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Episode 1 - Lindsay Silberman

The Real Low Down On What It’s Like To Get Paid To Stay at 5 Star Hotels and Write About It

4 Key Learnings – Lindsay Silberman

How to land your first internship, then your first job, and lay out a path to your dream job.

The keys to building relationships with people that don’t have time for you.

When it’s time to move on to the next step in your career.

The story that made Lindsay call home crying, but now she calls a integral part of her career so far.

About this Episode

Lindsay’s career has taken her to some interesting places. Working for GQ, Inc., Playboy, and now Town and Country, she’s been fortunate to interview celebrities like Derek Jeter and John Legend, and write about her stays in luxurious hotels all over the world. But it isn’t alway fun and games (like flying 8 hours with food poisoning after some bad oysters in Ireland), and it sure as heck wasn’t always easy (think Devil Wears Prada). Hear how she did it, and her advice to others in this insightful and entertaining episode.

“While in college I did a summer internship working for Playboy. On my second day they made me interview drag queens on camera about having sex. It was the most uncomfortable thing I’ve ever done. But I learned to embrace the things that made me uncomfortable, and now I do it for the story.”

Lindsay Silberman

Listen to Episode 1 - Lindsay Silberman

The Real Low Down On What It’s Like To Get Paid To Stay at 5 Star Hotels and Write About It<br />

More on – Lindsay

Vogue.com, The Wall Street Journal, GQMaximPlayboyMen’s Fitness, Elite Traveler, Domino, DuJour and others. Ever since she began my career as a journalist, she’s practiced one mantra: DO IT FOR THE STORY. Beyond magazines, she often lends her expertise as a consultant to hotel brands, start-ups and technology companies. When she’s not at an airport or on a plane, Lindsay lives in New York City.

Connect with Lindsay

Products Mentioned

  • Lean In, by Sheryl Sandberg
  • Tumi Luggage
  • Arlo Sky Luggage
  • Bose Noise Cancelling Headphones

Max Altschuler:

Welcome to this episode of the Career Hacking podcast. Today&#39;s guest is Lindsay

Silberman, senior digital editor at Town &amp; Country magazine.
Before we get started, just wanted to say a special thanks to our sponsor,
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ZipRecruiter.com/hack, and it&#39;s the smartest way to hire, so go check them out.
On today&#39;s show, we have Lindsay Silberman with us, giving us the real lowdown
on what it&#39;s like to get paid to stay at 5- and 6-star hotels, and write all about it.
And Lindsay&#39;s had quite a journey, but actually, I&#39;ve known Lindsay probably
now since we were both in high school. Gotta give credit to Jewish geography,
when you grow up in the Northeast. But I&#39;ve been able to passively follow her
through her journey, through her jobs at Playboy, GQ, Inc, and now Town &amp;
Country, and she&#39;s gotta interview celebs like Derek Jeter, John Legend, Chrissy
Teigen, Kid Cudi, and many more. So now her job takes her to remote areas of
the world, traveling to 5- and 6-star hotels, as the senior digital editor of Town &amp;
Country magazine. Lindsay, welcome to the show.

Lindsay Silb:

Thanks so much for having me.

Max Altschuler:

So you have this, what I would consider a dream job. And you&#39;ve got I think
100,000 plus followers on Instagram. I&#39;ve one of them. And it looks like every
other week, you&#39;re at a 5- or 6-star hotel in St. Barts, or hanging out with owls in
Ireland, or palaces in Marrakech, Morocco. So what I really want to know is, why
don&#39;t you tell us a little bit about what your job is, and what do you actually do
day-to- day right now?

Lindsay Silb:

Despite what my Instagram looks like, I actually am not traveling 24/7. A lot of people find it hard to believe that I do, in fact, work in an office building, and I have a desk, and I actually in the office, for the most part, five days a week, except for when I&#39;m traveling, which is … I&#39;ll try to do one or two trips a month,and then usually one or two bigger trips throughout the year, to somewhere far like Asia or Australia or something like that.

