wrestled with that in the beginning, and I was worried about what it meant you know, I mean my ego really took a blow when I got laid off. I remember I went walking a lot just to like pound the pavement and try to make sense of particularly how was I going to tell people about what happened because that, you know, you think about it, like the LinkedIn update, right? I’ve got the new job that everybody’s oohing and aahing over and now suddenly it’s gone and how do I explain myself?

And actually, you know, one of the things that really resonated with me that really served me, we were talking earlier about learning and how much we love to learn. I came across an author named Nilofer Merchant, who had just recently written a book called The Power of Onlyness. And it, I mean, if you can go back and say like one thing had an outsized impact on me and how I started to make sense of what had happened and my story, it was Nilofer’s book.

So very briefly, the idea of Onlyness, as Nilofer describes it, is each person’s unique combination of history, experience, visions, and dreams. And essentially, the idea is that nobody shares the same Onlyness. And that in fact, when we can stand in our Onlyness, we can bring ideas into being in ways that no one else could. And for me, the way I started to hear that was that actually by accepting and bringing in my own experience getting laid off. It was actually like my own competitive advantage, if you will, right?

For a high achiever trying to figure out, like how do I make sense of this? Nilofer’s book really gave me the initial permission to say, “What if I embrace this really challenging moment in my professional and personal life, and instead consider how can it be additive to where I’m going next.

Skot Waldron (12:25.00)
That is a mindset shift. Yeah?

I mean, I think often people walk through life, and we are problem solving machines. That’s all we do all day long is solve problems. How do I heat up this hot pocket? I have to solve the problem. I need to find, fix it and put it in the microwave. So not that I eat hot pockets anymore because they burn my mouth all the time.

But when we think about people’s trying to fix it. I’m trying to fix my life. I’m trying to fix me because something’s wrong with me because they laid me off. That miss, means something’s wrong with me because I didn’t fit, you know? I’m saying everybody has that idea. But how do you get people to stop trying to like fix their life and start designing their life?

Ashley Jablow (13:20.00)
Oh, what a powerful question.

So, I think the thing that maybe the, again, the mindset shift that I encourage people to make is rather than jumping to solutions, right? And let’s be real. Like when we’re facing a challenge or a problem in our lives and our careers, there’s urgency to want to fix it, right? You know, like I hate my job, I’m going to go get a new job. What happens is we will rush to problem solving very often. And occasionally that works. Like there’s a reason we solve problems. It works. And I mean, maybe I speak from personal experience, but if you have ever left one job because you hated it and moved to another job only to find that the problems from the first job followed you to the next one, right? Again, raising my hand here, admittedly, there needs to be another way. There needs to be another approach that helps us be more intentional with our problem solving, quote unquote, that helps us be more curious and more creative in how we are tackling this, right?

So, I think one of the really big differences, and this really comes from my work in innovation and helping companies and agencies and organizations do work differently and create change, there’s actually a process you can go through that, again, is more intentional, curious, and creative that gets you navigating that uncertainty more, I guess from a more empowered place while also solving your problem. Because ultimately, we want to solve that problem. We just don’t want to rush right into, ah, this is so painful, so, I need to go fix it right now.

So, there are Four Steps that I teach all of my coaching clients that I share with, you know, I mean, truly I run my husband through these steps many times.

Skot Waldron (15:26.00)
Does he like that?

Ashley Jablow (15:27.00)
I use them myself. He does. You know, my 12-year-old isn’t going for it. My son is like, mom.

Skot Waldron (15:32.00)
Okay. I was wondering about that.

My wife often says to me, Skot, stop coaching me. So don’t give me that. I’d be really careful. My kids, on the other hand, my daughter’s like, all into it. She’s like, tell me, you support. So, I get the reverse.

Ashley Jablow (15:46.00)
Oh, I love that. I love that. Yeah.

So, my son is on to me and he refuses, but my husband is a very, I’m thankful, he’s a very willing co-conspirator in this. But maybe it would help if I just kind of walk through these four areas just to get people kind of thinking through how they might apply these steps in their own search. Does that sound?

