How do you know if it’s time to quit?

“Work harder” isn’t the answer to every creative crisis

Creating something awesome and new under the sun is not a easy. You’ve got to have perseverance and grit to get through the hard parts, finish your projects, and launch them into the world. And if you’re doing it right, you will inevitably have a moment where you ask yourself if it’s worth it. How do you know when it’s time to quit?

Choose your own adventure

You’re proud of yourself. You’ve managed (with much difficulty) to carve a chunk of time out of your busy schedule for your project, that idea you’ve been so incredibly excited about.

You sit down to work, but before you even touch it, you start to feel [anxiety grip your throat/angry and resentful/sleepy and disengaged].

You rub your face and think, This project is [overwhelming/impossible/not my thing after all]. [I’ll never finish/I can’t master it/I don’t have anything useful to say.]

You stare at it for another minute and then [your phone buzzes at you/a notification pops up on your screen/you notice you’re hungry], and you tell yourself Oh, I’ve just got to do this one thing, and I’ll get back to my work.

An hour later, after [Facebook/Instagram/email/cleaning the house] you shake yourself alert, and get down to the hard business of [berating yourself for being a slacker/not being cut out for this/sucking].

…Ring a bell?

In a group coaching session a few months ago, someone verbalized the scary question raised by the scenario above: “How do you tell the difference between getting stuck on a project and just being over it?”

How do you know if it’s time to quit?

When you’re stuck on a project, and you don’t know if it’s you, or the project…

Being able to face the tough parts of the creative process and get through them is an essential skill. It’s really important to cultivate that kind of endurance if you’re serious about growing as a creator, finishing work, and getting it out into the world. Nothing will ever be perfect, and, despite that, you should still stick with your projects, push through, call them finished, and publish.

But I’m not going to tell you you should stick with every project you start. God forbid.

As you start to figure out why you’re feeling discouraged about your work, the first thing to understand is that hitting a creative crisis is NOT a bad sign.

Quite the contrary.

In my book, Out on the Wire (aff link), I talk about how big, ambitious projects often land you in the Dark Forest. In other words, it’s your courageous pursuit of the awesome that has lead you to this dark place. 

The Dark Forest is not “blank page syndrome.” It’s not about getting started.

You get lost in the Forest in the deep, dark middle, when you’ve worked so hard, gathered so much research, gotten really deep in, and, instead of using all that as fuel, you just feel overwhelmed, like you will never get a handle on things.

And the truth is, you ARE in over your head.

That’s why it feels that way. You ARE incapable of doing what you’re trying to do—as of yet. Because you have to master new skills to be able to do it.

I talk about the Dark Forest as a good sign because it means you’re really stretching as a creative person.

That doesn’t mean it’s fun. It will require taking creative risks to do something bigger. And when you’re working out on the wire like that, it takes time to wrap your brain around the problem and figure out how to put all the puzzle pieces together.

But if you don’t take on a bit more than you can handle, you’re not growing as a creative person. Facing—and of course, overcoming— that challenge is where all the joy in your work comes from.

Frankly, finishing can be a let-down after the feeling of mastery that comes from learning to make something totally new.

After I learned about the concept of the “Dark Forest” from Jad Abumrad of Radiolab (actually, he calls it the “German Forest,” for obscure reasons having to do with Wagner), I read a tweet by cartoonist Kazu Kibuishi…

Check out those retweets. It struck a nerve, to say the least. I always think it’s way interesting when something gets more retweets than likes.

(…and if you want to hear more, Kazu’s formulation felt so true to my experience, and so powerful, that I interviewed him for the Out on the Wire Podcast, which is when he introduced me to his term “idea debt“…)

But it wasn’t until a year or so later, as I flailed around trying to get a handle on how one runs a business, that I started to see that tweet as one iteration of a pattern.

I happened on this chart, and something about it rang a bell. It depicts the emotional stages of implementing change, and kind of looks like a mountain.

The Emotional Cycle of Change, by Kelley and Conner

Stage 1: Uninformed optimism. (AKA “This is going to be awesome”)

Stage 2: Informed pessimism. (AKA “This is hard”)

Stage 3: Hopeful realism. (AKA “Hey, not bad”)

Stage 4: Informed optimism. (AKA “That was awesome”)

Stage 5: Completion.

