in Entrepreneur

7 Stoic Principles Every Entrepreneur Must Embrace

Philosophy’s absence from the business world is a crucial mistake.

By and large ignored by popular culture and forgotten by the media, modern philosophy has been delegated strictly to the classrooms by its own doing. Rather than adapting to the times, modern philosophers have retreated into an ivory tower of abstract intellectualism and esoteric gloating.

Come on guys, you’re giving philosophy a bad name!

For those of us who live in the real world, there happens to be one branch of philosophy created just for us: Stoicism.

As Ryan Holiday popularized in The Obstacle is the Way, Stoicism doesn’t concern itself with complicated theories about the world, but with helping us overcome destructive emotions and act on what can be acted upon. Just like an entrepreneur, it’s built for action, not endless debate.

I’ve recently rebuilt my life and business under these seven guiding principles, or maxims as I like to call them. I consider each elemental in my growth as a man, entrepreneur and leader.

Consider this your introduction to Stoicism!

Principle #1: “I can always improve.”

As CEO of Rich20Something, I’ve learned that there’s always something you can do to be better. A better entrepreneur. A better son, sibling, friend or partner. There might be times where you are haunted by mistakes from your past, and you mistakenly equate yourself with your mistakes. It sounds corny, but every day that you wake up is an opportunity to change. And the decision to makes these changes start with a single decision.  

Principle #2: “I persevere when I am frustrated.”

Resilience is in short supply these days. I blame the internet. Because everything promised is easy. Because everybody wants things now. The world has been around for over 4 billion years. Modern civilization has only been here for about 6,000. Don’t rush the process. Things necessarily, and without exception, take time. While that time is elapsing, don’t give up because you’re frustrated. Persevere. Consistency compounds like interest over time. If you’re interested in learning more, check out Meditations by Marcus Aurelius.

Principle #3: “I don’t run from mistakes, I learn from them.”

You are supposed to make mistakes. Every single piece of human knowledge is the result of an initial failure. Every book that’s been written, every idea that’s been thought, every invention that’s been made, has been to solve a problem because somebody, somewhere, made a mistake.

Mistakes push us forward. If you’re categorically avoiding them, you’re not risking enough to reap big rewards. Rather than being afraid of making mistakes, look at them as necessary rites of passage, discard the anguish and retain the lesson. Be courageous. Then help other people to avoid the same traps.   

Principle #4:  “I am inspired by people who succeed.”

I think we all have a subtle tendency to conflate admiration with a bit of hater-ism and self-doubt. At least I know I did this for a while. If we see somebody (especially a friend/family member) who is doing better than us, we come up with subtle reasons to passive-aggressively tear them down in order to bolster ourselves in our own minds. It’s a defense mechanism to protect ourselves from feeling bad for not having the same results in our own lives — and it works wonderfully for a time.

For example, if an entrepreneur friend of mine had an epic product launch and I was jealous, I’d think to myself, “Yeah, that’s really good. I’m so happy for them! They just spend so much time working, though. I really prefer to be more balanced in life.” See what I did there? It’s very subtle.

Instead of looking for subtle reasons to invalidate the accomplishments of others, we should be inspired by their success. In fact, of all the emotions in the human spectrum, I think jealousy is the most useless. When somebody accomplishes something that you’d also like to accomplish, the question you should be asking is not “why are they better than me?” is should be “how can I do the same?” Once you have that mental shift, you’ll be able to focus much more clearly on growth, and you’ll eliminate a ton of subconscious negativity in your life.

Principle #5: “I can learn anything that I want to.”

I was watching the movie Divergent the other day. I can’t remember who’s in it except Zoe Kravitz (for obvious reasons…Zoe, call me!) or what the movie was even about. But I do remember one interesting point: every person in their society had a particular, predesignated role. Some people were selected to be warriors. Some to be intellectuals. Some to be farmers. On and on it went. And there was no opting out. Whatever you were designated to be, that’s what you were stuck with. I can’t help but feeling like our educational system is the same way.

