What's the Worst That Could Happen?--with Kate Crane

Most of the women I work with have never really failed. They've made the safe call, stayed on the established path, always landed on their feet. And at some point, that safety stopped feeling like safety and started feeling like a cage. My guest today has done the opposite her entire life — she's moved across the country with a boyfriend of one year, walked away from a stable career to follow a friend to a startup, talked her way into a kitchen in Manhattan with zero experience, and built a risk tolerance that most people would describe as unusually high. Not because she's reckless. Because she's lived through enough worst-case scenarios to know they're survivable.

Kate Crane is a career coach, founder of the coaching practice and podcast Direction Over Perfection, and someone whose own career path — art history to line cook to management consultant to DoorDash executive to startup operator to career coach — is proof that the most interesting paths are almost never linear. Her work helps young adults and people in career transition figure out what comes next, not by following a prescribed path, but by getting clear on what they actually want and taking directional steps toward it.

This conversation goes deep on something I've wanted to explore for a long time: how do you build a risk tolerance if you've spent your entire career avoiding risk? And is failure actually the problem — or is it the word itself that's doing the damage?

In this episode, you'll learn:

• How to evaluate risk as a spectrum rather than a binary — and the specific variables Kate uses to assess whether a leap is worth taking
• Why living through a worst-case scenario is often the thing that makes every future leap feel more possible
• What it means to "sunset" the word failure — and what to replace it with when something doesn't go the way you planned
• How tracking progress in small increments changes your relationship with setbacks in real time
• What alternative dimensions of success look like when you stop measuring only by revenue and résumé

The data is knowable. The worst case is survivable. And the reward is usually bigger than the risk.

Connect with Kate:

LinkedIn: https://www.linkedin.com/in/katecrane7/

Instagram: @directionoverperfection 

TikTok: @directionoverperfection

Podcast: Direction Over Perfection with Kate Crane (Spotify & Apple Podcasts)

Transcript

[00:00:00] Meg: Welcome to another episode of Changeology. My guest today is Kate Crane, who is a career coach and founder and host of the new podcast Direction Over Perfection. Kate, welcome

[00:00:16] Kate: Hi, thank you for having me

[00:00:19] Meg: So Kate, you are the founder of a career coaching practice for young adults, Direction Over Perfection. And I love one of the central tenets of that practice, which is that change is rarely linear. Despite how desperately we wish that it was linear, it's very often not. And you know this from personal experience because you have one of the most non-linear career paths I've ever seen.

And so to begin our conversation today, I'd love for you to give the audience kind of a bird's-eye view of your career to date.

[00:01:00] Kate: Yeah. Let me give you the quick version, because the long version is quite long. But, I started in the arts. So I was in the College of Fine Arts at Texas, studied art history, and I had a minor in business, and I got my dream job, after undergrad, after as well, like, having five internships, in the arts, kind of on, in that path.

but I was on this very linear track into the art gallery world. but then the crash of 2008 happened, and I got laid off six months after graduation. So this, like, perfect world, this perfect path I'd built for myself through all those internships into this first job, kind of evaporated. There were, very few places that were hiring, in early 2009.

The luxury market was effectively dead. we'd had a really hard time selling anything when I was at the gallery. and I was competing against people that had, master's in art history, and I had a little old BA. So I kind of had to just start over and say, "What do I wanna do with my life? What do I wanna do with my career?"

And at that point, I liked to go to yoga, I liked to cook, and I liked to watch the Food Network and host dinner parties. And so I started to, like, from scratch, think, think about what am I good at, and then what do I, what is this, like, next career I wanna build at the ripe age of 23? So I was trying, trying to decide if I wanted to go to culinary school or business school.

and a friend of mine was at culinary school, and, the CIA re- requires, Culinary Institute of America, they require that you work in a re- in a restaurant for six months, before enrolling. And so I thought, "Hey, that's a pretty good idea." Like, let's go try this before kind of embarking on another degree.

And so I talked my way into being a line cook at a fine dining restaurant, in Manhattan. One if by land, two if by sea. And there's a whole story there as well, but the long story short is that, I loved my experience. It was incredibly humbling. I, it started my real love for the restaurant space.

but I d- decided I didn't wanna be in the kitchen. In a macro sense, I wanted to own the kitchen. I wanted to be on the business side. So I ate some crow and moved home. I worked for my family, and I applied to business school. I focused in finance in business school to balance my art history background.

