187. Experimenting, Failing, and Finding Your Job Fit - Catalyze Your Career

[00:00:00] Matt Abrahams: What if we saw our career as a series of hypotheses that we need to test? So, essentially, we're experimenting to learn what is the best fit for us. My name is Matt Abrahams, and I teach strategic communication at Stanford Graduate School of Business. Welcome to Think Fast, Talk Smart, the podcast. This is the second of three Catalyze Your Career miniseries episodes that we've produced in collaboration with LinkedIn. Together, these three episodes will help you chart your career path and find your job fit. In case you missed it, I encourage you to go back and listen to episode 184, Fit or Quit, the first episode in this miniseries that was distilled down from a LinkedIn Live event that I did with Catherine Fisher, where we answer live career questions from you, our audience.

[00:00:56] Today, I'm really excited to talk again with Dorie Clark. Dorie and I had a really thoughtful conversation about personal brand and our careers in episode 118. As a reminder, Dorie is a consultant, speaker, lecturer, and author. Among her many books are Standout, Representing You, and her latest, The Long Game. Welcome back, Dorie. You provided so many useful and actionable ideas last time we met. I'd love to hear even more.

[00:01:25] Dorie Clark: I will do my best. Matt, thank you for having me. 

[00:01:28] Matt Abrahams: All right. Are you ready to get started? 

[00:01:29] Dorie Clark: Amen. Let's do it. 

[00:01:31] Matt Abrahams: When it comes to careers, how important is it to have a long term vision for our career? And what steps can we take to create and refine that vision over time as things change?

[00:01:42] Dorie Clark: So I think it is important to have a long term vision, but I want to be really precise about the terminology because I think that this is what trips up a lot of people and maybe intimidates some of them. I think understandably, we often assume that it's really essential to have everything mapped out between now and twenty years from now. And that's how responsible people do things. And then we look at our own lives and say, but I don't know where I want to be in twenty years, or maybe I do know where I want to be, but I certainly don't know how to get there. And so we feel paralyzed from even really beginning, because we say, that just doesn't seem possible. I'm making it up as I go along. 

[00:02:18] And I want to actually encourage people to reframe this. I prefer the terminology provisional hypothesis because it's useful, of course, to have an idea where you want to go so that you can be somewhat directed in the choices you're making. But we also have to recognize that, yes, things change. Yes, sometimes great opportunities emerge and you don't want to be so paralyzed that you can't take advantage of them. And sometimes there are going to be roadblocks that no one could have anticipated. And you don't want to be so mired in your plan that you are not nimble enough to avoid them. So if we have at least a hypothesis, we know where we're going, but we also recognize the GPS coordinates on the way there may change.

[00:03:03] Matt Abrahams: I like framing it as a hypothesis because that implies that you can do some testing, right? And you can check things out. What's some advice you give to people who are trying to find a career or a job that fits them? Are there certain questions we can ask, certain things we're looking to do to test out that hypothesis?

[00:03:20] Dorie Clark: I'm a big fan of testing hypotheses because there, there's a lot that, that we don't know. And it's not even because we're not smart or we're not doing research. It's just, there are a million unknown variables. And if you haven't been exposed to something, it's not your fault. There's just no way that you could even imagine what the questions are to ask. And diving in and testing in small ways allows us to be flexible. One thing that I've found very helpful, is always trying to zero in as quickly as possible on what is wrong with a situation. What's the worst part of this job? What's the part of this job you hate? Who are the kinds of people that would do terribly in this profession?

[00:04:03] And if you can ask a lot of smart people those questions, it helps you weed yourself out early on and save yourself a lot of trouble and heartache if something is not going to be a fit for you. But absolutely, if you can find a way to do informational interviews, if you can find a way to experiment and sit in on meetings or do a test run or do an internship or volunteer somewhere, or take on a targeted project that you're running for free as an experiment. Those are all great ways to see if the world you're entering is one that you would enjoy. 

[00:04:36] Matt Abrahams: Looking for the things that don't fit, I think is a great way to help you find fit. Thank you for that. I know you're very proactive by nature. You emphasize the importance of being proactive in our careers. What specific actions can we take today to ensure that we're actively managing our career paths in the future, rather than just waiting for opportunities to passively come to us?

