Forever Employable Stories: Lindsey Pollak, NYT best-selling author and multi-generational work expert

Posted on November 16, 2020.

Just ask for what you want. It sounds simple and straightforward and yet so few of us actually do it. It’s something I’ve had to practice doing, shushing the voice in my head, “you’re just going to bother that already-busy person, leave them alone.” Well, it turns out just asking pays off. That’s how I met Lindsey Pollak. After coming across her profile on LinkedIn, I just asked to speak with her. We met and it turns out we had a ton in common (not the least of which is that her father and I went to the same high school, not at the same time obviously).

Lindsey is a writer, author, speaker and trainer on all things related to hiring diverse multi-generational work places, maintaining sustainable careers from graduation through retirement and teaching both job seekers and as well as employers how to nurture the kind of cultures that develop the kind of diversity modern businesses need to succeed. I was lucky enough to spend 30 minutes speaking with Lindsey as she’s getting ready to launch her 4th book, Recalculating: Navigate Your Career Through the Changing World of Work, which is a how-to guide for a post-COVID workplace.

In our chat Lindsey covers how she got started writing and why it worked for her as a way to exit the mainstream career track and build her own brand and business. She shares the struggles and ups and downs of becoming a writer — even with some pretty good connections — and how being present in the conversation and, equally as important, staying relevant to the current conversation keeps her forever employable. One of the tips she shares that I love is how, in a crowded space, looking for the work that no one else wants to do and then doing it exceptionally well can become the difference between success and obscurity. This is a theme Tara Schuster shared in her forever employable story earlier this year as well.

Watch our discussion here (the transcript follows below):


JEFF:    Welcome back. We’re going to do another fantastic Forever Employable Story. This time, my guess is author of four books and multigenerational work expert, Lindsey Pollak. I’m super excited to speak with her today. Thanks so much for coming and telling us your Forever Employable Story. You’re from the New York metro area. I’m from the New York metro area as well. We found out a really interesting fact that we have in common which is that your dad went to the same high school that I did. Obviously, not at the same time.

LINDSEY:         He’s a little older.

JEFF:    A little bit which is good. Small world which is pretty cool. Tell folks about yourself.

LINDSEY:         First, I wanted to say how you and I connected because I think it’s such an example of everything that both of us preach and practice which is that I’d heard of your book because the title is amazing. Then you reached out to me on LinkedIn and it was this serendipitous moment of, “Oh, I’ve heard of you,” and then you reached out. We didn’t know each other but you sent a nice email. I looked up your stuff and now here we are. I think it’s such a great example of you never know if you reach out to somebody where it can lead.

To tell my TLDR story, I did not mean to do any of this. There was no plan in place. My dad was a Fair Lawn High graduate. He was an English teacher. I loved reading books and writing. I went to Yale undergrad which I was really proud to do. I had absolutely no idea what I was going to do with it. I was really good at being a student. Normally when that’s what you are, everybody immediately says, “Well, you should go to law school.” That’s what people do, including my dad. That was kind of the loose plan and then I ended up getting a scholarship to go to Australia on a Rotary ambassadorial scholarship for grad school. One of the requirements of this scholarship was that you had to give speeches at local rotary clubs. I had to talk about, “Hey, thank you so much for sponsoring my master’s degree.” My mom had her own business when I was a kid. I ended up getting a master’s degree in women’s studies. I studied women’s entrepreneurship because I figured that’s interesting, kind of unique, and I knew that Rotary was very supportive of women in business. I had this funny combination of doing this degree, studying and interviewing women who had their own businesses, and then giving speeches about it. I didn’t think too much of it but I didn’t really know what I was going to do with it. I absolutely loved the speaking. When I came back to the U.S. 2 ½ years later in 1999, I had to report back to the Rotary Scholarship Committee. They said, “Miss Pollak, did you do your required speeches to local rotary clubs?” I said, “Well, I don’t know. How many were required?” They said, “Four.” I said, “I did 39.” That was sort of an aha moment. Then it was right at the time of the burgeoning internet. You write about this in your book so well. You like had to do it. You just had to work in the internet in those days.

JEFF:    The new gold rush.

