Rebecca had a new baby. Paul had a dream. Ellen turned 50. Simon was tired of being bogged down by administrative details.

People leave work in the nonprofit sector to become freelancers for a wide variety of reasons. The variety of their stories is instructive for people considering making a similar leap to self-employment.

Something exciting…and scary

As Ellen Kupp approached a milestone birthday, her children were leaving the nest and circumstances changed within her job as the global brand and marketing manager for World Vision. She began to realize that it might be time to move on and try something new.

One mentor said Kupp would know within six months to a year whether she was cut out for freelancing. She decided to leave her organization in such a way that she could come back if it didn’t work out.

She describes the transition to working as a self-employed marketing and communications consultant as “arduous” and says if she were going to do this again, she wouldn?t embark on this change at the same time as her kids were leaving home.

“It took effort,” Kupp says, “to recreate myself, to take the networks I had built and recreate them in a new way.”

She didn’t create a business plan for her company, Kabisa Marketing Communications Inc., but spent a good deal of time working on her website as an exercise in identifying her strengths and capacity. It also took a full year for her to feel settled in her new daily routine, despite the fact that she had already worked from home for a significant portion of her career with World Vision.

“You have to be the kind of person who can live with the vagaries of consulting. The upside is lots of freedom to create who you are, but you have to have the stomach for the ebbs and flows of the freelance business.”

Her children’s tuition bills were good motivation for her to find work but she also creates motivation in playful ways: recently, she and another freelancer decided the first to sign a new contract would receive a bottle of wine from the other. Kupp lost by two minutes.

Another piece of advice she found valuable was to hire an excellent lawyer, accountant and bookkeeper.

Because Kupp is an extrovert, many of her friends told her she wouldn’t survive as a consultant, but technology has made it possible for her to stay connected. She meets with clients primarily over Skype, giving her virtual face-to-face contact. She also works from a local café every morning. Frequented by a variety of home-based freelancers, the cafe’s ambient noise and opportunity for conversation gives her the people contact she needs. She was also able to spend a month with her recently widowed mother, thanks to technology that kept her connected with her work back home.

While Kupp considered quitting her job to be a “big scary leap away from security and community,” working as a consultant has been much less stressful for her than being employed. Being able to pick and choose interesting projects is one aspect of Kupp’s satisfaction, while avoiding inevitable office politics is another. She found that starting her business around the time of the economic downturn was actually a boon, as organizations were more likely to welcome freelancers than to take on new staff.

She also found a strong sense of community among other self-employed people in the sector. “People share work if they are too busy. Different professionals work together depending on the project. It’s less expensive for the client, and gives them good creative energy.”

Kupp’s work continues to evolve, particularly as she is collaborating on several projects with her husband, who recently left his work and has joined her company. Kupp laughs. “There’s always something exciting and scary just around corner.”

More creative space

Just before Simon Trevelyan talked about his work as a freelance fundraiser in the nonprofit sector, he took 40 minutes to meditate, an activity he would not have had time for in his former role as general manager of revenue development at the BC Society for the Prevention of Cruelty to Animals.

Trevelyan had enjoyed the fundraising aspect of his work with the SPCA but much of his time was taken up with personnel and administrative duties. “I like to think outside the box,” Trevelyan says, “and there wasn’t always the opportunity to do that as an employee. More than anything I left because the position didn’t provide me with enough creative space to develop and implement new ideas.”

“I’ve always been passionate about the role of the NFP sector,” he says. “Now I feel I am really contributing in a meaningful way. I love meeting people from the nonprofit sector and learning about their legacy programs. I love helping clients overcome their challenges and providing them with resources that can help them reach their vision.”

Despite the fact that “you have to do a tremendous amount of marketing and customer development to generate an income stream,” Trevelyan says he wishes he had made the move to become a consultant much sooner.

A key to success for Trevelyan was to find a partner.

“When I first started, I was working by myself and I was coasting a lot.” Working with a partner has helped Simon be much more focused and productive.

He believes that his ability to think outside the box makes him an asset to his clients.

“People are much more prepared to listen to you if you come from the outside with a novel approach and idea. Doing that from the inside is much harder.”

