The Plan

Two years ago, I quit my job at Google to craft a life instead of making a living.

“Sounds nice, but I have no idea what that means.”

Here’s the long answer.

The short answer - this is my definition of a meaningful life:

And this was my strategy to manifest it:

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.

Fast Forward

In the first year, I adopted healthy habits. First, I seriously committed to each habit for 3 months to understand the pros and cons. Then, I used that information to land at a sweet spot between value and effort. My experiments included 2 hours of daily meditation, a consistent weightlifting regimen and a strict diet that eliminated added sugar, fried food, refined grains and any other processed ingredients.

I also started Habit Gym, an accountability platform that helps people live a more intentional life through sustained reflection and action.

However, I wasn’t able to balance both very well. Some of my healthy habits fell by the wayside as I was building the business.

The goal of this year (Year 2) was to set myself back on track.

It was a modest success. I worked on my healthy habits and the business simultaneously. I developed resilience - I picked myself back up quickly after failing. As a whole, I’m operating at a higher baseline than I ever was.

There’s still room for improvement. Revenge bedtime procrastination, distractions and perfectionism to be challenges. Habit Gym is bottlenecked by distribution. In general, I need to get more serious if I want to succeed.

Let’s dive in.

Health and Happiness

“Two steps forward, one step back” sums up my progress with health and happiness this year.

I fell back on most of my goals. However, nothing went to zero. Each habit maintained a strong presence in my life, despite anything else going on. This was the year that I became certain that these habits are entrenched. They are here to stay.

Meditation

Goal: Maintain the practice.

Outcome: I had a brief lapse, which made me reevaluate the role of Vipassana in my life.

For the first year, I meditated for 2 hour-long sessions every day - no exceptions. This year, I broke the rule too many times.

Slippery slope

It started with my friend’s wedding in Nepal, which many of our mutual friends were also attending. I hadn’t seen them in person for years, some longer than a decade. I was tempted to squeeze in as much catching up as I could. Pair that with busy wedding festivities and you’re not left with much time. So I chose to scale the meditation down to a single session. A few days off never hurt anyone, right?

The break went on past the wedding. I was still in Nepal, staying with a close friend. Given we lived on opposite ends of the world, I prioritized face time. In between catching up on sleep, working on Habit Gym and hanging out there wasn’t much time to spare. So I continued a scaled down version of the practice. Anyway, I was scheduled for another 10-day retreat in a few days. I’ll reset after, I told myself.

Finally, it was time for the retreat. Unfortunately, I got a stomach virus hours before I was set to go. I powered through and luckily recovered a day into the course. Though I completed it, it wasn’t as effective as my first one. I’ll skip the details, but it was a combination of construction noise, disruptive participants and general facilities that hampered my meditation. It didn’t help that I started off sick and fell ill again on the last day.

When I returned to civilization, the excuses continued. I’m sick, so I should rest. It’s my last night in Nepal, so I’ll spend time with my friends. I’m on a flight; I’ll start when I get back. I even had a zero day or two. To my credit, I picked up where I left off immediately as I got back to New York.

However, the seal had broken. On a trip to California a month later, I broke the habit again. I was sick and I chose to rest. The time had to come from somewhere; I took it from meditation.

The reasons for skipping became progressively more trivial. When I moved in with two of my friends for the summer, I downgraded to a single session. I prioritized socializing and making use of the summer nights. I did the same on our trip to Patagonia, which included some zero days too. Every hour is precious, I justified to myself. It’s possible I’ll never be back here.

Why go into such detail about my experience? To illustrate how habits break. You’re probably thinking: “stop being so hard on yourself. One hour a day is still incredibly impressive”. (If I’m going to put words in your mouth, might as well throw in a compliment too.) I’m not being self-critical. I’m merely acknowledging the slippery slope of rationalization. If there’s one thing you take away from this, it’s that excuses creep up on you and eat into your progress. Don’t let them.

When I recognized this, I took action. Upon returning to New York and moving back home, I resumed the practice. I’ve been consistent since, back to 2 sessions a day.

Crack in the foundation

On further reflection, I found the underlying reason for my rationalizing. There was a crack in the foundation: I had started to doubt the value of the meditation.

Don’t get me wrong. I feel great. I’m balanced and at peace. Anger is now a rare emotion. When I get agitated, it doesn’t last very long. I liken my mental state to a body of water - even with the occasional ripple, I return to still shortly after. I certainly want to maintain this state.

The question was: is this the most efficient way to retain the benefits? Do I need to keep investing two hours per day or can I get away with less?

I was torn.

On one hand, Vipassana has truly changed my life. I vividly remember my transformation during the first course. I surrendered to the technique for 10 days and got the promised results. When they prescribed 2 hours of daily practice, I naturally abided by it. Sticking to the rules had worked well for me so far. Why question it? Plus, the tradition is thousands of years old. The advice must be rooted in experiential wisdom, I figured.

