Navigating Transitions in Unpredictable Times with Erica Williams Simon

Celeste Headlee:
So Erica, this month we’re focusing on career choices and transitions. And at this point in our nation, a lot of people are having to make career choices that they didn’t want to make or they’re being forced to have a transition in their career instead of choosing it and planning for it. And I wonder if the strategy changes when these kinds of changes occur because they have to, as opposed to when you want them to.

Erica Williams Simon:
Yeah, that’s a great question. I think we’re in a moment when folks are thinking about whether because of economic necessity, professional necessity or just some sort of overwhelming feeling that things need to change in their lives. Folks are feeling this unexpected pressure to make change happen really quickly. And I do think that there’s a slight difference. The obvious difference is that sometimes you’re pushed into these moments of transition that you weren’t seeking. But I think the decision making process about what that change looks like is actually the same. Because regardless of how you arrive at that moment of transition or moment of pivoting, once you’re there, you then have the power to determine the direction. You have the power to determine, aligned with both your needs, your material needs, but also your values, your passions, your desires, your vision for your life.

What do I do with the circumstances that are around me now that can point me in the direction that I want to go? And so I think it’s the real change, the real difference between this type of transition and one initiated by your own desires is just in how you approach it. It’s an attitude. You’re going to have that moment of perhaps learning if the life that you thought you were living no longer exists, there’s a moment for grief, you’re allowed that. There’s a moment to recognize that you weren’t expecting to have to make a shift here. But once you get there, however you get there, you still have that power to determine the next step.

Celeste Headlee:
So this is something that you did at a very young age at age 27, and made it a real pivot in your career. First can you tell us a little bit more about what brought you to that career choice, and what preparation you did before walking away from your career?

Erica Williams Simon:
Sure, yes. So I started out my career, I’m a Washington DC area native and I started out my career like I think most people in their twenties certainly in the millennials generation, but I don’t know that that’s unique to us. I think a lot of folks who are young start off with wide-eyed wanting to change the world. And so I naturally, thanks to a job that a great professor hooked me up with, I found myself right after college working in one of the nation’s leading civil and human rights coalitions. I was in a meeting with Jesse Jackson, I was in a meeting with Bill Clinton. I was exposed to this high level in the world of advocacy and immediately took to it like a fish to water because it took advantage of my skillset.

It was mission-driven, which as a preacher’s kid is very, very important to me that anything that I do align with my values. And so I was well on my way and through both grit and skill, but also I think luck and who I was around, I ended up in a really high profile position very early in my career. And so during the 2008 elections, I was on national television, I was a commentator on real time with Bill Maher. I was the voice of millennial civic engagement and was running a multimillion dollar program inside the nation’s leading progressive think tank, working with Clinton’s chief of staff. All these fancy things that look really great on Instagram and made my resume really flashy. But the truth of the matter is, I wasn’t happy. And I use the word happiness cautiously because happy sounds very frivolous.

It was a type of discontent that comes when there’s something within you that is misaligned with the life that you’re living. And so while on the surface it seemed like it was great and I was on all the 30 under 30 lists and everything was going well, I wasn’t really taking advantage of who I am, which is a deeply creative person, which is a deeply spiritual person. I now talk about myself as someone who is not an indoor or house cat. I need to be outside, I need to be moving around. I don’t like to be confined within one institution. Also economically, although I say in my book, I joke that in DC, in Washington, they don’t pay you in dollars, they pay you in awards, which you can’t then turn and pay your rent with. So while my career looks amazing, I was still pretty financially insecure as many, many young people are.

So all of those things contributed to the sense that, okay, perhaps this isn’t the right career for me. And I wish I could say that at the time I made this beautiful strategic color-coded plan where I would leave my career and the next six months and I would explore and figure out next steps. That’s not what happened. I got married, came back from my honeymoon, was so frustrated by my job and my boss and just some circumstances that felt out of my control and I had my Eat, Pray, Love, Jerry McGuire, I’m walking away from it all moment. And I just abruptly quit, which I don’t recommend. I don’t encourage people to do that. But the process that I then underwent after that abrupt walking away is what I write about in my book and what I tell people to do.

And really it involves figuring out, first of all, how did I a driven, ambitious, deeply soulful, mission aligned person end up so quickly in my career at a place where I felt like this isn’t right for me. And that involved unpacking all of the stories that I had told myself or that I had believed that had shaped my understanding of who I was, what work was and should look like, the perception that I was showing the world, my stories about money and success. And then painstakingly one by one, rewriting them and taking control of my narrative to help lead me towards the future that I actually wanted for myself.

