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Lessons From A Middle-Aged Entrepreneur

As seen on Forbes.com

Three Gems For The Next Generation

What is your biggest regret in life?

When you ask our seniors this question, you often get a surprising answer. Karl Pillemer, Ph.D., is the keeper of The Legacy Project at Cornell University. When Dr. Pillemer asked 1,200+ elders this question, they often answered, “I wish I hadn’t spent so much of my life worrying.” They lamented that their anxiety had kept them from enjoying life’s precious moments and had rarely impacted the future since most of the things they were worrying about never happened.

Sounds like valuable wisdom to me. Perhaps I should have paid attention to my childhood idol Alfred E. Neuman.

This sage advice from our seniors got me thinking about what a middle-aged entrepreneur of 50+ might be able to teach the younger members of our courageous tribe. So I asked some of the entrepreneurs I respect most the one piece of advice they would pass on to their child if he or she became an entrepreneur.

Here are three of my favorite answers:

1. Share The Journey

Coach John Wooden famously said, “Show me your friends and I’ll show you your future.” Nearly every one of my friends shared an impactful story about precious advice they received from a peer during a particularly challenging time. These friends all belonged to groups like Young Presidents’ Organization, Young Entrepreneurs’ Organization or Vistage, through which they developed deep friendships and meaningful connections with peers. They have all become dependent on these networks for wisdom, encouragement and ideas.

If you want to be successful, surround yourself with other entrepreneurs who have the humility to share mistakes. Peer groups are a great place to start.

UCLA basketball head coach John Wooden, "UCLA: Southern Campus: 1960." By Associated Students, University of California, Los Angeles [Public domain], via Wikimedia Commons

UCLA basketball head coach John Wooden, “UCLA: Southern Campus: 1960.” By Associated Students, University of California, Los Angeles [Public domain], via Wikimedia Commons

2. Forget About Balance

Let’s face it; entrepreneurs are anything but balanced. They work too hard, play too hard, arguably take too many risks, and break more rules than most people you’ll meet. So suggesting balance to an entrepreneur is like asking Donald Trump not to speak about himself in the third person. Instead, the most successful entrepreneurs set audacious goals that involve more than just growing their businesses. Their goals extend to include things like work, family and play; five family vacations a year; four triathlons; and double-digit growth. Why not? Sounds like good goals to me.

Most of my entrepreneurial friends have a list that includes exercise goals, relationship goals, travel goals and, of course, business goals. For each of these, they measure their progress monthly and often have an accountability partner to keep them honest and on track.

An aggressive goal strategy that includes all areas of your life will allow you to get more done. Ironically, you’ll also wind up looking like you are leading a balanced life. But don’t worry—your buddies will know you’re still just a crazy entrepreneur.

3. Support A Cause

Eventually, most entrepreneurs desire to move from success to significance; they begin to worry more about legacy than profits and losses.

If you’re reading this, chances are you are one of the rare people who know how to start things. Fortunately, there are people like you who have already started causes that make the world better—they feed the hungry; they save the rain forest; they fight cancer; they do good things. There is virtually a cause for everyone, and contributing to these causes often becomes the most meaningful part of an entrepreneur’s life and legacy. As an entrepreneur, you may provide a much-needed spark to a cause that will impact lives for generations.

My friends offered all kinds of good advice that was based on their experiences—some good and many of them bad.

Wisdom is priceless. I like to say that experience is learning from your own mistakes, but wisdom is learning from the mistakes of others. Experience is often painful and leaves bruises. Wisdom is a gift, given generously from humble people who are willing to share their mistakes. I am grateful for the gift of wisdom from my entrepreneurial friends.

Follow me on Twitter @theideamonkey or read my Forbes blog here.

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