The Best Courage Book of All Time (And My Other Favorites)

Via Toni Jones - Evening Standard

Find your way to the smallest room in my home. You’ll have to navigate Juni, our 9-month-old mini Bernedoodle, who will want to tangle in your footsteps as you walk.  

But you’ll find it. It is a tiny space, a converted closet. 

It barely has room for one lamp and enough space for a laptop, a journal, and a pen. 

But look upward, and you will see shelves rising all the way to the peaked roofline. Shelves FULL of books. 

This is the place where I write at home. And this is where I keep my dozens and dozens of books on courage.

You may be curious, so I will list a number of them below, but if you fed to sodium pentothal and forced me to tell you which one was my favorite, that choice will be simple:  

Feel the Fear and Do It Anyway” by Susan Jeffers. 

If ever there was a book whose title best describes its innards, this is the one. Jeffers, in simple, honest prose, details the greatest permission slip to courageous acts I have ever read. You will never, NEVER, she says, escape fear. You won’t conquer it, outgrow it, or evade it. It will want to stop you from doing things beyond your comfort zone. And you have but one job in life:

To feel the fear, and do it anyway. 

I can quote Jeffers all day long. Or you can find some for yourself.  But all you really need to know is contained in the title. The rest, as they say, is commentary. 


Here are some of my other favorite books which give me courage. 

Some may be familiar. Others may not. All of them are powerful. 

  1. Fire Starter Sessions by Danielle LaPorte
  2. Tiny, Beautiful Things by Cheryl Strayed
  3. Do Hard Things by Steve Magness 
  4. The Places that Scare You by Pema Chodron
  5. Life is in the Transitions by Bruce Feiler 
  6. The Fear Cure by Lissa Rankin 
  7. Between Two Kingdoms by Suleika Jaouad
  8. Daring Greatly by Brene Brown 
  9. The Four Agreements by Don Miguel Ruiz 
  10.  The Untethered Soul by Michael A. Singer 
  11. The Road Less Traveled by M. Scott Peck 
  12. Courage is Calling by Ryan Holiday 

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Scott Simon

Scott Simon is a happiness entrepreneur, SYS founder, and author of Scare Your Soul: 7 Powerful Principles for Harnessing Fear and Living Your Most Courageous Life. The book is currently available for pre-order ahead of its release on December 6th, 2022 published by Hachette Book Group.

What Queen Elizabeth’s Life Teaches Us About Our Own Lives

Queen Elizabeth’s amazing life cannot just be measured in years. Although she lived 96 of them, 70 of which she did on the throne. 

It cannot just be measured in the breadth of leadership. Although she saw 16 British prime ministers and 14 US presidents serve during her reign.

And it cannot just be measured in experience. Although she witnessed the rise of Hitler and the Second World War, the entirety of the Cold War, the Cuban Missile Crisis and the fall of the Berlin Wall, the invention of the internet, the dawn of the information age, and the growing threat of climate change.

What seems most meaningful is the way she lived her life: with courage, dignity, and passion, and with a commitment to service.

When someone passes away, our natural inclination is to look backward and take stock of that life. 

And, in honor of the passing of an extraordinary life, I ask you: 

What are YOU doing RIGHT NOW to lead YOUR extraordinary life?

You and I are not kings and queens. But we are living, breathing, embodied potential. 

Queen Elizabeth led a stunningly incredible life with a powerful legacy. 

So do you.

You have the potential to:









Touch, taste, smell 



And whatever else you have buried inside you just waiting to arrive.

Steven Covey famously reminded us – in the 7 Habits of Highly Effective People – to “begin with the end in mind.” 

Can you envision YOUR life when the final chapter is written?  If you can’t … or haven’t in a while … now is the time. 

So, sit back. Pour yourself something cold. 

And think about what kind of life you would feel proud living when your end has come. Think about your life in all of the majesty (whatever that means to you).  

And know that courage is the key to unlocking it. 

If I Had My Life to Live Over by Don Herald 

“I’d dare to make more mistakes next time.

I’d relax. I would limber up.

I would be sillier than I have been this trip.

I would take fewer things seriously.

I would take more chances.

I would take more trips.

I would climb more mountains and swim more rivers.

I would eat more ice cream and less beans.

I would perhaps have more actual troubles but I’d

have fewer imaginary ones.

You see, I’m one of those people who live sensibly

and sanely hour after hour, day after day.

Oh, I’ve had my moments and if I had it to do over

again, I’d have more of them. In fact,

I’d try to have nothing else. Just moments.

