Ups and downs

Forging your own path isn’t all smooth sailing. It’s a rocky road with many ups and downs.

February was one of those moments for me. It was the most challenging period of my journey so far, culminating in a full-blown existential crisis.

Here’s how it happened and what I learned about myself.

My trip to Asia

For all of February, I was traveling.

Two of my friends were getting married three weeks apart - one in India and the other in Thailand. Instead of making two separate trips from the US, I decided to stay in Asia for the whole month.

I used the opportunity to visit my friends and family in that part of the world, since I don’t see them often.

I reconnected with many friends from boarding school. Though I hadn’t met some of them since graduating, it didn’t feel like that at all. We picked up right where we left off. It was beautiful to see that our connection was still alive - you form a special bond when you live together during your formative years.

I also got to spend quality time with my extended family. We normally meet every 2-3 years at weddings, but it’s always rushed. Going without an agenda was a great way to connect on a deeper level. I’m especially grateful that I did this with my aging relatives. Every moment with them is precious.

Plus, I witnessed a celebration of love for two of my closest friends.

On the surface, this was a high point.

But deep down, I could feel the turmoil bubbling up.

Inner turmoil

It started slow.

It began with me dropping my goals, one by one.

I committed to 1 hour of daily meditation, but I stopped it the day I arrived in India. This was my first gap in two years. My justification: I planned to experiment with a break anyway and this was a good opportunity to maximize my time with my friends and family that I rarely see otherwise.

I was supposed to exercise weekly, but I only did it once in the entire month. My justification: I didn’t want to run in the pollution. To add to it, I got sick for a decent chunk in between.

I said I would journal on flights, but I never even took it out of my bag. My justification: I was sick on all my flights.

Sure, there were all semi-valid reasons. Still, I felt the guilt of abandoning my goals just days after I had set them.

It wasn’t only my personal goals that I gave up on. Habit Gym suffered the same fate.

I was meant to work on it in my downtime, but I just couldn’t bring myself to.

This was alarming.

I didn’t know how to explain the sudden loss of motivation. Sure, it could just be that I was on vacation and needed a break. Or that I chose to prioritize social connection while I was there.

But a growing part of me feared that it was permanent. Am I burnt out? Have I lost interest? Was I giving up?

I was afraid to confront these questions.

External pressure

Already in a vulnerable state of self-doubt, my external environment made matters worse.

Every family member I visited asked the same three things:

  1. When are you getting married?
  2. Why did you quit Google?
  3. What exactly do you do?

I was already grappling with these questions myself. I felt the stress of Habit Gym not fully taking off and how that affects me finding a life partner.

But now, I had to justify my decisions to them. (Indian families are very… inquisitive. Intrusively and persistently so.)

Having to repeat the same story 10 times just reinforced my concerns and added to the pressure I placed on myself.

On top of that, watching my friends get married made me revisit my priorities. I saw the value of being with someone that truly understands you and supports you in chasing your dreams.

I began to question my own path.

The original plan was simple: establish financial independence through a business and then find someone. In that order. At least, that was the ideal scenario.

But for the first time, I wondered: what if my business doesn’t take off? Is it worth deferring the search for a life partner until I succeed? Am I ready to put it off for an indefinite amount of time?

Both things are important to me. One, succeeding as an entrepreneur and two, having a meaningful long-term relationship. If I had to choose, I don’t know which one I’d pick.

And I was becoming increasingly worried that this was a choice I’d have to make soon.

To understand why, it’s important to know where I stand with Habit Gym.

A middling business

The state of Habit Gym is the primary reason behind this dilemma.

It’s middling. Successful enough that it doesn’t make sense to shut it down, but not so lucrative that I can live off it comfortably.

Every week, I watch it transform the lives of dozens of people. It helps them rebuild habits, reframe their attitude towards failure and rediscover what makes them happy. Yet, it’s not growing at the rate I want.

I liken it to a car stuck in mud. I’m revving the engines and the wheels are spinning. All it needs is an initial bit of traction to take off. Once it gets going, I’m confident it can propel itself.

Unfortunately, it’s been middling for a long time now. Naturally, the question arises: will I ever be able to get it out?

This is the first time I’m seriously asking myself this.

When I initially started Habit Gym, it was off to a hot start. I felt unstoppable. Everything was going swimmingly and my optimism was at an all-time high. When that’s the case, you don’t have these doubts.

But soon after, I hit a plateau. I approached the problem from several angles, but nothing worked. Every failure chipped away at my hope. Not succeeding became less and less hypothetical by the day.

Slowly, the concern creeps up: do I have what it takes to win?

My quasi-depressive episode

All of these thoughts circled around my mind as I headed home from my trip.

When I got back, I collapsed under the pressure. I had a quasi-depressive* episode. (I’ve never experienced this before, so I hesitate to attach a label to it). I could barely get myself out of bed for the first two days.

I felt overwhelmed and stuck. I didn’t know how to proceed.

How can I get Habit Gym on the right path? What are alternative projects if it doesn’t work? Is building a business even the correct priority?

I knew I couldn’t remain in this state of ambiguity. I needed clear answers.

First and foremost, I decided to take a break and clear my head.

When the dust settled, I sat down to write this post so I could get to the bottom of what happened.

It would help contextualize my concerns and reveal the root cause behind them. With that knowledge, I can reset.

What if I don’t succeed?

After playing back the past month’s events, the core concern became apparent.

My entire plan hinged on one outcome: building a successful business. Everything followed from there. The question was: what happens if I can’t?

Things don’t always go according to plan

For context, here was my grand plan.

First, I would quit Google to establish financial independence through a business that I start and own. Once that’s set up, I’d get married.

At that point, I would be free to focus on what matters to me: relationships, experiences and impact. Importantly, that includes time with my eventual partner and our family.