On the other, two hours is a lot of time every day. There are alternative techniques that many successful people advocate, e.g transcendental meditation. These don’t require the same commitment and seem to still be effective. But it’s hard to compare; they may serve different purposes.

I have mixed feelings about how to proceed.

A small part of me feels guilty for trying to “optimize” this. I was graciously taught the technique and greatly benefited from doing it exactly as I was told. Yet, I’m going against that very advice in the quest for efficiency. Intuitively, this seems like the wrong lens to look at meditation through.

I’m also confused. I’ve been practicing for so long that I don’t remember what my former state of mind used to be. There’s the tiny possibility that I regressed to my pre-meditative state after my first course, so gradually that I didn’t notice. More likely though, I grew so used to the peace that I forgot how chaotic my mind used to be. It’s not so different from how we take being healthy for granted until we get sick.

This concerns me. What if I’m underestimating the effect of Vipassana? I have a good thing going and there’s a real chance that I undo my progress. Am I flying too close to the sun by jeopardizing it?

Overthinking doesn’t help anyone, though. I need to take action.

This year, I want to get clarity on the question: what is the role of Vipassana in my life? This may include experimenting with new techniques, scaling down the practice or even taking a complete break.

This is a high stakes decision. There’s the risk that I may lose my benefits or the habit, even altogether. But if I’m in this for the long run, I need to eliminate all doubt. It’s a calculated risk. Having done it consistently for two years, I’m confident I can pick it back up when necessary.

Learnings and Goals

What I learned:

  • Rationalization is a slippery slope. The wedding was a valid-ish reason. After, they got progressively more trivial. You need to preemptively establish a hard line to not get carried away. Otherwise, you’ll keep moving the goalposts.
  • Tomorrow won’t be different. I kept deferring to the future, e.g after the wedding, after the retreat, after flying home. When the time came, I kicked the can down the road. If you don’t start now, you won’t start tomorrow.
  • Meditation is a constant. When I looked past the guilt of failing, I realized that I’m still regularly meditating for an hour every day. I’m proud of this baseline - it’s something I could never have imagined myself doing.
  • I am at peace. My default state is calm and composed. I liken it to a still body of water. Disturbances arise, but the ripples dissipate quickly. I don’t get as agitated and I return to normal quickly. The spikes of negative emotions are shorter and further apart.

Goal for next year: Go/no go decision on Vipassana.

  • (If go) Establish a hard set of rules for exceptions.
  • (If no go) Settle on an alternative practice to seriously commit to.

Diet

Goal: Eat more fruits, vegetables and probiotics for vitamins, minerals and gut health.

Outcome: I wasn’t intentional about it.

I vaguely identified when and how I would have them, but I didn’t actually carve out space in my schedule to do it. I was either too busy working or didn’t account for the extra time when preparing dinner.

For example, fruits are a midday snack. However, I was so zoned in while working that I wouldn’t step away from my desk to eat them. I took occasional breaks to browse the internet, but only because that didn’t require getting up. I didn’t want to break the flow. Also, it took less time… theoretically. A minute was enough to skim Twitter, but I needed 10 to eat fruits. Obviously, it didn’t play out that way. Fast forward 20 minutes and I was still on Twitter.

Same with vegetables. I didn’t find a good time for them. My meals were protein-heavy and didn’t have a ton of vegetables. I hoped to make side salads, but I never fit that into the schedule. Ditto for pre and probiotics.

This was a vicious cycle. Since it wasn’t part of the routine, I didn’t always have fruits/vegetables on hand. When I did, I would eat them but then forget to restock. As a result, the habit never got a chance to form.

On the whole, I was good about my overall food choices. I leaned towards healthier options, avoiding processed and refined ingredients.

I did a lot more traveling and socializing this year, so it suffered when I was away. While I was home though, I maintained my habits. I now have an established routine that optimizes my time and nutrition. I do all my cooking in the evening - tonight’s dinner becomes the next day’s lunch. At the same time, I make my overnight oats. All in all, it takes me 45 minutes a day to prepare all my meals.

What I learned:

  • Habits need a kickstart. You can either have a virtuous cycle or vicious cycle. If you maintain it carefully for the first few weeks, the habit will become self-perpetuating.
  • Routines work. I’m a creature of habit. I eat the same breakfast every day and make the same 5 meals every week. This system works. It takes less than an hour every day and offers enough variety to not get bored.
  • Revisit your goals regularly. Honestly, I had forgotten about this goal until partway through the year. I wrote it down here, but never followed up. If I had, I may have gotten further. To solve this, I added a weekly task (or scheduled interrupt) to revisit my monthly and yearly goals. I’m also going to start doing public monthly retrospectives.
  • Not all leisure is made equal. It’s easy to watch a video, but you regret it later. It’s harder to get up and make a snack, but it’s more rewarding. Focus on time well spent.
  • Beware of bite-sized distractions. They are pernicious. They lure you in as short indulgences, but end up consuming more of your attention and time.
  • Healthy food choices are now ingrained. When presented with two options, I choose the healthy one by default. I also go out of my way to find it. I don’t see this changing anytime soon.

