18 Months In The Hole 🕳️

the art of buying time

After 18 months of living off savings, I’ve emerged from the hole. The journey from a six-figure income to zero has been filled with lessons, struggles, and realizations. One moment I was slinging $1K into random stocks and the next I found myself staring at a wall of canned beans scrutinizing whether it’s worth it to get organic.

As an only child of immigrants, I grew up with an abundance of food on the table and toys on the floor, and saw the pervasive role of money in our everyday existence. Money, like gravity, was impossible to ignore. It’s why I begged my parents to buy me a 5 pound chocolate bar at Hershey Park (great value). It’s why I worked minimum wage jobs throughout high school.

I grew up expecting to always work. I didn’t know any adults who worked seasonally, and even those who owned businesses worked harder than their employees. Even the phrase “earn a living” assumes that living must be earned. Not working was not normal.

When I first embarked on this amorphous adventure of zero income, I had no destination or even a trailhead to follow. I prepared financially for around a year of wandering, but as time passed, I felt a quiet confidence that I was on the right path, even if it would take longer than anticipated. I found myself naturally cutting costs to extend runway.

Until recently, I was relatively comfortable living off savings despite not knowing when this period of uncertainty would end. Through a combination of practical frugality and emotional resilience, I’ve managed to maintain my lifestyle despite my bank account shrinking month after month.

In an unexpected turn of events, I announced my coaching practice and received a part-time job offer on the same day. Combined, I now have enough income to cover my daily expenses and even start saving again. I’m still making less than before, but I feel far more grounded and focused than I did 18 months ago.

Now that I’m no longer draining my savings, I have more spaciousness and can think long-term again. Interestingly, I didn’t fully realize I was “in the hole” until I emerged out of it. Having returned, I feel called to share my experience, what I learned about money and myself, and also how I came to realize it wasn’t really a hole at all.

Climbing Into The Hole

When I quit my job, I plunged into a fog of uncertainty. With no clear plan beyond the first few months, I adamantly declared to others - and myself - that I'd never return to a conventional job, especially as a full-time product manager.

Looking back, my eagerness to flip ahead to the next chapter made me overly insistent on burying my past and shedding identities that no longer served me. The deeper I went into this process, the more I descended into what I call "the hole.”

I would bump against the walls of reality constantly, reminding me that money still mattered. I couldn't escape its influence at the grocery store, gas station, or while analyzing restaurant menus for a balance of portion and price.

Despite these reminders, I remained stubborn in my commitment to living life on my own terms. Instead of moving back home and subsisting on rice and beans, I chose to ski in Tahoe, surf in Hawaii, and prioritize adventure and learning over financial stability. This decision came with its own set of tradeoffs that I continually grappled with.

For the first time, I found myself in a unique limbo. I was no longer earning money, but had enough savings to last about over a year. The safety net of my former career remained, but I was so averse to returning that I essentially removed it as a possibility. This left me voluntarily separated from income, financially secure for the moment, yet uncompromising about not reverting to my previous path.

Living In The Hole

Once I was in the hole, it was time to settle in and make it feel like home. I knew I could be here for a while.

In my tiny shoebox room in Sunset Park, Brooklyn, I had to get creative. To fit a desk, I unscrewed the right side door of my dresser. My mattress lay directly on the floor, not out of laziness or cheapness, but because I wasn't sure how long I'd stay. The room faced a brightly lit Costco parking lot. We were also right next to the highway, and the entire apartment would shake when an 18-wheeler drove by. I got used to it with earplugs and an eye cover.

Food became another area of adjustment. Without an office to go to or a steady income to spend, I ate out less. I experimented with various oatmeal and smoothie recipes, consuming a massive protein-packed bowl of oatmeal daily for months before switching to smoothies with essentially the same ingredients, just swapping Greek yogurt for oats.

As someone who enjoys weightlifting, getting enough protein was crucial. Costco's rotisserie chicken became my go-to. For $5, I had a pre-cooked meat that would last 4-5 days. I got into a routine of buying one chicken once a week, only pausing for a week at a time before reverting back to this ritual of frugality.

My new reality was marked by visible shifts of frugal living and creative adaptations, but the most significant shifts were happening internally.

Being In The Hole

Do I really want this?

Living off savings became a forcing function for asking “Do I really want this?” When every transaction siphons away potential runway, I evaluated purchases with more scrutiny, but also more intentionality. Every financial choice became an exercise in discovering my desires, and in turn, more of myself.

In Trader Joe’s, I’d find myself evaluating a variety of fruits and snacks, asking what I truly want. For instance, I really do think kombucha is worth $4 every now and then. And even though they don’t have that much protein, GoMacro bars make me feel great. “Splurging” on organic Honeycrisp apples is worth it if they’re sufficiently crisp and sweet.

