#24 - The Value of Occasionally Trashing Your Own Plans (& lessons from my failed music career)
Steps you can take to increase the chance that your plans will work out, and a story about my failed career in music (with a link to some of it!)
On the value of occasionally trashing your own plans (three tactics)
“Ahhhhhhhhhhhh, yes. This… THIS is it.”
Do you ever get out of a brainstorming session feeling like this? It happens to me quite frequently. I’ll feel so good about progress made, and I’ll ride a wave of optimism into the night. Feeling corporate-world heroic.
This happened to me a couple of weeks ago, and then I got into my car, put on my podcast playlist, and of course I proceed to immediately hear something along the lines of “Ideas are great, but execution is everything.” You know, one of those uber popular ideas that seemingly every business guru loves to repeat at some point.
Screw staying at that level. Let’s go deeper.
If execution is “everything”, then how do you ensure that your execution plan is sound? I have a proposal: try to absolutely destroy your plan. I mean, absolutely trash it. Pick it apart, phase by phase, level-by-level and come up with all of the ways this thing could fail.
(If you don’t know this famous scene, please watch this video. Bless you, Office Space)
To spend so much time to come up with an idea, only for it to fail to live up to its potential because of poor execution sucks. Better to balance out optimism and “best case scenario” thinking with a dose of reality.
Here’s my guide to trashing your own plans (and hopefully helping to fix the weaknesses in whatever it is you’re planning):
Develop a project or initiative plan that lays out everything you need to do to make something happen. If doing this in a visual or gantt chart view is too difficult, just write bullet points / a numbered list
Go point by point and simply ask, “What needs to be true for this to go well?”
Pretend your project or initiative is a company. That company must succeed, and there’s competition. Ask yourself, “what weaknesses would a competitor exploit?”
If you can’t come up with at least three points or weaknesses, you probably are not being realistic enough and/or you may need someone else to come in and help you see the weak points
The value in this question is that it forces you to start thinking about all the ways something could not work out. It’s basically the exact opposite frame of thinking that one of my favorite books, The Alchemist, talks about, whereby the “universe conspires in order for you to achieve it.” Sometimes, going on any journey can actually feel like the universe is conspiring for you to not achieve something, and I oftentimes have found that the most fulfilling of journeys are those where you overcome the resistance
Lessons from my failed career in music
Let’s use this all in a real example: my music production business from when I was in high school —> college
Situation: I started to produce “beats” when I was about 12, and got progressively better and better to the point where I started to sell beats for more money than I could really ever make in any normal teenage summer job. I got good enough at it that I had a not-so-small stash of cash saved up going into college. At multiple points, I considered doing it as a career path, and did seriously explore it in college. My aspiration was to produce 5 albums in 10 years, and to have the recurring revenue stream from royalties fund my startup investing goals.
Outcome: I couldn’t figure out promotional and marketing channels quickly enough, and was eventually drowned out by the thousands of people who started producing EDM music in the early 2000s. I lost first-mover advantage, and I didn’t hustle enough to find people who actually knew how to do promotion, because I thought early momentum would just …magically lead to more momentum and interest
What went well:
My music production pace. I used to sit down and in the course of four hours have 3 different songs that would evolve significantly throughout each 4-5 minute song.
Epic sound. I never did light listening music; it was always something that would pour through your entire body (at least that’s how I felt! ;-)).
Following in the early days (had multiple songs hit 50k plus streams over the years, some of which can still be found here)
Self-learning: I taught myself how to integrate softwares, write light code, and operate multiple DAWs (digital audio workstations) with very high speed and efficiency
What went poorly:
I am not an audio engineer, and the audio quality of the music never consistently rose to the level that would’ve gotten more radio stations to play my music, and sponsors to utilize it in advertisements and films (…some got close, but most just didn’t hit the mark)
I was unable to pivot traction from my metal and rock bands in high school into a new audience in EDM. I stopped serving my core segment to try and chase another segment
After having a record deal offered in high school, I thought that other record labels would also come to my EDM-focused offering eventually, and they just never did. I was turned down probably 20 times, and instead of pushing through, I gave up
…In fairness, I was also — at that time — trying to keep my grades mega high to get into law school etc. etc. There was…limited time
My style wasn’t consistent enough. I bounced between different music styles (hip-hop beats, ambient, club-focused EDM) and struggled to pull it through into a consistent, unique sound
I didn’t invest enough in marketing, because I assumed “word-of-mouth” marketing would lead to traction which would lead to record label interest which would lead to distribution deals —> which would lead to more listeners —> etc. etc.
