Back After A Long Break

The last part of funemployment

Jul 14, 2025

Thinking about my new job the week before starting (no, not really)

I recently finished the first three months at a new job after wrapping up my year-long career break.

I’ve shared my initial thoughts on my funemployment along with my travels during that time; this post will cover my transition back to the working world.

Diamonds Are Forged Under Pressure

Coming back from an amazing trip across Asia over the holidays, I knew that I had to lock back in on the job search. It was late January and I anticipated hiring to slow down by Memorial Day weekend as people began taking time off during the summer. I had four months to land a job.

Fortunately, two events happened to keep me focused on my job hunt.

First, a friend reached out to me asking if I was interested in consulting for his startup. I initially hesitated out of concern that it would take away from my time looking for new roles, but managed by agreeing on a weekly maximum number of hours I would spend in this role. This consulting engagement forced me to be productive because I was now getting paid to do something and I had to deliver. I would no longer be derailed by my “off” days because deadlines wait for nobody.

Next, another friend asked me if I could help keep him accountable in his job search. After speaking, I decided to join him in forming an accountability group. We would meet once a week to review our progress over the week and set goals for the following week. I found these sessions to be immensely helpful because my friend would dig deep - challenging me on why I would miss my goals. His questioning helped me uncover the underlying reasons and we discussed ways to address them. We would even set penalties like a $20 payment to the other person if we didn’t achieve a goal we set.

At this point, I felt like I had a job again even if I wasn’t working full-time. I had weekly goals and concrete deliverables, plus a schedule set roughly around general working hours (9am to 5pm).

When I first left my job, I had absolute time freedom. I made a long list of things I wanted to do and places to go. I tried many things at once and failed to make any meaningful progress. There were days I would wake up planning on doing something, procrastinate, feel bad, and then wallow in my sorrow by procrastinating even more. Sometimes it would take days for me to be stuck in this rut before the pain from being in the situation outweighed the effort required to accomplish a task, driving me to finish it.

I found the solution in concrete deadlines.

Sure, a last-minute rush request leading to a 12+ hour work day is no fun, but it does get one going.

In the end, the best way to set targets is to make them realistic and make consistent progress towards them over time.

This is something I will work on and maybe even find accountability partners for my new projects now that I’m back to working full-time.

Not Like The First Day Back At School

After a few weeks and through a mix of hustle, consistency, and luck, I got a job offer.

I booked a trip the day after signing my offer as a “last hurrah” and enjoyed two weeks in the land of smiles. My only goals were to: 1) enjoy myself as much as possible, and 2) not have too much fun so that I can actually work when I start.

I made it back in one piece and slept surprisingly well the night before my first day.

Back in school, I always had trouble sleeping on the last night of summer break. I mourned my last day of “freedom” and dreaded the following day going back into a routine.

More recently, I also felt nervous with excitement the night before starting my first full-time job. The next day was a pivotal day - the start of decades as a working professional.

This time, things were different. It was not my first rodeo.

Unlike my school days, I was not mourning something lost. I was ready for something new and ready to get back into a routine.

The Wild Ride Continues

Since starting this job, I’ve been on six business trips, worked multiple 12+ hour days, and learned a ton in a new skill that I see will benefit me for my entire career.

I still have a long way to go (and some targets to hit), so I need to diligently get there day by day.

Just like my past two jobs, I’m back in the fire now. This time, I’m armed with a new perspective from my time off.

Thanks for reading! I know how hard it can be to be in-between jobs - reach out if you want someone to chat with.

A Journey Five Years In The Making

Reflections from visiting Shanghai, Taipei, Bangkok, and HCM City

Leo Lu

Mar 04, 2025

I once bought a one-way ticket to Shanghai in the summer of 2020. I was young, had seen enough of the corporate world, and was ready for a new adventure.

Clearly, things didn’t turn out the way I expected because of the pandemic.

Nor did I expect to have left my job in the middle of 2024 and then end up traveling around Asia.

I spent the fall of 2024 mostly focused on the job search; however, given the holidays were coming up, I decided to take a break.

It had been five years since I visited Asia, so I decided to spend an extended period of time there. I knew I wanted to visit my grandparents first, so I started in Shanghai and leveraged the 144-hour transit rule (now extended to ten days) to visit the country without a visa. I then spent a week in Taipei after Shanghai because I’d never been there before and could also visit some relatives. I was also interested in living in Bangkok for an extended period of time because I was drawn by all of the YouTube videos about living there and heard great things from friends, so I booked an Airbnb there for a month (the general minimum-length since the platform isn’t technically legal in the country). Lastly, I spent a week in Ho Chi Minh City to explore a new city and meet up with some friends who were already going to be there.