Goal for next year: Add fruits, vegetables and pre/probiotics to my standard meal plan. (More specifically, have fruit and yogurt midday and a side salad for dinner.)

Exercise

Goal: Commit to exercising 3x/week. When dealing with an injury, I’ll substitute the exercise routine instead of just waiting to recover.

Outcome: I met the goal, with the exception of traveling.

I invested in my body. I was recovering from a shoulder injury, so I did PT to get it back on track. While the rehab was taking place, I ran consistently. Now, I’m ready to get back to lifting.

What I learned:

  • Adaptability is crucial. As a creature of habit, I get thrown off when anything disturbs my routine. This response isn’t healthy or sustainable. Setbacks are unavoidable. They’re out of your control. In order to survive, you must learn to adapt.
  • Adaptability can be learned. It’s a skill, like anything else. You don’t have to be a natural. It’s difficult at first, but improves with practice. For example, the exercise goal pushed me out of my comfort zone. My default tendency is to defer when conditions aren’t perfect, e.g dealing with an injury. Adapting taught me that you can always salvage the situation.
  • Hobbies aren’t found, they’re built. If you asked me 3 years ago, I would tell you that I hated running. Now, I love it. Same with writing. All it took was a few runs or essays to discover their joy. Satisfaction is on the other side of effort. You’ll never find it until you push through.

Goal for next year: Exercise 3x/week. Get back to weight training when healthy; substitute it for another form if injured.

Sleep

Goal: Enforce a more consistent sleep schedule.

Outcome: It suffered for most of the year, but I’m settling into a good groove now. Revenge bedtime procrastination and lack of external accountability continue to be challenges.

Socialization was the main obstacle that stood in the way of a healthy sleep schedule. This was true while traveling and living with my friends for the summer. It didn’t help that intoxicants were occasionally involved. Nothing crazy; it was all legal and in small doses, but I discovered that sleep is especially sensitive to them. I relearned that this has a cascading effect. Waking up later leads to tiredness which results in lower productivity. It also pushes your sleep cycle later, which prolongs the consequences.

I continued to struggle with post-lunch sluggishness. I stopped my afternoon walks since I would sometimes come back just as drowsy. Instead, I replaced them with power naps and was effective in containing them to 15 minutes. Well, mostly. I’m embarrassed to admit that there were more than a few exceptions. As a solopreneur with an open schedule, I didn’t always have the discipline to wake up on time. This is as true for the morning as it is for afternoon naps.

In a way, this is working as intended. I anticipated these kinds of challenges when I quit. I left Google in order to cultivate intrinsic motivation. I figured that the only way to be truly independent - personally and financially - was to learn to hold myself accountable instead of relying on someone else.

That being said, I’m not happy with my progress in this regard. I have a long way to go. I need to do better if I’m going to succeed. And I have been, recently. I have a much more consistent bedtime. Though I don’t always stick to it, I also have a stronger understanding of my sleep habits and how they affect the next few days.

My biggest challenge is revenge bedtime procrastination. 10pm seems too early to unplug. I feel as though I haven’t had enough “fun”. It’s my only time to unwind, so I don’t want to disconnect. I associate putting my devices away with getting ready to grind again.

In the upcoming year, I want to eliminate this resistance. I suspect the solution lies in the lessons I learned from other habits, e.g exercise. At first, it may be uninteresting or even daunting. Once you do it regularly, it becomes part of your identity and you even begin to enjoy it. You go from being overwhelmed by the effort to focusing on the benefits that you receive.

What I learned:

  • Forcing functions are necessary. I used to avoid alarms so they wouldn’t disrupt my REM. I preferred to wake up naturally. The flip side of this was that I’d get up later than I should have. Now, I recognize their role as a forcing function. Setting a wake-up time deters me from rationalizing the next morning and sleeping in. The second-order effect is that it encourages me to go to bed on time. Ideally, I would have the willpower to wake up early without an alarm. That won’t always be the case, though. You need to understand your limitations and implement forcing functions to do what needs to be done; whether you like it or not.
  • Changes have to be gradual. You can’t upend your sleep schedule overnight. When I tried to suddenly start waking up at 6am, it didn’t work. It was daunting and not very restful. The more effective way is to move your wake-up time slightly earlier, week after week.
  • Early mornings lead to better days. I have a fixed overhead of self-care habits, e.g meditation, exercise, cooking. The later I wake up, the more it eats into my day. Getting up earlier allows me to get more done and avoid unproductive habits. As a result, I feel more accomplished.
  • Late night and early morning screens disrupt sleep. It takes me longer to fall asleep right after I put my phone away. I’m uncertain whether it’s the dopamine or the brightness, but it’s noticeable. It’s the same for waking up. When I look at my phone first thing in the morning, it takes me longer to fully wake up.
  • Follow your circadian rhythm. A consistent sleep cycle improves your sleep quality. When you go to bed is just as important as how many hours you sleep for. When I slept at the same time every night, I felt more well-rested in the morning.
  • Naps are ok. I used to beat myself up over mid-day naps. Now, I accept them. The truth is that they breathe new life into me. Sure, it’s not great to have a 1-hour siesta. But as long as I contain them to 15 minutes, they are productive.