What marketing investments I did make had really crappy ROMI
Lack of consistency. I would put out mini albums on different platforms, rarely communicating regularly with my following at the time
Discouragement: some people loved what I created, some people didn’t, and as a younger kid (especially) dealing with rejection was hard
If I had simply applied my “trash your own plan” way of thinking to music production, things may have turned out differently. Maybe not enough to have it be my career, but I could’ve probably gotten farther than I did (I had enough feedback from audiences live + repeat traffic from my listener segment to know that I was slowly getting onto something).
If I had ran through my three tactics / questions, I likely would have landed on:
You need to invest time and $$$ to find an amazing, collaborative audio engineer, and even be willing to share in royalties with them
You need to spend more time on brand marketing, and hustling to reach out to event promoters, being willing to go on earlier than other artists, and even to take lower cuts of the overall night’s take just to get more exposure
You need to have a plan to engage your audience; don’t just “do it when you feel like it”
You need to do more listener tests with people who will give you tough feedback. Don’t just go to your friends who are going to say, “that’s pretty good!” …go to the friends who might say, “Dude, honestly, that last song was so bad it was an insult to the word ‘song’, and here’s why…”
Your other life obligations and priorities are likely to cut into the time needed to do all of this, so either: (1) stop DJing as much, (2) find an accountabili-buddy to help make sure you spend ample time on this every week, or (3) do not pursue this at all.
I can confidently tell you that I really wasn’t thinking through the above deeply enough, because I was afraid of having my baby (music) called ugly. The fear of rejection or not being positively reinforced crippled my ability to see glaring weaknesses in my plan, and my inability to get over it handicapped any chance I had (at that time) of a really successful music career. Sure, did I have fun? Hell yes I did. Did I make some money in the process? Totally. But did I achieve the plan I set out to in the beginning? No.
And sometimes you just have to go through something you work really, really hard at not panning out like you hoped. There are definitely lessons in that, and I also know that the above experience has made me more effective in my professional career (…turns out the complexity of music production is not so different than the complexity of system integration, which is where my career started…). But the takeaway here is that if something is important to you — if a project, an initiative, a bold bet… If you are deeply invested in it working out, you owe it to yourself and the people around you to spend more time considering how it could not work out.
A closing line from my journal in 2018
Which leads me to the last reminder I oftentimes anchor back to these days. It’s not an original idea, but I can’t remember where I heard it from. This is a direct pull from a journal I wrote to myself a few years ago.
“We wake up every day trying to achieve things. Some of these pursuits will work out, some of them won’t. These differentiated outcomes are a part of life, and failure is to be expected in the range of possibilities. But… if one must fail, it should be because you tried everything in your reasonable span of control to make it work. It should mean you thought deeply and tried deeply. Only then is failing/losing acceptable.”
-My journal from Winter of 2018
P.S. As I wrote this, I immediately saw images of hundreds upon hundreds upon hundreds of hours learning how to create art. The failure I wrote about wasn’t just some light, not-serious thing. I actually thought that it could have been my lifelong career. I visualized it. I was antisocial for a long time because of my devotion to it, and the pursuit helped me get through some pretty awful experiences in life. It was important that it would have worked out, and though I can look back on it now with acceptance, it sucked to pour thousands of hours into something, only to have it not work out. I’ve learned some great lessons from the experience, and I hope it helps you uncover even ONE thing that could tank something important to you, so that you might find a way to increase your chance of achieving whatever it is that you want to.