I felt like I needed that rubber stamp, in my resume and in my career. and then I went into management consulting. as a management consultant, I was focusing on process improvement in oil and gas. So, like, the management consulting industry is, fascinating, and I'm sure it's different today than it was, Gosh, like 15 years ago.

But, it, it was a great foundation for me, like learning how to be kind of a grown-up pr- professional. learning how to manage people, learning how to manage projects. really getting my first taste of finance. I ran forecasting for the company, my client, and then I went client side and worked there for another couple years.

and then the next big pivot, my then boyfriend, now husband said, "Hey, I don't really wanna be in Houston anymore. I think I wanna move to Denver. Do you wanna go with me?" And I thought, "Hmm, don't love this job anymore, and I'm kind of tired of working in deep water well containment. let's go to, let's go."

I also think it's a great idea for, to push boundaries, to, to get into uncomfortable situations. I had already lived in New York, and I'd had that, kind of like set of experiences, but my now husband had only lived in Houston and in Austin. So if this person that I'm like, you know, interested in thinking about building a life with says, "Hey, I wanna go try something new," I thought, "This is like an extra sign that I wanna be with this person."

So he and I went to Denver, and I used that as the opportunity to like, take a big pivot. I wanted to go back to food. I didn't know how or where, but there weirdly is a lot of CPG, in Denver. And so I was looking at, WhiteWave. They make Horizon Milk, and they're owned by Danone now. and there's, Lucerne is a cheese brand, and there's a bunch of, there's a lot actually of like organic startups that are in Boulder.

but that's, you know, long story short, where I found DoorDash. and I was... I mean, even better, like this is a restaurant. It's not just food. obsessed with it, but the first job they offered me was, on the driver side of the business. So I thought, "Okay, I'll, I'll do this. I can go do this. I'm excited to be here, but I really wanna be on the merchant, the restaurant side of the business.

but I'm gonna learn Dasher first." So I did that for a year. I ran the driver fleet for the mountain markets and then for the West Coast. And then again, talked my way back into the merchant side of the business. So I joined DoorDash Drive June of 2018.Trying to decide how much detail to go into here, 'cause some of it's interesting and some of it's not interesting.

But, Drive is a secondary product. So if you order a burrito from chipotle.com or Chipotle's app, it's actually a DoorDash driver that's fulfilling that, that delivery. And so I joined that team to grow that business. at a high level, that team, we did, like, 300,000 deliveries that first quarter, which translates to, like, 9 million in annualized revenue that when I first joined the team.

three years later when I rolled off and, and moved to a different part of the company, just my department, my team, which at that point was US restaurants, we did 20 million deliveries, was translated to 550 million in revenue. So such a wild and crazy, three years and, like, you know, a whole other podcast not focused on change to talk about that growth strategy and how we did that.

but the end of that story is that I was pregnant with my first child, and I didn't... I wanted to make sure I made enough space to be the mom I wanted to be, and I was concerned that being a general manager the way that I was a general manager, which was a lot of grind and a lot of, like, hands-on work, was not going to be conducive.

So opportunistically, I found another role at the company. this, like, fascinating man, Gokul Rajaram, was standing up corporate development for the first time, and so I took that opportunity to go work for Gokul. he'd been at Google and Facebook and Square and Caviar, and DoorDash got him through the acquisition of Caviar.

And, to go invest in my, like, business development and investment skills, like, this is a, a part of my professional acumen that I hadn't fully developed. So I took that leap and did that. I d- I had that role for about nine months. and then, you know, the next big pivot, a friend of mine, had gone over to another startup called Flock Safety and invited me to come stand up strategy and operations in the same model the way that DoorDash runs op strategy and operations.

so I took that leap, and that was- layers of things that was unexpected and interesting and hard and fun.it was moving from a true software-only business with a heavy logistical standpoint to a hardware business with a software overlay. and also it was a really well-funded, rapidly growing startup, that had still been scrapping together the background.

