A Q&A with Tess Vigeland

August 26, 2015


We sent some overly long questions to Tess Vigeland, and she replied with some wonderful answers.

"I'm now a strong advocate for giving yourself some time—as much as you can—before moving on to the next thing. The way we do it now—going from the current job on Friday to, BAM!!!, the new job on Monday is insane. Why do that to yourself? Plan so that you have some breathing room either before a transition, or while you're in a longer transition figuring out what's next." —Tess Vigeland

Yesterday, we introduced you to Tess Vigeland (if you didn't already know her from her anchor work on NPR's Marketplace), and shared an article she wrote about How to Know When You've Gotta Go. Having left her dream job at Marketplace, she knows something about the topic, and her instincts as a journalist led her to find and intertwine the stories of others in her new book, Leap: Leaving a Job with No Plan B to Find the Career and Life You Really Want. We really loved the book because it is intensely personal, and doesn't hide the self-doubt or fear in the process (more on this below), but also because well... it's Tess Vigeland, and she's just really entertaining (more on this below, as well). My wife and I listened to Tess Vigeland every single weekend for years, so please forgive me if I get a little wordy or gush a little in the questions below.

800-CEO-READ: I know you aren't going to tell the story of what prompted you to leave your dream job at Marketplace (as you say in the book, there's no possible upside in it while the downside is quite real). I also know that you don't have a specific, concrete answer to the question you get asked most often these days: "How do I know when it's time to leave?" Though I do love your advice that "If you're asking yourself the question, it's well past the time to start exploring the opportunities." So, if you won't tell us exactly why you left, or when others should leave, but seem to have done a really good job in deciphering how you left, can you offer some other advice on that question? Not the when or why, but how to leave a job? In addition to the wise move of not burning bridges, you share a few stories in the book, including your own, in which someone assumes they'll use the time in between their notice and their actual leaving to network and search for new opportunities, only to become so involved in the transition that this important groundwork is left unlaid. How can people make sure that doesn't happen, or is it really that important?

Tess Vigeland: Okay, at first I thought you were asking the how-to-leave-with-dignity question that I would always answer with a simple "Be an adult and not an ass about it!" (Can I say that in a Q&A?) [Yes, she can] The question you're actually asking is more nuanced. Part of it depends how long you give yourself between saying you're going to quit... and quitting. I gave three months' notice and figured, hey, I'll have my future figured out before my final day in the office, no problem. But OF COURSE those became the busiest three months I'd had in years. It was great in one way because it kept my mind off of the fact that I was about to be un/self-employed (I called myself unemployed on social media for months and friends would yell at me because I was freelancing and thus self-employed, so they thought I was being ridiculous, and I was).

But, in another way, I probably could have been using my down time more productively: networking, looking at job boards, blah blah blah. That's what you're supposed to do. But honestly, I'm glad I didn't have time to do that stuff. Because it would have distracted me from doing a good job at work, and it probably would have added to the sense of panic I had about not having anything lined up. And in the end it was a good thing NOT to have anything lined up, because it gave me the headspace to sit with the uncertainty and really figure out what the next move might be and what I wanted my life to look like. That's much harder to do in the middle of winding down a job. That's why I'm now a strong advocate for giving yourself some time—as much as you can—before moving on to the next thing. The way we do it now—going from the current job on Friday to, BAM!!!, the new job on Monday is insane. Why do that to yourself? Plan so that you have some breathing room either before a transition, or while you're in a longer transition figuring out what's next.

8cr: If you do make a leap without knowing exactly what you're going to do next, how can you make sure you're maximizing both your effort and enjoyment during the process? And how can you assuage the feelings of guilt that you may not be conforming to others' notion of productivity?

TV: First of all, stop giving a... hoot... about whether you're conforming to what you're supposed to be doing, what others think of as productivity. They're not living your life, and we all need to stop caring so much about what other people think. Easier said than done, I know. Gets easier as you get older! You need to find your own balance of being productive: doing research on other career fields, talking with people and maybe even visiting them at their jobs to see how it "really works," and yet also taking advantage of this time to enjoy the hours you're not working. Someone asked me recently "Well what if I end up watching TV all afternoon?" as if that was a venal sin. It's not, and if that's what relaxes you, if that's what you've been longing to do your entire working life, then I say go for it. Do what brings you some element of joy, rest, and relaxation. I personally would rather be outside hiking with my dogs, or learning a new element of photography, but I'm tired of people thinking there's a right way or wrong way to spend your time away from work. And I think stretches of non-productivity can be good, and can crank the creative wheel in ways you might not even realize. So as I say in the book, give yourself a freaking break.

If it helps you, go ahead and map out your days so that you know when you have structured work time, and when you have structured free time. That doesn't work for me, except in the broadest sense (I'll work in the morning, and then I'll go work on my photography for fun in the afternoon)—but I think you have to figure that out for yourself. Experiment and see what works for you in terms of motivation.

Now some "experts" will raise their hands and stomp around and say you can't do this because future employers won't hire you and you'll get lazy. Please feel free to ignore them. Do you even want to work for someone who judges you based on the fact that you took some time out to decide your next move? I don't. And just because you take a time out, just because you take a leap, doesn't mean you'll fall down, hit your head, and forget everything you've ever learned. We need to stop seeing sabbaticals, leaps, time away, as weak and dangerous to your career prospects. I'd like to see the proof that it turns you into a potato.

8cr: You mention that the blanket support you received from family and close friends when telling them you were quitting and the excitement everyone expressed for what you were going to do next sometimes had the opposite effect on you than one might imagine—that it isolated you in a way and made you more nervous about what, exactly, it was you would do next. Why is that, how have you overcome it, and what advice would you give those close to others who want to support someone making such a leap?