One after another, instead of living so many

years ahead of each day.

I’ve been one of those people who never go anywhere

without a thermometer, a hot water bottle, a raincoat

and a parachute.

If I had my life to live over, I would start barefoot

earlier in the spring and stay that way later in the fall.

If I had it to do again, I would travel lighter next time.

I would go to more dances.

I would ride more merry-go-rounds.

I would pick more daisies.”

Scott Simon

Scott Simon is a happiness entrepreneur, SYS founder, and author of Scare Your Soul: 7 Powerful Principles for Harnessing Fear and Living Your Most Courageous Life. The book is currently available for pre-order ahead of its release on December 6th, 2022 published by Hachette Book Group.

The Virtues of Getting Lost: A Photo Gallery

“Getting lost along your path is a part of finding the path you are meant to be on.” - Robin Sharma 

One night after dinner, my daughter surprised me by suggesting that we go for a drive. 

Where to?” I asked.

She shrugged. “Anywhere. Let’s just get lost.” 

She was a high school senior at the time, my only child left at home… and, in many ways, a soulmate. We had always possessed an indescribable connection which I treasured. She is kind, quick, funny, and eclectic; a lover of vintage clothes, late-night baking, and horror movies. And I found myself already worrying about the hole my heart would experience when she left for college in a few months. 

So, seizing on the opportunity, I left my phone on the kitchen counter and we hopped into the car. 

We pulled out of the driveway and into the dusk. From that point on, I took one unplanned turn after another. Before long, we were in unfamiliar territory. 

We paid close attention to our surroundings. Our senses became heightened. Without the usual touchstones of daily life, we opened up to one another. We talked. We sang along to her Spotify playlist. We ended up parking in an unknown spot and watched the sunset die into the horizon.  

We loved the experience so much that getting lost on evening drives became our tradition. 

With Tyler the Creator and Childish Gambino as our official musical co-pilots, we’d marvel at impossibly beautiful stretches of greenery as we sang and talked. 

Getting lost had led us to discover parts of town – and ourselves – unknown to us before.

When Harry Met Sally: A Scene Shot in the Iconic Washington Square Park

If you stand at the very base of 5th Avenue in New York City, right where it connects with Waverly Place, you look directly into Washington Square Park. 

The park has played many roles over its tenure deep in the center of Greenwich Village: it has been a cemetery and a parade ground. A gathering spot for avant-garde artists, NYU students, and drug dealers. A battleground for chess players and a playground for dogs and kids. 

For me, Washington Square Park marked the spot where my fascination for getting lost began.

Although I am an Ohioan by birth, New York runs through my veins. From the very first time I visited, its energy, grit, and majesty fulfilled something strange and powerful within me. I loved to take long walks, taking in the sights, sounds, and smells. 

One day, after traversing the Park, circling its fountain, and crossing below its famous arch, I decided to take another long walk. But, this time, instead of remaining on 5th Avenue uptown towards Central Park, I created a game for myself. I began to cross the streets guided only by traffic lights. 

As I approached an intersection, I would turn and walk in whichever direction the walk sign allowed. That meant following a new path, one that was left more to fate than reason. 

It also meant that, after a couple of hours, I found myself in a place where I had never been before. That’s when I pulled out my beat-up Nikon from my backpack and recorded what I saw. 

Those photos were proof of the beauty and power of getting lost that day. And I would get lost, camera in hand, starting at 5th Avenue and Waverly Place many, many times. 

Have you ever been in a strange city, unfamiliar with the grid, and gotten lost? It could have all gone terribly wrong, but instead, you found the perfect view or a most hospitable café. 

At the heart of many great adventures, the beauty is in getting lost. Embracing uncertainty takes courage, but its rewards are great. So, I ask you: 

How often do you let fate guide your way? 

How often do you let yourself give up a sense of control and open yourself up to surprise? 

How often do you silence your internal GPS that always needs to know where and how you’re going? 

And how often are you truly courageous enough to just get lost? 

Note: all of the following photos were taken on one of my “getting lost” walks uptown from Washington Square Park.  

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Scott Simon

Scott Simon is a happiness entrepreneur, SYS founder, and author of Scare Your Soul: 7 Powerful Principles for Harnessing Fear and Living Your Most Courageous Life. The book is currently available for pre-order ahead of its release on December 6th, 2022 published by Hachette Book Group.

What I Learned from Sending 12,775 Gratitude Texts

Carly, Scott, and their mutual friend Heather.