Goal for next year: Maintain a consistent sleep schedule - 8 hours of high-quality sleep and wake up at 6am.

  • Experiment with ways to avoid post-lunch sluggishness, including walks, standing work sessions and contained naps.
  • Set hard rules for when intoxicants are allowed (maybe never).
  • No screen time before/after sleeping.

Journal

Goal: Maintain the weekly habit tracker and add free-form journaling.

Outcome: I maintained the weekly habit tracker and even added a daily check-in. I didn’t do any free-form journaling, but felt its absence.

My weekly habit tracker continues to serve me well. Reflecting regularly helps me identify weaknesses in my foundation and, by extension, surfaces actionable insights to get me back on track. Often, it’s the same lessons week after week. In the moment, it can feel like I’m stagnating. That isn’t so. The repeat failures are necessary; they instill valuable learnings. Change is slowly taking root as I chip away at the underlying problem. Up close, progress can seem glacial. Only when I zoom out and compare myself to a month or year ago, do I see how far I’ve come.

I added a daily check-in to augment my weekly tracker. I found that when I was reflecting on my week, the days would blur together. This made it difficult to evaluate whether I met my goals, e.g exercising 3 times. Sometimes, I would even lose track of what this week’s goals were. Daily check-ins solved both of these problems by ensuring I revisited my goals and logged my progress. They also acted as a hook for a gratitude habit. Every day, I mention three things I’m grateful for. It’s a small dose of positivity that uplifts me and offers perspective so I don’t get lost in the endless pursuit of self-improvement.

I didn’t make time for weekly journaling. However, I did feel its absence. A lot happened this year, personally and professionally, and I would have valued processing my emotions more directly. Though the meditation practice helped me stay balanced, there were still a lot of thoughts swirling around. Journaling would have helped me think through my decisions with greater clarity. It would also create the documentation to extract useful insights in the future. This is a priority for next year.

In addition to private free-form journaling, I’m starting public monthly retrospectives. I always learn a lot from these yearly posts and I would like to tighten the feedback loop. I expect that this will help me course-correct earlier and as a result, accelerate my growth.

What I learned:

  • You don’t find time, you make it. I can’t blame my schedule for not journaling; I can only blame myself for not making room in it.
  • Change is slow. You won’t always see the progress up close. As long as you keep chipping away at the underlying problem, change is taking root. You overestimate what you can do in a day and underestimate what you can do in a year.
  • Perspective keeps you happy. It’s easy to get lost in the details or the chase. Every now and then, it’s important to take a step back to see how far you’ve come and what you have to be grateful for.
  • Life is a blur. Days, weeks, months, years - they all blur together. If you don’t check in on your progress regularly, you’ll notice too late that you’re not where you want to be.

Goals for next year: Publish monthly retrospectives. Free-form journal every week. Maintain weekly and daily habit trackers.

Effectiveness

Goal:

  • Maintain my productivity system to adapt to the growing needs of the business.
  • Timeblock more effectively by iterating on the Pomodoro Technique and experimenting with alternatives.
  • Maximize hours of focused work by iterating on methods that have shown promise: fixed routines, the Pomodoro Technique and adding friction to distractions.

Outcome: My prioritization got better. I leveled up in execution. I still have a long way to go - perfectionism and distractions continue to be challenges.

Prioritization

I developed an even greater awareness of my issues, but my implementation leaves much to be desired. Perfectionism held me back. I kept going the extra mile even when I didn’t need to, e.g over-editing my posts or adding a nice-to-have feature on Habit Gym. This came at the expense of other important workstreams.

I was proactive at prioritizing my tasks on paper, but poor at sticking to it in practice. I didn’t always have the discipline to stop working on the finer details. As a result, these tasks bled into the time allotted for others. My output suffered. By the end of the week, I would rarely accomplish everything I had set out to. Important areas that weren’t time-sensitive were particularly neglected.

This prompted a question: am I simply being inefficient or do I need to reset my expectations about what can get done in a week? The answer is likely both. If I can prevent myself from getting lost in the weeds, I’ll be able to extract 80% of the results with 20% of the effort (see the Pareto Principle). At the same time, I also need to narrow down my weekly goals. When you have too many priorities, you have none.

