Newsletter Sabbatical
After five years of publishing high value quick hitters, it's time to dive deeper
Welcome entrepreneurs! I’m so glad you’re here.
Today is a big day for me. Five years ago, I finally came back to writing—after taking fifteen years off to build companies.
To celebrate that anniversary, today’s newsletter will be the last I write for a while—ironic, I know—because I’m taking a six month sabbatical from this newsletter to focus on something larger.
But before I sign off for a while, let me tell you a story.
One afternoon during my final weeks of college, I waited in my favorite professor’s apartment for the rest of the class to file out.
I was graduating with a creative writing degree, and my dream was to write novels. The professor, who was also the head of the writing department, was a published author of multiple novels as well as a handful of poetry books. I felt my heart thump in my chest as he turned to me. “What’s up, Ryan?”
I sat back down at the large table in his living room. “I really admire your work, and it’s amazing how you’ve made a life for yourself as a writer and teacher. Now that I’m about to graduate, what the hell do I do?” I was hoping he would tell me the secret to building a career in the completely illogical vocation I’d chosen, ideally in a way that didn't involve starving.
It’s been nearly 20 years since that night, but I still remember his response like it was yesterday.
“You’re a great writer,” he said. “You just don’t have anything to say that hasn’t been said better by someone else. My suggestion would be to stop worrying about writing, and go live a little. Make some mistakes. Then come back and write about them.”
I was resentful at first; nothing like a gut punch to the old ego to set you on a straight path to success. But, in hindsight, he was right. My early work was, to borrow a phrase from Billy S, “told by an idiot, full of sound and fury, signifying nothing.” I could turn a phrase, I could cause a reaction in a reader, but I didn’t know what I wanted to communicate through my work. Hell if I was ready to hear that at the time though.
Out of depressed confusion, I stopped writing and set about the process of finding something worth saying. Fifteen years, three startups, one lovely marriage, and two amazing kids later, I found myself again at a crossroads. I had been ousted from the company I founded, and once again, I had to figure out what the hell to do with my life.
The easy answer was (of course and as any post-exit-founder will tell you) to start another company. But as I engaged in a process of deep self-inquiry over an 18 month sabbatical, I found that, once I’d worked through my reflexive desire to accomplish big things to make myself feel ok, there was a still, quiet voice inside me that wanted something simple.
“Write,” it told me.
And so, nearly two decades and many mistakes later, I picked the pen back up. As I began, I couldn’t help but wonder if I had anything to say.
In the five years since that moment, I’ve found that I have plenty to say.
I owe you a debt of gratitude, dear readers, for helping me see that. Through this newsletter, I’ve had the opportunity to meet so many wonderful entrepreneurs, and it’s through those relationships, and through the many hundreds of thousands of words written in support of those relationships, that I finally found my voice.
Writing for all of you has enabled me to build Inside-Out, a thriving executive coaching firm, that’s allowed me to support some of the top founders in the world to expand into deeper levels of self-awareness, self-trust, and self-love (and scale world changing, low drama companies).
None of that would have happened if I hadn’t followed that still, quiet voice, telling me to write.
And now, that same voice is telling me to take a break. To create some space, and allow something new to emerge.
And so I will.
I’m not prepared to say I’m writing a book. But I’m not not writing a book, so do with that what you will. Maybe a book does come out of this space. Maybe it’s something else. Maybe absolutely nothing comes from it, apart from more time with Laura and my boys.
Either way, I’m ok with that. My role in this creative journey is not to steer. It is to surrender to the flow, and do the best, most faithful, most authentic work I can. And right now, that starts with creating space.
What’s next for the newsletter?
This is not goodbye.
This is see you later.
For the next six months, any public writings will be primarily on LinkedIn, so come say hi there. And of course, I’ll continue to coach top founders as they build amazing companies without losing themselves in the process (if you think I might be helpful toward your journey, please reach out).
And then, in six short months, I’ll be back. Ready to jump back in with both feet.
Having made something bigger, potentially. Different, almost certainly.
The sabbatical I took after leaving VNN completely changed my life.
I can’t wait to see how this next one hits.
If you liked reading this, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
The secret to leadership (why authentic leadership is simply more effective)
How to pitch a big vision to investors without setting yourself up to let people down
Executive Coaching for Entrepreneurs
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency built by entrepreneurs, for entrepreneurs.
Through a unique combination of deep executive coaching and strategic execution support, Inside-Out has supported entrepreneurs leading some of the fastest growing companies in the world to develop into world-class leaders, and build high-performance, low-drama companies.
We coach leaders how we want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
To learn more about working with I-O, click here.
I admire your willingness to step away / take a break, in order to fill the bucket again. It's similar to why I've transitioned, for now, into learning and telling other peoples' stories, instead of continually telling my own.
P.S. I'm all-in on the book you're not writing.
See you here in six months.