Interview with a Barefoot Writer: Valerie Young

“Chris Rock once said, ‘Being rich is not about having a lot of money. Being rich is about having lots of options.’ I think when you’re a writer and you work for yourself, you have a lot more options.”
— Valerie Young, Author, Speaker, and Expert on the Imposter Syndrome

If you’re wondering where to find the confidence needed to succeed at a writing career, meet Dr. Valerie Young. As author of the award-winning book, The Secret Thoughts of Successful Women: Why Capable People Suffer from the Impostor Syn­drome and How to Thrive in Spite of It, Valerie has unique insight into the hurdles that hold many creative professionals — and writers in particular — back from fulfilling their goals.

For over 20 years, Valerie has researched and writ­ten about the entrepreneurial mindset and the Imposter Syndrome in particular. As an interna­tionally-known speaker, award-winning author, and leading expert on the Imposter Syndrome, she’s changed countless lives by helping peo­ple scrap their fears and make a living off their passions.

Valerie’s work has been cited in multiple respect­ed publications including The Wall Street Journal, Kiplinger, The Oprah Magazine, Reader’s Digest, and Psychology Today. She’s been interviewed by countless national and local radio programs and has presented her teachings to tens of thousands of professionals at companies such as IBM, Intel, McDonalds, and Boeing.

Valerie has also spoken at over 60 major colleges and universities across the country and has been the keynote speaker for numerous conferences and association meetings.

If you’ve ever felt like an imposter in your career, or you worry whether you really have what it takes to succeed as a writer … you’re going to love what Valerie has to say.

The first book you wrote landed you a six-fig­ure deal. How did you do that?

What’s interesting about my story, is, most often people write a book first and then they start speaking on a topic. I did the opposite. I’ve been speak­ing on the Imposter Syndrome since the mid-80s, so, a long time.

How did that come about?

It was something I learned about in graduate school and I identified with. I started doing workshops on it, teaching on it. I had a self-pub­lished book (more like a manual).

Is that something you recommend other writ­ers try?

If somebody has an education or training back­ground — like I did — that’s a great way to start. Create workbooks with exercises.

People don’t think about that when they think about writing for a living. I was able to sell my manuals on my website, on my own, for many years. I gave a talk at Columbia University, and a reporter was there from the Chronicle of Higher Education, which is often read at universities.

How did that lead to your book offer?

There was so much buzz within the academic community about the Imposter Syndrome, I think that’s what caught the attention of several dif­ferent agents. One publisher finally called me directly.

I ended up working with one of the agents and she shopped it around in New York. She did it all day long, she did lunch and breakfast with pub­lishers and editors pitching books. She knew that all of these people in the publishing industry identified with the Imposter Syndrome. So, she went on these two day-long rounds of interviews with maybe six or seven major publishing houses in New York, and then there was an actual bid­ding war.

Between which houses?

This was between Random House and Little, Brown and Company. I ended up going with Ran­dom House, and with the editor behind Tim Fer­riss’ book, The 4-Hour Workweek.

What was that like?

It was really nice right out of the gate. But around the time I was due to turn in my first draft, she an­nounced she was leaving publishing. My second editor … it was not at all a good experience. But it was great to get a $127,000 book deal.

So you came into publishing through the back door because you proved your worth before you wrote the book — in contrast to what a lot of people say, which is to write a book to prove you know what you’re talking about.

If you’re going to talk to a publishing house, they want somebody who has a platform. The platform could be that you have 10,000 Twitter followers for this thing you’re passionate about. Your plat­form could be that you have spoken at X-number of association meetings, or you’ve been quoted in articles or in magazines.

A lot of our readers are experienced in their fields and are working on building up platforms.

Do they want to be seen as authorities? Like writ­ing, speaking is just another form of communica­tion. If that’s their strong point at the moment, then they should lead with the speaking.

I’ve been interviewed in major magazines, pub­lications all over the country, all over the world. I didn’t have a published book, but I’m still per­ceived as a “go-to” authority on this topic.

You achieved expert status by putting your­self out there. Was this what you always dreamed of doing with your life?

I was influenced by the generation I grew up in, which was: Grow up, get married, and have kids. Be a teacher as something to fall back on, in case something happened to your husband. But that never resonated with me. I initially wanted to be things like an artist, or a social worker, or maybe a makeup artist.


