Déjà vu

Every conversation about me quitting goes the same way.

“Where are you headed next?”

Nowhere.

“Ah, so you’re starting a company.”

Nope.

“Then what are you going to do?”

The implicit question here is: how are you going to earn money? I give them my honest answer: I don’t know yet. I’m focused on crafting a life instead of making a living. But they don’t buy it. Who would leave Google without securing another position? Was he fired? Is he trying to keep his business idea a secret? The truth is much simpler: I’m playing the long game. I have conviction that if I focus on building a solid foundation, I can climb to greater heights and enjoy the journey along the way.

Though I was certain about my decision, it always nagged me that people weren’t convinced. I wasn’t concerned about the validation, but rather my own understanding of the plan. Einstein famously said, “If you can’t explain it simply, you don’t understand it well enough.” So, I wrote this essay - to refine my thoughts, share my experience for those in the same boat and, most importantly, save me time at dinner parties.

An Intentional Life

Good decisions require sound frameworks. In this case, that meant determining the characteristics of a meaningful life. This was a necessary investment. It not only enabled me to take the leap, but will continue to act as a measuring stick to evaluate future decisions.

Principles for an intentional life.
Principles for an intentional life.

Note: It goes without saying that this is my personal definition. I am not asserting that this is universal. I acknowledge that it may evolve, but I don’t expect it to change significantly. It is the outcome of years of reflection on mistakes, regrets and treasured memories. Rather than hypothesizing its completeness, I want to validate it and iterate.

Health & Happiness

Have a long, lucid and content life. Be present to experience life in its richness. Enjoy the journey. This requires mental clarity, positivity and vitality. Negative emotions and energy levels must be managed. Put your oxygen mask on first - this is foundational to being effective.

Effectiveness

Get the right things done. No wasted time - make space for what matters. This requires prioritization, focus and productivity. Distractions, procrastination and lethargy must be managed. Mental clarity, energy levels and resilience to negative emotions from the previous layer are foundational.

Relationships

Deep, meaningful connections with friends and family. Quality over quantity.

Experiences

Play the minigames and maximize flow. Life is short, and there’s a lot to experience. Why go without trying as much as you can? Working all week and watching Netflix/scrolling Instagram in the spare hours is not my idea of a life well spent. A few items on my bucket list: build my own house, thru-hike the Appalachian Trail, do a stand-up comedy special.

Impact

Leave the world better than you found it. The world is entropic; it decays if left unattended. Yet, instead of yielding to the entropy, we relentlessly pursue progress. This has always inspired me, and I consider it my duty to leave a mark on society.

Work Didn’t Work

As the framework came into focus, it became clear that a traditional job wasn’t a good fit. There was little overlap between the life I wanted and the one that work offered. The benefits of being at Google - money, status, conventional success, fancy perks - weren’t factors in a meaningful life. On top of that, too many aspects of working life actively conflicted with my goals.

This was not a Google-specific problem. Though it has its own unique issues (there’s no shortage of similar articles), on the whole it arguably provides more opportunities for a meaningful life than other employers. But it still wasn’t enough. This was a crucial observation - if even the “best” job didn’t meet my needs, I was left with no choice other than to forge my own path.

By constraining your time, a full-time job limits the nature of experiences you can have. It imposes a schedule that your entire life has to fit around. Every decision involving time has to pass the “let me check with work” test. That means your time is not yours - you borrow it from your employer. Even when they magnanimously grant you precious vacation days, you have to get permission to use them. At least they’re gracious enough to let you have evenings and weekends, right? Well, just hope there isn’t an important deadline. You don’t have any alternatives either. You can’t work 20 hours a week. You can’t take a 3 month vacation every summer. You can’t skip one day because you didn’t feel like it. With your life fragmented into 4 hour evenings and 2 day weekends, it leaves little room for unique, immersive and valuable experiences.

“That’s still plenty of time left over.” (For the sake of the argument, let’s ignore the fragmentation.) On paper, yes. In practice, work was too draining. Afterwards, I couldn’t do anything that required my willpower. I paid my dues, I told myself. I deserve to not do anything - I need to recharge. Now, I get to lie back and watch reruns of Seinfeld. (Let’s be honest, even picking a new show is too much effort.) But this was just an escape, not a solution. The exhaustion was taking a toll on my happiness and effectiveness. If the purpose of a job is to provide money as a proxy for freedom, what is the point if it doesn’t leave the time or energy to exercise that freedom?

