Scott Simon

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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“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.

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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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.

…

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