'Discipline Now, Freedom Later'

It was a fun life.

Billy Oppenheimer was working as a ski instructor in Colorado and in New Zealand — chasing winters in the hemispheres to do what he loved most.

But as he penned blogs to keep friends and family up to date, a question pulled at him: “Is this someone who I want to be?”

“I thought if I’m still doing this in 10 years, I’ll look back and say, ‘It was an easy life, but I did not make the most of my time,’” he said.

So Oppenheimer began looking for a role model about a decade older whose footsteps he might want to follow in.

He ultimately sent best-selling author Ryan Holiday a cold email, offering to work for him for free. He’s now served as Holiday’s top research assistant for several years.

The Daily Coach caught up with Oppenheimer recently to discuss sending an effective cold email, the fast rise of his own “SIX at 6” newsletter, and the critical concept of “engaged detachment.”

This interview has been condensed and edited for clarity.

Billy, thanks a lot for doing this. Tell us about your childhood and some key lessons from it.

I grew up outside of Philadelphia in Conshohocken, Pa. My mom was a stay-at-home mom. I have two older brothers, so she looked after us.

My dad ran a custom sports apparel business. He was a really hard worker, but he was really good about not bringing his work home. If there was stuff going on, he didn’t let that affect the way he was around us. I really appreciate that now because I know how difficult that can be when you have a hard day. It's hard not to let it follow you around a bit, but he was really good at separating it.

You played lacrosse at Lehigh and then lived in a few different countries. Can you take us through your first few years after college?

I had a pretty good college career, and after I graduated, I went to Australia to play and coach. That was a super-formative experience for me. It was the first time I left the country and was really out on my own where I didn’t know anyone. I was playing on their top senior team and coaching a sixth-grade team as well.

I loved it in Australia, but I had always had the idea that I’d like to do a full ski season in Colorado, so I applied to be an instructor. What I learned in Colorado was a lot of the instructors go down to the Southern Hemisphere when the season was over and teach skiing year-round. I did that for a couple of years, and it was in that time that I started a blog. A reader of the blog recommended one of Ryan Holiday’s books. That got me onto his work, and I started devouring it. That led me to reach out to him and ultimately working with him.

You end up sending Ryan a cold email. What did you write in it and what advice would you give someone in general about writing a cold email or making a cold call to someone they want to work for?

The way I framed it to Ryan was that I was reading his books, and after I’d read one, I’d read four or five of the books he’d mentioned in the bibliography. I just wanted to figure out how he was producing his work and sort of reverse-engineering the writing process.

So I told him I’m doing a lot of this reading… and I’m sure you have a pile of books you need to read and research for your future writing. Maybe there’d be a way I could help. He said he could use some assistance and would be in touch.

Looking back, I think I would’ve done it slightly differently. I think it’s better if you’re cold-emailing someone to send some sort of deliverable item. I should’ve told Ryan, “I just read this biography of George Lucas, and I thought this anecdote could make for a great Daily Stoic email” and left it at that. It’s trying to show him I have a sense of what he finds interesting and that I have an ability to spot a good story. I think the way to go about it is to do the work you’d like to do for that person, not say, “Hey, I love your stuff. Let me know if I can help out.”

You’ve now worked as a research assistant for Ryan for several years. Can you tell us about your notecard system?

The general idea is to capture anything interesting you come across in your reading, when listening to a podcast, watching a documentary, or whatever it may be. The way it works is I read a book and as I’m going through it, I’m earmarking pages, underlining stuff, writing in the margins. Then, I put the book aside for a couple of weeks and I go back through with a stack of blank notecards. If any of those things I highlighted on the first read through still hold up as interesting or useful, I transfer it onto a note card.

Every note card I make, I’m trying not just to copy word for word but put it in my own words and write it in a way that it might appear in a future piece of writing — kind of in paragraph form. I file the notecard away in boxes that are loosely broken up by theme.

It seems like you’re really starting to branch out with your own Twitter content and newsletter. Why was it important for you to create your own identity and not just get typecast as “Ryan Holiday’s guy?”

Ryan was encouraging me to put my own work out there. I was getting good feedback from him. I felt I was improving as a writer and I was doing the notecards and had a bunch of stuff I was gathering from my own reading and research that wasn’t necessarily a fit for him. I wanted to start sharing it.

We had a conversation where he asked what I was trying to do and where I was trying to get. He said the way the relationship would be most beneficial was if he had a clear sense of what I was trying to do. Then he could help guide it.

I told him I wanted to carve out my own writing and maybe get to the point where I was doing books as well. One of the main things you learn from Ryan is to start a newsletter and build an audience that’s familiar with your writing. He's been a huge supporter of it—links to it in some of his articles and on social media. At some point, he said to me that in addition to the newsletter, I have to figure out a discovery engine, a way for people to find out that the newsletter actually exists. He said that I needed to start either finding outlets to write for or grow on social media so more people could find my work.

I started dabbling with Twitter — really just adapting the material I was using in the newsletter into a Twitter format.

As far as being typecast, I get people who say, “This reminds me of Ryan Holiday’s work,” but that’s a huge compliment to me. I’m still just a huge fan of his work—he’s my main influence and writes in the style I love reading. I’m not super worried about, “Oh, he’s just a little Ryan Holiday,” because I take that as a compliment.

You have your known newsletter as well, “SIX at 6,” that comes out on Sundays. What do you want readers to take from it?

I was just reading this biography of Jim Henson, who was the creator of The Muppets and Sesame Street and all these great TV shows and movies. He talked about how we wanted to leave people with an “up feeling.” You walk out of the theatre, and you just feel better because of the experience you just had. I really liked that. That’s my aim. I want people to read the newsletter and feel energized by a story or a takeaway that’s given them that "up" feeling that Henson talked about.

You recently wrote about this concept that might be relevant to a lot of leaders called “engaged detachment.” Can you explain what that is?

I got that from a book by Rich Cohen, who was writing about his dad, Herbie Cohen, who was a great negotiator who was brought into all these high-pressure situations. That was his mantra. The way he was talking about it was the strongest position to be in as a negotiator is to care but not that much, to approach it like if I lose this, it doesn’t matter. When you come at it from that perspective, you’re in a position of power, because either way, you sort of win.

Shaun White, before he’d drop into a halfpipe during the Olympics, would say to himself, “Who cares?” It was a way to take the pressure off. Obviously, he works for years and years to get to this one moment, he was engaged and had put in the work, but in that pressure moment, he tells himself to detach and just do what he does, and the score will take care of itself.

It would seem like with your days, you don’t have an unbelievably strict schedule. You have freedom to structure your hours. How do you maintain discipline within that?

It’s pretty loose. I know the things I want to and need to work on. I usually make a notecard the night before or first thing in the morning with the three to four things I need to make progress on to make it a good day.

I actually have a notecard on my desk that’s another Ryan phrase. It says, “Discipline now, freedom later.” I think about that even when I’m getting back from a run and don’t feel like untying my shoes. The discipline now will pay off later. I look at that notecard and think I could be loosy-goosy and procrastinate and let things go, but I try to make just a little progress every day on things and then I feel good about it. If I feel like I throw a day away, I’m sort of kicking myself. I want to avoid that.

It’s not time blocked. It’s just bullet points of my four main projects. A lot of what I work on isn’t due tomorrow. The deadline for this is two months away, so I do napkin math at the start like, “If I do this amount of work on this each day, I’ll come in well ahead of the deadline.” I know if I make this amount of progress, I’m in a good spot.

Q&A Resources

Billy Oppenheimer ― Website | Twitter | “SIX at 6” Newsletter | LinkedIn