There is a redemptive power in gratitude. And practicing with a full heart takes courage.

But, if you do, it can change your life.

It changed mine.

There’s a loud knock at the door.

It’s late on a Saturday night in 2015 … long before the days of sweating out Covid infection rates or disputed elections.

Not tonight. I’m sweating out something completely different.

A few days before, my phone had buzzed in my pocket, and I fished it out only to see this text: “Scott, my name is Carly. You don’t know me, but I really need to meet you. Please say yes. How about I meet you at your house this Saturday night at 10:00?”

And now, 72 hours of mind-numbing wonder later (what the hell could this be about?) there’s that knock at the door. 10:00 on the dot.

My bright red door swung open into the night.

Carly, it turns out, is beautiful. No, that is too small a word. Radiant. She’s got these big, curious eyes, long blonde hair twisted down her back, and tattoos trailing down her arms. She smiled, and I fell into it.

“I’m Carly. We need to talk.”

Over the next three hours, we talked nonstop. Carly bared the arcs of her life story: one of aching teenage addiction and near-suicide that led to affirming sobriety. One of empowered marriage and motherhood of three to a life of desperate unhappiness in her marriage and the struggle with the serious illness of one of her boys. She had sought me out because – on the surface – I seemed like the “happiness guy.” Like I might have a word or two of wisdom about divorce and a fulfilling life afterward.

I did have some words for her: About the sheer, goddamn beauty of a fresh start, the rocky but edifying path into co-parenting, the ability to see our kids as a compass, a Northstar, to clearly make our choices out of love rather than fear or hate. And I shared my own up-and-down story: my social awkwardness and anxieties, my constant middle-of-the-night fever dream that I had screwed up my kids, the worry that I would ever REALLY find someone who would love me for who I am.

The only time we stopped talking was when Morty – my black-and-tan French bulldog – sneaked on the couch and slipped his tongue between Carly’s toes. She erupted into laughter each time.

After hours of talking, we stretched and cracked our joints and made our way back to the front door. “Listen,” she said, “This upcoming week is going to be hell. I need something to look forward to. I loved what you said about a ‘gratitude’ practice. How about I send you five things I am grateful for each night for a week, and you do the same?” 

“Sure. Why don’t we just text them to each other? You’ll get through the week. I promise.”

And that is what we did. Five gratitudes by text every night for that week. And then the next. And the next.

And we’ve been doing it ever since … for seven years.

12,775 gratitudes.

Carly is a soul-sister. And I have learned a lot from those 12,775 gratitudes.

So, what did they teach me?

Tom Wolfe once said, “Everybody, everybody everywhere, has his own movie going, his own scenario, and everybody is acting his movie out like mad, only most people don’t know that is what they’re trapped by, their little script.”

Gratitude forces us to open our view. To take the spotlight off of ourselves for a minute. To truly see and appreciate.

It forces us to admit that we don’t have control. That so much of the goodness in our lives is due to other people. That we are leading an exalted existence and that our petty complaints are short-sighted. Gratitude illuminates what is important to us, and sometimes uncovers the realization that we haven’t exactly been thankful to others the way we could be. Gratitude scales down our ego, sometimes making us feel small, but revealing the goodness and interconnection that exists between us all.

In my Scare Your Soul book, I wrote a chapter about the real power of true gratitude, and why it takes such courage to embrace it as a practice. Here is an excerpt:

If you practice real, true, authentic, vulnerable gratitude, it shines a light deep into your soul. By choosing my nightly practice with Carly, I am showing both her and me what is important to me, what lights me up, and what challenges are turning into opportunities. I share it all unabashedly. And in doing so, I’ve had some revelations:

When I practice authentic gratitude, I am happier and more present. I still have days full of frustration, and yes, I still can take things for granted, but on the whole, I find myself appreciating life more.

Gratitude flips your conceptions. It asks you to find some amount of value in people and experiences that you didn’t like, agree with, or want as a part of your life. How hard is it for you to feel gratitude toward your relatives with polar opposite political views? Gratitude leads us to a place of more compassion and understanding.

Gratitudes don’t always have to be positive. Feeling grateful for acknowledging and surviving a challenging time is immensely powerful. In fact, as Carly and I have progressed, more than half of our gratitudes are about the challenges that we face; we know now that they, indeed, will be the times that will teach us, fuel us, and make us more empathetic humans. You have to choose it: As we discussed previously, there are important steps in fully experiencing gratitude, and they are not always evident in the rush of our busy days.

