Twenty-two rejections later, living in the same room I grew up in as a teenager, I was in a bona-fide dip. And, I decided this memoir-writing thing was not a dip I wanted to push through. If I wanted to continue to pay rent and buy groceries (and eventually move out of my parents’ place), I would need to be more flexible about how I interfaced my main set of skills (writing and editing nonfiction) with market realities. I hit “STOP” on the memoir writing. I began seeking out every gig I could get. Editing gigs. Ghostwriting gigs. Copywriting gigs. I helped people self-publish their books. I wrote book proposals for aspiring authors. Anything that had $$$ attached to it, and somehow involved words, I would do it.

A few years later, my money situation had improved a great deal. I was no longer going deeper and deeper into debt to cover my living expenses while I “went for my dreams” (as the motivational books put it), hoping some editor at a publishing house would bestow upon me a windfall advance. But once the money started to flow and I was on financially firm footing, I very quickly began asking myself: Is this how I want to spend the rest of my life?

I always knew that my great passion was writing books. Not editing other people’s books, not writing book proposals for other people’s books or marketing them. But writing my own. That’s what I was originally doing in my “starving memoirist” phase.

Well, with money handled, I now had the flexibility to write on the side, exploring this passion, yet without having to do it in a “starving artist” way. I wrote a proposal for what became my first published book, The Power of Eye Contact. Now, this was not “literature,” as I was attempting to write earlier, but neither was it pandering to some lowest-common-denominator market—it’s a substantive book. I received a $20,000 advance. That certainly wasn’t enough to quit my day job of freelancing, but it at least contributed to my income and allowed me to explore even more this passion on the side.

However, in 2010, I got the idea that I wanted my passion—book writing—to be my main income. I came up with the idea for my upcoming book, The Education of Millionaires, wrote the proposal for it, networked my way to a fantastic literary agent, and received a six-figure offer from Penguin. Now in 2011, I have come full circle: I have given up my day job completely, and have turned my attention entirely to book writing. Again, I’m not attempting to write artistic literature anymore, but I am making a living writing books which are substantive and meaningful.

That is enough for me.

So here’s the point. If you hit a dead end and need to take a step back to regroup, that doesn’t mean you need to abandon you entire dreams forever.

If I could give you one piece of advice it would be…

If your dream isn’t working, don’t be ashamed to abandon one part of your dream, then regroup, retool, try a different angle—and come back swinging.

You may find your real dream is actually much different—and much bigger—than you ever could have dreamed.

About

Michael Ellsberg is the author of The Education of Millionaires: It’s Not What You Think, and It’s Not Too Late, which is launching from Penguin/Portfolio in September. It’s a bootstrapper’s guide to investing in your own human capital at any age. Michael sends manifestos, recommendations, tips, and other exclusive content to his private email list, which you can join at www.ellsberg.com. Connect with him on Twitter @MichaelEllsberg and on Facebook.

However the transition from a compact business with little overhead, to one with ten
times the expenses, was not as easy as I expected, and in 2008 when the Global
Financial Crisis hit, I found myself in a depressingly deep dip.

My clients, considering the wellness services I provided to be a “luxury,” dropped away
like flies. Future funding promised by my investor evaporated, and I found myself facing
the imminent loss of everything I’d worked so hard to accomplish. It was dire times.
The “build it and they will come” approach clearly wasn’t working. My life had flip-
flopped from “dream” to “nightmare,” and I was hemorrhaging money that would soon
run out. I needed a new strategy, pronto.

Up until then, I’d had the attitude that “marketing” was something to be delegated or out-
sourced, similar to cleaning or plumbing. However from the depths of the dip I began to
realize that my presumptions about marketing were actually delusions. Largely thanks
to the influence of my now-husband, I realized that if I wanted my wellness center to
survive, I had to expand my identity and embrace being in the marketing business, in
my case, the “business of marketing wellness services.”

And so with everything on the line, I went for it. I became an avid student of direct-
response marketing, reading book after book. As soon as I learnt a principle, I’d put it
into action. I discovered I needed to get to know the needs, wants, fears, frustrations,
dreams and desires of my ideal clients. I needed to get into her head (firstly even
realizing this person was a “she” was a revelation.) I needed to understand the nuances
of her dilemma better than she even understood them herself, and then communicate
that back to her.

This became the focus of my time. Instead of managing my team–I’d sacked them all
by this point anyway!–my time was spent diving into the psychology of my prospective
clients and learning how to speak her language.

The skill of copywriting became my holy grail. I learned how to craft language that
communicated a tangible benefit to the reader, how to formulate an “irresistible offer,”
and how to make it compelling, thereby passing my ruthlessly-honest husband’s “snore
test.” Boring copy simply wasn’t going to fly.