It was inconceivable that I would go to gradu­ate school. It was inconceivable to cut free of the working class.

But if I had it to do all over again, I would do the majority of the things that I have done.

You’ve spent years helping people from the creative fields make money doing what they love. Is there any single thing you’ve noticed, over the years, that all these budding entre­preneurs commonly need help with?

Yeah, you know what’s funny? The answer came to me when I was doing a radio interview, and it was right towards the end of the interview, the host asked me this question that no one ever asked me before. She said, “What’s the secret to your success?” Now, no one had asked me that before, which is probably good, because I would have over-thought it. So without thinking I said, “Well, I think it’s because I don’t spend a lot of time in the real world.” She kind of laughed. She probably thought I was on drugs or something. But what I meant was, in the “so-called” real world.

Can you elaborate?

When you tell people, “I’m going to quit my job and become a freelance writer.” Or, “I’m going to try and write a best-selling book, or I’m go­ing to be an artist.” Whatever it might be, people say, “Get real, you’re not being realistic.” Well, I don’t live in that world. I like to roam the world of possibilities.

There’s a quote from Will Smith, which is, “Being realistic is the most commonly traveled road to mediocrity.”

So true.

Why somebody else and not you? You have noth­ing to lose. You might as well go for it, because you never know until you try.

When you look back on all you’ve accom­plished as an entrepreneur, what’s been your proudest moment so far?

I created this program to teach people how to do the kind of brainstorming I do. One of my many profit centers is that I help people connect the dots between what they love to do and how they can make money doing it. I finally created a licensing program to teach other people to do what I was doing.

Writing comes in very handy, because I had to sit down and document what I thought was just kind of intuitive, and realized, no, I really do have a pro­cess. I do this instead of that, because that didn’t work when I tried it. Now I have a seven-step for­mula and I have manuals on how to work with clients, how to actually hire a copywriter, how to write enough copy about your area of expertise to put together a whole book, and so forth.

I realized that just because the people I was help­ing were good at what they were good at, it didn’t mean that they were good at promoting themselves … especially through writing on their websites.

The first time I launched my licensing program, it was an eight-day launch period. I sent out a lot of emails to get people excited about the program, then sold the program itself. At any rate, it was an $80,000 week.


So that was very exciting.

What was your most challenging moment as an entrepreneur?

Definitely when the economy crashed. I know there are a lot of people in the Internet world who publicly dismissed that, but privately, I know ev­eryone suffered. Colleges weren’t spending mon­ey on speakers anymore, everyone was spending less. I was spending less. Everybody was in “wait and see” mode.

That was the bad news; the good news was that I was an entrepreneur, so I didn’t have to worry about losing my job. I just had to get more creative about coming up with products that would inter­est people, and keep plugging along.

Let’s say you’re hosting a dinner party … which three writers, entrepreneurs, or cre­ative professionals would you invite?

This may surprise you because they’re in these different worlds, but one is Charlie Rose and an­other would be Amy Poehler. I just read her book and some stuff she said really resonated with me. And the other would be Chris Rock.

You would have a great time at that table.

Chris Rock has some great observations on life in general and then there’s a quote of his I put in my book, “Being rich is not about having a lot of money. Being rich is about having lots of op­tions.” I think when you’re a writer and you work for yourself, you have a lot more options.

So true. What’s the one book you wish some­body else would write for you?

I would love somebody to write a book on how to stop ruminating. Which is a challenge, espe­cially for women; the two sides of our brain com­municate with each other more than men’s do. So we are much more likely to lie awake, obses­sively going over a conversation. Both with good things and bad things. Going over the problem, the challenge, or especially if we are criticized, oh my God. If you are angry or upset and it’s hard to stop those thoughts. Men are much better at say­ing, “Forget about it.” “Don’t think about it.” “He’s a jerk, wake-up.” [Laughs]

In terms of organization, what are your favor­ite tools or habits?