[00:04:59] Dorie Clark: Yeah. So I think this is another important point because the truth is, it sounds exhausting to say, oh, how do you be proactive every day? You know, a lot of times people might hear that and say, wow, I don't even have the energy for that. I barely have the energy to get through the meetings on my calendar. I'm going to be proactive about my future every day. My sort of reframe is, we need to be proactive periodically. We don't actually need to be proactive every day, thank goodness. For me, a lot of it, as the author of The Long Game, I am a supporter of the idea of taking a step back periodically and taking inventory and looking at our career arc, but there are intervals where this is appropriate.

[00:05:40] This varies for different people, but I would say maybe quarterly, it's useful to actually take a bigger step back and say to yourself, is the path that I'm on now, the activities that I am pursuing, the job that I'm in, if left to its own devices of just rolling forward and making a sort of reasonable but not exceptional amount of progress, where would this logically lead me? What is the most logical outcome and is that something that I feel happy about? Or is that something that would be troubling to me? And if it is troubling, then we need to pause for a minute and say, what do we need to do? Is it that you need to volunteer to take on more responsibilities so that you can be seen to be more of a leader so that you can accelerate your promotion track?

[00:06:24] Is it that actually the type of role that I'm in really isn't a fit and maybe I need to start networking to make friends with people in other departments so that I can make a transition? Is it that the goal that I want is something that's not going to be accessible to me unless I have an advanced degree and maybe I need to go pursue that? There's a lot of things that we can stop and ask ourselves, but that's something that maybe twice a year, maybe four times a year is useful to inquire about. On a shorter time frame, it's more about execution. Every Friday, look at the calendar for the week ahead and say, great, is my calendar filled with meetings that I should be in, or should I not be in these meetings? Do I not need to be there? Can I cancel some of them? Can I create some white space in my calendar? Those are good questions on a weekly basis. 

[00:07:07] Matt Abrahams: Thank you for taking us through both the longer term and the shorter term, and I love the very actionable steps that you talk about. In many ways, managing your career is like managing a business. You know, every quarter you would do a quarterly review of where we're at, where we're going, what changes do we need to make, and that's the advice I hear you giving, at least in the longer term. And in the shorter term, it's, you know, what's filling your time and what can you do to accelerate where you want to be and what are some of the things you could remove that perhaps aren't helping you. You know, a lot of us stay in our jobs just based on inertia. You know, we don't consider job changes until something happens to motivate us. For example, the company reorganizes or there's a big negative event that happens. In your experience, how can we cultivate a proactive job seeker mindset? 

[00:07:53] Dorie Clark: One of the ways that I think about this is what I call the difference between lowercase r, reinvention, and capital R, reinvention. Ultimately, there's a fairly growing recognition that we all do need to reinvent ourselves in general, whether it is because sometimes people make rather dramatic career changes or just the fact that we need to keep up, you know, the world is evolving quickly and so we need to make sure that our skills are. That we're not just relying on things we learned when we were twenty-two and then, oh good, now we're set for forty years, fantastic.

[00:08:27] What I would encourage people to do is to try to adopt, in their own lives, the lowercase r reinvention. And basically what this means, the big flashy capital R reinvention is about those dramatic moments when you're making a big change. And that's important. You know, obviously you need to be smart and lean into that when it happens, but those are things that occur fairly rarely. If we want, however, to be ready at a moment's notice, to capitalize on opportunities, to pursue new things that are interesting, to be nimble if there's a change or a reorg or something like that, we need to make reinvention a habit. We need to get so comfortable with the idea of, okay, I'm going to learn something new.

[00:09:09] I'm going to try something new. I'm not wedded to some particular identity that I have. That becomes a habit and a way of life rather than, oh, I'll just change when I have to. And embracing that mindset and saying, okay, this is just a thing I do. This is not something special, this is not something extraordinary, this is just how I am and how things are, makes it a lot easier for us to take things in when we do face changes down the road. 

[00:09:40] Matt Abrahams: Again, distinguishing between the big R and the little r of reinvention helps just like thinking long term and short term. I like that idea of making it a habit. What do you think is the best way to learn about a career path or industry that you're just not familiar with, but you think there might be something there for you?

[00:09:57] Dorie Clark: Yeah. If you're experimenting and trying to learn about an industry where you haven't worked in it, you don't have a ton of contacts, there are a lot of decent starting points. One, if you really don't know anyone, is actually literature. Because there are a lot of very interesting memoirs that have been written about almost every field that's out there. Oh, you want to learn about the restaurant industry? You want to learn about the world of high stakes media? All of these have nonfiction that has been written about those worlds, and oftentimes first person experiences, where you can begin to see, oh, here's what it's like, and here's the sexy parts, and here's the terrible parts.

