Creatively Unblock Yourself with Two Questions

Most of us know that one of our most significant problems is ourselves. While many trials and difficulties we face in life are legitimately hard, there are those of us (like me) who excel in mentally catastrophizing. We think of all the potential options of how things can get hard or go wrong in our heads, and at the end of that road we can easily find hopelessness and despair.


These things are legitimately difficult

But what if there were a different way to think about hard things? What if all hard things could be considered easier? Today we’re going to cover two important questions you can ask yourself when you feel “blocked” for any reason – stress, overwork, catastrophizing, etc.

  1. What if it were easy?
  2. What if it were fun?

What if it were easy?
This question in relation to hard tasks comes from Tim Ferris, who has brought it up on numerous podcasts and other interviews. The gist of the idea is, when facing a difficult task, you should ask this question to simplify your work and pair it down to its most important details.

Asking this question forces you to recognize that we often “scope bloat” and overcomplicate our own ideas for the sake of perfection. If you wanted to start a podcast – you might start thinking of getting new audio equipment, finding the “perfect” intro song, etc. In reality, these things don’t need to be blockers and can instead be part of an ongoing development of the project. Same can be said for demo reels, resumes, making new music, and any other creative project.

– While this question can be misconstrued into “make a worse product” or “do less work”, that’s not actually the point. “What if this were easy” is really meant as a simplification for yourself. Maybe a demo reel or music project would be easy if you gave yourself permission to use only the things you already had, and not wait for the “perfect” moment or addition. You can always go back and add those things later.

What if it were fun?
In addition to Ferris’ question, I’ve come up with this one of my own. Much in the same vein as the first – this question is meant to be about simplification. However, instead of just figuring out what would make a project doable, this forces you to ask “within those constraints – what would make me very excited to work on this?”

I find this is a very helpful question for me to ask immediately after trying to simplify a project. While I can streamline something I’m doing, it often doesn’t make me more enthused to work on a project. Asking this of myself changes that.

As an example – when working on the upcoming audio versions of previous “Micro-Guides” on Clarity and Impostor Syndrome, I became overwhelmed by the thought of creating music to add to the projects. I could both simplify that and make it fun by discovering music that others had recorded, using that music, and learning more about/promoting those artists. Because I like collaborating and sharing other people’s work – the process went from dreadful to think about, to overwhelmingly fun for me.

“But… dude my project needs to be perfect and you don’t understand… nobody will care or hire me if it isn’t perfection. It HAS to have this one magic thing that’s really hard to pull off!
You may be right, I can’t tell you for sure. But, what I can tell you is that exhaustion, despair, overwhelm, and mental anguish typically don’t get us closer to finishing our cool projects.

Typically, the things that we focus on and believe are of core importance go overlooked by consumers of our work. Obviously, that isn’t always 100% true – but how many stories have you heard a musician you like lament that one of their favorite songs isn’t really a fan favorite? This sort of thing happens all the time. It doesn’t mean we shouldn’t pursue personal fulfillment, but, I’d argue that asking yourself these questions can be useful more often than not.

And you’re always free to choose to make things complex anyway!

Okay so again, those two questions were:

  1. What if it were easy?
  2. What if it were fun?

One last thing to remember…
Most of us got into artistic work because it was fun and easy. One of my favorite quotes of all time comes from the movie “Sound City”. In it, Dave Grohl of Foo Fighters is having a blast jamming on a song with Paul McCartney. The movie makes it look like they wrote a whole rock song in about 20 minutes.

At the end, Dave looks at Paul and asks “Man, why isn’t it always this easy?”. Paul looks back at Dave, smiles, and says “It is!.

I tend to think that Sir Paul is right!