Not practicing gratitude is like having a Ferrari (feel free to substitute your own dream car here) fully gassed in your garage but never actually taking it for a spin.

Here are a few tips I learned for courageously being more grateful in your life:

  1. Be actively aware: Take time and slow down. We must be awake and aware in our own lives to identify the goodness around us. Make space for seeing the interactions with others and what they mean at the moment, the gifts that nature, spirituality, and community give to you.
  2. Feel the feeling: Identity what brings goodness into our lives, and then pay attention again. This time, tune into what swells within you. How do you feel at the moment? And where in your body or heart does that feeling sustain itself?
  3. Begin to savor: Really become aware of the experience of your gratitude, and treat it like the first, slow bite of your favorite dessert.
  4. And, in the end, thank and thank again: Most gratitude practices fail to include this final step. Reach out and thank from your heart. It creates ripples throughout the world. When we thank someone for bringing goodness into our world, we create a ripple effect. Our gratitude expands the world’s heartbeat…

Want to start practicing courageous gratitude in your life right now? Try our gratitude challenge!

It’s free and will kick off a brave grateful experience.

In the meantime, be grateful for who you are and what you have. You’re a masterpiece. And you didn’t do it alone.

Want courage challenges sent straight to your inbox every week? Click here to sign up for the Scare Your Soul newsletter!

Scott Simon

Scott Simon is a happiness entrepreneur, SYS founder, and author of Scare Your Soul: 7 Powerful Principles for Harnessing Fear and Living Your Most Courageous Life. The book is currently available for pre-order ahead of its release on December 6th, 2022 published by Hachette Book Group.

The Top 20 Courage Quotes of All Time (and 5 You’ve Never Seen Before) 

[Scroll down if you’d like to skip the compelling story about why our favorite quotes are some of the most important possessions we will ever have in our lives]

Last year was the year of the humble brag and the inevitable downfall...

From as early as I can remember, I was dreaming up stories. Part of it was to escape a childhood where I felt muzzled by shyness and low self-worth, but I truly loved how words – like perfectly interlocking puzzle pieces – fit together in such a way that it created a reaction deep inside someone other than me. For decades, I wrote: mainly for others, in speeches and dedications, and in countless blog posts and Instagram captions. 

Then, last year, after decades of writing in obscurity, an incredibly surprising book deal with a “Big Five” publisher came my way. 

While the contract was being negotiated by my new, impressive New York City literary agent, I fantasized about the days ahead. I could see myself all writer-ly, decked out in jeans with ripped knees and Birkenstocks, sitting with an espresso at a cafe table in the sunshine, pouring my ample wisdom into my MacBook.  

When the ink on the contract was dry, I humble-bragged about the opportunity to family and friends.  

First came the inevitable high fives and the hugs. The go-get-em-tiger emails. The positive support was palpable.  

But my few author friends responded to the news … well … somewhat differently

I kept on receiving this all-knowing glance reminiscent of when – with two boisterous kids under the age of two at home – I would get a visit from a friend to proclaim that they were pregnant for the first time. Their fresh-faced naiveté was so cute and endearing. And they had NO IDEA what they were about to get themselves into. Yes, my author friends of all stripes – fiction, non-fiction, historical fiction, reverse-harem-romance-fiction – all gave me that same look. Then they shared their secret, second lives. 

While others were busy watching Netflix, they were sitting in terror at their desks, sweating as they contemplated that blank page that somehow magically re-appeared every single morning.  

And, my friend, that is EXACTLY what happened to me. 

Each morning at 5:30, I would glance in hatred at my phone alarm. I’d trudge downstairs in the dark and squeeze into my designated writer’s office no larger than a coat closet. Actually, it used to be a coat closet. And there I would sit, not knowing what the hell to do. 

My confidence sank. 

And then I had an idea. I would make the coat closet office into an inspiration zone. 

I salvaged the tiny round lamp I had bought on clearance from Target. I populated the closet’s thick wooden shelves with my beloved, multi-hued courage books from my collection. And, most importantly, I printed out sheet after sheet of courage quotes. I scotch-taped them to the walls. 

And there I would sit each morning. Yes, in terror. But with each passing day, I would look at one of the quotes and, inspired, begin to write.

Really great quotes are works of art. 

I know what you’re thinking. Hear me out here. 

How many books were published last year, do you think? 

The latest estimate of books published worldwide is about 2,000,000. With an average of 273 pages per book, hundreds of thousands of authors brought a whopping 546,000,000 pages full of freshly-written text into the world just last year. 