LINDSEY:         It was the gold rush. I went to San Francisco. Funny story. I was at a sushi restaurant with a friend talking about how I needed a job and someone at the next table said, “I work for .com. We’re hiring. Do you want to come in an interview?” That’s how easy it was in San Francisco to get a job in the internet. I wanted to be in New York. I’m an east coaster. I ended up finding this perfect synergy at a magazine called Working Woman which had just launched a website. It was like my entrepreneurial women’s stuff, the web. It was my dream job. I kid you not, I’d still be there if it still existed. I loved the mission. I loved the job. I loved being in the internet. I was director of business development which meant nothing. It was sort of do whatever needs to be done. I rode that out for about 1 ½ years until the company went bankrupt. I was devastated. It was the .com bust. It was right before 9/11. I was laid off. I had some severance money. The CEO of the company, a man named Jay McDonald, gave me my Sony VAIO purple laptop and he said, “Lindsey, I think you should start your own business.” And of course, like all good advice, I totally ignored it. I was like, “Yeah, whatever. Thanks for the laptop.” I had no choice because it was 9/11. There were no jobs in New York. It was so terrifying. I started freelance writing because at the time, you could still make some money freelance writing.  I’d get little gigs writing a newsletter for somebody, editing something. I just kind of pieced together enough to pay my rent. I fully admit I was privileged enough that my parents helped me out. I just kind of cobbled this thing together while I was job hunting. I just kind of never found a job and I just kind of kept freelancing. The x-factor was this Rotary connection. They kept asking me to come and speak and talk about what I was doing. I was good at it. They’d say, “We heard you’re good. Can you come speak here?” I was paid $250 to speak at a Chamber of Commerce in Trumbull, Connecticut. That was my first paid speech. I didn’t know that was a thing. There was the writing and the speaking. Eventually, I needed health insurance and all that stuff. I got a part-time job at Working Mother magazine which had been a partner of Working Woman. I was sort of knowledgeable enough at the time and I don’t know why I did this but I said, “Can I work part-time?” I was really enjoying the freelance stuff on the side. They miraculously said yes. I worked three days a week there. I got my health insurance. I had my paycheck. Then I was building my business.

Miraculously, they let me work part-time. I was writing and speaking on the side. I didn’t have an idea of where it was going to go but I knew career stuff and women stuff. The defining moment was I started working on a book and I had no idea where it was going to go but I started writing about how I didn’t know what I wanted to do. The nepotism piece is that my aunt is a literary agent and I got a book deal. I wrote a book called Getting From College to Career. I also sort of stumbled upon the college speaking market which is career services centers in colleges. We’re always looking for people to come in and give talks. I really enjoyed the speaking and slowly but surely, I built this reputation just in the New York area, local community colleges, speaking about how to get a job in the new digital economy. You mentioned I’m a multigenerational work expert. That was now part of it. It was just kind of helping people get jobs and when the book came out in 2007, I sort of landed a little bit on the map but entirely in the campus market. I had started my business in 2002 and in 2007, I got the book deal. I was still freelancing and writing and working part-time for health insurance. What really changed everything was in 2008 when Barack Obama started running for president, the word millennial sort of exploded onto the scene and I changed my branding from college to career expert to millennial career expert. I kid you not, overnight, the phone started ringing. That word became so hot and I was really well positioned in the campus market. In 2008, PricewaterhouseCoopers called me out of the blue and said, “We hear that you teach college students how to get jobs. Could you teach us how to hire college students?” That sort of raised me into the corporate sector. That led to a 6-year role with LinkedIn as their campus ambassador and to my corporate speaking career. It was a fluke, the word millennial. I rode that fluke for about 10 years, wrote two more books, and around 2018 – I’m a Gen X’er. I’m 46 years old. A lot of people always said to me, “What about everybody else? You talk about college to career. You talk about millennials but millennials are getting older. You’re not such a spring chicken anymore. What about everybody else?” I really saw the writing on the wall and again, I switched my website and branding to multigenerational career expert. I wrote that third book The Remix: How to Lead and Succeed in the Multigenerational Workplace and really pivoted. So, I think part of my story of Forever Employable is sort of following my interests and my skillset but really watching what was going on in the market which was that this millennial idea was sort of on the decline as Gen Z was coming up and so forth. What’s happened recently with the pandemic is not a lot of companies were focusing on multigenerational teams when there was a pandemic going on. I sort of pulled out the stuff I had on remote work and the stuff I had on dealing with mental health in the workplace. Now I’ve written my fourth book Recalculating which is about how do you manage your career through these difficult times? I think the core has always been career development, personal development, success, leadership, but I’ve been able to pivot to watch what’s going on in the market and take that really big idea of career and mold it to what I see happening. I never planned it in advance but looking back, I think that’s what really makes the story come together.