But I think I do a good job of making it appear as though I’m living this fantastic, fabulous, jet set life, which I definitely am, but I do have a full time job and I&#39;m not just a full time nomad, digital travel influencer. So yeah, I think appearances can be misleading, but I also try to make it clear to people that I am hustling in a, not even a 9 to 5, it&#39;s more of a 10 to 8, or 10 to 9 job, just like everyone else. But what my job affords me the ability to do is travel a lot, and see a lot of amazing luxurious places, because I&#39;m an editor at Town &amp; Country magazine. Iwork on the digital team, and so our readers are passionate about travel, and a lot of what my job is to do, is to check out some amazing destinations that the readers might at some point be interested in going to, or introduce new places to the readers, and my followers on Instagram, and be the guinea pig, and testthings out, and introduce new destinations and ideas to people.

Max Altschuler:

Let’s say two or three times a month, you’re on the road. Are you writing while you’re on the road? Are you detailing all these trips? And when you’re not on the road, what does that office job consist of?

Lindsay Silb:

Yeah, so I … Some of the travel is personal, and then I just love travel and not every single place I go is for a story that I’m gonna be writing. Some of it is just for a personal trip that I’ve been wanting to take. But when I’m on … To be honest, when I’m traveling to a place, I’m usually either taking notes on my phone or [inaudible 00:04:42] taking a lot of pictures, and then I use that as a reference to write about later, because I find that you have to live it, and be in it when you’re there, as opposed to just writing and sitting at your laptop the whole time. It’s really hard to experience a place if you’re just working in your hotel room.


So that’s how I operate when I’m away. But when I’m in the office, as a digital editor, I am responsible for not just overseeing travel. I do a lot of beauty coverage, I help with our SEO strategy, I deal with our e-commerce and look at our revenue, [inaudible 00:05:25] revenue streams. I help with social strategy, so different ways that we’re using Facebook and Instagram and Twitter and Flipboard and Apple News and all these crazy platforms to try to increase our traffic. I’m working with freelance writers to assign stories that I don’t have time or the expertise to do myself. We do big features, like a big political and investigative stories, or big funny trend stories, like I recently edited a story about girls in the South who are in sororities that hire rush consultants to try to get into the sororities of their dreams.

Max Altschuler:


Lindsay Silb:

That was a fun one, and just yesterday we put up a big speculation about Hope Hicks and what she’s gonna do after the White House, so it’s really runs the gamut. One day I could be writing about the best beauty products for anti-aging, and then the next day could be editing a story about John F. Kennedy’s life before he was in the spotlight. So it really … I love my job, because of that reason. Every day is something different, and every day I’m learning about a new subject, and it never gets boring.

Max Altschuler:

All right. I think you’re in a pretty enviable position, at a pretty young age. And so, can you trace back to how you started, and really connect the dots on how you got to this senior director or senior editor position, sorry, so quickly? How did you get your start?

Lindsay Silb:

So, it’s funny. I was thinking about this last night, and there are times when I feel unworthy of being in this role, and having this amazing job. But then when I really think about it, I hustled and busted my ass to get here, so in a way, I do feel deserving of it. All throughout college, I knew my dream job was to work at a magazine, so I went to school, I studied journalism at the top journalism school, at Syracuse, the Newhouse School of Communication.

And then all throughout college, every summer I did at least one internship, if not two. One summer I interned at Vogue magazine and Lucky magazine, on alternating days. I interned at Playboy magazine, I interned … I basically spent every waking moment of my summers during college in a fashion closet or sitting, running, getting coffee for people and doing errands, and doing crazy intern things, so that when I graduated, I started at first as an intern at GQ magazine, which is always a place that I had dreamed of working. And then eventually they brought me on as a freelancer. Then after that I became a business reporter at Inc. magazine, which really was a job that I was not interested in taking, but it was a good job and a good opportunity, and it was during the economic crisis, and there wasn’t a lot of options. So it was, I had to take it if I wanted to keep living in the city, so I did.