Every time there was an opportunity to travel or go to a concert, I stood face-to-face with a more authentic version of myself. When money came relatively easily, attending an event would be a “no-brainer”—as in, I didn’t carefully consider if I truly wanted to go. Sometimes I would succumb to friendly peer pressure even though my body was tired or I didn’t feel entirely energized.

I began to understand my version of “worth it”. Plane tickets to visit friends are always worth it. I discovered that being able to host dinner parties with friends brings me a disproportionate amount of joy. So does paying for a nicer gym with ample equipment and bigger dudes to motivate me.

I learned to tune into my emotions and energy levels. I started saying yes to activities only when I actually felt energized and could bring my full self. This realization made me wonder how often I would go out or grab dinner when I was actually exhausted or feeling overwhelmed.

Ultimately, this exercise goes beyond financial transactions. Money was just the vehicle for understanding what I want. I may have been spending less, but I was enjoying more.

Wanting what I have

Without an ever-increasing balance to draw funds from, I mentally blocked out making any big purchases or taking expensive trips. With my sharp right turn off the corporate highway, I veered onto an unmarked dirt road, leaving behind the congested lanes of identical career aspirations.

This new path allowed me to opt out of the comparison game and focus on my self-initiated period of exploration and experimentation. During ski season, several friends made it out to Japan or the Alps, but instead of wishing I was there, I asked myself “How can I enjoy skiing where I am even more?” Over time, the FOMO faded away as I realized that the fear is less about missing out on other people’s activities and more about not doing what we truly want to do.

Self-imposed constraints can be either crippling or liberating, depending on the context. I found that enjoying the one dish right in front of us can be more satisfying than endless options. This reduction of optionality guided me towards simplifying and refining my desires.

Becoming intimate with discomfort

There are two ways to alleviate discomfort. The most common method is to locate the symptom and attempt to fix it, like popping Advil or applying Icy Hot. The other way is go beyond the symptom to the root cause, hold onto it, become familiar with it, and be with it. Simply being aware of where the discomfort is emanating from often reduces it. When faced with financial stress, I’d turn my attention inwards, examining my recent activities and emotional state. This internal audit often revealed that I was trying to do too much or not focusing on the most important thing.

As I became more familiar with my discomforts, they seemed less like problems to be solved and more like contexts to explore and sit with. For example, when considering taking an Uber from the airport, my initial thought could be, "I don't want to spend that much." This led me to question: What does the Uber provide that public transit doesn't? Speed and comfort. Then I would ask, “But am I really in a rush right now? This reflection resulted in a reorientation: "This rush is just a story of urgency and overwhelm from trying to do too much. I’m not actually in a rush. I'm on time." This process of questioning and reframing helped me navigate discomfort more effectively.

How to spend money

There are tons of self-help and personal finance books on how to earn, invest, and save. But spending money is a skill too. One way to hone this skill is to have some amount saved up and then for a temporary period, cut yourself off from any new sources of money.

With the pragmatic desire of keeping my financial runway long and an openness to trying new things, I began collecting evidence that suggested spending more did not always guarantee better outcomes. To avoid spending over $100 on a yoga studio membership, I discovered St. Mark’s yoga, where each class is only $10.

For my girlfriend’s birthday dinner, rather than splurging on omakase, I sourced chutoro (medium fatty tuna) and uni directly from a fish monger that supplies sushi restaurants. Buying premium ingredients and then preparing the nigiri myself led to plenty of pieces for everyone. I also got to learn a new skill and celebrate in a way that felt right given the circumstances.

Returning from a Charlottesville wedding, we opted for a seven-hour Amtrak ride instead of a $400 flight back to NYC. What I feared would be a wasted day became an unexpected highlight. We bumped into four other wedding guests on board. Spacious seats and weak WiFi kept digital distractions at bay, allowing us to gaze out the window, munch on snacks, and enjoy each other’s company. The cozy cafe car transported me back to a nostalgic, slower-paced world.

How you spend money can be perceived as penny pinching or making deliberate tradeoffs depending on your mindset. Scarfing down rotisserie chicken for weeks can be an unusual punishment or practical choice. Taking public transit could feel like slow torture chore or a smart way to save. Running outside might seem like a broke person's workout or a chance to connect with your surroundings. A simple park stroll could be seen as wasted time to #getshitdone or the very reason to work hard.

How we spend money isn't just about dollars and cents. It's rooted in a foundational understanding of ourselves - our values, our deepest desires, and our ability to find joy in any moment. In our capitalist, globalized society, you can buy a lot that will bring you some happiness, but no amount of money is going to teach you how to savor the present moment or truly know yourself.

I was okay with being frugal because it served something beyond my hedonistic desires. It was a devotion towards learning more about myself and continuing to progress, despite not having a financial yardstick to measure with.

