Self-Employed to Employee: Making the Switch

Be ready to explain your motives and your unique value to a boss.


There are plenty of benefits to working for yourself. The flexibility, the autonomy, the ability to build something: All are great lures for those who like the challenge of an entrepreneurial business.

However, the same factors that attract people to self-employment can also become a burden. Autonomy can mean having no one to bounce ideas off. Flexibility means you can take time off during the week, but you may also find yourself working through the weekend. And when you need to spend as much time marketing your business as you do working with existing clients, you might wonder if the grass is greener on the other side of the cubicle.

In addition, the economic downturn has stalled business growth, prompting business owners to trade autonomy for a steady paycheck.

Those who make the transition from entrepreneur to employee join the pool of wage-earners already on the job search, but they face different challenges, said recruiters, human-resources managers and those who have made the transition.

Many of these job seekers question what line of work to choose after years wearing multiple hats; most struggle to match the standards of a corporate hierarchy against which they’ve never been measured; and all must come to terms with handing control to someone else, starting with the job interview. They must also battle the perception that they are abandoning a failed business or could prove unmanageable within a corporate structure.

The employer is concerned about the entrepreneur’s experience as well as his intentions, said Caroline Ceniza-Levine, a partner at SixFigureStart, a career-coaching firm based in New York.

“HR might be thinking, ‘OK, this person has been on their own; are they going to just come here and hang out until things get better?’ He will need to come up with compelling reasons why he wants to go back to the corporate lifestyle,” she said. “The prospective employer wants to feel they are selected, rather than think the candidate is running from something else.”

“Why do you want to work for someone else again?”

For whatever reason a person decides an office job beckons, making the transition poses some real challenges for job seekers, who will be scrutinized by hiring managers trying to determine whether they can truly function in a corporate hierarchy. Indeed, someone who has managed a business but not necessarily a staff is a bit of an unknown when it comes to her place in that hierarchy. And the job seeker needs to be prepared to answer one inevitable question: “Why do you want to come back to an office?”

Instead of waiting for a hiring manager to raise them, a job seeker needs to ask herself these questions at the beginning of the hunt.

It’s an exercise Linda Hall, president and senior partner of Wakefield Way Consulting in Rochester, N.Y., advises her C-level executive clients to conduct before they send a single resume. It’s up to the job seeker to present the image that he isn’t running away from a bad experience but offering something valuable to the corporate world.

“Typically, the person who has pursued an entrepreneurial career is someone who is passionate about what they do and is driven to create results,” Hall said. “Even if they have decided, because of economic conditions, they need to pursue a corporate job, they need to keep in mind this is one more business decision. In essence, what they are doing now is creating a contract within an organization to provide services.”

Going rogue?

If you’re going to convince an employer that you can provide value to his company, you’ll need to draw on all the skills you’ve used to make your own business succeed. One of the biggest challenges is convincing an employer that you want to work within a company after you’ve been working solo for many years.

Wayde Gilchrist, a freelance IT consultant in the Dallas area, is considering a move into the corporate world as the economic downturn has forced him to reduce his fees.

Gilchrist, who has worked as an independent consultant for 12 years, admitted that his first choice is to work from home. But he said he is realistic about the way the business has changed; he’s convinced that to continue doing the work he likes, he will need to go to work for a company.

He would like to be hired for a management position or even a chief technology officer position, he said, but he is concerned about how his management skills will be perceived. “As a freelancer, you are a one-man team,” he said. “There were occasions where I had to direct a few other developers, but mostly I did everything for myself. HR departments are looking at how many employees reported to you and how big your teams were.”

Ceniza-Levine suggested the candidate pitch the potential employer the way he would pitch a prospective client. “Research the company, identify their pain points, find out what is keeping them up at night, and offer a solution,” she said. “The solution has to be framed around you being there, working for them long-term.”

Addressing his chances of moving into a management position, Wakefield Way’s Hall said Gilchrist does need to think realistically. “Managing other people and their performance is a skill,” she said. “I’ve seen people fail when they follow the line of thinking that to make more money, they need to move into management.”

Gilchrist wondered if he is thinking realistically by looking for openings at a startup, entrepreneurial company that might be looking for someone with years of IT experience, who can manage smaller teams, or even a group of independent contractors.