And I’m [crosstalk 00:08:35]-

Max Altschuler:

Priorities. Yeah

Lindsay Silb:

Yeah. I’m the type of person, I love celebrities and pop culture and beauty and travel, and so to put me working as a business reporter, surrounded by people who graduated with MBAs from Ivy League, were business experts, I was a fish out of water. But that experience, honestly I think it was probably the most eye-opening experience I’ve had in my career journey, because I think it proved to me that if you’re able to survive in an environment where you feel totally vulnerable and inexperienced, then being in an environment where you feel like you can thrive, which is for me pop culture, travel, beauty, things like that, it’s a breeze.

So I worked at Inc. I had a bunch of other jobs. I worked at TVGuide.com, which got me into the celebrity entertainment circle. Then I helped launch a magazine called Du Jour in 2012, which is all about luxury lifestyle, and that’s how I got into what I’m doing now, which is pretty much all luxury lifestyle. And I spent four years at Du Jour, went freelance for a year, then Town & Country approached me about coming on to join their team, and I was really excited about it, because I knew it would be all the things, that I would be doing all the things that I love.

Max Altschuler:

So what I’m hearing is, you worked really hard, you took every internship you could get your hands on, you spent a lot of time living and breathing what you wanted to be writing about. Obviously worked really hard, but also got outside of your comfort zone. So some of those jobs that you had on the way up, were not really in your wheelhouse. But you took them, and you knew that you could kick ass at something that you weren’t that interested in, or wasn’t in your comfort zone, so it gave you a lot more confidence, and helped you later on, knowing that even if you are, for your age, in a position that is pretty senior, you have this confidence that you can tackle it, because you’ve been there, done that.

Did you have your own blog, or anything, that you were keeping your own notes on, or do you [crosstalk 00:10:44]-

Lindsay Silb:

I actually, when I was in college and I was studying abroad, I had a blog. It was before people even really had … It was, I guess I would call it a blog, but it was really just a way to keep in touch with my parents, because I didn’t have a Blackberry or a cell phone, and so I would just post every day what we were doing, and where we were traveling to, and pictures. And my parents would check it, and that’s how they knew that I was alive.

And it’s funny. I stopped doing it after I came back to the city, because there wasn’t really a need to do it anymore. But I really kick myself, because all I can think about is, had I kept at it, and that would have been so many years of building my own brand, and yeah. I just look at a lot of the most successful bloggers now, who started their blogs at that time, and I … Yeah. I totally wish it’s something that I had stuck with.

Max Altschuler:

Yeah, and the tools that are available to you now, versus 2007, 2008, are much different. If you had Instagram back then-

Lindsay Silb:

Oh, completely.

Max Altschuler:

What’s your top two or three recommendations for people who are maybe where you were early in your career, or maybe they’re in some kind of corporate gig right now, and they want to make the crossover into what you’re doing, and living the lifestyle you’re living? What do you recommend? Is it starting a blog? Is it just going in and doing an internship, going [crosstalk 00:12:13] somebody part time?

Lindsay Silb:

I think that this industry is extremely hard to penetrate if you don’t have experience, and it’s hard to get experience without experience. So it’s a catch-22, but you have to have experience working in some form of digital media in order to get a job or at least even an internship. So I think being in this type of business is what you want, you really need to know in college, and you need to start interning early, because it’s tricky. If you’re five years out of school and you’ve been working in a different industry and then all of a sudden you decide you want to work at a magazine, it’s like, best of luck. Other people have spent 10 years putting their time in.

But another thing that I will say, and what is one of the most valuable lessons that I’ve learned in the process of getting to where I am now is that, you’re probably never gonna get your dream job right out of the gate. I was, right out of college, all I wanted to do was be an editor at GQ. And I was so disappointed when they didn’t have an editor position, and I had to be an intern, and then they had a bunch of layoffs, and then they couldn’t hire me full time, and so I had to go look for another job, and I felt like I was settling for this other position at Inc. magazine that I really didn’t want. And I thought my whole plan had been thrown off, and all I wanted to do was work in entertainment and pop culture, and by spending two years and working for a business magazine, it just was ruining everything.

