Crossroads…it’s not just a Britney Spears film.
This week’s letter writers are looking to change their relationships to work. One is wondering if it’s time to leave UX all together and monetize a hobby instead. The other is a budding thought leader…who gets the ick whenever they say “thought leader.” Sara and Jen have brought out all their best questions and resources to help these folks get unstuck and plan their next career move—without ignoring the human being at the center.
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Got a work situation eating away at you? Send it to us! Submit your dilemma at
Sara Wachter-Boettcher 0:00 When work is the only thing you use as a marker of success, and work is not going well or you don't have work, it can really lead to this sort of loss of self-worth.
Sara Wachter-Boettcher 0:29 Hey, Jen.
Jen Dionisio 0:30 Hey, Sara.
Sara Wachter-Boettcher 0:31 All right. I have a question for you.
Jen Dionisio 0:32 Yeah.
Sara Wachter-Boettcher 0:33 Would you prefer a custom map of the stars or some sentimental wall art?
Jen Dionisio 0:39 Oh my god. Well, they both sound wonderful. But I vote constellation map. What is this for?
Sara Wachter-Boettcher 0:46 It's our first podcast anniversary. And you know, the first anniversary traditional gift? Paper.
Jen Dionisio 0:52 Oh, oh my gosh, we made it. How did a whole year go by?
Sara Wachter-Boettcher 0:58 I know. Nineteen episodes. One year. Here we are, chugging along with our little baby podcast. Thank you, to everybody out there listening. We appreciate you so much.
Jen Dionisio 1:09 Yeah, it was such a wonderful transition for me as I was starting to work with Active Voice more and work with you more, Sara, to have this to really kind of bring it all together.
Sara Wachter-Boettcher 1:19 Anybody out there listening who's like, "This podcast has helped me," or, "This has been really interesting," hey, if you want to do something to help us celebrate, could you leave us a rating or a review? Or even better: a rating and a review wherever it is that you're listening to this show? We would love that so much.
Jen Dionisio 1:35 Think about it as digital paper.
Sara Wachter-Boettcher 1:38 We'll print them out. So then we'll put them on paper.
Jen Dionisio 1:40 Yes. And hang them all over our podcasting rooms.
Sara Wachter-Boettcher 1:45 Also known as just our regular offices. We're not fancy, y'all.
Jen Dionisio 1:50 Well, speaking of that, shall we get into it, Sara?
Sara Wachter-Boettcher 1:53 I think we should do a podcast.
Jen Dionisio 1:54 Let's do it. So hello, and welcome to Per My Last Email, the show about what to do when work gets weird. I'm Jen Dionisio.
Sara Wachter-Boettcher 2:03 And I am Sara Wachter-Boettcher. Jen, what is the weird that we are tackling today?
Jen Dionisio 2:09 Well, today we're going to be answering letters from some people who are trying to figure out what's next for them in their careers, but are getting really stuck in the process.
Sara Wachter-Boettcher 2:20 Who hasn't been there, right?
Jen Dionisio 2:21 Not me ever. No.
Sara Wachter-Boettcher 2:23 Smooth sailing, always clear what to do next at all times.
Jen Dionisio 2:26 But I will say it's been a really hot topic, I think, on a lot of my coaching calls lately because so many people seem to be at these transition points where what they're doing doesn't feel quite right or enough anymore. And I keep hearing them ask these like big existential questions like, "Do I shift into some really low stress but possibly boring job so I have more energy to give to the rest of my life?" And when people start to turn that over, it can require some real big shifts in how you look at your own worth and what makes you valuable in the world. And I think even for the people who do still feel like they're on the right career path, there are so many questions about, like, how to level up, what leveling up means, how to get more visibility, what to even talk about in the world. And I think for all of these folks, the stakes are feeling really high. And I think you're gonna hear a lot of that and feel a lot of that in the dilemmas we hear today. So are you ready to dive in?
Sara Wachter-Boettcher 3:33 I don't think I'm gonna get more ready than this.
Jen Dionisio 3:35 All right, then let's do it.
Jen Dionisio 3:40 Our first question is from a UX design lead whose background is working in government.
FA 3:46 I've been working as a UX designer for over a decade, and after willingly leaving a difficult job situation in 2023, I'm seriously considering whether I want to stay in the tech and design industry. On the one hand, it's what I've been working and getting an education in for over 15 years. I also have specialized knowledge in a particular subject area that could be really valuable. I work in social impact spaces, so my work can actually improve people's lives. It's well paid and I enjoy it, so it seems like a waste of my background to not continue working.
On the other hand, this feels like an opportunity to try a second career. I've always wanted to have a job that doesn't involve sitting at a computer all day, and I am passionate about my hobbies that I might be able to make into a business. This is extremely scary for me, because I have no idea how to start a business, or even what it would be. I'm still completely a hobbyist and have a lot to learn if I want to make it into a profession. I'll also add that it's been hard to get another UX design job. After months of job searching, I'm just really tired and feeling hopeless after rejections.
How can I fairly evaluate these two options when one of them is something I've spent 15 years honing, and the other is an ambiguous blob of unknown? How can I get the confidence to consider a big career pivot? How will I know if it's the right decision?
Jen Dionisio 5:00 Okay, so Sara, let's call this person FA. And that'll stand for "facing ambiguity". Where would you start with FA? Like, how might they start figuring out what their options are?
