The “Lucky” Ones – An interview with comedian and Daily Show producer Jena Friedman

Guys, I’ve got a great interview lined up for you today. I’ve been wanting to feature a comedian in this series for a little while, and I was psyched when today’s interviewee agreed. So let’s get started—meet Jena Friedman.

Jena Friedman (Photo by Eric Michael Pearson)

Jena Friedman is a stand-up comedian, actor, writer, and director based in New York. She is currently a field producer at The Daily Show with Jon Stewart and has written for Late Show with David Letterman. As the creator of the viral web series Ted & Gracie and American Girl Dolls parody “Refugee Girls,” Jena has a particular fondness for dark humor. (All the more reason this blogger loves her.)

Before she got her start in comedy, though, Jena studied anthropology at Northwestern University. It was there in Chicago where she inadvertently became interested in improv. Her work has been featured at SXSW, in New York MagazineSalon, Glamour, on Comedy Central, and more.


Ladies and gents, please welcome Jena!

When did you realize you were funny? And how did you decide you’d try to get paid to be funny?

Thanks for thinking I’m funny—I’m still on the fence. As for comedy writing, I decided I’d try to get paid writing comedy because I couldn’t do anything else. I had a few other jobs, like in consulting and copywriting, but my focus always pulled me back to comedy, so I guess when I realized I had no other options is when I knew I had to pursue comedy writing.

Describe your early improv and stand-up experiences. Did you ever have a really embarrassing moment on stage?

Yes, too many. One time I was telling a joke about AIDS (to clarify, in the joke, I wasn’t making fun of AIDS, just my fear of it) and this hipster started heckling me and telling me I shouldn’t make fun of AIDS, so I responded, “How do you know I don’t have it?” and that shut him up and got the whole crowd on my side cheering me on… but only because I made them think I have AIDS just to sell my joke—not my finest moment.

Who were some of your biggest influences (whether that’s family, friends, or other comedians)? 

My dad really influenced my comedy. He’s a doctor, so he’s pretty morbid and clinical, and when I was a child he would buy me really disturbing books (like this comic book called The Big Book of Death in which each chapter explored a different way of dying), and I would just devour them. I also remember seeing Sarah Silverman and Janeane Garofalo when I was younger and thinking I wanted to be like them.

Ted & Gracie

When you landed a job on Letterman, was that the turning point in your career? Tell me about how that felt to make it “big time.”

I was literally three weeks away from moving to L.A. when I got Letterman. It was a great feeling to get that job. I had applied a year earlier and didn’t really think they were still looking for a writer. So when I got the email asking for another submission, I sent it in the next morning and got the job a day later.

I remember meeting Dave on my first day and he said, “This is a shitty place to work, but I guess it looks good on the resume,” and I thought, “Wow, this is the big time.”

There must be incredible pressure to write for a show that airs five days a week. How did you do it?

You just try not to think too much to be honest and just write. Late Show is a machine that’s been running for 30 years, so all the parts are in place and it moves with or without you. So many great comics have gone through there and succeeded and failed, so I actually didn’t feel like if I didn’t make it past the three or six month mark I’d have anything to lose, which definitely helped my creative output.

You often hear how tough it is to be a woman in comedy. Do you think that’s true? Have you dealt with sexism in your business?

Yes, it’s tough. It’s tough for minority men and women as well, and really anyone who’s an outsider, particularly in writer’s rooms and in stand-up clubs. But the good news is that everything is changing, partly because people are more aware of inequality and partly because the internet has made it so voices outside the mainstream can be heard. Even in the seven years that I’ve been doing comedy, the landscape has diversified a lot… this is a long and unfunny conversation, but I’m optimistic.

I’ve dealt with sexism in comedy by wearing really shapeless cardigans—no one hits on a girl in a cardigan.

Jena Friedman

Which has played the biggest role in your success—luck or persistence?

Persistence, hands down… and not being unlucky.

What are some of your favorite books/films?

