Lindsey Pollak ’96 is a New York Times bestselling author and expert on the subject of careers and the workplace. When the COVID-19 pandemic turned a calendar bursting with workshops, speaking engagements, and appearances into a calendar filled with … well, pretty much nothing, she turned all that suddenly-freed-up time into an opportunity to write her fourth book. Recalculating: Navigate Your Career Through the Changing World of Work was published by HarperCollins on March 23, 2021. Focused on the possibilities for career and lifestyle reassessment and re-invention opened up by pandemic disruption, the book offers advice, guidance, and salutary stories about people who have pushed the “reset button” on their lives. Recently, Lindsey (whose calendar once again has very little white space) managed to squeeze in a little time via Zoom to summarize her own career, the themes in her latest book, and the way she came to write it.

YW: How did “Recalculating” come about?

LP: What's always driven me to write books is that they’re books that I wished I’d had when I was going through things. For instance, my first book, Getting from College to Career, was what I needed when I was trying to figure out what to do after college. My second book, Becoming the Boss, was the one I needed when I started to manage people. And so on. So this book was born March 20, 2020, when lockdown started and my calendar went from completely booked to completely empty in a two-week period. I started picking up the phone and calling people and saying, ‘What are you doing? How are you handling this? What's going on?’ No one knew. And I guess it was my literary agent who said, 'Sounds like there's a book in there.' Because, suddenly, through no fault of our own, we had to recalculate.  So what does that look like and what does that mean? That’s how the book was born. And I wrote it in three months so that we could get it out as quickly as possible. I started it about a year ago in May of 2020, and it came out in March of 2021, which is pretty quick for publishing.

YW: Amazingly fast. But—while the pandemic certainly isn’t over—it seems that things are opening up again and we may even be coming back to a more normal life of travel, meetings, and even going back into the office. Is your book relevant in a post-COVID world?

LP: Absolutely. I think the trends that the pandemic accelerated had been building for a long time: fully remote work or hybrid work patterns; people having ‘portfolio’ careers where they do many different things; a greater emphasis on digital communication; and far more entrepreneurship and self-employment. COVID did not launch these trends. It accelerated them, and solidified them. There are different types of opportunities out there and new ways people have to go about capturing them.  For example, I’ve been told by many recruiters that companies are not going back to all in-person interviewing of job candidates. They are going to continue to use virtual interviews along with in-person ones. So if you’re job hunting, you now have to know how to handle both. You have to have a LinkedIn resume and the old formal resume. How to make your points on Zoom as well as in person. And that’s just the mechanics of job-hunting. There’s a lot more that has changed quickly and permanently.

YW: OK, point taken. I guess this is a book for the "new normal"—and for getting yourself back to a "new normal". So tell me, how can people do that?

LP: I have what I call five rules for recalculators. The first is to embrace creativity. Right now is not a time to be rigid. You might need to think about industries you’ve never thought about, or opportunities like entrepreneurship or consulting or freelancing that you hadn’t considered. I tell the story of a chef, who obviously couldn’t pursue his career during the early days of COVID. And—I hear this a LOT—he was saying that he’d really been thinking about a change anyhow, and COVID kind of prompted him to do that more seriously. So he went back to his college career center, which I always recommend, and they asked him, 'What do you like about being a chef?' And while he liked cooking, what he really liked the most was managing people and ordering the ingredients, getting everything set up. The career counselor said, 'You know, that sounds a lot like logistics, which is a big growing field.' And the chef realized that he had a lot of experience in a field that he just had never identified being good at. So now he’s transitioned to logistics and has made cooking his side gig. It was all because he was willing to think creatively about his skill sets. 

The second rule is to prioritize action. And I think where a lot of people have gotten stuck is that they get paralyzed by the situation that we're in, which is there are no jobs. 'I'm too old, I'm too young, I don't have the skills, I don't know how to code'… whatever it is they’re telling themselves, they just sort of drop out of the process. I do these online webinars, and the number one question I've been getting recently is ‘How do I motivate myself when I'm feeling really down?’ And my answer is you take the tiniest step you possibly can. It's really about action. You have to be of the mindset that you’re going to do something, whether it's updating one word on your LinkedIn profile today or calling one alum from Yale.

Rule number 3 is control what you can. Look, you can’t control a lot of things. People get obsessed with being too old to find a job or being less qualified for a job than other people, and the reality is, you can't control things like who else is applying for the position. You can't control whether the other people perceive you the way you’d like. But what you CAN control is your attitude and your willingness to move forward. You can control the number of jobs you apply for, and the number of people you speak to. And that’s good, because it really is a numbers game.

The fourth rule is to know your non negotiables. I think a lot of people make the mistake of saying, 'I'll do anything. You know, it doesn't matter.' And that's not really very helpful and often not true. And I think particularly as women, we have to know what our bottom line is. Is it that you need flexibility because you have elderly parents or you have children? Is it that you need a certain salary? Is it that you learned during the pandemic that you love working from home and want to continue—or you hated working from home and don't ever want to do it right? It's all valid, but you have to identify either one or two things that you absolutely will not end on, because I think we’ve often bent too much. It might not be your dream job, but if you can satisfy the non-negotiables, you can move forward.

And the fifth and final rule for recalculators: ask for help. You can't do this stuff alone. You've got to ask people for advice. You've got to go to webinars. You've got to read publications. I think the best way to feel comfortable is to know that you’re also willing to give help. That’s empowering. I did a lot of training for LinkedIn and the one of the founders of LinkedIn, Reid Hoffman, actually recommends going into LinkedIn and thinking, who can I help today? Because if you're known as a helper and a giver and a mutually beneficial networker, then when you have the ask, people are going to be a lot more willing and eager to help you because it feels authentic.

YW: These are great guidelines—I want to know more! But now, as time is getting short, I need to switch gears, and ask you if your Yale experience has had any bearing on your subsequent career focus—and if so, how.

LP: I had entered Yale wanting to be an English major. My dad is an English teacher, and I love to write, love to read. And it was a really prestigious major, too, which was really attractive to me. But it turns out I was really unhappy with the traditional nature of the English major. And then I took these American studies classes and I was like, 'This is great. I love this!' I like writing about stuff that feels current and relevant and culture and history and politics and all that kind of stuff. So, I finally switched to American Studies at the beginning of my junior year. That was a really huge move for me, to say 'I don't have to do the prestigious thing. I want to do the thing that I actually enjoy.' And, suddenly, my grades went up, my happiness went up. I enjoyed my classes. In retrospect, that was a really big moment for me. Another big moment: sometime after graduation, I had found a career coach who asked me to name the best job I ever had.  And I said, 'Being a freshman counselor at Yale my senior year.' And the thing I really loved was helping women with that specific college-to-early-career transition. That’s one of the reasons I wrote my first book, which kind of launched everything else I’m doing.

YW: A final question: you have a 10-year-old daughter. As you think about her making her way in the world, what are your hopes for her?

LP: My hope for her and her generation is that we really get away from this idea that you have to choose one thing. 'What do you want to be when you grow up?' is such pressure, right? Because right now, my daughter’s answer is, 'I want to be an actress and a lawyer and I want to run for president and I want to be a mom.' It’s like ten things. And I think we push people away from thinking like that. But the reality is, life is really long. So my hope for her is that she can be many things. That she can really explore all the things she's interested in and not feel that she has to be stifled.

— Laura Teller, ’77