Uncertainty is not the Enemey

Advice for people who often start cool projects but rarely get through them.

Intro / The Monster

I’ve got a question for you - what do the following thoughts have in common?

• “Before working on anything, I must create a business plan to know what to worry about later.”
• “When should I post this video? What day of the week? What time? If I can figure out the best time and day to post, I’ll totally get more views.”
• “The best thing for me to do next is sit down and write about the best thing to do next.”
• “We need a meeting to plan our meetings for next quarter to ensure we have time for feature design meetings to plan out what we need to build to deliver those features to our clients.” That last one might be a bit on the nose for anyone who has worked corporate, but do you see a pattern here?¹

Questions like these have often held me back in creative and professional pursuits. As soon as I get through the first bit of exciting work, these questions come streaming into my mind. Unfortunately, the longer they’re in my head, the harder it becomes to motivate myself to work on the project.

It feels like a little monster occasionally pops up on my shoulder and begins asking all the “important questions.

Actually, I like that. Let’s name it. I’ll call it “The Monster.”

The Monster is always around - lurking behind every deadline, project, and creative idea. So when I decide to write about something, The Monster pipes up and says shit like:

Or - god forbid - I have some cool project or business idea:

The little pipsqueak is insufferable and virtually impossible to ignore.

Worse yet, The Monster’s arguments are often compelling. After all, if I’m going to put a ton of time and effort into something (like possibly years of my life), I need to have a pretty damn good reason for doing that. It’s irresponsible to charge forward on something without doing at least a little bit of homework beforehand, right? And if it makes sense to do some homework, shouldn’t we do all of it?

Inevitably, The Monster wins, and (assuming we don’t give up immediately) we pull out a piece of paper, a planner, or a blank doc and start trying to do the work that The Monster assigned us.

Usually, it starts out pretty easy…

And then, suddenly, the homework will morph into a set of impossible questions that has nothing to do with your initial task.

On the best days, The Monster distracts us from our work. On the worst days, The Monster makes us doubt ourselves and our abilities and trivialize the things that we create.

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The Monster is a Dirty Liar

There are two opposing forces at play in our minds. They’re kinda like “motivation” and “difficulty,” but they’re also not at all like “motivation” and “difficulty.”

Let’s ditch the baggage and start with a clean slate: I’ll call them “Fuel” and “Friction.”

Without friction, fuels drive us toward action:

• We seek food if we have the “hunger” fuel source.
• We read and write poetry if we have the “curiosity and interest in poetry” fuel source.
• We do our taxes if we have the “I don’t want the IRS to put a warrant out for my arrest” fuel source.²

Let’s pretend you’re starting a new Big Creative Project. You’re super duper excited about the project and have already started researching, sketching, coding, or whatever your Big Creative Project requires.

Things are pretty effortless in the beginning. You’re probably doing the activity you enjoy most regarding your Big Creative Project. That means you’ve got a ton of “curiosity and interest” fuel to push you forward, and since you’re working on the stuff you enjoy working on, you’ve got very little friction.

This is it! This is where The Monster comes in! The Monster is good at playing mind games ³ , and it has figured out how to manipulate our fuel sources and sense of friction to influence our behaviors.

When failing a task doesn’t have consequences, The Monster gladly gives us an excuse so that we don’t have to do the work in the first place. We get to carry on with our lives (and egos) intact, even if the course of action would have resulted in failure.

A big downside, though - burning that extra-special fuel makes us feel downright awful.

If you think about the world from The Monster’s perspective, the situation becomes pretty clear - The Monster is just trying to protect us. It makes sure that we’ll be okay if something in the future might try and hurt us.

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Yeah, yeah, yeah. I get it. Even though The Monster has good intentions, its actions are damaging.

If we want to live happier, healthier, more productive lives, we must do something about the monster.

We can stare at The Monster.

Not literally, of course. There’s no actual monster to stare at. However, we can improve our awareness of when and how the monster messes with our fuel sources.

Let’s force the monster to come out into the light. From there, we can examine how it affects our thoughts and feelings.

Here’s How

1. Get some paper and something to write with. ⁴
2. Think of a project or task or something that you’ve been working on - we’ll call it your “struggle-project.” I’ll give you extra brownie points if the project is something you’ve been procrastinating or avoiding.
3. Answer the following questions:

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If you’re still here - hooray!

Assuming you did the exercise while focusing on your struggle-project, your monster might be actively throwing a fit.

Ask yourself - is The Monster adding extra-special (dirty) fuel to your engine so you’ll work harder? Or is it making the project seem impossible and providing excuses so you don’t feel bad about not working on your struggle-project?

1. Extra-Special Fuel: Are you having anxious thoughts or feelings of ambition, making it easier to push through difficulty? Do any of the following thoughts resonate with you?

2. Fake Friction: Is The Monster making your struggle-project seem impossible? Or maybe it’s making your struggle-project seem trivial and not worth the effort? These feelings usually manifest as tiredness or boredom with your project.

Sit with the feeling for a moment. Don’t try to change, run from, or otherwise suppress it. Just observe it. ⁵ After a while, the feeling should diminish a bit. ⁶

When you’re ready, review what you wrote earlier. As you read, notice which parts make The Monster return to the surface. Why?

Try to understand the insecurity that The Monster is protecting you from. This will be difficult at first, but it gets easier with time. Sometimes all you have to do is flip the feeling on its head; if you’re anxious, ask yourself what you’re anxious about. If you’re tired, ask yourself why. ⁷

The funny thing about our insecurities is that they lose their power once we know what they are. Right now, I’m afraid to publish this article because I mistakenly derive my own value from the value of what I produce. Ergo, I have no value if no one finds any value in this article. Simply knowing that and being able to observe my own insecurity takes its power away.

Next time you work on one of your struggle-projects, notice when The Monster gets involved. Ask why it’s making you feel that way. Consider journaling about it. Then decide what to do next without letting The Monster take over.

Footnotes

1. If the questions seem perfectly reasonable, then you are precisely the target audience for this article. Read on. ↩

2. I’m still nostalgic for the time when I was curious and interested in doing my taxes the first time around. Novelty is a powerful drug. ↩

3. In fact, it’s just as good at playing mind games as you are because - fun fact - you’re the monster. It’s you. ↩

4. Or a whiteboard, a journal, a word doc, a sharpie and the decommissioned body of a 737 MAX. Whatever floats your boat. ↩

5. For brownie points, use the paper (or decommissioned 737 MAX) from earlier to write down what you’re feeling. Next time you’re working on your project, review what you wrote and reflect on it. ↩

6. Maybe do some box breathing while you’re here. ↩

7. Tiredness is an emotion and a physical thing! It’s both! The monster takes advantage of tiredness by making you feel like your struggle-project isn’t worth doing & won’t be worth the effort. ↩