Welcome to the Woodshed. This column is all about my journey as a guitar student. That’s right—I said student. I’m 36 years old and only started playing four years ago. Late last year, I was challenged to post a new guitar video every day for 90 days.

Consider this my love letter/hate mail to the process of learning an instrument as an adult. As I share my stories, I’ll also be sharing tips and tricks, things that are working for me, things I’m stuck on, musicians who are inspiring me, and songs I’m listening to and/or learning. Finally, I’d love to hear from you, too.

Come say hi at @jtdawsonmusic.

I was talking to a fellow guitar player the other day and she was asking me what she could do to improve. My answer was simple. “Practice more,” I said. Like I wrote in my last column, I strongly believe that’s the not-even-remotely-secret sauce to the whole thing.

“But it’s not easy for me like it is for you.”

I almost fell out of my chair. “Is that really what you think? That learning has been easy for me?”

“You always look like you’re having so much fun. I can tell you love it. I get so frustrated sometimes and it’s hard to practice when I’m frustrated.”

Let me clear this one up right now. It is fun and I do love it. Playing guitar has unlocked this vast expanse in my heart I didn’t even know was there, and as dramatic as this sounds, I believe it has saved my life in ways. But nothing about it has been easy. I get frustrated all the time. Don’t believe me? Ask Grant, my guitar teacher. He’ll tell you about all the times I’ve cried during lessons. Actually, he won’t because he’s a gentleman, but that doesn’t mean it hasn’t happened.

I’d love to be able to say something uplifting like, “I just love it so much that the frustration doesn’t get to me,” but that would be a big fat lie. In the darkest of times, I’ve convinced myself that I’ve reached my limit as a player—as if that’s a real thing—and I’ve started to throw around words like quit.

But I don’t quit. Or at least, I haven’t yet. In fact, every time I hit a wall like that, I eventually break through it and come out the other side so much better than I was before. What I’ve learned, though, is willpower and determination alone aren’t enough for me to keep going. I need accountability, and I need a lot of it. If you’re an adult learning to play guitar, you probably need it, too.

90 Days, 90 Songs, 90 Videos

When I first picked up a guitar in 2014, I didn’t have any expectations. I thought I’d learn some chords, maybe a few songs, have a few laughs and move on. And once I started, I never thought about it too much. I just kept practicing and I kept not quitting. Toward the end of 2017, it suddenly hit me: I had progressed far beyond what I ever thought was possible.

Grant found this revelation unsurprising. “You work hard. What did you think was going to happen?”

“OK, but what do I do now? I wasn’t supposed to get—“

“What? Good?”


It’s not that this was a problem, but it did feel like a turning point. Up until then, I was just a girl in my living room, learning to play guitar—and to be clear, I still very much am that—but with this realization, everything shifted. What would be possible if I put a little more effort in? Put a little more of my heart on the line? Dared to care a little more?

I wanted to step up my game but wasn’t sure how to do it. Then, while on a trip to Nashville in September, I had a blinding flash of inspiration. I met up with Grant, who couldn’t wait to hear what I had come up with.

I was excited. “I’m going to start a new Instagram account just for music stuff.”

“That’s great! Lots of people do that.”

“Exactly. And to start it off right, I need to post regularly. So starting October 1, I’m going to post a new guitar video every day until the end of the year. That’s 90 videos in 90 days.”

Now this did surprise him, and he had a lot of questions. To be honest, I hadn’t fully thought it through, so I was making up answers on the spot. In that moment, though, the task I’d set for myself didn’t seem that difficult. Surely I could think of 90 songs I liked well enough to learn. And since I was practicing every day anyway, would it really be much of a stretch to film it? Plus, if anyone followed along, I’d probably get some encouragement! And going public would certainly hold me accountable to sticking it out.

I sat on the idea for a couple of days to give myself an opportunity to come to my senses and call it off. While I was waiting for that to happen (spoiler alert, it didn’t), I went ahead and made a preliminary song list to see if I could get anywhere close to 90. I got to 30 before saying, “Good enough! I’m doing this!”

I set up the account and announced what I was about to do. There was no turning back.

The “How

I returned home from Nashville on September 18, which meant I had two weeks before I needed to post my first video. I created a spreadsheet so I could keep track of my progress, and that was when it occurred to me just how big a number 90 was and how many blank spaces were on that sheet. It was an intimidating moment, but I adopted a solid “one video at a time” attitude and got right to work to have a few in the can before the 90 days began.

I decided to set a standard for myself—the videos had to be decent. I had no illusions of their perfection or professionalism, because I am neither when it comes to playing guitar. Still, I at least wanted to show my respect for the instrument and make each video as compelling as I could with the tools I had available. That meant using backing tracks when possible, and click tracks when not. It meant using the right guitar and the right pedals to get the tone as accurate to the record as I knew how.

I had hoped to soar into October 1 with 10-plus completed and ready-to-upload videos. That’s not what happened. I had grossly underestimated how many tries it would take to nail each song on camera. So by day one I had only four videos done. Four. Out of 90.

Nevertheless, I was really proud of that first one, so at midnight on October 1, I posted it. And believe it or not, from that point forward a new guitar video was posted every day for 90 days.