Skot Waldron (16:06.00)
Yeah, I think that that would be great. And I want you to, yeah, I want you to explain them, keep them punchy, because I want to, I want to go back and refer to them as we talked through this a little bit.

Ashley Jablow (16:18.00)
Absolutely.

So, the first step really is to Discover. And the way I think about this is really being curious and reflecting on who you are today. I know for many of us, you know, a number of years into our career, we are not the same person that we were when we chose a major in college, for example, right? So, taking a beat and discovering who am I today and what is the world around me look like today. So that’s the first one.

The second is to Define. So, what are your priorities? What are the constraints that you live in right now? What are your values? And even what does success look like for the change that you’re working towards? So, pausing to really define your criteria, I think is obviously the second step is a very important one.

The third is to Imagine. You know, as grownups, we don’t often pause to actually, like, if I could wave a magic wand, what would I create for myself? We think play and imagination is for the five-year-olds on the playground. But actually pausing to have a vision and consider where do I want to go, what does a resonant an authentic future look like for me. It’s super important to know what our end goal is, right?

And then finally and perhaps maybe most importantly is called Iterate. And when I say Iterate, I mean taking daily, consistent, and incremental action rather than ripping off the Band-Aid. You know, it’s about focusing on experiments or tests that you can run so that you can learn ultimately if the direction you want to head in is the right one.

Skot Waldron (18:04.00)
Okay. So, this process, I mean, it was interesting you talked about discovering who we are now. Let’s go back to this one for a second because this one caught my attention. And there’s, you know, studies and all these things that talk about how, when we’re young, we can’t imagine us being different when we get older. We can’t imagine that we’re going to have a different political viewpoint or a different value system or be married to this different person than us or have this different life than what we expected. I mean, I thought that I would live in a high -rise with a piano that looked out over the city, you know, like, no, I’m not that at all. Like, I live in the suburbs, you know, so it’s very much not like, but when we get to the point of being older, you know, we hit this like what we people call your midlife crisis, your mid-career crisis is what I kind of called mine when I transitioned into something else. I look back and go, of course I’m not the same person I was. I had all these life experiences, and I’m developed and I’m now married to this person who obviously has a huge impact on me.

So that Discover process, when you talk about it from that standpoint, is that what you’re talking about? Is like, and what are some cool questions that you used to like ask at that stage to really like understand.

Ashley Jablow (19:38.00)
So, I think it’s a, yes and for me. So yes, it’s absolutely about updating your sense of who you are today because you’re right. We are not the same people we were. Now I think some of that comes from questioning. And so, I’ll get to some questions in a moment. I think there’s a component more even like before that, which starts with noticing, starts paying attention, right? You could call this mindfulness. I think it looks perhaps a bit like mindfulness combined with reflection, right?

So, looking around yourself and considering, for example, how am I spending my time every day. You know, maybe it’s not even the compare and contrast of what did I think I was going to be doing when I graduated from college. But actually now, just what fills my day? What gives me energy? What takes energy away? Right. So, starting to notice and reflect on the life that we live in currently. Because, I mean, of course, you can’t know where you’re going if you don’t know where you’re starting from, right? So as much as we can without judgment, really just considering what’s going on both in me, inside me, as well as out in the world around me.

I think there’s something interesting about discovery, and I see this a lot with career changers right now with artificial intelligence, right? There is, for a number of us, there can be a fear around what’s happening, and what does this mean me and the job market.

Well, to take a Discovery mindset, right, is to open up your field of vision and look for inspiration and also research like what’s happening in the world right now? What’s happening in the job market? How are things changing because of artificial intelligence, for example? And as you’ve opened up that aperture and been able to see more, then you can move into defining and actually saying, what’s the opportunity here for me? Given the learning I’ve done about myself, about what matters to me, about where I am in my life, my skills, my strengths, and what’s happening out in the world, where could I uniquely fit?

Skot Waldron (22:14.00)
Smart. That whole noticing section is really important. Yeah? Because that’s where, because if I never notice, if I never have that sense of who I am or where I’m at in life, I probably won’t ever get to the like discover part to ask the question.

