Principles on unstructured work, for ambitious people.

I’ve spent most of my career doing unstructured creative work; primarily in pre-product-market-fit startups, and also with theater and writing.

Unstructured creative work is most daunting when it’s unclear whether I’m moving in the right direction. And it turns out to be unclear most of the time. Success for creative work is poorly defined; at best it seems interminably very far away.

In lieu of being driven by success, I’ve learnt that I need to be driven by principles instead. I wrote these to help guide my days, keep me on track, and maintain morale.

Principle 1: Optimize for learning.

Each week, produce work that helps you get better at something.

Ideally, learn in the most practical way possible; learn by doing. Reading and listening to others is a useful complement, but the lessons often won’t be concrete enough.

Don’t over-analyze how useful the learnings might be. The utility of what you learn won’t be clear until much later (and even then, it will be useful in surprising ways).

If you end each week with a new skill, or deepened mastery of an existing one, that’s a win, and you’re on the right track.

Principle 2: Ship frequently.

Create work, and make sure it reaches other people. Ultimately, work is meant to serve others. So put it out into the world, and see what happens next.

Shipping is the only way to judge the quality of your work. So try to do it as frequently as you can. The best cadence differs based on the type of work, but anything longer than fortnightly can result in ruts.

Once work is being shipped frequently, try to increase impact each time you ship. Judge impact by breadth (number of people), multiplied by depth (impact per person).

If you couldn’t increase impact, see what went wrong. You’ll learn something, satisfy principle 1, and can be assured that the next time will be better.

Principle 3: Systems, over goals.

Outcome oriented goals are hard to set in an unstructured environment, because you often have no baselines to guide you. So the goals you set will either be too hard, or too easy.

If the goals are too hard, you’ll end up missing them, and it’ll be demoralizing. But you won’t know whether it was your goal, or your work, that was wrong. And if they’re too easy, you won’t end up learning, because you’re not challenging yourself.

Until the structure of your work becomes very clear, ignore goals. Instead, use systems that ensure you show up and do your best work everyday. That’s how Scott Adams, author of Dilbert, does his best work:

“A goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, its a system. If you’re waiting to achieve it someday in the future, it’s a goal…”

…”All I’m suggesting is that thinking of goals and systems as very different concepts has power. Goal-oriented people exist in a state of continuous presuccess failure at best, and permanent failure at worst if things never work out. Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn. The systems people are feeling good everytime they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.”

Scott Adams, How to fail at almost everything and still win big

Principle 4: Toys over trophies.

Treat unstructured work as play time, rather than an avenue for achievement.

In an unstructured environment, success is very hard to measure. So going for achievements won’t work. Instead, just try to have fun.

Fun means flow states, not mental junk food. If you’re worried about whether something is junk, look to principles 1 & 2. If you’re learning, and it’s impacting others, it’s likely not junk.

Fun can feel really scary for ambitious people. Us ambitious folks can often brute force our structured work work, putting in hard hours, to get a result. And while it might not be fun, the work is usually measurable, and will usually result in an achievement.

But brute forcing doesn’t work in an unstructured environment because it won’t be clear what you should be brute forcing. Plus, it’s not easy to measure the results, so it’s not clear when pr what you’ve achieved. So the mindset needs to change.

Try to make the mental shift from I gotta figure this out to I wonder what will happen. It’ll push you into a state of play, rather than a state of achieving.

Sometimes it can feel like fun is useless. But in practice, if you’re following the principles 1 and 2 of learning and shipping, it won’t be.

Principle 5: Doing beats thinking.

Avoid analysis-paralysis, by doing. Doing = Shipping + Learning. So if thinking is stopping you from doing, turn off the thinking.

Thinking is critical in structured environments, because there’s no end to the conveyor belt of work. You need to think carefully, prioritize, and do the optimal thing. But in an unstructured environment, you have to create your own conveyor belt. You’re more likely to be bored than to be overwhelmed. Suboptimality isn’t a big deal. So it’s better to think only a little, before doing.

It is extremely easy to find reasons not to do something: this is why analysis leads to paralysis. With creative work, thinking too much inevitably leads to ruts.

On the other hand, doing results in inspiration, new ideas, and a feeling of momentu, and accomplishment.

So don’t over think. Just do. The above principles, particularly 1 and 2, will stop you from going down the wrong path.

Principle 6: Follow the inspiration.

Cultivate curiosity, and let it take you where it takes you. Follow the loose threads that excite you.

It won’t be clear how the threads connect up in the future. But don’t stress out over it. As long as you are shipping often, and learning, just trust that they will.

Richard Feynmann spoke of this process in Surely You’re Joking Mr. Feynmann. Feynmann spent a bunch of time fooling around on fun (and seemingly useless) calculations about how a plate wobbles when thrown in the air. But that exploration eventually led to the discoveries that won him the Nobel Prize in Physics.

Principle 7: Taste will exceed ability

You’re likely to judge your first drafts against the final publishings of others. But your green work will likely not be as good as the practiced work of others. The gap can be demoralizing, and often stops us from putting our work out.

Try not to let it discourage you. Just know that it will take time before your taste can match your ability level.

Ira Glass, producer of This American Life, has a great quote about this:

“All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you.”

“… you gotta know it’s normal and the most important thing you can do is do a lot of work… It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions.”

Ira Glass

Principle 8: Growth mindset.

Remember that you will get better everyday at whatever you’re doing.

Carol Dweck’s book Mindset, talks about the difference between a fixed mindset and a growth mindset. Fixed mindset = the belief that abilities are set. Growth mindset = a belief that your abilities can grow.

Cultivate a growth mindset to help you overcome the taste-ability gap. Remember that your skills are malleable. If you follow your systems, you will grow. The things that seem hard today will become easier tomorrow, and you’ll achieve mastery eventually.

Principle 9: Reframe failures using compassion & trust.

Failure is what it feels like when you fall short of your ambitions.

And by that definition, you’re likely going to fail many times. Your ambitions are likely uncalibrated at the start. Your bar might be too high, especially if you have good taste. And your ability, as discussed above, is likely not at the level of your ambition yet.

So treat yourself with compassion and grace each time you fail. Don’t blame yourself, or disparage yourself.

In the game Dark Souls, death is an integral feature. After dying many times, players realize that dying is a part of the game, not something to be avoided. Dying is the only way you get better at Dark Souls. So it’s not failure to die – it’s a way to learn.

Similarly, remember that “failure” in the unstructured-world is a learning mechanism. Not necessarily a sign that everything is broken.

When you’re fully at peace with the “failures”, trust the process.

Remember that if it’s hard to define success, it’s hard to define failure too. So try to gently re-frame your work, away from success/failure, and instead to the process of learning and shipping. As long as you’re learning, and shipping, it’s working.

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