I believe sequencing will play a key role here. Doing the most important tasks at the beginning of the day can solve both of these problems simultaneously. It ensures that the critical work gets done instead of being carried over from week to week. It also timeboxes the less important tasks so there’s no room to get carried away with perfecting smaller details.

I’ll also need a more realistic estimate of my throughput. I expect the Pomodoro Technique to come in handy here, especially with repetitive busy work. Over time, I’ll learn how long each task takes and can account for it while planning. If I do this well, I’ll be able to make meaningful progress on several fronts without dropping the ball on any of them.

Execution

I leveled up in my execution. Pomodoro work sessions were a massive unlock. I began doing them to measure my writing time and, as I expected, it became a keystone habit. I quickly adopted them for the rest of my projects.

They allowed me to timebox and quantify my effort. The latter turned out to be a critical diagnostic tool. Equipped with a new metric, I have greater visibility into the impact of my habits on my productivity. What gets measured gets improved.

In the past, I only had a rough sense of how much I was working. As the days blurred together, it became a challenge to separate good weeks from bad ones. This made it difficult to debug the root cause of poor performance. You can’t rely on your self-assessment either. Productivity is highly subjective - there’s an inherent bias towards visible results. The day you launch a new product or publish a viral post brings a stronger sense of accomplishment than the weeks of effort you put in to make that a reality.

With the ability to quantify time spent, I now have an objective measure. Only my effort counts, not the outcome. After all, it’s the only thing you have control over. (Of course, that effort has to be invested towards the right goals - that’s where prioritization comes in.)

One example of a bad habit that affected my productivity: using my devices as avoidance mechanisms. Now, I can track my improvement through the number of work sessions I get in during the weekdays. My findings: it continues to hold me back in a big way, but it’s steadily decreasing.

Learnings and Goals

What I learned:

  • What gets measured gets improved. The small act of gathering data regularly has a profound subconscious effect. You begin to change your behavior in subtle ways to improve that. Once I started measuring the number of work sessions, I became more productive because my successes and failures were more visible.
  • Defaults are strong. When I disable YT on my phone, my screen time reduces. If I enable it temporarily for a valid reason, I often forget to block it again and my screen time shoots up. Add a scheduled interrupt to revisit these blocks so you make the defaults work for you.
  • Timeboxing prevents perfectionism. When the Pomodoro timer is running, I feel the pressure to complete my task before it ends. This forces me to make faster decisions and keep moving, instead of focusing on small optimizations. See Parkinson’s law: “work expands so as to fill the time available for its completion.”
  • Context switches are expensive. Batching helps reduce fragmentation. Doing a lot of small tasks together will save time.

Goal for next year: Get the right things done.

  • Get disciplined about prioritization through rigorous timeboxing, batching and sequencing.
  • Maximize focused work hours by eliminating distractions and developing a more consistent sleep schedule.
  • Work 7 hours a day according to plan.

Relationships

Goals: Increase breadth by reconnecting with 20 people. Spend 30 minutes with family every day.

Outcome: I deprioritized the first goal. I did the latter for a brief period. I doubled down on my close relationships.

I felt stretched this year, so I deprioritized the breadth goal. I still reconnected with many old friends, just at a more organic pace.

Instead, I doubled down on existing relationships. I moved into a Manhattan apartment with two of my childhood friends. I had friends from SF and Seattle stay with me for extended periods of time. I traveled to visit friends in Chicago and Nepal. I spent more quality time with my family. I got into a serious relationship.

Other than wanting to consistently spend time with family, I’m happy with this part of my life. Though I would like to do more relationship-building, I’m going to focus on the business this year.

Goal for next year: Continue to nurture my existing relationships. Don’t let them decay while being heads down.

Experiences

Goals: Do something new twice a month. Prioritize depth over breadth.

Outcome: I wasn’t intentional about actively doing something new. I prioritized depth over breadth across several areas.

This year was full of experiences.

I moved to Manhattan for the summer with two childhood friends. I witnessed 4 of my dearest friends getting married to the love of their lives. I stayed in Nepal for a month, where I attended another 10-day silent meditation retreat in the mountains. I visited Patagonia to do the W trek: a 100 km hike.

Though I didn’t do something new twice a month, I had a healthier attitude towards my burn rate. I didn’t let it hold me back from experiences. Living in Manhattan was a prime example. It put me in the red, but in the grand scheme of things it was a once in a lifetime opportunity. You never know when your friends are going to abandon you get hitched.

I did prioritize depth, however. I was in a serious relationship for the better part of a year. I relocated for a few months to enjoy summer in the city with my friends. It was full of Central Park runs, bike rides around town, Spikeball, comedy shows, outdoor movies and hiking. I “became” a writer and started publishing an essay every week.