Some genius turned it upside down, in which form I find really it maps a lot more closely to lived experience…

They also added a well-named middle step, the “Valley of Despair” (AKA “This is Terrible/I’m terrible”).

Essentially, we all get selective amnesia when coming up with a new idea for a project. We are energized by the notion, and think, This is awesome, what a great idea, this is going to be so fun (and, maybe, It’ll make me a million, I’ll be famous).

Then we start to work, learn more, and it gets really hard. We see how this isn’t going to be a triumphant slide into home base.

We go even deeper, learn more, do more, and get completely mired in the complexity and difficulty of the thing we’re trying to do. We feel like, this is impossible, I don’t have the skills to handle this. I’m lost, I can’t make this work. That is the Dark Forest. That’s the Pit of Despair.

When you’re thinking “is it time to quit?”, you’re very likely in the Pit of Despair.

“Kinda knew that, Jessica, thanx ?”

Hang on, hang on, I swear I’m going someplace good with this.

Crash and Burn? Or fight through?

I’ve new seen this chart applied to all kinds of creative endeavors, and especially to the process of creating a new business. Here’s one I thought was useful:

Note this part: “Crash & Burn”

Just because it’s a “good sign” that you’ve created your own special Dark Forest that you need to trek your way out of does not mean you’re going to make it.

In this stage, a reliable, sustainable creative process (as we develop in the Creative Focus Workshop) will get you through. Grit pays off.

(Assuming it’s not time to quit. But let’s put a pin in this one for the moment.)

“Crisis of Meaning”

Here’s what you see when you plot out the “creative process” on a curve. The nadir represents a turning point. As the chart above has it, a “Crisis of Meaning.”

It’s a decision point: On this chart, there are two ways to go:

Are you going to crash & burn?

Or are you going to go from “I’m terrible” to “hey not bad”? Are you going to keep going, and work through it?

Goodbye Dark Forest, Hello Khyber Pass

But even if you do recommit and decide to see your project through, there’s another tough phase to the creative process.

See that up-slope on the chart? While it does mean that as soon as you’re through the Dark Forest, there’s nowhere to go but up…

…that’s a steep slope.

When I interviewed Ira Glass for Out on the Wire, I asked him: do you ever get into the Dark Forest? And I’m sure that, in his life, Ira has been in the Dark Forest. But at this point in his life, he’s so good at what he does, and he prepares so thoroughly—constantly outlining and re-outlining—and he understands structure so well (plus he works with world-class collaborators) that he kinda doesn’t get stuck in that middle place.

What he gets into—what he was in the middle of when I spoke to him—is a stage he compared to the “Khyber Pass.”

If you’re unfamiliar with the geography, the Khyber Pass is the famous mountain pass essentially between Afghanistan and Pakistan, a strategically-important trade route used, fought over, and captured by armies from Genghis Khan on.

Here’s Ira on his metaphor:

“It’s more like I’m a soldier in an army that’s crossing the mountains by foot in the snow. You know, through the Khyber Pass. And there’s an opposing army trying to stop me. And also, I’m carrying a pouch full of poppy, and it would be so much more enjoyable to be lying down and taking that, rather than slogging my way through Asia on my trek of conquest…

“…I think that, along with everything that’s great about creative work, there’s a certain tedium to certain parts of the execution. …That for me is where procrastination can really set in. Because I know what it’s gonna be like.”

You’re climbing the Khyber Pass when you know exactly what needs to be done, but it’s just hard, and you have to push through it. You just need to put one foot in front of another.

You face procrastination because it’s difficult, it’s even boring. But it’s not mysterious, it’s not unknown.

So, when you avoid the crash and burn, the only way to go is up. Things are getting better. But getting up that slope is also a killer, and that’s why the question, “How do you know if it’s time to quit?” will haunt you here more than in any other stage.

Is it worth it? Or is it the Sunk Costs Fallacy at work?

It can be really easy to fall into feeling like you “have to” finish something you start.

Our society does not look kindly on “quitters”.  (Warning: autoplay video ads. Also, side note: how the hell was Dean Koontz’ wife’s support “a win and a curse”?? Effing typical.)

You pictured what it would be like to finish so clearly, to let it go feels like self-betrayal.

