Ready to Step Out of Comfort Zone on Road to Entrepreneurship

Image representing step out of comfort zone to leave corporate america

Go ahead! Step Out of Comfort Zone on Road to Entrepreneurship! Are You Ready?

In this post, people from all walks of life share what happened when they decided to step out of comfort zone land on the road to entrepreneurship. Was leaving corporate America a TRICK OR TREAT?! I think you will find a trend here in these entrepreneurs’ stories…read on and Happy Halloween!

Is it a Trick or Treat to Step Out of Comfort Zone?

step-out-of-comfort-zone-matt-michelMatt Michel, CEO of The Service Roundtable TRICK! I left corporate America to start the Service Roundtable, an Internet-based contractor business alliance. The trick is that success followed and 10 years later the Service Roundtable is a multi-million corporation. I’ve grown my way back into corporate America, though I wouldn’t change a thing.
step-out-of-comfort-zone-dan-nainanDan Nainan, Comedian/Actor/Voiceover Artist/Computer Expert TREAT! My job as a senior engineer with Intel Corporation was to travel the world with Chairman Andy Grove doing technical demonstrations on stage at events. I was incredibly nervous about speaking on stage. So I took a comedy class to get over the fear, and the comedy kind of took off. Since then, I have performed at the Democratic National Convention, at a TED Conference, at three presidential inaugural events, for Hillary Clinton, for Donald Trump at his golf course in Palm Beach, for Apple cofounder Steve Wozniak, and for many similar luminaries. I recently performed at the Kennedy Center in Washington DC and on the MDA Labor Day Telethon with Carrot Top and Penn and Teller. Also, I appeared in an Apple “Get a Mac” commercial. I perform all over the States as well as in many foreign countries. My life is like that of George Clooney in “Up in the Air”, just without the sex LOL.
step-out-of-comfort-zone-andrew-schrageAndrew Schrage, co-owner of Money Crashers Personal Finance TREAT! Leaving my hedge fund position several years ago to work on Money Crashers has absolutely been a treat for me. I’ve learned a lot and have had fun at the same time. Furthermore, my business has been able to expand due to the extra hours I have been able to put in. The transition was by no means seamless or stress-free, but by working hard, continuing to grow, and remaining passionate about what I do, I’ve been able to enjoy a great deal of success. In entrepreneurship, there’s a new adventure every day, and I welcome all challenges that small business ownership brings.
step-out-of-comfort-zone-rob-schutzRob Schutz, owner of TREAT! Breaking free from ‘the man’ is as liberating as it gets. But, also, a TRICK because then you realize you have no paycheck. And you’re relying solely on yourself. Eating ramen every night suddenly becomes a given. I left a corporate consulting job in 2009 to pursue my own business, What’s the Deal. WTD was early to market in the daily deal space and Irode that wave to its peak, ultimately selling to a competitor in 2011. Now, using the skills acquired from building WTD, I’ve launched my next company,, a resource for discovering live-tweeting across TV, sports and politics.
step-out-of-comfort-zone-dorian-smithDorian Smith, owner of and author of “Mind Games TREAT! I left “corporate” life over three years ago in 2009, during the height of the [recent] financial crisis to start my own business, Big Apple Style Marketing. Most of my friends and family thought I was crazy, but it was the best choice I ever made. Having control over my own schedule, and the ability to take on the clients that I wanted, when I wanted, was the most freeing thing in the world. Three years later I’m living my dream, working with Japanese artists, and utilizing my creativity every day!
step-out-of-comfort-zone-cynthia-okimotoCynthia Okimoto, owner and primary caregiver of New York Dog Nanny TREAT! I went from a dog-eat-dog world to dogs are my world when I left The Moret Group in 2010 to start my own dog nanny service in New York. It mortified me to give up a stable job especially one that was a gateway to launching my career and was the perfect cultural right after the stock market crashed. Though hiring freezes ran rampant and companies were cautious bringing staff on in my field- HR which is normally the department where people get laid off first in tough economic times, I knew this was the greatest gift I could give myself.
step-out-of-comfort-zone-beverly-solomonBeverly Solomon, creative director for musee-solomon TRICK! Until I could build up my business. But emotionally, leaving the corporate world of fashion was a TREAT! . I was a model and then an account executive in sales and marketing for Diane von Furstenberg, Revlon, and Ralph Lauren. I was ready to use my expertise, contacts, and experiences to start my own business. I was successful at what I did, but tired of doing it for the company instead of for myself. I now run my successful international art and design business north of Austin, Texas, with my husband who is internationally recognized artist and award winning Green designer, Pablo Solomon. My expertise in art has been featured in books, newspapers, magazines and TV. I have also received coverage in a number of financial publications and was given official recognition by the State of Texas for my business savvy.