And so my job was to make sense of that operations. So we, transformed the data team, invested more heavily in business systems and so that we could use that data to make better decisions for the P&L and for their operations.I was there for about two and a half years, and that goes to the next pivot back to restaurants, and I joined OpenTable as their head of growth strategy, for most of twenty twenty-five leads to the next pivot, and the final one that kind of brings us to today.

the thing that I really love through my entire career is managing people and coaching people. And from, I'll say particularly in the DoorDash age, when I was, when I was... When I joined DoorDash, I was 31, and I was old lady. Like, it was a really, really young company. and so most of the people that I were managing were somewhere between 25 and 30.

and a lot of them were coming through this, like, quarter-life crisis of, I know I wanna work hard. They're clearly very smart and know how to work hard. They're at DoorDash, but they don't really know what they wanna do with their lives. They don't know what they wanna do, do with their careers or the next moves.

So I built my own kind of, like, people management skills around coaching the person and the work separately. So let's talk about your performance, but also let's talk about what do you wanna do, and how can I keep you engaged and excited? And maybe that's a stretch project. Maybe that's moving to a different department.

Maybe that's moving to a different company. But, like, you're gonna be a happy person and a hard worker if you're whole- if you're fully engaged. You're not just, like, told to go do a thing.so that's translated through my entire career and why today I really focus on just that. So I'm just coaching young adults.

I do have some mid-career clients, but what do you wanna do with your life? How are we gonna translate your major into a career? Or maybe you're in... You have a career, and you're, have that first job, but this ain't it. I don't like it. I wanna try something else. How do we help you find what that next thing is and start, you on that path to get that next job?

So that's, that's that full arc back to the, you know, maybe not the very beginning, but at least the early middle

[00:11:06] Meg: Yeah. Yeah, so arts to restaurants to restaurants and tech to, then we have marriage and motherhood, which throws a whole wrench into things, right? And then finally, you're, you're taking a look retrospectively through all of these transitions, this very non-linear path, right? And you notice, oh, hey, the thing that I have actually been doing and enjoyed the most throughout this whole thing has been coaching, and coach- like helping people figure, figure the next step out.

And I love this approach and that you apply it to young adults specifically because I think many people... I was, I was this person, right? I, I decided to go to grad school to solve this problem, which I do not recommend, by the way, to anybody listening. but when you are faced with this, oh, my God, this isn't what I thought it was gonna be.

What I chose is not really what I wanna do. The reality that I never could have known before had I not had this experience, has changed my mind, and I don't want to do this anymore. So I, I love that you are serving that segment, of the, of the market and really getting, getting to hear from the young adults who are going to be shaping our industries, right?

And, and helping them figure out something that's extremely important to them, which is, you know, their life trajectory, right?so woven in your story, you said something pretty often, which is that, "I took the leap." And inherent in taking this leap is risk, right? So I, I want to talk a little bit about risk.

So a lot of people, a lot of the women that are listening to this podcast would probably describe themselves as being risk-averse, right? They've built really stable careers, sometimes over decades, and when they think about taking a risk, maybe switching careers, maybe starting a business, maybe, you know, changing their lifestyle as they age, right? They think about their families, about their reputation, about their financial responsibilities, and the id- the idea of taking a risk is genuinely terrifying to them. Not because they're weak or they're, they're, afraid, but because the stakes are very, very real. So I think you have a different take on risk than a lot of people do.

So,you know, I've noticed that people tend to sort of treat it as a binary, like something's either safe and a sh- kind of a sure thing, or it's risky and dangerous. But how do you interpret risk?

[00:13:57] Kate: I think there's, there's two ways largely to think about risk. it- you know, there's a million ways to think about risk. There's two ways that I think about risk.one is like what, what is the risk? Is it, is it that, is it real financial straits? Like h- how big of a risk to your financials is this going to be, or is it just gonna make me a little less comfortable than I would like to be?

Is it a risk to your physical wellbeing?

[00:14:28] Meg: Mm-hmm.

[00:14:28] Kate: well let's talk about that. You know, like there, there's different types of, of, of risk in your life. I, when I think about job risk, I very, I'm a very tactical person, so I think about what are all the things that could happen? Like, what's the worst, what's the worst case scenario in all of these factors, in all of these areas?

And I, and I'll, I'll, I'm gonna pick on my move to New York. So what's the worst case scenario of moving to New York?you get mugged. Okay. Well, I was very intentional about where I lived so that, my parents wanted me to be in a building with a doorman, but I wanted to be in a neighborhood there were, where there were lots of people.

