Moving From Self-Employed to Corporate Can Be A Leap Forward, Not A Step Back
By: Cathy Goodwin
Tags: Life Lessons, Life, Entrepreneurship, Careers, Business

Photo by Cam Adams on Unsplash

You’ve had your own business for the last 5 years. Your biggest customer is going away. You’re getting tired of chasing down clients and dealing with people who don’t value what you offer. Maybe your family clamors for a “real” job with benefits.

Can you survive in a cubicle after tasting the joys of flying solo?

Many entrepreneurs feel sad when they make this move. Sometimes they wonder, “Am I a failure?” Or they simply miss being able to make the kinds of choices available only to entrepreneurs and the identity that goes with saying, “I’m a business owner.”

Others — probably the majority — are deeply relieved. Entrepreneurs tend to embrace change and many see this move as the path to yet another adventure.

Having your own business makes you a better player in the corporate game.

Many former business owners find they’re in better shape to deal with corporate BS than they were before. They’ve gained perspective. They know they’ve got options: if you’ve built up a business once, you can do it again.

Still, you can experience some challenges on the road back to the cubicle. For example:

(1) If it’s been a while since you did the job search thing, your resume may need a makeover.

Pick up a handful of books from the bookstore. Draft your resume. Get feedback from executives in the field and/or company you are trying to enter.

If you get inconsistent feedback, or mostly negative feedback, seek help from a professional consultant. Getting on a payroll faster means your fees will be repaid many times over.

Avoid any service that promises to get you a job or get you “in front of” managers who can hire you. Only a recruiter can do that. Stay away from the companies that promise to “blast” your resume to a few hundred prospective employers.

(2) Practice spinning your story of why you’re ready to return to corporate life.

Tell the truth with a positive angle. Your future employer will be concerned that you’ll return to self-employment after you’ve paid a few bills and saved some money. Your goal is to ease their fears.

The best way to convince them you’re serious is to research the company. Show that you’re excited by the possibilities of working for them in very specific ways.

(3) Enjoy your honeymoon period once you get on a payroll.

For the first 6–12 months, back-to-corporate workers tend to have fun. It’s like playing a new game.

You’ll find yourself snickering at the games people play…long unnecessary meetings, contributions to birthday gifts, and writing “reports” that nobody reads.

You’ll also enjoy getting things free that you used to pay for. No more dealing with the computer repair guy. Just call tech support.

(4) Expect to be amazingly productive in your new job.

Working on your own has given you perspective. You guard your time more carefully. You ask, “Do I really need to do this?” You’ve learned to figure things out yourself before you ask for help.

(5) Plan for a return to self-employment, even if you’re happy.

Once you’ve been on your own, you probably caught the bug. Even if you don’t miss being on your own, you have to remember that corporate jobs can change or disappear without warning. It’s like losing your biggest customer with no plan in place to replace the income.

Everyone should have a side hustle, starting around age 35 or 40. As you get older, you face age discrimination in your own company, as well as when you seek another job.

A side hustle is the closest thing you’ll have to job insurance. You’ll be more confident on the job and often perform even better because you don’t go into panic mode over rumors of change. You know you and your family will do just fine.

Now you have time to plan your next move in a leisurely fashion. Take classes. Visit the Small Business Administration. Attend networking events featuring business owners.

But be very, very discreet. Your company wants to believe you’re committed to staying forever, even though they rarely reciprocate.

Corporate to Entrepreneurship Can Be A Round-Trip

Finally, keep in mind that the journey between corporate life and entrepreneurship is very much a two-way street. These days, people go back and forth. I know many people who found themselves happy to be back on a W-2 schedule … and many who loved their corporate world but were really glad they had a side hustle too.

Learn more about side hustles from a good book by Chris Guillebeau and a set of interviews I conducted with people who turned their side hustles into full-time careers.