Shaun Eli, Comedian and Executive Director, The Ivy League of Comedy and TREAT for me, TRICK for them (their loss)! I was a bank vice president (Bank Hapoalim’s NY office) for a decade when I left to become a full-time stand-up comedian. The big treats? Being my own boss means not answering to anyone else AND the freedom to fire any clients I didn’t wish to work with. Oh, and my alarm clock? I’ve forgotten how to set it (seriously, I forgot which buttons do what, so now I use a kitchen timer on those rare, rare occasions when I have to wake up at a certain time).
step-out-of-comfort-zone-guillermo-ortizGuillermo Ortiz, Founding Geek of Geek Powered Studios, LLC TREAT! Leaving corporate American behind was the scariest thing I’ve ever done. As demanding, monotonous, and stressful as it was, [the corporate job] did provide a sense of security that quickly evaporated when I forged forward on my own. Once I built a stable base of clients for my Internet marketing company and starting gaining momentum, it has been nothing but excitement and self-growth. I look forward to each day’s challenges because I know that I am creating my own destiny. There is a deep satisfaction in knowing that I get 100% return on my blood, sweat, and tears.
Andrew Holtz, MPH; Chief, HoltzReport TREAT! 15 years ago I was a CNN Medical Correspondent. I wanted to return home to
Portland, Oregon. CNN denied my request to work remotely, so I left. It’s been a great treat. Starting with freelance assignments with PBS and international outlets, I branched out into magazine writing and then three books about the medicine on House and Grey’s Anatomy. I had the freedom to pursue a Master’s Degree in Public Health and time to devote to getting the Association of Health Care Journalists off the ground. My pay bounces up and down, but the control I have is priceless.
step-out-of-comfort-zone-bruce-specterBruce Specter, Advisory Mortgage Planner, New American Mortgage TREAT! After being politically assassinated for being more concerned about our customers/business partners then we did to Wall St (I ran a business segment for a Fortune 500 company, since gone bankrupt), I found myself disillusioned with the whole corporate thing. I came home on Valentine’s Day the year I was to be married and telling my then fiancée that I was giving up the high paying corporate gig and going into the 100% commissioned world as an independent mortgage broker. We just celebrated 20 years together (I married way above my pay grade!!). I just needed to let the entrepreneur out!
step-out-of-comfort-zone-robert-slocumRobert Slocum, Owner and Master Service Technician, Pf Pools and blogger at  EngineerToEntrepreneur TREAT! Leaving the corporate world has had a wonderful benefit for my health. I started my own business in July of this year and have found that my clothes fit better, my blood pressure is lower, my eyes are never tired anymore, and I always have a big smile on my face—which may be the most important. The change from engineer in the corporate world to entrepreneur in the real world has given me both a better quality of life and a longer life as well.
step-out-of-comfort-zone-ellen-mastrosEllen Mastros, serial entrepreneur and owner of New Work New Life  TREAT! I left my corporate job over 20 years ago and have never regretted it. I have a B.S. in Business/Accounting and worked for a company called Memorex-Telex that no longer exists. I started in finance but moved to logistics and product management in the 7 years I worked there. I felt like a small cog in the big corporate machine and what I disliked about the big company was that I knew that if I got run over by a bus I could be replaced in a few days and no one would know the difference. I left to start my private practice business as a self-employed massage therapist…that’s a 180 degree turnaround…and have never worked in a corporate environment since. I have had many jobs/business ventures since then. It is now my passion and my new business to help other “corporate slaves” free themselves and find work that is rewarding and enjoyable. Change your career and change your life!
step-out-of-comfort-zone-barry-maherBarry Maher, owner of Barry Maher & Associates and author of Filling the Glass newsletter TREAT! When accounting told my corporate VP I’d been slightly overpaid for a year, he decided to threaten me: pay the money back or else. I simply resigned. And began consulting, writing, and speaking. Within a year, that same company brought me in as a consultant, at a rate several times higher than the “overpayment” rate. And several years later,  that VP got to sit in the audience and listen as I delivered the opening keynote at his new employer’s annual conference, for a daily fee far more than what I’d been “overpaid” in a month when working for him.
