In the The Motivation Myth I explain why you should be an "and" by embracing multiple goals and even multiple professions. While many people assume the path to success -- and happiness -- lies in focusing on just one thing, that "specialization" indicates accomplishment and success, oftentimes.

You, me, all of us... we're too good to specialize. 

We should all be serial achievers.

Case in point: Gregory Alan Isakov. Gregory is a farmer. And he owns a record label. And a recording studio. And he's an acclaimed musician and songwriter with six albums under his belt and a seventh, Evening Machines, set for release on Oct. 5. 

Rolling Stone recently featured the album's first single, Chemicals, in their 10 Best Country and Americana Songs of the Week list. The song also made the Spotify Viral 50 Chart. 

Gregory? He's definitely an "and." 

Let's find out how.

You're a musician with your own studio, your own record label, you own and work your farm... how did all that come together?

I went to school for horticulture. I was farming after high school and college. I really dove into soil and plants. That was my world. Music was just doing something I did before work, after work... I was really shy about it. 

But I did push myself to play at local coffee shops and similar places.

The farm I worked on was supportive of the music I was making, so I would do little trips through Montana during the fall and spring shoulder seasons when the farm wasn't as busy... and while I was gone they wouldn't charge me rent. Which definitely helped. (Laughs.)

So I would book a coffee shop, stop at a Kinko's and make 10 CDs to sell after the gig... basically I would make just enough to get to the next show.

I had really small ambitions. But I loved it.

How did you get over your shyness?

To date I've played thousands of shows. But I still struggle with it.

My first opening tour was with one of my heroes, Kelly Joe Phelps. We went from the southeast all the way up to Vermont. It was the coolest thing. I had just gotten into grad school to study mushrooms and deferred entry to do that tour... it was amazing.

I couldn't believe I got to play music for people. It was mind-blowing. It scared the crap out of me but I was getting up there and doing it... and that felt awesome.

I still have that feeling every night.

It surprises me how many performers are fairly shy and introverted.

That actually makes a lot of sense to me. Creation and creativity happen when you're pretty much alone. Playing music with a friend or two in your parent's basement? That's basically every musician. We're not the ones at the parties. (Laughs.) 

Being shy was a blessing. Want to be great at finger-picking? All you have to do is have no friends. (Laughs.)

So you get out of college and you're working on a farm and still playing music...

In terms of money, it was hard to make music work. I would get 50 or 100 bucks a show by selling some records... but it didn't matter. I was in heaven. I worked summers in Colorado on a farm and then played music during the winter.

But then the music side started getting busy. We were getting asked to play festivals. By then I had my own landscaping company and I was also growing food... but I had to let go of most of my clients to do the festivals because I was away so much.   

So we toured during the summers, too... and in 2009 I did 220 shows.

It was cool, but it also felt like something was missing. We were supporting ourselves, the band was stoked, but there was no real balance to my life. Lots of stress, tons of travel, having a relationship seemed impossible... we all felt a little crazy.

And I wasn't writing. I was always in airports, train stations, vans... there was no time to write. I knew it wasn't sustainable.

And then the house I was renting got flooded.

Which I'm guessing you turned into a positive.

I lost everything, but luckily our gear was in the van and stayed dry. So I booked a tour opening for Josh Ritter, stayed with friends when I was home... and eventually found a piece of land and immediately started farming while I lived in my van.

At first I grew seeds for an heirloom seed company because that meant I didn't need to be there the whole season. There's a lot less maintenance required with growing seeds, which meant I could still manage a summer touring schedule.

Which felt like a much better balance. 

Is that why it's been five years between studio albums?

No, the real reason is that I'm a slow m-er f-er. (Laughs.) I take my time. And I write a lot of songs. For this album I recorded 35 songs, fully tracked.  

I love the process. I'll slave over one line of lyrics for a week or more. Sometimes I live with a song for a few months, wait to see where it wants to go... the most valuable thing for me is the time I spend not listening to a song. Then I can come back to it and make sure that I still feel something.

It's like anything creative: When you spend time on it, you get attached...  and when you spend a lot of time on it, you decide it must be great. (Laughs.)

But with time comes perspective. I forget about all the work that went into it and can just hear a song for what it really is. I've ended up throwing a lot away that we worked really hard on... because when I came back to it, it just didn't work for me.

That's the only gauge I know how to use: How something makes me feel.

If it's natural for you to put a ton of time into something, how do you decide when a song is actually finished? 

When I add something and it isn't better. When we make changes and they don't improve the song, then I know I'm done.

I almost have to go a little past "finished" to realize when I've done the best I can.

Does being "slow" impact your touring business? Many artists plan their tours around new releases...

I play the long game where making records is concerned. Early on I assumed I needed a new record when I toured so I would have something new to sell... 

Now the way I think about our records is that they will be around for a long time -- hopefully long after we're gone. So if they take years to make, that's okay.  

If you do good work, it lasts. So I try to make music that will live on.

You never know how people will react. You can't know. But if I know I did everything I could to make an album great... I don't wonder. I don't look back. I know I did the best I could.

Plus, my lifestyle affords me the time. I've always liked farming, I can make a small living doing it, and it lets me do the best I can with my music, too.

A lot of people say they struggle to find one thing they're passionate about... and you've found at least two. Any advice?

When I was growing up I played drums in punk and metal bands. I love that kind of music, too.

You try on lots of things as you grow up. Ultimately you realize there's the kind of music you wish you made... and the kind of music you naturally make.

It took me a while to realize I won't sound like Pearl Jam... because this is what I do. What you make -- what you care about -- when you're alone, when it's just for you?

That's what you should do. 

Doing what makes you happy is often not the quickest path to success. How did you keep going through the lean years?

The most important thing, for me, was making sure that the music felt personal.

When I went to college I studied horticulture because I was scared to take a music class. Music was what I did in my room -- I wanted to protect the personal side of it and definitely didn't want a music teacher in my head. (Laughs.)

No one else can give you that feeling. And that's what drives you to the next gig, and the next.... But that feeling only comes when you love something.

I also grew up during a different time in music. Artists didn't have Twitter or Facebook accounts. I could just focus on music.

A lot of kids worry about online presence, followers, etc. I feel lucky we got to focus on music, and being bad at music, instead of having to also worry about all this other stuff. (Laughs.)

That's what I still tell myself: Don't worry about the Internet. Just write songs. That's all you need to do. Everything else comes from that. 

You're also more focused on music than "success."

I love writing. I love words.  I'll be working outside and come up with a line and get so excited I'm almost giddy. That seems nerdy, I know... but that's the fuel. That's the fuel that gets you to the next place.

Because the business can be a bitch. Touring isn't easy. There will be really hard days where you think, "What am I doing??

There's an economy involved in music, but no one talks about the economy of joy and satisfaction. There's a sweet spot. Your happiness and your comfort level is worth a lot.

We tell our booking agent things like, "When we go to Portland, just book us into the same venue. We love that place." 

She says, "I never hear that from any other artists."

Could we play a bigger venue? Maybe. But being happy -- and loving the experience -- is sometimes more important than making more money.

Published on: Sep 11, 2018
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