My first response is “Ha!” I’m kind of organic in my organizational skills. I don’t like filing; I’m a hor­rible filer, so I have stuff piled up. But in terms of writing organization, especially when I wrote my book, I had this horrible incident where I was speaking in Texas, sitting at a table having break­fast, and my computer was in my bag on the oth­er chair. My client came in, picked it up, and I said, “I’ll take that.” She said, “Oh, no, no, no, I got it.” She set it on the edge of the fountain we were sitting at and it fell in.


After that, I always backed it up and at the end of each day, I would actually email myself an attach­ment of the book to another email account, and I became obsessive about saving things.

I don’t so much stay organized. I would just really cut and paste and put things into an extra folder, so I would have it for future reference or I could come back to it, or add it to a future book, or ar­ticles, or what have you. I wrote twice as much as I ended up actually using. It’s harder to be succinct I think.

Like the saying that’s been attributed to Mark Twain, “I didn’t have time to write a short let­ter, so I wrote a long one instead.” Out of all of the writing projects you have ever worked on, which has been your favorite?

I find writing hard. I do it, but “favorite” is kind of an interesting word. Writing my book was the hardest thing I ever did. Also the most satisfying. I think sometimes we’re afraid to let people know that writing can be hard. I think it’s important to know that, because otherwise people will get dis­couraged and stop. If we think it’s all supposed to flow and be easy, and then we hit a dry spell or we can’t think to save our lives, or we write 10 pages, we read it and it’s crap, then we get dis­couraged and, we think, “Oh, I must not be a writ­er.” It’s like anything, it’s all in the polishing and the improvement.

Even the greatest writers go through multiple drafts.

God, absolutely. All the editing, it’s all in the edit­ing. You can’t sit down and write your article or book in a single draft; that’s just not real life. It’s like expecting to walk out and do a movie, with no rehearsal, it’s crazy.

Why was your book the most satisfying thing you’ve done?

Because it got a strong re­view in Publishers Weekly, and then Steve Forbes asked for a signed copy for his daughter for Christ­mas a couple of years ago. Also, I sent Arianna Huffington a copy with a handwritten note, which is very helpful these days. I commented on some­thing I heard her say in an interview. She emailed me back and asked me to write for them.

Before you pursued your life passions, you said your life felt like a Dilbert cartoon. Many of our readers are in the same position. They’re looking for something different. What’s the first thing you recommend they do to pursue their dreams?

I’m a big fan of starting on the “life side” of the work-life equation. In other words, when we’re growing up, everybody wants to know what you want to be when you grow up. Nobody ever asks, “What do you want your life to look like?”

I think that’s partly why we end up in commuter traffic, in cubicles with fluorescent lights, and with micromanaging bosses. Nobody, when you were young would say, “Yeah, I would like some commuter traffic and fluorescent lights and a cubicle.” Nobody would say that, but that’s what they ended up with.

Because they pursued the job and not the life.

Exactly, pursued the job. They aren’t thinking what goes wrong with being an HR man, or an accountant or whatever, or a pharmacist.

My niece wanted to be a pharmacist; all I could think of was standing on your feet in a window­less room all day. Her starting salary after a gruel­ing five years of school was somewhere between $125,000 and $150,000. So it can be very good money and that’s fine, if that’s what your major driver is.

To me, if you start with the life side, you can come up with ways to generate income that will allow you to have as much of that life as possible. Not all of it, not all of it right away. The most important thing for me was to work from home or from any­where I wanted to work.

Why do you think that creative people are more prone to feeling like imposters?

It’s true they are a more susceptible group, and I think it’s for a few reasons: One, it depends on what you’re doing, but if you’re a writer, you of­ten work alone. Anytime you work alone, you are more susceptible unless you seek out the com­munity of others, which you should as a writer.

You work in isolation, so you’re not getting that feedback from your management and evalu­ations, that kind of thing. You judge yourself harshly. People in creative fields are judged by subjective standards, by people whose job title is Professional Critic.

Book reviews, film reviews, people can have very different opinions. You’re only as good as your last book, your last television show. You’re judged. I think you’re really judged by different standards.

I know many writers who can relate, myself included.

On the plus side, I actually think there are ele­ments of imposter feelings that are really healthy and are signs of emotional intelligence. I think most writers have a high level of emotional intel­ligence. They have to be introspective.

There are some people who are just so arrogant that they don’t even see their weaknesses, which I think is a bigger problem in many ways. We may focus too much on ours, but there are people who have “irrational self-confidence syndrome.”