And so I picked a, an apartment above a pizzeria with a bunch of old Italian men who treated me like their daughter. It's like that's how I managed that risk. there's the risk that your job goes away and you have financial constraints. Well, that happened. Like, my worst case scenario of like, you're there and you lose your job, that literally happened.

What did I do? I moved home. I, I've told that story and that, the way of thinking about that risk so many times, I've told it to people that are worried about moving to LA, I've to- talked to parents about, "Oh, my daughter wants to move to New York." I'm thinking about a specific friend who was moving right after I'd gotten home, and her dad was so concerned and I was like, "Hey, the worst case scenario is that you move home, and I'm here talking to you and everything's fine."

[00:16:04] Meg: Mm-hmm.

[00:16:04] Kate: But like, the... So I think you have to think through all of the specifics of whatever scenario you're looking at and think, well, is that worst case scenario acceptable to me? Is the financial downside acceptable to me or not? Is it gonna put us in dire straits, or is it gonna mean that I like, have to pinch pennies for a little bit, or that I need to like, have a, a tighter budget around, you know, extra things we buy in the house?

It's, it's... I'm not saying that everybody should take an inordinate amount of risk. I'm saying that my risk tolerance is quite high because I have lived through some worst-case scenarios, and they really weren't that bad

[00:16:49] Meg: Mm-hmm. So those early kind of, I mean, let's call a spade a spade, right? The early failures in New York, by your definition at the time, right?

[00:17:01] Kate: Yeah, totally

[00:17:02] Meg: yeah. seems like those were actually really instrumental in developing your risk tolerance. So can you talk a little bit more about how those early experiences and, and kinda getting that really good...

You know, the, the business world, entrepreneurship world, they, they talk about failing fast and hard, right? so you, you wanna, you wanna fail fast so that you can learn from it and, and recoup. But how did those initial failures shape your evaluation of risk in those later situations, like moving to a new city with your not quite then husband, right?

Like, it's, you just started dating him, right? Yeah. Or any of the other risks that you've taken. How did that initial experience sort of shape those subsequent ones?

[00:17:52] Kate: Yeah. I mean, I moved to Denver. People were like, "You're crazy. You have a job that pays well," particularly for my age. I have an MBA. I own my house in Houston. Like, why are you picking up your life and moving across the country? And for me, the, the reward of adventure and choosing a partner and building a life together, even though the risk was medium-high that, like, maybe he actually isn't the right person, it's like, cool, I'll move back.

Like, like I'd already lived that, and so I was really comfortable with that risk. I think that, like, there's different parts of my life where I have been conditioned to things, conditioned to disappointment, conditioned to I'm gonna say shame, but shame's not the right word. I used to have a really, like, visceral fear of public speaking.

my first semester in business school was really, really painful. and, and in many classes you're actually, like, graded or it's part of your grade that you have to speak in every class. And so it was really, Oh, it was just, like, eating me away. And this was before I was in- diagnosed with anxiety and medicated, and, like, that's a whole different part of my life.

But, it's before I had any of that awareness. I had this professor that I'm still close with, who was, like, the biggest, baddest professor at UT, and I... Or at M- at McCombs at least, and he's known for being very challenging. If you use space fillers, whatnot, et cetera,when you're speaking in class and you have to speak in class every day, he's gonna get in your face and yell at you.

So this is my worst case scenario, is that, like, John is gonna get in my face and yell at me if I say, or, "Ah," which I did at the time. I still do. And, I was in the first... I was in the, I was in the th- day one of his class. I'm a fr- I'm a s- I'm a first year. It's primarily second years, so I'm already intimidated that there's people that are, you know, way ahead of me in school.

And I speak because I have to speak to, you know, at least get a B. And, I used a space filler, and he got in my face and he yelled at me.and I think I said the word, actually, I said the word whatnot, which I thought was a- allowed, and I re- learned it's not allowed. But he got in my face and yelled at me, and I lit- it literally changed my life and the way that I think about public speaking.

This was a worst case scenario in my mind, in my little mind of, like, terrified of public speaking, terrified of saying the wrong thing, of looking stupid in front of my peers. I got yelled at, and then I was never afraid to speak in his class again. And now I think that public speaking is one of my best skills because I was conditioned that, like, your, that fear is just- Unwarranted.