Shanghai

Although a few years had passed since I visited Shanghai, I felt a sense of nostalgia upon landing in the city - it felt like seeing an old friend. Yet I was surprised by how things changed.

I made my way to my grandparents’ apartment by navigating the metro system by memory only to notice a significant change in my surroundings. What used to be a few shacks transformed into an exotic car dealership. Old warehouses were turning into coffee shops and co-working spaces reminiscent of the evolution of Williamsburg, Brooklyn. Electric cars were everywhere.

Just as how the surroundings had changed, I also felt the vibe of Shanghai change to become more inward-looking. I noticed how there weren’t as many foreigners as there used to be given many had left after the pandemic. How the country had its own payments ecosystem consisting mostly of WeChat Pay and AliPay to purchase goods and services. There was a China-specific application for everything from social media to e-commerce to maps - it was quite an adjustment to pick everything up almost from scratch.

I noticed that the average young person in Shanghai, a global city, spoke English fairly poorly compared to people in Taipei and Bangkok. It’s one thing to know a language at a textbook level and a whole other to use it practically, and it goes to show how Chinese people are now more focused on their own language and country vs. the rest of the world. China is definitely growing its influence in Southeast Asia, Latin America, and Africa, and it shows (more on this later).

Taipei

I came to Taipei with no expectations and the city completely blew me away. I loved this city.

I couldn’t help but feel like I was in a Japanese city with the city’s architecture, cleanliness, general politeness of the people, convenience stores, and design. Even the bidets.

Overall, I would describe Taipei as a comfortable place to live. Crossing the street doesn’t require a battle with motorbikes like in Shanghai and Ho Chi Minh. The traffic is nothing compared to Bangkok. There’s great food. There aren’t too many distractions unlike Bangkok, where nightlife happens seven days of the week. There’s no need to use a VPN to access many internet services like in China.

I can see why so many Asians from the West have decided to live in Taipei and I hope the city develops further.

Bangkok

Bangkok to me is THE megacity. Although I’ve lived in New York City, São Paulo (South America’s largest city), and Shanghai, I thought Bangkok eclipsed them all when it came to the energy of the city, size, amount of things to do, traffic, and visitors from every country.

They say that NYC is the city that never sleeps, but I’d be hard pressed to find traffic at 5am in the morning with all the people coming home from the clubs. I thought the traffic in Mexico City was bad, but Bangkok is a whole other story. Being the most visited city in the ENTIRE world, Bangkok is super international. I was also in awe of the malls in this city. I had seen nice malls in Asia in Hong Kong, Shanghai, and Taipei, but the number of nice malls in Bangkok is truly amazing. Each one can be a mini-village.

There’s a reason why so many people are now moving to Bangkok - the lifestyle is unmatched. Picture having your own place in a luxury apartment near the center of the city for under $1k a month, complete with a pool and gym. Add on being able to order takeout all the time and eat out while still spending less than the cost of groceries in the USA. Most car rides on Grab, the equivalent of Uber, come out to around $5. Plus, no homeless people nor crazy people. You only have to be careful of motorbikes.

Of course, there are two sides to the coin. You are still in a foreign country. Although many Thais speak English, you are still in a country with a different language and culture. You will have to find a way to make an income in spite of the massive distance and time zone difference, which can make it feel like you are in a completely different world. I was also cognizant of my privilege in being able to spend USD in the country, a luxury the locals do not have.

Ho Chi Minh city

If Bangkok was a megacity, visiting Ho Chi Minh city was like exploring a new frontier. Given the city is still developing, it felt like how Shanghai was during my childhood, with lots of motorbikes, much fewer skyscrapers, and many more small buildings. In contrast to the many malls in Bangkok, HCM only had two main malls. There were nowhere near as many foreigners living in the city, and there were many more backpacker-type tourists than the digital nomads in Bangkok.

Although I say HCM is still developing, the city still has everything you need from a modern city, with plenty of restaurants, stores, bars and clubs, and other points of interest. I can see the city becoming a megacity in the coming decades.

Final thoughts from my journey to the East

After traveling through East Asia and Southeast Asia, I’ve come to further embrace my identity as a Chinese American.

