An attempt to make a plan for my comedy aspirations, using Ray Dalio's five-step process for getting what you want from life.

I have a dream. I mentioned it in my first blog post, but I tucked it away in a footnote because I always feel awkward talking about it. I guess that's the first thing to fix, so here it is:

The dream: to run a production company that makes narrative comedy, uses a collaborative studio approach like Pixar, and is profitable enough to sustain itself.

This has been the dream for quite a while. I remember designing production logos – obviously the most important thing – when I was still in secondary school, over twelve years ago. I made a small burst of progress in 2013, when I registered the company – the second most important thing – and also co-wrote and produced my first (and currently only) webseries, Here All Week.1 But progress has been glacially slow since then, and the dream has stayed comfortably in the 'someday' column. I kept telling myself the comforting lie that I'm not ready yet, but in reality, I was probably clinging onto an imaginary dream to avoid the risk of it turning into a real and tangible failure.

But times have changed. I'm nearly eleven years into my twenties, and I've got a growing fear that we've only got like a decade or so of good Earth times left before everything implodes – and both of those things have made me realise that it's probably time for some forward momentum.

And so, I need a plan.

1 This was a lot of fun, and felt very cool. When I released it, I thought it was the most amazing thing ever, so I was surprised when people, while positive, didn't see it as the golden ticket to a comedy-writing career I thought it was. I watched it again recently, and I now understand why. But that's not a bad thing: the fact that I can think of dozens of ways to improve it means that I've got fractionally better at filmmaking, even if progress feels slow. I've long stopped sharing the link – especially after a castmember's agent told them to remove their credit, lest it damage their future prospects – but if you're curious, here it is.

The five-step process

As I also mentioned in that first post, I'm a big fan of Ray Dalio's Principles. So as a framework for this plan, I used his five-step process for 'getting what you want from life':

  1. Have clear goals
  2. Identify problems that stand in the way of you achieving those goals
  3. Accurately diagnose the problems to get at their root causes
  4. Design plans that will get you around them
  5. Do what's necessary to push these designs through to results

These seem pretty obvious when written down like this, and yet I'd never taken the time to think about my aspirations in this way. I've already got the first step down, so for the rest of this post – and the next one – I'm going to share my working as I went through steps 2-4.2 I hope it inspires you to work through them for your own audacious dreams – and if you've got the same one, then even better: you can try my plan out and let me know whether it actually works!

2 Full disclosure: I'm actually a little uneasy about publishing this. I finished the first draft at the end of December, when I was thinking about new year's resolutions – but it's taken me over a month to actually ship it. (This is also why I haven't quite hit my one-post-a-week resolution.) What if you think it's stupid? What if I've done it wrong? But I'm going to suck it up and embrace another one of Dalio's Principles: radical transparency. As he explains: "It can be difficult because [it] exposes one to criticism. It's natural to fear that. Yet if you don't put yourself out there with your radical transparency, you won't learn." This is a good point. If it is stupid or I have done it wrong, it's way better that someone points this out to me now, rather than me learning the hard way six months from now. Plus: I've already written this so it's too late anyway.

I've got three problems...

So what would stop me from waking up and living this dream tomorrow?

  • Problem 1: I have little experience with filmmaking.
  • Problem 2: No-one would watch anything we make.
  • Problem 3: I have no idea what a sustainable business model would look like.

Of course, these are not my only problems. Other immediately obvious ones include funding and finding people to work with – but these feel a lot more manageable. (We can start low budget; I can pester my many talented friends!) In comparison, the ones above are showstoppers.

So let's go through them one by one.

Problem 1: I have little experience with filmmaking

For someone who is keen to make films, I don't actually know that much about the art and craft of filmmaking. I guess it's because, until recently, I've been unclear about what exactly I wanted,3 and so I put most of my efforts into screenwriting – which was useful, but not quite the right path.

Previously, I would have tried to solve this problem by buying some books or signing up for some courses. Although these are helpful in moderation, I'm going to try following some more advice from James Clear's Atomic Habits, which talks about the difference between motion (planning and learning that doesn't actually produce a result) and action (behaviour that delivers an outcome):

Motion makes you feel like you’re getting things done. But really, you’re just preparing to get something done. When preparation becomes a form of procrastination, you need to change something. You don’t want to merely be planning. You want to be practicing.4

And so the better solution is:

  • Solution 1: Make a bunch of short films.

I know this seems really obvious when written down, but sometimes it's helpful to remind myself of the obvious things. So again, what would stop me from waking up and doing this tomorrow?

  • Problem 1.1: I don't know the practical basics.
  • Problem 1.2: I'm too much of a perfectionist.

Problem 1.1 is clearly a subset of my main problem. But that is referring to making good films, whereas this is referring to the specific problem of making films at all. If I turned up to a shoot, I would have no idea what to do. What setting should I use on my DSLR? How should I light the scene? Why is that red light on my sound recorder flashing? (And that's not even including all the unknown unknowns I'm completely oblivious to.) There are a few solutions, but I'm going for:

  • Solution 1.1: Invite myself to someone else's shoot so I can watch and learn.

This would give me a chance to learn the important stuff, while avoiding the black hole of books and courses I mentioned above. So if you're a filmmaker, expect a message from me soon...

Problem 1.2 is a bit more tricky. I've been building up to the idea of my 'first film' for ages: in the last five years, I've worked on several ideas for webseries and short films, but I've not pushed any of them through to completion. I'm bad enough with perfectionism at the best of times, but I can manage it with things like stand-up or blog posts: the cost of finishing those things is pretty low, and if I screw up, it's not long before I get another chance. But a film – even a short one – requires finalising a script, casting, rehearsals, production, post-production... which means if it's not the most amazing thing ever, then it'll feel like a massive waste of time. So the solution:

  • Solution 1.2: Reduce the time and money cost of making films.

My friend had a great solution to this: sketch comedy. Not only does this intersect with my comedy interests, but the cost of doing this – especially combined with a group of willing comedians and a Rodriguez list of things we have access to – is way lower than a short film or a webseries.5

I'm looking forward to starting this, but I've de-prioritised it for now. (The more observant of you may have noticed that there's no mention of it in my resolutions.) I'll get to it as soon as I can, but first, I want to focus on my second major problem – which I'll write about next time.

To be continued...

3 I know I wrote that 'this has been the dream for quite a while', but only vaguely and abstractly. It's only in the last six months or so that I've been able to articulate it clearly in a single sentence.

4 I realise the irony of writing this in a blog post that is entirely about planning, so don't bother pointing that out.

5 I'm especially drawn to the spirit of the YouTube channel 5 Second Films.

Header photo by Lucas Favre on Unsplash.