JEFF:    That’s really fascinating. It’s worth pointing out that this sort of continuous reinvention that you’ve maintained throughout your career by paying attention to what’s happening in the world. I think a lot of folks miss that and it’s one of the things that I talk about a lot with folks these days is they’ll say, “I do this thing and if this thing that I do is no longer relevant, I’m screwed. I’m out of a job.” Okay, well that’s your job title and job description, but realistically, what’s the underlying thing and how could you reinvent it for the current context? In your case, it’s the generational, the generations you were dealing with and multi-generations. Right now, it’s pandemic related. I think folks underestimate this. Sometimes – and I’m not trying to take away any credit from your success here at all – it’s as simple as a rebrand or a repositioning. Maybe the material is roughly the same but you’re repositioning it for the current context with different words and now all of a sudden, triggers the kind of inbound leads you’re looking for.

LINDSEY:         I even remember changing from Gen Y was sort of the expected terminology for a while and then quickly millennial overtook it. I had to change stuff. You have to really pay attention to those things. I see it in the diversity, equity, inclusion space. There’s a lot of change to the language there and you have to keep up with those things to show that you’re really knowledgeable about your field.

JEFF:    The change we’re seeing today is super-fast. It’s one of the things that keeps folks relevant. It’s easy to be comfortable and say you’re going to ride it out as long as it goes. I get that. I get the desire for the consistency and that safety. If a pandemic strikes or there’s a layoff or a merger or an acquisition or the .com bubble bursts or whatever it is, how are you going to position yourself? Some folks will say, “That’s great. You tell these Forever Employable stories but these people are really comfortable being in the spotlight. They’re comfortable speaking publicly.” For a lot of folks, it’s their worst nightmare. Did you naturally take to public speaking? Was it something you were comfortable doing from the beginning or did you get good at it after a while?

LINDSEY:         I get that all the time too. How do you do that? I have to be honest. I loved it from the beginning and I know that’s very uncommon. I think one of the pieces of my success is I like to do something most people hate to do. They don’t want to be up there. There’s a joke like at a funeral. People would rather  be in the casket than giving the eulogy. That’s how much people hate public speaking. It was the same with writing. I haven’t gone into all the nooks and crannies but one of the things I did as a freelance writer was I ghost wrote other people’s books because so many people hate writing and I really loved it. If you can position yourself to do the things that other people don’t like to do, that’s going to be an advantage. For example, if I was in a group of rotary students in Australia and there were 10 of us and they said, “We need a speaker,” I was the only one who raised my hand. I very quickly realized, “Oh, wait a minute. That’s a differentiator here.” It doesn’t necessarily have to be speaking. I don’t really do much one-on-one coaching. It’s just not a skill of mine. I do it sometimes but if that’s what you’re really good at, one-on-one, coaching other people, then triple down on that. If you’re really good at writing, triple down on that. I just happened to have the advantage that mine is a very public space but for example, I don’t think I’m that great on Twitter. If you’re fantastic on Twitter, triple down on that and spend a lot of time building that. It doesn’t have to be speaking but I do think you have to find an area where you naturally gravitate.

I was hearing you reflect back on my story of pivoting. I think it would be harder if I didn’t love this stuff. With the pandemic, as difficult and challenging, and tragic as it’s been, I am utterly fascinated by what’s happening in the workplace. I want to learn about it and teach it. I would suspect the same from you with technology. I didn’t find a lane and say, “Well, this seems like an opportunity. I’m going to learn a lot about it.” To me, you have to have some natural affinity for the topic in order to pivot and recalculate because otherwise, it’s going to feel like a slog. To me, the speaking and the learning about careers is something that I genuinely like to do. There are other parts of the business I don’t love and I’m happy to talk about those. I think in some ways, I’m lucky that I like the speaking part but you could be equally lucky with something else that helps you market and position yourself as an expect. It doesn’t have to be speaking.

JEFF:    It’s interesting you said to double down on the things that you love. In Forever Employable, it’s all about planting a flag to kind of decide what domain expertise I’m going to be associated with. What am I going to be known for? What’s my thing? Then you said to do the things that you love which is great. There’s an exercise that I promote called ikigai. It’s a Japanese concept of your reason for being and it’s four questions. The first question is what do you love? The second question is what are you good at? Because they’re not always the same thing. What does the world need and what can you get paid for? Starting with what you love is a great place to really think about how to build a platform for yourself, how to build a name for yourself.

Public speaking, you take to it naturally. Other folks don’t want to do. You fill in the void. Fantastic. Then you said, “I’m going to write a book.” There are people out there who have dreamed about writing a book. Why did you decide to write a book?

