8 Lessons From My 28 Day Song Challenge

The sun was already up, I was barely awake, and my voice had given up on me – but I was still grinning from ear to ear as I hit the “upload” button. It was 6am, February 28th, and I had officially completed my insane 28 Day Song Challenge.

I’ve never made a song before. Never played with Logic Pro. Hell, I even had issues about showing others my creative work. But here we are, 28 days and 28 songs later. It was definitely one of the toughest months in recent memory – trying to move out of an apartment, finish two video projects, letting my health and social life down a hole, all while posting up a song a day. But this has been of my proudest and most rewarding months ever: it threw music back into my life 100%, taught me tons about songwriting and beat production, proved to myself that I still got that willpower, and got me creatively engaged in a way that I haven’t felt in over 8 years!

You can check out all the songs on my Youtube channel and although they’re not all winners, just know that those songs represent a monumental month in my life. And without further ado, let me share some of the things I learned in that month:

1) Singletask, Don’t Multitask

I’m the kind of guy who wants to and thinks I can do it all. Well this challenge forced me to confront reality: if you try to do everything, you will only make little progress in everything. If you want to make a lot of progress, you need to focus a lot of time and energy into just one goal.

To make a song a day happen, I had to clear 5-8 hours a day (especially in the beginning), which means my normal sleeping, working out, eating, social, and productivity routines all got thrown out the window. Obviously I’ll want to find a better balance in the future, but I realize that I wouldn’t have learned and grown nearly as much if I hadn’t focused my entire life around this music challenge.

2) There is No Greater High Than That of Creation

An amazing thing happened while creating these songs: hours would melt away, I’d spend all day itching to get back into the “studio”, and many nights I couldn’t sleep because I was buzzing with the excitement of just finishing a song.

This pure creative energy was absolute amazing. I hadn’t felt like this since back in early high school, when I first started learning about filmmaking. The high you get off of creating something where there was nothing just can’t be compared to anything else. A big part of this was achieving that highly sought after state of creative flow, where you completely get lost in your work, but I’ll talk more about that in a future blog post.

3) Don’t Try to Go It Alone

Making the challenge public was quite possibly the smartest thing I did.

It kept me accountable. Since I told the world I’d be doing this challenge and was uploading the songs every day, I knew that if I skipped a day I’d be facing public failure. And let me tell you, that’s one hell of a motivator!

It made me work harder. Knowing that other people were going to hear these songs, I suddenly felt the pressure to elevate the quality of each track. I couldn’t just phone it in. Every single song, I pushed myself to do my best and make it something I could be proud of (or at least not completely embarrassed of) showing to others.

I felt supported. I’m not gonna lie, there were many days where this challenge was downright grueling and made me want to give up. And I probably would have if I just kept this challenge private. But over the 28 days, I got so much love and support from friends, family, and even random internet people. That was crucial. My friend in Berlin even made a remix to one of my songs! Thank to everyone who gave me a shoutout – you have no idea how much that meant to me.

And speaking of other people…

4) Connect With Other Like-Minded People

No matter what you’re doing, whether it’s starting a business or learning a new hobby, connecting with others who share the same goals is absolutely crucial. For me, one of the best things about making this challenge public was that it put me in touch with other people who loved making music too (such as Otavio and BC).

Not only was it fun as hell to collaborate with friends, it also accelerated my learning process tenfold. I got to see the workflow of different artists, they taught me useful tips and tricks, and got me to try different ideas that I wouldn’t have done on my own. It was also great to have others to just talk music with and answer random questions I’d have. And did I mention that it’s fun as hell?

5) If It Makes You Uncomfortable, Do It

I’m notoriously self-conscious when it comes to my creative work. I often shy away from sharing my work with others and worry too much about what people will think. This challenge helped me push past that. You don’t really have time to be self-conscious when you have to pump out a song every single day.

With my first few songs, I was so nervous about putting them online. You can hear in my intros how apologetic I am and undeserving I felt of sharing my creativity. But by the end of the 28 days, I had pretty much gotten over that fear. Creativity is meant to be shared with others. Even if it’s not perfect. Especially if it’s not perfect. How do you expect to get any better if you never receive any feedback?

If doing something is difficult or makes you uncomfortable, it means you’re pushing past your boundaries. You’re leaving the territory you’re familiar with and taking in new experiences and challenges. Don’t get it wrong: this is the only way to grow. So embrace that discomfort. Keep pushing past the uncomfortable, and eventually it’ll become comfortable.

6) Setting a Detailed Plan is 90% of Accomplishing the Goal

No matter what kind of goal you have, take some time to think very carefully about your plan to accomplish it. Do this before you start. Setting your plan is the absolute most important step of accomplishing a goal.

For example, let’s say you want to write a 200 page book in 1 month. That’s a pretty daunting challenge with a good chance you won’t follow through. But let’s say you set a detailed plan for yourself:

– every day you’ll write 7 pages
– the writing can be in a rough stage because you’ll edit it later
– every Sunday you’ll meet with a friend to get feedback as you progress.
– as often as possible, you’ll do the writing first thing in the morning to get it out of the way and start your day strong.