TV: I think it's because I had so much self-doubt that I couldn't let myself believe that they were being anything but nice, offering obligatory support because that's what friends and family do. And sure, that's probably partly true, but I think the people who know you best are likely also realists and they see from the outside that you're smart, successful, and they know you'll figure it out. I overcame it with time, and with deeply honest questioning of these people, especially my parents, and I was able to do that mostly because I had the excuse of "I'm doing it for the book." But one thing you might consider doing before your leap is gathering what a good friend of mine calls a "Personal Board of Directors"—people you trust implicitly to be brutally honest with you and help evaluate your decision-making. They're NOT your best friends. But they know you and they know a little bit about what you want from life. Ask 3-5 people if they'd be willing to serve for, say, six months to a year, and have quarterly calls with them to tell them what you're up to and get their feedback.

As for you who are the friends and family, I say keep doing what you're doing. Keep expressing your support and your faith in your leaper. They may receive that the way I did, with a cocked eyebrow and hefty dose of skepticism, but that's okay. Keep going. They need to hear unconditional, unwavering support and they'll eventually come around to believing you.

8cr: You're very candid about the self-doubt and fear that accompanied your leap. I found that really refreshing, especially after years of reading the ah-rah advice to just get out there and change the world that so many authors offer those looking to escape their nine-to-five. Did you make a conscious decision to pull back the curtain on those fears so fully, or is it perhaps just the difference of you being a journalist who has learned to be more cynical and honest than, say, a serial entrepreneur who has a rosier, more grandiose view of how easy it will be for people to "just make it happen?"

TV: On the contrary I think journalists are trained NOT to be honest about themselves—it's the whole "BE OBJECTIVE AT ALL TIMES BECAUSE YOU ARE A ROBOT WITHOUT FEELINGS OR OPINIONS" thing. So my first instinct was to just be a reporter and not talk about myself at all and certainly not be emotional about it. But two things changed my mind. No, three. First, I've watched the proliferation of personal blogs and essays all over the Internet and even within mainstream media. When people like the late, great New York Times columnist David Carr are spilling their guts all over the place (his The Night of the Gun is extraordinary) and audiences are lapping it up, you take notice. Second, the most and best reaction I would get after a report or show aired at Marketplace was after I'd done an interview or a call-in segment that featured some sort of emotional moment. A moment of vulnerability, of empathy, of baseline realness. Of me, and the guest, being real, being human, and being present with each other. That feedback was a window into what people want to hear/read/see/experience. And third, I gave a speech several months after leaving my job in which I was at my most raw, vulnerable, and honest, in front of 3,000 strangers. I expected people might be bummed out by it, but instead, they jumped to their feet and applauded my Truth. They applauded my messy, imperfect, failure-strewn Truth. They got it, and they appreciated it. And that's the lesson I took into writing the book. That doesn't mean I haven't had a few panic attacks when I think about some of the things I've disclosed about myself in the book. But it's too late to change it now!

And I think "just make it happen" is dishonest and sets people up for disappointment.

8cr: I love the story of Adam Ragusea telling you that "People don't love you for personal finance. People love you 'cause you're the lady who lives in the radio.'" It made me think of how my wife and I used to listen to the show every weekend, and it wasn't because I need personal finance advice (I get enough of that here at work), but because you made it all so relatable and remarkably entertaining. In short, you know how to tell a story, even if it was in conjunction with a caller asking for advice about their personal financial story. This was true in spite of the fact that, as you say in the book, there are only about six stories in personal finance. I guess what I'm asking here is, how do you do that? Where/how did you develop that ability?

TV: You are too kind. (more, please...) No, no, stop, really, you are much too kind. (more, please...) I would be remiss if I didn't credit the best editors and producers in the business who wrote scripts, found guests, prepped segments, and made me sound great. Nobody outside the newsroom has any idea what a team effort it really is, and if the show was just me, myself, and I, you wouldn't listen. Same with any piece of radio I've ever done.

That said, I guess part of it is that I always tried to take the stance of learning along with the audience. I avoided becoming the expert on my own show, because I wanted to be the voice—and the experience—of the listener. I considered myself to be their proxy at all times. The farthest thing from my mind was showing off what I knew. That wasn't the point. I tried to ask the "stupid" questions because I knew they were the questions everybody else had but was afraid to ask. So I think part of why it was relatable was that I was taking the journey WITH you. Who doesn't want validation of their own foibles and concerns?

As for being entertaining, well, Milton Berle was my dad and my mom is Amy Schumer, so... LOL JK! ( I've learned how to speak Millennial.) We did a lot of work behind the scenes to try to figure out how to take a really dull topic—c'mon, admit it, 401K'S ARE DULL—and make it so that people wouldn't turn off the radio. I took an improv class a few years ago that I think helped a lot (I learned to "yes-and" the callers!). And honestly, I just stopped taking it all so seriously all of the time. If Dan Savage can make people laugh about the funny things that happen during sex, then I could certainly try to make people laugh about the absurd things they do with money. Not that I'm Dan Savage. But to quote Joan Cusack in Broadcast News, he's my role model.

"I always tried to take the stance of learning along with the audience. I avoided becoming the expert on my own show, because I wanted to be the voice—and the experience—of the listener. I considered myself to be their proxy at all times."


Read more about Ms. Vigeland and How to Know When You've Gotta Go in our first installment from yesterday.


Come back tomorrow as we wrap up the series with a few questions about our bread and butter—business and books.

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