How to quit (and why it leads to happiness)

May, 2004: I’ve just stepped off stage from my last magic show ever. It feels… anticlimactic.

I imagined that I’d be emotional, but I’m not.

It’s as though today’s show held little significance. I didn’t even tell the audience that it was my last show.

Though I admit I feel a little guilty. Over the past 12 years, my manager, parents, and brother have poured tons of time and energy into my success. In some ways, my decision to quit feels like a betrayal.

But instead of worrying too much about that, I pack up the show, load up the car, and exhale. It’s nice to be done with this shitty job.


Have you ever had the experience of getting exactly what you wanted – a certain amount of savings, a job, a relationship, a cool apartment, a status symbol, whatever – only to be disappointed shortly thereafter?

Most of the time we tell ourselves, “Oh, well I guess I just need more!”

While the tendency is understandable, it’s also misguided. Once you’ve created a life you enjoy, adding more tends to have diminishing returns. However, you can create huge wins by removing the stuff that doesn’t work or is causing friction.

In this article, I’m going to make a simple argument: the path to happiness is lined with eliminating all of the shit that doesn’t serve you. I’ll also give you practical tips on how to quit, explain why doing so is often terrifying, and advise on how to deal with haters.

Why quitting leads to happiness

Imagine for a moment that every day you get out of bed and stub your toe on the nightstand. In a situation like this, you have two options:

1) Accept that the nightstand will always be in your way and hope that you learn to avoid it or grow numb to the pain.

2) Move the nightstand.

Obviously, you’re best off just moving it.

Of course, quitting your job, ending your marriage, or giving up cigarettes is a hell of a lot more emotionally demanding than moving a piece of furniture. However, thinking about the simple things that cause you pain can be instructive. Many people choose to adapt to situations when they would be better off changing them.

The problem is that changing your life can be tricky. It almost always requires courage and a decent amount of work. Because of that, many of us never make the changes we want (or need) to.

Adapting to a situation that doesn’t serve you is a bad idea (unless the situation can’t be changed, in which case learning to adapt is wise). It wears you down and holds you back from fully stepping into your life. When you finally quit something that has been draining you, two things happen.

1) All of the frustration that came from whatever used to bother you? It vanishes. This alone is a huge win.  

2) You create blank space in your life. That space can be scary, of course, because it means that you’re dealing with the unknown. However, the space makes it possible for you to replace whatever wasn’t working with something that will help you flourish. It’s difficult for new things to appears in your life, if you don’t have the space for them.

How to overcome the fear of quitting

We are often told, “Better the devil you know, than the devil you don’t.” The idea is that it’s better to deal with familiar circumstances – even if they suck – than to take the risk of dealing with something new because that might suck even more.   

Honestly? That’s horrible advice. A better approach is to continue taking calculated risks and engaging with the world until you create a life you love.

The problem is that change can be scary. Most of us prefer the familiar to the unknown. Fortunately, there are ways to overcome this.

Realize that the devil you know is way scarier than the devil you don’t. Think about the thing(s) you are considering quitting. Ask yourself, “What happens if I don’t quit?” The answer is that life is likely to get worse.

You’ll either get worn down or the frustration you feel will continue to grow and expand. When you reflect, you realize that the bigger risk isn’t the unknown, it’s choosing to stay on a path that you know doesn’t serve you.  

Use the worst-case scenario as a thought experiment. When we consider quitting something, we often feel a quiet sense of dread. That dread prevents us from further examining whether or not we should quit. It closes us.

However, when you pause to examine your fears, you’ll notice that many of them are nothing more than phantoms of the mind. You’ll realize that things that felt prohibitively frightening when they were unexamined become manageable in the light of day.

Spend time figuring out how you could bounce back from the worst-case scenario if it ever occurs. Let’s say that you want to quit your job, but you’re afraid that you’ll run out of money before you get a new one.

