Why Real Wisdom Never Leads to a Boring Life

When I was in high school, I was regularly praised by teachers and other adults for making “wise” decisions. This wasn’t because I thought through my decisions well or considered options that other people didn’t think about. It was because I avoided doing all the “bad” stuff. I was considered wise because I didn’t drink, go to parties, or hang out with the “wrong crowd.” It was ironic that adults considered me wise; the only reason I didn’t do those things was because I was heavily addicted to video games. In retrospect, this was far worse off for my personal development than making many of those mistakes would have been!

Aside from avoiding fun-yet-slightly-bad things in life, I’ve always thought that being wise meant:

  • Acting really slow
  • Planning more
  • Asking advice from as many people as possible
  • Being risk averse
  • Overall being afraid to act

My views began to change when I started to hang around a guy named David. While David and I are very close now, when we met he was quite a dilemma. David was always taking risks. Even though he was in his early 20s, working, and going to college, he decided to get into real-estate investing and bought his first rental property. Virtually everyone around him doubted him and were skeptical that he could be a landlord at such a young age. (Now three  years later, David owns two rental properties and his success has directly influenced many other people to get into the same business, including myself.) 

David challenged my conventional ideas about wisdom. In contrast to what I had always thought, here’s what David suggested:

#1) Take a lot more risks than you do now.

I equated not making choices with wisdom. I thought that when you took action and actually did something, you were taking a risk, and wisdom says to avoid risk. David, however, landed on the other side of things. David said that, like anything, the more action you take, the better you get at it. Making decisions and taking risks gets easier with practice. (I would later find out that taking action makings things easier, cheaper, and more successful.)

#2) Act first and plan second.

David always cautioned me against planning too much. He knew I used planning as a way to procrastinate and avoid taking action. Taking action often pushes me out of my comfort zone and this makes me afraid. Unfortunately, most of the good stuff in life lays outside the comfort zone (link). While many things we do require at least a little planning, David advised acting first and then figuring it out as you go. (I found out later that being naive is a great help to this! [1] [2]) 

#3) Don’t ask so many people for advice.

I had always thought that the more people you ask for advice, the better off you’d be. David didn’t think so. He said that he has mentors in his life – all of whom were experts in different areas. If he needs advice on a rental property, he talks to his friend Joe who owns a lot of rental properties. If he needs spiritual advice, he goes to his parents, who are pastors. He typically only asks for advice from people who are experts in that specific area.

This made a lot of sense to me as whenever I would ask for advice, I would constantly get confused. Whenever I asked for advice, people would routinely tell me all the stuff that could go wrong – the mistakes that they had seen their friends and family make and how I was in for a lot of pain and trouble. This would always leave me discouraged. 

The more I’ve learned about successful people, however, the more I’ve noticed an important trend: they all took risks. In fact, they saw risk-taking as a component of success. They didn’t think that the goal in life was to make as many perfect choices as possible. Their goal was just to succeed a lot more than they failed. And even when they did fail, they didn’t call it failure, they called it “learning.”

Famous philosopher Friedrich Nietzsche wrote:

“A thinker sees his own actions as experiments and questions – as attempts to find out something.”

And nationally known speaker and consultant Denis Waitley says:

“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end. Failure is something we can avoid only by saying nothing, doing nothing, and being nothing.”

I’ve learned a lot since I met David. While I still often procrastinate and over-plan, I do less of it now. I’ve also realized that a lot of reasons I didn’t want to do things boiled down to fear. I saw risk-taking as something that made me vulnerable, and that scared me. But now I press into my fear. If something makes me afraid, I use that as an indicator that I should do it!

What risks are you avoiding because you’re afraid?

What would your life look like if you put aside your fear and simply took a risk?


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