“Winners NEVER quit anything”.
They cut through every challenge ahead of them with the sword of perseverance. Obsessing until their big scary beast of a goal is struck down, they leave only success in their wake.
They are the Harry Potters, the Tony Starks & the Luke Skywalkers of our world. Overcoming evil precisely because of their undying desire to never give up. They waver. They doubt. But, they never quit.
Heroes with stories like this are all very inspiring. They energise us to strive to new heights in our own lives and teach us to stay the course because it’s the one thing that will lead to our greatest success.
But, what if told you this isn’t entirely true?
That quitting is part of the game.
Because in real-life you’re faced with difficult decisions that require you to let go of one path in order to reach out to another one.
There’s no obvious right way. We lack a Voldemort to join, a Thanos to follow or a Galactic Empire to submit to. Pros and cons fill the coffers of both sides of the coin. Which means our choice to continue is consumed by complexity.
Knowing when to stick at it and when to quit before it’s too late is a skill. One that can be learnt and applied to our own lives.
As someone who has already closed two businesses, walked away from a running career and turned down more work opportunities than I can remember, I’ve learnt a thing or two about giving up.
So, here’s everything I’ve learnt about deciding when to quit.
#1: Find Your Peace with Failure 🕊
“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end” - Denis Waitley
You only make the best decisions available to you at the time.
Assuming that you’re a rational human being capable of consideration, every choice you take is a reflection of what makes the most sense in that moment.
For you can only speak for how you feel right now. Not what will change inside of you tomorrow, next week or in 2030.
There are no “what ifs”. There are only “what ares”. Trying to apply the lens of today to decisions of yesterday will leave you with only disappointment.
Mastering quitting means letting go of these past choices.
And embracing who you are today, in the present moment.
Here’s how you do exactly that:
1) Reframe Mistakes as Learning Opportunities
The only mistake you ever make is when you don’t learn.
Everything else is simply part of the journey of life you’re on, exploring the possibilities of who you are and discovering what you enjoy.
Even when you end up doing something you hate, it’s still time well spent. You learnt what doesn’t work. And that’s equally as valuable.
So, don’t shy away from mistakes. Own them by:
Analysing what went wrong - sit down and conduct a full review.
Asking for feedback - listen to first-hand experiences.
Applying the lessons - list out how you’ll implement the learning.
Teaching others - consolidate your lessons by explaining your mistakes.
Loving failure - obsess over the feeling of being a beginner.
After all, mistakes are just echoes trying to teach you something.
You’ve just got to listen to them.
2) Understand The Power of Inertia
There’s an opportunity cost to every decision.
Quitting effectively means accounting for both the short-term benefits of a decision and the long-term consequences.
Since we all have the same 168 hours in a week, there are a limited number of “yes’s” we can give away. Which means every time we embrace a decision, we reject countless others that we never even considered.
But, there’s an even bigger factor at play here too.
Every choice you make is an investment. By spending time on one life path, you reap the returns both good and bad.
Which practically can look like this:
Accept a new client in an industry you don’t enjoy.
Get paid a lot. But, reduce your time with other clients.
Build a great reputation. But, with people you don’t like.
Land even more clients. But, from the same industry.
Find yourself fully booked. But, delivering work you don’t enjoy.
Knowing when to quit means asking yourself if you want BOTH the present and the future of the life you’re living.
Because you’re not only betting on today.
You’re betting on tomorrow too.
3) Let Go of The Dream
You’re not the same person you were 12 months ago.
Life happened. You changed. Your personality evolved. Your needs morphed. Your ambitions shifted. It’s called being human.
But, along the way too often we forget to update our dreams to reflect the person we’ve become, tying ourselves to the desires of the past.
To quit on today’s terms, you need to let go of yesterday’s dreams.
Do this by asking yourself:
“Do I fully understand the sacrifices that I’m making?”
“Do I want every part of the dream I’m building?”
“Is there another dream pulling me tighter?”
“What’s my gut feeling about this?”
“Do I fear the change? What about it scares me?”
When it’s time to let go your intuition will tell you.
Explore it, talk about it and see where it leads you.
#2: Identify Your Dead Ends 📌
“A woodpecker can tap twenty times on a thousand trees and get nowhere, but stay busy. Or he can tap twenty-thousand times on one tree and get dinner.” - Seth Godin
There are infinite number of paths to choose.
You could spend your days searching for treasure as a professional scuba-diver, selling your soul as an investment banker or scooping up the latest breaking stories as a freelance journalist.
With enough appetite for change you could do them all.
But, would you ever master a single one of them enough to reap the rewards of your efforts? And would those rewards be worth the investment of your time that could have been spent elsewhere?
For mastery takes consistent effort over a long period of time.
That’s why it’s crucial to identify your dead ends early.
