Transcript, E143: Reinventing Yourself

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For more on this episode of Hello Monday, check out this article featuring our thoughts on our 2022 theme, Reinvention.

This episode of Hello Monday, "Reinventing Yourself," first released on Jan 3, 2021.

Jessi Hempel: From the news team at LinkedIn, I'm Jessi Hempel and this is Hello Monday. It's our show about the changing nature of work and how that work is changing us. Happy New Year everyone. Over the past two years now, we've learned so much about how to adapt to changes that are just mostly beyond our control, but this year brings a new approach.

The pandemic hasn't gone anywhere, but things, they feel different. We're different. Sure, we can't control the future any better than we've ever been able to, but we've learned so much by this point about how to manage through ambiguity and this is the year that we choose change. It's the year of reinvention. This kind of change is at the very heart of Hello Monday. If you wanna have interesting that pays well over the long arch of your career, you have to be willing to take risks, to learn new ways of doing things, to reinvent yourself, and as you all know, I'm walking the walk here.

I spent two decades as a happily employed magazine writer at a media company and then, I gave it all up to make podcasts at a tech company. Different job, different medium, different industry, best thing I've done. But wow, was it scary at the time. This year, we're going deep on reinvention.

We're gonna bring you shows on people who made radical career changes, we're gonna talk to people who changed cultures and companies and people who changed their mindsets in ways they really didn't think possible. I'll look for people who have tools to make change easier or who's stories make us braver. And this year, I wanna hear even more from you, listeners.

As I was thinking about reinvention, I started to listen to past episodes. I do that sometimes to get inspiration, to figure out what I'm really thinking about. And so I wanted to start this year's conversation and that's really how I'm thinking about it, a year long conversation about reinvention by figuring out what the show has taught us so far. So here goes, first, change often starts with a feeling. You know this feeling, a nagging dull sensation that things just aren't quite right. Robin Arzon describes it well, Robin's the head instructor at Peloton. She's the person who reminds me every morning as I sweat through her class, you didn't wake up to give up but this kind of coaching, it's not what Robin started out doing.

Robin Arzon: Well, I find for ambitious people, it's actually pretty easy to find an intellectual pursuit that we find interesting even if the, the subject matter is dry. So, I did, uh, I was a corporate litigator, I worked with a lot of SEC stuff, this was at the height of subprime, so it was a very tense time in the market and I was able to focus and adapt and just dig in and I think intellectual folks often find that it's, it's maybe not easy, but it's simple to just dig in. But that doesn't mean that it's actually aligning with our, with our values and our goals and with a happiness quotient that is something that I discovered when I was leading a divorced existence between athletics and law.

So, what I liked about law, I worked with brilliant partners, I learned about business, I think, through osmosis. I would not have viewed fitness as a business and myself, frankly as a brand, as a burgeoning brand then, um, had I not worked in corporate litigation.

But I also knew that there was something palpably missing when I would count down the hours in my day until I could go for a 30 minute run in Central Park, so that divorced existence was not satisfying.

Jessi Hempel: And that running piece, I was surprised to discover that you actually hadn't grown up. You, if you had loved law at 10, you did not love running at 10, right?

Robin Arzon: (laughs) No, I, I wa- I was allergic to exercise wa- actually into, into adulthood. I was the, I was the arts and crafts and straight A student. I did not identify as an athlete, I was petrified of gym class. I actually was made fun of for the way I ran when I was a kid so I think that that, that stuck in my brain early as something that I didn't do, and I had to really recreate myself and start to write a different story once I realized that I was curious about what this running thing was. (laughs)

Jessi Hempel: How did you come to running?

Robin Arzon: Frankly, it was really through trauma. I was in law school and the prior year in my senior year at NYU, I was held at gun point in New York City and that experience understandably stayed with me. A year later when I was in law school I realized, wow, I guess I didn't really deal with as much of this as I thought I had and I have no idea why, but I was drawn to a pair of shoes that were in the back of my closet collecting dust and I decided to jog to class one day instead of ta- you know, drive the mile and a half and that is wa- that is really where my journey started.

