Last Updated on June 15, 2025 by Chin Yi Xuan
20 years ago (2005), Steve Jobs delivered his famous ‘Stay hungry, stay foolish’ Stanford commencement address.
One specific part of his speech still gets me thinking to this day:
When I was 17, I read a quote that went something like, “If you live each day as if it was your last, someday you’ll most certainly be right.”
It made an impression on me. And since then, for the past 33 years, I have looked in the mirror every morning and asked myself, “If today were the last day of my life, would I wanna do what I am about to do today?” And whenever the answer has been ‘no’ for too many days in a row, I know I need to change something.
In 2018, this was the video I watched before quitting my (one and only) full-time job to pursue content creation at No Money Lah.
Because ‘no’ has been my answer for too many months.
This week, I dedicate this newsletter to:
- Friends who are burnt out at work, and/or want to quit a toxic work culture
- You can’t imagine yourself doing this in the next 10, 20 years
- Your body and mental state need a break and rest from your intense workflow
The big question: How can you quit without feeling fear and anxiety?
Here are 3 questions to ask yourself before quitting:
Table of Contents
#1 Can you afford to quit?
Money doesn’t solve everything, but in this case – being prepared will put you in the position of choice.
Ask yourself:
- Do I have at least 6 months of living expenses saved? 12 months would be even better — and ideally, this should exclude your emergency fund.
The good news? Once you quit, your expenses will likely drop.
No more overpriced lunches, less money spent on transport and expensive coffee to survive soul-crushing mornings.
💡TLDR: Having enough savings will give you the space to rest, heal, and explore without being desperate for the next job.
—
RELATED: Freedom Floor: How do you know you’ve achieved Freedom of Choice in life?
#2 Is your current job affecting your mental health?
If your current job environment is drastically changing who you are as a person, where…
- You find yourself not smiling anymore
- You have trouble sleeping well
- Worst, you find yourself having dangerous or dark thoughts
Leave.
I am sure people who care for you will be more than glad to help you through this transition.
💡 Remember, no job is worth trading for your mental health.
#3 What are you going to do after quitting?
Ask yourself:
- Do I have a general plan or direction for my future path?
Generally, we’ll experience 3 phases upon quitting:
- Honeymoon phase: You enjoy the no-stress life of waking up without an alarm.
- Anxiety phase: You get anxious seeing your peers moving forward in their careers & lives – while you are still unsure about what’s next.
- Recovery phase: You now have a direction, and are working towards the new chapter in your career.
The reality of the Anxiety phase tends to hit harder for people who quit without a plan.
Hence, do this this before you quit:
- Decide on 3 goals that you’d like to pursue during this phase of life.
- It could also be courses to upskill yourself for the next phase of your career.
- You can also use this time to pursue activities that you are interested in.
- Also, consider the skills you’ve developed from your job. Are there skills that you can apply in your field of interest to create different possibilities?
Having a direction upon quitting will reduce your time in the Anxiety phase, and move you to Recovery phase earlier.
💡TLDR: Use your time with intention – be it to heal, or to improve yourself to discover new possibilities in life.
—
p.s. I recommend reading The 4-Hour Workweek by Tim Ferriss as you reflect on your career path.
Who shouldn’t quit (yet)
- If quitting means you won’t be able to eat or pay rent – you need a financial safety net first.
- If your job still gives you fulfillment, stability, and growth – you probably just need a holiday.
So… Should You Quit?
Not necessarily.
To be clear, this newsletter isn’t to encourage quitting.
But you can prepare, so you have the CHOICE to do so when needed.
Quitting is not the goal. The goal is to build a life that feels aligned and sustainable.
Start laying the bricks today – financially, emotionally, strategically.
So when the time comes, you won’t be jumping off a cliff.
Rather, you’ll be walking through a door you built yourself.
💭 I’d love to hear from you:
Have you ever thought of quitting your job? What’s stopping you – or what helped you take the leap?
Let me know by leaving your reply in the comment section, or DM me on IG – I read every message.
Cheers,
Yi Xuan