Sara Wachter-Boettcher 5:13 So before we get into what FA might do next, I think what I would do if I was working with them is kind of suggest spending some time unpacking the situation that they're in right now, kind of going through their scenario a little more closely. So FA, you mentioned that you enjoy UX and feel good about the impact that you can make with it. And it also pays well. And so this makes me wonder if you weren't having a rough time on the job market right now, and if you hadn't spent so much time getting rejections lately, would you be writing this letter to us? Would pivoting still be on your mind?
And there's not a right or a wrong answer there. But I think it might be worth asking yourself how much of the desire to turn a hobby into a career is coming from a place where you really want to be moving toward that life for yourself, and how much of it might be really about moving away from the current job market? Because this job market is tough. Absolutely. But if your primary driver is to escape the job market, or like, if you're being real honest with yourself, maybe to escape the feelings of hopelessness and fatigue that come from this market, I worry that that's shaky ground to build a business on, because like, I don't know what your hobbies are, but from what I've seen, amongst the friends I have and the people I know in the industry, starting a small business, especially a small business based on something like a craft, it can definitely take a lot. And I would want to make sure that you went into it because that's something that you were really wanting to do.
Jen Dionisio 6:40 Yeah, Sara, I'm glad you flagged that because what I'm hearing in here is that FA might be trading one really challenging path for a very differently challenging path. And so if that discomfort is kind of inevitable for them, it feels like that "why" is really going to matter.
Sara Wachter-Boettcher 6:59 Right. And that is not to say that FA shouldn't do this. Not at all. I know people who have left behind design careers and have zero regrets. I also know several people in design who still have their jobs, and they've turned their hobbies into more like successful side businesses. But you know what, I also know people who tried to monetize their hobbies, and then found that it sucked all of the joy out of them. And that's a really personal decision. I mean, my own husband makes these elaborate ukuleles in our basement. They're very cool. He gives them to his friends.
Jen Dionisio 7:32 Really?
Sara Wachter-Boettcher 7:32 Yeah. Yeah, I never—
Jen Dionisio 7:33 That's amazing! I didn't know that!
Sara Wachter-Boettcher 7:34 Oh I gotta show you these, Jen. I gotta show you these. But, sometimes people ask him like, "Well, why don't you start selling them? Are you gonna sell them someday?" And he just kind of laughs at that, because like, he loves doing this, he spends hundreds of hours on each one, and I cannot stress enough how both hand-crafted and lovely they are. He's like carving mother of pearl into shapes to do inlays. It's beautiful. And there's not really a price tag he could put on them that he could actually realistically get out in the world that would account for any of that labor, like it would always feel like he's putting in this tremendous amount of work for something that can't really return that financially.
And so he basically looks at it as like not something where he's trying to get a financial return, he's doing it because he enjoys making them and he wants to give them to people he loves. So it's all about like the joy of the craft, which is great, right? Like he does not need to turn that into a business. On the other hand, the people who I know who have turned their hobbies into a business, that can be really great for them, too. It can be this sort of creative outlet, it can be this really interesting new way to even apply some of their older design skills. All of these are okay choices. There is no one right answer, there is no moral obligation to turn your hobbies into a side hustle.
There's also no moral superiority to having a highly paid design job instead of a small creative business. Or vice versa. None of these are necessarily inherently the right thing or a better thing. What I think, FA, is that it sounds like you might still need to figure out what feels right to you. Would going all in on a hobby actually make you overall happier? Or would it feel like a slog? You also mentioned that you're not sure what the business would be and that you had multiple hobbies like which one would you focus on? And I think side by side with that, what would a sustainable income be for you? And what does that mean for like, what you'd need to sell and how much of it you'd need to sell and at what price point you'd need to sell it?
There are a lot of questions in here. There are so many more questions than the ones I'm posing right now. And, FA, I don't think you need to answer them all up front. But because you said that you're not sure what the business would even be, I think it sounds like you need to explore this space a bit more before you'll know what's right for you.
Jen Dionisio 9:50 Sara, this is actually making me think of my pivot into coaching and probably yours as well. When I started my training, it was very much with the thought that coaching would be a tool I'd use in the work I was already doing, as opposed to this very separate career to pursue. And when I started thinking about it more as a career than a skill set, there were a whole lot of new things that I had to consider like, do I want to spend a big chunk of my time on marketing? Do I want to spend a big chunk of my time on program development? Do I want to spend time on business development?
Because in order to be able to make a coaching practice sustainable, those tasks were going to need to be as much in the mix as the actual coaching work. And like my answers were, "Yes, hell yes, and, yes, but it's gonna be scary". But Had there been some no's in there, maybe I wouldn't have chosen to pursue that as the single path forward.
Sara Wachter-Boettcher 10:52 Right. And you got those answers by kind of digging in and spending time with them and I think if I remember correctly, like starting to do some of that work, right? Like, I know that you started writing a newsletter, you started trying to put out some programming, testing waters with group programs. And that kind of experimentation, I did a lot of it too, that kind of experimentation is really how you figure out "Is this what I want? What do I like and dislike about it? What works for me?" And I think, you know, a creative hobby-based business might be a bit different, but I think it needs the same kind of experimentation. And so, FA, that's what I would really challenge you to think about.