Jessi Hempel: Wow, and from a mile and a half, you've moved onto 50 miles and above. (laughs)

Robin Arzon: (laughs) Yes. Ultra marathon territory.

Jessi Hempel: So during your, the remainder of your path through school and during the beginning years of your law practice, fitness was increasingly important to you. Wa- when and how did the way that you feel about it really start to change?

Robin Arzon: It was a slow burn, I would say because they ran in parallel tracks, you know, no pun intended where I really was still at the nascency of my law career and feeling like what's more? And I, and while I was falling in lo- falling in love with running, I was also getting curious about what's it like to be in house? What's it like to be, to practice different areas of law? You know, I dabbled in trademarks, I had IP stuff, so I was still kind of just trying to see if I could make the passion I found in the run something that I could find in my day to day law practice.

Robin Arzon: And because I was so new, having practiced only a few years, I thought there's gotta be something out there that I haven't considered. Um, and it was in that search actually that I started to realize if I uncheck all the boxes of what folks say you could do, uh, in journalism or using the written word or storytelling within wellness, which is really where my mind was going, I thought maybe I can create a career, um, that hasn't really happened before.

Jessi Hempel: That was 18 months before Robin joined Peloton, and I love the way she describes this. She didn't know exactly what she wanted to do. She made it up as she went along because Robin's job, like a lot of jobs, it didn't really exist before a few years ago. How would you even describe it? Like fitness instructor slash entertainer slash social media influencer, it's kind of hard to slot into a traditional resume. Robin literally designed the role herself and that's what many of us aspire to do.

Jessi Hempel: So how exactly do we do it? Dave Evans and Bill Burnett have some helpful thoughts on this. They're designers and they teach one of the most popular courses at Stanford. It's called Designing Your Life and now it's a book, too. Here's the big idea, Dave speaks first.

Dave Evans: The way I describe it, the way we describe it at the D school, it's a bunch of different ways of solving problems, different ways of thinking. And what a lot of people are trying to do is kind of engineer their life, engineering thinking is I've got the, I've got all the data and I've got the equations, I can build this bridge, I can, I can solve this problem, there's a right answer. But you know, the problem with life is, it's an emerging reality so what's gonna happen six months from now, a year from now, you don't know. I don't know. There's no way to predict that.

Bill Burnett: I, I tell my students you only have two choices 'cause the future's coming.

Jessi Hempel: Right.

Bill Burnett: So you can accept the default thing and just kind of try to react to it, or as Dave said, you can imagine it as a giant design problem or an improv problem. There's always something that you can design into and so it's a, uh, inherently optimistic way of thinking about well change is change, it's gonna happen, but I have some, I have some power over how that change impacts me and what I take advantage of when I move into that future.

Dave Evans: So design thinking is an innovation methodology, uh, to invent things that have not been invented before and we don't know what they are until we find them, by using ideation and prototype iteration. So if you want the whole thing in a nut shell and I'm in the car and I'm at a stop light, okay, what do I need to do? Get curious, talk to people, try stuff, and tell your story.

Now, we gotta unpack that, but if you double click on each of those you get some, some feedback, but that's it. Get curious, talk to people, try stuff, tell your story. 10 words, that's really what we mean.

Jessi Hempel: Well, I love that framing so much because I may not have the language that you have to describe it, but that has been what I have figured out in the first 40 some odd years of my life-

Dave Evans: Good job.

Jessi Hempel: About how I learn new things-

Dave Evans: (laughs)

Jessi Hempel: About myself, right? Ma- maybe if I had gotten your framework when I was 20, I would have figured that out a lot earlier, I don't know. But I love that you ground this. The first thing that you ask people to do is to accept where they are.

Dave Evans: Right.

Bill Burnett: Yeah, step, we call it step zero. (laughs) Um, design only works in one place, reality. There's magical thinking stuff, you know, should is in your head. The only place should exists is in your head. Most people's definition of how happy they are, coming back to happiness is what is the current referendum gap between what's going on in the real world and what I had in mind. If that gap is large, how's it going? Poorly. If that gap is small, how's it going? Well. So I guess the entire definition of my state of being as a human being on the surface of the earth is defined by some stuff I just made up.