When The Hole Starts Caving In

It wasn’t all sunshine and rainbows. At times, not having any income brought feelings of overwhelm, scarcity, and hopelessness. No matter how fun or productive an individual day was, there was always a looming storm cloud reminding me that my current way of living was only temporary. The feeling of enjoying something new, but knowing it may someday disappear was deeply unsettling. I never felt true certainty that things would work out.

Intellectually, I knew I could return to working full-time in tech, but I had a visceral reaction to this idea. Turning back felt like lying to myself by not fully expressing my skills and interests outside product management. It would also betray my future self, the one that would recognize being in the hole as an essential chapter in my journey. Exiting the hole just to go back to how it used to be, felt like a regression, bringing along with it old patterns, stories, and core beliefs that no longer serve me. I truly believed that climbing out of the hole prematurely would be setting myself up for failure. Even though I knew getting a full-time job again would erase my insecurities around money, I felt allergic and even disgusted by the thought. It was like being a FearFactor participant staring at a plate of spiders.

Underneath My Relationship With Money

My relationship with money ebbed and flowed based on my actions and emotions. I anticipated feeling good or bad depending on if I had income or how the stock market was doing.

On the last day of every month, I update my net worth and conduct a monthly reflection. I review the past month and set intentions for the next month. I noticed that my sense of wellbeing, energy, and happiness had little correlation with my finances. Instead, it correlated with things in my control.

My worst months were when I was injured, overwhelmed, and crippled by resistance. Last October, I was in peak marathon training mode and afterwards, I traveled to DC, Colorado, and Costa Rica. I was overwhelmed. The past two Februaries have been rough because I injured my left rotator cuff and broke my right ankle. Not being able to walk, run, or ski for weeks led to helplessness, lethargy, and frustration. Worries about money also popped up when I was avoiding emotions that had not been processed or work that needed to be done.

My best months were when I was healthy, setting reasonable expectations, and taking consistent, intentional action on my most important projects. On days when I slept enough, worked out, ate well, made progress, created something, and had breaks throughout the day, I didn’t think about money. I was well-rested, focused, and present, so my attention towards money remained minimal.

Now that I know my feelings about money aren’t tied to my actual finances, I’m able to apply these learnings as guideposts. If I catch myself worrying about money, I ask myself “What am I avoiding right now?” or “Have I been taking care of myself recently?” Then I ask “What actions can I take right now?” These inquiries have a wide-ranging effect, from realizing I haven’t taken a break all day to I’ve been putting off important tasks. Instead of staying in the doom loop and ruminating about money, I peel back the layers and get to the root. Often, it’s simpler and more actionable than I thought, like saying no to obligations or taking a long, restful break away from screens.

The Art of Buying Time

Living without income for 18 months taught me lessons that can only be learned from dwelling in the deep discomfort watching your bank account dwindle. It challenged me to live fully and think creatively, without income or compromising my values.

Key Experiences:

• Hosting a Bring Your Favorite Neighborhood Cheap Eats (BYFNCE) dinner party, where we feasted on dumplings, pasta, sandwiches, cheesecake, and more.

• Finding affordable Airbnbs like a co-living house in Costa Rica with an ocean view and ski leases that allow me to live near the mountains in winter.

• Meticulously cutting the white part of watermelon to stir fry like zucchini. I knew it was something my parents ate growing up in rural China, back when meat was only eaten during Chinese New Years and even one egg was considered a luxury.

• Surfing in rural Indonesia taught me that all you need for an adventure is a moped, a surfboard, and a willingness to ride unpaved dirt roads.

• A free private tour of Singapore’s major museums reminded me it’s not always about money, but the relationships.

New Money Beliefs:

• You don’t always have to be spending money. One month I spent $5,000 which included a future Airbnb and my ski pass. But a month later, I spent only a couple hundred bucks as it was the holidays and I was back home. No meaningful difference in happiness was detected.

• Not having income has a side effect of distancing yourself from the tendrils of our capitalist attention economy. Billboards, brand deals, and ads used to control my attention back when I had the money to potentially purchase Fabletics shorts (Instagram), B2B SaaS (SF highways lol), or prescription drugs (WTF America?). By not actually having a bunch of free-flowing cash to buy unnecessary things dangling in front of my face, I found it much easier to ignore the inanimate voices shouting “BUY ME!”

• I learned you can increase enjoyment by doing less, which is a great alternative to having more fun by spending more money. By creating more spaciousness in my schedule and mind, and not always being in a rush anymore, I could drop into deeper presence and enjoy more of whatever I was doing.

• “Who are you without work or money?” I have something in mind now, but it’s living response, constantly evolving as I learn more about myself. Given we are humans with practical needs living in a material world, I see this an ongoing question to be with and live with, rather than one with a fixed answer.

