Life Lessons From a Very Messy Middle.

August 21, 2021

Life Lessons From a Very Messy Middle.

May 29, 2023

It’s difficult to know when a "messy middle" begins and ends – and hard to know exactly what to do, how to do it, and how to move toward a new beginning. It is not only intellectually and physically challenging, but emotionally draining because of all that uncertainty.

I know this firsthand, from my own extremely messy middle. In my 40s I realized that my 50s were going to be tough: our parents would decline, our kids would leave home, we’d likely sell our house, and I was probably going to sell my business. Sure enough, all this came to pass in a titanically messy middle: for five long years, my wife and I struggled with losing our three remaining parents, our kids moving out, the sale of my business, and selling our suburban house of 24 years to start a new life in the countryside.

This was the most difficult period of my life, and in its darkest heart I was not sure I would survive. I was working constantly; my anxiety was astronomical; I began to drink; my weight ballooned; and I spiraled into depression. I needed help.

Fortunately, I had my wonderful wife, great kids, dear friends, and a tight-knit group of fellow entrepreneurs who were my lifeline. They helped me with a plan to climb out of the hole I had fallen into, and a vision for what was next. I engaged two therapists and a psychiatrist to help me deal with the worst of my anxiety and depression, and during that painful time, I learned some of the basic principles of living a joyful, balanced life that I adhere to today and which became the core of my "Five Freedoms:"

  • Mental Freedom: freedom from worry, self-criticism, and a host of other negative thoughts that bedevil most of us, most of the time. The Stoics taught that one of the few things under our control is what we think, and once I realized that I could take charge of what I told myself and how I reacted, my anxiety began to ebb and my depression to lift. I added meditation, daily gratitudes, and other tools to keep myself on track after the crisis, and I continue to work on my mental freedom daily.
  • Physical Freedom: freedom of health. No matter our current physical infirmities or disabilities, each of us can strive to be as physically healthy as possible; proper diet, sleep, and exercise not only allow us to enjoy life more but make us happier (the ancient Romans called this “a sound mind in a sound body”). Once I reached a better place mentally, I dialed in diet and exercise, lost the weight I had gained, and even started doing triathlons.
  • Spiritual Freedom: the freedom to define the meaning of your life, to connect with something bigger than yourself, and to decide how you want to contribute. It can involve belief in a deity, but it need not: you have the freedom to decide. For me, spiritual freedom is in part about creating value through the power of music, philosophy, writing, and entrepreneurship.
  • Social Freedom: the freedom to surround yourself with the people you want in your life, those who will help you achieve your goals, and who will support you in a loving and positive way. If you’ve honed your mental, physical, and spiritual freedoms, it becomes easier to surround yourself with people who share your values - and easier to remove people who are negative, difficult, or harmful. By involving my family, friends, and entrepreneurial community in my struggles, I was able to grow and strengthen deep, positive relationships with people I love, and let negative ones go.
  • Financial Freedom: having the financial resources to allow you to do work that is meaningful to you and brings value and joy to yourself and others, instead of having to work just for money. We are each free to determine what this means for us, but it always involves saving more than you spend, investing to build assets that generate income, and achieving a “cross-over point” where that passive income can support most of your financial needs without full-time paid employment. For me, this means a modest lifestyle full of simpler pleasures that don’t cost a lot (like bicycling, hiking, singing, playing piano, writing, consulting, and traveling), and being grateful every day for the resources I have rather than striving to get more than I need.


These Five Freedoms continue to be my focus, helping me stay on track for a happier, healthier life with the freedom to be who I really want to be for my family, friends, and communities. I share what I’m learning in my blog (https://www.declaringfreedom.com), and you can always reach me at tony@declaringfreedom.com.

MEA alum Tony Coretto is an entrepreneur and investor who lives near Woodstock, NY with his wife and two cats; he’s an enthusiastic adventurer who enjoys singing, playing piano, writing, philosophy, bicycling, motorcycling, world travel, and the occasional dry vodka martini.

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