Bill Burnett: So we don't start with that. We start with reality. Like what's actually going on and where can we get to from here? So we're reality based.

Jessi Hempel: Well, so let's talk about change a second.

Bill Burnett: Okay.

Jessi Hempel: I recently was at an event with Adam Grant and we were talking about various ways that you can be better at your job and-

Bill Burnett: Mm-hmm (affirmative).

Jessi Hempel: And I asked do you, do you think people can change? Uh, do you take your own advice? 'Cause I don't take my own advice.

Bill Burnett: (laughs)

Jessi Hempel: It's very hard. Um, which is why your idea, which is that it's about the little incremental change-

Bill Burnett: Yeah.

Jessi Hempel: That you can make and celebrate kind of makes sense.

Dave Evans: Yeah, well first of all, Adam's a great guy, we think his stuff is cool.

Jessi Hempel: He is great.

Dave Evans: Um, and yeah, and he, and he's kind of part of the design, you know, the, the inner design mafia, I guess. There's (laughs) a lot of research on how you actually make change in your life, either getting rid of a bad habit, I wanna stop smoking or doing so- you know, something, or adding a new habit, I wanna eat healthier or I wanna, you know, practice mindfulness. And all of the research says it... you fail because you take too big a step and then when you can't re- recognize that as dir- moving in the direction of the thing you want, you say well, I di- I couldn't do it and you quit. So the-

Bill Burnett: You just taught yourself to disempower yourself. [crosstalk 00:10:20] You just proved you can't do it.

Jessi Hempel: I am so good at proving that I can't do things, you guys.

Dave Evans:Yeah, yeah, yeah.

Bill Burnett: It's all about, you know, you pick a goal but you make really, really small incremental steps. So we call it the "set the bar low" method. Like just set the bar low and clear it. You'll feel a little piece of accomplishment, you got a little blast of endorphins in your brain, then do it again, then do it again. So you don't change your job by, you know, screaming and yelling at your boss and, and throwing your, you know, your, uh, idea on the floor and then walking out, storming past the guards. You take a, you assess where you are, you take a couple of small steps, you prototype your way into things. By the way, a lot of times people want stuff, and when they get it, they find out, ah, it wasn't what I thought it would be. [crosstalk 00:11:01]

Jessi Hempel: That's the funny thing about desires, right?

Bill Burnett: Not what they had in mind.

Dave Evans: Yeah, yeah.

Bill Burnett: 'Cause you... not what I had in mind. [crosstalk 00:11:04] 'Cause nobody, nobody tried it first, so prototyping is just a way of sneaking up in the future and seeing if it's really gonna be what you think it is and when you adopt these mindsets, like first of all, I start with curiosity 'cause I don't know what the future's gonna be, so what am I trying to analyze anyway? I got no data. I gotta go talk to people, I've got to try little experiments called prototypes and I can pretty quickly find a method for finding my way forward in this kind of fog of uncertainty and more often than not, design and invent something that's really cool and you can invent something really cool called your next job, your next life, your next thing.

And if it's true that we're gonna live to be 100 and we're gonna have to get really good at this because yes, the robots are coming and AI's coming and we're gonna have to reinvent our job anyway, but the good news is don't you, don't you hope there's a really cool job that hasn't been invent yet that you're gonna be doing 10 years form now, that'll be even cooler than what you're doing?

Jessi Hempel: Dave and Bill have each had so many chapters personally and they plan to have a few more. We're gonna take a quick break here. Coming up, we'll talk about what's in our control and what's not.

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Now back to our show. The last two years have taught us that we can't control very much about what's going on around us. You can do all the right things, you can put everything in place to change, but then you have to trust the process here, too. That's a big part of reinvention. Here I think about talking to Glennon Doyle, the writer and activist in the spring of 2020. It was right after her book Untamed had come out and before it had become a global phenomenon.

Jessi Hempel: Now, if you follow Glennon, you know that things worked out pretty well for her professionally. Her book was on the New York Times bestseller's list for more than a year. She launched a popular podcast, but when I spoke to her, none of this had happened yet. I'd attended the first stop at her book tour at a church in Brooklyn. It turned out that it was the only stop. She'd had to cancel the tour.

