I am well over halfway through my vacation time that I dedicated to writing a screenplay.

Week one I spent completing some loose ends in the research department.

Week two I spent outlining with reckless abandon.

While I am very pleased with my progress thus far I experienced a emotional set-back in week three and only have a handful of scattered scenes written. Not exactly where I wanted to be but I am still putting work into the project every single day. For which I am proud of myself for keeping up the commitment.

It was not my intention to finish this screenplay in a month, to be clear. If that happens: superb (of course, it’ll need an immense about of rewrites, review, and revising). My definition of success for this month is: working on the screenplay every day with the milestone of having a detailed outline completed as the artifact of that work.

I’ve never written a feature film screenplay before. I am prone to overthinking big tasks and unwittingly overwhelming myself in the rough seas of self-doubt. Occasionally, I even catastrophize enough that I quit before I begin utterly convinced of my own failure thus the self-fulfilling prophecy. By not starting I am that failure I so clearly visualized.

Self-doubt is like a curse that you need to dispel. Unfortunately, it takes a lot more persistence, patience, and effort than just waving a wand, drinking a curative elixir, or praying it away. Without diving into my personal experience and management of my ebbing and flowing confidence, or lack thereof, I’ll share my steps for trying something new, challenging, and scary.

Generally speaking this is how I complete anything:

1. It’s OK to suck at things at first. In fact, it’s very normal to suck at things at first. Starting one step at a time is the best way to stop sucking at something, eventually.
2. Perspective. Break a big tasks down into its very smallest parts. One big task may seem insurmountable but dozens of small tasks are more manageable. Cognitive stacking, building walls of tasks all around yourself, can make you feel helpless and trapped in the face of a monolithic project. Spread those tasks out with a schedule and breakdown those barriers into their component parts by setting smaller goals. I also derive a lot of satisfaction from vandalizing my beautifully colour-coded to-do lists with checks, symbols, and Xs. Find the method that gives you some pleasure and sense of accomplishment each tiny step of the way.
3. Be realistic. Set expectations that you know you have the time, energy, and space to achieve. Find the balance between pushing yourself towards completion without overburdening yourself.
4. Check in with yourself, review your progress, and adjust as needed. Plans change all the time. It’s wise to course-correct as you learn. If something isn’t working don’t force it. Set new goals knowing what you know now. Keep on going.
5. Celebrate you progress. This is an important step. I like to incentivize myself with rewards for completing a significant portion of the project. These rewards should be personal, uplifting, simple or meaningful, and truly a indulgence.

More specifically this is my road map for working on the screenplay everyday with the goal of achieving that robust outline:

1. Inspiration/mood board.
2. Character inspiration. Focus on visualizing this character and how they embody their characteristics.
3. Character biographies. Focus on their personality and emotions.
4. Theme. Define it and tie it to each of the characters, locations, and major plot points.
5. Conflict & the main characters external arc.
6. The main character’s internal arc.
7. Atmosphere, mood, and visualize the film. Extrapolate from your inspiration board. Describe what you see, hear, feel, and smell.
8. Locations.
9. Potential scenes. I suspend judgement, grab a stack of 100 index cards, and just keep the pen moving and scrawling ideas until I run out of cards.
10. Outline. Sort your potential scenes, identify the conflict, the turning point, and beats within the scene.
11. Write. Complete a scene or sequence (a group of scenes) a day.

I am in the midst of number eleven and I am finding it very difficult. Rather than tethering myself to writing linearly I am hopscotching between scenes, acts, and beats. It does feel liberating but it also makes tracking progress obscure, which I don’t like just because of how I am wired. I deeply desire to see clear straight forward progress. Writing unfettered and without a deadline I am, despite the oxymoron, forcing myself to be reckless and free.

This self enforced freedom is a new sensation. I may even admit that it is probably a healthy practice for my rigidly methodical self. I learning to trust my intuition, be guided by my feelings more than my to-do list, and most importantly stop berating myself for not doing something “right”.

When I feel stuck I rewind to my mood board, I revisit the theme, I read my character’s bio and imagine speaking with her, I listen to the playlist of music I created for the project, or I write down even more potential scenes. I let myself live in those moments of planning and inspiration without getting upset with myself for not strictly “writing”.

From my point of view all of these activities are writing. Even if I am laying on the floor in a dark basement listening to Bobby Gentry.