From a very early age, we are told by our parents, friends and teachers that we are good at some things and not at others. Sometimes blatantly, sometimes much more subtly. But the indications are very clear — over we start to believe this and identify with it. I was always a reading/writing kind of guy. I excelled at anything literary very early, and because of that, those traits were reinforced. My teachers would cater to my strengths. My parents would reinforce it by saying things like, “this family doesn’t really do well at math.” And for a time, I thought there was something truly different in my brain that made it harder to me to understand more left-brained, mathematical concepts. Thus, I became what the evidence supported. My test scores were always crazy good with anything involving reading or writing, while my math scores and science scores were mediocre at best.

Once upon a time, I was even a pre-med student. After failing chemistry, I thought to myself — “you know what, this is something that I’ll just never be good at.” Now, I know that is complete horseshit. It wasn’t that I couldn’t do chemistry. It’s simply that I didn’t care about it. It didn’t inspire me. Nothing in the medical field did. Deep interest is the key to acquiring elite level skill. Think about it: when you were really interested in something, didn’t that make it easier to learn? Your brain is incredible and anything that you want to become good at is within your realm of natural abilities. Nothing you need to learn will ever require a genius-level IQ. From rocket science to starting a business. You just need the right approach, patience and above all, confidence in yourself.

Principle #6:  “I can make a difference with my effort and my attitude.”

My high school guidance counselor, Mr. Garcia, had one of those awesomely cliche motivational posters in his office with an eagle soaring high in the sky that said, “Your attitude determines your altitude!” And despite the fact that Instagram has almost completely destroyed the meaning behind inspirational quotes, this one still rings true.

The way you perceive things influences the way that they turn out, and those results in turn influence the way that your beliefs. It all starts with you and your attitude. This is similar to what’s called the Observer Effect in physics, whereby the very instruments used to measure a phenomenon alter the phenomenon itself. You are the instrument! This means that you must guard your thoughts accordingly. If you continually focus on why something will be too hard, the task will seem that much harder because you are magnifying the hard stuff. If you focus on why something is possible, why you’ll succeed, why a task will be enjoyable, you’ll experience those effects much more profoundly. After a short time doing this, you’ll come to realize that in many cases, events are just events — and the impact they have on our lives is almost entirely chained to how we understand and perceive them.

This slightly dispassionate worldview is a core component of stoic philosophy, which I’ve deeply integrated into my life. This isn’t to say that emotions don’t sometimes take control — but rather, when they do take control, you must learn to step outside of the fray and look at what’s happening to you objectively and make an active decision to change your behavior, despite how you might be feeling. When you change your behavior and your attitude, you will greatly influence the outcome of whatever obstacle you are dealing with.

Principle #7: “I like to challenge myself.”

Just like our tendency to avoid mistakes, we often avoid challenges…because, in our brain, “challenge” usually leads to error, or psychological strain, which is painful and unpleasant. But avoiding challenge is trading long term fulfillment for short term safety.

By and large, the very nature of challenges is that they start off difficult and become progressively easier. Along that path, you learn both the skills you need to succeed at your discipline and the person you need to become to rise to the occasion. I’ve learned this in nearly everything challenging I’ve ever done — from jiu jitsu to learning how to solve a Rubik’s cube. Through continuous challenge and with relentless persistence, frustration always gives way to understanding. And then competence. And finally, mastery.

So my prescription for you is to intentionally, actively seek things that will challenge you. If you understand everything in your life, you’re doing it wrong. There should be at least one element of your day that frustrates you enough to constantly seek a solution. It could be something like a complex business problem, or something simple like reading a book that’s above your comprehension. Begin to see challenge and confusion as an indicator that you are on the right path, rather than a sign that you should turn back and head towards more familiar territory.  

Stretch yourself.

A mind once stretched will never return to it’s original shape.



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