OTR, Take 40: Phil Cook - Southland Mission

Listen along on Tidal or Spotify (but really, ditch Spotify and help pay artists more on Tidal!)

You gotta walk that lowly road

It's an absolutely perfect late fall morning in Pittsburgh: a windless chill that sits alongside you rather than cutting through you mingles with a soft light muffled by indistinct cloud cover. There's a threat of oncoming winter, but enough Autumn left in the air you can comfortably expect a high around 50. Chef's kiss perfect.

Normally, I'd be out walking Clare, but I did this thing last weekend and my knee is killing me. Clare is not impressed.

She brought up Audra's walking shoe and tossed it at my feet.

Here's the thing about good masterminds: they leave you with more (and better) questions than answers. They challenge you to see things in an uncomfortable light. And, if you do your part, you let that light shine on you, your life, and your business and you are better able to see where work needs to be done. Most importantly, having identified these things, you feel empowered to take action and you have people walking alongside you, on similar journeys, ready to call out your bullshit and help you succeed.

The goal was 480 miles. We hit 668.

Nothing sacred, nothing saved
Get your ass on the morning train or get the hell out the way

For a long time, I thought it was silly to invest in myself. I'm here to take care of other people and I can just figure it out on my own. Both of the statements in the previous sentence are, at best, half-truths. Incomplete. Delusions that permitted me to feel comfortable in my mediocrity.

Isn't it true that we're always our own best mark?

I hadn't been fully aware of it, but for most of my life, I've put myself in positions where it looks like I'm doing a lot, making progress, and checking off boxes. What a small way to live. There have been several moments over the past two weeks that have shaken my comfort: some wide-ranging and eye-opening conversations in Colorado with the Unrationed crew, a really helpful reorienting of how to approach thinking about my work through a discussion with Marshall Lichty, my ADHD/business coach, and a little nugget that Seth Godin causally dropped earlier this week:

The contribution you make as the leader of a business or a team is the quality of your decisions, not the tasks you perform.

This past month has been one where the path has become clearer, even if a bit more terrifying – but isn't everything a bit more frightening when you can see it in focus?

Gothic Gospel: just look at that iconography!

I stumbled upon Phil Cook's Southland Mission right about the time I was getting divorced, but it's one of the few records I listened to during that period that I don't associate with my ex or the divorce. Other records are a different story.

Southland Mission is a joyful record, even if it doesn't always seem like it ought to be. There's something earthy and grounded about the record, its preoccupations, its language and themes, that gives a very human vibe – a sense of a flawed yet searching person driving it. We get this from the very beginning, with the first track on the album, "Ain't It Sweet?"

This video is perhaps my favorite version of the song (you really get a sense for what a wonderful guitar player he is). Try listening at first just to get the vibe of the song. Listen to the guitar line, that steady insistence at the beginning – the build up, the gradual incorporation of additional melodic elements, the knotting-into of the song. Ain't it sweeeeeeeeeet, well ain't it sweeeeeeeeet?

What if I were to tell you it was a song about him and his wife dying and being buried next to each other?

Well we were wide awake
Then we're dead and gone
And we'll find a way
Just to carry on
Carry on
And we'll never be alone

None of this see-you-in-heaven nonsense. This is a straight existential reckoning turned into gospel: no matter what, we'll be together. Ain't it sweet?

Ain't that the way it is?

You may not have heard of Phil Cook, but you almost certainly know of some of his friends. In the mid-2000s, Phil, his brother Brad, and some little-known guy named Justin Vernon moved from Wisconsin to North Carolina and formed a band named DeYarmond Edison. That band made a couple of pretty good records, then split, with Vernon escaping to a certain cabin in the woods of Wisconsin (you may have heard that story) and the brothers Cook forming a pretty fun folk rock band named Megafaun.

So often when one member of a group of musicians (or actors/comedians/lawyers/humans) suddenly becomes a huge star, the other members of that group become curiosities, a moon lit by the light of the star. This does a disservice to both men or women. Setting aside the sociopathic and/or narcissistic star, most every "star" looks at his peers and sees people who helped make him – often, it's difficult to discern why he was the one who "made it."

And those who don't blow up into stardom aren't suddenly any better or worse at what they do because of their buddy's new-found fame. Phil Cook was making amazing music in 2002 and is making amazing music today; he just hasn't appeared on any Kanye or TSwift records.

This is just a note to encourage you to look at the people around the formative years of the Greats: you don't become great on your own and there are inevitably a number of shockingly good people in that early orbit, pushing and challenging, and continuing to do pretty great stuff.

Now that you’re known by everybody, yeah
It’s hard to be anybody, anybody else

Over the past year and a half or so, I've found that I've been more consistent in putting myself in groups of people that I don't quite belong in. With people who are steps (or leagues) ahead of me. People who have different skill sets than me. People whose attitudes are different from mine. People who challenge and push me, people who have no business spending time with a chancer like me.

Every few years, I start feeling very uncomfortable, precisely because I'm feeling comfortable. There are two things at work here. First, thanks to my ADHD, I get bored with easy things very rapidly. As soon as I figure something out, it's dead to me. Done. A butterfly pinned to the page. Second, there's something in me that equates comfort to stagnation. This may or may not be healthy, but it is a reality.

This past weekend was confirmation for me that spending the time to get in the right rooms, with the right people, doing the hard things not because they have to but because they choose the challenge is exactly what I want.

If you listen carefully to Southland Mission, you'll hear Justin Vernon's voice show up as a backing vocalist. Do you think he does that for someone who didn't force him to get better? For someone who didn't push his songwriting and singing? For someone who didn't help form him?

There's something magic about guys like Phil Cook. Both in the forcing function they played for the Justin Vernons of the world, but just as importantly, in the fact that he's out here just making ridiculously great records because there's something in him that he needs to let out. Something that compels him to pick up the guitar or banjo and be part of the community.

As I said last week, find your tribe. Find your person. Find the forcing functions for yourself – and, don't lose track of this, your job is to do the same for other people.

How are you feeling at the end of the day?

Get the latest episodes directly in your inbox

{{#if @member}} {{/if}}