step-out-of-comfort-zone-myra-cisseMyra Cisse, MBA, owner of Certification Consultants LLC TREAT! I resigned from my career as a Business Banker on June 1, 2012, and it has been the best treat. I began building my business the year before I left. Although I wasn’t totally comfortable with my ability to support myself with my business, I KNEW it was time to take the leap of faith. When I did, opportunities I could not have dreamed became available.. By clinging so tightly to the perceived security of my corporate career, I was not free to accept the plethora of opportunities that were available and now my certification consulting business is flourishing.
step-out-of-comfort-zone-tricia-meyerTricia Meyer, owner of Sunshine Rewards TREAT! Starting my own business wasn’t easy, but at least my efforts were rewarded. At my corporate job it didn’t matter how much time, energy, or enthusiasm I put into my work; the results were the same as for everyone else around me no matter what they were (were not) putting into the job. Working for myself, I reap more benefits the harder and smarter that I
work. My talents are no longer being wasted. It’s energizing and encouraging to see the direct results of your work.
step-out-of-comfort-zone-eric-thomasianEric Thomasian, Business Development & Strategy, online video tech start-up Blayze, Inc TREAT! After leaving corporate America, I was able to jump 2-3 rungs up the corporate ladder. VP-level clients who typically would be my boss’s boss are now my direct counter parts. Also, managing a multitude of simultaneous projects, I am able to directly contribute to the progress of my start-up. This is very self-satisfying especially since working in Los Angeles I work with many of the top networks and studios. Working at Accenture, I’ve consulted for YouTube, eBay, Symantec, Pfizer, and Cisco.
step-out-of-comfort-zone-marybeth-reevesMaryBeth Reeves, Chief Executive Mamma at Scrapbook Mamma TREAT! In December 2008 my position as a Corporate Trainer for Starwood Hotels and Resorts was eliminated and I found myself without a job after 11 years with the same company. As a result, I took my hobby and started my own business. My company is called Scrapbook Mamma and I make custom photo books with personal photos and other mementos for other people. Saying I have taken a cut in pay is the understatement of the year, but I am so happy to be putting my efforts to a company that is my passion and gives me so much joy.
step-out-of-comfort-zone-jennifer-bournJennifer Bourn,co-founder of Bourn Creative, LLC TREAT! I left corporate America pregnant with my second child. It was relatively easy to get started and within a year I hit six-figures. Seven years later, I have a thriving business, my husband has taken over as CEO, we have a killer team, and we are living life on our terms. I left corporate America to spend more time with my family and children, and have more freedom and that is exactly what we all are enjoying now. While it was scary at the time, starting my own business was the best decision I have ever made.
step-out-of-comfort-zone-tricia-chavesTricia Chaves, creator of Cover Look Collection TRICK? No, TREAT!  Leaving corporate America was a treat, disguised as a trick. After losing my real estate management position in 2008, I began blogging and publishing articles online to pass time while job hunting. My hobby evolved into a career as a freelance writer. I created Cover Look Collection with tutorials by celebrity beauty pros. I became the natural beauty guide for and published work on USA Today. More free time and flexible schedule allows me to work from home (which is presently Rio de Janeiro) and commit to my Thousand Locks for Cancer charity and a book project with Mahri Martens


Steph Calvert, owner of Hearts and Laserbeams

TREAT! I worked as a graphic designer in Los Angeles. I negotiated telecommuting to eliminate the long commute. My art director loved my work; my designs were getting sales. Life was *great*. Then I went on maternity leave, returning to a new art director. She hated my telecommuting, no matter how well it worked. She was less than professional about it. Three days later, I quit my job and became self-employed with Hearts and Laserbeams. Every single one of my bills has been paid since I quit my job in December 2010.


Impressive, huh? Comment below to share your experiences, good and bad. Did you step out of comfort zone land to take the road to entrepreneurship? Want to, but can’t? What’s holding you back? We want to hear from you!
Need marketing advice for your new start-up or a makeover of marketing strategy and web design for your long-time entrepreneurial endeavors? Contact us! Happy Halloween!



By Wanda Anglin

Wanda Anglin has a passion to help businesses and non-profits reach their goals by attracting more of the right website visitors. Her empathy and understanding for small business challenges comes from a background in project management, sales support, accounting, and business ownership. When not helping clients, Wanda is traveling, fixing her home, or tending to her 900 trees (really).

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