8 Lessons From “Stillness Is Key” by Ryan Holiday That Helped Repurpose My Entrepreneurial Career

Derick David

Photo by S Migaj on Unsplash

It’s funny how even one book can change your life so suddenly.

And all you need is to read that one book.

This is how exactly I felt when I read “Stillness Is The Key” by Ryan Holiday.

I felt that life changed.

Also, it is crazy to think that I was extremely hesitant to read this book just a year ago for a number of reasons, including having a long backlog of books I’ve promised myself to read and going through a hard time due to the pandemic.

Then a few months ago, I started noticing that my entrepreneurial career lacked direction.

I had no plans and I was just lost.

I wanted to do something to impact people’s lives, but I had no idea how.

So, I decided to read a book hoping it would bring alignment.

This time, I chose to read Ryan Holiday’s Stillness is the Key.

What happens next to me is amazing. The relief and satisfaction were unexplainable.

It was like two stars aligning together after a long time.

What I love about the book is that it embodies the message itself.

So, I’d love to share the lessons that I learned that I’m now applying to my entrepreneurial career that I strongly believe would do service to yours as well.

1. Humanity is one big project

What is our purpose in life and why are we here?

Sometimes the big questions lead to even bigger questions. The more we ask, the closer we get to the truth. However, no one truly knows how far have we gone.

We might be all going on our ways, but I love to see humanity as one big never-ending experiment. We all work together as one and revolutions and innovations waiting to happen will be made by people working together, as one.

Just like a project I did back in college, I had to test my assumptions if students would want to use my app. Humanity as a whole isn’t that different.

Except, we don’t know who’s responsible or what are we testing it for.

Whether we see or not, we all collectively work for one goal. Then, you can divide it and you will see a group of people working on one goal and so on.

In the bigger scheme of things, we’re all unconsciously working together for this one big project.

2. Let go of emotional debts

Emotional debts aren’t like any other debts in existence.

It has to be paid every day.


Because peace is almost impossible when you are racking up petty debts in your head. You’re just emotionally killing yourself.

I had a few debts in my own life and I had to forgive:

  1. Ex-partners
  2. Unsupportive friends
  3. College friends
  4. Cousins

I just realized I had accepted the truth, forgive, and let go.

When I started doing that, I felt more at peace in life.

Ryan Holiday did so well in explaining this that it hit me like a slap from my Mom when she discovered I was cutting classes back in high school.

3. Measure your internal accomplishments

Let me start by saying, success should be measured internally. Meaning, something that you are in control of like discipline, consistency, and hard work.

You will never be truly happy if you measure externally. I’ll tell you that.

Stillness is the key helped me see that we look too much outward that we completely ignore what’s inward.

Well, this means that we put too much value on things that we cannot control and we fail we started stressing out because we failed miserably.

If you put in the hours but still see a failure, you should be grateful.


Because you managed to still put in the hours. At that point, what’s more, important is to keep moving. The odds of your success grow as your keep trying and trying.

Shoot for stars and just keep shooting. Eventually, your mark is everywhere.

4. Live by the moment, but always visualize the future

Remember, there’s no greatness in the future. Or clarity. Or insight. Or happiness. Or peace. There is only this moment.

Don’t get me wrong, it’s totally acceptable to live in the future. But don’t live too much in it that you forget what’s in front of you.

This is how often we ignore our family.

Visualize the future, but live by the moment.

Ryan Holiday emphasizes that the idea of stillness comes from your ability to focus and appreciate the moment.

He’s absolutely right.

I have been working too much on building my entrepreneurial career that I almost always miss family dinners.

You can still work hard, but don’t forget what’s in front of you.

They might not be here tomorrow.

Entrepreneurship can be balanced.

5. Trust the process, your process

As the old Zen proverb says,

Chop wood, carry water.

What else is supposed to create the results you envision if not for the process that comes by it?

Stillness is the key has been a great reminder to me that:

  1. You have to fall in love in the process
  2. Focusing on the results can lead to failure
  3. Loving the process yields power

These are applicable in pretty much anything in life, especially in entrepreneurship because there’s a lot of processes involved.

Focus on the process.

Just like how I am focusing on writing this or just how you are focusing on reading this word by word.

6. Use peace to boost productivity

The process makes you productive and when you focus on the process, you find inner peace because it’s one of those factors you can control.

Leverage your peace to do more work and if productivity is measured in outcomes, then don’t get too lavish about how your milestones.

  • Be mindful of the process

Find inner peace and you’ll get things done, effectively and efficiently. If you’re having a hard time finding it, practice mindfulness through meditation.

Trust me, it does wonders.

7. Be purpose-driven

Some activities often have no purpose.

You just do them for fun or to entertain yourself.

Their usefulness is tied in allowing you to step away from your process and be at peace with doing something which yields no specific outcome.

Be mindful and show intent with your actions. Then, make sure it aligns with your purpose or don’t do it at all.

Being purpose-driven goes back to the question why are we here?

Find a purpose helps you find the answer.

And when you know your purpose everything will start to make sense and you will find your direction in life.

As an entrepreneur, having a purpose is a necessary element since you are working on one big idea solving a pain point or a problem.

If you don’t find your purpose, someone else with it will take advantage of you.

8. Use stillness to attract inspiration

My favorite thing from Ryan Holiday’s book is that it helped me understand that stillness can actually help find your inspiration.

It helps you concentrate your energy on one thing and makes you wonder why you are doing what you’re doing.

I really loved this.

I use this simple technique to brainstorm ideas for my company.

Without the inspiration and brilliance that comes from stillness, it’s hard to define yourself as something or think clearly.

If you learn to be still at any given moment, you can learn to harness those flashes of inspiration and turn them into a driving force that helps you execute actions.

Whenever you start losing inspiration, sit back, relax, and stay still.

Magical things will come out of you next.

Final thoughts

These are the great life lessons you can take away from Ryan Holiday’s book “Stillness Is The Key” which helped me repurpose my entrepreneurial career.

It’s one of those books I’ve read that puts everything in perspective.

In all honesty, if it weren’t for his book, I would've gone crazier in these crazy times of the global pandemic. Stillness is a way to boost your performance in what you want to do.

Stillness is what brings light to your darkness.

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10x Top Writer on Entrepreneurship, Innovation, and Startups.

New York, NY

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