How to Finish What You Start

13 min readSep 1, 2023

The artist’s guide to becoming a world-class finisher.

Starting vs Finishing

Most artists are good starters. We are a seemingly endless source of spontaneous brilliance—at least on our best days. This is a great skill for anything where the distance between the idea and the output is nearly instant. But what about other work? What about the type of work that requires more than just an in-the-moment burst of interestingness? What about work that requires more than just a good start?

These past few weeks, like a lock turning into place and a bolt dropping away so that a door might suddenly swing open… I’ve realized the artist I want to become is not merely a prodigious starter of projects who excels in the moment, but a world-class finisher of extraordinary work. But how?

Don’t get me wrong, I’ve created much work and finished impressive projects and won accolades and attention. From the outside, I’m accomplished. But that’s just how others see me. I secretly know that there is much more that I’d like to accomplish than what I have. Every artist knows this. My list of started, but unfinished, projects is long.

You might have your own list. And while sometimes it’s important to let a project sit on the list until we are ready, other times the reasons a project remains unfinished are weak, counter-productive, or simply untrue. How do we change this?

How might we create (and finish) our own best work?

The Two Traps

To become a world-class finisher, you can’t just grind… then you are merely an impressive producer of lots of work. To get good at anything, you do indeed have to practice and put in an unreasonable amount of work, and the more the better, but it must be the right kind of work. Working hard on the wrong thing does its own special damage. You must be learning while working. You must grind with purpose.

If grinding alone is not enough, then neither is its opposite. The second trap that artists fall into is to incubate, ruminate, and nurture concepts, but never get them done. This path means you end up as a high-potential (but under-achieving) could-have-been who never finishes. No one wants to be a could-have-been. This last sentence stings the most for anyone who has ever started a project but somehow hasn’t yet finished it. Go ahead an re-read it a few times just to torture yourself a little bit. No one wants to be a could-have-been who never finishes. This is the dread we work against.

So let’s get to work.

These two traps are devastatingly familiar to artists. We have all sensed both possibilities: being either the prodigious producer of garbage or the never-got-there-wannabe. These two deathtraps haunt us; ever present, ever potent. Always just around the corner.

So how do we defeat both extremes, without becoming some sort of perpetual compromise?

The Answer is Language.

Language! We can use language to rewire our brains to become the artists we want to be. The right words can give us a rule around which to make decisions and guide our creative endeavors.

Just as the right mission statement can guide a product team, or the right rallying cry can drive inactive voters to the polls, or the right perfectly-felt-and-spoken whisper can warm the heart of your beloved, words can help our brains transform our approach to art so that we become world-class finishers.

But which words?

To figure this out, I needed help.

I reached out to trusted friends: authors, artists, designers, CEOs, investors, Oscar-winners, and an arctic explorer. From each, I got feedback on different parts of the problem. From the designers, I got feedback on the productivity and efficiency side of the problem. Writers gave me great feedback on the nature of structure, revisions, and endurance (as well as deep empathetic howls). From all I got feedback on the transformative power of deadlines. Together we even coined a phrase, deadlines = lifelines. And from the arctic explorer? I received a touching and personal response that helped me understand that drive is always both universal and personal.

With pieces of the puzzle in hand I started sifting through all the parts to see how the mechanisms might all line up. The phrase I was after needed to combine the two halves of the problem (deep, curiosity and creativity vs. relentless work and grind) in a way that was more than just two seemingly opposing things stuck together.

And then, like the final twist of a Rubik’s cube, there it was…

Creative Diligence.

The two-word key I needed to unlock my brain was “Creative Diligence.”

Creative emphasizes the action of art. You must create, not merely sit or hope. Diligence does several types of work at once: it represents the idea of grinding and productivity (being diligent); it represents the idea of being exact and excellent and conscientious (not sloppy or weak or weak-minded) and it represents a special definition of diligence that comes from the world of investing, where you double-check all the numbers and do reference checks on all the people to make sure that everything that was presented as true is indeed actually true.

Putting this all together, we have our key:

Definition

Creative Diligence is the ability to combine radical curiosity and thoughtful rigor to solve creative problems and produce extraordinary art.

Let’s take this one chunk at a time:

Radical curiosity

We can’t be mildly curious and expect to do great work. We must investigate every aspect. We must explore seemingly unrelated ideas and have the willingness to sit in the state of not knowing long enough that we might actually figure something out, not just pretend to have a breakthrough.

Thoughtful Rigor

Thoughtful rigor is grinding with a strategy. We don’t just work, but work with a plan and a goal.