Now the challenge doesn’t seem as daunting does it? There’s no more thinking required. No making excuses. No letting time slip and realizing on the last week that you’re way behind. If you take your time to think through every single aspect before you start, you can focus 100% on just “doing” and you’re practically guaranteed success.

This works for everything including workout goals, health diets, and yes, music challenges. Other aspects to consider when planning is level of difficulty (push yourself but not too much), planned flexibility, and assessing and changing your plan as you progress. I’ll go into all this and more in a future blog post.

7) Being a Perfectionist Kills Creativity

One thing I’ve always struggled with is my need to be a perfectionist about my work. This has its good sides, as I always set a high bar for myself. But at the same time, I also set myself up for constant disappointment because let’s face it – nothing you make will ever be “perfect”.

One unintended benefit of this music challenge was that it allowed me to let go of that perfectionist in me (well, mostly). I was able to lower my expectations since I knew other people would understand if my songs weren’t polished – they knew I was making a song every day without any prior experience. This let me off the hook and allowed me to just play and have fun. Surprisingly, that’s something I haven’t been able to do with my creative projects in years.

It also gave me the idea to experiment more with separating my creative processes. When working on a project, the analytical/logical side of me (left brain) is always looking over the shoulder of my creative side (right brain), constantly judging and questioning every single move it makes. I want to try giving my creative side more freedom to do its thing without any interference and then bring in my analytical side later to judge what I’ve started and figure out how to improve it. Easier said then done, I know, but I think this could open up huge doors for me creatively. I’ll keep you updated.

8) I Respect Other Artists and Music So Much More

After trying to create songs and lay down vocals of my own, I have nothing but the utmost respect for other artists now. I always thought that singing and recording a decent take would be pretty easy. Um, no. That microphone puts your voice under a microscope and picks up every little detail, every semi-flat note.

And aside from the notes you sing, I realized that how you sing them is just as important. I discovered that you can really push your voice in so many different ways. Listening to songs now, I can’t help but admire the vocal stylings that each artist has carved for themselves – and yes, that includes every artist on mainstream radio too. For example, I love Kanye but wasn’t a huge fan of his voice, but now I hear all the character he throws into it and the way he plays with the words (in Forever, how he says “Benjamin Button, what? Nothin”) and I respect the skill behind that. Even Britney Spears. Everyone likes to talk about how she can’t sing. Maybe she can’t. But can you imagine Christina Aguilera trying to do Britney’s sexy growl? Nope. Britney’s got a vocal styling that’s all hers and she owns it.

And as far as music itself, I’m more in in love with it than I thought I could be. I guess I never gave enough time to it but now it’s a priority in my life. Wherever I am, whether at a coffee shop or a bar, I notice the music first. I try to only listen to music on my nice studio headphones. And I feel like I appreciate all kinds of music even more now, finding something to like about everything.

So What’s Next?

I want music to continue to become a bigger, more constant part of my life. I want to keep making music and keep learning more. I’m really looking forward to taking more time with songs. I’ve learned how to throw together a song quickly, but now I want to take the time to try new things and learn techniques without rushing. And at the same time, I definitely want more of a normal balance with the rest of my life.

I want to keep setting some sort of daily goal for myself so I don’t completely drop the momentum I gained. I’ll set a goal to spend at least 30 minutes a day exploring music in two areas: 1) continue learning how to produce songs, and 2) learn piano and music theory.

I also want to try and find a vocal style that fits me. Over the 28 Days, I tried to push my voice in all different ways – from a raspy Mike Posner-ish croon, to a bouncy, higher-pitched Lil Wayne flow. I want to find my voice and make it my own.

I want to continue to destroy the perfectionist in me and separate my left and right brain creativity. I want this to carry over into all the creative things I do.

And finally, I want to change the focus of my blog/website. In the next few weeks, I’ll be launching a separate site for my film business and want to make this blog more focused on personal topics. I’ll write blog posts once a week on everything from music, to travel, to personal productivity. Sharing this music challenge with the online world really helped me – now I want to put more of myself and my thoughts out there on a constant basis, see how it can help the other areas of my life. That’s what I want to use this blog for.

And this’ll definitely help me in one area: to put it bluntly, I think my writing really sucks and I’ve always felt self-conscious about it. I want to do the same thing I did with my fear of creating songs and do it with writing. So get ready y’all, a blog post will be coming at you once a week! Can’t wait to see what I learn from this challenge.

###

In other news, right now I’m living in Medellin, Colombia, with a guitar-playing Colombian family and taking private salsa dancing lessons! My high school Spanish is finally being put to the test and I’ve been shocked at how well I can communicate with a handful of words and lots of finger pointing (no seriously, I’ve told entire 10 minute stories this way).

I’m trying to do this trip a little differently from my past month-long travels, where I basically just checked out on vacation. This time I’m actually trying to be productive too: working on two video projects, prepping my new company website, continue learning about music, working out 3 times a week, and all while trying to experience a new culture. Like everything else in my life, it’s just another challenge, another experiment. But if I can pull this off here and accomplish that perfect productivity/life balance, I’ll be able to do it anywhere. Wish me luck!