Newsletter #3 - Do The Thing You've Always Wanted To Do

August brought our first book club meeting, a mountain road conquered, and proof that the best adventures happen when we stop talking about doing something and simply begin.

Welcome to another The Wild Gentleman Newsletter. Read on.

Updates

We had our first The Wild Gentleman Book Club in early August. While the discussion centered around the book for July, The Great Gatsby, the small group covered a wide range of topics.

• The book club selection for August is Viktor E. Frankl's Man's Search for Meaning. (You can get a copy from The Wild Gentleman bookstore.)
• We will be meeting on Tuesday/Wednesday in early September in Newton, MA, for our second book club meeting to discuss the book.

More details on the first meeting and the next book selection are below.

Latest Blog Posts

• The most recent blog post is "Against Camaraderie: Building Brotherhood via Community and Friendship." The key takeaway, against the backdrop of the book club discussion and some recent writings on male friendships: "The problem with modern male relationships is that we often mistake camaraderie for friendship and wonder why we feel unfulfilled or alone despite being constantly surrounded by other men."
• I also published "The Great Gatsby: A Reader's Guide for The Wild Gentleman Book Club" to prepare for the book club meeting.
• Lastly, Paid Members of The Wild Gentleman can access premium content like the recently published "The Ultimate Book Lists for Men: A Curated Resource Guide."

Hope you all are making the most of the summer and finding some moments of inspiration, spending some time outdoors and with loved ones, and taking care of yourselves in general.

Lastly...

One big ask: A good friend's son is in the midst of a heroic fight against cancer. The family could use any and all support at this juncture. Please help if you can: Thumbs Up for Dec: Fighting Childhood Cancer.

Wild at Heart. Refined in Mind.

The Wild Gentleman Book Club

The first The Wild Gentleman Book Club get-together is in the books, and it was an incredible experience.

We will be meeting again at Paddy's Public House in Newton next month. The meet-up will be one of the first Tuesdays or Wednesdays of September. I will be sending out a poll via Instagram to see what works best for everyone.

(Follow The Wild Gentleman on Instagram if you don't already.)

Our August book is Viktor Frankl's Man's Search for Meaning.

I tried to keep the initial group for the book club small, but there is a lot of interest, so I am expanding it somewhat. I'll be reaching out via email and/or Instagram to more folks over the next few weeks. Anyone else interested in joining the book club, please email me at dennis@thewildgentleman.com.

Man's Search for Meaning appears again and again on the "Must Read" or "Favorite" lists of people I respect as book curators and thinkers. It appeared in almost all the lists shared in The Ultimate Book Lists for Men: A Curated Resource Guide, for paid The Wild Gentleman subscribers. It is a book I have never read but have always wanted to.

So far, it is living up to the praise.

(If you want a copy, the book can be ordered at The Wild Gentleman bookshop.)

To wrap up our discussion on Gatsby, I wanted to share a recent NYTimes "The Daily" podcast that focused on the 100th anniversary of the book.

Here is the podcast on Spotify:

Speaking of doing things that challenge us, I want to share a story about finally attempting something I'd been avoiding for twenty years.

Doing the Thing

Speaking of doing things that challenge us, I want to share a story about finally attempting something I'd been avoiding for twenty years..

The last week of July and into the start of August, our family spent our week of allotted time at my wife's family's shared "Camp" up in Maine. I have been going to "Sunnybank," the three-season lake house sitting on Highland Lake, for a week or two for more than twenty years now.

It is beautiful. A place where these days you'll more often hear the cry of "Can we go tubing?" than you'll hear the cry of the ever-present loons. It's a great place to drink a Maine-brewed IPA, go skinny dipping at dusk to embarrass your teenagers, and go for runs longer than you probably planned.

To get to the camp, you take a long drive up the appropriately named Mountain Road in Falmouth. For two decades, I've watched bicyclists struggle to power up the steep two-mile incline; quite often, I've thought, I could run this. But I never conquered Mountain Road.

From the camp, I've run ten miles, half-marathons on a slightly hungover whim, and sprints up a nearly vertical incline not far from the lake. But never have I been so bold as to attempt to run Mountain Road.

Until this year.

The first morning in Maine, I woke up and, although not fully convinced yet that I had it in me, I just kinda decided to do it. To run Mountain Road. To do the hard thing.

There are so many examples of this reality from both fiction and non-fiction writing that make it clear that starting off (in this sense, literally) and taking the proverbial leap compounds. From Brené Brown and Roosevelt's "The Man in the Arena" speech to Sahil Bloom's advice in his book and newsletter to the teachings of the Stoics. In fiction, but the one that jumps out is Santiago from Hemingway's The Old Man and the Sea.

The parallel works because both involve a long-avoided challenge, physical endurance, and the realization that the real victory is in the attempt itself.

And so, I have been putting myself out there more here with The Wild Gentleman. I've been having more personal, unguarded, and deep conversations. And I so I set off and decided to do the thing.

