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With all the focus on side hustles and entrepreneurship, it now seems like the natural career cycle is to go from the corporate rat race to the freedom and creativity of self-employment, not the other way around.

In reality, few individual career paths are so linear. Whether it’s a need for more stability and better benefits or just a desire for change, it’s not uncommon for former freelancers and entrepreneurs to find themselves giving up being their own bosses to work for an established company. But how do they do it? And how do they get used to the transition?

The Grass Is Always Greener

If you’re dreading going from freelance to full-time but find yourself having to make the transition, remember that there are benefits to both types of work, and while you might enjoy the freedom that comes with being your own boss, there are plenty of upsides to working in a more structured, established work environment.

David Everett Strickler, a former entrepreneur who now works as a marketing director, started his own consulting business in 2013. But after three years, he found himself ready to head back into the corporate world. His reason? He wanted to work with other people again.

“Freelancing and owning your own business is truly rewarding, however, you are all roles in one and it is often rare to collaborate and work as a team given this environment. I longed for that feeling again and wanted to leverage what I gained operating on my own back into the corporate realm,” he said.

Another benefit? Benefits. When you work as a full-time employee for a company, you’ll likely have access to benefits you wouldn’t get as a freelancer or small business owner, such as health insurance and paid vacation time. You’ll also likely gain access to employer-sponsored retirement plans, which can often include a company match for 401(k) contributions.

When you work for yourself, you’re responsible for everything, including figuring out taxes and keeping thorough business records. This can mean you have less time to do the thing you got into freelancing to do and more time taking care of administrative tasks. When you work as a full-time employee, your company takes care of these things for you, allowing you to focus on your job.

If you’re looking for more security and benefits or are just tired of the constant hustle to find clients and keep yourself afloat, moving on to a full-time job might be a better fit for you than you think.

Play to Your Strengths

So, how do you make the transition from freelance to full-time? You have tons of practical experience running your own business, but you may not know how that translates to strengths you can highlight in a résumé or an interview.

The good news is that people who have been self-employed have a lot of attributes that can help them stand out in the job hunting process.

Dan Ngoyi, Director of Talent Acquisition for Quicken Loans, said that some of the core qualities Quicken Loans hiring teams look for that he commonly sees in self-employed candidates are grit, determination, creativity, being unafraid of taking risks and business acumen.

“A lot of entrepreneurs and small business owners have the ability to set clear direction and take feedback really well,” Ngoyi said.

He believes that people with this background work really well in technology and sales positions. Because of what is required of them in running their own businesses, they tend to be very technically savvy and have good marketing skills, he said.

While it can seem intimidating to go into a more formal work environment, keep in mind that you have plenty of real-world experience to prove your worth. Think about the ways that experience makes you an asset and how you can highlight that on your résumé and in interviews.

Be Prepared to Answer Some Tough Questions

When you’re interviewing for jobs, Strickler warned that you’ll likely be asked about why you want to change jobs.

“Every single interview I took part in after leaving my freelance business included ‘So why leave freelancing behind?’ You want to have a genuine and compelling reason for doing so and be able to articulate that in a way that resonates with hiring managers and recruiters alike,” he said.

According to Ngoyi, interviewers who ask this question want to know that you’re leaving self-employment for the right reasons. If you’re leaving because you had trouble finding success or if you have a history of jumping from one project to the next, that can be a red flag for hiring managers.

A better answer, he said, would involve talking about how you’re looking for more stability and the opportunity for growth that a bigger company can provide.

Be ready to really have to sell yourself. Some interviewers might be skeptical of hiring freelancers, depending on the company’s work environment. You should go into every interview prepared to answer some common questions hiring managers might have about somebody who was previously self-employed.

For example, Ngoyi said an area where these individuals might be at a disadvantage is their ability to work as part of a team. In a highly collaborative environment, this can cause problems.

“Our team environment is paramount to who we are,” he said.

Be honest with yourself about what your strengths and weaknesses are and what you’re willing to work on. It’s not just about convincing the interviewer that you’re a good fit for the job – you want to be in a job that you’re comfortable and happy with.

Don’t Sell Yourself Short

Ngoyi said that he sees a lot of self-employed candidates underselling themselves as a business owner. Things like recruiting, coding, pitching and selling often don’t get represented in their résumés, he said.

“Don’t undervalue and undersell all the things you do in the day-to-day,” he said.

While you may not see some of your everyday tasks as a big deal, many of those things might be considered valuable skills depending on the roles you’re looking at.

Look at some of the tasks you regularly have to take on for your business, and think about ways those abilities could make you an asset for the jobs you’re applying to. Make sure to highlight these skills in your résumé and connect them to why they make you a good candidate.

Ask for Help

“Don’t be afraid to shoot your shot and ask for help,” Ngoyi said.

He said that while the corporate world can be a little difficult to navigate, you can always find people who are willing to help. You just have to ask.

If you’re planning on making the transition into the corporate world, he advised starting to build your network and to reach out to recruiters, leaders and team members in the industry you’re interested in.

Working for ‘the Man’

Going corporate doesn’t come without downsides. A strict 9-to-5 job can be a bummer for those who are used to a choose-your-own-schedule work structure, and many entrepreneurs who value their freedom may dislike the connotations that come with working for a bigger company.

However, getting a full-time position doesn’t necessarily mean you have to give up all your creativity and individuality in service of your company’s bottom line. Knowing what kind of work environment you’re looking for can help you find a company that aligns with your needs and values.

Plus, working for a larger company means your work has the potential to have a higher impact.

“Most folks that are small business owners go into business because they identify a problem their work can solve,” Ngoyi said. “I think being able to come to an organization like Quicken Loans that stresses innovation and creativity not only provides you more learning and experience, but also exposes you to resources you may not have had access to otherwise.”

Ngoyi said that access to resources, knowledge sharing and ability to innovate are a few benefits to making the switch to a corporate position.

Prepare for a Lifestyle Change

There’s no doubt about it; going from writing invoices in your pajamas to the 9-to-5 life is going to require some getting used to.

Strickler recommended having a game plan for the transition so it’s not so sudden or disorienting.

“You don’t want to create a seismic shift in your work or schedule so much so that it is a negative disruption. Create a 3-, 6- or 9-month strategy and get all of your ducks in a row,” he said.

Prepare for the corporate life to require different things of you that you might not be used to, like being more open to collaboration.

Ngoyi said that this can be a pitfall for those transitioning out of self-employment. When you’re your own boss, “you have this autonomy and this control, and ultimately, you’re the driver,” he said.

Start working on these skills ahead of time. Learn how to step back and let others give their input. Get used to the idea that you won’t always get to see the direct results of your work in the same way you do when it’s just you running the show.

Going from freelance to full-time can be a tricky transition at first, but remember the same skills that helped you start your own business – your courage, your perseverance, your creativity – will help you through.

Are you on the lookout for your next career move? We might have the perfect role for you! Check out our current openings at the Quicken Loans careers website.

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This Post Has 2 Comments

  1. I’m a freelancer for more than 3 years and it’s hard for me to imagine myself in the office. Working remotely has changed my life for better. Greatly that there are dozens of specialized freelancing platforms, for example, Beesy.pro – free, handy, legal.

    1. That’s awesome! This article isn’t meant as a knock on freelancing. I know a couple of people in my own life who are very happy in their businesses and have seen great success. This article is just meant to serve as a resource for people who might be thinking about a lifestyle change with the security that a corporate job offers. Thanks for sharing your perspective!

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