The Good

When I first said I was going to do this, 90 days didn’t seem long. After all, three months is not much time in the grand scheme of things. But 90 songs is a lot of songs, and it very quickly became clear I was going to be forced out of my comfort zone, learning songs I’d never considered learning before. In terms of becoming a better and more versatile player, that was the best thing that came out of this project. Before, I would have never tried learning songs by Metallica, Smashing Pumpkins or Red Hot Chili Peppers. I would have said, “I’m not cool enough to pull that off.” And for the record, I’m not saying I did pull it off. But I tried, which was progress enough.

I also set a quality standard early on that I didn’t want to lose. Again, I’m not saying that all (or any) of the videos are perfect. But in most of them, I’m at least landing the notes, which was no easy feat. Some of the songs took several days to nail down—days I really didn’t have, given that by midnight each night, I had to post something. So I got better at learning quickly. The pressure of public accountability kicked my brain into high gear and pushed me to continue reaching for interesting and iconic guitar songs, regardless of whether or not they’d be easy to learn.

At the same time, as much as I wanted each video to be as good as I could make it, I had to learn to let go, too. Some of them never made it past the work-in-progress phase, and I went ahead and posted them that way. At first, I was self-conscious about it, but then I remembered I have never claimed to be anything other than a guitar student. It’s OK (and even inspiring) to get vulnerable and show your work sometimes. Plus, I quickly realized every video would be replaced by a new one in a matter of hours. There was no time to dwell on any of them, even the ones I was most proud of.

The best part—and this I could have never predicted—was that people were really into it. Right from the start, I had a ton of support. People found out what I was doing and reached out to send me song requests, to ask about gear, to tell me their own stories about learning guitar, and to generally cheer me on. By the time I hit the end of 90 days, I had made a solid group of like-minded guitar friends on Instagram. There have even been a few people who have launched similar song-a-day projects of their own, which has been inspiring to watch.

The Bad

After all that positivity, I don’t want to be a downer, but in case you’re thinking about taking on a similar project, I want you to know what you’re getting into so you can be prepared. Like I said at the start of this column, nothing was easy, and I would hate for you to be blindsided.

First of all, the time commitment was brutal. Because I went into it with so few completed videos, I had very little leeway for rest days, sick days, travel or anything else unexpected. Knowing I had to put something out every single day was exhausting. On average, each video took two to three hours to create. Occasionally I got lucky and nailed something down in 15-30 minutes, but a handful of them took six hours or more. If I hadn’t been working from home at the time, it would have been impossible.

Also, I know I’ve said this already, but 90 is a big number. Around day 65, I hit the wall hard. At that point, had it not been for all the encouragement from people, I would have stopped. Just, “Whoops, I bit off more than I could chew.” Boom. Done. But any time I expressed even a hint of fatigue or despair, someone unexpected would send me a message of reassurance, which motivated me to do one more. And one more. Until I got to day 90.

Finally, with 13 days to go, I went on a cross-country road trip I absolutely did not plan for—amazing in its own right, but not for 90-in-90 accountability purposes. Since I didn’t have a ready supply of extra videos, I had to record on the road. I brought my acoustic guitar along and recorded in hotel rooms and cars, often at absurd hours. That part was stressful and not a lot of fun. It worked out (and forced me to work my acoustic chops!), but I do not recommend putting yourself in a similar position.

The Aftermath

Project 90-in-90 changed everything about how I approach learning guitar. One of the biggest hurdles I’ve faced since the very beginning is anxiety, especially when it comes to playing with or in front of others. I’ll cover that topic more in-depth in the future, but suffice to say it had become almost insurmountable before this project. The confidence I gained from learning a song every day and putting it out into the world has helped me more than I can say.

I’ve also started taking myself more seriously as a musician, in the sense that I now feel like I have a voice among the thousands upon thousands of guitar players in the world. I’ll never be the best player, and I’m not trying to be. But it turns out the love I have for playing speaks volumes to others, even to players with decades more experience than I have.

Looking back, I’ll be the first to admit how it was an overly ambitious undertaking for my skill level at the time. Still, I’m glad I did it. People have already started to ask if I’m going to do it again at the end of this year. Never say never, but I doubt it. Right now, I’m working on learning entire songs, or writing my own parts to songs and trying to make them as perfect as I can. Project 90-in-90 was about learning quickly; now my focus is on learning well.

That said, if you want to try it, you have my support! Reach out to me on Instagram and we’ll talk.

This Month

Student challenge: Try to learn something new every day for a period of time. It doesn’t have to be a whole song, and it doesn’t have to be for 90 days, but see if you can do it for a week or two. Don’t put any limits on yourself in terms of style or skill level. Push yourself.

Inspiring guitar player: Tyler Bryant (find him on Instagram at @thetylerbryant). He posts a ton of videos and is entirely unafraid to put on a jam track and wail on it. His tones and note choices blow me away every time.

Tunes I’m working on: “Voodoo Child” by Jimi Hendrix. Or Stevie Ray Vaughan. I’m working to come up with some version of it that does justice to both artists. I’m also still plugging away at the National Anthem. That gig is coming up soon and I am more nervous than I’d like to admit.


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