What would it look like to experiment with going down that path of turning one of these hobbies into a business? You know, I have a friend who started out by selling earrings really expensively to their coworkers, when they were just kind of figuring things out and starting to play they were working with, like polymer clay as a fun little, you know, side thing in the evenings. And it helped them figure out some of their production issues and help them figure out like, what were the things that people wanted and actually bought. And it also just kind of helped them kind of tiptoe into starting a business. And now, you know, they're on Etsy, and they're at a bunch of craft markets, and they're doing a brisk business, and they're still getting going, you know, she hasn't quit her regular job yet.
But all of that happened, because, you know, she took a series of little steps to kind of dip her toe further and further into it. And the thing is, I know that making jewelry gives them tons of joy. But I also know that some aspects of it are not always as much fun and that are pieces that she asked to kind of work on, like, I don't know, dueling with all of the like listings on Etsy, making sure you have good photos and the good descriptions and the SEO and like trying to do the social media stuff, creating reels and like, all that stuff can take a long time and can feel like this sort of extra weight on top of the thing that you really enjoy doing.
And it doesn't mean that those tasks are all horrible all the time, it doesn't mean that you have to hate them. But it does mean that you might need to get a fuller picture of like, what would it take to run this business beyond the part that you already know, which is the hobby? And how does that feel to you? And is that a balance that actually makes sense? Like, again, do you got some no's in there? You got some hell yeses in there? Those are going to be probably important questions. So, FA, what might your creative hobby business look like for you? I really want to challenge you to come up with maybe a few small experiments to help you find out. And they don't need to be definitive. You don't have to, like set up an ecommerce site and design a brand and be like "I'm launching". But I think you need to explore like, what happens when my hobby becomes work? What does that feel like for me?
Jen Dionisio 10:54 Yeah, well, okay, so Sara, there's that hobby side. But FA is still not sure if they want to fully let go of their UX work. So,
Sara Wachter-Boettcher 13:55 Yeah.
Jen Dionisio 13:56 How would you suggest that FA approaches that?
Sara Wachter-Boettcher 14:00 Yeah, you know, as I read FA's letter, it really struck me that even if they decide to stay in design, or stay in design for now, it does sound like something needs to change, because it sounds like their job search is just not working for them, that they're feeling ground down, rejected, hopeless, exhausted. And, you know, I know that they're not alone. We hear this a lot from people who are looking for new jobs in design right now. It has been a rough time. And, you know, I know that some people are finding jobs. I know that there's more openings now than there were.
But if you've already been ground down by that long term job search, that might feel like cold comfort, because things can just really feel so impossible, especially if you're spending your days in like the LinkedIn echo chamber with a bunch of other job seekers who are struggling, and also big voices in the industry who are spreading doom and gloom. That can be a dark place. And so, FA, if that is feeling familiar, here's something I want to propose to you: what's something you can invest in that's not your job search? Specifically, like, what is something that makes you feel alive, joyful? What helps you feel like you're in your body or maybe that you're connected to other human beings?
And I don't actually mean networking here, though, maybe you want to do networking. What I mean is more like being alive and being part of something. And you know, Jen, I say this because when a job search is going poorly, it can create this really negative cycle for people. I know, you've seen it.
Jen Dionisio 15:27 Yeah.
Sara Wachter-Boettcher 15:28 You get some rejections. You start to feel a little worse about yourself. Or maybe you start to get a little more cynical or negative about your field. And then yeah, well, those bad feelings, they kind of seep out in your next interviews. And over time, what happens is like, you kind of show up worse and worse, like, it gets harder and harder to put your best foot forward at precisely the moment where you need to. And so what happens is, that just reinforces all of those negative feelings. And some people are really good at applying those negative feelings to themselves, right? Like the inner monologue is very much, "I suck. I don't have anything to offer," right?
Jen Dionisio 16:05 Yep.
Sara Wachter-Boettcher 16:06 And then there are some people who really push that outward, and their negative feelings are like, "This industry sucks. This industry is broken." And when you're in that place, that is a really tough place to shine from, to stand out from, to speak specifically about what you might bring to an organization because either you feel like shit about yourself, or you are already skeptical and angry at the place you're interviewing, and like, that's just not going to help you.
This is why I think it is just so important for people to really think about and embrace and cultivate their identities outside of work. Because you know, when work is the only thing you use as a marker of success, and work is not going well or you don't have work, it can really lead to this sort of loss of self-worth. So FA, good news, you have something going for you here: your hobbies. You've already said that you are passionate about them, that you get a lot of joy from them. And so FA, maybe your hobbies are part of what you want to turn to for joy right now. And honestly, that's also part of the reason why I'm suggesting that FA make some experiments around turning their hobbies into a business.
Because experiments are low stakes. They can be fun. And I would really urge caution before FA puts a ton of pressure on themselves to make those hobbies a business immediately if they're already feeling frustrated at the stalled job search. Because with a lot of pressure on the hobbies, that could suck away one of the things that is giving FA joy right now. And I think they probably really need that.
Jen Dionisio 17:40 Yeah, that's a great point. So if I'm following, Sara, is it that you would recommend FA tries to do more kind of joy-bringing activities while they're looking for a new job? Or are you recommending that they take a break from the job search altogether?
Sara Wachter-Boettcher 17:57 That's a great question. And I think either or both could totally work. I think either would be beneficial.. It may not work for them to take a full break from the job search. I don't really know what their situation is. I don't know how they're doing financially. But one of the things that I would say is like, sometimes taking a break in the short run, even if that feels impossible, it can actually help in the long run, or even the like, medium run. Because if you are feeling fried, you're not showing up at your best, you are feeling cynical, or you're down on yourself, and when you don't feel like you, you maybe aren't in the best position to get yourself a job. Like you are maybe not going to be showing up in that room with the parts of you that you really need to nail an interview.