Solve Creative Problems

Creating a masterwork decomposes to solving problems. Seeing it this way — that as an artist you solve creative problems — removes the work from a validation of the self. It is not YOU who are the masterwork. The work emerges from you because you have the Creative Diligence to see it through, solving each sub-problem along the way.

Produce Extraordinary Art

We aren’t aiming for mediocre work or even very good work. Our goal is to create extraordinary work. It is this unreasonable ambition that makes it all worthwhile and that causes so much worry and consternation. But it is necessary. We are not here to do the minimum and move on. We are here to chase our curiosity all the way to revelation and bend the arc of humanity’s progress. We are here to create work that astounds and transforms. This is why we need Creative Diligence. The task is mighty. But we can get there. Every great novel, every marvelous painting, every mind-breaking movie, every psyche-restoring poem, every work of art that moves us is proof that someone, somewhere was able to do it.

And so can you, through your Creative Diligence.

Results

Creative Diligence. A two-word phrase. A six-syllable solve. Has it worked? Well, yes. For me, stunningly so.

Since getting the urge to solve this problem with language and then diligently creating a phrase, I’ve both been more productive (hitting my daily studio goals) and have created more in-depth work (having the courage to examine some of my faulty assumptions and skills), than before.

I shared the phrase back with the people I asked for help (all those artists and writers I mentioned earlier) and guess what… three have reported similar near-magical effects for their own work… suddenly being able to finish work that had vexed them. Unblocking, freeing, motivating, and inspiring. Not bad for two words.

You try it.

I want you to have the same marvelous, near-magical transformation. Try it! Take my two-word key and think of it as your own and put it to use to unlock your own brain. But check this out, to get the most of it, you might need a few guidelines to put it into action.

Practical and tactical.

Creative Diligence

Here are a few techniques to put Creative Diligence to work.

Say It Every Day

First, and most important, say some version of this phrase to yourself every day, several times a day.

“The reason I’ll succeed is my Creative Diligence”
“Every day I solve problems with my Creative Diligence”
“What separates me from others is not talent or luck, but my commitment to Creative Diligence”
“I run into problems all the time, but even when I get stuck, I’ve got a process of Creative Diligence that helps get me through”
“My Creative Diligence gives me a way to persevere and prevail even when I get stuck.”

Cite Creative Diligence as the Way to Solve Your Problems

When you talk to your friends about your problems, talk about how your Creative Diligence will help you succeed. Say things like: “I’m working on a character for a new story and I want her outer characteristics and her inner character to be in conflict, but I haven’t found the answer I’m happiest with yet. It’s been super interesting, however, to try on different possibilities and work through each one. I don’t have the answer yet, but I’m sure my creative diligence will pay off…”

Compare this to someone who isn’t equipped with the Creative Diligence mindset, that person would be tempted to say… “My character is flat. She had such great potential, but I’m stuck. Instead, I thought of a cool other thing I wanted to start…”

The Desire to Quit… Is Not Your True Desire

Imagine you are the hero in an adventure story, and that there are antagonists out there trying to thwart, stymie, frustrate, and destroy your good works… these enemies of creativity operate in the shadows, hidden, but are ever present. They speak in whispers only you can hear. Every effort they put forth is to try to prevent you from creating your great work. Now—with these antagonists in mind—whenever you want to quit a current project and go work on some new project… imagine to yourself that this desire didn’t come from you (you still very much want to finish your current project and bring it to its full potential and glory… ) instead the antagonists of your art never rest and they are trying to trick you by planting the idea of quitting or switching into your mind. Resist! O! Brave one! Resist!

Like the enchantment cast on Odysseus' men while visiting the island of the lotus eaters… which caused them to linger seemingly from their own desires and thus became imprisoned on the island… the desire you think you feel to quit your project and switch to something new is not your true desire, but an enchantment, an evil spell, cast by the antagonists to your great art. Resist! Wake mighty warrior of art! Call upon your Creative Diligence to defeat this untrue urge and harvest your project’s fullest potential and true worth!

The Da Vinci Technique.

Leonardo da Vinci left many projects unfinished for years, so you’d think he’d be a bad teaching example for the concept of Creative Diligence, but the opposite is true. He is our best example of the diligence part of Creative Diligence. When starting a project, he always first asked, “how does it work?” When he won a commission to create a giant sculpture of a horse, he first dissected a real horse to figure out how the muscles, tendons, and bones worked to balance, support, and propel the horse through its motions. He amassed a giant stockpile of understanding that he then deployed for his many different projects.

Here’s how to put this idea to work: If you run into trouble, instead of abandoning your project, ask yourself “how does it work? How does it really work?” and then have the guts to diligently investigate rather than just wave your hands and pretend to know.