Ashley Jablow (22:33.00)
Well yes and you know I mean I live on autopilot a lot of the time too right so we all, you know, have to pick up our kiddos from school and make dinner and do the laundry and go to meetings and it’s very easy to get swept up in just the machinery of life and to design your life, to go back to your question, to design your life rather than fixing the problem really starts with saying, I need to carve out some space to notice, to discover and to reflect.

Skot Waldron (23:10.00)
You. I like how you reframe this idea of mid-career to like mid-life reinvention, like this mid-career crisis idea to reinventing. What that about. Tell me about that little shift of why people should think reinvention.

Ashley Jablow (23:25.00)
Well, I guess, you know, I’m a naturally happy person. And I also, one of my foundational beliefs is that we are always evolving. We always get to change. You know, I’m not the same person I was, and neither are you, right. So, this ability to reinvent, I think it feels different again than solving a problem. It feels more inspired, more hopeful, more creative, more innovative. And for me, that’s the space that I want to hold myself in. And it’s certainly the space that I want to be in when I’m working with my coaching clients. You know, it’s much more empowered and sort of evokes possibility. And that’s where we want to be when we are intentionally designing our next chapter.

Skot Waldron (24:15.00)
Yes, it does. When I talk about reinvention, it is about what’s possible. What is when we’re reinventing something, it is how do we not throw away what we had, right? How do we evolve it? You know? Oftentimes when I would go in and owning a design agency and running and going into clients. And I would say, do you want an evolution or a revolution, right? Like, what is that thing that you’re moving into and how much of that do you want to, like, take on and what does it mean for you in this project?

This evolves kind of into this idea of feeling stuck, which you often talk about too. And I think people in this mid-career, mid-life reinvention stage of where they’re at are looking for something. And they may feel stuck. And I talk to a lot of people like this too, feel stuck in my career, feel stuck in my marriage, feel stuck in where I am in life. And, you know, you’ve had a couple decades of work maybe at this point. And you’re like, what else is there? You know? And some people often say the phrase like, oh, it’s too late. It’s too late to start over. I’m just, I’m in this thing. I’m in, oh, you, you’re a little heart, right?

Ashley Jablow (25:37.00)
It hurts my heart, yes.

Skot Waldron (25:39.00)
But it’s, you know, what is that? What do you want people to understand about this idea of being stuck?

Ashley Jablow (25:46.00)
Yeah. Well, you know, it’s interesting. Even just running through our conversations so far. There’s this thread that I’m thinking through around taking a risk and around failure. And the reality when you have been working and living for a number of years at this point, right, is that you’ve created a life around you. You’ve created structures around you that are not simple to dismantle, nor do we always want to dismantle them, right? There’s a lot that we’ve poured into our lives up to this state. And so, it feels really risky to make a change. And I would say it’s risky not to, right?

So, the first thing I would just let people know, and I would really encourage everyone to consider is what’s the risk of staying stuck? And how does that compare to the risk of taking action, right? And we can talk about how to take action because I do believe there’s a simple and powerful way to do it that actually reduces our risk of failure. But that’s the first question to grapple with, right? What’s at stake if I don’t move forward in some way because often there are real risks. Yeah.

Skot Waldron (27:11.00)
Let’s use an example. I want to example this out here because this is fascinating to me. And this is all about me, Ashley, all the time.

Ashley Jablow (27:20.00)
I love it.

Skot Waldron (27:22.00)
All about me. Give me an example of how this works.