And so taking a break is really hard. But sometimes that break is the way that you kind of come back to yourself, feel refreshed, maybe even like find a little bit more excitement for the job search or for the interviews that you're going on. And that can really change things. But you know, again, I don't know what exactly is going on with FA. One of the things they didn't mention in their letter is the financial piece. You know, they left their job a while ago. They quit a job it sounds like without having something lined up. So it sounds like they maybe had some runway financially, but I don't really know how long they continue to not bring in income.
So FA, when you look at your financial situation with a little bit of distance, I'm curious, like, what does it look like for you? If you continued bringing in little to no income for six more months, what would happen? A year? And now thinking about that length of time can be hard. Like for a lot of us it produces a pretty immediate freakout, a sense of like, "That's impossible". I have that feeling. But when I really pause and think about it, if I said, "Okay, Sara, if you just simply were not making money for a year, you simply weren't there is no way to change that, that is what's happening, what would life look like?" That forces me to get concrete and to actually look at well, how bad would it be? What money is available to me? What would I do, right?
And so FA, what I propose here is that you really focus on the practical and tangible impact of that on your life. So like, for example, if this were happening to me, I would not enjoy dipping into savings. I have been planning to hold onto my savings for when I'm older, but the savings exists. And so that would be an option that I could take that could extend my runway so that I would be okay financially if I weren't making any money. And knowing that that exists, and that I can do it, and of course, there's trade-offs, of course, it may not be the ideal situation, but knowing that exists helps me make sure that I see that there are options. It's just really helpful, FA, to get clear on the choices that you do have, and what it would look like if you took any of those choices.
Now, FA, you might also find that you don't have that much runway. And so something else I want to throw out there for you is this: how does it feel to imagine getting a part-time job or like looking for some freelance gigs to help you ride out this time and maybe buy yourself more space in this job search process, or in the process of setting up a new creative business? Again, I don't know your situation. But I have a friend who actually had a similar thing. She left a job because it was an environment that she couldn't exist in anymore. And she's looking at going back to doing restaurant work a couple days a week so that she doesn't have to worry so much about income. And she doesn't have to worry so much about how soon she finds a job.
I just saw a post just yesterday on LinkedIn from somebody who did something similar: they got a barista job, because they wanted something to do while they were unemployed to bring in some money. They'd done it before when they were in school. And it felt like an interesting way to kind of get out of the house. And they actually felt that it was giving them a lot of like joy and new energy just to be out doing something different. And something maybe physical for a while.
Jen Dionisio 18:32 Yeah, and connecting with people and like rebuilding that sense of community. I've talked to a lot of people who have been either considering or doing similar.
Sara Wachter-Boettcher 21:53 Yeah. And you know, I think this can be hard for us to do mentally or emotionally because going from a professional role to a service job can feel like a demotion. I think culturally, we've really labeled that as a sort of demotion. But I also think that's pretty classist. And I also think like, professional jobs have not been that rosy for people, you know? It's like you work really hard to get into these professional well paid careers. And then like you spend your days dreaming of when you were a barista. That's telling us something.
And so I think it's really wonderful to see people choosing to go into something like a service job, even though they have this professional background, and to not look at that as somehow, like failing, or something that says something negative about them. I think it says something lovely about them, which is like, they're willing to do service work, which is hard, and they're willing to try something new when whatever they were doing wasn't working. I think these kinds of resets can be really powerful. And I also think that like, if you find that you love working with people every day in a coffee shop, maybe that's fine. Maybe it doesn't make you a better person to go, you know, invest in your design career, which I know intellectually is true, but I think is really hard if you've been trained to believe it is better to be a professional, I think that can be hard to really internalize.
Jen Dionisio 23:20 Yeah, I remember when I was both working in an office and working as a bartender, like, I would have colleagues come in and serve them and have feelings of ick and discomfort. And more recently, like a friend that owns a restaurant when I was starting to transition out of my job, I was like, "I would love to pick up some shifts." And it was interesting to see how differently I felt about it now, or more recently, than I would have felt about it way back then when I was starting my career and felt like I had so much to prove externally.
Sara Wachter-Boettcher 23:51 Yeah. And I think it's great that we’re kind of like revisiting some of that, you know? I had some crap jobs in my time. And some of them I do not want back. But there are some aspects of having a low stakes job that were really lovely. Like, it was really nice to never take any work home with me. And not just work like physical like actual doing. But also just like I didn't take home work problems in my head, right? Like, I just didn't think about it when I wasn't there. And that was beautiful. And also, like you said, connecting with people—that can actually be really enjoyable for some of us. I understand not everybody. For some people that's very, very trying to do all day.
But there can be really wonderful things about it. And so FA, here's what I really want to leave you with: there is no right way to live. So just because you've been in design for 15 years doesn't mean you'll be wasting all of that if you decide you don't want to do it anymore. You're allowed to pivot, and you're also allowed to try something out, realize it's not for you, and then change your mind again. But you know, if you are down in the dumps right now ready to throw your laptop out the window, you might not be in the best headspace to make huge final decisions. So how do you lower the pressure on yourself? How can you turn your big ambiguous decision into those small experiments? And what happens if you optimize right now maybe for feeling good and exploring what's possible instead of having "the answer"?
Jen Dionisio 25:18 Yes. Because there is no one answer, right?