If your drawings look misshapen or clumsy, deploy your Creative Diligence to figure out why… is the perspective off? Where is the light source? What muscles and bones are being used in this pose? What joints are being activated? What is their degree of rotation? Where does this muscle insert (connect) to this bone? What is hidden that I cannot see?

If your drawing is perfectly formed, but dull, sharpen your Creative Diligence to solve the problem… How can the facial expression, style of dress, pose, or setting change to augment my intentions? What happens if I move the “camera” and reframe this image? What matters to this image and how might I augment that feeling? What would I do to show the opposite of what I’m trying to say? And then what is the opposite of that? Can I take something away from this image to give it more power? Can I add a line or shadow so that we feel the weight of the character? How else has this problem been solved by other artists? How much do I want the viewer to know? What is the story behind the story and how might I emphasize this latent, hidden, deeper meaning?

The da Vinci technique works for writing as well. You can use it to decompose your character’s arcs of transformation, their complexities and tensions, as well as your choices—what are you saying vs. implying? How close to the character’s mindset are you letting the descriptive text become… what does the character know in this moment? What do we know (and what do we not yet know)? Which choices should be standard and which should be against type or radically new? When do you upend expectations and when do you embrace the quotidian? Which details matter? Which can be discarded?

Optimize Your To-Do List for Creative Diligence.

Take a look at your to-do list… not just your actual to-do list, but the secret one you keep in your head. Having goals such as “create masterwork” are absolutely paramount! but they make for in-actionable to-dos.

Instead, have the guts to break down your project into phases and create a list of questions (not answers) for each phase. Then rough out a timeline and get started working through each phase.

Practical advice: I use the FigJam app from Figma to plan projects. You can arrange digital stickie notes to create outlines, project plans, or anything else. I change the color of the stickies when they’re done. I bask in the glory of progress as I see stickies go from yellow to green. Below is a screenshot of my FigJam template for writing a screenplay.

Here is my FigJam template for writing a screenplay. It shows the three-act structure broken down into both a 5-Act overlay and a 7-Act overlay. The green stickies are the completed screens. The yellow stickies are the outlined scenes that have yet to be written. As you write each scene in FinalDraft, change the stickie from yellow to green and celebrate your Creative Diligence.

Hour of Power

Not every minute of your life is yours to use how you’d like. In the extreme, there are eras in your life when you have nearly no free minutes. It’s ok though, this doesn’t mean you’re no longer an artist. You can be away from your practice for a few days, weeks, or years, but once you are an artist, you’re never not one.

For the eras where you have at least a little time to give, here’s a slightly brutal suggestion: pick whatever time you normally get up, now choose a new time that is a little earlier. The difference between the two is your reverse time. This reverse time is the most wonderful gift to yourself. You’ve turned back time and given yourself 15 mins. 30 mins. an hour that you did not have before. Don’t waste this precious gift preparing elaborate coffee or scrolling through other people’s opinions. Instead, make this your Hour of Power. And to do that, you need to plan the night before.

Hour of Power — How to do it:

Before you go to bed, make a plan for what you’ll do in the morning when you turn back time. Eat healthy, drink water, get ready.
Get up early.
Execute like crazy during your Hour of Power.
Once it’s over, start your normal day.
Repeat.

Deadlines = Lifelines.

Sometimes it’s easier to produce if there is a force against which to act. A deadline can be that force. If someone gives you a deadline, celebrate. What a gift! It’s important to look at why deadlines help us. They cause us to fit a project into a fixed schedule, break down our progress into stages and next steps, and turn our focus away from pondering to producing.

If you do not have a deadline, make one up. Pick a date that feels just a little too tight and declare it your due date. Then pick a friend that you admire and tell that person you’re finishing your project on that date and you’ll send it to them to check out.

This makes the deadline feel very very real (even though, of course, it was self-imposed and totally made up). Somehow this is enough, however, for your Creative Diligence to turn on, like a werewolf on the eve of a full moon, and accelerate your work towards completion.

Friends help friends stay diligent.

The right friends can be positive, motivating forces of Creative Diligence. When I realized I wanted to make a change to my practice, I started by taking the uncomfortable step of texting people I trusted and respected and telling them about my failing… and that I was trying to figure it out. This put me socially and emotionally on the hook for finding an answer. The exquisite pressure of people whose opinion you deeply care about being aware that you are trying to solve a painful shortcoming helps you strive mightily to overcome it. Thank you, friends!

Fellowship of the Few

A final word… if you do finish a project, tell me. I want to personally send you a virtual high-five, artist-to-artist, as an acknowledgment that you made good on your promise to yourself and all other artists to uphold the fellowship of the few who dare to both start and finish.