LINDSEY:         I loved your story in your book about your first proposal didn’t sell. I wrote multiple proposals that didn’t sell and I did it not just for my first book but for my second and third book. I don’t want to make it sound like I just sat down and the muse showed up and I wrote a book. I want to go back to that doing what you love. I absolutely did not know this was it. I get so many people saying, “I love that idea but I don’t know what I love.” I tried a lot of stuff. I thought I was going to be a resume writer. I thought I’d like the career coaching. I haven’t gone back to the fact that I got a Master’s in women’s studies and that’s what I did my thesis on. I thought I was going to be an expert in the women’s space. I found that was limiting for me and wasn’t where I wanted to be. I didn’t feel a need to just stay in the women’s space. For some people, that’s their passion. I didn’t know this was going to be it. I tried a lot of different stuff. I think it was Gary Vaynerchuk who said, “If you don’t know what your passion is, just try stuff.” I so subscribe to that because this took many, many, many years to kind of hone in on this multigenerational work stuff but I tried other things. With the book, it goes back to what did you like to do? I think the first thing I said was, “My dad was an English teacher. I liked reading and writing.” I really enjoy books. I love books. I never dreamed of being a rock star. Like you, I dreamed of writing books. That was a little bit inborn. I think I have an essay I wrote when I was 8 years old that I wanted to be an author. I think that was natural. I will say one of the things I learned through my freelancing was a lot of people don’t like to write longform and I happen to like that. To me, it’s easier to write 10,000 words than write a Tweet. That just happens to be something that I enjoy that a lot of people don’t and I realized there was a market for that. The book was kind of like people dreaming of being a rock star or a celebrity or what have you. That was definitely in there. It’s something I still enjoy doing today. I’d like to write books forever. Some people do it and they’re done. To me, that’s just something I enjoy doing.

JEFF:    Despite the connections that you had and your passion for this, and clearly this was something that you were going to do regardless, it took five years to get your first book deal.

LINDSEY:         Even with that connection, I still had multiple proposals rejected. I don’t want to make it sound like this was an easy path at all.

JEFF:    This lifestyle or this approach to managing your employability and the kind of opportunities that you generate, this takes time. It takes time to find the place where your ideas truly resonate and then to build credibility within that space and then to really start to achieve things like getting a book deal. It takes time. Five years is how long it took me to publish my first book. It’s normal for a lot of folks.

LINDSEY:         I think it’s normal and I will say I started in 2002. It’s a whole lot more normal now. I felt like a freak back then. All my friends had full-time jobs. There was no WeWork. There were no Y combinators. It was just not a thing or it was just starting to be a thing because the internet makes it so much easier to do all this. People didn’t understand. I remember my 15th college reunion, a friend came up and said, “Now I kind of get what you did because everybody thought you were crazy.” It is a lot easier now and there’s so much more support and there’s so many more resources and apps and so on. It was very hard at the time to kind of go it alone. One of the things I’ve really learned from the 9 months or so of the pandemic, when this hit and the rug was pulled out from so many people, I was scared and I lost a lot of business but I felt grateful to be my own boss and have my own thing because I knew I could hustle and I wasn’t at the mercy of an employer to decide whether I was going to keep my job or not. It was not easy. It was incredibly hard but I knew I’d hustle. I think that anyone who wants to do this, and I think you say this really well in the book, it’s not easy. It doesn’t just come to you but if you’re willing to put in the work and hustle, there are endless opportunities. I think in some ways, you’re “safer” than if you’re just looking for a job. I know that’s probably an unpopular, controversial thing to say but I think that’s the world we live in now and I think we just learned a really hard lesson in that.

JEFF:    Having done this for a while, I know this business is cyclical. There’s months of feasts and months of famine. Generally speaking, in a normal year, November/December timeframe is very quiet and this is that part of the year I always feel like no one is very going to hire me again. This is it. The gigs have dried up. When that strikes, the panic really starts to amp up. The panic drives the hustle. You start to generate more content, more outreach, more whatever it is. You tried a bunch of different stuff. We’re the same age. I don’t know that I’d feel comfortable writing about millennials. How did you build relevance and credibility and the confidence to come out as, “I’m an expert on millennials?”