Trevelyan feels fundraising in the charitable sector is still in its infancy in Canada, with many organizations, large and small, desperately needing help, particularly in the legacy-giving field. He generates work for his company, ST Legacy Group, by putting on legacy seminars, which are sponsored by nonprofit organizations. He also provides free consultations to potential clients, has a website and is planning to launch a new e-strategy.

Juggling act

Fifteen years ago, when her first child was born, Rebecca Sutherns was responsible for program monitoring, advocacy, campaign planning and government relations for a large international development NGO. Despite the fact that this had been her ?dream job?, she decided she wanted work that was more flexible, where she had more control and would be closer to home.

The decision she made to work as a freelance consultant meant that her work was very close to home &emdash; in fact, it became home-based. Today, through her business Sage Solutions, she offers facilitation, strategic planning, policy analysis and research to clients largely in the nonprofit world.

While she finds the variety of projects and clients stimulating and rewarding, she also believes being exposed to a wide variety of practices and people in the nonprofit sector enhances her value to clients.

She notes, “There are often projects that are well-suited to an external person &emdash; perhaps because they require ‘outside eyes’ or because the funding is not available to hire someone long term.”

Rebecca wishes she had more opportunity to build consistent relationships with colleagues or to work collaboratively on longer-term projects and sometimes feels she misses out on seeing a project through to implementation. But on the whole, she enjoys the challenges and opportunities created by freelancing. She has also developed a network of other freelance professionals with whom she collaborates.

One of the biggest benefits Rebecca sees in being self-employed is having considerable control over her schedule. “The workload and client expectations shift all the time, but if I want to work out or volunteer at my kids’ school during the day, I can.” She adds, “I like not being paid for attendance. Instead, I am able to ‘parachute’ into a work situation, intervene in what are hopefully helpful ways and leave again.”

She notes that project-based work suits her temperament better than a long-term commitment and bureaucracy.

Rebecca is a secondary income-earner. While this relieves financial pressure, it also means she is constantly juggling varying workloads and different types of projects and clients with a busy life with four active children. For Rebecca, like many freelancers, finding enough work, but not too much, is an ongoing challenge.

Not everything comes up roses

Two years ago, Paul Chin left long-time work with students in a university setting, where some of his work had been focused on developing intercultural awareness. He hoped to develop this work as an intercultural consultant with his company Global Interchange Consulting.

However, just as he left his job, the recession hit. While he had experience in the field, he did not have extensive contacts. He also had a young family with bills to pay. He decided he would look for part-time work in his original field of engineering &emdash; and within a short period of time received full-time job offers he could not refuse.

At the same time, Chin continued to pursue his dream, negotiating with his employer for up to 15 unpaid days of leave each year, in addition to vacation, to use in his intercultural work. In 2010, he used eight of those days to work with his former employer and another client on consulting projects. He continues to pursue certification in the intercultural world and is using the training in several community volunteer positions. He is also slowly building his network.

Chin says, “I am still assessing whether I want to do this full-time long term,” uncertain whether he can manage the ambiguity of working with a lack of structure and a paycheck. He imagines the possibility of stepping into a structure that would welcome his skills and training but is still considering whether he wants and is suited to creating such a structure for himself.

Things to consider before stepping out on your own

Know thyself

• Figure out how extroverted you are. How else might you get your people needs met?
• Does having a manager and a schedule make you more efficient or hamper you?
• How do you feel about marketing yourself and having to regularly generate work?
• What do you love to do? What problem does it solve? Is it marketable?

Who do you know?

• Who’s your target market?
• Do you know at least some of your potential clients?
• Take stock of who you know and define how they might help you.

Money, money, money

• How much financial commitment do you have? Is your spouse comfortable with this change?
• What will you do in a slow month? How stressed out will you be?
• What will you charge? How much will people pay? How much do you need?
• Understand whether you are more risk-averse or entrepreneurial.

Chart a course

• Read books and websites about launching your own business.
• Talk to people who’ve made the leap and those who know you well.
• Get an accountant, a lawyer, a bookkeeper and/or other resources.
• Make a business plan and sketch out your potential website.

Is the grass greener?

• Why do you want to leave your current position? Could you do what you do better in a different job or on your own?

Susan Fish is a writer/editor at Storywell, a company that helps individuals and organization tell their story well. She has written for the nonprofit sector for almost two decades and loves a good story.