Celeste Headlee:
And the book you’re talking about is from 2019 it’s called “You Deserve the Truth: Change the Stories that Shaped Your World and Build a World-Changing Life.” I wonder, how do we know the difference between jobs that we’re good at and jobs we will enjoy?

Erica Williams Simon:
So many of my childhood references were preachers because I was a preacher’s kid and I once heard a preacher define… He talked about purpose in this way. He was pointing to a big floor speaker like the speaker that sound comes out of, at a conference or in a large room. And he said, “You know what? This speaker can function as a chair. It’s sturdy, it’s big. I can sit on it. But just because I’m sitting on that speaker doesn’t mean that it is actually doing what it was designed to do. There is something greater that it can do and serve and be in the world.” And that’s what purpose is. Purpose is not a function, but it is using something at its highest and best use. And so when I think of how we navigate our careers, so often we’re led by function. What is it that I can do and am capable of and I’m even good at doing? And we don’t know until we try. And I encourage a lot of experimentation. That’s okay. You don’t have to have it all figured out at once.

But once you start trying certain things and realizing, okay, that this skill set is something that I have. But how does it make me feel when I use it? What am I seeking? What validation does it bring me? What is the impact? Does the impact match up with my vision for my life? Really the skill that I’m encouraging folks to use to unpack all of this stuff is questioning. The book is organized in a couple of core main questions to ask yourself as you’re looking at not just your career but your life to figure out if it is what you want it to be. And so as you’re utilizing these skills and looking at jobs that may take advantage of them, you have to interrogate and constantly ask, how is it making me feel? What am I gaining from it? What am I seeking? And I think you don’t know until you both do, and also begin to really know yourself. And that’s something that takes time.

Celeste Headlee:
And I really would like to unpack that a little bit because it’s something you talk about pretty eloquently. But I think also there’s this idea that you can figure out your ideal job by talking about it. [Crosstalk 00:09:09] By talking about your friends or by looking at the jobs other people have and seeing what other people doing and saying, I would love that job. And you laughed. And I wonder, why doesn’t that work?

Erica Williams Simon:
It doesn’t work because you don’t know what you don’t know, right? You don’t know when you’re looking at what you presume to be or assume to be a dream job, what that actually is, what it feels like, what the sacrifices are, what the costs are. What you see generally when you’re looking at dream jobs and other people is the highlight reel. You see the Instagram feed, you see the fast company article about successes. You don’t see the behind the scenes, and you don’t know the person. You don’t know their motivation, their dreams, their desires, what matters to them. Key-worded values. You don’t know what they value. And so what I’ve learned just again in life is that experience is the best teacher. That does not mean you have to go out and get 50 jobs, right? You still use wisdom. You still take advantage of all the inputs that you have about your skillsets, your education, what you enjoy. But there’s some things you won’t learn until you do. And so I encourage a spirit of experimentation, or if you’re a Disney fan and you’ve seen Moana, the idea of way-finding.

That you’re not going to have a clear… Particularly in this economy and in this world, and I think we’re seeing that right now with the pandemic, nothing is guaranteed. There is no yellow brick road anymore, if there ever was one. And so the idea that you can talk and plan and think your way into your dream life is just unrealistic because the world is so unpredictable. What you have to do is take steps and then put your finger up, check the wind like Moana did, and see what’s happening and how am I feeling and where am I going. And constantly making little pivot and evaluating the realities and gaining what you can along the way. And I think that’s how you end up in the life that you want, which ultimately, and this is the mind blowing part for me, it may be different than what you think you want today. You only gain that perspective and that insight into what a new dream for yourself could be by living, by experimenting, and by doing.

Celeste Headlee:
So we’re going to talk a little bit about your advice to be story smart, but I wanted to talk just a little more about this pandemic. Because I wonder, understanding that this is a very tough time for a lot of people, obviously there are people suffering and clearly we are losing a lot of people. However, is it possible for those of us who come through the other end of the crisis, that this is an opportunity to think about exactly what you’re describing? To imagine a completely different life for yourself? I mean, just because the way-finding, people may have been on the same path that’s leading them in a direction for 10 years and maybe this is a moment to step off.

Erica Williams Simon:
Absolutely. Like you, you always have to caveat by saying these are difficult, difficult times. And I’m not the kind of person that says, “Oh, this happened because, or this happened so that something positive could happen.” I don’t believe that. So instead of opportunity, I like to say crisis creates space. And you can use that space however you choose. And I think that this crisis has created the largest amount of space I’ve ever seen in my lifetime for that kind of rethinking and re-imagining. I’m seeing people are re-imagining again, certainly what their work life looks like, but also what their work life balance looks like, if you believe in that phrase.