Ashley Jablow (27:27.00)
So, I’m thinking about coaching clients that I work with. Often that, you know, one that comes to mind, he has worked in one career track for, you know, the course of his career. And he is ready to make a change in his job. He is the breadwinner of the family. He has two young kids, one with special needs. They live in an expensive city, and he is finding that the job market is not kind right now to applicants, right? And there is this whisper for him around are there going to be layoffs, right? So, there is a lot in this person’s life that, you know, is like a stop sign for why we should not make a change, right? Like, I’m trying to hold it together. I’ve got a lot of people relying on me. And trust me, I am not saying that this person should go and just, like, quit their job and, you know, start a business, right? Like, I’m not saying that ripping the Band-Aid off is the right way to go. And I would acknowledge, and I’ve spoken with this client in particular about this, that the risks of allowing things to happen to him, right, of like, will there be a reduction in force, won’t there be? Am I willing to stay unhappy in this role? Right. We talked a lot about what are the consequences of staying in a situation that’s not working for you, right? Sure, you might be making good money, and it might be difficult to find a role that matches that right out at the gate. And also, what is the impact that being in a job for the majority of your waking day having on you when you come home to your family? What are you showing your children even inadvertently about what work is or could be when you allow yourself to stay stuck. And again, I’m not saying that that’s a simple problem to fix, right? But wow, when you can start having conversations with your partner, for example, about where are we going, right, that vision piece, what do we see for our future, given where we are today? What does good look like for our family in our lives.

Once you start having those conversations and painting that picture in your head, then you can start saying, okay, what are the micro adjustments I can begin to make? How can I chip away at this problem, right? In a way that over time will move me in the direction that I want to go in.

Does that make it more concrete?

Skot Waldron (30:34.00)
Yeah, I think it’s just the idea of looking at, because again, I was just talking to somebody this week and she’s not a client, but she was talking to me about her situation and how she’s feeling, I guess, stuck, right? Her husband has been affected by the federal layoffs and things like that. And now she’s a sole breadwinner and she’s in this job with, I would say an abusive boss and verbally, right? And she’s been with them since he started this thing. Now there’s other team members that she feels she needs to quote unquote protect. And she feels kind of stuck, you know? And this of like, oh, my family’s depending on me. Oh, these people at work are depending on me and you know what this boss he’s kind of depending on me too and like there’s all this outside pressure that comes into this thing.

So, when we’re looking at somebody like that right and the same idea okay what’s the cost of staying stuck what’s the cost of that because there is a cost to it just like there’s a cost to leaving, to making a transition. So what are some of those, like, little micro steps that we can take to help avoid, because you baited me a little bit to avoid failure. Like, you know, can you let go of any of your secret sauce? How do we not fail at anything in life, Ashley?

Ashley Jablow (31:57.00)
The truth is, I don’t want it to be secret. So I’m happy to share it.

So, you know, the person you’re talking about is a great example. There is a lot at stake, right? There’s a lot riding on her. There are also some real consequences of her continuing to be in this situation, right? And balancing that.

First step, I would actually, if anyone is feeling torn this way, I would encourage you to make two lists, right? Like what is the risk of staying where I am, what is the risk of moving? Because I actually think when we can get it out of our head and onto paper, it starts being something that we can manage, right? What gets measured, gets managed. So put it on piece of paper and really look at those two lists. That’s the first thing.

I think the thing about especially, again, taking this woman as an example, there are high stakes here to making a drastic move and there’s the potential for failure and could even be real consequential failure, right. Like if she just loses it one day and quits, where’s the safety net, right. How is she going to pay her mortgage. There are real questions to ask.

So, rather than taking drastic action and I know it’s uncomfortable, I know there’s an urgency and we want to just, again, like, you know, clean slate, I’m out of here. But rather than doing that, what I really want to encourage people to do is think about taking action like a little loop, like if you could imagine, almost like a cursive L, right, that just keeps going and going. There are really three steps in this loop that I want people to think about. And it’s really about taking a big change and breaking it down into the smallest, smallest step you could take. In fact, a question I often think about is, what is the smallest, fastest, cheapest thing that I could do or try right now to help me learn the most? And that’s what a loop represents.

So, the first part of taking action in this way is, I call it to Plan, right? Like, what is that step that I could take? And, just thinking of the top of my head, let’s imagine that your client, your friend decides, the first thing I need to solve for is, improve boundaries with my boss. That’s a big nut to crack, right.
So, I’m not advising that she says, she storms into his office and says, you’re disrespecting me and this is not working and all that, right?