I sure know a few!

There are two kinds of people: those who wel­come feedback, and those who think they can do it on their own. I really like getting feedback in terms of my writing. I don’t have a big ego about my writing. If you can tell me how to make it bet­ter, I might disagree depending upon what you say, but 80% of the time, I’m probably going to prefer your input and perspective. I’ll go with the feedback I’m getting.

If I were completely arrogant, I’d be like, “She’s a jerk, what does she know about good writing.” That was why I quit the first time. I would get very defensive or down.

You overcame your own midlife crisis when you chose a purposeful life over making a liv­ing and making money. What three steps can a new writer take towards a purposeful life?

First, you’ve got to start writing. Don’t spend all your time dreaming about your purposeful life. Just start writing. Second, get feedback. I had three different people reading drafts of my book as I went along. And third, edit. Edit like crazy.

But to get started with anything, you have to do that thing you say you’re going to do.

Take that first step.

Think about what you want your life to look like. Think about what kind of writing is more interest­ing to you that will keep you motivated during the inevitable ups and downs. Try to find your writing niche. Put yourself out there.

Because thinking about it is important; so is picturing it. But actually taking those actions, that’s what gets you there.

Right. The more you write, the more you increase your odds of luck finding you. Most people are “lucky” because they take action, they put them­selves in a position for luck to find them.

Like that quote, “Luck is preparation meeting opportunity.”

The harder you work, the luckier you get. So keep looking for opportunities. Which reminds me, another writing opportunity that people often don’t think about, is that there are professors at universities for whom English is a second lan­guage. They’re quite brilliant. Often they have to present papers at conferences and writing is not their strong point. Years ago, I read about some­body who did freelance work for a couple of dif­ferent professors, helping them edit their stuff and writing for them.

You’ve gotten testimonials from prominent figures and you’ve spoken in some of the most impressive institutions across the country. How do you measure your own success today?

I think you can kind of go back to the Chris Rock quote, about having options. A lot of what is satisfying to me about my success is feeling like the work that I do, in some way matters.

Having somebody email me, 10 years later and say some piece of advice works in the business they’re in, or this woman who was a college stu­dent — I can’t remember if she was at MIT or Harvard — she saw me speak and now she’s a manager at IBM, and she brought me in to speak because it had such an impact on her life. She got kind of teary when she talked about the Imposter Syndrome and how influential that talk was. Just feeling like in some small way, something you said or did, is making a difference. It’s very satisfy­ing to me.

If you could live anywhere in the world, espe­cially since you do have options, where would that be?

I can’t think of any place, because if I wanted to move somewhere I would. It might be fun to live in Paris a little while, but I don’t speak French, so that’s a little intimidating. I love my life, and I designed it with the life-first, work-second ap­proach. I have this gorgeous mountain view, and it’s snowing right now over the fields. I live in South Hadley, in Western Massachusetts, which is three hours from New York and two hours from Boston.

This interview was previously published in the February, 2015 issue of Barefoot Writer. To read more interviews from fellow Barefoot Writers be sure to checkout The Barefoot Writer's Club.

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Published: January 4, 2018

3 Responses to “Interview with a Barefoot Writer: Valerie Young”

  1. A wonderful article. Thank you! Friends and family can also unwittingly trigger an outbreak of the syndrome. When I shared with a friend, a businessman, one of my freelance goals, he replied, "You?? You. What makes you think you can do that?" When I told him that I was actually qualified, he shook his said and made a face. He knew me as a stay-at-home mom but not as a professional. But, of course, his opinion mattered to me and it took some time to shake it off.

    Kathleen Becker BleaseJanuary 5, 2018 at 4:56 pm

  2. It's been such enriching interview,full of brilliant ideas on the lmposter Syndrome that l personally feel need more people talking about it.Your advice on freelance writing is great and,especially by voicing the many concerns of would be great writers who shy away from writing out of ignorance. Thank you for your insights!!

    Guest (George Ngigi)January 9, 2018 at 6:04 am

  3. Thank you so much for this interview. Exactly what I needed to hear for that final nudge.

    Guest (Christine Madlock)January 10, 2018 at 9:36 am

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