What Bob Ross Taught Me About Music, My Career, and Life

Untitled design

This post originally appeared in “The Load In” the weekly digital magazine from Startup Musician. To sign up for free, fill out the form below.

I had a strange experience the other day. I played at Perch, one of the coolest spots in LA. They take great care of their musicians, and the steak frites… oh my furriggin goodness.

Anyway, after we finished playing, a girl came up to me and asked one of the strangest questions I’ve ever been asked,

“How long did it take you to get good at the bass?”

I stood there thinking about my answer for entirely too long. It felt only like a moment to me, but in reality it was probably something like 10 seconds. I said, “uh… well, I mean, I’ve been playing for a long time, since I was 10, so I don’t really…”

She went on to explain that she’s tried playing tenor sax but she’s interested in other instruments and is interested in playing the bass. So she wanted to know, “how long until I’m good?”

I gave her a couple of pointers on bass technique, we said “nice to meet you” and went our separate ways. But her question stuck with me for the rest of the day. How long did it take me to “get good” at the bass? When was I “good enough” to do this for a living? When did I cross over from amateur to… professional?

Pictured: me and all my professional friends.

Pictured: me and all my professional friends.

I remember my first paying freelance gig. I remember it because I couldn’t believe I was getting paid for something so easy and fun. But what about my second gig? And the third? At what point did just a couple gigs turn into my regular thing?

I’ve found that in music, in freelance careers, and in much of life, scenes don’t change abruptly, but gradually. There isn’t a curtain close, fade to black, and opening of a new set and characters. It’s much more fluid than that. It’s quite honestly a lot like one of the great artists, kindest people, and genius minds of our time, Bob Ross.

The Master at work.

The Master at work.

Have you ever seen this show? Like, actually sat down and watched an episode? It’s unbelievable. You probably know him as the “happy little trees” guy, but he’s so much more than that. The man is a wizard of painting; his wand a paintbrush, and  his hat a tacky caucasian perm.

Bob Ross shot 31 seasons of his PBS show, The Joy of Painting, and while all his paintings are unique, the format is the same. Here’s the secret formula of every painting Bob Ross has done.

Step 1: Start with a light coat of paint already on the canvas.

This is the secret to EVERYTHING.

This is the secret to EVERYTHING.

Step 2: Drop in hints of sky, clouds, and water.

At this point the painting isn't looking like much. But be patient, young padawan.

At this point the painting isn’t looking like much. But be patient, young padawan.

Step 3: Completely ruin the painting by putting some dark paint right in the middle of the canvas.

What the hell, Bob?

What the hell, Bob?

Step 4: Absolutely blow my mind by painting the snowy peaks of a mountain range.

I'm sorry I ever doubted you. You clearly know your stuff.

I’m sorry I ever doubted you. You clearly know your stuff.

Step 5: Continue adding trees, rolling hills, and water lines.

Now this painting is coming together!

Now this painting is coming together!

Step 6: Totally ruin the painting, but this time for real because what the hell are you doing painting over that whole section?

Those mountains were beautiful! You're just going to put a blotch of Van Dyke Brown over it? Come on dude.

Those mountains were beautiful! You’re just going to put a blotch of Van Dyke Brown over it? Come on dude.

Step 7: Blow my mind again by revealing that it was a beautiful tree all along.

I feel a metaphor coming up...

I feel a metaphor coming up…

Step 8: Continue adding foreground features like bushes and reflections.

Oh this metaphor is going to be so bad...

Oh this metaphor is going to be so bad…

Step 9: The roller coaster of artistic emotion finishes and we’re left with a masterpiece.



Seriously, I love Bob Ross.

Music, freelance careers, and much of life follows the Bob Ross formula. You don’t really know what you have until you take a step back and look at it. When you’re in the middle of it, it’s hard to see the bigger picture because all you see is a big splotch of Van Dyke Brown in the middle of your sky and you question everything. Even when the mountains are set and looking good, there’s still so much stuff to paint.

Looking back on my own career and life, I don’t have one specific moment when I flipped the switch and all of a sudden I was a “good at bass”. I don’t have a clear moment when I switched from being an amateur to being a professional. It just sort of happened gradually, in the same way that the trees of a Bob Ross happen, or the same way you and an acquaintance become really great friends. I have a few WTF moments here and there (when Bob is seemingly ruining his work), but it ends up working out somehow.

I’ve talked about this concept before, but your life and career is a fluid timeline. Everything overlaps, changes, and evolves. With all that change it’s easy to lose sight of where you are and notice the changes that have happened. With that in mind I’ve got two pieces of advice for you:

1. Don’t wait for someone to tell you that you’re good at your thing, or you’re “good enough” to be a professional. Just start painting. (But you know in this case, that’s a metaphor for whatever it is that you do in music. Unless, you actually really want to paint). Keep your head down in your work and keep going.

2. Every so often, take a step back to see how far you’ve come. Look at what you’re painting. Doing this every day will discourage you, but doing it every year will show you the bigger picture, where you’ve been, and where to go next.

Bob Ross is now available to stream on Netflix, but there’s even more episodes on his YouTube channel. Do yourself a favor, next time you can’t sleep, pull up some Bob Ross and you’ll be lulled to sleep by the calming voice of a genius.