Just a conversation, you're just talking. But I, this is, you know, it's a very small example of like be- my risk tolerance is high because if I think about that worst-case scenario of public speaking, what are they gonna do? Laugh at you? What are they gonna do, get in your face and yell at you? Like, it's just not, it's just not that bad.

so the risk tolerance is, is high. I have more examples of different elements of risk tolerance, but, and I don't think I'm a very risky person day to day, but, I, I am not afraid of, of change because of these lived experiences

[00:21:35] Meg: Yeah, and I love this idea of kind of bookending it. So, what is the worst possible thing that could happen in my mind, right? And then kind of especially in your move with your, your now husband, like what is the potential reward that I get? And I think sometimes the people that I work with primarily, they've, they've been so good at what they've done for so long, and they've never really failed, right?

They've done, done it all the, the quote unquote right way. They've always landed on their feet. They've always made kind of the safe call. They are much, much, much more focused on risk mitigation than they are on the potential reward of something. And I think what opens up after you have failed, after you have gone through these experiences, is that both of those possibilities really open up for you.

You get to see them for how they actually are, right? And to your point of saying, you know, okay, so someone's gonna get in my face. In my tiny little mind, that was the worst thing that could happen. Of all the spectrum of horrible things that can happen, right, that was the worst thing, and it happened.

so what would you say to that woman who is, you know, maybe always made that safe choice? And how would you... First of all, the question leading into this is, is it necessary to build risk tolerance? And if it is, how can someone who's never failed before start to build it?

[00:23:13] Kate: Oh, it's a wonderful question. I need to think about that.I think if we think about... I'm gonna start by, like, introducing gray into failure, right? So it's not like succeed and fail is black and white.everybody has, like, a little imperfections in their life, and you're accepting those imperfections.

Like

Did you use all the groceries in your fridge? What is your risk tolerance for buying produce and it going bad? Do you have a high tolerance or a low tolerance for that? It's like, you know, as a very, very, simple example, but that's gray. You already have some tolerance for, like, are you gonna speed through the yellow light or are you gonna stop because it's yellow and you should?

Like, I don't know, I speed, but like I also have a high risk tolerance.but you know, you're already, you already accept some level of risk in your life. So if you can start identifying what you can accept and not accept, then you can think about pressure testing that and not thinking about it as absolutes, as success and failure

[00:24:27] Meg: Mm, mm-hmm. I really, really love that. And that, that is actually a perfect segue into my next set of questions, which is o- all around this idea of, yeah, as, as you said, introducing the idea of gray into the black and white. And, you said in our, our podcast planning call that you want to sunset the word failure, which I, I love that concept, I'm Team Sunset Failure, because there is something fundamental about failure that is really, really, really informative and helpful.

So I wanna, I wanna ask you your opinion of why the word itself, failure, actually kind of matters as a concept, and maybe what is, what is a better way to look at failure?

[00:25:21] Kate: Yeah, I think failure has all this, like, baked in perception and emotion around right and wrong.

[00:25:30] Meg: Mm-hmm.

[00:25:31] Kate: If you could, like, reframe it as like, I had a hypothesis. I'm such a nerd. I had a hypothesis, and my hypothesis failed, or like, it... I disproved my hypothesis. That- that's the right word. I disproved my hypothesis.

I had a hypothesis that I can run a mile in three minutes. No. Well, did I prove or disprove it? Did I fail? Well, like, I mean, that's not logical. Like, I am never gonna run a mile in three minutes. I just, like, don't want to. Also, I don't know that my phys- body physically can, I think for the actual barometer, but like, whatever.

Did I fail at that or did I, like, disprove that theory? And so if you, like, take this into, did I succeed or did I not meet my expectation or... And then what did I learn from that? You, like, I just don't think the concept of failure serves me. If I choose to come from a place of optimism, then I choose to try, and sometimes I don't get as far as I wanted to, but I'm still learning when I didn't get that far.

I also feel that, I feel very deeply, that you learn a lot more from things that don't go right than things that do go right. If it's all sunshines and kittens and rainbows, then, like, great, you're just gonna keep doing the same thing, but you might not know what actually is working to make those sunshine and kittens and rainbows.

But if it's a little gray, then there's something to go, like, root out,

[00:27:09] Meg: Mm-hmm.

