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Hope For the Upside, Plan for the Downside

Posted on February 22, 2023 by James Harold Webb
Hope For the Upside, Plan for the Downside

As an experienced entrepreneur, businessperson, and human being, if there is one thing I can share as a key to sound decision-making it is this: hope for the upside but always plan for the downside. If you do this and make it a priority to truly evaluate opportunities and decisions with this mindset, you’ll help yourself avoid a lot of unnecessary heartache and stress.

There are things you can’t possibly plan for. What you can plan for is risk in any given situation. In business and any relationship, there is risk involved. Whether it’s financial or emotional, risk is always at play. Some people avoid risk at all costs. They may not make it big, but they don’t lose a lot either. Other people are cavalier. They take huge swings and strike out a bunch in pursuit of that one perfect home run. Still others, people like me, approach risk from a different angle. I look at risk as a calculation. If a risk is huge and comes with a big upside, I’m suspicious but interested. And, I’ll follow that interest until the risk-to-reward relationship either becomes untenable or irresistible. I’m no adrenaline junkie, but I’m not afraid to take a shot either. I have a pretty good eye for the upside and potential downfalls. However, it took me a long time to learn how to size up an opportunity and judge whether the juice would be worth the squeeze.

That ability to judge what is worth the risk didn’t come without some difficult situations and learning experiences. Those were pivotal moments in my career and have proved some time-tested principles that are key to navigating, adjusting, and being successful:

  • Prioritize your relationships. There will be moments in your life where the approval, recommendation, or opinion of someone else will be essential to what happens to you. Live a life where others are willing to vouch for you in life’s difficult moments.
  • Accept failure as a stepping stone to success – Failure and mistakes provide the life lessons that make the greatest impact and prepare us for achieving more.
  • Know when to let go – Are you so crazy about an idea that it is blinding you to the objective likelihood of failure? Are you throwing good money after bad because of your own sunk-cost bias? Are you ignoring advice from objective sources and experts? Humility and self-examination are critical to success. You have to be willing to let go.

Just because something seems brilliant doesn’t mean that it’s worth it. Just because something seems hard doesn’t mean that it’s not worth the effort. It’s easy for me to write this now, in my nice house, at my favorite desk, and with sixty years of hindsight. And, as a concept, it seems easy enough—before you do something, calculate what you will have to put into it against what could potentially come of it. Simple, right? Perhaps. But getting good at it and practicing it requires some growing pains. However, if you prioritize the relationships you encounter, accept learning moments for what they are, and recognize the value in evolving ideas, you’ll find yourself enjoying the upside more than the opposite. Thus, when the downside comes, you’ll be prepared to more successfully navigate it.


Learn my proven approaches to spur your own growth, profitability, and success. Attain your own copy of Redneck Resilience: A Country Boy’s Journey to Prosperity, on Amazon.