Welcome to Rough Terrain

Because the world needs another Substack newsletter

Hi, Cy here. Welcome to Rough Terrain, my erratically published newsletter about… well, I’m not sure yet. Definitely some content on Product Management. And tech trends, that’s for sure. Organizational leadership. Wealth management and crypto too. I don’t really have a unifying theme to this whole thing, I’m kind of making it up as I go.

So why write when I’m not even sure what I have to say?

Because the world needs to know how I feel about things, damn it!

Nah, not really. I’m writing to myself, to clarify thoughts about subjects that are occupying space in my brain. They may be of interest to you, and that’s awesome, I hope you’ll find this engaging. I not-so-secretly hope I can use my newsletter as a way of meeting smart, engaging people out there on the interwebz.

I’m calling my newsletter Rough Terrain. There’s a story here:

First, I’m a big fan of the saying “a smooth sea never made a skilled sailor”. Supposedly said by Franklin Roosevelt, who knew a thing or two about persevering through hardship. I use this quote when encouraging others to lean into tough situations because it’s the tough situations that make us better. Or as Tim Ferris likes to say, “a person’s accomplishments in life can be measured by the number of difficult conversations they are willing to have.” Basically, stress can be a good thing (as in, eustress), so long as you embrace it and don’t do the more instinctual thing of avoiding it. I remind myself of these quotes when I’m shying away from a thing I don’t want to do because I know it’s going to suck.

That quote is about the sea. Which is problem for me, because I’m a 15 year veteran of the US Army. Naval themes don’t mix well with Army folks, because, you know, its the Navy. So what’s a land-based equivalent to the kind of violent seas that make great sailors? Rough terrain.

Rough Terrain is harsh, nasty land that is difficult to maneuver through. Think marshes, cliffs, basically anywhere you wouldn’t like to go. Unless of course, you like the hard stuff. That’s the point - to look for the places that are hard to go because it’s how we get better. To make sure that stress is eustress, not distress.

Also, as a bonus, Rough Terrain is a special skill in the US Army, where select combat engineers conduct airborne operations (jump out of plane with a parachute) and deliberately try to land in the the trees. Seriously, go look, it’s a real thing. The first 3 years of my Army career was as a combat engineer, so I guess I hold a special place in my heart for those crazy bastards.

Finally, because I blogged once ago. In 2015, I wrote a lot about my transition out of the Army as a coping mechanism for all the (dis)stress that experience gave me. It helped a lot, and I was told by others it helped them too. You can go check out my old articles. I’m ashamed of the tone, but some of the content holds up:

• Make Your Own Damn Luck (yes, I’ve been writing about stress and smooth seas before!)

• A Book Review of Stan McChrystal’s Team of Teams (I’m quite proud of my comparison between Stan McChrystal and Stannis Baratheon, rightful king of Westeros)

• Be Steel, Not Iron

So that’s it. One more newsletter from a middle-aged tech bro with modest life accomplishments. It’s not what the world wants, it’s what the world needs.

I hope you’ll find this useful, I know I will.

Yours,

Cy