Having grown up as a minority, it felt like a breath of fresh air to be amongst people who looked like me. Instead of feeling like a background character in the West nor sticking out like a sore thumb in regions like Latin America, I was just an ordinary person in Asia, especially in East Asian, Mandarin-speaking cities like Shanghai and Taipei.

On that note, I’ve found my Mandarin to come in clutch several times in places I did not expect. Naturally, I spoke Mandarin in Shanghai and Taipei to communicate with my grandparents and for everyday interactions. Surprisingly, I was also able to communicate better with several Thais and Vietnamese in Mandarin than in English.

What started with a one-way ticket to Shanghai became an unforgettable trip at a very unique point in my life. I will fondly remember the memories I made visiting relatives, catching up with friends, making new friends, and going on new experiences.

Thanks for reading! For those interesting in joining a community of Asian diaspora in the West who are interested in living in Asia, check out a community I’m part of called Journey To The East.

Leo's Letter // Entering A New Era

Not the typical "turning 30" post

Leo Lu

Nov 29, 2024

Hey, it’s great to have you.

I’m back after a period of highs and lows during my ongoing exploratory phase.

What I’ve Been Up To

I started my funemployment with optimism, excited that I could finally have the time to try everything on my bucket list. Wouldn’t it be great to travel, do some consulting work, experiment with business ideas, and look for jobs with all this newfound free time?

Turns out it’s not that simple. I spent some days doing too much and wearing myself out. I then had to spend a few days doing very little to unwind. Every time I fell off, it took as much force as rolling a boulder up a hill to get back on track. Sometimes I would plan for a few days filled with activities, fail to start, fall behind, and feel bad about it. My excuse was that I would start the next day, but that time would come and I still wouldn’t do anything and feel even worse. The cycle would repeat for a few days until I changed my environment and got back on track.

It’s ironic that I was oftentimes more stressed in this period of self-imposed deadlines than I was with external ones.

Things improved when I decided to focus on only one thing at a time. I spent most of the past few weeks focusing on the job search and established a routine where I would spend the mornings focusing in this area so I felt that I had spent at least part of my day in a productive manner. I joined a peer-led job search council and have been following the steps outlined in the book “Never Search Alone” to determine which roles and industries I wanted to focus on and how to position myself. I built momentum by reaching out to friends, former colleagues, and other acquaintances - many who have been helpful in my journey and made me feel that I was not alone in this search.

While I’m still in the process of landing a new role, I feel invigorated by the support I’ve received and my confidence rises the deeper I go in my explorations in the roles I’m targeting.

Lessons From Turning 30

Now onto the heart of this post: I recently turned 30 and felt that it would be good to share some observations as someone living in the NYC area and has noticed some significant changes from my early and mid-20’s.

People move on

Large cities are transient and people move, both literally and physically.

People move out of the city for various reasons: for work, to be closer to their families, or for more peace and quiet (even me, having moved from Manhattan to Jersey City).

Even when you and your friends are in the same city, you might not be in the same life stage. You may be single and your friend group may be mostly couples. Some couples might even have kids (a perfect valid reason for why you haven’t seen a friend in a while).

Lastly, people’s interests change. What might have been fun a while back may not be fun anymore, and it’s ok. There was a time and place for that.

All of this is natural progression of growing up.

Identity without labels

I remember my senior year of college where all of the students would ask each other what they would be doing after graduation. I had felt a sense of FOMO because I wasn’t going to be working in a prestigious job like investment banking or consulting.

On the other hand, I remember the time I was working in venture capital and the frequent inquiries I would get from founders wanting to pitch their startup, vendors wanting to work with the portfolio companies, and other requests. I felt like I had in a sense “made it”.

Now that I don’t have a full-time job, it took me a while to adjust. I felt some hesitation going to networking events because I didn’t have my job title.

Eventually, I got over this by focusing on what I could bring to the table over my label. I approached events with curiosity, without any expectations for networking and this helped me ease into going to events. I’m even hosting my own event in early December and I know those who are going know me for who I am versus what I appear to be.

Everyone has their own pace

I’ve been both “ahead” and “behind” in my career. But the only point of comparison should be oneself.

In fact, the further out you go from school, where everyone starts off, the more variables come into play. Some people got to where they were by being at the right place at the right time. Others chose the wrong company, or an industry that was too early for its time. Personal events happen. All this to say that there’s a lot that can’t be controlled, you never know the specifics of one person’s journey.