As with my relationships, I’m happy with this part of my life. I don’t want to do more, since I’m focusing on the business this year. In fact, I may even turn it down a notch. While they are beautiful, they can also be distractions.

Goal for next year: Be more selective with my experiences. They should provide enjoyment without distracting me from my long-term goals.

Impact

Goal: Scale it. It creates significant value for users and gives me an opportunity to authentically capture part of it.

Outcome: I didn’t reach the scale that I aspired to, but I’m proud of the impact my writing and Habit Gym have had.

Many people have told me how my essays inspired them, from small acts like calling friends on their birthdays to bigger questions such as finding meaning after quitting their job. A lot of them are people I already knew. Funnily enough, writing for the public has brought me closer to my own friends.

The results from Habit Gym have been wonderful too. Hundreds have done it and benefited, with many of them sticking around. Some comments that warmed my heart:

  • ”I feel that I can accomplish anything I set my mind to.”
  • ”Completely changed my life. It’s actually kind of mind-blowing to think it’s only been a month”
  • ”This has been the best program I have come across in a long time.”

If it sounds like I’m tooting my own horn, know that the numbers here aren’t huge. At times, I’m disappointed by this. It’s a remnant of having worked in tech. The industry has an uncanny ability to convince you that anything less than a million users isn’t worth it.

“A million dollars isn’t cool. You know what’s cool? A billion dollars.” - Sean Parker

I have to periodically remind myself that it’s still meaningful to impact a handful of lives. They aren’t just numbers on a screen: each unit represents a human being with a life as vivid and complex as your own.

This isn’t to say that I don’t value scale. Helping more people is a win-win: I can create significant value and authentically capture part of it. It’s just important to take a step back and remember everyone you are continuing to help.

Goal for next year: Scale it even further. Reach an audience of 1m people through my work.

If that sounds ambitious, I’ll leave you with this. “Shoot for the moon. Even if you miss, you’ll land among the stars.”

Business (Habit Gym)

This is a top-level priority because it bankrolls all of the above. Without it, I wouldn’t be able to invest in my foundation or relationships, experiences and impact.

Goal from last year: $5,000 in monthly revenue.

Outcome: Revenue stagnated, but became more consistent as the subscription business grew. Distribution continues to be a bottleneck.

For context, Habit Gym is an accountability platform that helps users build healthy habits through sustained action and reflection. To learn more, check out the manifesto or the website.

Escape Velocity

Evaluating Habit Gym’s performance is challenging. From a revenue perspective, it stagnated. From a product perspective, it’s finding its groove. It’s not where I hoped, but it’s set up for success.

In the first year, I was working with a barebones MVP. I was using Google Forms for weekly check-ins, Discord for community, Stripe for accountability and Apps Script for emails. They were all tied together with custom software.

This worked well to validate the idea with early adopters, but I hit a wall soon after. It wasn’t very customizable and it limited my iteration speed. It wasn’t very seamless, either. Mass-market consumers needed a more polished experience.

This year, I finally launched a full-featured product and things are looking up. There is a highly engaged subscriber base that is consistently benefiting from the product. For programs with an active community, network effects are in play. The service is becoming stickier and more valuable with each incremental user. Retention is high and churn is low.

In retrospect, I should have done this much earlier. I overestimated the time commitment of building my own app and underestimated its flexibility. I thought relying on established external services would allow me to iterate faster; the opposite was true.

I am much more nimble with my own software. I have full control over every feature and can experiment more freely. This drastically increased my velocity. It allowed me to test hypotheses quickly, build a seamless experience and convey a sense of forward motion for existing users.

For next year, velocity is my biggest priority. I haven’t moved fast enough. After working on Habit Gym for 18 months, it’s not a clear success (or failure). That’s too slow. The opportunity cost is too high for me to be stuck in a state of limbo. I only have a limited window to build a sustainable business.

The solution is in the advice I received from fellow founders. They all shared a common mistake they made: pivoting too late instead of too early. For me, this means diversifying my efforts.

First, I’ll be launching new businesses. The hope is to create an ecosystem of products that are symbiotic. This is a reasonable assumption since they have a shared origin: my unique, personal worldview.

Second, I’ll continue to grow Habit Gym. It’s in a good place to run in the background. The concept has been proved out and the product doesn’t require much maintenance. With more scale, it can become a viable business. This year, I want to drive more people to it.

Distribution

My primary bottleneck has always been distribution. If I want to gain customers, I need to widen my funnel. There are four channels to consider: partnerships, paid acquisitions, viral growth and my own audience.

Partnerships

My initial strategy was to partner with self-improvement creators. It was a simple trade. I offer them a way to authentically monetize with habit-change programs and in return, I take a cut.