Sara Wachter-Boettcher 25:20 Right.
Jen Dionisio 25:21 There are so many that you'll find as you go. Ah, FA, keep us posted on how these experiments go. We would love to support you and also hear what you're learning.
Emily Duncan 25:34 Hi, folks, Emily here. I'm PMLE's producer, and I am pumped to share that Active Voice has a new program starting on May 8, called the Managers Playbook. It's a four-week workshop series for leaders who are ready to have more fulfilling and productive relationships with their team members, peers, and partners. Sound like a fantasy? No way. In this program, you'll practice powerful coaching, communication, and relationship skills that will help you lead up, down, and across with less stress and more success, whether you're giving feedback, evaluating performance, building influence with partners, or resolving cross-functional challenges. You know, all those tricky conversations our listeners write to us about? If you want to see less back-channeling and burnout and more connection and collaboration on your team and in your org, go to https://www.activevoicehq.com/ and click on Group Programs to learn more.
Jen Dionisio 26:27 All right, Sara. Are you ready for our second dilemma?
Sara Wachter-Boettcher 26:30 Let's do it.
WS 26:32 I have a long term goal of growing in "thought leadership" - though I don't love that term. I mainly mean that I'd love to write and speak about the industry, maybe one day write a book. I love public speaking especially. Mentoring others one day would be cool. I made it a short term goal to submit a blog post or talk proposal. But I cannot think of anything I could say that is "worth it." How do people do this? How do you figure out what you do that is worth sharing to the design industry?
Jen Dionisio 26:58 I am going to call this person WS for "worth sharing". And I am really excited to hear your answer in particular to this question because, don't cringe, but you are the person in my life that I think of as like the quintessential thought leader.
Sara Wachter-Boettcher 27:17 Oh, thank you. Ew.
Jen Dionisio 27:19 I know, I knew it was gonna get that response. But like, I don't know. Is there a better term for it?
Sara Wachter-Boettcher 27:27 Yeah, I mean, I wish there were. I've tried to come up with one. I haven't really come up with an answer to that. But you know, thinking about this question actually made something click for me, something that I think actually might help with WS's dilemma.
Jen Dionisio 27:40 Ooh.
Sara Wachter-Boettcher 27:41 So I think the reason "thought leader" is so icky as a term is because it's so focused on the identity of the person, like "they're a leader who leads through their thoughts." But it doesn't really speak to what's valuable or useful about what they're doing. Like, we all have thoughts, and trust me, most of my thoughts do not need to be turned into an essay. And so I think one of the reasons that this word gives people so much ick is that if your goal is to be a thought leader, that can become very ego-driven. And that can lead to a lot of really shallow content that's not particularly valuable because it's so focused on how you are perceived by others, like "I want to be seen as a thought leader," instead of being focused on what it is you want to bring to the world.
So what I might propose here is that we focus a little less on what we call the person and a little bit more on how we describe the value of this type of speaking and writing. So like, what is the function of writing and speaking about your work for your community? Like, what does it do? And that might be a lot of different things. You might be educating people, providing instruction, it might be giving people new perspectives, new approaches. But I kind of think it all ultimately comes back to one thing which is like advancing a field of practice. I think at their best, things like talks and essays and books in tech and design, they're really meant to further the discipline, to help us get better at our work in some way, to help us maybe move our processes forward or move our organizations forward, to mature our craft or our leadership skills or sharpen up our thinking or expand our understanding of like, what this work is and could be.
So when I think about it that way, I think of this as being really similar in function to things like writing papers or presenting at conferences in academia. And in fact, you know, that's where some of the industry conferences I've been to actually came from, like some of the older ones that have been around a while, they still kind of have that academic vibe. And, you know, the work that WS is interested in putting out in the world might not be academic. I don't think it needs to be academic. But I think in an ideal world, it's performing a really similar function for our communities as academic work is in academic communities: moving the field forward, adding to the corpus of knowledge.
And you know, the other parallel there is most papers in academia, they're not some huge, groundbreaking thing. Those are really rare actually. Most are just making a little contribution. And then each small contribution builds on all of the others, deepens that well of knowledge, kind of helps people have this body of work that they can turn to as they're thinking about their own research interests or their own areas.
Jen Dionisio 30:35 God Sara, this way of thinking about, ugh, "thought leadership" is really freeing, right? Like, I've, as somebody who struggles with sometimes feeling uncomfortable in a similar way to WS like, thinking about the content we're sharing, or the conversations we're starting, or the ideas we're putting out there as being sort of part of a collective knowledge base—
Sara Wachter-Boettcher 31:02 Yes.
Jen Dionisio 31:02 Takes so much of the pressure off and makes it feel so much more, I don't know, generative instead of kind of performative.
Sara Wachter-Boettcher 31:11 Yeah. And to be clear, like, look, if you get up on a stage and give a talk, there is an aspect of performance to it. And I'm not going to lie to people and say that there isn't. But I think ideally, the reason you're doing that performance is because of something bigger or greater, which is very different than I think the way that we've started to talk about thought leadership, which is very like, this like perfectly polished and poised kind of TED Talk vibe, which does feel like it's very much about the performance. I say all of this, both because it was something that like clicked for me, but also because I think this is where we should start with WS. Because WS, I love that you have this goal of submitting to a conference and writing a blog post. I want that for you.