I can only measure my progress one day at a time. Did I do what I set out to do? Did I challenge myself? If so, then I did well. For example, I had to re-learn SQL for a job interview, and even though I didn’t get the job, I passed the SQL test and for that I feel accomplished.

The War of Art covers the concept of “Resistance”, the force that holds you back and must be overcome on a daily basis. Resistance is the only one to beat.

Always produce

I’m still figuring things out right now but I’m writing as a way to help me do so. This post was largely motivated by catch-ups with a few friends who mentioned writing, so thank you to those who encouraged me.

Paul Graham, founder of YCombinator, once said “Always produce will discover your life's work the way water, with the aid of gravity, finds the hole in your roof.”

Here’s to consistently overcoming resistance to produce and figure things out along the way.

P.S. - I’m making more efforts to keep in touch with friends old and new. I’ll be hosting a holiday party at my apartment in Jersey City on Saturday, December 7. If you’d like to come, send me a message (open invite)!

Leo's Letter // Farewell Mental Atrophy

Doing what I want to, not what I have to

Leo Lu

Jul 03, 2024

Hey, it’s great to have you.

There’s a viral video going around of a guy wearing the most comfy sweatshirt and sweatpants bouncing on his bed playing with his DJ set.

The caption goes: “bro got laid off 2 months ago and now he does this every day”.

He MUST be living the life. Right?

Not so fast. Sitting at home all day is nice and all for the him, but he still has to worry about everyday things - what will be the next meal? When will the laundry need to be done? More importantly, thanks to social media, how will he feel when he sees his friends getting married, promoted at their jobs, or taking trips? Speak not of all of the terrible news happening that make it feel as if the world is ending.

Ok, this guy is not just the guy in the video, but also one of us. In fact, it was me for a while.

Funemployment is going

I started the month of May doing great. As I wrote in my last newsletter, I was back on my routine and balancing a mix of professional development with fun, doing things I would never be able to do otherwise like go to a museum any day of the week. I caught up with friends, got into swimming laps at the pool and going to the sauna, and started reading a physical book.

This was a dream mixed with reality. I still felt stressors such as grocery shopping, cooking, laundry, planning out my day, and other errands (retired people, I can see how you keep busy).

I’m not saying this to complain about everyday chores, but to make the point that everything is relative. When one stressor is removed, another replaces it. The mind is never satisfied. To take this to the extreme, there was a point that I fell off track and felt a sense of foreboding at the need to do anything besides sit in front of my computer screen and watch YouTube videos - a far cry from the days I was spending my mornings working on personal projects and afternoons socializing. This was an even further departure from when I was working 60+ hour weeks and handling last-minute fire drills.

Your comfort zone is like a muscle. It shrinks and expands.

The less I was handling, the less I could handle. The more life threw at me, the more I could handle up to a certain amount. It’s about finding the right balance without being too comfortable.

Every day is a Sunday afternoon

I eventually dug myself out of this rut and took a break from my YouTube videos to write this (just kidding).

I really meant that I didn’t need to stop my relaxing but I wanted to. I wanted to use this limited window of opportunity to work on my own projects vs. those of an employer, a time to tackle the important but not urgent tasks instead of taking a nap. Like a Sunday afternoon.

I found two tactics to be most helpful: putting myself in new environments and maximizing my most productive hours.

A change in environment can do wonders in breaking up a monotonous routine. Going somewhere new to work makes work feel like an adventure. It also helps prevent temptations such as that comfy bed in your bedroom that is right next to your desk (thanks small NYC apartments). When blessed with the freedom of not having to go to an office, why not take advantage of it?

In terms of productive hours, I know that I’m the most creative and energetic in the mornings, especially before eating anything. This is why I get to work immediately after getting ready in the morning and wait to eat breakfast (if I even eat it at all). I make sure to leverage my peak period for tasks requiring the most amount of focus and creativity, leaving meetings to the afternoon. This may apply more to Sunday mornings instead of afternoons, but you get my point.

The Journey Continues

I’m still in my exploratory phase and gradually checking off things on my bucket list.

It’s been an immensely rewarding experience so far in experiencing different lifestyles and cultures while still experimenting with various professional opportunities - spending my mornings cracking away at things and my afternoons exploring.

