Hello, Courageous co-conspirators! I’m back.
You'll want to read this whole issue. I've got a big announcement, and you may even find yourself quoted below.
So. It’s later than I thought I’d return, but I’m still pretty proud of myself: for ten weeks straight, I sat down and wrote. Ten articles shipped since the start of summer. It's honestly the most consistent I've been on a personal project in a long time, and your responses have been a big reason I kept going.
Then suddenly, your inbox went silent. I imagined it: tumbleweeds rolling by in the background, you clicking around to re-read old issues, breathlessly opening your inbox every Thursday, only to find nothing. Since this is undoubtedly your only newsletter subscription, you likely felt abandoned. My apologies. And I’ll have those tumbleweed props returned to the warehouse this afternoon.
Truth is, the pause did concern me a bit. I wasn’t ‘spent’ after ten weeks, but the volume felt like an accomplishment, one that makes a convenient excuse. The moment I indulged it, life agreed. My day gig got more intense, the weekend work kicked in, my family needed more from me, and a trip was already on my calendar for the end of September.
Life is always ready to fill the void you create. My real fear was losing the writing habit and disappearing on you altogether. That would leave you in the lurch, but it would also be an abandonment of my self. I've done enough work over the years to recognize the pattern; I know where it comes from and how to judo it, just in time.
Funny how often we return to where we began. My first issue, about the liminal space, pointed out the stretch between an external shift and your next big move. Our brains hate it, don’t they. They churn up anxiety and race us to the other side, for safety's sake. A pause can feel so reckless, so unproductive. But in reality, it gives us the space we need to deliberately choose the direction worth taking. And for me, I needed this break to consider what’s next for The Courageous.
So I gave myself three weeks off.
…which easily turned into four.
If you read my last issue, The Talent Tax, you know about my energy spectrum. I was living at the ‘commuter’ end of it in September. Head down, same route every day. No rockets, no fireworks.
And at the end of the month, I flew out of town.
A group of old friends reunited in the wilderness of upstate New York. There were seven of us. There should have been eight. We celebrated the life of our friend Marc, who we lost suddenly this year to cancer. He was only 55. The trip was originally his idea, to reunite all of us after about 15-20 years, so we kept the commitment in his honor.
Then I spent some quality time with my half-sister down in Brooklyn (thankfully no home invaders this time!) and a few different friends in Manhattan. I also got up to the ‘burbs to visit with my adoptive fam, for my Dad’s birthday.
A memorial for a 55-year old, followed by an 81st birthday. We never really know when the clock might stop.
On the flight home, I sat next to a 6-month-old jostling around in her mother’s arms. I kept thinking about how many of us keep squirming, just waiting for the right moment, or a better moment to start. The idea we keep mentioning. The career move. The side project. The reach-out to a potential collaborator. The version of ourselves we keep almost becoming, if only we could wrest ourselves from our familiar comfort zone.
Unsplash: Lucas Favre
Reminder: there’s no better moment coming. The moments just keep coming, until you’ve used them all up. Best to be here, now. Give life to your ideas. Make them real. Sure, it’s much easier for me to type than for you to create. But really, would we be here right now, you & I connected in this particular way, if I had kept waiting for the right moment to start?
Back in The First Move, I wrote about the trim tab. A tiny rudder turns a bigger rudder in order to turn the giant ship. No matter how big the stakes feel, your actual move can be small. A two-degree difference in habit, held long enough, can steer you somewhere completely different than where you were, say, just ten weeks ago.
While I was away from the keyboard, I went back and reread all the kind comments you've sent me since I’ve started. Here’s a small sampling:
“Love what you wrote, speaks right to me. Subscribed and can’t wait to see what comes from this!”
“I still don’t know what will happen next in my career, but I am on a much better path. Thanks for writing this. It really resonated with me.”
“I'm in a rebuilding phase and your story pushes out any last vestiges of victimhood I might have been feeling lately.”
“I actually thought your 9/10 article was going to be about 9/11. This is your most vulnerable and Courageous writing, Kevin.”
“I just read this and wow. A lot of echoes of what I have been going through”
“Your stories and insights have been spot-on for me since you started THE COURAGEOUS. Thanks for taking the time to write this. This is needed.”
“I love what you are doing - thank you for creating this, I am inspired by you.”
“It is amazing how much you’ve been through in the last decade. It was really compelling how you wove those experiences together in your writing. Thank you for sharing”
“KEVIN! Just read your article. What a ride. And your timing with some of this hit me - reading what you wrote just confirmed my feelings around my own decision. THANK YOU! aaaaand ROLL OUT!”
After years of social media strife, this feedback pleasantly surprised me. You tend to reach out when something hits home. Please know though - I want to learn from you too, so if you take issue with or have a different take on anything I've written, bring it!
I’ve mentioned a few times that I’ve got larger plans for The Courageous. This newsletter was just the first step. Here’s that big announcement I promised:
Next month, The Courageous are going LIVE.
I’m calling it The Stretch. Let’s connect, let’s inspect, let’s get going!
We’ll kick off with a two-hour Sunday Zoom, where we get honest about where you’re at right now, where you want to go, and to help you pick your first move. Then you go back out into your world and take action, with an accountability buddy if you need one.
Two weeks later, we’ll reconvene to share what happened, what didn’t happen, and what you need going forward.
Remember, going it alone rarely works. This is your chance to work on realignment with others in the same mode and to reinforce for ourselves why it all matters. But most importantly, it can spark the momentum you’ll need to stay in action through the end of the year and position you for bigger moves in 2027.
This one’s on me.
That’s right, it’s FREE. I only ask that we keep identities and everything shared fully confidential for all the reasons, and that you complete a brief feedback questionnaire when we wrap.
For anyone who wants to keep going after that, this opens the door to deeper work. I’ve got plans for what that looks like, but I’ll want your input, to ensure you get the results you want.
So November’s your big opportunity: take action on your next moves and become a founding member of the Courageous community, which will empower more of us to realign with our most Courageous creative lives.
You've already been building this with me, whether you knew it or not. Much of the work comes straight from what I’ve written and the thoughts you’ve shared back to me. So thank you again.
Next week I’ll return, I promise - with the details & signup for The Stretch. I’d love to have you all in, but we’ll likely need to limit the size initially and create a waitlist for another round in December.
Actually - if you want the details sooner, you can reply with one word: “STRETCH” - and I’ll send you the signup page in advance!
Can’t believe we’re already in the home…stretch…of 2026. Just another reminder that we really don't have much time. Let's spend some of it on purpose, together.
We’ve got this.
Onward,
Kevin
Founder, THE COURAGEOUS
PS Feels good to be back on the horse. Thanks for opening and reading it all!
PPS If someone in your life keeps talking about a change they haven't made yet, please forward this to them and encourage them to sign up!