I learned to be vulnerable, and speak openly about the ups and downs of my
journey with food, weight and emotional eating, and to be generous sharing my
knowledge for free. I learned that quality marketing is not sleazy or cheesy, but is
actually “compassionate communication”–something I could be proud to sign my name
to.

If I could give you one piece of advice it would be… 

Here’s my parting nugget of advice: No matter what business you’re in, to succeed you must be in the marketing business. If your chosen profession has been your true love, now embrace marketing as your mistress. Soon you’ll find yourself in a passionate menage-a-trois that delivers you all your fantasies and much, much more.

About

Jena la Flamme is a weight loss expert for women, the and founder of the Jena Wellness Center in NYC and the creator of Pleasurable Weight Loss™, as featured in Glamour and the Discovery Health Channel. For access to a free video training series on the “Secrets of Pleasurable Weight Loss” and other exclusive content, join Jena’s list and tribe at www.PleasurableWeightLoss.com. Connect with her on Twitter @JenalaFlamme and on Facebook.

Photo by lilie Mélo from france (week-end-pleasure) [CC-BY-2.0 (www.creativecommons.org/licenses/by/2.0)], via Wikimedia Commons

If this seems trivial, you need to know that for a period of my life it was crushing me.

I was a terrible singer, and I knew it. Not just because my choir teacher asked me to lip sync at concerts, though, that really didn’t help. No, I was like a lot of creative people who experience a talent gap. I knew what I liked, but I didn’t like what I was making.

The things I made were rudimentary, lacking, not good enough. When I sang, all I could think about was how bad I was. I let it get the best of me.

My nervousness would overwhelm me. My legs would shake, and my knees would jerk back and forth like I was running in place with my feet glued to the floor. My skin would shrink. My eyes would float above my head and it seemed like I was watching myself in slow motion, right before a crash.

I hated the feeling.

Ira Glass is the one who helped me realize this gap between taste and talent is pretty common. I wasn’t a failure. I wasn’t in this alone.

This was the way of things. Unfortunately, I didn’t see this video until years later. I also hadn’t learned the importance of selective quitting.

I was seventeen, and auditioning for theatre training programs. I wanted to sing in musicals. I really did. And, I wanted to be trained at the best program that would accept me. The kind of school with a rigorous audition process. The kind with ties to a professional theatre. The kind that cuts students from the program to keep it competitive. This is what I wanted, at least on one level.

On another, I wanted to follow the one thing in life I was passionate about to see where it would take me. My philosophy was that I only get one spin around this planet, so I’d better make the most of it.

The problem was my absolute inability to sing. There was no way a competitive program would take a singer like me. Still I tried.

One of my top ten, all-time, best failures was my rendition of The Way You Wear Your Hat at a college audition. Shortly after I ruined the song, the dean of the college asked why I wanted to be a musical theatre major.

I told them it was because I didn’t want to give up singing.

I answered the question I thought I heard: Why do you want to be a musical theatre major instead of an acting major? My monologues were good. I thought the question was why not just be an actor and forget musicals?

It wasn’t until three days later that I realized they were asking:

Why do you want to be a musical theatre major instead of an engineer?

Why do you want to do this crazy, insane thing instead of having a normal career? Why is it worth it to you to follow your passion? What do you have to offer this? What do you want from it in return? What fuel will get you through the hard times?

“I don’t want to give up singing” didn’t begin to do answer the question.

This next part still amazes me, because it required a leap. The very difficult, and now familiar, leap from having an idea to doing something about it. I called the school and asked them to connect me with the chair of the department. Luckily for me, she wanted to talk.

For the next hour and a half, we discussed the program, what I wanted, and what I really meant to say. It was one of the hardest, and one of the best, conversations of my life.

I had a spot in the program before we hung up. Not the spot I originally imagined, but a spot nonetheless. A way forward. I was just learning that my dreams aren’t the goals themselves. Dreams are solutions to problems. Roadmaps. My dreams are the way I see myself getting to my goals. Giving up on a dream that’s holding me back, quitting something that’s not working, is sometimes the best way forward. Not by giving up on the thing I want, but by inventing a new way to get there, by creating a new dream to follow.

It’s only looking back on this experience that I’ve learned I don’t have to close all the talent gaps in my life. Some dreams can be re-imagined. Loosing tactics can change. For the times when the best way forward is sticking to it, closing the talent gap, I’ve learned to embrace my allies, patience and persistence.

If I could give you one piece of advice it would be…

Get out of your own way. Let yourself change. Do whatever is necessary to move forward. This is what it means to find your voice.

