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My Biggest Life Lessons

Posted on September 28, 2022 by James Harold Webb
My Biggest Life Lessons

Some of the biggest life lessons I’ve learned have come as a result of significant experiences I’ve had navigating my career. The lessons learned in business and life, in fact, mirror each other. Why wouldn’t they? Business has been and continues to be a major part of my life, not something distinct from it.

Every relationship, every endeavor, every aspiration and dream, success, and failure—they are all part of your life. Trying to draw a line between the experiences that make you money and the experiences that give you purpose seems to miss the point. I guess that’s why the life lessons I have learned share so many of the themes I learned about business. They all concern focus and relationships, humanity, and recognizing that you need as much help as you can give to others. Consider the lessons you’ve learned in your personal and professional life thus far. Here are some of mine:

  • Contribute, Don’t Just Take – You don’t have to be rich to give. But connecting the things you get from working with the opportunity to give back early and often is where purpose evolves. It doesn’t have to be money. It can be time, effort, or taking a call from someone who just needs to talk. Bring the same focus and dedication to the world outside your profession that you do inside. Also, don’t wait for success before you start giving. Start giving and let what you learn from that experience be the cause of your success.
  • Seek Specific Education – The days of having a general degree are over. Whether it’s a degree in accounting or a certificate from a trade school, learn specific skills and study specific, practical topics. In a world where a bachelor’s degree is almost meaningless, it has become clear that the people who opt to develop specific knowledge have an advantage. I would rather hire, work with, and invest in people who will do what it takes to be an expert than those who take the path of least resistance. The education you seek reflects your approach to life. The quest for knowledge should extend far beyond your coursework.
  • Live In the Moment – If today and only for today you go home and kiss your significant other a little longer, hug your kids a little harder, tell your friends you love them, and go out of your way a little more to help someone, it is a day well lived. You are guaranteed nothing but the exact moment you are in. You must take the time to appreciate the moment. Work hard, love hard. Take the time to think about the gift of living while you work on building your life. That’s what makes it all worth it in the end.
  • Ask, “Why Not?” Instead of “Why?” – “Why can’t my family be the next Rockefellers?” Perhaps some may think this is an unreasonable thought, especially coming from a poor kid from Mississippi. But reasonable has never been a trait to which I have aspired. Don’t be reasonable. Don’t settle. If you allow fear, comfort, easy stability, and ego get in the way, you’ll find yourself merely settling and not achieving all that you really could. Be pragmatic enough to recognize reality but unreasonable enough to think you can change it. In other words, in all things, ask yourself “Why not?” instead of “Why?”

I’m grateful for the experiences I’ve encountered, for the relationships I’ve engaged in, and for the opportunities that have come my way. Some of these have been incredible successes and others disastrous failures. They all, however, contribute to the person I am today. They teach me invaluable lessons that I wouldn’t trade for anything.


In my book, Redneck Resilience: A Country Boy’s Journey to Prosperity, I share a number of fundamental principles that helped me triumph personally and professionally. Learn from my personal experiences and leverage my proven approaches to spur your own growth, profitability, and success. Get your copy today!