The Whispers From Outside

Slowly, but surely, I started to notice moments when I would bump against the edges of being in the hole. Right before, we hit record for a podcast, Paul and Steve said they could hear a loud noise coming from my mic. It was my old laptop’s fan, whizzing away as it desperately tried to cool things down. I had to switch to Airpods and accept that my voice would be recorded in lower quality. After a few more months of loading animations and loud hums, Steve generously gifted me a new Macbook Air. Once I began using my new computer, I was reminded that up-to-date, efficient equipment is always worth the cost.

I noticed I was thinking about money more than I’d like to. At the grocery store, I’d hesitate to pick a type of apple or choose free-range, organic, or both free-range and organic eggs. This felt like an intrusion of my inner landscape. I was just trying to grab groceries, not reflect deeply about my finances.

Around the same time, I had dinner at Sukh, a new Thai restaurant in Brooklyn. We opted for family style and shared the whole marinated squid, a papaya salad that stayed authentically Thai-spicy, and new dishes like khao hor bai bua and khao tom haeng. Every plate was left bare and as we walked out, I found myself wanting to experience more of NYC’s food scene. But this competing voice chimed in, reminding me that it was okay to eat out sometimes, but not that often at places that charge $28 an entrée. All I knew was at the time, I was okay with a $13 Cava bowl, but spending $50 on dinner, no matter how delicious, felt overindulgent and unsustainable. Just a year prior, I was happy to camp in my car and eat bowl after bowl of oatmeal. Now I was shifting towards wanting more comfort and financial freedom.

Quarterlife, confirmed that my chapter of finding meaning was closing and a new one of re-discovering stability was beginning. As I read, I realized I'm fundamentally a Stability Type, yet I'd been living like a Meaning Type. Through following the clients' journeys of finding meaning or creating stability, I recognized it was time to return to swing the pendulum back to equilibrium. Viewing my experience as a dynamic wobble or perpetual oscillation helped me focus on making money again without dismissing my new understandings or being too hard on myself.

As I immersed myself in coaching, I started to see progress. I was improving at a noticeable rate, and more importantly, I was enjoying it. The more confident I felt in coaching, the more I was able to lift my head up and view the long-term horizon. I realized the important role that money would play in my coaching evolution.

After I said, “It feels like I’m planting lots of seeds, but don’t know which will sprout.” my coach Sasha guided me through a visualization where I saw myself watering a big plant pulsating with energy. As I watered the plant, with my time, energy, and attention, it sent electricity into the seedlings, many still below the soil. Coming out of the visualization, I sat with the possibility that making money again could help nurture the other seeds.

Emerging Out of The Cave

It’s been exactly one month since I walked out of the cave. You see, I’ve been describing these past 18 months as being in a hole, but once I was out, I looked back and realized I had been in a cave the entire time. Although the hole and the cave share similar qualities of darkness, quietness, isolation, and opportunity to explore, instead of falling or being pushed in, I entered this cave voluntarily. And just as I walked in, I could choose to leave at any time.

The completion of my no income journey felt as simple as walking out of a cave. A month ago, on the same day that I announced my coaching practice, I received an offer to join a small startup to lead product growth. I heard about the opportunity from my former manager as we sat on a bench at his kids’ elementary school. At the time, I wasn’t even sure if making money again was the right call. I had bookmarked a few other job postings, but even the act of doing so felt off.

However, the whole process felt natural and authentic. I never had to submit a resumé, spin up a narrative for the past 18 months of “not working”, or fabricate a story about my passion for B2B SaaS APIs. I was transparent about my coaching and writing. And when I received the verbal offer, I didn’t negotiate because the pay was fair, and I started two days later.

I made it clear that I wanted to work part-time and on my own schedule. The jury is still out on how this next chapter will go. I’m viewing this as one grand experiment. My intention is to treat this job as just a job, which still means performing at a high level and enjoying the work.

Now, I view money as a resource to be used in service of actualizing my truest desires and to think on a longer time horizon. I’ve been exploring training programs across a variety of modalities to deepen my coaching practice. I also have several slow hunches around identity, ambition, and self-discovery that may become a core part of my practice. But for now, they’re just seeds, waiting to be tended to and nurtured.

In many ways this is a full circle moment—a mini hero’s journey if you will. I left the ordinary corporate world, wandered around the otherworld, and have now returned. This odyssey has refined my vision, integrating my vocation as a coach and writer with the practical realities of the material world we live in. I return not just with newfound purpose, but also a restored appreciation for money and my past self. My journey has equipped me to navigate both the depths of meaningful work and the currents of financial stability, emerging as a more whole human ready to embrace and nurture this integrated path.

As excited as I am to no longer be living off savings, I’m also open to the idea that this may not be the last time I enter the cave. Being in the cave served me well for what I needed. So the next time that I’m at the mouth of the cave and it beckons, maybe I’ll step in with acceptance, settle into its familiar embrace, and take a seat.