Winners Never Quit (but maybe they should): Three Questions to Ask

“You can do good, productive work in a job you hate, but it likely won’t be constructive for the life you hope to build for yourself.”
Brice Montgomery

how to know when to quit

Winners never quit (but maybe they should).

A funny thing happened on the way to the blog.

I’m writing this post because Amenable’s other writer—Amelia—quit before she finished it. That’s what we call theory in action. While I can’t presume to know the direction she was going to take this topic in her exploration of it, I can say that she had some great reasons to quit. 

Quitting is often stigmatized as a mark of apathy, but let’s consider why. Culturally, there seems to be a tacit assumption that if you aren’t producing, you aren’t living up to your potential. Our prescribed social values are dictated by a fixation on productivity, a kind of moral market economy. There’s certainly value in persistence, but I’m here to argue that there’s also a lot of value in knowing when to tap out, and I have three guiding questions if burnout is leading you to consider quitting a project or job.


How to Know when to Quit: Three Questions to Ask

1. Is it essential?

One theme I’ve been championing within our work at Amenable is the importance of doing less. Lest I sound like a bum, I don’t mean in the sense of cutting corners or haphazardly rushing through work. 

Instead, it’s important to recognize that everybody is acting from a place of limitation. We have only so many hours in the day, and work is not the sole purpose of life. At Amenable, we try to integrate this mindset into our project—if we’re building a website, how can we do it in a way that recognizes that visitors have more important things to do with their time? This isn’t minimalism, but something more akin to focus.

In the rare instances where a project can’t be reduced to a healthy essential, it’s probably time to call it quits. To put it another way, if you can’t articulate a clear heart to the work, there probably isn’t one. In these cases, actually following through would do a disservice to whoever it is ostensibly supposed to benefit.

We’ve had a few clients bring projects to us that just don’t click, and after a few conversations with them, it often becomes clear why the projects aren’t working—they aren’t the essential projects. Something else is going on in an organization, and the proposed project was just the wrong solution to that challenge. In these cases, it’s been helpful to stop, take a step back, and make sure that we find the project that should take precedence.


2. Is it constructive or merely productive?

Closely related to the first point, it’s helpful to reflect on what exactly a project is adding to the world. 

Regardless of your work, you don’t have the luxury of guaranteeing every project is “meaningful,” and it would be privileged to pretend otherwise. Even so, this question may be helpful for you to reflect on patterns within your work. 

The problem may be with the project or job itself, or it may be that the problem is with you. Before you scroll away because I sound too much like an intrusive thought, this isn’t an indictment of your ability or worth. Instead, I raise the point because many of us have overstayed in a job simply because we feel like we’re supposed to, even if it isn’t a great fit. 

There are several reasons this may be the case. Some people may be figuring out where they professionally fit post-COVID, a task easier said than done. Similarly, many likely have a background that celebrates a “protestant work ethic,” which generates internalized beliefs that quitting is a mark of apathy. Finally, there are massive generational shifts at play in cultural expectations for sustainable work that further complicate the question of when to quit. Your parents and grandparents likely had one or two jobs throughout their professional career, and that simply isn’t tenable for many people now. Unfortunately, that extra mobility makes it harder to figure out the difference between not enjoying work for a while and disliking a particular job.

You can do good, productive work in a job you hate, but it likely won’t be constructive for the life you hope to build for yourself. 


3. Is it at the cost of your energy or at your expense?

In keeping with the idea of limitation, there is a good way and a bad way to feel “empty” after a project. Most of us have probably experienced the fulfillment of working on something that felt impossible, only to see it reach fruition in a surprising way—when you finish with that feeling of, “wow, I have no idea how I made that work.” These are the projects that cause you to stretch your creative sensibilities and push back against your limitations. They’re the ones that are fulfilling even when they are draining.

Likewise, the odds are good that you have also experienced the opposite. You’ve plowed through a project, hoping that it would get bearable somewhere along the way, only to finish it with a resounding thud. These are the projects that take more than just your energy—they happen at your expense, and they exhaust your limitations without giving you anything in return. 

Again, not every project can be personally fulfilling, and some will be exhausting even in the best circumstances, but if there is a recurrent pattern of projects or work that empty you without creating ways for you to recharge or find satisfaction in the work, it may be time to find the exit door. 


Begin Again

If you made it this far, congratulations on not quitting. If you didn’t, I hope that you jumped ship for good reason so that you could create extra time and space for yourself. If you’d like to discuss this subject, or you’d like to share your best quitting story, hit us up at hello@weareamenable and let’s talk.

Brice Montgomery
Creative Director
Brice likes to think through how messages are best translated for different audiences and purposes. He also makes baked goods.
Amelia Gray
Amenable Alumna
Amelia loves connecting with people through language by finding the right word for the right moment. She hopes that sharing her creative process will help other people be confident in their own. In her spare time, you can find her birdwatching or developing her Spanish.


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