About

Alex Miles Younger makes things beautiful. His business card will tell you he runs a graphic design studio, but what that really means is he solves problems for creative professionals by helping them execute their ideas and promote their art. Highlights include: launching The Domino Project (a publishing house founded by Seth Godin and powered by Amazon), and freelancing with Crispin, Porter + Bogusky on photo shoots for Burger King, Coke Zero, Geek Squad, Old Navy, Microsoft, Nike, and Volkswagon. Alex was born in a state known for bourbon, horse-racing, and bluegrass music. He believes we should all be more sincerely curious. You can say hi at alex@unozip.com or @unozip. 

Photo by Kfabrizi (Own work)[see page for license], via Wikimedia Commons

The One Thing I Wish You Knew

“Get lean and start thinking like a start-up”

About

Mitch Joel – President of Twist Image and author/blogger/podcaster of Six Pixels of Separation.

Marketing Magazine dubbed him the “Rock Star of Digital Marketing” and called him, “one of North America’s leading digital visionaries.” In 2006 he was named one of the most influential authorities on Blog Marketing in the world. In 2008, Mitch was named Canada’s Most Influential Male in Social Media, one of the top 100 online marketers in the world, and was awarded the highly prestigious Canada’s Top 40 Under 40. Most recently, Mitch was named one of iMedia’s 25 Internet Marketing Leaders and Innovators in the world. 

Joel is frequently called upon to be a subject matter expert for Huffington Post, BusinessWeek, Fast Company, Marketing Magazine, Profit, Strategy, Money, The Globe & Mail and many other media outlets. His newspaper business column, New Business – Six Pixels of Separation, runs bi-monthly in both The Montreal Gazette and Vancouver Sun. His first book, Six Pixels of Separation (published by Grand Central Publishing – Hachette Book Group), named after his successful Blog and Podcast is a business and marketing bestseller.

Photo by DoD photo by U.S. Air Force Staff Sgt. Manuel J. Martinez [Public domain], via Wikimedia Commons

It was depressing to hear something like that, but I quickly realized it was terrible advice.  While one executive at one network decided what we made didn’t fit with his fall schedule, the project was still very much alive on the Internet.  So I pressed on and kept creating new videos.  It was tough at first.  With the pilot I had large budgets and huge crews.  I was suddenly back to shooting with a few buddies and their consumer cameras.  I was back to having to produce every element on my own.

On top of that, the network had dumbly forbidden me from posting new content to my site while we were in development with them.  Improv Everywhere had lost a bit of momentum due to our lack of new material, and I felt all kinds of pressure on making whatever was next amazing.  What we produced at first probably wasn’t our best work, but we pushed on, and slowly we started to get back in our grove.  That fall we organized a participatory project with over 800 participants in a downtown park and staged a prank where over 100 guys shopped shirtless in Abercrombie and Fitch (we were asked to leave by the management pretty quickly.)  Both videos took off on our YouTube channel, and Improv Everywhere felt alive again.

Today Improv Everywhere’s content reaches millions of people around the world.  As the web and television begin to blend into one, we find ourselves in the great position of being entirely independent.  Having a national network show probably would have been a life-changing experience, but I in the end, I think finding our own audience has been more satisfying.

If I could give you one piece of advice it would be…

Create exactly what you want to create, and opportunities will come to you.  If you start out looking for opportunities, they will never arrive.

About

Charlie Todd is the founder of Improv Everywhere, producing, directing, performing, and documenting the group’s work since 2001.  Charlie is the author of Causing a Scene, published by Harper Collins in 2009.  Based in New York, Improv Everywhere causes scenes of chaos and joy in public places and has executed over 100 missions involving thousands of undercover agents including the legendary Grand Central Freeze and the infamous No Pants! Subway Ride.  The group’s videos have received over 180 million views online.

Photo by Karen (originally posted to Flickr as tightie bluies) [CC-BY-2.0 (www.creativecommons.org/licenses/by/2.0)], via Wikimedia Commons

I learned fast that this was something much bigger in scope and effort than I imagined.

I started the process by making sure I was proud of the content I created, so I spent 6 months focused only on acquiring great contributors and editing stories. Little did I know that that was just the beginning. Between curating/searching for content, conducting interviews, getting interviews transcribed, editing (and re-editing) stories, building my team, marketing the magazine, finding out how to put it online, working on the technical side of the website, and editing both PDF and website design, I literally had no room to breathe! I remember one time in particular I felt so overwhelmed I just wanted to scarp everything and move to Aruba. Our website wasn’t working properly and because I couldn’t fix the problem or understand technically what the problem was, I felt helpless. Being in that state of helplessness only caused me more worry and anxiety and I realized all I wanted to do instead of tinker with the technical stuff was throw in the towel. At the time, I had my business partner, Clay, with me and he was a huge support during this time, trying to take the lead on the technical end. I think I spent a few weeks, if not months in this state, not knowing what to do.