I’m a huge fan of Edward Gorey, Roald Dahl, Woody Allen, John Waters, Kathryn Bigelow, Margaret Atwood… if I start naming comedians I won’t stop but the show Summer Heights High by Australian comic Chris Lilley is possibly my all-time favorite, it’s a really long list… I just read Haruki Murakami’s The Wind-Up Bird Chronicle. It was like getting a long, intense hug from an imaginative Japanese man… also, I’m addicted to Breaking Bad.

Describe your role for the Daily Show. What do you love about it? And, I’ve gotta ask… what’s it like working for Jon Stewart?

The Daily Show is really great. The people are some of the most intelligent, talented people I’ve ever worked with and Jon is awesome. I really can’t say enough good things about it.

Any gigs or new projects in the foreseeable future?

I’m doing some shows in D.C. the second weekend of October. I’ll tweet about them when I know more. Otherwise, I’m performing stand-up around New York, about once a week. I tweet those shows as well. Twitter, eek.


Thanks a lot, Jena, for taking the time to chat with me. I’ll be stalking your Twitter for updates. If you enjoyed Jena’s interview, let her know in the comments!

The “Lucky” Ones – an interview with bestselling author and journalist Julian Guthrie

After a long hiatus, I’m excited to finally bring back The “Lucky” Ones series, which—incredibly—began around this time last year. In case you’re new to Witty Title Here, The “Lucky” Ones is an interview series featuring words from creative types who are lucky enough to be doing something they love. Though their backgrounds vary, the interviewees all share one thing in common—hard work. Which is why it actually has very little to do with luck. These interviews shed light on what makes people tick and reveal the story behind each unique individual.

Currently, I’m on the hunt for more interviewees to keep the series going. I’m looking for people with a specific niche, whether that niche is museum gallery curation or circus performance. If you or someone you know might be a good fit, shoot me an email! In the meantime, I’d like to introduce you to my latest interviewee, Julian Guthrie.

Julian Guthrie

Photo by Chris Hardy

 Julian Guthrie has had the kind of journalism career that most budding writers dream of. A journalist with the San Francisco Chronicle, she’s won several awards, including the Best of the West Award and the Society of Professional Journalists’ Public Service Award. Julian’s writing has even been nominated for the Pulitzer Prize on multiple occasions.

Julian’s more than 15-year career boasts stories published by the Huffington Post,, The Wall Street Journal and more. She’s the author of two books—most recently, The Billionaire and the Mechanic: How Larry Ellison and a Car Mechanic Teamed Up to Win Sailing’s Greatest Race, The America’s Cup. The national bestseller was published this summer and tells a story of devastating setbacks, lessons learned, and an unlikely partnership between two men. The book is available on IndieBound and Amazon, and you can follow Julian on Twitter.


Welcome, Julian!

Tell us a bit about your start in journalism. When and how did the bug get you?

I always loved reading, which drew me into writing. I loved journalism because you get to ask any question that comes to mind.

How did you not only gain access to but also earn the trust of an incredibly wealthy man who once refused to speak to the press all together? 

I had a great story to tell, and he saw that. It has lot of different elements to it, from business to sports. Larry loves sailing, and he spent a decade going after the America’s Cup. He lost twice before winning it, so there are a lot of mistakes made and lessons learned. It took a lot to convince Larry to talk with me, but in the end, he saw that this story was a great story, and that it would benefit from his input.

What about the relationship between these two men intrigued you to tell their story? What is it about anyone who motivates you to learn more about them? 

The title says it all: The Billionaire and the Mechanic. I loved the idea of their unlikely partnership, but I also really liked it that they end up having a great deal in common.

I’m interested in ordinary people who do extraordinary things. That’s Norbert [the mechanic]. And I’m interested in how a kid from the south side of Chicago grows up and finds a way to change the business world. That’s Larry [the billionaire].

Billionaire and the Mechanic

Aside from your most recent book’s subjects, which interviewees have been your favorite to profile/feature?

It’s always the one I did last. So in this case, it’s a profile on George Gascon, the district attorney of San Francisco, who has a remarkable story of fleeing Cuba to find a better life in America.

As a San Francisco writer, what edge do you have on getting a good story? How do you think it compares to being a writer in other major cities? 