And then there’re all the sunk costs.

But here’s the thing: the project per se—no matter what it is—is not the point. The project is a vector. It’s the means by which you communicate something, create some kind of change, and most importantly, it’s how you get closer to the dream version of yourself.

And it’s a dynamic system: the projects you choose will change your vision of where you want to go, as much as your vision should guide what projects you take on.

That said, there are projects that don’t move the needle at all. And there are projects that head in the exact wrong direction. And when you realize that, no matter how much you’ve sunk into the project, you’re better off quitting.

Quitting is not giving up

When it’s time to quit, it can certainly be painful. But you know what quitting isn’t? It’s not crashing and burning.

Quitting is taking control. It’s knowing you have the power to stay or to go, and exercising that power.

You decide, I’m not going to do this. There will be repercussions (even within your own mind), but I can face them. I hold the power.

“Crash and burn” is not the only option. There’s also “decide and quit.”

For example, one Creative Focus Workshop student decided to sunset her goal of writing a new website for her business. Doing that writing would mean learning a whole new set of skills that she realized she didn’t care about, and that wouldn’t serve her.

Her true goal was not to learn copywriting, her goal was to have home on the web that would make clients comfortable, and interest them in working with her.

She hired help instead, and when she realized that she could choose not to put herself through this project, she felt like a boss.

That doesn’t mean it wasn’t emotionally difficult to get there. Before she could realize that quitting could make her feel like she’s winning, she had to grapple with her association of quitting with failure.

As soon as the decision was over, though, the clouds started to part, and she felt clearer than she had in ages.

And when the project is RIGHT: not quitting

When you know the decision is in your hands, continuing to face the Dark Forest is also more empowering. Because you chose it.

Another CFW student was deep in the Dark Forest on a talk he was writing. But in this case, his goal is to build a speaking career, so getting through the Dark Forest on his first long-form presentation was 100% worth it. It built skills he needs and wants, in addition to simply having a great talk ready to go.

How do you know if it’s time to quit?

Unfortunately, there is no litmus test. You need to know the why behind your project. What is it for? And that’s complicated.

When you’re trying to sort this question out for yourself, you can do some journaling, make lists of what your intentions are, but I can’t say enough about how important it is to gain perspective, which usually means talking to other people. All alone, you’re capable of talking yourself into something you shouldn’t do, and out of something you should do.

It’s especially difficult to pull these threads apart, because our projects are emotionally loaded. You are invested in the outcome, yes, but even more than that, you’re likely to be invested in your self-image as someone who is doing this thing. Someone who finishes things.

Creative people (maybe all people?) tend to have a streak of self-punishment. “I’m tough, I can get through this!” It’s important to acknowledge that sometimes the outcome is not worth getting through it.

Assess and decide

That’s why it’s important to go through the process of assessment and decide: is the end result worth it to you? Make a pro-con chart. List things that go into the project, what you’ll need to learn, the hard parts you’ll need to go through. Ask yourself: does this need to be done? And do I need to be the one to do it?

List the criteria that would mark the project as successful for you. How does that balance against the work that’s ahead of you to finish it?

The emotional fallout of quitting can be tough to deal with. I suggest a ceremony of sorts: a respectful putting-to-rest or sunset ritual.

Gather up all the evidence you have of this project, store it in a box or in a deeply-buried archive in your hard drive, and say thank you. Acknowledge that the project itself served a role in your life and that the work of deciding gave you new clarity on what you want in your life.

There was a reason you did it, and a reason you stopped, and knowing those reasons is a gift.

The beauty of quitting is making room for the work you DO need to be doing

There’s a joy and freedom that comes after quitting something you knew in your bones was wrong. And the energy that flows from that needs a channel.

That channel is the project you’ve not been able to give your focus to, that does represent your next step.

Remember, a project, and work on that project, is a vector. Doing new work and forming new goals is how you form an entirely new self-image.

I went from self-conceiving as a minicomics artist, to an author, to a business owner. None of those old identities have been invalidated, but they’ve been subsumed into a larger image of who I am and what I can achieve.

To do the new work I set out to do, I take on new and different responsibilities.

I give myself a promotion.

You can’t get a new job unless you’re willing to quit the old one.