It was a no-brainer for them, I thought. They get a recurring income stream with no ongoing effort, an engaged community of their loyal supporters, a tool to gather insights on their audience’s biggest pain points and a way to elevate their impact from inspiring content to real change.

I was surprised when this approach didn’t work. I didn’t get traction with too many creators. The issues ranged from being hard to reach to their lack of bandwidth to simply not being interested in the product.

I attribute the lack of success here to two things: not having a mature product and incorrect expectations about cold outreach.

Now that Habit Gym is more polished, it should be easier to get my foot in the door with a compelling demo.

I also have a better understanding of the cold intro game. Initially, I was disappointed by what I thought was low conversion. Upon talking to people in the industry, I discovered that it was actually above average - the normal hit rate is just very low. That means I need more shots on target. I have to reach out to hundreds of potential partners, not tens.

Simultaneously, I also want to test out the other channels.

I hesitated to run ads for several reasons.

One, I was keeping my expenses low. A small part was vanity - I was proud of the business being profitable and I didn’t want to jeopardize that label. The rest was about maximizing runway. The more I spent, the less time I had to build a business. Recently, I realized that this is the wrong approach. It’s not just your funds that are capped; your time is limited as well. Moving fast and invalidating ideas is an equally important priority.

Two, I was relying on organic growth. I figured that if users benefited, they would share it with their friends. It’s hard to tell why this isn’t the case. My current hypothesis is that no one in their network shares their commitment to self-improvement, hence why they look to us for accountability in the first place.

Three, it isn’t my domain. I had never done ads before. It would add extra overhead that took time and energy away from cheaper and possibly more effective channels.

Though I don’t expect it to be my bread and butter, I’m going to try advertising. I suspect it will help me reach my target audience faster. Now that I have a better idea of my customer lifetime value, I can contain the downside too. Who knows what I’ll discover: perhaps it is the only way to scale this business?

Worst case, I’ll lose some money or break even. I’ll write it off as a learning expense. This is a skill that I expect will translate to any other businesses that I may venture into. It’s worth a small shot, at the very least.

Viral growth

I plan on doubling down on social features in Habit Gym.

I introduced some features in order to spur viral growth, but they weren’t widely used. I will continue experimenting along this dimension. I’m not just shoehorning features in for the sake of making it social, though. Fundamentally, I believe there is a real opportunity to add community to self-improvement. I just haven’t cracked how.

Too often, working on yourself feels lonely. The truth is that we’re all on the same journey and we all struggle with it. I’d love to peel back the curtain here. Wouldn’t it be beautiful if you could inspire and support your friends as they’re trying to improve?

This would be more positive-sum than traditional social media, where everyone’s busy playing status games and hiding the difficult (read: authentic) parts of their lives. This is known as the highlight reel problem: when people only share their happiest moments, it leads to unhealthy comparisons between your worst and their best.

By destigmatizing failure, I believe Habit Gym could be the antidote to this.

Build my own audience

If I have my own audience, it’s likely they will resonate with the product. Building it will be a big priority. More on this in the next section (writing).

Learnings and Goals

What I learned:

  • Time is precious. Time is a non-renewable resource. Use it wisely. Invest in growth and learnings to save you time and level up. It pays for itself.
  • Success is not the only measure of progress. Judge your progress based on ideas tested, not how many of your them succeed. You need to get through 100 ideas that don’t work to get to the 1 that does.
  • Distribution is key. It doesn’t matter how good your product is; it won’t succeed unless you get it into people’s hands. This has never rang more true: “First time founders are obsessed with product. Second time founders are obsessed with distribution.”
  • Prioritize agility. Being lean is good as long as you’re agile. When it starts holding you back from rapidly iterating, reconsider.

Goals for next year: Build a sustainable business.

  • Habit Gym: experiment with different engines of growth, e.g paid ads, partnerships, viral growth.
  • Diversify with other businesses.
  • Reinvest all my earnings to accelerate growth.

Writing

This deserves its own section because it played a profound impact on my life.

I started this blog when I quit Google.

In the first six months, essays took me ages. I needed them to be perfect and would constantly rewrite them. As a result, I only wrote 6 articles. It paid off, though. They were well received and gave me the confidence to continue. This planted a seed.

Then, I took a year-long break to focus on Habit Gym. I didn’t have the bandwidth to write while working on the business. In the meantime, essay ideas kept percolating. I kept them in the back of my mind, knowing they could have a home on the blog eventually.

Six months ago, the buffer overflowed. I had a backlog of ideas that I was desperate to write about. In conversations with friends, I found myself describing, labeling and repeating my own personal frameworks. I was often incoherent and rambly, but I knew there were nuggets of insight buried within.

Teach in order to learn

Why not kill two birds with a single post? I could succinctly articulate the idea and make it easily shareable. This would allow me to scale myself and simultaneously act as a memory aid device.