Ultimately, the way I got myself out of it was not by thinking positive, but by getting really frustrated with my inability to let things out of my control. Here I was, not technically savvy and I expected to understand this highly technical problem right off the bat and solve it to boot! I realized that my need to control and figure out every little thing gets me into trouble. I made the decision to outsource and find someone really skilled in web development to take over the problem and help us. As soon as I made that decision I felt a weight drop from my shoulders and I realized that even though I couldn’t fix the problem, I didn’t feel so helpless any longer and building upon just that small feeling made me feel a lot better.

From there, as soon as that helpless feeling started to go away, I was able to make more decisions and build upon the momentum I gained from those decisions. I think the thing that made me continue also was that I saw the magazine as a tool that I could use for myself, in addition to our readers. I was really creating something I wanted to read so to lose that, to lose all the great stories and lessons and contributors and inspiration, I just didn’t want to go there. I thought it was something so necessary in the world for people that I just wanted to give it my best shot, even though I didn’t know what would come of it.

I had to try.

The One Thing I Wish You Knew

“Don’t be afraid to tell your story and use your own voice. Being real and being you is one of the most powerful “”branding”" and marketing lessons I’ve learned for my own business. “

About

Ishita Gupta is founder and publisher of Fear.less Magazine, an online magazine that profiles leading thinkers and their experiences overcoming fear. From entrepreneurs, business owners, writers, and creatives, to people who’ve survived September 11th, Fear.less reveals how to deal with the challenges life throws at us. It’s been called “Fast Company meets Oprah” by it’s readers and featured contributors include Karen Armstrong, Tim O’Reilly, Danielle LaPorte, Paul Ekman, Tony Hsieh, Howard Zinn, Julia Cameron, Sharon Salzberg, Steven Pressfield and more. Ishita also heads up Media and Partnerships at the Domino Project, a new publishing venture created by Seth Godin and powered by Amazon, where she gets Domino books they attention they deserve.

“Hey Derek – this guy wants to know if we can refund his account after he’s already set it up.”
“Hey Derek – the printer isn’t working!”
“Hey Derek – would it be OK if we start taking lunch in shifts instead of all at once?”

No one question was that bad, but it was a steady stream of them, every few minutes, all day long. I couldn’t get any work done. I felt like I might as well just show up for work in the morning, and sit on a chair in the hallway, just answering questions.

What I wanted (and needed) to do was the programming – the deep work – the stuff that takes many hours of concentrated solitude.

So I decided to quit. Well, quit going to the office, at least. I found an apartment in Hawaii, and agreed to rent it for one year. My employees would just have to do without me, and figure out the answer to all their questions. I would be in Hawaii just focusing on the programming.

This was definitely done out of frustration and anger. This was very clearly running away.

The night before I was to sign the rental contract, I saw the movie “Vanilla Sky”, where Tom Cruise’s company gets taken away from him by the board, because he’s not giving it his attention.

I realized that running from my problems without solving them might mean my company gets taken away from me. I realized this was my dip I needed to push through, to get to the other side.

With a clear head, I asked myself some good questions about this problem. What caused it? Where is it coming from? How can I fix it? What’s my ideal scenario?

I realized almost all those questions were coming from one person: a woman in customer service. I realized I needed to teach everyone at the company the answer to all these questions, so that they didn’t need me for operations anymore.

I cancelled the apartment in Hawaii. I went back to work the next day and moved the customer service woman to a new role. I hired someone awesome for customer service (who still works there now, 9 years later, and is still awesome.) I started teaching everyone everything I knew.

After 6 months of hard work, teaching everyone everything, I had done it. I was free. Nobody asked me anything anymore. They knew my philosophies and strategies. They knew everything I know.

Later that year, my girlfriend moved to California, so I went with her. My company grew from $2M to $20M during the 5 years I was away. All because I had figured out how to push through this dip.

The One Thing I Wish You Knew

“Whatever scares you, go do it. (The best goals feel scary as hell, at first. Later you get to smile that you used to be scared of where you are now.)”

About

Derek Sivers is best known as the founder of CD Baby. A professional musician (and circus clown) since 1987, Derek started CD Baby by accident in 1998 when he was selling his own CD on his website, and friends asked if he could sell theirs, too. CD Baby was the largest seller of independent music on the web, with over $100M in sales for over 150,000 musician clients. After he won the 2003 World Technology Award, Esquire Magazine’s annual “Best and Brightest“ cover story said, “Derek Sivers is changing the way music is bought and sold… one of the last music-business folk heroes.” In 2008, Derek sold CD Baby to focus on his new ventures to benefit musicians, including his new company MuckWork where teams of efficient assistants help musicians do their “uncreative dirty work”. His current projects and writings are all at sivers.org