[00:27:10] Kate: then- then to go fix it. So you learn. I also call it, when I was managing people, skinning your knee. You're never gonna become a better people manager until you skin your knee, until you offend somebody, until you, like, say the wrong thing in a meeting or you say something that, like, your counselee, like, doesn't quite respond to, and you're not gonna know how to do it right until you see yourself doing it wrong, or not doing it as well as you could.

So I don't wanna call it a failure, but, like, you skinned your knee. Great. Don't do that again. But you don't, you don't know not to do it until you do it wrong at some point, you know?

[00:27:49] Meg: Yeah. I l- and I love that, that concept and that phrase, skinning your knee, and it's, you know, I think I have very young children and, and this is how, like, from the very beginning, like this, they... No amount of me saying, "Don't do that," is going to stop them from doing that. But the first time they touch that hot stove, or the first time they, you know, get sprayed with the hose in the face when they've been messing with the buttons, right?

[00:28:17] Kate: Like, that is how you learn. That's, that's a great parlay back to risk tolerance, right? Like, you and I as mothers, we're gonna try our hardest to not let them get a third degree burn.

[00:28:27] Meg: Yes.

[00:28:27] Kate: But, like, if you're gonna touch the hot, like the slightly hot thing, like I kinda wanna let you touch it so that you learn not to do that thing.

[00:28:37] Meg: Mm-hmm.

[00:28:38] Kate: I'm gonna let you spray y- yourself in the face with the hose 'cause like my tolerance for your crying is like quite high.

Like I... It's fine. You need to learn not to do that. go punch... Don't, don't punch your sibling. Okay. But like when your sibling punches you back, like that's you learning not to punch your sibling. I'm gonna let it happen

[00:28:58] Meg: Yeah, yeah. And I, I think the motherhood perspective is a, is a really good kind of second chance to learn those lesson... Not the lessons themselves, but to learn the concept of, like, you know, these mini failures or skinning your knee. That, that is how, that is how we really, really learn. And I think in reflecting on our, our initial conversation, I was, I was thinking about it, like, okay, w- well we kind of...

There are really two sides of this debate. There are the people that are like, "Oh, no, failure's awesome, and you wanna do it because it gives you so much data, and it's so... You know, you could take that and make it into something better." Great. You also have the people, most normal people, who really hate failing.

It's really yucky feeling, right? And I think that one of the reasons failure, in quotation marks, is so uncomfortable for people is because of what they make it mean about them as a person. So a failure, an action that I take or I don't take, becomes I am a failure, right? So in that kind of lens of things, in the moment when something is going sideways, when you're skinning your knee, how do you stay in that sort of, like, hypothesis testing, data collection lane instead of spiraling into, you know, having a shame spiral into I am, I have become a failure?

[00:30:30] Kate: Yeah, that's a great question. I'm, like, pulling myself out of this, like, very personal story. I'm gonna say DoorDash taught me this, like, broad set of skills. DoorDash has a very practical way that they operate. they use this system called OKRs, objectives and key results. I- I've an objective to go make money.

I'm gonna make this much money next year, and my key result is that money, the revenue. And then you, like, break apart that into, like, where is the revenue coming from and yada, yada. Like, it becomes this big, like, spider web of dependencies. But they don't measure it quarterly, they measure it weekly, they measure it daily. You measure it, yeah, and so, like, there was a, there was a chart that I could pull up every morning and say, "What did my, what did I make yesterday?" Like, what did my department make? What did my team make? The, of my, like, nucleus of control, what did we do yesterday? And every Wednesday, we had to report it out.

And so every week I had, so there's 13 weeks in a quarter, I had to hit my quarterly numbers, and I had committed to I'm gonna make this every week, and I had to hit that number, and if I miss a number, I have to make it up at some point over the next 12 weeks

[00:31:46] Meg: Mm-hmm.

[00:31:47] Kate: to the end of the quarter. But because we had this high frequency of check-in, weekly, it also meant that, like, you weren't waiting until the very end and saying, "Oops, I missed it by 50%."

It's like, no, I knew I was missing. And so you have all these moments for micro corrections or big corrections. I had a project one year that was, like, it was- September 2019, and we were gonna miss the total year number by 2 million deliveries, and I had to go... I had 20 weeks to go find 2 million deliveries.

