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

Rethink career success by testing, adapting, and staying open to unexpected opportunities. Career planning isn’t as straightforward as we often assume—but according to Dorie Clark https://www.fastersmarter.io/guests/dorie-clark/, that’s actually a good thing. Instead of following a rigid path, she believes we should be “treating our careers like a series of experiments”—testing, iterating, and staying open to unexpected opportunities. "People assume they need to have everything mapped out for the next twenty years," Clark explains. "But in reality, careers are built through testing, learning, and adapting—just like a scientific hypothesis." As a bestselling author and career strategist, Clark has spent years studying how professionals can future-proof their careers in an unpredictable world. She shares why informational interviews, LinkedIn strategy, and quarterly career check-ins are essential tools for anyone looking to make a career shift. “You don’t want to be so mired in your plan that you can’t take advantage of unexpected opportunities,” she says. In this episode of Think Fast, Talk Smart https://www.fastersmarter.io/, Clark joins host Matt Abrahams to challenge traditional career advice and explore strategic personal branding, the power of weak ties in networking, and why “reinvention isn’t a one-time event—it’s a habit.” This episode is brought to you by LinkedIn. Explore your job potential at Linkedin.com/jobs http://linkedin.com/jobs. Episode Reference Links: Dorie Clark https://www.fastersmarter.io/guests/dorie-clark/Ep.118 Maximizing your Personal Brand: Communicating Who You Are to Help Get What You Want https://www.fastersmarter.io/118-maximizing-your-personal-brand-communicating-who-you-are-to-help-get-what-you-want/ Connect: Premium Signup >>>> Think Fast Talk Smart Premium https://www.fastersmarter.io/premium/Email Questions & Feedback >>> [email protected] Transcripts >>>Think Fast Talk Smart Website https://www.fastersmarter.io/187-experimenting-failing-and-finding-your-job-fit-catalyze-your-career/Newsletter Signup + English Language Learning >>>FasterSmarter.io http://fastersmarter.io/Think Fast Talk Smart >>>LinkedIn https://www.linkedin.com/company/think-fast-talk-smart/,Instagram https://www.instagram.com/thinkfasttalksmart/, YouTube https://www.youtube.com/playlist?list=PL6caGRBUYZCmgDGM2RK6mxKB9jG_ccmm3Matt Abrahams >>>LinkedIn https://www.linkedin.com/in/maabrahams/ Chapters: (00:00) - Introduction (01:31) - The Importance of Long-Term Career Vision (03:03) - Testing Your Career Hypothesis (04:36) - Being Proactive in Your Career (07:07) - Reinvention: Small vs. Big Career Changes (09:40) - How to Explore a New Industry (11:26) - Transferring Skills to New Careers (13:25) - Optimizing Your Personal Brand (16:48) - Best Career Advice Received (18:39) - Career Regrets & Lessons (20:22) - Conclusion ******** Thank you to our sponsors. These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost. Learn more about how Notion https://www.notion.com/?utm_source=podcasts&utm_medium=thinkfast can support your business at notion.com/thinkfast. https://www.notion.com/?utm_source=podcasts&utm_medium=thinkfast Join our Think Fast Talk Smart Learning Community and become the communicator you want to be. https://learning.fastersmarter.io/?redirect_from=podpage

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Matt Abrahams?

  In the moment, conflict is difficult for everyone. In our October newsletter, out now, you will learn ways to help yourself handle these challenges better. Not only do you get specific advice, we're also providing an infographic to help you remember. Find our newsletter on the Think Fast, Talk Smart LinkedIn page or at fastersmarter.io under Resources.

• 0:27Matt Abrahams?

  What if we saw our career is 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 mini-series 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 mini-series that was distilled down from a LinkedIn

• 1:11Matt Abrahams?

  live event that I did with Catherine Fisher, where we answer live career questions from you, our audience. Today, I'm really excited to talk again with Dorie Clark. Dory and I had a really thoughtful conversation about personal brand and our careers in episode 118. As a reminder, Dory is a consultant, speaker, lecturer, and author. Among her many books are Stand Out, Representing You, and her latest, The Long Game. Welcome back, Dory. You provided so many useful and actionable ideas last time we met, I'd love to hear even more.

• 1:47Speaker 01

  I will do my best, Matt. Thank you for having me.

• 1:50Matt Abrahams?

  All right. Are you ready to get started?

• 1:51Speaker 01

  Amen. Let's do it.

• 1:53Matt 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?

• 2:04Speaker 01

  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 20 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 20 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. And I want to actually encourage people to reframe this. I prefer the terminology provisional hypothesis

• 2:48Speaker 01

  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.

• 3:25Matt 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?

• 3:42Speaker 01

  I'm a big fan of testing hypotheses because there's a lot 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 question is. 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?

• 4:25Speaker 01

  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.

• 4:58Matt 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?

• 5:21Speaker 01

  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. This varies for different people, but I would say maybe quarterly.

• 6:06Speaker 01

  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? Is it that actually the type of role that I'm in really isn't a fit?

