The Unautomatablog
Unautomatable Audio
Thoughts in Between Ed and Tech #8: It's All About the Journey 🛣️

Thoughts in Between Ed and Tech #8: It's All About the Journey 🛣️

When things feel right, you're on the path!

When you’ve found something to do that’s worthwhile; that’s meaning. When you can feel it, you’re in the right place at the right time.

Even after another late night, that’s how I’m feeling heading down to Palo Alto in the bright California summer sun today.

I think that this feeling is what startups are all about. It’s just fun.

And when the whole team can share in the uncomfortable parts of the journey together and laugh about it - that’s what it’s all about.

That’s culture. That’s community.

Oh, and fresh off of the “putting on your white belt” article, I officially spent the entire last week working from MacOS for the first time in my life. It was painful, it was uncomfortable, and it was meaningful.

What crystallizes these threads of growth, the path, meaning, uncomfortability, enjoying the journey, and culture and community? Besides #unautomatability, the lessons shared during an amazing panel discussion that I was fortunate enough to moderate recently did a pretty good job of bringing it all together.

Check out the TL;DR tweetstorm or the full video 👇

The Never-Ending Story

A book that was recommended to me a few weeks back really reminded me that entrepreneurship truly is all about the journey. Zero to IPO, by Frederic Kerrest, stirred a deep resonance in me on many levels. Give it a read, and it will remind you, too, that it really is always day 1.

For us, somewhere between ed and tech, each day we put our white belt back on, it really is always cohort 1. Some days it genuinely feels like it, like our launch a few months back. And some days, not so much.

In the coming week, we’ll be graduating our most recent MLE cohort while preparing to spin up new MLE and MLOps cohorts in the next month and a half. Also - watch this space - because we’ve also got some newness on the horizon 🌅.

What really resonated with me in Kerrest’s book was that the pace of change simply increases; nothing ever gets simpler or easier as we or as our companies grow. The startup journey from seed to Series A, B, C, D, and up to IPO are all just steps along a growth trajectory - which, by no means stops at IPO! Rather, an initial public offering is just the most efficient way to raise enough capital for continued growth. Kerrest’s line that went something like “I can raise $10B any day of the week now; the question is why and what would I do with it?” really stuck with me.

Similarly, we as individuals that are part of families, teams, communities, and organizations must continue down our own paths of growth, one painful step of overcoming the inevitable suffering associated with growth at a time.

The journey is never about aiming at things based on their objective simplicity, complexity, ease, or difficulty. All of our journies as individuals and startup builders are subjective journeys to be undertaken from where we are - considered in the context of the evolving world around, us, yes - to where we want to be. The next step, as it were. Even the next level, perhaps.

This is exactly what I heard from each successful panelist this week. That’s what I heard from Frederick Kerrest about each step of his and his company’s journey, which continues to this day. And that’s what I've learned on my own from taking life one step at a time.

The idea that it’s all about the journey, and that we compare ourselves and what we’re working on to who we were and the state of affairs that we were in yesterday, has served as a consistent theme for me in my own life, especially since early 2020. Seeking the next great adventure, time, time, and time again, seems to be not only the secret to success in business for individuals and companies alike, but also the secret to success and long-term fulfillment in life beyond work.

I personally feel grateful to be on my own path of becoming. For me, for now, it’s all about my individual journey toward becoming unautomatable, somewhere between ed and tech.

Good luck on yours!

The Unautomatablog
Unautomatable Audio
This is where I share my thoughts on stuff related to Unautomatability in the 21st century.
I'm currently reading my Unautomatablogs ( in my own voice. I'm a huge fan of audiobooks, and nothing is better than hearing them from the author!