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Back To the Grind After Being Your Own Boss

Don’t think of yourself as a failed entrepreneur, but as someone who’s moving to an engaging new chapter in your work life.


by Kara Baskin

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You gave it your best shot, but things just aren’t gelling. It’s time to quit your business and return to the 9-5. This is a crossroads where it’s easy to get down in the dumps. “Given all that time and energy spent talking up your business, when it comes time to announce a shift back to the corporate world, you may find yourself doubtful, needing to reconcile the change internally and then spin it to yourself and others,” says Kathy Robinson, founder of Boston-based Turning Point career coaching service.

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With the right attitude, though, your return could signify the beginning of an exciting new chapter, not the death knell of a failed entrepreneurship. Robinson explains how to frame the transition as something exciting and positive.

     See also: You Can't Change Your Career Without Risk

Realize this happens all the time, for good reasons. Many entrepreneurs constantly project to others (and themselves) that everything is great in order to build confidence and gain sales, Robinson says. But underneath that sunny façade, entrepreneurship can be exhausting: Clients don’t pay on time. Projects are inconsistent. You work long hours for less money. You can’t go on vacation without finding someone to cover for you. Health insurance is expensive. Retirement looms without a 401(k) match. And on and on. “As entrepreneurs, we don’t often admit these challenges to ourselves or talk about those downsides, except with our very inner circle of friends and family. But those downsides are real, and many entrepreneurs routinely consider or pursue ‘regular’ employment as a change of pace,” Robinson says. You’re not alone.  

See the positive side of your next gig. “As someone who’s had to manage all aspects of a business, think of what a relief it will be when someone else manages the parts you hated, like sales, accounts payable or doing taxes,” Robinson suggests. “Then think how great it will feel when you have a team alongside you to share responsibilities, plus a regular paycheck. Most of all, know that your new employer values the experience you’ve gained, and you’ll bring a bigger-picture perspective to the table than someone else who’s never run their own business.”

     See also:  Rebrand Yourself For Career Change

Share those new advantages with others. Feeling better? Now it’s time to tell your friends and family about the next step—with pride. “What’s exciting about it? If it represents a new professional learning opportunity, share your enthusiasm. Even if it doesn’t—let’s say you just need to pay the bills—it’s offering you something you didn’t have before: stability, benefits, routine, personal contact, a chance to regroup and figure out your next move,” Robinson says. Be sure to emphasize what you gleaned from your entrepreneurial days, too, whether it’s skills learned or people met along the way.

Be prepared for another 180. “Those of us in the entrepreneurial life get somewhat attached to the idea of innovation and independence, but there are many ways to be entrepreneurial inside an organization with the bonus of a steady paycheck,” Robinson notes. “On the other hand, while business owners shouldn’t rule out ever joining a firm, they shouldn’t rule out returning to entrepreneurship down the road either. The working world is so fluid that people move in and out of the corporate world on a regular basis. Maybe this job will be exactly what you need to build something new in the future, or, at the very least, give you a nest egg that you can use to pursue your interests in retirement,” she says.

     See also: Capitalize On Your Eclectic Experience

Remember, this is just another step along life’s path that will provide a foundation while you figure out your next move, whatever that may be.