Living

Quitting isn't failing

Headshot of Jonathan Jackson with rainbow light leaks in corners
Jonathan JacksonFebruary 4, 2025
Person sitting at at desk with a laptop holding a piece of paper

In November 2018, I walked away from a successful media business I co-founded. We were gearing up for a new capital raise, customers were lining up and our growth trajectory was incredible and by leaving, I blew up. The details are complicated, but I knew it was time; I chose to leave and with it, a part of me did too. Overnight, the thing I had given all my energy to ceased to be. ‌This is the part of building things we refuse to talk about; when it is time to leave, and the shame around doing it.

Winners quit the right things. That’s how they go on to win at the right things.

Up until that point, most of what I'd learned about business and entrepreneurship focused on staying the course, surviving to another day and relying on grit to overcome challenges.

‌Those are necessary and critical values. Anyone can start a company, but building a business is not for the faint of heart. What I didn’t know is there are other skills you need when it’s time to walk away from something you’ve built.

It starts with learning how to quit.

Working through the pain of quitting

To make it through quitting, I had to confront one of my recurring nightmares: the feeling of no longer being publicly successful. These are some of the biggest challenges I faced while quitting—and how I overcame them.

Beware the shame spiral

I try to operate with a high degree of agency. If I say I am going to do it, I will, unless I can’t.

But I just couldn’t seem to do the things I was used to doing at the level I was used to doing them. Add financial pressure, social anxiety and a host of difficult relational challenges, and you can see how I started to spiral with shame.

Status limbo

One of the most disquieting things that happens when you quit–or are forced to quit–is the feeling of status limbo. You no longer have the social and professional standing associated with your previous role, and what you’re going to do next has yet to materialize. This “status limbo” is painful, yet unavoidable. Who you were is not who you are going to become.

It also reveals where you put too much of your identity, which is its own kind of self-realization. You can no longer rely on where you were to get you to where you need to be. Winners quit the right things. That’s how they go on to win at the right things. So to even become what you imagine, you have to quit something. Saying it is easy; living it is challenging.

The limbo exists because you are not yet where you are going, and you aren’t where you were. How you manage this state is important, because it sets the tone for the new places you will be. Mixed with all the other pressures of life and running a business, you have to take a look at whether who you are and what you say you want are in line with each other.

The most important thing I had to assess was whether I thought I was worth going through what this transformation would require.

The science behind the pain

There are a few different ways our psyche plays against us when we quit. In her bestselling book “Quit” author and researcher Annie Duke, shares a few traps our brains play on us when we struggle to quit, and analyzes the behaviors we adopt to avoid quitting.

  • Loss aversion: waking up in a cold sweat because you don’t want to lose, but you aren’t excited when something goes well because you’re on to the next thing. As a result, you may pass up valuable opportunities out of fear of losing.
  • Recency bias: relying heavily on recent events, which leads you to misremember how things really were. This can cloud your judgment and keep you from recognizing when a situation has changed for the worse.
  • Escalation of commitment: starting with an agreement, then finding yourself juggling five different tasks. Instead of honoring the initial agreement, you hold on to what the original goal once represented.
  • Pass/fail goaling: viewing every outcome as purely a success or a failure. If you closed 15 deals when your target was 20, that doesn’t mean you totally failed—there’s still progress and room to improve.

There are many more, but these will inevitably pop up during your transition as you lean into quitting what you must. Being able to identify them can save you from being caught by surprise. For me, I was most susceptible to the sunk-cost fallacy and loss aversion. Those come from my need to feel a sense of completion, yet also my tendency to feel unsatisfied even after fulfilling my commitments.

Creating new possibilities

Recognizing these logical fallacies is just the first step. Eliminating the wrong things, without replacing them with the right things, will almost always lead you to relapse. Here are some practical ways to work through the fear, uncertainty and self-imposed limits around quitting–so you can let go strategically.

Exercise the imagination muscle

This was hard. I thought I knew how to work out my imagination, but I realized I was just repeating things I already knew. The same tactics to problem-solve, the same habits to start my day, the same thought patterns. They weren’t bad, but they were also not helpful to who I was becoming.

The issue wasn’t my goals or motivation; it was accepting a new identity that quitting had helped usher in. To do that, I had to grieve for what no longer existed, and work through the feelings of loss and confusion.

You will lose things when you step away. It’s painful, and there is no easy remedy to that pain. Much of my own stumbling came from thinking there needed to be an explicit path, instead of embracing nuance and creating my own way forward. Confusion is a natural part of the process of quitting. But it’s important to acknowledge that feeling confused is part of the process you need to work through to get to where you need to be.

It takes as much courage to quit as it does to start. Realizing that can help you position yourself for what’s next, and imagine a new ideal for your life and future business.

The 4Cs: a sustainable framework for navigating transition

As I’ve tried to walk through new seasons that require quitting, I've stumbled into a personal framework. I’ve tried to embrace it even when I’m depleted, exhausted or disillusioned.

I’ve refined them to work when there’s nothing left to give. The key was to make them easy to activate on challenging days, and they’ve sustained me when I needed additional support.

As a side note, I’ve found systems are more impactful than goals, because they help you meet the moment you’re in, not the moment you imagine you should be in.

  • Commune: find ‌people to spend time with. It can be a coffee date, a call or a simple text–just ensure you’re making intentional time and space.
  • Curate: get aggressively selective about what you allow into your mind and digital environment. Audit your YouTube, Spotify and any other media you consume. Create audio delicacies for yourself. Find new corners of the internet to explore–and schedule it. Become a curator of your own experiences, both digitally and physically.
  • Cultivate: nurture and grow things that nourish you. Maybe you have a habit you’ve been working on building or a book you want to finish. It could be simply watering a plant in your home.
  • Craft: this can be anything you put effort into building, from hiking to pottery to be building a LEGO set. The key is to put your hand to something unrelated to your professional identity.

The only way out is through

None of these solutions are a magic bullet. No system is. But by leaning into a structure that can help you rebuild and preserve moments and glimmers of joy, you can build capacity. But you do need to ask yourself: “am I worthy of letting go, the same way I hold on? Am I willing to let go of the shame and fallacies I feel around quitting? Can I let myself pack lightly for where I have to go next?”

In the process of building anything worthwhile, quitting is inevitable.

There’s no wrong answer, except choosing to repeat ineffective behaviors. Having grit and quitting are part of the same continuum. The issue is with our language and perception, not our effort.

Taking a step towards quitting is a badge of courage, not a scarlet letter. In the process of building anything worthwhile, quitting is inevitable. You will quit clients, strategies, locations and plans. Our deleted items in email are filled with things we no longer use, forgot about, or unsubscribed from. We can do the same in life if we allow ourselves the ability and opportunity to do so. How you go about quitting is a skill you can develop, harness and apply.

Persevering through something requires turning away from alternatives, just as sticking to something means committing to a path forward.

In 2025, what I want for myself–and for you–is to build the capacity to quit freely, early and often. It is not a sign of weakness or a lack of courage. Quitting is a sign of maturity–a quitter is someone who knows what their value is, and how to consistently use their time to get the most out of it.

We can all become that person. But first, you need to quit. When you do, you’ll be a different person. That’s a good thing.

Share
Headshot of Jonathan Jackson with rainbow light leaks in corners
Jonathan Jackson

Jonathan Jackson is a strategist, media operator and executive communications expert with a global track record in narrative development, content strategy, and business growth. He specializes in positioning leaders and businesses for growth by building operating systems for influence. He writes a newsletter on media and markets called Due Dilly with his best friend Carl.