So, the first loop, the smallest, fastest thing she could try to learn what works and what doesn’t, may look like, I don’t know, choosing to not be available after 4:30pm one day, just one day, right? Just like I’m closing out my email, I’m turning off my phone, I’m not available for the latest crisis. That’s the planning part of the loop, right? What am I going to do?

The second part of the loop is to Act, to try it. Again, the smallest thing we could try. So, okay, I’m going to plan it. It’s going to be tomorrow. I’m shutting down my email. I’m going to go take a walk from 4:30pm to 5:30pm because that’s when my boss usually calls, right?

Once she acts, she tries that out, the third part of the loop is to Update. And what I really mean by that, again, is to reflect what happened? You know, did her boss send out carrier pigeons? Like, did, you know, did the world stop turning, or did you actually assert even a quiet but meaningful boundary, right? And once you try that, again, because they are loops of learning, we can now say, okay, what am I going to plan next? What’s the next boundary I want to try to set? And truly, they should be as small as possible because we want to make the sustainable and the more small steps you take, they compound so that you’re getting yourself unstuck. You’re getting smarter as you take action, you’re actually learning what works and what doesn’t. You’re building momentum and confidence in yourself which is actually you’re learning to trust yourself because you’re taking action that’s in service of your goals, right? And you’re de-risking it ultimately.

So that over time, in the case of this woman, again, she’s starting to assert boundaries over and over and over again, so much so that, you know, the image that comes to mind is like a cruise ship that’s writing itself, right? Over time, she has asserted new boundaries with her boss. And over time, the relationship will actually adjust accordingly.

Skot Waldron (37:09.00)
Really good.

Let’s go into like a little lightning round thing. You cool with that?

Ashley Jablow (37:15.00)
Yeah, absolutely.

Skot Waldron (37:17.00)
All right. Fellow designer, I love visual storytelling. I love design principles. I apply them to leadership a lot in what I do. But what do you think is a design principle that everyone should apply to their career.

Ashley Jablow (37:35.00)
Oh, what a question. And no question, always in beta. We’re always in beta. We’re always experimenting. We’re always prototyping. We always get permission to try again.

Skot Waldron (37:49.00)
So good. Can I share one?

Ashley Jablow (37:52.00)
Yeah, I would love to hear.

Skot Waldron (37:53.00)
This question, I didn’t really prepare this for this because I just asked it. I was like, that’s a really fun question, you know, to think about it.

Ashley Jablow (38:00.00)
Yeah. How would you answer?

Skot Waldron (38:01.00)
Imitate before you iterate, right?

Ashley Jablow (38:04.00)
Ooh, tell me about that.

Skot Waldron (38:06.00)
Well, as you know, I’m teaching design students and I told them, I know you all think you’re brilliant designers and you don’t ever want to design anything that anybody else has done. You always want to create the original thing. But what I’m telling you is that a lot of it’s been done. And what I’m telling you, though, is you don’t need to, like, build the next brilliant thing yet. Just like, absorb the brilliance that’s already been created out there. So, I want you to go find the most brilliant poster design. And I want you from, you know, from Bauhaus, Moot, whatever you want, and I want you to copy it exactly how it is everything, color palettes, font styles, kerning, everything and copy it so you learn the craft and then I want you to tweak one thing on it to make it your own right.

So, that little, you know, imitate before you iterate like that’s what it is.

Ashley Jablow (39:03.00)
I love that.

Yeah. I was just going to say it reminds me of when my husband went to culinary school, and he was learning recipes and practicing all of that. And it was only after he got those reps under his belt, so to speak, that he felt confident enough to start tweaking the ingredients. It’s very similar.

Skot Waldron (39:23.00)
Yes. That’s a risky move. Start tweaking some stuff. Don’t mess up the whole dinner. That’s not, that’s messed up.

Okay. What you think, what is one of the biggest misconceptions about Life Design.

Ashley Jablow (39:40.00)
Confusing clarity and certainty. We often say we want clarity when what we’re actually hoping for is certainty. And I don’t know that that’s possible.