I’m a journalist with the San Francisco Chronicle, so I’m up on who’s doing really interesting things. And San Francisco is an epicenter of innovation, so that helps.

Journalism is still very much in an awkward place. What is the best piece of advice you could give a fledgling journalist (ahem, me) about navigating the ever-changing territory where pageview journalism is so rampant?

I would say that it’s very important to diversify as a writer. Write fiction, nonfiction, magazine pieces, newspaper pieces, and—to a lesser extent—use Twitter and other social media.

To be a writer, you not only have to be an expert at your craft, but an expert on your topic as well. How do you manage that with deadlines putting on the pressure? And what are some of the coolest things you’ve learned about in your research?

I learn something very cool with every story, which is the beauty of being a journalist. I only operate on deadlines, and they do get easier to manage. Now I can only operate under deadlines.

What are some of the biggest challenges you face in your profession?

Keeping print journalism alive. So much content has gone to the web. I still think there’s great impact to be had in the tangible written word.

You’ve been on the receiving end of a lot of praise and accolades. What would be the ultimate milestone of success for you?

I have achieved success and accolades, which is fantastic. I love being a writer. Now, though, I’m most interested in just finding incredible stories to tell, stories that are original and have themes that transcend place and time.


Julian, thanks so much for your thoughtful responses. They’re inspiring, to say the least, as someone who’s forging her own path in the world of journalism. If you enjoyed Julian’s interview, let her know in the comments!

The “Lucky” Ones – An interview with world-traveling New York Times Bestselling author Chris Guillebeau

How do I write an introduction for my next interviewee that expresses my unabashed excitement while maintaining a sense of dignified professionalism? No really, I’m asking. Because Chris Guillebeau is kind of a big deal in the world of blogging and publishing, and I’m beyond psyched that he agreed to answer a few questions for me. Read on to learn more about the non-conformist with the fully stamped passport.

Chris Guillebeau

Anguilla. Angola. Djibouti and Nauru. Recognize these names? They’re just a few of the countries The Art of Non-Conformity blogger Chris Guillebeau has checked off his list. In fact, Chris has visited every country—all 193 United Nations member states—in the world. He recently reached the end of the world (Norway, in his case) just in time to celebrate his 35th birthday. You could say he’s well traveled.

Chris is also well accomplished, but he got off to a rocky start. A high school dropout, he learned how to drive by stealing cars and spent his first job as a dishwasher throwing away the pots that were too difficult to clean. His rebellion would eventually be used for good, however. Now, Chris is a New York Times Bestselling author of The $100 Startup, a book on entrepreneurship that shows how you can make a living doing what you love for a small investment (and it profiles 1,500 people who did exactly that with success). Chris is also the author of the book based on his blog as well as multiple manifestos, and his writing has appeared in Huffington PostBusinessWeek, and USA Today. Despite all the success and reaching his goal of visiting every country in the world, one gets the impression that Chris is just getting started.

And on that exciting note—welcome, Chris!

You’ve inspired and influenced a lot of people with your unconventional lifestyle. Who are some of the people that inspired and influenced you?

I was originally inspired by a surgeon in California who left home to volunteer his services in West Africa for more than twenty years. These days, I’m inspired by many of the people in the AONC community who are all pursuing big dreams and crazy projects of their own. I host a lot of meetups and events around the world, and always go away feeling motivated to improve my work in response to what other people are doing.

The concept behind The $100 Startup is that anyone with the desire, skills, and $100 can create freedom through entrepreneurship. But, if it’s that simple, why aren’t more people out there chasing their fantasies?

There are actually a lot of people out there doing it. Working on one’s own used to be very unusual, but now it’s slowly becoming mainstream—or if not totally mainstream, at least not that abnormal.

Chris Guillebeau

Visiting numerous countries, did you always manage to immerse yourself into the local culture, or were there times when you felt like a perpetual tourist?

It’s more of a third-culture thing. I couldn’t say with integrity that I “immerse myself into the local culture” wherever I go, but I’m also not a tourist. Instead it’s more of its own sense of identity, perhaps that of a modern nomad or wanderer.