Also what their relationships look like, what matters most to them, their relationship with technology. I mean this is a time when you really can rethink everything that matters to you and the design of your life. And so as it pertains to your career, like we said in the beginning of this conversation, some shifts are going to happen whether you want them to or not. The economy is going to be radically different when we all go back to work. Some of the jobs won’t even be there anymore. Some jobs will have changed, so that is just a fact. But regardless of whether what was before remains, this is an opportunity and a moment where we can think about how do we want to live when we come out of this? Do we want to live the exact same life we were living before? And the answer to some may be, you know what, yes. I liked the way my life was.

But for those who are looking and saying, I’ve always wanted to X, Y, or Z, or I didn’t know what was wrong, but I knew something didn’t feel right. This is the time to explore. This is the time to ask yourself the tough questions and to face the future. And it’s a good way to also face the future less with fear, which I think is something that is… This is a scary time. There can be a lot of anxiety about not knowing what tomorrow holds. And so I think using this as a moment to reimagine and to dream and to plan for something new is a way to balance that fear and anxiety with hope.

Celeste Headlee:
So let’s say that our listener has absolutely agreed with what you’ve said so far and they are ready to be smart about their story, so you’re stories smart. What is the first couple things they need to do to get started?

Erica Williams Simon:
The first thing is find out what you have believed. I always say you got to understand where you are and where you come from before you can figure out where you’re going. And so take the time to look at the pieces of your life that you’re trying to change. So in this case your career, and really ask yourself, okay, what are the things that I believe to be true about myself, about my value, about work, about my talent? Literally take a notebook and start writing these things down. What do I believe my talents and skills are? What do I believe I am good at doing? What do I believe about money, and my role as a provider? Ask yourself these questions so that you can begin to assess, okay, what shaped where I am? Because only when you do that, can you then decide, okay, which of these things need to change? Are those true? Do they align with what I actually believe to be true now at this stage in my life, and what do I want to change around that?

So first it’s getting on a notebook and just doing some good old self interrogation and figuring out what stories you have believed up until this point. Then ask yourself the question, once you’ve got that list, do these serve me? Have they served me? How they made me feel? Does believing that success is tied to my income, how has that worked out for me? How do I feel? You got to make an assessment, good or bad, has it worked for you? Once you’ve done that, then the fun part is, so what could a new life look like for me? And this is where I find in conversation, most people get stuck. They say, “Okay, I’m clear that I believe these things and they came from school or they came from my parents and I came from media. I’m clear on all of that, but I’m not clear on what to do after that point.” And so that’s where I say you can have some fun. You can start reading and start exploring looking at different career paths. Even though we just said, you can’t fully know until you do it yourself.

You can do some research, you don’t have to jump out there blind. You can start looking around at the women that you admire, the careers that you might not have even known existed and getting as much information, collecting as much data as you can to see based on who you know you are, what works, appeals to you. And then you can go, and the book goes on and on to talk about the practical ways of practicing some of these new stories. I would say you don’t have to start by, we talked about change and transition, that doesn’t mean you immediately go out and get a new job or you immediately do what I did, which was pick up and move across the country. That’s very dramatic. In basketball, when you think about what pivoting actually is, they’re small movements. You don’t even move your back foot. A pivot is-

Celeste Headlee:
One of your feet stays planted.

Erica Williams Simon:
Exactly. Exactly. And that’s what I encourage, you can make these shifts in direction without having to immediately transform your entire life. And so I say that change is a practice and these are muscles that you have to exercise. And so I would encourage folks to exercise the muscle of using a new skill that you know you have, but a job has never taken advantage of before. Or exercise the muscle of leadership if that’s something that you’re looking for more of in your career, but you haven’t had the opportunity to put that into practice in your current work environment. So I think practice some of these changes, these narrative changes before you have to go out. And again, we don’t know when this pandemic will end or what the next six months to a year holds for the country. But you can start practicing some of these shifts now in your daily life.

Celeste Headlee:
You’re quite honest in your book about mistakes that you made that you wish you had done differently. I wonder since then, since you’ve been advising others on transitions in their careers, what are some of the common stumbling blocks?