“You didn’t try hard enough to make it energizing.” Sure, I could always have done more. However, some fundamental qualities of work limit how inspired you can be. Firstly, it’s monotonous. Specialized work means less creativity and variety, which are essential to our well-being. Secondly, there is a lack of choice. In the best case, you have “autonomy” within a well-defined boundary. Just try not to bash into the walls too much. In the worst case, you’re directly told what to do. Either way, you have a gun to your head - motivate yourself to work on something that you didn’t choose or live with the cognitive dissonance. This is a lose-lose proposition - motivation must be intrinsic.

Corporations also challenge my principle of making the world a better place. Business impact is always the priority and social good is just the cherry on top. Don’t get me wrong - we always thought hard about how our products affected people. Probably even more than other companies (*cough* Facebook *cough*). But they were never equal criteria in decision making. Win-wins are ideal, but solely business impact is sufficient. This is working as intended for a data-driven company: it increases shareholder value and can be easily quantified. Improving the world can’t. And when it’s not the thing you’re optimizing for, you’re bound to get sub-optimal results.

What I’ll Miss

I’ll certainly miss aspects of work, from a steady paycheck to the creature comforts. However, even they have their own tradeoffs that nudge the decision in favor of leaving.

A steady paycheck provides stability that you can’t get otherwise. Even if you own a successful business, it is inherently unpredictable. It can be profitable one month and lose money in the next. You are responsible for its successes and failures. In a traditional job, you’re shielded from this. While the sense of security is comforting in the short-term, it comes at the cost of independence in the long run. When you’re reliant on someone else for your livelihood, you’re not in control of your own destiny. You’re truly free when you can earn a living otherwise - only then is a job an option instead of a foregone conclusion.

I’d be remiss not to mention the famous perks. Delicious, nutritious and - most importantly - free gourmet food. Well-equipped gym with classes from experienced coaches. Lively office spaces with thoughtful touches. Regular talks with thought leaders, artists and athletes. Oh, and the massages. A truly genius move on their part: offer employees one free massage a year ($60 value) and get unlimited free press in return. But I digress. While the perks were extraordinary, it would be penny-wise pound-foolish to focus on them instead of the significant trade-offs being made - no amount of nap pods, sushi or celebrity talks can fill a void left from unfulfilling work.

What’s next?

My thesis is that if I focus on enjoying the journey, everything else will follow. This contrasts with my past life, where I staked my happiness on future outcomes. Spoiler alert: they never pay out like you expect. The solution is to focus on the basics - be happy first and then you can accomplish anything.

Foundation First

Foundations are a collection of healthy habits that yield compounding returns. A strong one acts as a force multiplier. A weak one creates drag.

My priority is to establish a strong foundation first. This is because changing habits is expensive, but maintaining them is cheap. Frontloading the cost lets me fully harness the power of compounding. The most effective way to achieve this is to focus on building only a few healthy habits at once. This allows me to capitalize on two forms of leverage:

  • Keystone Habits: Each new habit forms a stable footing on which you can add other habits with little effort. This results in a multiplier or domino effect.
  • Sharpen the Saw: Each new habit is a data point in the feedback loop, helping me cultivate the meta-skill of building habits.

Health & Happiness

Instead of identifying the “correct” set of habits from the onset, I decided to start somewhere and iterate with a tight feedback loop. Learning from my mistakes plays an integral role in this process. I check in with myself weekly and put the learnings in action the next week. Here are some questions that help me reflect:

  • Current State: Am I content? Am I alert and present?
  • Challenges: Did I experience negative emotions or low energy? Why?
  • Fix: Did not doing an existing habit cause this? If not, what new habits can help me overcome these obstacles?