Is your idea of home, then, different from others’? Is it difficult to establish roots, or is home wherever you are?

I have a home in Portland, Oregon, and I travel the world about half of the time. I feel at home in Portland and in any number of other cities. Whenever I’m home for a while without traveling, I miss the road. After I’ve been on the road for a while, I miss life in Portland. It’s not one or the other.

Which has played a bigger role in your success—luck or persistence? And what’s your response to people who tell you how “lucky” you are to travel the world?

Both. Perhaps you could say that luck favors the persistent.

As for being “lucky” to travel, that’s another story. There are plenty of people in the world who aren’t able to travel, but most of the people who would say something like that aren’t among them. I’m able to travel because I’ve made choices that support that lifestyle.

The $100 Startup

When you’re your own boss, downtime can be hard to come by. How can entrepreneurs and self-starters avoid burnout?

You don’t burn out by working too much, you burn out by doing things you don’t want to do. I always think it’s dangerous in the long-term to continue to push yourself when you’re unmotivated. But when you’re eager and excited to do something, why would you burn out?

You stress the importance of helping others. Why is that so essential to personal growth? Is it all about karma, or something more?

It’s generally a good idea to be a nice person, but it’s not just about karma. I like the concept of “selfish generosity,” where we ourselves benefit as we seek to engage and contribute. Most of us want to be part of something bigger than ourselves. We can find that fulfilment through helping others.

Chris Guillebeau

Now that you’ve accomplished your goal of visiting every country in the world, do you have other big goals or plans in the works you can hint at?

Yep! First, just because I’m done visiting every country doesn’t mean I’m finished with travel. I love being on the road and have no plans of stopping—I hope to continue writing and traveling for many years to come. Right now I’m working on a new book about the nature of quests, not only my own but those of other people who have chosen to orient their lives around a big journey or lifelong pursuit.

Besides your own, what are some of your favorite books?

I mostly read fiction. Murakami is my favorite author, so I’ll pick A Wild Sheep Chase by him, A Prayer for Owen Meany by John Irving, and Girlfriend in a Coma by Douglas Coupland.


Chris, thank you so, so much for taking the time out of your schedule (which is packed, no doubt) to chat with me. It was a pleasure getting to know more about you, and I can’t wait to see what you do next. Have questions, comments, or general exclamations of giddiness (I know I do!) for Chris? Leave them in the comments!

The “Lucky” Ones – An interview with Inspired Taste food bloggers Adam & Joanne

When a friend from work suggested these next interviewees, I immediately went to their site and spent the next twenty minutes drooling. Adam and Joanne Gallagher are the creators of Inspired Taste, a popular food and recipe blog, and they’re here to share the details about their success.

Adam and Joanne of Inspired Taste

If there’s anyone you’d want to invite you over for dinner, it’d be Adam and Joanne Gallagher. Chances are, the couple would start the evening off with some spicy maple bacon wrapped shrimp as an appetizer, serve up some lemon chicken with fresh chickpea salad and focaccia bread on the side, then finish up the meal with panna cotta in blueberry sauce for dessert. After a few cocktails, they’d even send you home with all their recipes (here’s the Sun Basket pricing for same meals, for those who are curious). Sharing their culinary secrets is kind of their thing.

As the chefs, photographers, and writers behind the food and recipe site Inspired Taste, these high school sweethearts share a dream job and are “lucky” enough to be able to do it full-time. (We all know “lucky” is code for “they bust their butts.”) Hours of prepping, trial and error, and of course taste testing go into each and every new recipe Adam and Joanne concoct, and Inspired Taste has their personal stamp all over it. What started as a hobby became so much more for this ambitious couple, and they’re only just getting started.

Welcome, Adam and Joanne!


You guys are high school sweethearts, which is utterly romantic. How did your shared love for the culinary arts grow and evolve together?

Oddly enough, we only started to get to know each other two weeks before our high school graduation. From there, we didn’t really connect over cooking until the last few years of college. We both had apartments with kitchens so we began cooking together. Since we both enjoyed it so much, it evolved from there.