Skot Waldron (39:56.00)
A question that you ask yourself when you feel stuck.

Ashley Jablow (40:07.00)
I’m thinking hard because I am in some parts of my life, I’m feeling stuck right now. And if I’m honest, a question I’m asking right now is why isn’t it working? Because I get frustrated too, like all of us, right? And I did think earlier today, you know, again, along the Four Steps, where am I in this right now? And what am I ready to either Discover, Define, Imagine, or Iterate?

Skot Waldron (40:36.00)
And this goes back to your journals because your journals are great. I want you to introduce, okay, this is kind of not lightning. It’s very slow lightning. I want you to introduce your journal concept, that thing, it’s really cool. The way you’ve built this out and the way that you’ve, I don’t know, your creative brain is kind of like created these journals. Tell us about the journals really briefly, but I want to know like your favorite tool or your exercise.

Ashley Jablow (41:00.00)
Oh, that’s hard. That’s like choosing a favorite child.

Skot Waldron (41:03.00)
I know, but you know you have one, Ashley.

Ashley Jablow (41:04.00)
I’m not sure. I’m not sure.

Skot Waldron (41:05.00)
We know you have one.

Ashley Jablow (41:07.00)
Okay. So very, it’s a story back in 2020 when the whole world turned upside down, the only thing that seemed to make sense was for me to pick up my paint brushes and start creating. And I would never think of myself as an artist, but I went with it. And over the course of it ended up taking me two years, I created 100 watercolor postcards that combine design thinking frameworks, innovation methods, coaching tools, and other visuals and metaphors that I had been playing with into a collection called 100 Days of Designing My Life. Again, it took me two years to create those watercolors. It took me another two years to figure out what I was going to do with them because, boy, I was wanting certainty and clarity took its time to get here, in any event.

In 2024, I decided to self-publish four guided reflection journals based on that art. So each one contains 25 watercolors related to the Four Steps of Life Design. So, you can work through the whole series, or you can say, you know what? I feel like cultivating my imagination. I’m just going to go to those watercolors and those reflection questions. So, it’s been an incredible experience to create something tangible and put it out into the world and see how people are using the tools and reflection prompts to design their lives. And I don’t know if this is my favorite, but I do think this is when I’ve been thinking about it a lot. And it comes from a question I learned when I was training to become a coach, which is, what can’t you be with. What are the people, the experiences, the conflicts, the challenges that you avoid, that you deny that you can’t sit with, and getting curious about turning towards those things rather than pushing them away.

It’s a meaty question for sure, but that’s the one. It’s a very powerful one. Maybe not my favorite, but it’s what I’ve been thinking about it today.

Skot Waldron (43:31.00)
That’s a hard one. That’s like facing the demons. I mean, it’s kind of, there’s a quote I have in my book, it, you know, talks about how the person that frustrates you the most can be your greatest teacher. Those are the people you need to, not the people you love so much, like you get along with or like your clone that you can jam with really well. It’s the people that frustrate you, trigger you the most that you look at and you go, they’re going to teach me more about myself than anybody. And so, there’s really something powerful.

Ashley Jablow (44:05.00)
If I may, I know again, lightning round, but what comes to mind, because if someone’s listening to that question and they’re like, oh, it sounds terrible to even ask it, right? When I first asked myself that question, the first answer that came to mind was literally spilled milk because I was, my son was very little at the time and he was constantly overturning his cereal bowl. And so, it was striking to me that that’s what came to me first and what I think really key to mention is that the follow-up question when you’re asking what can’t you be with, is what’s important about that. And when you can explore not just the things that you can’t tolerate or that you won’t tolerate, but what is important about that, you will inevitably get to values, right, which are core to all of us. You’ll get to life priorities. You’ll get to ways of being, how you want to hold yourself in the world, right? So, it opens up a lot of positive discovery about yourself if you’re willing to wade through the muck of, “Ooh, I’m going to face the things I can’t tolerate.”