This is the initial set of habits:

  • Healthy diet for longevity and managing energy levels.
  • Meditate to be present and develop equanimity. (2x/day)
  • Exercise for longevity, stress reduction and mental clarity. (3x/week)
  • High-quality sleep for longevity and managing energy levels. (8h/day)
  • Journal to process emotions and foster positivity. (1x/day)

“This doesn’t seem like much. Couldn’t you have done these while working?” On paper, yes. In practice, it wasn’t happening. And it wasn’t for a lack of trying. I know this is a short list, but sustaining habits takes time and energy. I had stints with each of these, but I needed them to play a more constant role in my life. At some point, I had to come to terms with it and choose what I valued more - my job or my happiness?

Effectiveness

To be effective is to do the right things. The most common failure modes are not getting anything done (god bless Netflix) or drowning in busy work, unable to make room for what matters. There are two parts to doing this correctly: prioritization (right things) and execution (do). To determine the “right things”, I need a comprehensive view of all tasks and a prioritization process. To “do”, I need to create the space to act and unlearn old, destructive habits: lethargy, procrastination and seeking distractions.

If this sounds vague, it’s because I don’t have a solution yet. I just have a problem statement and a set of requirements. The plan is to discover the solution through iteration, using the requirements as a rubric. Since you can’t test a productivity system without tasks, I’m bootstrapping the process by working on several projects. The primary objective is to hone the skill of effectiveness - since it’s a transferable skill, this is the highest leverage work I can do. The added benefit is the success of the project itself. Take this blog for example. It primarily forces me to cultivate my own productivity, but also helps me refine my own thoughts (yet another feedback loop) and exercise my creative muscles.

Similar to the previous goal, I am using tight feedback loops to accelerate my progress. Here are some questions that help me reflect during my weekly check-ins:

  • Current State: What did I get done? What methods worked?
  • Challenges: What tasks did I misprioritize? What prevented me from working?
  • Fix: Did not doing an existing habit cause this? If not, what new habits can help me overcome these obstacles?

Relationships, Experiences, Impact

At this stage, the bulk of my energy is devoted to a solid foundation. However, I sprinkle this in to make the process more enjoyable.

Relationships: I make an active effort to have weekly conversations with non-local friends. The emphasis on non-local helps me maintain deeper connections over those defined by convenience/proximity.

Experiences: This self-improvement journey itself is very novel and exciting. The blog has also been rewarding. I’ve never written before, but it warms my heart that it has resonated with so many and given me the opportunity to connect with people I wouldn’t have otherwise.

Impact: My hope is that the blog influences others to live a more examined life.

Really, what’s next?

Let’s address the elephant in the room. What will I do for a living? I have no idea, but that doesn’t bother me at all. Here’s why:

  • I don’t value conventional success. I know this because I was unhappy despite monetary and career success.
  • I have a long runway. I saved a lot of money and have near-zero living expenses because I live in a paid off home.
  • I have no family obligations. I’m single (ladies???) and am not responsible for anyone. This is the best time to take a risk. This was indeed the biggest regret I heard from older colleagues - they wish they’d taken a chance before they had a family and a mortgage.

Ok, maybe that’s not entirely accurate. Though I’m not certain how I’ll make money, I do have a strong hunch about the problem space I’ll be working in. As I reflected on what prevented me from living a meaningful life, I noticed a very direct through line: an unhealthy relationship with technology. From the mental health drawbacks of social media to feeds limiting effectiveness to the ubiquity of smartphones preventing authentic connection and experiences, this is truly an epidemic in the making. It is the cigarette of our generation; it affects us, our parents and our children. We’re just beginning to realize the problem, but no one knows how to fix it. My plan is to start by using technology more intentionally in my individual journey, but ultimately I have conviction my learnings will be valuable to others. For such a looming problem, there is no shortage of value to create and capture.

What’s there to lose?

Quitting Google is an experiment that has unlimited upside and limited downside. My only cost is opportunity cost, while the payoff is an infinitely richer life. I call it an experiment because I acknowledge that perhaps I can’t have it all - maybe I’m idealizing post-work life and I took my previous life for granted. However, even failure would be a minor success. If I ever have to go back to a job, I’ll be able to better cope with it due to a solid foundation of health, happiness and effectiveness. Also, by experiencing both extremes I’ll gain the perspective to strike a better balance and will be immune to the grass is greener syndrome. As far as worst cases go, that’s about as good as it gets - it would have been crazy not to take the leap and see what happens.