What did you each do for work before going full-time with Inspired Taste? Did your work lack in creative fulfillment?

Ready? We worked at the same engineering firm! Joanne’s parents owned a small business and we both worked full-time spending our days working on proposals and contracts. While the engineers were super creative, our particular jobs were not. That’s why the moment we came home we got to cooking—both nights and weekends.

When and how did the realization sink in that you could take your blog full-time? What did that feel like?

Our blog grew slowly and our road to making enough money to cover our lifestyle was, at times, painfully slow. Now, though, we often wake up in the morning and feel the need to pinch each other—it’s kind of still sinking in.

What were your family and friends’ reactions when you explained to them your plans of becoming professional bloggers? Did you have a lot of support?

Everyone has been really supportive, even when they don’t exactly understand what it is we do on a daily basis (not that we blame them). I’m not even sure we can explain it that well.

Adam and Joanne of Inspired Taste

Do you ever feel pressure to maintain and build upon your success? How do you keep it in perspective?

Sure, but our blog has a built in reminder—comments from our readers. Our blog is all about food and cooking so when we get a comment telling us how well a recipe worked out for them and their family/friends it feels good. Like most people, we feel pressure all the time, but the comments keep us grounded.

Do you ever worry about running out of inspiration for new recipes or content?

Not at all—inspiration really is everywhere. Sometimes it takes a little longer, but we always get there in the end. If we’re feeling down, we pick ourselves up and either go somewhere like the beach or a park. Or, we’ll try tackling a crazy recipe—something like sourdough bread, homemade pasta or croissants. All just for fun.


Describe the joy that cooking (and writing about cooking) brings you.

Food makes us smile—fresh produce in the grocery store or markets, garlic hitting hot oil or tomato sauce simmering away on the stove. It hits all the senses, and since we both love it so much it gives us things to chat about and connect over. Plus, we get to eat it.

What are some of your favorite books (or cookbooks)?

Tough question—we’ve got so many! We absolutely love anything from Alice Waters, Julia Child and of course fellow food bloggers—so many have transformed their passion into amazing cookbooks.

Adam and Joanne of Inspired Taste

Some professional bloggers let their work consume their lives. How much time do you spend cooking, writing, editing, promoting, cleaning, etc.? Does it become tedious? How do you avoid burnout?

We try to keep some balance, but sometimes work takes over. We cook all the time, but try our best to keep things like writing, editing, responding to comments and promoting to the day and not evenings. As far as cleaning—we hate it, but probably spend as much time doing that as cooking. It’s worth it, though.

Yes, sometimes it is a little tedious, but the pros outweigh the cons.

Are there plans or dreams of Inspired Taste taking on forms in other mediums like, say, a book?

Sure—lots of them, but for now, we’re happy growing what we have. We love what we’re doing today.

What sacrifices have you made to make your dreams a reality and sustain them?

Lifestyle. Just like many small business owners, we have found that we need to give up a few things to keep the business growing. For example, we absolutely love to travel, but have held back a lot since working full time. We hope in the future we’ll be able to travel more. It’s worth the wait, though. We are completely in love with what we do on a daily basis.


Thanks so much, guys! I cannot wait to try out some of your recipes. Have questions or comments for Adam and Joanne? Leave them in the comments!

The “Lucky” Ones – An interview with The Innocents novelist Francesca Segal

A few months ago, I was lucky enough to receive a copy of my next interviewee’s book in the mail. Embarrassingly, it sat unread at the top of my book pile longer than I intended. When I finally picked it up, I was only sorry I hadn’t read it sooner. And now that I’ve had the pleasure of reading her book, I can finally introduce you to author Francesca Segal.

Francesca Segal

Photo by Nick Seaton

Growing up, London-born author Francesca Segal spent much of her time between the UK and America. First establishing herself as a journalist, she contributed to publications like Vogue, the Guardian, and Newsweek. Her debut novel, The Innocents, was released last year and received praise from the ObserverPublishers Weekly, and People magazine to name a few.