But what I don't see in your letter is anything about why this is something you want to do. Like, what makes you want to speak and write more? What calls you to it? What feels important or necessary about it to you? I asked this because I think that framing your goal as "become a thought leader" might actually be getting in your way here. Because again, saying "I want to be a thought leader," it really orient you toward "how will I be perceived by others?" which is not even actually in your control. But what it doesn't help you figure out is sort of the what, like, what is it that you know that you want to bring out and share? What's something you see happening in the field that other people aren't seeing yet but really need to? You know, in other words, WS, I want to challenge you to really refocus your goal around what and how you want to add to the body of knowledge in your field.
Jen Dionisio 32:45 I love that. And it makes me think of how much all of us are really kind of doing some version of thought leadership every day at work already. You know, if you're trying to educate your product partners on your discipline, or you're trying to rally people around a process change, well look at you. You have a perspective and you're sharing it.
Sara Wachter-Boettcher 33:07 Yeah.
Jen Dionisio 33:08 And I think thinking about it in that way, like, I wonder if it makes the pressure of finding that like one perfect topic or idea much less intense. Because like I know, personally, like when I start thinking about it with that level of stakes, like it will block me from writing entirely, you know? Like the comparisons to other people will start overwhelming my brain, and then I will inevitably go to that kind of "why would I bother?"
Sara Wachter-Boettcher 33:38 Yes. The idea that a big perfect ideas somehow gonna emerge from us overnight is also just like, not all things work, in my experience. In fact, I think that lowering those stakes and thinking of it as perspective sharing is the best way to start to develop what it is that you need to say. I actually wrote about this almost five years ago now, Jen. I looked at the data, and I was like, "Oh, well, five years ago, okay." I wrote this article called "Don't feel like an expert? Share anyway." We're gonna link it in the show notes. And I want to talk about it because it came out of all this research that I did with Katel LeDû who runs A Book Apart. We did all this research on professional visibility.
So we got, for example, like a couple 100 survey responses. And we then had a bunch of interviews with people. And one of the things that people told us over and over again, is that they felt like they wanted to be more visible professionally. They wanted to share their ideas. But they felt like they were uninteresting. They felt like they weren't expert enough. They felt like they see so many profound talks, blogs, and material out there that they worried that they would never match up.
Jen Dionisio 34:50 Ouch.
Sara Wachter-Boettcher 34:52 And that's just a few of the actual things people said. There were so many more quotes like this. So WS, If that sounds familiar, which I think it will, just know you're so not alone in your feelings. Your feelings are very, very, very typical. But those feelings are not because you don't have anything to share. It just means you might need to get a little bit more connected with those underlying reasons that you want to do this. Women Talk Design, which is an organization that I know both Jen and I really love, we share their stuff a lot. Yeah, they have a handy new book on public speaking. And one of the things that they talk about in there is finding your "why," like, "why speak?"
Jen Dionisio 35:28 I am so excited that my copy of the book came in the mail yesterday. And so yeah, listeners, turn to page 18 if you want a whole list of prompts about finding your "why."
Sara Wachter-Boettcher 35:40 Yeah.
Jen Dionisio 35:41 Sara, what has been your why? Like, what made you start speaking and writing? And, you know, how did you decide what to speak and write about? I know that's changed over time.
Sara Wachter-Boettcher 35:52 Yeah, honestly, what's always guided me are my feelings, and specifically, anger and annoyance, if I'm being honest. And what I mean by that is that whenever I would feel like I was like reading a post or listening to a talk, and I would have these strong reactions, like, "Why are they talking about X when Y is so much more important?" Or like, "This is so over simplified. Why aren't they going deeper?" I realized that those are signals. And they're not really signals actually about the other speaker or writer.
It's really not about them at all. It's actually a signal about me. It's telling me that this is a topic I care about because it's riling me up in some way, and that I might have something to add to the conversation, right? Like instead of "Why aren't they talking about X?" it's like, "Oh, they're talking about Y. Someone should really also be talking about X. Maybe that's me."
Jen Dionisio 36:46 Oh, again, it's that idea of like adding to the collective knowledge base, as opposed to having to have it all figured out yourself.
Sara Wachter-Boettcher 36:52 Right. And it's not just that I would have that kind of anger or annoyance when I was like consuming other people's thought leadership. It's also noticing when those feelings would come up when I was like working on design teams or working on a project, you know? Sometimes I'd be thinking like, "Geez. Why is no one thinking about how our users actually going to find this content?" Or, "Why aren't we talking about how this feature can be misused or used to hurt someone?"
And what I realized was that people weren't doing whatever it was that I thought they should be doing because they didn't know how. It wasn't part of their process, or it just wasn't on their radar yet. And what I realized is that often there were things that seemed really obvious to me, like I would kind of be doing the systems thinking stuff, and really thinking like several steps ahead about how our choices now can impact us down the line. And those things that felt obvious to me, they were just not necessarily obvious to other people. And I had a choice there: I could hang out and be resentful about it and roll my eyes at them and like, be like, "Why aren't they thinking this through?"
Or I could choose to help them see the things that I could see that they were missing. I could choose to kind of like share my perspective and ways of working and hope that they'd catch on, hope that that might shift what people thought about. Not because I had all the answers, again, but because I had a perspective. I had a lens on the world and on my work, and my lens was different from the other people around me, and so every new perspective helps us see more. So if I added my perspective, then that would help people get a fuller view of the field.
Jen Dionisio 36:54 Makes sense.
