Making the Transition

You might be a born entrepreneur, but that doesn't mean you're ready to own a business. With our help, though, it'll be a smooth evolution.
Magazine Contributor
8 min read

This story appears in the March 2001 issue of . Subscribe »

After repeated attempts at squeezing your square self into a round hole, you finally admitted it wasn't going to work. You said good-bye to corporate America and bravely embarked on a journey toward the greener pastures of entrepreneurship. You carried with you tons of tangible information-details on marketing, health insurance and places to find cheap office supplies. The one thing missing from your backpack was an understanding of the myriad of changes you'd experience as you made your way through this transition.

If you find yourself sitting in your office, blasting the stereo and fighting the temptation to surf the Internet until your eyes bleed, you're not alone. According to Manhattan psychologist Dr. Vicki Ianucelli, we are conditioned, from the time we first step foot in school, to function optimally in a structured environment, so the idea that you can actually ditch this kind of life isn't always top of mind. "In making the jump from a 9-to-5 job to trying to establish a business, you need to create a new reality," says Ianucelli. "That's very difficult."

For Dawn Lloyd, 31, owner of KDL Enterprises Inc., the parent company of pregnancy and parenting Web site, it took some time to create that reality. "I was terrified I was going to sit on the couch and watch Oprah all day," says Lloyd, who runs her business from her home in Winston-Salem, North Carolina. "If someone wasn't watching over me and signing my paycheck, would I work?"

It took several months of promising herself she wouldn't turn on the TV during working hours before Lloyd's entrepreneurial routine became a habit. But with self-discipline and the determination to overcome her fears, she did it. "When I realized I had made it past that point, it was amazing!" she happily recalls.

The flip side to entrepreneurial paralysis, of course, is entrepreneurial overload-those times when you just don't know when to call it quits for the day. As Todd Brabender, 35, owner and president of Spread the News Public Relations Inc. in Lawrence, Kansas, puts it, "When you're a business owner, sometimes the 5 o'clock whistle blows at midnight."

George Cigale, 32, founder and CEO of, a Manhattan-based company that seeks to unite educators and students, knows what it's like to see the dawn during the start-up stage. "There were times when I was literally rolling out of bed and walking, or crawling, over to the desk," he laughs. "The day would restart because I had 100 e-mails to write, and then suddenly the sun would be coming up."

Avoid the Extremes: Find Your Equilibrium

Balance is the solution to these challenges, according to Anne Louise Feeny, a management consultant and creator of Trail Boss Management, a program wherein managers learn to emulate the Old West's trail bosses. "Keep one calendar that tracks both business and personal dates," she advises. "It's important to schedule fun times. Write both your business and personal plans for the week."

This is a necessary step to take, because if you don't, chances are, no one will. "Friends will hesitate to call because they don't want to disturb you," Feeny cautions. "You think about calling them, but you don't. You end up being an unwilling hermit."

Feeny advises scheduling events outside the office on a regular basis to prevent getting trapped in a merry-go-round of isolation. "Look in your area for low-cost, multipurpose events," she suggests. "Brown bag lunches or discussions sponsored by local universities or business organizations will get you out of the office and help you build a professional network."

These types of activities will also help foster an understanding of entrepreneurship in society. As a business owner, you have been essentially disenfranchised from the community of the 9-to-5 worker. You have lost the privilege of perception. In America, the first thing people want to know, after your name, is what you do-and when you tell them you're a business owner, you can get looks that range from "Poor guy. I wonder what really happened at his last job," to "Is she crazy? No benefits? How will she support herself?"

Jean Barnett, 32, a partner in Thirty-Three Productions, a New York City production company, can relate. Says Barnett, recalling a conversation she had with a young man on the ferry in Seattle: "He asked, 'What do you do?' I didn't know which hat to put on. I didn't have the job title with the desk, the nameplate on the door and the corporate business card."

No doubt about it, our culture is big on labels. "We learn through the process of maturation to put labels on things," confirms Ianucelli. "We believe we know what constitutes a 'good job' or making 'good money.' When you venture out on your own, you need to redefine those things."

The best way to deal with the looks and snide remarks is to build a support system for yourself. Cigale believed a support network was so crucial to his sanity that he relocated from the Boston area to New York, where he and his wife both have family. "[The move] had a real effect on me being able to do my work [well and] have a fulfilling life outside my business," he offers.

At the same time, you may find you'll need to educate your loved ones about what entrepreneurship entails. Amanda Formaro, 33, owner of, an advice Web site for parents, confesses she and her husband had a hard time in the beginning. "He and I fought constantly," says the Kenosha, Wisconsin, entrepreneur. "He couldn't understand what I was doing on the computer all the time. Sometimes the people closest to you have a challenge in supporting what they don't fully understand."

Formaro credits Friday night dates and solid communication for getting them through the transition. "It also helped when he began to see checks coming in," she laughs. "These days, he asks me how many page views I received the night before. He's not quite sure of the whys and hows, but he loves and encourages me even though he doesn't really understand what I do."

Building Your Inner Foundation
We talked with some spiritual experts to get their take on transition. Even if you don't consider yourself a spiritual or religious person, their lessons can be applied to your life as an entrepreneur.

Justin Epstein, associate minister of the Unity Center in New York City, stresses the importance of spiritual community.
"It is important for us to carefully choose our friends and the company we keep. If you spend time with people who have pessimistic attitudes, then you will subconsciously be pulled down by them."

Rabbi Alexis Roberts of the Congregation Dor Hadash in San Diego points out that people often place spirituality in the same category as entertainment and relaxation-things they're willing to sacrifice for a while until a new business is stable.
"When we're making a living, we need to question what we're living for-our family, the community, the world? Work is one of the games we play when we're alive. It doesn't have lasting significance in itself if it doesn't serve a higher purpose."

Darry Guli and Eva Garrity, owners of The Yoga Studio in Fairhaven, New Jersey, acknowledge the importance of both inner and outer sources for creating a strong spiritual foundation.
"Spirituality is often in the last place you expect it to be," says Garrity. "Be honest about what you're doing with your life when you talk to people. Be willing to open up and observe what is going on around you, and you will find the answer to any question you have."
Guli stresses the importance of looking within: "Follow your intuition. Do whatever you've done in the past that makes you feel like you're on your path. You usually know what that is when you get quiet."

Repeat After Me: I'm Good Enough...I'm Smart Enough.

All these transitional strategies won't mean much if you don't have faith in your own abilities, however. As Cigale puts it: "I have to have complete confidence in myself in order to solve problems and adapt the business to consumer needs. I try to project complete confidence, even when I don't have it."

To help build that conviction, it's crucial to take care of yourself at all levels. For Brabender, it's meant joining a gym and watching what he eats. Barnett, meanwhile, has become an "information junkie," reading like a fiend in order to educate herself and forward her success.

Still other entrepreneurs find comfort in believing in a higher power. For Barnett, "it's as important as a business plan," she says. "The type of faith you have will determine the kind of business you have."

Self-affirmations, meditation and contact with like-minded people can all help you create a solid inner foundation. But above all, trust in your decision to become an entrepreneur, even on those days when you're longing for the "stability" of a 9-to-5 environment. "Don't look back," advises Brabender. "Affirm that your decision is the right thing for you. The transition will continue daily, if not by the minute. The reality is, it's just another rung on the ladder of your life."

Staci Backauskas is a writer, speaker, teacher and the author of The Fifth Goddess. She writes frequently about spirituality and runs a Web site at


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