Glennon Doyle: The tour being canceled was one thing. That wasn't the biggest thing. I mean, Amazon is not shipping books right now.

Jessi Hempel: Oh my gosh, you know what, I really did not think about that.

Glennon Doyle: Yesterday morning I was on the phone with my team and they were crying. Like, these are grown, badass women. The, the trauma that people are in right now and then trying to keep their jobs going, so we'll spend, you know, a week like okay, so how can we keep getting this message out online? Right? We can keep this going online and then wake up and Amazon's not shipping. Like-

Jessi Hempel: Yeah.

Glennon Doyle: Wa- (laughs).

Jessi Hempel: Yeah.

Glennon Doyle: I can't apparently beat a global pandemic. There is a moment where you just realize okay, what I have known deeply for the last week is I have to stop caring about my book for a little while. Like I will... I love it so much, I believe it has a destiny, I believe it will help people, but right now what my community needs from me is for me to show up and just be a voice of comfort and safety and hope. So that's what I'm doing.

I think that everybody who is doing any sort of project in the world right now realizes that, that what's happening right now, it's causing this huge shift where everything is falling away, all of our plans, all of that stuff and it's just like okay, how can we show up for each other right now? Not our product, not our whatever, like how can we really connect and get people through the trauma of this?

What, if you do the next true, the next right thing, eventually it all comes right.

Jessi Hempel: I've held onto this idea and maybe it's because I've also watched a lot of Frozen Two with my toddler recently. I can kind of hear Kristen Bell sing it in my head, it's an elegant directive, do the next right thing.

Jessi Hempel: Especially in times when there's so much ambiguity that it's tough to have much long term vision. It feels like none of the rules apply anymore. Every rule that I thought was static and unbreakable, even my most creative self could not challenge, uh, it doesn't apply anymore, so that leaves us to figure out how to listen to ourselves because that is the only way that we're going to have any order, the only order is gonna come from within and that's an uncomfortable place to be.

Glennon Doyle: Yeah, and also such an opportunity, right? I mean, I do think that's weird because the main message of the book and the main message of my life has been okay, we have been trained to look outside of ourselves for, um, expectations about how we're supposed to create the life we create and the family that we create and the relationships that we create and the companies we create and the governments we create, all of it, right? But I think that this part of my life is teaching me that it didn't work for me. I did all those things right, I was a good girl and I was a good woman and I was a good Christian and I was a good wife and I was a good mother and I was fricking miserable.

So, um, it, it took me a while to figure out that all those goods... it's okay to wanna be a good everything. You just have to define what good is for yourself, right? Because if you're defaulting to somebody else's idea of what's good, then it's always gonna be a cultural idea of what's good and for women, it is always gonna be, in one way or another, disappear, be quiet, get smaller, stop making us uncomfortable. However you define like the expectation would be one version of that.

And the only way to let go of those expectations and ideals is to go within, right? Because everything, all the messages we get outside of what to do, they're not pure. They're not from us. They're created by people who are trying to control us so the only way though to do that is to get still, right? Is to start to block out all the other voices and do the, the difficult but simple work of going inside and being quiet and listening for that nudge and that knowing and that voice.

Jessi Hempel: When it comes to listening to your own voice, my favorite Hello Monday guest has definitely been Debbie Millman because sometimes that voice tells you what you should have done or where it thinks you should be, but sometimes, sometimes you can free yourself of the shoulds and really, truly, hear yourself. Some people would say this takes confidence. Debbie disagrees and she also has an exercise for us. It's one that I wanna leave you with as we start the year again.

Debbie Millman: I think going back to the whole notion of confidence, and this is something I really learned from, from Dani Shapiro, the writer. She had come to do an episode with me at my studio at the School of Visual Arts and after the interview, she saw a stack of books about confidence on my desk in my office. At that time in my life I was thinking that confidence was the holy grail. (laughs) And so they were a whole slue of books that had come out and she saw the books and she said, "Oh, I think that confidence is really over rated." And as somebody that was seeking confidence as if it were the holy grail, I was sort of taken aback and shocked and when I asked her to elaborate, she felt that, she, she stated that she felt that ultimately, confidence was something that only came after courage. That it was much more important to have courage to take that first step into the unknown than to be able to just manifest confidence through some sort of motivational inner language.

