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Friday, November 15, 2019
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Tips & Training

From entrepreneur to employee: Helping clients manage the transition

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Self-employment has been long recognized as a viable option outside of the traditional employment realm. The desire to branch out on one’s own and run the show, flexibility from the confines of traditional employment and income potential are some of the motivators for people who choose this type of work. However, the switch isn’t always permanent. Changing priorities or interests can prompt a move back into traditional employment.

Many entrepreneurs enlist the expertise of a career professional to help guide their journey and successfully integrate back into a traditional employment role.

Making the transition

Mark* is a former client who benefited from a series of strategic career coaching sessions to help him make the transition from business owner back to employee. After 25+ years in business, he decided to pursue other opportunities due to irreconcilable differences with his business partner. At the time of his departure, he hadn’t decided whether he would pursue another self-employment venture or return to traditional employment. Mark reached out to me to help him navigate the job market and explore potential opportunities, additional training requirements and create his personal brand. Through a series of targeted coaching sessions, I was able to help Mark improve his job search efforts, harness his network connections, and learn how to recognize and effectively showcase his transferable skills within the resume and interview process.

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“I gave myself six months to figure it out. I wasn’t sure what the next 20 years of my career would look like,” Mark says. Upon leaving his company, he connected with industry colleagues to let them know he was no longer associated with his former business. Subsequently, it was through one of these connections that he was offered an opportunity with a large corporation. However, he had some concerns.

Mark confesses that he was apprehensive about dealing with the corporate hierarchy. “When you’re in your own business, you’re accountable for decisions and profit; however, in a corporate structure, decisions are made whether you agree with them or not.” Although this remains a struggle for him, through focused coaching sessions, he has learned to relinquish his inherent entrepreneurial sense of control and recognize that although his new position is an important part of the equation, he’s not solely responsible for the company’s success.

Kamee Gilmore, an industry colleague, had different reasons for seeking a traditional employment role. Self-employment was a good fit for the needs of her young family, enabling her to stay at home with her children and contribute financially to the household. When her children went to school full-time, the lure of extended health benefits, consistent hours and stable income were contributing factors in her decision to make a career transition.

Challenges moving forward

One of challenges Kamee faced was finding a company that reflected her values, and a culture that matched her personality. She also wanted to earn a comparable salary and have flexible work hours.

It took two years to land her dream job and she admits she had to overcome feelings of failure. She also found it hard to let go of the company she had built. “After single-handedly building a company from the ground up, I realized how deeply emotionally invested in my business I really was.”

Mark and Kamee had different views on how to approach their self-employment during the job search process. Kamee felt it was necessary to minimize her past self-employment endeavors to secure an initial interview, whereas Mark felt that years running his own company and his industry reputation helped tremendously with his transition.

Transition tips from the career pros

Karine Touloumjian, Founder and Certified Resume Strategist at Distinct Résumé, has worked with clients transitioning back into traditional employment. She says that the biggest obstacles for the jobseeker are “selling themselves as an employee after they’ve been self-employed for a number of years and convincing a potential employer they can integrate smoothly into traditional employment, including adapting to less flexibility and control in their work. ”

To help navigate these employer concerns, Career Story Founder Kristin Vandegriend recommends career professionals work with clients to develop a narrative. “Sometimes businesses end negatively because they weren’t financially successful, or they had a falling out with a partner. I’d help the client craft a story that would feel honest yet give a plausible reason for why they were looking to transition.”

On a personal note, Vandegriend offers some insight to her own transition back to traditional employment. “When I tell my story, I focus on how I felt a bit isolated and wanted to be part of a team again.”

Lisa Taylor, President of Challenge Factory, recommends a targeted strategy when approaching potential employers and emphasizes the importance of clients knowing their story and feeling good about it. “Being able to articulate what they’ve learned from their self-employment and why they’re excited to bring those skills and talents to the new role is key. If the client doesn’t feel good about this change, they won’t shine. We spend a lot of time exploring how this change touches on their identity and sense of self.”

The transition to employment within a corporate environment can be challenging but the skills honed as an from self-employment are transferable and will support the adjustment into a traditional job.

Christine Cristiano, President of Ideal Career Services, is a Certified Career Strategist, Career/Interview Coach and Resume Writer specializing in empowering mid-career professionals in a career transition to navigate the job market. She is an active member and volunteer with Career Professionals of Canada and hangs her hat in the greater Toronto area.
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Christine Cristiano, President of Ideal Career Services, is a Certified Career Strategist, Career/Interview Coach and Resume Writer specializing in empowering mid-career professionals in a career transition to navigate the job market. She is an active member and volunteer with Career Professionals of Canada and hangs her hat in the greater Toronto area.