It was like, but like I had 20 weeks, and I reported out on it every week for 20 weeks on how, where I was gonna go find the extra 2 million deliveries. it's those micro movements that allowed you to know, like If you're making progress or not. And so I think about my own success or failure, not failure, success or like learning is the same way. If you're not tracking it and you look up, it's like, okay, well, you know, you had, you had the ability to track this more tightly. If my, if my family budget is going off track, I have the ability to know it on a weekly basis if we're going on track or off track, rather than looking up at the end of the year and going, "Oh, how are we gonna pay the tax bill?"

You know? Like, you h- you have control

[00:33:17] Meg: I love this, and I love the theme that's emerging here, which is like these are knowable things, right? Like, the data are knowable things. It's not... And I think a lot of times when we fear failure, when we fear anything really, it's, it's these big ambiguous concepts that don't have edges that are just like just I'm afraid of failing generally in that direction, so I'm not even gonna look at it really.

And, your advice so far has been like well, no. Like, spell it out, take the time to like actually define the edges of this problem. But we've heard a little bit about failure as a concept, and sunsetting the term because it really is kind of a useful little, little tool. But if we're talking about failure, we should also probably revisit success, right?

So what are some alternative dimensions of success, I guess, that maybe don't show up on our, on our revenue report or, you know, a resume? things that are actually successes in retrospect that you maybe wouldn't have counted them as successes 10 years ago.

[00:34:24] Kate: Oh, yeah. I mean, I'm living it right now. I walked away from a corporate job and, like, a steady salary, and, I have a lot of things going on in my life that are outside of my corporate world. Like, I've had some family health issues. I have two little children that are very young, like a two-year-old and a five-year-old, and the two-year-old is a gremlin of a thing.

Like, it's... Like, so my definition of success is not just that I hit my numbers at my, at work, right? Like, did I have a good day today is a point of success. Did my husband and I have time to, like, invest in our relationship this week? Did we,When I close my laptop at the end of the day and I lay down to bed, like, was that a good day or a bad day?

And I don't, I don't define it... I, of course, I don't define it in those binary terms, but, like, what it... I do take stock for, like, what I'm grateful for, what was good about the day, and I, you know, I don't want this to get religious, but I, like, ask for help for the things that, I'm struggling with.

[00:35:35] Meg: Mm-hmm.

[00:35:35] Kate: I have, like, an elderly dog that's sitting right here next to me and, like, you know, those are...

I have some... I've had some hard days because of this little, this little thing. But, I think that personal success, I think comes down to, like, having a pulse on your satisfaction with life, and some things you have control over and some things you don't have control over. But, like, you know, I... There's this, something called the serenity prayer.

God... Oh, I'm gonna screw this up. God grant me the ac- God grant me the serenity to accept the things I can change, and the things that I c- not the things that I can't, and the knowledge to know the difference.

[00:36:21] Meg: Yep. Mm-hmm

[00:36:22] Kate: Right. Gosh, I wish I could, like, recite that better. I used to know it really well. But, you know- I guess it goes back to choosing optimism. I try to choose optimism,

[00:36:33] Meg: Mm-hmm.

[00:36:34] Kate: which is also a DoorDash-ism that was, that was, like, a lived and breathed one. Choose optimism and have a plan is one of their, like, core mission and values.but I also think it translates really well to your life. Have a plan. Have a financial plan.

Have a plan for your kids' school, how to set them up for success for getting onto the bus in the morning. But also choose optimism that, like, you're gonna have a good day

[00:36:59] Meg: Yeah. Yeah. I love the idea of kind of that before bed recounting or like k- not, and, and not to say like, "Oh, today was a good day. Today was a bad day," but like kinda dissecting the elements of, of your day kind of plays into one of the big philosophies that I have in my coaching practice, which is those moments of gratitude, but the wins, right?

And I, in the clients that have Slack support, which is kind of where I provide the asynchronous support, I have a channel, and it's wins. And any, any win counts. And over time what happens is that you start to... Your brain does this really cool thing where you start to expect them. You start to notice them.

You start to, count things as wins that you might have been neutral about before or, might not have even noticed, and that is what your, what changes your daily lived experience, right? That, to me, is what transforms a really horrible day into something that I'm like, "Okay. Yeah, there were real bad elements of today.

I do not wish to repeat today. But these things happened, and I'm, I'm grateful for these things, and these were wins."and kinda to your point of, of the, the elements that you're grateful for, my husband and I have a, a practice every day since the day we got married that we say what we're grateful for, and it's evolved over time.