Um, and so I, I do feel that that's true, that, that courage to take a step into the unknown is, is really the birthplace of creativity.

Jessi Hempel: Yeah, you know, I hear from a lot of listeners who they have a day job and it's a day job that pays the bills and it's fine. But they also have a more creative aspiration and they've kind of created a, a mental picture, as it were in which those two things have to be separate, and they see the limits. They see the limits of their own abilities and capabilities and, and this goes to the courage piece.

I thought a lot about in your interview with Tim Farriss, toward the end of the interview, you talked about Milton Glaser and an exercise that he had done with you and that you subsequently do with your students. Do you know what exercise I'm talking about?

Debbie Millman: The 10 year plan.

Jessi Hempel: The 10 year plan. I feel like our listeners need the 10 year plan-

Debbie Millman: (laughs)

Jessi Hempel: So I wonder if you can, if you can describe it?

Debbie Millman: Well the 10 year plan is an exercise that I've borrowed from Milton Glaser, um, and it was something that I actually undertook back in 2005. In 2005, I was, uh, still working at Sterling Brands, which is a company that I worked at for over 20 years and helped grow and helped sell and that was a huge, huge part of my life for a very long time. Um, and in 2005 I took a summer intensive with Milton Glaser at the School of Visual Arts, and it was really catered to mid level professionals, people that were, that were seasoned, um, but not so seasoned that they, they didn't need to be taught anything anymore.

And, um, I took it and it really changed my life. One of the exercises was to envision and write out how you could imagine your life to be five years into the future if you were doing exactly what you wanted to be doing. Like every single thing, from morning to night, you were instructed to write out every detail, to make it as detailed as possible.

And, and I, I'm, I'm a student that loves to learn. I'm the kind of person that really, um, commits to assignments and so I really put a lot of energy into this and he, he asked us to do that and said that in the 50 years that he'd been teaching at that point in his life, this was the most important class that he taught and he was constantly hearing from students from decades prior who had also undertaken this exercise and had had miraculous results and he said it was a very magical little exercise. He really urged us to put our whole hearts and souls into it, which I did.

And, um, we had to share them at the end of the, of the intensive, and it was a moment of really declaring what you wanted your life to be in the future and then lo and behold, and I made a list, let me tell you, I made a list, not only did I write an essay, which I put my whole heart and soul into, I also then made a list. Like I wanted it to be super clear. (laughs) These are the things that I want my life to be about in five years, in 2010.

And so they were big, audacious goals. Things that I didn't really think were possible but wanted with my whole heart. And lo and behold, over the years, year one, year two, year three, year four, year five, things really started to manifest. Um, they really started to manifest in momentum about seven years later. Um, and then even most recently, and it was 15 years later, one of the, one of the last remaining items on the list, um, manifested. And so, I decided and, and Milton allowed me to do this when he stopped teaching, to incorporate this into my curriculum.

But because my students were younger than the average age of Milton's classes, students in his classes, um, I decided to make it a 10 year plan, also, because I had lived through this process-

Jessi Hempel: (laughs)

Debbie Millman: I do think that it takes time. I think anything worthwhile takes time and that given that it's now taken my 15 years to manifest all of them, that I want to give students a little bit more runway. Um, and so I made it a 10 year plan and I've been teaching it now for about 10 years and I am always astounded, like Milton, when I get emails from my students or I see them and they tell me things that have manifested in their lives.

So I think there's something about envisioning and declaring what you want that is indeed very, very pa- very, very powerful. I mean, I do think it's a little bit of magic, too, but I do think it's mostly about articulating and declaring what you feel you're worthy of being able to achieve.

Jessi Hempel: So I love this, Debbie and, and I will confess, I have done this exercise.

Debbie Millman: Oh good.

