Stoicism For The 21st Century: A Cheat-Sheet

Life Is Filled With Obstacles.

Whether we like it or not, life is filled with painful experiences, people who hurt us, and situations out of our control.

Stoicism, a school of philosophy established over 2,000 years ago, isn't for the dry academics or for deep conversations after having too much wine. It's a framework of thinking for right now. For life in the 21st century.

Stoicism is a tool. A tool for better thinking and looking at the world differently. It’s a tool that we can use to become better entrepreneurs, better friends and better people.

Stoicism helps transform negative thoughts and emotions into a sense of calm and perspective. It makes me question my own assumptions. It's painful but it works.

Years ago, I made a quick-and-dirty list of commandments and questions that I turn to whenever I'm stuck, feel like shit or when life kicks me in the balls . Now, I'm sharing it with you.

Use this guide whenever:

  • You feel depressed;
  • You've just had something blow up in my face or go wrong;
  • You feel overly-emotional;
  • You feel judgmental & angry;
  • You're stuck in unproductive thoughts;
  • You want to give up;
  • You just got rejected;
  • You need a kick in the ass to keep working

It has helped me immensely over the years. I hope it does the same for you.

Keep Things In Perspective

Over the long-term, we're all dead.

Ask yourself if this still matters 100 years down the line, six foot deep. Do you want to waste your precious time alive on bullshit?

Remember, “This Too Shall Pass”.

Always see the humor and reality of things:
- Imagine the politician you hate having sex;
- Imagine that annoying co-worker taking a massive shit;

Things can always be worse.
You could have lost a limb, your parents could have died, you could have been homeless or addicted to opiates.

Repeat To Yourself:
"You Are Not Going To Die From This.”
”You Are Not Going To Die From This.”
”You Are Not Going To Die From This."

Mind Your Story

This is not some unique misfortune Fate picked out especially for you. It just is what it is.

It's your choice to put 'I' in front of something. Can you extract yourself from the situation?

The worst thing to happen is never the event, but the event and losing your head. Because then you'll have two problems.

"Choose Not To Be Harmed - And You Won't Feel Harmed.
Don't Feel Harmed - And You Haven't Been"
- Marcus Aurelius

"If you think you're patient, you will be”

The person ready to be disappointed won't be.

We often choose the ominous explanation over the simple one. Could there be a simpler explanation?

Take your situation and pretend it is not happening to you. Now what does it look like?

There is the event itself and the story we tell ourselves about what it means.

Does getting upset provide you with more options? Probably not.

Become Stronger

How can you transform this weakness into a strength?

Be anti-fragile. Expose yourself to hardship and outside influences. As muscles grow from strenuous activity, so do our spirits and emotional resilience. With enough exposure, you can adapt and get comfortable with anything.

"How Can I Become Strong Enough To Be Useful In A Crisis?"

What will happen if you give up?

People have risen from lower places than you. People with more disadvantages have overcome the odds and succeeded. People turn shit into sugar all the time - shit that's a lot worse than whatever we're dealing with.

When you factor in vision and work ethic, much of life is malleable.

Would you rather be strong enough to weather this crisis or happy to have been released from it? Would you rather be happy or strong?

"Getting Rejected Or Snubbed Isn't Up To You.
Deciding To Become Better And Working At It? That Is."

Never let a crisis go to waste. In times of crisis, greater change is possible. We can reinvent ourselves and do away with what no longer serves us.

Always keep Murphy's Law in mind. Hedge your bets and preemptively address points-of-failure, but know that failure's always possible.

Put In The Work

There's very little that cannot be overcome through perseverance and putting the work in every single day.

If there is even a 1% chance, be ready to give every ounce of effort and energy to make it happen. If effort affects the outcome, die on the field before you let that chance go to waste.
Whether it takes one year or ten, don't give up until there is absolutely nothing left that you could do.

Calmly walk up the mountain, day after day, through sun and rain.
Better that than sprinting up the hill in a burst of enthusiasm and to giving up halfway through.

“Slow Is Smooth. Smooth Is Fast.”

More often than not, action is the solution to most of our problems.

Create momentum.
When being held back or facing some obstacle, start.
Start anywhere.
Say yes.
If you can just get started, you can build up momentum and overcome it in the long haul.

Could you be doing more?
Those who attack problems and life with the most initiative and energy usually win.

Never be in a hurry.
Never be worried.
Never desperate.
And never stop short of the finish line.
Be like a flowing river, with enough time and pressure, ravines can be carved out.

Think Progress, Not Perfection.
Worry About Your Trajectory, Not Your Current Situation.

Focus on doing the reps, not worrying about the end-result. Do the smallest task you can do right now and do it well.


Life is too short to be caught up in emotions and fear. Keep things in perspective, be mindful of what story you tell yourself, try to be stronger, and put in the work. That's all there is to it.

Fore more in-depth thoughts on stoicism, check out ‘The Obstacle Is The Way’ on Amazon or the notes I took while reading.

Related Posts:

No items found.

Sign Up For Friday Favorites!

Join the 500+ people who receive my Friday Favorites newsletter in their inbox every week. It's a mash-up of the most interesting links, books, and ideas I came across that week, as well as my latest articles and book notes. If you're curious and looking for high-quality information, you should definitely join.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.