There are countless ways of fixing this problem. Maybe you learn to be more frugal before you leave your job, so your savings will last longer. Maybe you start renting out a room in your apartment or driving for Uber to supplement your income. Maybe you decide that you 100% will quit your current job, but not until you’ve landed a new one. Maybe you ask friends or family if they’d be willing to let you crash with them. Maybe you take out a loan.

The important part is to realize that you are capable of handling almost anything that life throws at you (often with more grace and ease than you anticipated).

Figure out how you’re going to do it. One of the reasons quitting is so intimidating is because people rarely take the time to figure out how they’re going to do it. Though going cold turkey is entirely possible, baby steps are often more effective.

There was a decent gap between when I decided to quit professional speaking and when I actually quit. During that time, I saved money, figured out what I was going to do instead of speaking, and explained my decision to my friends, family, and clients.

Recruit help. If you’re struggling to quit something, recruit help! This can be a friend, an accountability buddy, a coach, a therapist, a 12-step program, whatever. As always, there’s no need to go it alone.

Finally, realize that few things in life are permanent. When we make big life decisions, we often feel as though they are destined to become permanent. In reality, almost nothing is permanent.

If you realize that your life was better before, you can always return to that lifestyle. Sure, there will be some differences – you may not work for the same company or live in the same apartment – but you’ll be able to create something close enough. Once you realize that you can fix almost any “mistake” you make, taking a chance in life becomes much easier.

18 Things to consider quitting

I’ll leave you with a list of things to consider quitting.

As always, the time to start is now. Even if you’ve invested tons of blood, sweat, and tears – like I did with magic – if something no longer serves you, it’s probably time to let it go.

  • Being an entrepreneur or freelancer (a lot of people who were seduced into being entrepreneurs would be much happier being an employee, regardless of how successful their business may become)
  • Spending time with the people you only pretend to like
  • Watching tons of TV
  • Going to college (virtually everyone should complete high school, but in my opinion, higher education isn’t for everyone – a very real part of me wishes I didn’t waste my time)
  • Drinking, doing drugs, or smoking cigarettes
  • Living in a city you don’t like (moving from DC to Denver was one of the best decisions I’ve ever made)
  • Pretending that you care about politics, sports, or fidget spinners
  • Staying at a job you hate
  • Obsessing over personal development (there’s nothing wrong with you, I promise)
  • Playing small
  • Staying in a relationship that just doesn’t work – even if you love the person (but move slowly and carefully here to make sure you’ve exhausted every option; keep in mind that all relationships go through rough patches)
  • Eating junk food or having an unhealthy relationship to food
  • Neglecting your mental health
  • Treating yourself poorly (you really should treat yourself like a rock star)
  • Spending time with people who tear you down
  • Lying
  • Feeling guilty for prioritizing your needs (I’ve had to deal with this numerous times, including when I quit magic)
  • Pretending that you aren’t happy, capable, beautiful, confident, bold, or awesome (soooo many people live under this delusion)

Post script: how to deal with the haters

When you really grab life by the reins, haters start to crawl out of the woodwork. The shitty part? Many of them will be people close to you.

Nine times out of ten, their reactions have nothing to do with you and everything to do with unaddressed issues in their lives. There’s a good chance that observing your proactivity makes them uncomfortable; it reminds them that they are responsible for themselves and that they aren’t doing a very good job with that responsibility.

It’s tempting to try convince them that they’re wrong. Don’t waste your time.

Instead, listen politely and say something along the lines of, “I appreciate your perspective.” Don’t bother trying to get them to understand you. Instead, revel in being misunderstood.

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10 thoughts on “How to quit (and why it leads to happiness)

  1. Such a great and timely post Jason! I’m feeling this so hard right now.

    I quit my “successful” cartoon brand a few months ago. Like any break up, it felt equal parts liberating and devastating losing a slice of my reality. Two of the biggest challenges you touched on that I faced: 1) Permission to quit, and 2) An identity crisis on the other side.