Sara Wachter-Boettcher 37:09 So WS, I wonder, what makes you angry or frustrated about this industry? Doesn't mean you need to write or speak from that angry place, but that might help you uncover something. Or what are some ways of working that feel natural and necessary to you, that feel may be obvious, but don't seem to be on other people's radars. And WS, It doesn't have to just be things that frustrate you. Like that often works for me, but it might not quite do it for you. You might also want to look at things like what's easy for you that somehow seems hard for other people?
Or what are the parts of your work that feel very natural to you, but other people often don't understand? Sometimes it's about looking at the things that we take for granted, the things that again, feel obvious to us, and then figuring out, "Wait, are they actually obvious?" And if they're not, then it's probably a spot where we have something really special to add.
Jen Dionisio 39:21 And, you know, something I'd recommended to WS as well is like, if you're not sure what those special things are that you have to add, ask people. You know, your colleagues and friends can probably name so many things that they've learned from you or ways that you've changed their perspective or opened their minds. You know, and if that feels uncomfortable, you can also just start paying attention right now to like, what are the subjects you've talked about that get you giddy or fired up or really curious?
You know, you may be actually writing that blog post or the seeds have a talk in your everyday life as you just communicate to people. Obviously, most of us have an easier time sharing in spaces and with people who make us feel safe. But Sara, it does sound like WS kind of wants to extend their reach to a much broader audience of people in the industry that they may not know yet. And so how do you suggest they kind of build up the confidence to do that?
Sara Wachter-Boettcher 40:30 I think it's really worth saying here that speaking and writing about your work publicly is vulnerable. You're putting something out there that other people might disagree with. In fact, I think you need to put something out there that people could disagree with. If it's something that nobody would disagree with, it probably means you're not adding a lot. And that's scary. It can be especially scary if you were socialized to play it safe, to people-please, to not rock the boat. Women particularly are socialized this way. But it can absolutely happen to anyone kind of depending on how they grew up and formative experiences that they've had.
And it's also about how you might be perceived when you speak up and when you share something. If you're from a group that is underrepresented, marginalized, historically oppressed, like, your experience of people's reactions to your opinions might be different than some other people's. And so you do have to think about that vulnerability, like there is some level of risk there. But the other thing that happens that I have found is that when you have that kind of conditioning, right, that conditioning to like, be nice, play small, what can happen is that you start to like reflexively water down your point of view.
And you might worry about okay, "Am I wrong? Am I too much? Am I saying something that anybody cares about?" And so when we do that, what ends up happening is we often weaken our arguments or we weaken our opinions. We sort of learned to shy away from taking a strong stance. And when we do that, over time, we can actually start to like, become disconnected from what we really think. We can actually, like, have a harder time forming an opinion, even to ourselves, because we've shut off that part of ourselves because that part of ourselves doesn't feel safe.
And so if you've done that, if you have a history of doing that WS, then that might be part of what's happening when you take a look at the ideas you have and think, "Well, this isn't worth sharing. This is boring." Some of that might be just self-doubt imposter syndrome stuff. But some of it might be like, yeah, if you've already watered down your ideas, then yeah, maybe they aren't the ones that are worth sharing. But I think it's worth looking at, "How could I kind of zoom out from this and figure out where I have a stronger opinion than I'm actually stating? Or how can I sharpen up some of these opinions that I'm coming up with and like, kind of get to something that's meatier, that's spicier?
Jen Dionisio 42:53 Ooh yeah.
Sara Wachter-Boettcher 42:53 So WS, I would really suggest thinking about this, like, are you watering your ideas down and then rejecting them because, you know, they're watered down, so they're not that interesting? And if that's happening, is it because you're afraid to say something that someone could react negatively to? If that is possibly happening, what I would say is it is time to look at how do I stop sanding off all the most interesting parts of my ideas? How do I stop taking out the spiciest bits? How do I embrace that bolder side of things?
Sometimes that isn't coming up with a point of view, it's more like giving ourselves permission to say what we actually think with our full and unfiltered voice. And again, that's a risk, like not everybody will agree with you if you say something bold, but I think that's also where the power lies, because it means that the people who need to hear it will really hear it. And it means that there's something new being added to the field and not just the same old stuff being rehashed.
Jen Dionisio 43:53 I wanted to kind of double down on that idea of like, the people who really need to hear it will really hear it. You know, there are certain topics I've at times shied away from speaking on, because I didn't want to look inexperienced or unknowledgeable or like, bad in some ways, you know, and when I think about holding some of those ideas back now, it really makes me realize, like, if I'm doing that, I am not talking to the people that I actually want to feel less alone, because they recognize their messiness and their growth in somebody who's not perfect either.
Sara Wachter-Boettcher 44:32 Right. You know, this is something that has come up for me a lot recently in the past few years when I've noticed that a lot of conferences kind of moved toward inviting people with like, shiny big tech brand names on their resumes. And I noticed that a lot of those talks felt like they were the kind of shallow, over-simplified, "Here's how we do it here and this is the best practice". And I found that those don't do a lot for me because A) I don't actually believe that things are so perfect at any of those companies like trust me, I've worked with enough people inside those companies to know.
And then B) most of us are messy and imperfect and in messy organizations. And I want to know, like, how do you actually do some of this stuff in places where it's hard? What do you do when you get stuck? What do you do when you don't have all the budget or you don't have all the answers? And I think that that's where you get into so many more interesting ideas.
