When is the Right Time to Quit?

Why I left my dream job at Google after getting the highest rating twice

👋 Hi, this is Akash with this week’s newsletter. I write about leadership and growth in software engineering. Recently, we crossed 1500 subscribers! Thank you for your readership.

This week, I’m sharing how you can decide if it’s the right time to change your job. I have had four jobs, and every time, I switched for a different reason. We will explore how you can plan your career in a way that serves you. Hope you enjoy this edition!

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How many times do you question your decision to quit?

Do you feel:

• Am I changing jobs too soon?

• How will my new manager be?

• What if the new company is much worse?

Broadly, I divide quitting into two categories,

1. Happy quit

2. Rage quit

The first is when you start feeling your growth has stalled and want new challenges. The other is when you can’t stand working in your current team.

I’ve had a job where I felt disconnected the first day. The manager seemed a completely different person. And I felt, what the hell am I going to do now? (read questions to ask your manager to avoid this)

Most recently, I’ve left my job at Google because I felt content. All I could hear in my head was:

“Life begins at the end of your comfort zone” - Neal Donald Walsch

It is much more nuanced than that. Today, we will explore how you can quit more confidently.

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🎤 Announcement: New podcast episode

I highly recommend checking out this podcast episode. I share tips and tricks to accelerate your growth. We talk about taking control of your growth journey by asking specific questions.

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⭐ Main Takeaways

• Balance quitting at the first sign of distress with misplaced loyalty

• Questions to self-evaluate your situation

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😊 Happy Quitting

When we start a new job, we all want to get comfortable. We want to be:

• Part of the team

• Visibly contributing to larger goals

• Encouraged by personal development scope

I had all of these things when I decided to quit Google. My work had the highest visibility I could dream of, my team was no short of extraordinary, and my entire management chain trusted me. But why did I quit? I get this question a lot.

LinkedIn Post

After I announced my intention to leave, I had a career conversation with my VP. We talked about:

• How comfortable I felt in my role, and how used to I got with the culture

• How my work was making my thought process unidirectional

• My motivation to try out something different in the AI space, particularly

You don’t want to get too comfortable if you want to grow. I struggled to understand what being “too comfortable” meant. Now, I have more clarity. Try asking yourself these questions:

• “What are three new things I learned over the last 6/12 months?”

  • Learning new things is the only way to grow.

• “Do I feel confident about this/next quarter’s goals/ambitions?”

  • You’re looking for a “no” or a soft “yes”; a definite yes indicates work isn’t challenging enough.

• “Is my current work aligned with the vision I had for myself?”

  • For me, this was an easy “no”. I wanted to work on securing AI.

Ultimately, leaving a job is okay, even when everything’s going great. Just make sure you’re doing it for the right reasons. Don’t question your loyalty because you want to explore something new.

😠 Rage Quitting

Not everyone is happy in their current role. Are you struggling to stay afloat? I certainly was on multiple occasions.

🚸 Disclaimer: “Rage” is a strong word, but it means “unhappy” in this post.

Common reasons why people feel a strong desire to quit in such environments include,

• Toxic team/manager

• Insufficient growth

• Lack of vision

Imagine walking into your job the first day and feeling “cheated”. The job that was sold to you may be different from reality. I have had this happen to me twice. As someone who doesn’t like giving up, I’d not have it.

A few things were going through my mind,

• I am judging too quickly, and I’m wrong.

• What would the world think if I were to quit in a year?

• What can I do to turn this around? Maybe it’s a good opportunity?

Switching jobs too quickly is seen as a “red flag” in interviews. We often overlook people with shorter tenure to avoid hiring the wrong person. The true story behind the tenure usually goes unexplored.

This forces you to stay at a job where you’re unhappy for longer. We can’t change the hiring practices, but we can change how we approach this problem. I’ve benefitted by

• Giving myself a timeline (usually six months to a year) to avoid kneejerk reactions

  • But coming back to make the decision at the end of the period

• Sharing my concerns and struggles with an external mentor

  • This can be your previous coworkers, managers, etc.

• Solving the problems by working with my new leaders

  • It’s tricky as a new employee. But, surfacing your concerns early can be mutually beneficial.

Leaving a new job is always tricky and causes anxiety. Always prioritize your career and well-being. A bad environment affects not only your career growth but your mental health.

🎁 Bonus: “Once in a Lifetime Opportunity” Quitting

Beyond happy and unhappy scenarios, there are once-in-a-lifetime opportunities.

“Great opportunities don't come every day” - Matt Ehrlichman

There will be moments of opportunity in your career. Regardless of how happy or sad you are in your current position, you must seize them. It’s also hard to create a general framework because it’s personal. 

The key is to be self-aware. For example, if I wait for an offer from Amazon to lead their AWS business, I’ll wait forever.

Here’s how I determine whether it’s an offer I can’t refuse,

• It has the right mixture of challenge, risk, and security

• It takes my career to the next level

  • ✅ Lead a large division (>100 people) in Fortune-5 companies

  • ✅ Founding member for an early-stage startup aligned with my vision

  • ❌ Going from Staff to Principal (those are not a once-in-a-lifetime opportunity for me)

• The upside is more than 100X. If it works, I will never have to work for money again

Define your criteria now. Don’t hold off and be conservative; be reasonably ambitious.

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🌟 🔍 Parting Thoughts

You’re hurting your career if you’re taking too long to quit. It is important to have a clear understanding of what your current role offers and how it’s aligned with your aspirations. Today, we covered three scenarios,

• Happy quitting

  • “What are three new things I learned over the last 6/12 months?”

  • “Do I feel confident about this/next quarter’s goals/ambitions?”

  • “Is my current work aligned with the vision I had for myself?”

• Rage quitting

  • Don’t react; set a timeline (usually six months to a year) to avoid kneejerk reactions

  • Try to solve the problems by working with your new leaders

  • Share your concerns and struggles with an external mentor

• Once-in-a-lifetime opportunity

  • Create a personal, objective criteria to evaluate

  • Dream big, be ambitious, setting the standard

  • Never pass on; it’s rare

Let’s hear your stories of quitting.

Share them in the comments!

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🐦‍🔥 This Week’s Favorites

• Tips to deal with salary reviews from The Hybrid Hacker by Luca Rossi and Nicola Ballotta

• Uber tech stack from Junaid Effendi | Sharing knowledge for Engineers by Junaid Effendi

• Do you need certifications from The Hustling Engineer by Hemant Pandey

• Tips to get promoted from High Growth Engineer by Jordan Cutler and Ethan Evans

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👋 💬 Get In Touch

Want to chat? Find me on LinkedIn.

If you want me to cover a particular area of leadership, you can reach out directly to akash@chromium.org. 

If you enjoyed this content, please 🔁 share it with friends and consider 🔔 subscribing if you haven’t already. Your 💙 response really motivates me to keep going.