Erica Williams Simon:
I think one of them was the one I just mentioned, which is believing that when you’re ready to change, you should just throw everything up in the air and do it all at once, and that you are going to feel immediately different if you get a new job or if you get a new partner or if you move. And I always say that the first thing you have to do is the internal work. Internal before external, because you can get a new job and a new partner and a new whatever it is and feel the same way you did before if you haven’t actually changed your mindset and the way that you view yourself, life, and the world. So one mistake of not doing the internal work first. The second is expecting a new life to happen overnight. I think we’ve grown up with this narrative, I referenced it earlier, the yellow brick road. We’ve expected change to be a very chronological or path-driven process that, I’ll take one step and it’ll be progress and I’ll take another step and it’ll be progress.

But I’ve seen people who, when they believe that, become completely rattled when the step they took actually is a bit more like a step backwards than a step forward. The best analogy I can give is, as Americans, we think of life in terms of football. We think that we’re supposed to move the ball forward, forward, forward, and then any backwards motion is a loss or a failure. But the rest of the world plays soccer. The rest of the world plays soccer, and in soccer, you actually move the ball backwards in order to kick it farther and kick it forward. And so that’s another tip that I give people, is to make sure that you understand, you may sometimes take steps backwards in order to transition your life. You may take a job that pays you less right now, or you may take a job that you thought was going to be perfect and it turns out you’re miserable there. That’s okay. Life is about figuring this kind of stuff out.

Celeste Headlee:
You used to teach a master class called Tear Down the Walls. It’s one of a number of classes that you either still teach or used to teach. And I wonder what walls you were advising people to tear down.

Erica Williams Simon:
Yes. In the book I give an example or a narrative about a crooked room. So imagine if you were in a room, and this is an actual field study experiment that was done in the 1940s. If you were in a room and everything in the room was crooked, the paintings on the wall, the floor, the chair, everything was crooked. But you were told to stand up straight. I’m going to say that again because there was a noise in the background. But you were told to stand up straight. What would happen? In the study, most of the people reported themselves as being straight when they were really actually bent over at about a 35 to 45 degree angle. And the lesson being that when everything around you is crooked, there is no way for you to stand up straight without feeling crazy. Right?

And so the walls of that crooked room are the stories, are the lies that we’ve believed about ourselves, about our identity, about work, about the world. And so in tearing down the walls, what I encourage people to do is start to tear down some of those stories, some of the walls that you’ve built up around your potential. And this goes for individuals as they’re making career life changes or also I do a lot of work in the social impact sector. This speaks to that as well, some of the beliefs that we have about how the world has to work and how politics has to operate. What is the process by which we can tear down some of those walls to actually get free and live a liberated life and one that is directed more by values and principles, than by the stories that we’ve always been taught.

Celeste Headlee:
This internal work that you’re talking about and that you advise people start with, how does one do that? You’re talking about changing perspectives, right? Whether it be tearing down a wall or starting from… That’s really hard. And it’s especially hard to do in isolation. So are there things that you suggest to people on how to get started on that kind of work?

Erica Williams Simon:
Absolutely. If I had to give one kind of low hanging fruit kit, the first thing that you can do any day, no matter where you are, no matter who you’re with or even if you’re by yourself in quarantine, the first tip is pay attention to what you consume, and immediately begin to edit what you consume. A lot of them, a lot of folks ask the question, how do I hear my own voice or find my own voice? And I say the first thing you got to do is quiet the other voices that are louder in your head. And most of those come from the content that we consume. Come from social media, come from the books that we read, the magazines, the billboards, all of the input. I say we’re living in the wild, wild West of stories, that we are fish in water, stories are everywhere.

But many of them we make a choice to consume. We think that we are scrolling on Instagram or looking at Facebook just to stay connected to people or to be inspired. But inspiration literally it comes from the Latin inspirare, to breathe into. And so I challenge folks to take a look at who they’re following, take a look at what they’re consuming and find out does it actually breathe life into you that makes you more active? Is it breathing life into you that is making you pursue your own goals and dreams? Or is it creating envy? Or is it success porn? Is it just things that you look at that actually make you feel less than? Our eyes are just the greatest gateway that we have to story. And so if your goal is to change your perspective, the first thing that you can do is begin to make better choices about what you look at, what you spend your time engaging with.

Celeste Headlee:
You have a lot of advice for people, not only those who are ready to completely change their lives around, but those who you’ve mentioned already, the people who actually are pretty happy with where they are, but maybe they need to change the way they communicate their story. How does that work start? How do you find a better way to tell your own story?

Erica Williams Simon:
So a lot of the work I do in that regard has to do with identifying your voice, your unique voice in the world. And then once you’ve figured out what your voice is, you can figure out the best way to share it, what platform, are you a public speaker. But I think a lot of people begin with the premise of, I have to talk a certain way or have a certain energy to be a good storyteller, or to share what I have to offer the world. And that’s actually not true. Good communication is effective communication. That’s it. It just means does your audience, do the people that you’re speaking to come away understanding what you intended them to understand? And so that’s not about having a loud voice or a particular physical stance or using the best words.