That makes sense, Hall said. “A startup is more likely in the same frame of mind that he has been in. They will speak the same language.” Still, it’s tricky, she said. Really to know if management is the right place for Gilchrist, Hall said, “the first thing he needs to find out is what the company’s expectations are, and have an honest conversation about whether you can be successful with their expectations.”

Entrepreneurs in Gilchrist’s position should find a trusted client or two, she counseled, who will give him an honest assessment of his personal skills and management style. “Find out how you work, how you drive performance. That way, you can be aware of how you motivate people, and you can bring that awareness into the new environment.”

Articulate your value

Even if someone has managed a staff for many years, her management style and value is a big question mark to a potential employer. After all, there are no performance evaluations, no peers at the company who can give her a recommendation.

After owning a successful landscaping and snow-removal business in Lake Tahoe for 30 years, Scott Schumacher was hit hard by the decline in the housing market. His clients in the upscale Incline Village area cut landscaping services from their budgets as a decline in tourism took a toll on the local economy and housing values fell.

“Business went from really good to mediocre to nothing,” he said. In the past year, he has sold his equipment and is looking to start over in another area of the country where he can use his expertise in managing crews and dealing directly with clients.

“I have been looking for a management position. That’s what I’m good at,” he said. “But nobody is hiring.”

Schumacher is not only trying to sell himself to a company, he’s doing it in areas far from where people know him. His first challenge is to articulate his value to those who don’t know him or his former business.

Rather than seeking an existing job, counseled Hall, Schumacher needs to think about creating business proposals for potential employers. “The idea is to co-create an opportunity with a company that has a need,” she said. “Think about how you can become an adjunct inside an existing business. How can you bring bottom-line results to the company?” In Schumacher’s case, this might mean selling his expertise doing estimates and bringing projects in on time and on budget.

Matthew Arrigale, VP for Human Resources, Americas, at Schott North America of Elmsford, N.Y., said it’s important to be able to tell an employer what skills you utilized in running your company. “Try to relate it to the gap the company has,” he said. “Explain how they can fill that gap by hiring you.”

The need to relocate adds another layer of complication for this type of job search. The strategy, said SixFigureStart’s Ceniza-Levine, is to pick a city or region where you might like to be (even if you aren’t certain) and start researching. “Look on LinkedIn to see if you can find professional groups in that area. Talk to the chamber of commerce; do good, old-fashioned research. In forcing yourself to commit to a target, you will find out quickly whether you’ve picked the right place. If it’s not right, you can move on. But at least you have started looking.”

The job-change challenge

Not all independent contractors have jobs that can translate into corporate work. Re-tooling yourself, and your resume, to fit a corporate job description presents unique challenges.

Kitty Koenig, who owns an international event-planning company in Connecticut, is facing those challenges. Her business has been hard hit by the recession, as Fortune 500 companies have pulled back on events. Koenig, no stranger to re-inventing herself, is considering how she could convert her skills as an international event planner with executive-level relationships, philanthropic fund raising and command of several languages into a position as a personal assistant to a CEO or other high-level executive.

Koenig said her efforts so far have been frustrating. “These are the types of jobs where you need to be personally recommended,” she said. “I feel like I am sending my resume to outer space when applying to online job listings.”

Ceniza-Levine said Koenig is correct in thinking that this type of job won’t be found by sending someone a resume. “The person she wants to work for is not going to find a personal assistant by sifting through resumes,” she said. “And the fact that she is looking to change careers means someone is going to have to take a chance on her. She needs to take those great relationships she has had with her business and use them to get personal introductions. It’s a very personal job, and she needs to work her relationships. Most of her leads are going to come two or three degrees of separation out of her immediate circle.”

A resume, even if it’s not the first point of contact, is still an important part of the job search. For someone who is looking to make a change, Schott North America’s Arrigale said, you can position yourself as someone who is open to new challenges.

“Companies value diversity, new ideas and people willing to take some calculated risk,” he said. “That’s how entrepreneurs operate, and that’s attractive to many employers. Their resume should state how they were flexible and dealt with change and how they were able to innovate.”

Determining whether you are making the right decision to enter the corporate world – whether for a return engagement or for the first time – means taking the time to have some honest conversations, both with yourself and trusted colleagues.

“In this type of economy, people want and need to work. For whatever reason they make this decision, they should go into it with their eyes open,” Arrigale said. “People can be successful in different types of environments, but they stand a better chance if the company’s culture is in line with your personal values.”