As is often the case with writers, Francesca’s love for words came at an early age. Crediting her father Erich Segal, author and screenwriter of the bestseller-turned-box-office-hit Love Story, Francesca recalls practicing mock interviews as young as age four. The bug has stayed with her since.

The Innocents is a stunning novel about commitment, betrayal, and family ties. With her exquisite prose and witty storytelling, Francesca elegantly captures the complex inner workings of a loving yet dysfunctional family. It’s a captivating story and, hopefully, the first of many for Francesca.

Welcome, Francesca!

Every published author, it seems, gets well-intentioned but maddening comments from others such as, “Oh, how fun! I wish I had time to write a book.” Does it drive you crazy? What do you say to those people?

It used to bother me far more before I was published, because I felt intimidated by all of them. But now I just understand it’s how people are. I’m married to a scientist and he gets exactly the same thing – when he talks about his work, everyone asks where he’s “studying”. No one can understand that being a scientist is a job, not an extended degree. And no one really thinks writing is either.

What these people don’t seem to realize is that this kind of undertaking is about shifting priorities and making sacrifices. What did you have to sacrifice to write your novel?

I turned down a lot of work; I turned down a lot of social engagements, and I lived like a hermit for a very long time – blissfully – but quite isolated. And of course you have to finish a first novel before you can sell it, so you’re doing a huge amount on trust. It’s hard to quantify, but it is an enormous undertaking.

Many people assume fiction writing is heavily inspired by the author’s life. Is that at all true for you?

It’s true that people assume that, but my novel is very much fiction and not remotely inspired by my own life, or my own family. The tapestry beneath the story – the community I’ve described, is one that I know very well, and that social climate is drawn from real life. But that’s it. No real people.

The Innocents

Does the current state of the publishing industry create pressure for you to be successful? Have you had a lot of support?

I’ve had wonderful support from my publishers everywhere, and so I have nothing to compare it to. But yes, I think now that everyone can see sales figures at a keystroke, there is less opportunity for a slow trajectory to success. Authors are expected to get further, faster.

How do you deal with negative reviews?

Lie face-down on the sofa in fit of abject misery and self-pity, rant about it to my husband, then pull my socks up and get on with it. I’ve been very lucky, in general, I think. But you can’t listen to every voice.

What was it like finally seeing your book on shelves? Did it live up to your expectations?

It was heartstopping. It’s all I’ve dreamed of for so long, it was almost impossible to process.

How much of the time spent on your novel was dedicated to revision? And are you ever truly done, or do you just have to make the decision to let things be as they are?

About half and half, I think. No, I believe the maxim that books are never finished, merely abandoned. At some point you feel you are doing more harm than good with your revisions, and then you stop.

Francesca Segal

Photo by Tom Craig

“Writer’s block” is a much debated-over topic. What’s your take on it?

I sometimes think labelling it akin to pathologising it. I would try and just call it a hard week/month at work, which we all have sometimes, and know that it will pass. “Writers’ block” sounds terminal.

Besides your own, of course, what are some of your favorite books?

I love Midnight’s Children by Salman Rushdie; Fugitive Pieces by Anne Michaels; I adore Jane Gardam, AS Byatt, Jennifer Egan, AM Homes, Naomi Alderman, Hilary Mantel – I could keep going, and those are just the contemporary novelists.

For you, what is the greatest reward for writing and exposing your work to others?

It’s wonderful to hear that a work has touched readers, and hearing their reactions is amazing after crafting something alone for so long. Everyone finds something different in your work, and it’s a privilege to talk about it. But being able to do the work is the greatest reward – that how this book has done means I can go away and write another book.

Do you have any advice for aspiring or struggling novelists?

It’s not very original but reading is the key to everything – you must be a passionate reader in order to write. Everything you need to know about beautiful prose, about crafting a character, about pacing a plot, can all be found in the Canon.


Thanks so much for sharing your insight, Francesca. I’m always fascinated  by the writer’s process. Were you equally as fascinated with Francesca’s interview? Let her know in the comments!

Do you think you or someone you know would be a good fit for The “Lucky” Ones series? I’m on the hunt! Check out past interviews, then shoot me an email at wittycassiehere [at] gmail [dot] com.