Skot Waldron (45:25.00)
Mm-mm-mm. Okay. Meaty, meaty, meaty.
Where do people get a hold of those journals? I want to know because I know somebody who might want one.

Ashley Jablow (45:37.00)
Amazing. So, all of my journals, courses, coaching, everything is available at www.lifedesignschool.co. And I’m also very active on Instagram and LinkedIn. So, if anyone would like to connect over there, I’m just @AshleyJablow.

Skot Waldron (45:55.00)
Cool. And you have a workshop that you do as well, yeah?

Ashley Jablow (45:58.00)
I do, yes. Actually, on Life Design
School, you can find a free on-demand workshop called The Clarity Kit. It’s really focused on helping you diagnose where you’re stuck, what’s keeping you stuck, and then helping you get to clarity actually through learning these Four Steps of Life Design and then rolling up your sleeves and working on a Life Design activity with me.

So, it’s all on-demand, totally free. I would love for people to check it out at life design school.

Skot Waldron (46:28.00)
That’s amazing. And the word clarity is so key. When I talk to people about communication, I’m digressing a little bit here. When I talk people about communication, I say, you know, “What’s your favorite type of communication that you, you love?” And people are like, “oh, I love giving people the place to just be. I love people giving people a care space. You know, just like, “I’m here for you. I can listen and do all the things and be there for you.”

Some people love to critique. Some people love to just like give you feedback and understand and how to fix your problem. Like they’re really good at that. And I say, well, do you know what the one is that people want the most in return. So they may love to give critique. They love to give like a care space. What’s the one they love to receive the most? Clarity.

People want clarity more than anything else in their life. And I applaud you for building that for people because I think that that’s amazing. So well done. Keep doing the work. Keep bringing clarity because that’s what people want about themselves, about others. And that’s what will help us have that, I guess, reinvention that we’re all looking for.

Ashley Jablow (47:37.00)
What a joy. I’ve loved this conversation. Like, I’m ready to just, you know, grab a drink and keep going. But I understand we have to stop.

Skot Waldron (47:46.00)
We do have to stop at some point, Ashley. You know, it can go on forever if I could. Yeah. But I don’t know who is listening.

Ashley Jablow (47:55.00)
This has been such a joy. Thank you for having me so much.

Skot Waldron (47:58.00)
Keep rocking it, Ashley. Thanks.

I hope you realize you don’t have to wait for the perfect moment to reinvent your life. If some of you are feeling stuck. If some of you are feeling like you just can’t risk it right now. I hope you learn something about how to switch a little bit of that mindset. How to transition from I’m being stuck to what is the next, what would she say, the three things what are the next uh, the simplest, the fastest, the cheapest thing that I can do to start moving. It’s hard to steer a bike that isn’t moving.

So, how do we just start moving, so we can start moving in the right direction. It doesn’t mean making some drastic, massive change, it just means getting started. And that whole mentality is a lot more empowering than the thought I’m stuck. We move from victim to opportunist. And that is so much better and more freeing for all of us if we can just have a little bit of that mentality.

Her Four Step framework. I like this. Discover. So, are you seeking to discover? Ask yourself the questions. Be curious about who you are today.

What about defining? Defining your priorities, the constraints, the values that you hold dear.

What about imagining a vision, a vision of where you could be, a vision of what you could do? What’s that vision? That is important because that’s the hope piece. Hope. We all need hope.

And then iterate, take daily action, start to put the things in action and make sure that we are still being true to who we are and representing who we are.

Thank you, Ashley, for some insights, some thoughts, some things that I’m going to take away that have helped me on this interview. And I’m going to continue to share and help with others, my clients included. They deserve to know the things you know, and I will share this episode with them. So, thanks everybody for being here.

If you want to find out more information about me or check out the show notes where there’s going to be more information and links to the things referenced in this episode, visit skotwaldron.com. And lastly, I’m asking for a little bit of love, just a little bit. So please take a moment, follow, rate the show. The algorithm is like that; it helps me get the word out. I really appreciate it.

Thank you. And until next time, stay Unlocked.