Writing forced me to understand my own concepts with great clarity. Not only could I explain them better, I didn’t need to walk through the argument again - the lesson was immediately clear from the title of the post. I was creating a personal glossary of concepts that I could immediately recall.

This supercharged my own growth as I internalized the lessons I wrote about. When I resisted a task because it was difficult, I reminded myself that the “only way out is through”. When I was tempted to skip flossing for yet another day, I reminded myself that “habits have inertia”. When I hesitated to publish another post because it wasn’t good enough, I reminded myself that “quantity is quality”.

Keystone habit

At this point in time, I was also in a rut. Habit Gym was doing ok, but it wasn’t where I wanted it to be. I had just come back from a month in Nepal, where my healthy habits languished. I was distracted by my relationship and apartment-hunting with friends. I needed some stability. A routine to get me going again. A keystone habit.

I chose writing. In May, I committed to publishing every week. Intuitively, this felt right. By making a public commitment, I’d be held accountable (by you). It would also enforce a routine that I could build off of. A prime example is using the Pomodoro Technique for my writing sessions and extending that to my remaining projects. Finally, it was just something I missed doing.

I truly believe I’ll look back at it as a life-defining moment.

Becoming a creator

I never wanted to be a “creator”. I associated them with scammy practices: clickbait content, pushy marketing and paid endorsements. I didn’t want to get on the hamster wheel of content creation, either.

As I started publishing more, I saw there was another path. I can be a creator, but in my own authentic way. I can achieve a balance that serves me and creates values for my audience.

Take this blog. I love writing here. It allows me to refine my ideas. It forces me to reflect on my journey. It lets me scale myself by sharing my experiences and learnings with others. It’s as valuable to me as it is for the readers, if not more.

As long as I’m being authentic, I can’t fail. At the very least, my writing will be useful to me. In the best case, others will benefit from it too. If they do, they are likely to share my worldview and resonate with whatever I build.

It’s already happening with Habit Gym. Readers discover it through the blog and register. This feels honest. It’s not some external product that I’m shilling. It’s a service that I deeply believe in. In fact, the way it’s designed only allows it to succeed when its users do.

Unlocking my potential

I made a lot of progress this year. I wrote faster and with greater clarity than ever before. I largely overcame my perfectionitis. I am comfortable publishing my work even if it doesn’t always feel “complete”. I discovered new techniques to get around writer’s block.

I still have a long way to go. My posts take longer than they should. My writing could be even clearer. I can increase my output.

Next year, I’m going to unlock my potential as a writer. I have conviction that making this a first-order goal will yield outsized returns in my life.

It will expand my arsenal of ideas for living an intentional life. It will improve my general communication skills. I will create value for orders of magnitude more people and be able to capture part of it. Best case, it becomes a valuable funnel for any business that I start. Worst case, I gain a new skill that carries over to many other dimensions of life.

Goal for next year: Publish with regularity.

  • Focus on improving quality and reducing time taken.
  • Actively experiment with techniques to optimize the writing process.
  • Build around a coherent theme.

Monthly Retrospectives

I mentioned this in the journaling section, but I’m calling it out here for extra accountability.

A common theme of the year is that I didn’t act fast enough.

When it came to some healthy habits, I neglected them and kicked the can down the road. Here we are, a year later, with little progress to show for those. In some cases, I even forgot that I had set a goal!

The same is true for Habit Gym. I regret not iterating more aggressively. I could have been further ahead if I was more nimble.

To avoid making the same mistake next year, I’m committing to public monthly retrospectives. This will hold me accountable to my yearly goals and ensure that I’m always moving the ball forward. If I’m not making progress, this will call attention to it and prompt an intervention.

These yearly reflections are always illuminating - I expect the monthly ones to be equally as insightful.

Do I want to keep doing this?

Yes, yes and yes. I love my life right now.

Of course I do. I have complete control of my time. I can invest in my mind and body. I spend quality time with my loved ones. I have unique experiences. I get to work on projects that excite me and make the world a better place. What’s not to like?

There’s one problem, though. This lifestyle isn’t sustainable… yet. I can only keep it up if I eventually build a successful business. Though I have a couple of years, I can feel the clock running down for the first time. The pressure is building up.

This was a much needed wake-up call. I was beginning to take it for granted. I wasn’t acting with urgency or pushing myself hard enough. I had almost become complacent.

That’s when it hit me. This was a regret in the making, possibly the biggest I’d ever have. I only have a tight window to make this work and I’ll always kick myself if I don’t maximize the opportunity. Having experienced this lifestyle, I never want to go back. That means the only way out is through. If I want to succeed, I have to be incredibly disciplined.

That’s the theme of the next year: ruthless prioritization in service of achieving my dream. I’m certain this is the life that I want and I’m going to make it work.

Here’s to another year of trying.

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This post took redacted minutes to write.

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