• 6:50Speaker 01

  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 timeframe, 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.

• 7:29Matt 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 then 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?

• 8:15Speaker 01

  One of the ways that I think about this is what I call the difference between lowercase r reinvention and capital R reinvention. And 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 22 and then, oh, good, now we're set for 40 years. Fantastic. What I would encourage people to do is to try to adopt in their own lives, the lowercase r reinvention.

• 8:56Speaker 01

  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. I'm going to try something new. I'm not wedded to some particular identity that I have.

• 9:36Speaker 01

  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.

• 10:01Matt 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?

• 10:19Speaker 01

  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. And

• 11:01Speaker 01

  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 100-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

• 11:46Speaker 01

  useful resources as well.

• 11:48Matt 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 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?

• 12:18Speaker 01

  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 50 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

• 13:01Speaker 01

  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. 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

• 13:44Speaker 01

  see it, and so we have to recognize, we have to make them see it.

• 13:48Matt 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's your thought on how we show our brand in something like LinkedIn?

• 14:32Speaker 01

  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 gonna, it's gonna 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. And these people, your kind of network

• 15:17Speaker 01

  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. Okay, great. I wrote this article about the future of fintech. Amazing. You do that.

• 16:02Speaker 01

  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.

• 16:36Matt 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 and 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. We'll be right back to finish our conversation. But first, we're going to take a quick break for a word from our sponsors. Their support covers the cost of production, so we can bring you this show for free.

• 17:11Matt Abrahams?

  This podcast is sponsored by Squarespace. The best communicators don't just get their message across, they make it easy for people to know what to do next. Your website can do the same thing. With Squarespace, you can build a polished online presence that clearly shows people who you are, what you offer, and how they can work with you. If you offer coaching, consulting, classes, or other services, Squarespace lets you showcase those offerings, take payments, and use Acuity Scheduling so people can book time with you directly. And with built-in analytics, you can see how people are finding and engaging with your site, helping you make smarter decisions about where to focus. So your online presence doesn't just look professional, it helps people take action. Go to Squarespace.com/thinkfast

• 17:56Matt Abrahams?

  for a free trial. And when you're ready to launch, use offer code THINKFAST to save 10% off your first purchase of a website or domain. Hi, Matt here. Sometimes the biggest obstacle to getting something done isn't the idea, the plan, or even the budget. It's finding the right person to help you execute. And the longer that takes, the easier it is to lose momentum. That's where today's sponsor, Upwork, can help. Upwork gives businesses fast access to highly skilled freelance professionals across areas like marketing, design, software development, AI, and business operations. And with Business Plus, you can access the top 1% of talent on Upwork. AI-powered shortlisting

• 18:37Matt Abrahams?

  gives you a curated list of freelancers matched to your goals in under six hours. So you can spend less time searching for the right person and more time actually moving the work forward. Visit Upwork.com right now and post your job for free. That's Upwork.com to connect with top talent ready to help your business grow. That's U.P.W.O.R.K. dot com. Upwork.com.

• 19:03Matt Abrahams?

  Dory, this has been great. Before we end, I'm asking everyone who joins me as part of this catalyzing your career mini series, the same two questions. Are you up for those?

• 19:12Speaker 01

  I am up for it.

• 19:13Matt Abrahams?

  Okay, I'll be very curious about this. What is the best career advice you have ever received and why?

• 19:19Speaker 01

  So the best career advice that I've ever received, honestly, pre-COVID was, "Dory, 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 if we go back to the mid 2000s, 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

• 20:01Speaker 01

  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?"

• 20:21Matt 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 and 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. Final question.

• 21:06Matt Abrahams?

  What is one thing you wish you would have done differently in the way you managed your career?

• 21:11Speaker 01

  So, one thing that I wish I'd done differently when it comes to my career is, you know, write about mentorship and learning from other people. This is a thing that 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

• 21:56Speaker 01

  own. And so, I've found workarounds, but I do wish that I had perhaps been a little bit more skilled at how to cultivate that piece of the equation.

• 22:08Matt 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. Dory, 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.

• 22:44Speaker 01

  Matt, thanks.

• 22:45Matt Abrahams?

  Thank you for joining us for this Catalyze Your Career mini-series episode sponsored by LinkedIn. Be sure to tune in to the other two episodes in this mini-series. You can learn more about LinkedIn's JobMatch feature at LinkedIn.com/jobs. This episode was produced by Ryan Campos, Shelby Merriweather, H. Ash, and me, Matt Abrahams. Our music is from Floyd Wonder. With special thanks to LinkedIn and Podium Podcast. 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,

• 23:29Matt Abrahams?

  and our newsletter. Please consider our premium offering for extended Deep Thinks episodes, AMAs, Ask Matt Anythings, and much more at fastersmarter.io/premium. Before we wrap up, I just want to say thank you for listening. It really means a lot to hear how people all over the world are using these ideas in their own lives. It inspires me and the whole team that brings you this show. If you want more episodes and resources, feel free to follow, subscribe, and explore past conversations. We're grateful for your support of Think Fast, Talk Smart.