Why is it that, every once in a while, of all that immense amount of ideas, one sentence sticks? 

The quotes that are economical yet expansive. Like cities buried inside a raindrop. Like a salve, we squeeze out onto our sometimes dry and cracked lives. They somehow rise above the millions of pages of text to enter the lexicon of our lives. 

The very best of them deserve key places in our hearts and minds. They are Bottecelis. 

In my year that began with the humble brag and tumbled into the abyss, there were countless quotes that I relied on … that gave me the inspiration I needed. I hope that they help you. 

Here are my Top 20: 

My Top 20 

  1.  Life shrinks or expands in proportion to one's courage. - Anais Nin
  1.  I have been absolutely TERRIFIED every moment of my life -- and I've never let it keep me from a single thing I wanted to do. - Georgia O'Keefe
  1.  Our deepest fears are like dragons guarding our deepest treasure. - Rainer Maria Rilke 
  2.  You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You are able to say to yourself, "I lived through this ... I can take the next thing that comes along.” - Eleanor Roosevelt 
  1.  Confront the dark parts of yourself, and work to banish them with illumination and forgiveness. Your willingness to wrestle with your demons will cause your angels to sing. - August Wilson
  2.  Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it. - Steven Pressfield 
  3.  I've missed more than 9,000 shots in my career. I've lost almost 300 games. 26 times I've been trusted to take the game-winning shot and missed. I've failed over and over again in my life. And that I why I succeed. - Michael Jordan 
  1.  One isn't necessarily born with courage, but one is born with potential. Without courage, we cannot practice any other virtue with consistency. We can't be kind, true, merciful, generous, or honest. - Maya Angelou
  1.  We must let go of the life we've planned so as to have the life that is waiting for us. - Joseph Campbell
  1.  The terrorists thought they would change our aims and stop our ambitions, but nothing changed in my life but this: weakness, fear, and hopelessness died; strength, power and courage were born. - Malala Yousafzi
  1.  If we did the things we are capable of, we would literally astound ourselves. - Thomas A. Edison
  1.  At the root of most fear is what other people will think of us. - Ryan Holiday 
  1.  The secret is to leap widely and strangely over the deep, not knowing what's down there, but pretty certain in some small crevice there must be a small purple flower. - Dick Allen 
  1.  Success is not final, failure is not fatal: it is the courage to continue that counts. - Winston Churchill 
  1.  There comes a time when one must take a position that is neither safe, nor politic, nor popular, but he must take it because conscience tells him it is right. - Martin Luther King, Jr. 
  1.  Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. - Steve Jobs 
  1.  The only way that you'll actually wake up and have some freedom is if you have the capacity and courage to stay with vulnerability and discomfort. - Tara Brach 
  1.  Inaction breeds doubt and fear. Action breeds confidence and courage. If you want to conquer fear, do not sit home and think about it. Go out and get busy. - Dale Carnegie 
  1.  Fear is the cheapest room in the house. I would like to see you living in better conditions. - Hafiz 
  2.  When we least expect it, life sets us a challenge to test our courage and willingness to change; at such a moment, there is no point in pretending that nothing has happened or in saying that we are not yet ready. The challenge will not wait. Life does not look back. - Paulo Coehlo 

And Five You May Have Never Heard Before

  1.  So write.… Not like a girl. Not like a boy. Write like a motherf*cker - Cheryl Strayed 
  2.  You don’t need a better computer to become a writer. You don’t need a better guitar to become a musician. You don’t need a better camera to become a photographer. What you need is to get to work. - James Clear
  3.  If we must have milestones—mine will be measured by how much joy I have collected at the end of each day and how often in this life I have truly, deeply, opened. - Janne Robinson 
  4.  I am not lucky. You know what I am? I am smart, I am talented, I take advantage of the opportunities that come my way and I work really, really hard. Don’t call me lucky. Call me a badass. - Shonda Rimes 
  5.  Doubt kills more dreams than failure ever will. - Suzy Kassem 

And One More, Just Because 

Lift up your hearts. Each new hour holds new chances. For new beginnings. - Maya Angelou

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About the Author

Scott Simon

Scott Simon is a happiness entrepreneur, SYS founder, and author of Scare Your Soul: 7 Powerful Principles for Harnessing Fear and Living Your Most Courageous Life. The book is currently available for pre-order ahead of its release on December 6th, 2022 published by Hachette Book Group.