LINDSEY:         That word expert is so fraught. A lot of people are very uncomfortable with it. To be honest, I use it often for SEO because people will Google and expert on a topic and that’s what they want to see. I don’t often use as much to describe myself. Where it really comes from is I was an RA in college my senior year. I was a dorm resident advisor. We call them freshman counselors. I absolutely loved that big sister approach. When I started writing Getting From College to Career, my approach was a big sister – I do have a younger sister, Laura and a younger brother, Rob – sort of telling them just as I had told my freshman when I was a senior. “Here’s what I’ve learned. I didn’t see it as generational as much as, “Let me help the next group coming along.” I think to approach it from “millennials” feels a little bit more of what a marketer would do. To me, it was always just the next cohort coming up. How do I help them learn the lessons that I learned? I always took that RA approach. I’ve never done marketing to millennial stuff. It’s always been in the workplace context. To me, what I like to think about is my perspective is I’m always going to tell you what I wish I had known when I was in your shoes. I’m not going to say I know exactly what you’re going through but I have been there. Now with Gen Z and so forth, I sort of feel a little removed from it but I know that feeling. It’s funny you mentioned my dad. He’s a high school teacher. I think he still really relates to high school and gets that world just as someone can be a pediatrician and understand babies when they’re a doctor. I just really have an affinity for that time of life, of figuring yourself out in your 20s. It was so foundational for my life going through that. I just relate to it. Whether I’m going to be in my walker in my 90s going to campus saying, “I get it,” I’m sure is to be determined. I hate to say I read the market and became an expert on millennials. I had a deep, true affinity for that time of life and that drove my interest in learning more about it and helping them. It’s not just passion and love for it and seeing an opening in the market, it’s also I very much relate to that situation and deeply want to help people in that situation. I didn’t just identify a market and go for it.

JEFF:    That speaks to the ikigai concept. This is something you truly believe in and the world needs it on a continuous basis. We’re not going to run out of 20 year old’s. I love the visual you gave me that adults can be pediatricians. It’s like it’d be cool if there was a baby pediatrician.

LINDSEY:         Cool. I’m all for it. Doogie Howser.

JEFF:    We hinted about this at the beginning of the conversation. I want to come back to it because I think it’s really powerful. I think it’s something that most folks don’t do. I think that culturally as Americans, we probably do it more so than other cultures. I have a ton of friends in Europe, a ton of friends in the UK. It’s this idea that of asking for what we want like, “Hey, I’d like to interview you for a Forever Employable story.” You never know what people are going to say. How has that worked out for you? There’s a quote from you that I found that said, “I remember being in that position and thinking I’m going to annoy them.” Certainly I feel that too when I cold call people. People aren’t getting these requests as much as you think they are. That’s a quote from you. Talk to me about that as a strategy for building yourself up and getting the connections, the conversations, the business, the clients, whatever it is you’re looking for.

LINDSEY:         The self-promotion piece of this is hard. I think that’s where a lot of people fall down because they’re too afraid of it. I have fallen into that too. It takes a lot of hustle. It takes a lot of self-promotion and a lot of confidence. A lot of people aren’t comfortable with that. I deeply understand that. I had a couple of formative experiences. One was the positivity of those Rotarians early on that they really wanted me to succeed. I remember somebody said, “When you’re up there speaking, we want you to be good because there’s nothing more painful than watching a bad speaker. Just so you know, we’re cheering for you. We’re rooting for you.” That was a helpful experience. It’s these little moments in life. I really admired Kate White who was the editor of Cosmopolitan Magazine for many years. When I graduated college, I wrote her a letter and asked for her advice. A letter. She wrote back. Years later, we’ve connected and she’s been a mentor. She said, “You think I’m getting dozens of those. I wasn’t.” You think everybody is doing it and they’re not. It happens to me as a speaker. I’ll go to campus and all these kids will say, “Can I be in touch with you? Can you look at my resume? Can you review my LinkedIn profile?” I says, “Sure,” and one will reach out. Those are the odds. The Rotary Scholarship that changed my life, it was state by state. There were two scholarships per state. I was from Connecticut. Eleven people applied and two of us got it. Those are pretty good odds. Not always but when you look at some of the numbers, it’s really much more possible than you think. One of the things I always think about, Steve Dalton, who wrote the book The Two Hour Job Search. He’s terrific. He’s at Duke School of Business. He says you can ask a dozen people and if 11 say no, the one who says yes is going to be infinitely more helpful than the other 11 combined because when people do agree to help you, they’re usually so delighted to do so that it makes all the no’s not matter. I always try to keep that in mind that you’re just going to have to put out a lot of requests. It’s not easy but when you get the yes, it’s so extraordinary and so helpful it makes the no’s not matter.

JEFF:    The worst thing that could happen is they say no.

LINDSEY:         Especially now with LinkedIn and social media. I mean I had to write a letter and find a stamp and mail it or you had to pick up a phone which was terrifying. Sending an email, what do you have to lose?

JEFF:    Thank you so much for taking the time and telling us your story. It’s a lot to learn here; a lot of tips for helping folks figure out how to plant this flag, build their platform, and hopefully become forever employable.

LINDSEY:         Thank you. Thank you for the message. And just do it, everybody. You’ll never look back.

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