That’s about the intention and the confidence with which you articulate who you are and what you want. Which again, of course starts with the internal work, which we already talked about. You got to know it. But once you know it, I encourage people in the communications training and the voice training to have something that we call a core message. If you were going to talk to someone, it doesn’t matter how long, for five minutes, 50 minutes, it doesn’t matter. And they were to remember only one thing that you said, only one sentence. What would that sentence be? And this is of course within context, not like you don’t have to have one sentence for your whole life. But whether we’re talking about you applying for a job, or we’re talking about you having a major relationship conversation. For each of those I encourage folks, depending on what their goal is, to identify a core message. One thing that they want someone to remember that they’ve communicated. And then from there we build out.

If you get that one core sentence down, what is the essence of your story? You can call it the moral of your story. What is the thing that you want someone to come away feeling? Write that down. And that takes time, right? Figure that out, wordsmith it, test it out on friends. Get that core sentence down and once you do that, then you can start building out. What are the supporting points around that? What are the examples from my own life that give that one sentence context? What are the words and languages and ideas that I can share that connect that one sentence to my audience? There’s a whole host of strategies, but I think the core message is one of the key learning modules I teach people to be able to really articulate who they are and what they want in the world.

Celeste Headlee:
Before we go, Erica, I had an interesting conversation with a friend of mine who said, there’s stuff I need to do to make sure I’m okay when the pandemic is over, and every morning I get up and say, okay, I’m going to do it today, but every day I don’t because I’m paralyzed. And I’m wondering what you say to people right now who are just afraid, they’re overwhelmed and frightened and not making changes or preparations because they feel they can’t.

Erica Williams Simon:
Yeah, yeah. There are a couple of things. First, give yourself the space. I went to a therapist once who told me, I said, “Oh, I’m so frustrated. I’m feeling this really bad thing. I’m jealous of someone and that’s terrible and I just don’t want to feel that way. So I’ve been upset all week that I’m jealous.” And she was like, “Well, what would happen if you gave yourself 45 seconds to just sit and stew and be jealous and think all the bad thoughts?” And I was like, “I can’t do that. That’s terrible. That’s against what I believe. I’m not that kind of woman.” Blah, blah, blah. And she said, “No, no, no, let’s do that together.”

And we sat for 45 seconds in silence. It was so deeply uncomfortable, but I let all of these bad, negative, jealous, envious thoughts through my mind. And when it was over, she said, “Now what?” And I was like, “What do you mean?” And she said, “Okay, now you’ve done that, you’ve experienced it, you let the feeling happen and we can move on.” And I took that lesson for the rest of my life, that sometimes it’s okay to feel what you feel, and you have to give yourself that space. And most of the anxiety and the stress you feel around it is the guilt you feel for feeling the feeling, right?

Celeste Headlee:
Yeah.

Erica Williams Simon:
So embedded in your question is, Oh gosh, I should be doing more right now, but I’m not. I’m so frustrated that I can’t and I’m paralyzed, but I know I shouldn’t, I keep losing. And that’s keeping you in that state. So the first step I would say is give yourself some time. I don’t know what that looks like for you. If that’s a day a week. I do this thing called morning pages, I write out everything that’s in my head. Whatever you need to do, allow it and be okay and be nonjudgmental about that. And then start to give yourself basic tasks, small tasks. Not, again, I have to read an entire book a week or I have to rewrite my resume by tomorrow, but small baby steps.

This week I’m going to explore. I’m going to just spend my time when I’m online, instead of just scrolling Instagram and looking at people who have a different life than me, I’m going to actually really intentionally start looking at career paths. We just got to look this week. I don’t have to make any dramatic changes. And start mapping out those baby steps. And again, if you miss a day, that’s okay. Pretty much any change in life. I’ve been told it works that way for weight loss, I wouldn’t know. This idea of baby steps and being really gentle and graceful with yourself. Yes, the world is changing right now. No, we don’t exactly know what the future is going to hold. But if we tell ourselves every day you will be okay, you will be okay, you’ve got what you need. Take care of yourself, give yourself the space to imagine and to dream and to learn. And I’m a firm believer that where you’re supposed to be is where you’ll end up.

Celeste Headlee:
Erica Williams Simon, thank you so much.

Erica Williams Simon:
Thank you so much Celeste.