Specifically, I’ve updated my personal site, gotten back into content creation with posts on professional development, and thought about what I want to do next. More to come.

Think of this lifestyle like trying to keep fit while traveling. It’s necessary to stay sharp unless you want to start from square one when you get back.

Leo's Letter #45 // Quarter Life Crisis Club

Plans never go as expected, it's part of life

Leo Lu

May 21, 2024

Hey, it’s great to have you. And welcome new readers!

I’m back

After sprinting for the past year without much of a break, I’m back.

Last month, I left my job at a crypto venture capital firm and am currently pausing to really reflect and figure out what to do next.

This will be the longest break I’ve had since graduating college and starting work full-time in 2016. For once, I don’t know what’s next - no SAT score to hit to get into college, summer internship to secure to get that full-time offer, or GMAT to get into an MBA program. It’ll be time for myself that I may not have once I start working full-time again, an opportunity to cross things off of my bucket list. It’s also a time of uncertainty given the state of the economy, especially in tech.

Do I take a risk and start something of my own? Or do I take a role that’s more sustainable than my most recent roles within tech? What will I do in these coming months? These are the questions I ask myself as a new member of the quarter life crisis club.

Two versions of “retirement”

The biggest thing I looked forward to after starting my funemployment was not having to wake up to an alarm. I could sleep in every day. Stay up late without worrying about having to get up early the next day. No early meetings nor deliverables to hit. Nobody to report to. I could do whatever I wanted to, whenever I wanted.

And that’s what I did. I was a couch potato for the first week, signing into Netflix for the first time in recent memory and binging on shows. Staying up past midnight every night scrolling on my phone and waking up past noon. Not going outside for two straight days and living without commitments.

But then it got old. One day, I looked into the mirror and saw a version of myself who freeloaded by living in his parents basement. I was gaining weight from eating junk food, growing a five o’clock shadow by not shaving, and living in Gundam land (the anime series I was watching). I began to feel a resistance, as if I was procrastinating to avoid facing something: what I would do with my newfound freedom and uncertainty.

This couldn’t be it. There must be more.

I began getting sick of this way of living and gradually started climbing out of this pit. I set myself a schedule that gave me time to make progress towards my career, self development, and still have fun. I created a bucket list of things I wanted to do and set goals with concrete deliverables.

Eventually, I got myself back on track with this new routine. I stopped taking naps in the afternoon and avoided using electronics before bed so that I could fall asleep at a reasonable hour. I made myself sit in front of the computer in the mornings, my most productive hours, and began chipping away at my goals. I scheduled in time for fun to finally check out the places I wanted to go (there’s little competition for a 3pm weekday reservation).

Now, even though I don’t have to wake up to an alarm and can do anything, I get up with a sense of direction and excitement to work on my projects on my terms. I’m trying to enjoy the process.

Takeaways on carving my own path

The first thing I did after starting on my own was to relax. I had been so accustomed to being on “go” mode that it was hard for me to stop. Looking back, I’m pretty sure my sleeping in past noon was due to my body’s need to rest. I needed some uninterrupted downtime to unwind. My restlessness after the week of rest may have been my sign that I was ready to get back into action.

The second piece in charting my own path was to set goals that included input-oriented deliverables. Rather than being outcome-focused, such as targeting landing a specific job, I focused on completing actions that would lead to the goal. In this case, it would be to reach out to a few specific people to get their take on my job targets in order to get advice and referrals. By measuring my success via my inputs, or work I put in, I’m able to get the ball rolling and take action while celebrating small wins vs. sit in fear of facing a humongous goal.

The last action I took was significantly reducing my consumption of social media to avoid the trap of self-comparison. After scrolling through LinkedIn and seeing where my peers were and also doomscrolling the MBA and Layoffs subreddits on Reddit, I began to question myself. I started developing tunnel-vision and it was only after stepping out of this limited viewpoint that I able to start measuring myself by the most important benchmark: myself.

Oh, the places you’ll go!

My journey has just started. In fact, I haven’t cracked the code on how to spend a perfect day, nor do I believe there has to be such a thing. There will be ups and downs. Things won’t go as expected. I’ll adapt as I go.

The most important thing is to stay in the game and avoid overdoing it and burning out.

More to come on where this takes me. I’m taking you all along for the ride.

P.S. - I’m exploring creating a small group for those who are also in a transitionary period (or simply working on side projects) to provide support and accountability. If this is you or you know someone, get in touch!

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