We are obsessed with winning. We want to win the race and be the best. But in life, we are destined to lose. We do not win at all, or we win infrequently; we get sick, we age, and we die. Life is a struggle, and loss is inevitable. Even the gifted are surpassed by those more gifted. Over time, the “best-ever” experience lesser levels of performance.
Using perception and intelligence to discern reality, while essential for good decisions, can cause us to become depressed and passive. If we are paying attention to the realities of life, it is difficult to remain in a state of happiness. To deal well with life, we must deal with losing, not winning. While winning may bring short-term happiness, for many, happiness and winning do not happen. Happiness is an attitude based on rejection of a significant portion of reality and is not conducive to making good decisions. The way to deal with losing is to use perception and intelligence to discern reality and act on it with good decisions, rather than retreat from it.
In sports, no one wins all the time – yet popular focus is on how to win and the short-term pleasure that brings. But, if you examine what has made someone exceptional in sports, it is not reacting to winning but how that person has reacted to loss. This is a metaphor for other aspects of life, where the measure of worth and satisfaction comes not from savoring victory, but, given the inevitability of losing, from how to deal with loss. Those who win after losing are praised, and rightly so, but they will soon lose again.
Think about what happens when we lose. We often ask the question: “Did I do the best that I could?” The answer can reassure us or cause grief and guilt that never leave us. Our actions may not cause a win, but knowing there was a best effort brings a sense of worth and satisfaction that can sustain a life.
It is not always a zero-sum game. In business, as in most aspects of life, there are levels of accomplishment. While you may not have a billion-dollar exit, you might still create a business and sell it for maximum value, making your family financially independent.
If you spend your time lying on a couch and watching television, you will have a difficult time convincing anyone, including yourself, that you did all you could concerning your life condition. On the other hand, if you begin an endeavor, such as starting a business, work to make it profitable, and try to derive the maximum value from that business for you and your family, you could justly feel that you did the best that you could. The stress and effort may not have made you happy. The business might fail. You may have made mistakes, but you made the effort and did the best you could. That realization can bring a sense of worth and satisfaction that can sustain a life. I am not going to equate happiness with satisfaction from doing the best you can do, but I will say that the satisfaction that comes from doing the best you can is life-sustaining.
The way to think about and accomplish all you can do is through planning. Planning is thinking and decision-making. It does not require diaries or journals. It is a mental discipline you can learn and apply reflexively.
Most people do not plan, and few know how to do it well. A planning discipline will make you a serious person – one who thinks about life and acts upon those thoughts. That discipline will help you deal with the damning or life-sustaining question: “Did I do all I could have done?”
Business success is about learning how to make decisions and document those decisions in a plan. This is a planning discipline, which can be personal and embedded in a business. Success comes with planning, learning what goes wrong, revising the plan based on the experience, and continuing toward the goal. The question is not whether you lose, but the highest level that can be achieved.
To learn this discipline, you must first learn to use group decision-making. Making decisions alone will not yield consistently good decisions. Then, using group decision-making, you utilize the planning process. The planning process is making decisions about setting reasonable goals, documenting those decisions in a written plan, taking action to meet those goals, measuring the effectiveness of that action, and revising the goals or actions as appropriate. The discipline is to use a process for thinking, decision-making, and acting that becomes habitual. This discipline can avoid emotional and reactionary decisions that inevitably cause us to feel grief and guilt. As with most disciplines, it is difficult to learn but easy to use once it is mastered. What will make a difference in your life is to make the planning discipline habitual not only in your business but in your personal life.
Most business decisions are made once and never looked at again. The Dynamic Planning Project is a guided process for installing a format that documents your decisions, communicates the goals behind them, monitors the results, and revises the plan until the discipline becomes a habit. Learn more about the Dynamic Planning Project.
Owning a Business is a Substack newsletter written by Rick Riebesell about owning, buying, selling, and advising a small to middle-market business. Free subscribers receive all new posts and the email course Embed a Quality Decision-Making Process. Paid subscribers receive the entire archive and the courses on Prior Diligence, Dynamic Planning, and Implementing the Succession Plan with Buy-Sell Provisions.