I didn't feel too confident, and I was a bit stiff and rusty, heading out for the massive 2-mile climb to even get to Mountain Road. But once I got to the top of the hill and began bounding two-and-a-half miles straight down, I was in it, and there was no turning back. The run back up the massive hill took a lot of willpower and planning. I broke up the continual incline into three separate "hills" to conquer. And, I just pushed through.

Getting to the top, I made a decision. Even though I had two more (mostly downhill) miles back to the camp, I was going to celebrate the accomplishment I just completed right in that moment.

I slapped the Mountain Rd. street sign with glee. I let out a joyous "Whoo-hoo!" barbarically yawp-y enough to make Whitman proud. I leaped in the air and punched my fist into the air. All in the middle of a heavily trafficked backwoods road. I smiled. Then I finished the run, almost ten miles of it, and returned to the house where family (who were asleep when I had set out about an hour-and-a-half before) were puzzled but not surprised by my long absence.

Now I share this story for a number of reasons. A lot of what I have been reading lately has helped me overcome some of the doubts. A lot of what I have been writing about motivated me to live up to the gauntlet I'm throwing down to seek more adventure. And a lot of the conversations I've had lately have convinced me that many of the things we think we can't do are kind of in our heads.

Like Hemingway's Santiago finally hooking his great fish, climbing Mountain Road represented my own test of perseverance against self-imposed limitations. Hemingway wrote, 'A man can be destroyed but not defeated'—and sometimes we need to prove that to ourselves, one hill at a time.

But more than anything. I wanted to share the moment I accomplished the feat and then realized that I needed to celebrate. To feel joy at achievement. I often think about how I don't sit in joy enough (I see this in a lot of others as well). We do something incredible and then move on. No! Slap that sign! Let out that Whoop! Jump in the air!

We are all doing hard things. Don't just check your successes off a list of to-dos. Revel in the wins. Share the story of the time when you did the thing you've always wanted to do.

The Gentleman Shares

Quickly, here are a couple of recent reads that I wanted to share, as well as some books recommended at our The Wild Gentleman Book Club meeting:

"To Be Young, Gifted, and Black at Fenway" - by Michael Thomas, The New Yorker.

This is just an incredible read. Beautifully written, this is an excerpt from Michael Thomas's book, The Broken King.

A Swim in a Pond in the Rain - by George Saunders.

I love this book in which Saunders teaches about reading, writing, and, most importantly, life as he breaks down the short stories of the Russian masters. I got the name of The Wild Gentleman from one of the characters from Ivan Turgenev's story, "The Singers."

Mike recommended this book at The Wild Gentleman Book Club meeting. I love it myself. There are so many rich threads to pull on; this book will come up again.

"The Death of Partying in the U.S.A.—and Why It Matters" - by Derek Thompson via Substack

I think I found this article via Tim Ferriss, but some of the numbers shared are wild.
An excerpt:

The death of the party fits into a broader social phenomenon that I called “The Anti-Social Century” in a cover story for The Atlantic. At a time of surging anxiety and mental distress, Americans spend more time alone today than in any period in recorded history. Face-to-face socializing has plummeted in the last two decades by about 20 percent. For unmarried men and people younger than 25, the decline exceeds 35 percent, which might explain why these groups seem to have fewer friends than ever.

How to Help the Wild Gentleman

I've had a lot of people reach out and ask:

1. How can I help with The Wild Gentleman?
2. I live in Atlanta, D.C., or Denver (for example), can I take part too?

First, I am incredibly grateful for all the outreach from folks wanting to help with this project. From offers to write a blog post to notes on strategy and direction, there are a lot of men who The Wild Gentleman not only resonates with, but who want to play a part in building a place committed to growth, authentic conversations, and becoming the kind of men the world needs.

At the moment, I'd appreciate your help in two ways:

• Keep sharing ideas, book recommendations, blog ideas, and more to dennis@thewildgentleman.com
• Spread the word! Here is a link you can share for The Wild Gentleman signup page: Signup. But more than anything, just share with others anything about what The Wild Gentleman is up to that you like. Word of mouth is great; social media is better. A big step I've taken this year is realizing that sharing things I love with others and sharing appreciation are the things that give me purpose. Maybe sharing The Wild Gentleman will tickle that itch for you as well!

Second, if you are not in the Boston area and would like to read the monthly book, please do so. And, if you feel so inclined, please feel free to send me an email or note with your thoughts. There are a few gentlemen across the country who are already reading this month's selection and have no way to attend the book club meeting. I am exploring ways to expand The Wild Gentleman geographically and have received some examples of digital book clubs that seem to work well, which could serve as one potential route. However, the key to The Wild Gentleman community is gathering in person. So I am wrestling with how best to approach this type of growth. Please share any ideas: dennis@thewildgentleman.com

Upcoming...

The Mountain Road taught me that most of our limitations exist between our ears. This month, as we read Frankl's insights about finding meaning through difficulty, I challenge you: What's your Mountain Road? What have you been telling yourself you can't do?

Until next month—keep reading, keep questioning, keep doing the things that scare you a little.