Transitioning from Freelance Success to Corporate: Navigating the Why, How, and What’s Next

The conversation about freelance work vs. corporate(i.e., in-house employee) life is typically the pros and cons of leaving your current job in pursuit of a freelance career. But let’s look at this from the opposite perspective – what if you are a successful, financially secure, free-lance sole proprietor but you want to return to the corporate fold?

The first question your friends, family, and, especially, potential employers will ask is, “Why?” Why… would you want to work for somebody else when you’ve been your own boss? Why… would you go from pocketing the profits to drawing a paycheck? Why… would you go from making your own schedule to clocking in? Why… deal with office politics – now more than ever? Why… choose to be subject to the whims of corporate restructuring, buyouts, mergers, downsizing, etc., instead of the master of your fate?

Control the Narrative

You are most likely to be met with skepticism, and the top misconception will be that your turn at a freelance career failed so you must “get a real job.” From the onset, you must overcome the perception of failure and the only way to do that is to control the narrative. Let’s say the perception is reality. Working free-lance you couldn’t make ends meet and so you had to jump ship. You still need to control the narrative and the best course of action is always the truth.

The truth is that to launch, succeed, and sustain a freelance career based on whatever magical special skill you possess isn’t enough. You must also be an entrepreneur who can run a small business, which is what a sole proprietor is. Let’s say your special skill is turning water into wine (digression: please DM contact info if this is a skill you possess). That’s not enough. There is a lot of work beyond your superpower. You must also be a CEO, COO, and CIO rolled into one, a salesperson, an accountant, a marketing guru, a tax expert, (just to name a few), or be able to afford people to do all that for you.

Not everybody has the financial acumen or business skills to do all the other things being a free-lance worker require. Sure, you’re your own boss, but you work alone. Sure, you pocket the profits – after operational expenses, taxes, licenses, etc. Sure, you make your own schedule, but the flexibility can be chaos. Sure, it’s great to be master of your fate – until it isn’t. Life circumstances change and sometimes changes are needed.

If you want to be a full-time employee again, employers are going to have reservations about your assimilation into a corporate hierarchy and working with others. You must demonstrate you have a genuine desire to return to the corporate world and aren’t buying time until you can go out on your own again. No company wants to be a stepping stone. Remember your narrative! You want to work with others toward set and achievable goals with measurable results and increase your skill set through collaboration. You want to spend time doing what you’re passionate about, not spending late nights on QuickBooks.

Back-Up Your Narrative with Your Resume

Your resume should be as close to a written record of your narrative as possible.  If you free-lanced for a year during COVID or during a bout of long-term unemployment, you can gloss over it without raising eyebrows. If you’ve been hustling for over a decade you must own your achievements and find a way to condense what you’ve done to advance your narrative explaining your motives for this major transition.

Your resume will be a prelude to an interview so it is in your best interests to lay the foundation of your narrative. There are many commonalities between your resume and how you present yourself in a job interview. You want to show a history of success but highlight jobs that were collaborative, in the company’s field to which you are applying (if possible), and demonstrate long-term commitments with results that exceeded expectations.

For example, let’s say you worked for six months at a prestigious company in the same field at your targeted potential employer. Recruiters and hiring managers are going to want to know the quality of those six months. Were you (for example) a freelance marketer or an outsourced consultant chief marketing officer/director? The former is a temporary task-oriented assignment. The latter is embedded in a company and directs important strategic projects. How you present it is important.

Spend the time tinkering with your resume until it tells a consistent story about your freelance work history with a focus on jobs that most mimic a corporate environment. You are the only person responsible for your first impression. Do the work. Look spectacular.

Compensation

Show me the money! Another misconception about working freelance is that you’re rolling in money. Maybe you are. Good for you! More on that below. But most freelance workers are like any other small business – you pay for everything else before you make any money and the margins can be slim. Operations, taxes, insurance, gaps in employment, etc., take their toll on your bottom line. Working for a company means stability and predictability and all that extra work running the business will be done by other people.

If you want to get an idea of how a freelance-to-corporate transition will affect your finances start with payscale.com and go from there. For example, let’s say the average salary for your specialty is $75,000 a year in your region. That’s an average, so where you do believe you will fall in the range? Higher? Lower? Why? Be prepared to make your argument. Is it more or less than your freelance business? How about the benefits (e.g., health insurance) you’ve been paying out of pocket?

Do an assessment of all the liabilities and assets and determine whether the move will most likely be a PACKAGE (not just take-home pay) increase or a decrease. This requires a deep dive into the numbers to know how your financial situation will change. Do all calculations before you do an interview! If you’re a super successful freelancer you may have room to negotiate
a larger package because you are leaving money on the table. However, the battle to prove you can work in a corporate environment may be more difficult. There’s always a trade-off!

Bonus Tip: Don’t announce the dissolution of your freelance business until you start your new job and the check clears. You never know what’s going to happen.

Philip Roufail contributed to this article.

Scott Singer is the President and Founder of Insider Career Strategies Resume Writing & Career Coaching, a firm dedicated to guiding job seekers and companies through the job search and hiring process. Insider Career Strategies provides resume writing, LinkedIn profile development, career coaching services, and outplacement services. You can email Scott Singer at scott.singer@insidercs.com, or via the website, www.insidercs.com.