    It took me about 6 months after flat-out hating my work to actually walk away. As I was seething behind the scenes, the internet world was telling me that I’d made it and I should be THRILLED. To your first bullet point of things to quit, I didn’t realize I was allowed to opt out of the business model that the entrepreneur world said I should be striving for.

    Right now I’m just coming out of an intense identity crisis after having been stripped away of “my thing” on the internet. I’m still unsure what’s next but I’m finally at a point of relishing the space. (I’m curious: what was it like post-magician for you?)

    I wish more entrepreneurs were saying what you’re saying: that it’s okay to quit and you should be honest about what you really want and what’s really working! Thanks for giving a voice to this.

    1. Stephanie – first of all, congratulations! I know just how weird it is to walk away from something that seems successful. That you did this right around the time that your peers were telling you that you “made it” must have been insane. In all honesty though, that makes me admire your decision even more.

      Isn’t it weird with entrepreneurs? So many of us are miserable but wandering around telling the world we love it, and then when people suddenly get honest about it, a chunk of the community revolts. It sucks. Bravo for being a luminary here.

      As far as quitting magic (or speaking, for that matter)? Gosh. I was in a haze. It was (and at times, is) such a part of my identity that I found myself doubting my decision, awkwardly trying to find a new angle in life, and feeling relieved all at the same friggin time.

  2. I believe that quitting leads to happiness because the thing one’s quitting has started not from inside out, but the other way around.

    It’s easier to listen to others when you don’t know (or aren’t sure) what you want to do, instead of listening to yourself in the most specific way you can. And so, you are starting something based on what others believe you should do. But unfortunately, that advice mostly works for those that are giving the advice, not for the receiver.

    By the way Jason, great podcast session on the Marketing Copilot Radio.

    1. Hey David, great to hear from you man (and glad you enjoyed the interview 🙂 ). And once again, I feel ya. Proactively quitting something has to come from the inside out, and personally, I think that’s – by far – the best path towards happiness, healing, and probably optimism too. 🙂

  3. Great article Jason! Though I do hope that you don’t quit blogging! I really enjoy every one that you write!

    1. Thanks, Becky – that means a lot to me. 🙂 And no worries – I plan on keeping the blog alive for a while! I really love this project.

  4. Hi Jason, great article as usual. I have a question about when you might not want to quit but you’ve been beaten down. I’m in a job I love, and recently went for a position that I didn’t get. I was- no exaggeration- the only person qualified for this position with the most experience by a Grand Canyon-sized margin and a specific qualification for this exact position, and despite that and although it’s what I’ve been aiming for and building up to for years, I didn’t get it, perhaps due to nepotism (but that’s a different story). My question is, how do I keep working in this job I love knowing that my chance to achieve the position I’m aiming for has vanished (yup, literally no chance now), and how do I pick myself up as someone with extremely low self-worth and nothing else going for me? I’m sorry if the question is specific but I think it’s a tricky situation that people find themselves in surprisingly often. Thanks for your time, and keep writing the good write! (Sorry, I tried to pun)

    1. Hey Adam, I appreciate the kind words, thanks man. And sorry to hear that you got passed over for a job that you were the best qualified person for. That sucks. A lot. As far as how to handle the situation, I think you should try to do the following:
      1) Take a few days off and reflect on whether or not you want to stay in this job, knowing that you’ll never be able to rise as high as you’d like to. Go for a long walk, sit in silence, journal, etc. If you discover that you love the company and the people, and that it’s not too big of a deal that you got passed over, then consider staying. If you discover that getting passed over did permanent damage to you, and that you’ll never be able to look at your work / company the same, then consider starting a new job search.

      2) And this is actually the more important one: get help for your extremely low self worth. If your company offers insurance, use it to go see a therapist and heal. Doing this sooner rather than later will improve every aspect of your life. My bet: if you take the time to heal yourself and develop the self-worth you deserve, then you’ll eventually find a wayyyyy better job at a company that treats you well.

      Good luck, and thanks – I’ll do my best to keep writing the good write. 🙂

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