[00:10:38] And like my mother used to always tell me about marriage, right? There's nothing without flaws. It's about finding which flaws you can live with. And I think it's similar for careers, right? The flaw that you can live with, that you have to work hundred hour weeks, or is that a flaw that you're like, absolutely not. I will do anything to avoid that. And with more data, you can choose accordingly. But certainly I'm a big fan of informational interviews and LinkedIn is great, of course, for that, because you can find people who are, maybe you don't know them personally, but they could be second degree connections that you could potentially reach out to and get an introduction to. You could potentially find alumni links, people who went to your same university, your graduate program, and they might be more willing to connect with you and offer some advice. So those are some useful resources as well. 

[00:11:26] Matt Abrahams: I love your mother's saying. My mother had a very similar saying. She said everybody has baggage, you just want to find somebody that's got matching baggage. And I think the same thing is true with, with work as well and most of the things that we do. When considering a career change, how can we assess the transferability of our current skills to new roles and industries? Are there specific exercises or tools you recommend to help us see how what we have or possess, in terms of skills and best practices, apply elsewhere?

[00:11:55] Dorie Clark: This is an area, certainly, where I think tools like AI can be very helpful, actually. Feed in your resume. Say, hey, if you were going to brainstorm, tell them, find me fifty careers that use my underlying skills where I could apply them. And it can probably brainstorm some interesting things. That's not a bad way to begin the conversation and just get a bunch of wild ideas. I think once you have a pretty large list, then you can begin whittling it down and saying, which of these am I actually interested in? What's useful here? But the biggest point that I want to make here is related to your question, Matt, about mindset, which is that we have to recognize job one here, is understanding that most people around you, even your family, your friends, your theoretically biggest supporters, will probably be relatively uncreative when it comes to understanding how your skills transfer.

[00:12:51] People just don't see it. It's very hard for them to piece it together. That, oh, you used to do this, but now you can do that. On their own, they are not going to intuit that, oh, of course, of course, you can make that leap. You have to almost treat them like a constituency where you are making the case that you are able, you know, I did this, I will be able to do this other thing, it is transferable. They may not necessarily see it, and so we have to recognize, we have to make them see it. 

[00:13:25] Matt Abrahams: So we actually have to be very active, seeking input from other people, we have to be active and take the right perspective on the information we get. They might not be that creative. And I love the idea of using tools and artificial intelligence to be a guide and help as you go through this process. As you know, this is a podcast series in collaboration with LinkedIn. I would be remiss if I did not take a personal branding expert like yourself and ask you, what are some of the things that we can do in terms of how we position our brand out there in the world on tools like LinkedIn? Are there certain things we should be looking to put out there that can help? Or are there things that we should avoid putting out there? What, what's your thought on how we show our brand in something like LinkedIn?

[00:14:10] Dorie Clark: Of course, I mean, by now everyone knows the basic, don't put things online that can disqualify you. So I think, I think we're probably pretty set on that. One thing that I think a lot of people forget sometimes is the idea that you need a lot of repetition if you are making a career change in particular. Because the truth is, most people are not paying very close attention to you. If they're an acquaintance, they have a fairly fixed idea of, oh, yeah, she's the person who does X. And that's great, but it's going to, it's going to actually take more than one iteration for you to reinforce for them that, no, no, I don't do X anymore, I do Y, or I want to do Y.

[00:14:53] And these people, in your kind of network of casual acquaintances, are going to be the ones that are probably, honestly, most helpful to you in your career search. Because they are the ones who have a wide range of connections externally that you don't know, but maybe you want to know. Maybe they're helpful to you. So you need them to have it top of mind that, oh, she's looking for opportunities in this new realm. What social media and LinkedIn in particular is very good for is that form of repetition. If you were doing this in person, you might really bore somebody if you kept talking about the same thing. But over time on social media, if once a week you are doing a post where it's focused on the new industry that you're wanting to break into. Oh, I wrote this, you know, let's say you want to go to Fintech.

[00:15:36] Okay, great. I wrote this article about the future of Fintech. Amazing. You do that, the next week, oh, I was just listening to this amazing podcast talking about new issues related to whatever particular finance thing. Oh, you know, because I'm focused on Fintech, this is so interesting. Maybe you'll find it interesting too. And you put it out there and you keep reinforcing and that's how it sticks in people's minds. And that's the prerequisite, right? If they're going to help you, they need to know what you're doing so that they understand how they can help you. And social media is great for enabling that osmosis to happen where they grasp what you're up to now.