Jessi Hempel: I did this exercise with a career coach about, mm, about five years ago actually and, and there's a reason why I asked you to describe this in connection with courage. Because first of all, um, I think that the real courage to do anything that we might wanna do is to take that first step to envision it. And at least when I did the exercise, I don't know if it was like this for you or for your students, my first pass was kind of bland. It was, it was moderated by what I thought that I could probably do. So you know what I wanna do? I wanna write a book. Well, I'm gonna dial that back. I wa- I wanna write an article. Like-

Debbie Millman: (laughs)

Jessi Hempel: I'm gonna write an article, right?

Debbie Millman: Yeah.

Jessi Hempel: And, and it took a lot of pushing and a lot of, uh, discomfort to get to the point where I put aside everything that I thought that I was capable of, listened to my internal compass and just wrote down every single thing that I wanted, even if I didn't think that it existed right away. And then that second part happened, which you called magic, I'm gonna call it magic, too. And maybe it's magic that we ourselves create, but when you actually get it all down on paper, it kind of happens.

Debbie Millman: Yeah, I don't exactly know how it happens. It seems to happen for a lot of people. I, I put so much energy into the first go around that I didn't need to rewrite it, but because I allow my students to rewrite it if they feel once they've heard others, that they haven't really reached for everything that they wanted, to rewrite it, and I would say a good number actually end up doing that.

I ended up rewriting the... or redoing the exercise. I wouldn't say I was rewriting it, but in 2017, I rewrote the essay and in, in, in as... to address the current times and the next stage of my life and it's funny because a lot of people would say, oh, have you written another one because that one was so long ago? At that point it was 13 years ago and I kept saying, "Oh, I really want to, I really want to." But something was holding me back and I had decided that I wanted to do it in 2017 and literally I did it on December 31, 2017. Like I wouldn't make any New Years Eve plans that year-

Jessi Hempel: (laughs)

Debbie Millman: Because I had had this goal, I hadn't achieved it and I needed to sit down and get it done. And I did and I also put some very audacious goals in that and a few of them have manifested. So yeah, it's, there's something really wonderful about it.

When, when I did the episode with Tim, one of his listeners went and transcribed the way I described the instructions and created a website called yourtenyearplan.com and, and it's there for anybody that wants to follow the instructions.

Jessi Hempel: That's pretty rad.

Debbie Millman: (laughs) [crosstalk 00:26:49]-

Debbie Millman: So I was so excited about it.

Jessi Hempel: So cool.

Debbie Millman: I'm like wow, look what somebody did.

Jessi Hempel: That's where reinvention begins. We have to decide what we want. This is harder than you think. It takes imagination and the will to let go, first of all, of the constraints we put on ourselves. So many of you are in the process of doing this right now, so let's start the year by talking about it together. Join us for Office Hours this Wednesday afternoon at 3:00 pm Eastern. We'll go live from the LinkedIn news page, or tell us what you think. Email us a voice memo at [email protected]. We really love hearing from you.

Just before the holidays, Andrew Hunt sent a note from his morning walk. You can hear the leaves rustling under his feet. He'd just listened to a couple of early episodes of the show, all about where our best ides come from and he shared his own process about where his best ideas come from.

Andrew Hunt: I get my ideas from living through an attempt at solving a problem. That's pretty much always the mechanism by which an idea occurs to me, I either change the solution or I realize that the reason I'm dissatisfied is that the solution, though a good one, does not address the actual problem, which was not, at first, apparent.

Jessi Hempel: Andrew, I liked this description of problem solving because that's my style as well. I need to see something in order to change it, to fix it, to find a new idea in it. And listeners, if you have thoughts, things you want me to explore about reinvention, thoughts on your own 10 year plan, please send us your voice memos to [email protected].

Hello Monday is a production of LinkedIn. The show is produced by Sarah Storm with help from Taisha Henry. Joe DiGiorgi mixed our show. Florencia Iriondo is head of original audio and video. Dave Pond is our technical director. Michaela Greer and Victoria Taylor reinvent this show constantly. Our music was composed just for us by the mysterious Breakmaster Cylinder. Dan Roth is the editor in chief of LinkedIn. I'm Jessi Hempel, we're back next Monday, thanks for listening.