Q: I opened my retail store in 1989 when my second daughter, Emily, was a year old. She turns 21 on December 28, as I celebrate my business's 20th anniversary. Ups and downs to be sure, an extremely supportive spouse along the entire journey. I find myself struggling through menopause. Depression, second-guessing myself, unwilling to take risks, becoming a hermit—all not in my usual character. I'm trying to find the passion and creativity I need to survive, prosper and continue my life. It's extremely stressful owning/running your own business. Lately, I think it's taken a toll on me. I could sleep a week straight. 

I could sell my commercial property/business. But then, what would I do? What can I do so I live my best life? I look at life pretty much as black-and-white with a little gray thrown in. I need options and someone to help me figure it out. I know I can with guidance. 

  — Debra, age 54 

A: Debra, first take time to really appreciate your own accomplishment. You have raised a daughter to adulthood, your business is marking its 20th anniversary, and you have a wonderful spouse to share everything with. These are no small feats. Be proud of them. 

You say that you look at life as "pretty much black-and-white," and allow me to say that you've shared an example of your tendency. You're looking at your business and the enormous effort involved in keeping at going, and you ask, "Should I sell?" But the first question I would ask you in return is this: Is it necessary to sell your business to find your best life? Or is there a middle, "gray" ground that would allow you to keep the business you've built but find some help in relieving some of the stress you feel? 

So many business owners feel the need to take on every task personally, to make sure that every detail is just right. And your business may require you to do that. But what if it doesn't? Take the time to break down how you feel about all the tasks you do every day, week and month. You may find that 25 percent of the tasks are causing you 90 percent of your stress. What if you could hire someone to take on that 25 percent? Would that make the business feel more worthwhile and allow you to focus on the strengths that helped you build it in the first place? If the answer is no, you simply can't find someone to help with the tasks that keep you up at night, or you can't separate the stress of the business from simply owning it, then maybe your answer is black-and-white, and it's time to sell. In that case, you seem to be in a good position to move on to the next phase of your life. Use the self-knowledge you've gained from deeply examining the tasks you currently do to guide you toward your next challenge. Focus on those tasks that made you feel most intrigued, most invigorated, most alive. Then figure out what job—whether it’s a new business you start, volunteer work or working for someone else—will help you to do more of what you love.   

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