There are new components to it now as we're parents and, you know, our relationship has evolved. But it is such a grounding thing to always be able to come back to, you know, I am really glad that I, you know, I'm really grateful for my house. I am really grateful for that one moment of repair with my kid after I lost my ever-loving shit on them, right?

these are all things that can help your lived experience and, and I think ultimately make you more optimistic and more h- you know, happier frankly. And that's kinda, I don't know, it's kind of an unwritten goal for all of us, right? We want to enjoy our lived experience.

[00:39:18] Kate: Yeah. Yeah. I, I love that gratitude. I think, I, I think everybody needs to, like, you know, find something that is achievable and consistent for them. I like the idea of meditation. I, like, my brain is not a meditating brain. It's a high-strung ADHD brain. But my version of meditation is this, like, prayer at night, and, I feel like this is, like, very... feel weird that I'm gonna, like, put this on a podcast, but I'm gonna do it 'cause I think it's helpful to share. so I thank, first I thank God for my life, my love, my health, my happiness. Kind of like foundation, that this is, thank you for these things that make me, me. And then I thank him for my children, my husband, my dog.

And then I go into the, like, whatever. Sometimes it's that's it, and sometimes it's, like, thank you for these things that went well, help me with these things I need help with, give me grace. It's a lot of asking for grace on different things. But, like, I didn't really recognize that that was effectively a meditation until

[00:40:26] Meg: Hmm,

[00:40:26] Kate: recently, 'cause I, I've been saying this to myself for decades.

but I'm not, it's not me and anybody else. It's not performative. It's me in my head. After I've read, after I've scrolled, the lights are out, sound machine is on.

[00:40:45] Meg: Yes,

ma'am. 

[00:40:47] Kate: this is what I say to myself before I try to actually sleep. I also have a terrible time sleeping, so this is part of my, like, this is part of my rhythm.

and now it's like second nature. Just happens

[00:41:00] Meg: Mm-hmm. Yeah. Yeah, and I know a lot of people, myself included, who have tried the meditation thing, and calling it meditation and doing it like how the apps suggest that you do it does, does not work for me. Again, ADHD brains. but taking a morning walk in nature, absolutely I can do that. And that, it, it's the same effect.

May not be the same way to get there, but I think the outcome, the outcome is the same, so that sense of kind of quiet and peace that we're kind of all after, so. So, this has been a fantastic conversation, but I am, I'm wanting to tie a little bit of a bow on this. So for someone who is standing on the edge of a change, right, big change, small change, but is kind of paralyzed by the risk and, you know, is sort of trying to figure it out, what's the one thing you want her to walk away from this podcast conversation knowing?

[00:42:07] Kate: First, that you are smart, you are capable, and you can do hard things.

[00:42:11] Meg: Hmm.

[00:42:12] Kate: And once you believe that, say it to yourself, even if you don't believe it. You say it long enough, you'll start to believe it. Like, you can do hard things. And then think about, okay, what do I, what am I gonna get from this? What's the reward? And what's the worst that could happen

[00:42:33] Meg: I

[00:42:33] Kate: And if that worst is really un- is really un-, you know, then you can't handle it, then you can't handle it. And you don't have to take that risk. But if you can handle it, then maybe it's worth it

[00:42:45] Meg: Mm. I love that. I love that. data is knowable, right? So find your... Figure it out. Figure out your financial plan if you need to. Figure out what the, the true risk is of, of making that move across the country. all knowable things, so. Well, thank you for this conversation, but, I want to leave our audience with where people can find you.

How can they learn more from you? How can they get into your world?

[00:43:13] Kate: you can follow me on LinkedIn. KateCrane7 is my handle, and then, directionoverpe- perfection on Instagram and TikTok. And I've just launched a podcast. You can find it on Spotify and Apple Podcasts, Direction Over Perfection with Kate Crane

[00:43:31] Meg: Wonderful. Well, we definitely encourage everyone to check those out. And thank you so much, Kate, for your insight and your vulnerability today. Really, really wonderful conversation

[00:43:44] Kate: Thank you, Meg. It's been lovely

[00:43:46] Meg: And thank you for listening to Changeology. I'm Dr. McTurkano, and I'll see you in the next one