Here’s how you do it:
1) Understand The 3 Curves in Life
There are three outcomes to your decisions.
In one the path becomes a dead-end leading you nowhere, in another the path continuously improves until it stops suddenly and in the third the path has a dip before the full rewards are realised.
The Cul-de-Sac
You continuously graft and graft, but nothing changes. Things don’t improve, but they also don’t much worsen. These are typically dead-end jobs with paths that don’t move you any closer your ideal future, trapping you in mediocrity.
The Cliff
You start to see the fruits of your labour early on and decide to keep pushing harder and harder until suddenly the short-term sacrifices catch-up with you. These behaviours are enjoyable, but have significant drawbacks if you fail. A clear example is smoking, which is enjoyable until you get lung cancer.
The Dip
You initially find learning fun until you start seeking mastery. To get there requires crossing the suffering that life will throw at you. This is the dip and it usually looks like being one month from going bankrupt, but deciding to double down by pushing harder towards your goal.
Anything worth doing involves a dip. The bigger it is, the less competition there is. Which makes you harder to replace and justifies your value. To reap those top rewards you have to be willing to push through when it gets hard.
2) Be Exceptional or Quit
1st place is rewarded 100x more than 2nd place.
They are the ones who get invites onto talk shows, sponsorship deals with the biggest brands and names tattooed onto their most loyal fans.
If your aim is to build a legacy, you have only one option:
Be exceptional. Or quit while you’re ahead.
If you can’t see yourself doing it for the next 20 years, free yourself to be great elsewhere. Then try new things until you can bring your skills together into a unique combination that no-one else can compete with.
3) Prioritise Learning over Everything Else
If legacy building isn’t your thing, then optimise for learning. Especially while you’re still figuring out what you enjoy.
Do this by listening into the choices that scare you the most.
Then run straight towards them. It’s in overcoming the fear and striving towards the next that you’ll grow the most as a person.
But, if you’re unsure whether you’re at the end of a cul-de-sac or in the dip of eventual success ask yourself these questions:
“Do I want even want this version of success?”
“Is exploring more important than mastery right now?”
“Will this path teach me how to become the person I want to be?”
There are many dips you could bare to reap the rewards.
But, which one could you enjoy step of the journey of?
#3: Get Clear in Your Decisions 🔎
“It’s a lack of clarity that creates chaos and frustration. Those emotions are poison to any living goal” - Steve Maraboli
Life is gonna get hard.
There will be days when it feels like the universe is against you, dragging her heels into everything you do, leaving you helpless.
Don’t quit on those days.
For the storm of the emotions will pass. The calm of the seas will return. Only then, once the waters are still, should you make your choice.
Here’s how steady your decision-making:
1) Give Yourself the Headspace
Making clear decisions means not reacting in the moment.
Instead, giving yourself the time and thought to get your head straight before jumping to any conclusions.
For reflecting can be drastically different to the present moment.
So, give yourself the headspace to think by:
Going for a walk round the block.
Booking a solo holiday to figure things out.
Taking your bike out for a ride in the countryside.
Jamming to your favourite tunes in your room.
Sound boarding your thoughts with your friends.
You’re not delaying the inevitable.
You’re simply acting, rather than reacting.
2) Set Your Quitting Boundaries
Define what will make you quit.
Get ultra-specific about what you would consider a dead-end and list them out clearly for you to refer back to.
Here are some examples:
If they belittle my experiences, I’ll quit.
If I can’t choose where I want to work, I’ll quit.
When I’m not learning 1 new thing a week, I’ll quit.
Don’t set your boundaries as time-frames.
Link them values or goals instead.
3) Start by Quitting Small
You don’t have to quit everything all at once.
The idea of quitting and then backpacking around the world for a year to find yourself might seem alluring, but it’s not the only option.
Instead, you can start small:
Quit working with that annoying client.
Quit the manager giving you the most hassle.
Quit staying for the after work drinks you don’t enjoy.
Quit sleeping in the same bedroom as your partner.
Quit playing video games every single day.
We love an either or solution. But, sometimes we need to realise that quitting the smallest things can often make the biggest difference.
So, change the tactics first. Then the strategy.
The Summary
Let’s recap: To master quitting you need to find your peace with failure, identify your dead ends and get clear in your decisions.
There’s your 5 minutes, now take action:
📚 Recommended Book: The Dip by Seth Godin - Godin gives you the mental models to help you quit before it’s too late. Well worth a read if your life aim is maximise the material returns of what you commit your time to.
🎤 Recommended Talk: Strategic Quitting by Paul Rulkens - A 12-minute dissection of how to manage your brain, when to quit and how you should go about doing it.
💎 Recommended Resource: How to Quit Your Job by HBR - All the steps to go through if you’re considering leaving your job and how to plan for what’s next.