How to Know When It's Time to Sell, Quit or Restructure Your Business

Just because your business feels more like a burden than a dream doesn't mean you failed. It may just mean you're ready for your next act.
April 02, 2014

Back in 2003, I took a huge leap of faith and quit my Silicon Valley sales job to open a 2,800-square-foot bookstore in Sacramento, California. About six weeks after opening the store, I looked around and thought, “Holy crap. What have I done?” I had underestimated just about everything involved with managing that kind of business: the hassles of managing staff, the challenges of dealing with the public every day, and so much more. But I had walked away from a six-figure career, signed a three-year lease, and thrown all of my eggs into one big basket. I had no choice but to figure out how to make it work.

Throughout that first year, I worked hard to build the business. I learned how to implement Internet marketing strategies, how to generate publicity and how to host events in the store. By the end of the year we were profitable, and I was able to put a staff in place to run the store while I pursued a whole new career as an author, speaker and consultant.

Ready for Act 2

By year three, my author career was thriving and I no longer wanted the burden of owning the store, so I sold it to one of the employees. I could have viewed the whole thing as a mistake, but the reality is that owning a retail store in a strip mall with lousy street visibility forced me to learn a tremendous amount about marketing and operating a business. Today I view that store as a stepping stone that led me down the path I was meant to follow.

Not long after the sale, I launched a custom-publishing company, and over the years we’ve added many services to the menu. Recently, however, I began to re-prioritize my life, and realized it was time to simplify. My plate was too full and it was draining my energy, so I made the decision to sell off part of my business.

The result? It’s been liberating. This transition has allowed me to shift back into creative mode—the place where I am most content. And though I’ve closed off a major revenue stream, I am quite confident I will find others to take its place.

Do You Need a Vacation or Something More?

Burnout happens to all of us at some point, and it could simply be a sign that you need a vacation. Take a week or two off and see what happens when you return. If your gut is still churning all day at work, or if you toss and turn on Sunday night because Monday is approaching, that's a sign something is off. It's time to ask yourself some important questions:

  • Am I passionate about this work?
  • Is the business growing, flat or declining?
  • Have I personally outgrown this business?
  • Is there something else I’d rather be doing?
  • Am I working more than 40 hours per week?
  • Has the struggle to succeed worn me out?
  • Is my business model flawed in some way?
  • Would it help if I made some changes, like implementing more marketing strategies, hiring help or increasing prices?
  • Can I afford to make the needed changes to my business? If not, then what is wrong with my business model?
  • Am I satisfied with my work/life balance?
  • What would my ideal workday look like?
  • What would I do with my career if money were no object? (Imagine you just won a small lottery—not enough to retire, but enough to make some choices. Seriously. Give this some thought.)

Taking the Next Steps

By asking yourself these important questions, you'll begin to determine your next steps. Perhaps you are running yourself into the ground, but you’re afraid to hire help because you think nobody can do it as well as you. (Something you need to get over, right now!) Maybe you simply need to take more time off, find more balance. (Try taking Fridays off; it’s liberating.) Or you may realize that your passion has shifted and there is something else you would rather do with your life.

Fear can also enter the equation when you start asking yourself these big questions. Your business is likely your livelihood and the thought of making significant changes can be scary. How will you pay your bills if you sell, quit or restructure your business? Spend some time finding the answers. For example, if there is a part of your business that you want to let go, is there another part of your business that you can grow to make up for the lost revenue? Or is there a new revenue stream that you can build in its place?

Write Your Own Story

One of the joys of entrepreneurship is that you get to write your own story. That means you can build multiple revenue streams around your passions. You could be a photographer who also sells used toys on eBay. You could be a personal chef who also does freelance graphic design. You could be a website designer who runs profitable soccer clinics for kids on the weekends.

Of course you don’t want to make any hasty decisions, but you probably have more options than you realize. With my bookstore, I knew early on it wouldn’t be a lifelong career for me. So I put in the work to make it profitable enough that I could free up my time to pursue my next career goal simultaneously. Eventually my second career was more profitable than the store and the timing was right to sell it and move on.

Your big leap of faith may not happen overnight, but you can start planning your next move now. And you may just find the process of planning to give you the lift you need. Seeing the light at the end of the tunnel can help propel you forward, ease some of the stress you’re carrying around, and take you down the path that you are meant to travel.

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