But what I really learned is, I was so wrong. And I talk about those two years that I spent working, covering a subject matter that was so foreign to me, and I became an expert in it. And I feel like that actually is what got me so many jobs, is because if you can prove that you can hustle for a place that is not your expertise, then the things that are your expertise should be no problem.

And I also just think that people have this idea that right after you graduate, you just want to be … People are so specific and so narrow-minded in the type of job that they’re applying for, but I think it’s really better to be open, because you never know. I never in a million years would I have thought I would have been applying to that job, and happy there, but I really was.

And the other thing is that, when I started working there, I put my time in, and eventually I started talking to my colleagues and saying that I loved celebrities and entertainment. And we did cover small business owners, so I was wondering if there was a way that maybe I could write about celebrity small business owners, because that made it more interesting to me, and it also was something that the magazine hadn’t really been doing. So this was when Bethenny Frankel from the Real Housewives was launching Skinny Girl margaritas, and a lot of other celebrities or reality TV stars were starting businesses. And so I really took an interest in that, and once I started covering that, then the job became so perfect for me.

So I also think you have to … I don’t know. Your job is what you make of it, and I think if you’re lucky enough to have bosses that are flexible and trust you, then sometimes you can pivot into doing something that wasn’t initially what you were hired for.

Max Altschuler:

Yeah. That makes a lot of sense. And so you look back early in your career, and the path that you took, are there any horror stories, or things maybe at the time you were like, “What am I doing here?” or were really down on, that you can look back on now and be like, “Wow, that taught me so much”?

Lindsay Silb:

How much time do you have? When I was an intern at Vogue right around the time when there was a documentary. I feel like it was right before The Devil Wears Prada came out, and I remember I saw The Devil Wears Prada and I thought, “Wow, they really didn’t even make it seem as bad as it was.” It was exactly how you would imagine it. I was running all over New York City, doing crazy tasks for … I had one editor who over the weekend had lost her ATM card at an ATM somewhere in the West Village, and she asked if I would go to the West Village and canvas every single ATM and bank, to try to find her ATM card, even though she didn’t know which ATM, which bank, or what location she had left it at. So I basically spent three days going into every single bank in the West Village until I did find the card.

I had to sit … I was a fashion intern, so I worked in the fashion closet. And my first day, I was so excited. I thought I would be working on photo shoots, or helping, I don’t know, write stories. And I think I spent my first week folding pantyhose, sitting on the floor with no chair, no desk, no computer. I was basically just hidden in the corner, folding socks and pantyhose.

Then the next summer, I worked at Playboy magazine, which seems like an odd type of job for a 21-year-old girl who’s in college. I was the only girl who worked there, and on my second day, they sent me to go cover this party. I had to, on camera, interview drag queens about their first experience having sex, and what it was like to lose their virginity. And I [inaudible 00:18:06] interview all these celebrities. It was the most uncomfortable experience of my entire life. I was new to the job, I was fresh out of junior year, and I had never written about sex or really talked about it, in the capacity that I had to be working there, because it was just so matter-of-fact. I had to go to the Museum of Sex, and do a big story there. I had to interview … They would do this thing called The Girls of the Big Ten, and it was this nude pictorial of these college girls, and I had to call and interview them about their bra size and what they look for in guys. And it was so embarrassing, because it was open format office, and I was on the phone asking these girls these probing questions, in front of my bosses. It was pretty much as mortifying as you can get.

But eventually, you get so used to it, and it becomes just so matter-of-fact, that two weeks in, I was like, “So, what’s your preferred sex position?” And it was not a problem.

Max Altschuler:

Yeah. That makes a lot of sense. And so you look back early in your career, and the path that you took, are there any horror stories, or things maybe at the time you were like, “What am I doing here?” or were really down on, that you can look back on now and be like, “Wow, that taught me so much”?

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