Jen Dionisio 45:29 So Sara, if WS does kind of find themselves watering themselves down and, you know, making their ideas generic, so as to be like, palatable, you know, how might they kind of tap into that sharper, spicier perspective that you're talking about?
Sara Wachter-Boettcher 45:44 So in addition to that article I wrote, which, by the way, WS, it has a bunch more questions to ask yourself to help like, tease out what you think and what you might want to say, I'd also recommend that you read this post from Wes Kao about having a spiky point of view. We're going to put that in the show notes, too. This is full of thought starters and examples to help you take sort of stuff that feels generic or ho-hum and turn it into something bolder and spicier, or spikier as Wes puts it. And as you do this, again, WS, you do not need to have a huge groundbreaking idea here. You don't have to have something that's going to like, change the industry forever.
All you need to have is something that is a meaningful addition, something that helps your audience think or see or work just a little bit differently. All you need to do is add to the body of knowledge or widen the field of study, sort of challenge some belief that people might have, or some assumptions they might have. And it can be again, in the smaller ways. And you know, I think that is actually the last thing I really want WS to know here. Don't make this so big. Don't make this "I need to come up with a book idea." You know, instead, I really recommend start with just thinking, "How do I share some insights and ideas that I already have in some low stakes ways?" Like I used to do this all the time on Twitter back in the day. On LinkedIn now, because I'm not so into the Nazis on Twitter.
Jen Dionisio 47:14 Good to hear.
Sara Wachter-Boettcher 47:14 Yeah, but I really would just sort of like post some stuff. You know, Jen, you mentioned this before, I think this is a great way to get a read on other people's reactions, like when you share with your team or when you share it in, you know, your company Slack. But also on a place like LinkedIn, or maybe a Slack group for your professional community. I know a lot of people are in various Slacks, because the point isn't to be a thought leader. It's really to share stuff that's been helpful in developing your practice, and then find out who else needs this. What resonates? What do other people kind of latch on to and go, "Ooh, I've never seen it that way?”
Like when you talk about, let's say, a problem you were having with your product partners, and then how you redesigned a workshop or deliverable to solve that problem, whose ears perk up? Who goes, "Oh, oh, I need this. How did you do that?" Feel that out, play in that space. You know, WS, I really mean that: play. This is again, about experimenting, about kind of being present in and with your community and seeing like, where do the conversations go? What ideas stir up discussion, which ones maybe peter out? The other thing that I think comes up in there is like WS, you are not going to hit upon your strongest point of view by just like thinking really hard about it.
Jen Dionisio 48:33 Aw dang.
Sara Wachter-Boettcher 48:34 I know, sorry. Unfortunately. Hey, if we could just think really hard about all of our problems and solve them, we would be in a very different place, right? The way that we actually get to our strongest ideas is usually by like talking our early ideas through with other people, by exploring a bunch of different related threads, by being curious and being generous and being real. I will say that's definitely something that I have tried to practice like, you know, maybe I'm going to explore something. I used to be like, "Oh, let me just tweet something off and then see if people reply to it."
And then maybe over time, it would get me thinking, exploring more threads, and I'd turn it into a blog post. And it was only when I would find myself kind of like, working on the same ideas over and over, like riffing on them, expanding on them, refining them. It was only then that I would think, "Ah, this, this is a thing, like a capital T Thing. Like this is something I want to go deep on." And that meant I wasn't doing it because my goal was to be a thought leader. I was doing it because I was stuck into this problem space. I was like, "Oh, this is a thing that I'm interested about. And this is also a thing I want other people to think about. I want to be a better thinker. And I want my industry to be better too."
And that's what's going to drive me to do that work. So WS, that is what I want to leave you with today. What do you want to contribute to your field? What's missing out there today that you wish your peers were talking about? What's helped you get where you are, and what might help other people if you just shared it? I want to hear about that. And I know other people will, too.
Jen Dionisio 50:13 Sara, this is making me think too, it's another example of the sort of small experiments, teaching yourself to learn from them, react to them, build on them so that you don't have to get it all figured out right away.
Sara Wachter-Boettcher 50:27 Exactly, exactly. It's like I make these little bricks of ideas that I put out there, and over time, they may be turned into something, and some of them don't turn into anything. And then the things that kind of start to turn into these larger structures, those can turn into essays, those can turn into talks. And then maybe, you know, you add some more bricks, you add some more bricks, and eventually you have something much bigger like a book, or you just have a whole lot of bricks that you've contributed to your field as a whole. And all of that I think is actually so much more powerful and so much more important than just being a thought leader.
Jen Dionisio 51:01 Amen. So WS, I hope that takes a lot of pressure off you and makes this adventure feel a little more fun for you and a little lighter for you as you start sharing your thoughts with the world. We're listening.
Sara Wachter-Boettcher 51:15 Oh, hell yes. And I want to read them.
Sara Wachter-Boettcher 51:24 That's it for this week's episode. Per My Last email is a production of Active Voice. Check us out at https://www.activevoicehq.com/, and you can also get all the past episodes show notes and full transcripts of this podcast at https://pmleshow.com/. This episode was produced by Emily Duncan, and our theme music is "(I'm A) Modern Woman" by Maria T. Buy her album at https://thisismariat.bandcamp.com/. Thank you so much to Facing Ambiguity and Worth Sharing who submitted their stories for today's show. And thank you for listening. If you've got a work dilemma eating away at you, send it to us. Head to https://pmleshow.com/ to submit your story. See you next time.