Easy peasy.

Unfortunately, you don’t always get what you want. I’m still stuck in phase 1 without an end in sight.

I drastically underestimated the challenge of getting a business off the ground. It’s a much longer and more uncertain process than I expected. I knew this to a small degree, but the full extent of it didn’t sink in until I was further along in the journey.

Don’t get me wrong. It’s not like I didn’t have a contingency plan. I did. But recent events made me rethink it.

Specifically, I didn’t appreciate how it would affect my search for a life partner.

Rethinking my contingency plan

The contingency plan was easy: move to a small city and live a simple life. In other words, declare Lean FIRE.

What is FIRE? It’s a lifestyle movement with the goal of gaining Financial Independence and Retiring Early. This is the essence of why I quit Google - to develop the freedom to spend time on what matters to me.

Lean FIRE is a minimalist branch of the movement. It prioritizes freedom over luxury. This often requires compromises such as not living in a major city or limiting expensive vacations.

The alternative is Fat FIRE, where you don’t compromise on lifestyle. The tradeoff is that it can take many more years of working to achieve the net worth required for it.

While Fat FIRE will take some time (and luck), Lean FIRE is achievable for me right now. I can move to a low cost of living city and support a family there, while having ample time for my own interests.

However, my last relationship made me reconsider it. Lifestyle was a major point of contention for us - she wasn’t down for the Lean FIRE life.

The more we discussed it, the more clearly I saw the tradeoffs.

We wouldn’t be able to live near my family in NYC. We’d have to think twice about certain types of vacations. Most importantly, we would be resource-constrained when providing for our kids. As an example, private school wouldn’t be an option. Though I wasn’t convinced it was necessary, having the optionality is important. You never want to feel like you couldn’t give your children the best upbringing possible.

All of these compromises conflict with my core values: relationships and experiences. Is the freedom really worth it if I can’t be close to family, provide the best for my kids or travel freely?

Ok, so Lean FIRE may not be viable. Then what?

One option is returning to a full-time job. But will I be happy? I certainly wasn’t fulfilled last time I was there.

Alternatively, I could wait until I’m financially independent. However, that can take an indefinite amount of time. Meanwhile, the dating pool dries up.

As with most problems in life, there’s no perfect solution. Each decision comes with its own risks. The question is: which path do I choose?

Being honest with myself

My answer is underwhelming: I don’t know… yet. I’m choosing not to decide right now. I’m kicking the can down the road.

Let me explain why.

My attention was in the wrong place. I was approaching the problem from the opposite direction. Instead of obsessing over the contingency plan, I should be laser focused on the goal: achieving financial independence.

If I can make a lot of money, I won’t have to make any of these compromises. I’ll get everything I want: freedom and lifestyle. That’s why I should aim for Fat FIRE.

I realized something about myself in this process. I had been limiting myself to Lean FIRE all this time due to a scarcity mindset. I was protecting myself by thinking small.

If I don’t set a lofty goal, I can’t fail. I was hiding behind this. If I told everyone, including myself, that “I want to make millions”, I would have to suffer the embarrassment if I didn’t.

This was absurd. I have an amazing safety net. I’ll always have a place to stay, food on the table and the company of people that I love.

What’s the point of all that security if you can’t use it to fully take the leap? When you let the fear of failure hold you back, you’ve already lost before you even began.

Of course, taking the leap doesn’t guarantee success. It’s necessary, but not sufficient. What happens, will happen.

That brings me to the second realization: I was focusing too much on the outcome.

My entire plan hinges on starting a successful business, but that’s not completely in my control. Some things are in my sphere of influence, others are not. Ultimately, I can only control my own input.

And if I’m being honest with myself, I haven’t given it my 100%. I became a tad bit complacent. I sense this is a regret in the making. I have to do my plan justice by putting in the work.

That’s why I’m deferring my decision. I want to go 100% on this path: high effort on a lofty goal. If I don’t make it, at least I’ll know I didn’t leave anything behind.

Regarding next steps, I’ll cross that bridge when I get there. I plan to revisit this at the end of the year. In the meantime, I can’t let myself worry about the future when I have the present to attend to.

What I learned

The two biggest takeaways from my experience are mentioned above: dream big and focus on what you can control.

Some smaller lessons that I learned:

  1. Take a break. Listen to your body. It’s important to push through sometimes, but cut yourself some slack when you need it.
  2. Retain perspective. Life is good. I have the basics that I need to be happy: shelter, food, health and loved ones. Don’t forget that when you’re aspiring towards larger goals.
  3. Ruts are a slippery slope. The longer you’re in it, the harder it is to get out. Take action early or the difficulty will compound.
  4. Life is an ongoing process. Just when we think we have everything figured out, it often falls apart. It’s a constant cycle of problem-solving.

Next Month

Here are my goals for April.

Health and happiness

  • Sleep for 8 hours. Wake up by 7am.
  • Exercise 4x/week.
  • Eat clean. Bulking diet, limit processed foods and sugar, eat daily fruits and vegetables.
  • Drink 2 liters of water daily.
  • Meditate on a best effort basis.

Effectiveness

  • Contain online distractions to outside work hours.
  • Complete 30 work sessions weekly.
  • Pre-plan days and front-load important tasks.
  • Track schedule to diagnose issues.

Business

  • Habit Gym
    • Widen the top of the funnel
      • Create a low-commitment trial to demonstrate value proposition
      • Create a system to promote success stories on social media
    • Improve conversion
      • Evangelize the problem that it solves
      • Add more touchpoints to convert
      • Invest in product experience - personal guidance, curated content, more accessible communication channels
  • Other ventures - validate demand for 3 business ideas

On the writing front, I’m taking a break from publishing weekly. I’ll be doing it on a best-effort basis. Hope to see you soon!

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