Jim Donnelly is the cofounder of Restore Hyper Wellness, which delivers an extensive array of cutting-edge health modalities.
It has always made sense to me to think of life in five-year cycles. We go to high school, college and then enter into the early portion of our careers. If we’re lucky, we meet and court a counterpart and live a few years in kid-free bliss. Then comes babies and the trials and triumphs of early parenthood. And on and on. Not every life takes the same shape, but once you start looking around, the five-year rule applies more often than not.
What I hadn’t realized early in my career was how my entrepreneurial journey, my business and my personal life would intertwine, functioning together in synchronized five-year cycles. In 2000, I cofounded an online travel community; by 2005, I sold the company and moved on. I spent the next five years creating boutique, luxury businesses in my hometown of Charlotte, ranging from condo development projects to a men’s grooming lounge. Next, I created an engaging online environment for families, running it from 2010 to 2015. Then came my most recent project in wellness.
Thinking of my life in fives has served me well. Here’s how I think about this simple construct and how entrepreneurs can leverage it to get the most out of their own careers.
Find The Right Opportunity For The Right Time
If we keep our eyes open, sometimes the right entrepreneurial opportunities are simply a product of our phase of life. I founded my online travel community after my military career made me an experienced and passionate traveler. When my kids started preschool, I began to think about ways to make communication between students, parents, coaches and teachers more seamless and secure. I spent five years on an online environment for families to do just that.
New problems pop up during every stage of life. Many of them are solvable. And when the challenge impacts you personally, you might just have the right mix of knowledge, approach and motivation to attack with vigor—and make something great.
The Challenges Of Starting Over
Of course, starting over every five years is not for the faint of heart. When you change industries, you intrinsically lose some of the expertise and advantage you’d spent the last five years building up. Meanwhile, you will almost certainly have more to lose. If you’ve built a good life for yourself already, have a family to provide for and have established a level of structure and rhythm in your life, starting fresh can be disruptive.
Inevitably, at some point, doubt will creep in. Should you really be making such a dynamic, mid-career change? Are you ready to swallow the risk? Those questions are for each entrepreneur to decipher.
But I would argue that despite the risk and momentary step back, a directional shift is often well worth it. You’ll take your business experience with you and, once you’ve thoroughly examined your new industry, may even have the fresh perspective to disrupt it.
When It’s Time To Move On
Companies go through cycles, just like people. They require different skill sets at various stages of maturity. That means the person who founded it might not be the best person to lead it into the future.
I’ve discovered that for most of my ventures, five years has been the right time for me professionally as well as for the company to seek a new direction. And when it comes to moving on from a venture that just isn’t gaining traction, a five-year approach can save you from a stubborn commitment to an idea that simply doesn’t work.
Of course, with my latest venture, I broke my rule, sticking around a full eight years as we established a national brand. I knew I wasn’t the right person to grow it further, and I sensed that my partners did, too. When I found myself constantly checking my watch during the sort of meetings that used to energize me, I decided it was time to go.
All Things In Context
As entrepreneurs, it’s most important of all that we tap into our authentic selves. That’s where we make magic and grow thriving businesses. If the five-year plan doesn’t make you tick, or if it doesn’t fit your specific aspirations, above all else, you should find a construct that does.
But I do recommend having a working hypothesis for your own entrepreneurial success. It will allow you to look back, evaluate and amend. Ultimately, it will help you create a career that matches—and enlivens—your life.
After five years, sometimes I’ve decided to sell, other times I’ve stepped aside and allowed the talented folks I hired to take things over. Either way, I’ve met the ensuing years with renewed enthusiasm. I know I won’t be doing the same thing 20 years from now, and that’s all the more reason to focus on making an impact today.
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