[00:16:14] Matt Abrahams: Being strategic about what you post and repeating key themes is something that I think is a really golden nugget that you shared there. We want to think about how we present ourselves, obviously, in a way that puts us in a positive light, demonstrates the skills we have. But through repetition of being strategic in what we post, what we like, what we repost, can certainly help that broader set of our network to help us. I really appreciate that. Dorie, this has been great. Before we end, I'm asking everyone who joins me as part of this Catalyzing Your Career miniseries the same two questions. Are you up for those? 

[00:16:47] Dorie Clark: I am up for it. 

[00:16:48] Matt Abrahams: Okay, I'll be very curious about this. What is the best career advice you have ever received and why? 

[00:16:54] Dorie Clark: So the best career advice that I've ever received, honestly, pre COVID was, Dorie, you don't have to have an office. You can work from home. And everyone subsequently has discovered that this is a fantastic idea, but I have saved so much money from doing it over time, because 2000's, which is when I started my business. An office was actually seen as this kind of marker of credibility, like, oh, you're not serious unless you pay for an office. And speaking of branding, that's a really interesting idea, that so often we feel this need to establish our credibility through these external things. Oh, they won't take me seriously unless I have this, or unless I buy that. And oftentimes, it's like, no, that's completely ridiculous. Where you work has no bearing on your skill, on your professionalism. And so hearing that early on was very useful to me, in terms of rethinking, all right, where do I want to put my time and energy in my budget? 

[00:17:56] Matt Abrahams: Going back to what we talked about earlier about hypothesis testing, it can help you focus the hypotheses you have, you know, if you're saying I don't need to have a physical office. That opens up a whole world of tests you can run versus not. And the point you just made about these external credibility markers. I think we all have to think about that. I talk to many people who come to me and say, I want to write a book. And I say, why do you want to write a book? And they'll say, because it gives me credibility. And I am thinking there's so many other ways, the amount of effort and time it takes to write a book. Write a book if you're really passionate, you want to write a book. Don't just write a book because you want credibility. So I think that's important for all of us to think about. In your case, it was office space, and I think all of us think about these things we need to do, we think, to have that credibility. 

[00:18:39] Final question. What is one thing you wish you would have done differently in the way you managed your career? 

[00:18:46] Dorie Clark: So one thing that I wish I'd done differently when, when it comes to my career is, you know, I write about mentorship and learning from other people. This is a thing that I, I feel excited about and that I think is really valuable. But I honestly have not done it enough myself. I have had to cultivate a lot of peer mentors, which is great. And I love that. I think that's very important, but it's because, perhaps, because I was not in a circumstance to organically find them. Or also perhaps because maybe I just wasn't that good at it. I didn't really have a lot of luck cultivating older mentors. And so I feel like a lot of what I've had to figure out, I kind of figured out on my own. And so I found workarounds, but I do wish that I had, um, perhaps been a little bit more skilled at how to cultivate that, that piece of the equation.

[00:19:44] Matt Abrahams: Mentors are phenomenal. And I would say that's a big mistake I made too, is not trying to find those mentors. I have relied a lot later in my career on mentors, but early on, I would have liked to do the same thing. So thank you for reminding all of us to seek mentors and there are lots of ways to find them. Dorie, thank you for mentoring us and helping us to see that our career is something that we can manage. And that we need to be taking chances and testing our hypotheses all along the way. I really appreciate the very specific guidance on the behaviors we can take, as well as the adjustments we need to make to our mindset. Thank you. 

[00:20:19] Dorie Clark: Matt, thanks. 

[00:20:22] Matt Abrahams: Thank you for joining us for this Catalyze Your Career miniseries episode sponsored by LinkedIn. Be sure to tune in to the other two episodes in this miniseries. You can learn more about LinkedIn's Job Match feature at Linkedin.com/jobs. This episode was produced by Ryan Campos, Shelby Merryweather , Aech Ashe, and me, Matt Abrahams. Our music is from Floyd Wonder. With special thanks to LinkedIn and Podium Podcast Company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Also, follow us on LinkedIn and check out fastersmarter.Io for deep dive videos, English language learning content, and our newsletter. Please consider our premium offering for extended Deep Thinks episodes, AMAs, Ask Matt Anythings, and much more at fastersmarter.io/premium.