The Intentional Entrepreneur
Like many of you, I’m a serial entrepreneur. But what might set us apart is that I consider five of my first six businesses failures. Despite this, I was determined to pursue my entrepreneurial dreams and learn from my mistakes. It was during this time that I found the guidance and support I needed within EO. When I joined the organization, I was in the process of selling my seventh company. I did well with the sale, and I was feeling good about my prospects as an entrepreneur. I could smell success and figured my next business would do just as well, if not better. What I didn’t expect was the collateral damage.
When I launched my current business, StringCan Interactive, I hit the US$1 million-revenue mark within 20 months. I felt like I finally had what it took to successfully scale a business. My eye was on the prize, and I was certain nothing would stand in my way. There was just one problem: As my business grew, my home life wilted. I woke up one day and realized my family was suffering from my devotion to my business. I had always valued that my wife, Rachel, was supportive of me in my business endeavors. When others told me I should get a “stable job,” she encouraged me not to throw in the towel. I was proud of our marriage and relationships with our two daughters, Lexi, 12, (pictured left at middle) and Ella, 10, (pictured left at bottom). But I was confronted with the truth: Along my journey toward professional success, my most important relationships were sacrificed. It wasn’t intentional or malicious, but it happened nonetheless. My wife and I started to feel like roommates, and we squabbled with our kids often.
When I was honest with myself, I saw the path that brought us here, one marked by late nights at the office, answering emails during family meals and a dogged pursuit of success. Something had to change. When I considered my malnourished relationships at home, I became frustrated. In business, I rarely had issues working through tough interpersonal dynamics. I always had an open dialogue with my clients and employees, and I was intentional about keeping it that way. But for some reason, I felt powerless to do the same with my family. And then it hit me: Why not take the same intentionality and processes I used to strengthen my work relationships, and apply them to my most important relationships outside of work?
The processes in my career that had always been effective were annual business planning, goal-setting, a consistent review of performance, and weekly one-on-one meetings with team members to address expectations and individual goals, as well as team building. These tenets had served me and my colleagues well over the years, and I wanted to find a way to translate them into practices that could serve me and my family.
So, I dreamed up an annual, four-day family retreat that is fun, customizable and centered around defining our purpose, staying focused, family bonding, improving communication and goal-setting. Day one lays the foundation, as the parents create a family vision. Day two includes reflecting on the past year in a visual way. Day three zeroes in on the coming year, using “dream boards” and activities to share hopes for the future. On the fourth and final day, goals are set and each family member writes a letter to their future self.
When I first invited my family to participate in this retreat with me, reactions were mixed. But they all ended up saying “yes,” and we threw ourselves into the activities I designed. The results were astonishing, to say the least. We came away from that inaugural family retreat with clear insight into one another’s insecurities, hopes and goals. It was refreshing, healing, productive and altogether rejuvenating. I can now say that after having just wrapped up our second retreat, my family has never been healthier or happier.
As entrepreneurs, we have an interdependent relationship between our home lives and our businesses. If the only thing you’re intentional about nurturing is your company, your business’s growth will be limited. But if you’re just as intentional—if not even more intentional—about working through family issues and growing in your home relationships, your business’s potential will be limitless. After all, someone floundering in his or her most sacred relationships will lack the energy and peace of mind to effectively run a business. But if that same person feels secure and content in his or her marriage and/or relationships with his or her children, he or she is free to thrive in all areas of his or her life (like in business).
And that’s really what this all boils down to. Success will only take you so far alone. But success can only be stoked—and enjoyed—when you have a strong family by your side, savoring it with you. How badly do you want to improve your family? Are you committed to creating a more meaningful life for you, your spouse and your children? The first step is to take a hard look at yourself in the mirror and consider how much your family means to you. Drastic changes are possible, and intentionality might be all you need to make things better.
Jay Feitlinger is an EO Accelerator graduate and EO Arizona member, as well as the founder and CEO of StringCan Interactive, a digital marketing agency. Jay recently published his first book, “FAMILY 2.0: Harness Business Principles to Reboot Your Family in 4 Days.” Contact Jay at