Choose Your Hard
6 questions to ask yourself for a more fulfilling career.
👋 Friends,
My biggest flaw is that I always forget to take time off. Prior to last week, the last proper “vacation” I took was during the winter of 2019. It’s been four years!
The impact: I get tunnel vision - my work suffers, my energy levels are shot, my creativity is stifled, and I’m much less fun to be around. So last week I decided to go to Greece with my girlfriend and go on Do Not Disturb mode.
The result? I feel like an entirely new person.
This is your reminder to take time off for yourself. It makes a massive difference - especially for the busy folks out there who are consistently putting in 50+ hours a week. Take care of yourself.
I’m back in NYC now and summer is in full swing (with temperatures hitting 89°F!). To help you make the most of summer I shared a list of my favorite bars and lounges here. Somehow, this list went viral with 1M views and 7,800+ bookmarks…
I’m currently working on a few events - expect the standard rooftop parties and dinners in the coming weeks, but also concert nights, co-working sessions, bingo night, and retreats out of town.
Btw, if you’re looking to meet other entrepreneurs, founders, and ambitious creator/builder-type folks, you might want to join us at the event I’m hosting called The OOO Summit. It stands for Owners, Operators, and Outliers - referring to business owners, tech and business professionals, and extraordinary people.
IF you are interested, you can bypass the 400-person waitlist and use the discount code “NYSUMMER” for $30 off a ticket here. It expires in TWO days and prices go up then (July 12!).
Stay cool.
I’ve met a shocking amount of millionaires who are unsatisfied with their lives.
These are the folks who make upwards of US$300,000 a year, work less than 40 hours a week, and have healthy social and romantic relationships - yet are still unfulfilled.
On paper, their lives may seem picture-perfect, but take a peek behind the curtains and you’ll find boredom, discontent, and a yearning for more.
The stats seem to support this. A recent Gallup poll reveals that less than half of Americans report being "very satisfied" with their personal lives, and a simple Google search will yield hundreds of results, not dissimilar to the one below:
Choose Your Hard
After speaking with a bunch of individuals in the category of “picture-perfect, but unfulfilled tech professionals” it’s clear that they lack two things.
(1) They are not operating within their Zone of Genius.
The Zone is the intersection where your strengths, your passions, and the market demand for your talents converge.
Example:
Tyler is an excellent interior designer. He loves spending his time browsing through Scandinavian design literature, creating mockups on AutoCAD, and helping people bring their dream home to life. The design firm that employs him also values him a great deal and compensates him well. Tyler is operating well within his Zone.
It’s hard to not be fulfilled when you spend a third or more of your time being generously compensated for doing what you love.
But… there’s another factor:
(2) They haven’t made peace with their Hard.
The Hard is the undesirable, the arduous, and the unsexy things that come with the job.
These are the tradeoffs and drawbacks that one needs to consider before making the important decision to pursue the field.
Examples:
Joey is a FAANG engineer who wants to build something of his own, yet doesn’t want to give up the cushy, big tech life of free lunches and paid time off.
Sharon is an investment banker who is tired of the 80-hour work weeks, yet doesn’t want to take a pay cut.
Alex is a TikTok creator who wants to monetize her audience and go full-time, yet doesn’t want to learn the aspects of business-building required to make her successful.
For Joey, making peace means understanding that he may have to go a year or longer without taking 1:00 pm Matcha breaks.
For Sharon, it might mean taking a 40% pay cut in exchange for 40 hours back every week.
For Alex, it could mean spending upwards of 6 months learning accounting, finance, and operations to ramp up a new business venture.
You can’t just sign up for the benefits without the drawbacks, and the presence of unfulfillment appears when there is a noticeable gap between your expectations and reality.
The happiest, most fulfilled people I know have all chosen their hard. They understand the terms of the game they’re in and will happily play it.
When I was contemplating my decision to leave Google to try my hand at entrepreneurship, I proactively weighed the Good vs the Hard.
The Good:
Full autonomy over my schedule and ability to spend my time how I want, where I want, etc
Complete creative freedom and decision-making power over my work
Unlimited potential for growth, learning, and compensation
The Hard:
My life and headspace would be consumed by my work likely causing me to change/evolve significantly as an individual
Full responsibility for putting food on the table, paying for basic needs like rent and healthcare, and on top of that, sponsoring my visa to be able to stay in America
Losing credibility and the mark of approval for working for a “Google” or “Meta”
I understood that this was my reality for the next 3 years (the time I’ve allocated myself to try out this “entrepreneurship” things), and came to terms with it.
Now, whenever I have a tough moment, I just remind myself that it’s part of the game I signed up to play.
I chose my hard.
"When you choose the benefits of an action, you also choose the drawbacks.
If you want to be an author, you can't only choose the finished novel and book signings. You are also choosing months of lonely typing. If you want to be a bodybuilder, you can't only choose the fit body and attention. You are also choosing the boring meals and calorie counting.
You have to want the lifestyle, not just the outcomes. Otherwise, it doesn't make any sense being jealous. The results of success are usually public and highly visible, but the process behind success is often private and hidden from view. It's easy to want the public rewards, but also have to want the hidden costs."
— James Clear
Self-Reflection Prompts
The following questions will give you a sense of clarity on what you truly value.
Spend an hour answering them. Spend another hour sharing them with a friend or loved one, and a final hour creating an action plan that can move you closer toward your goals
(My answers are quoted below each question for reference on how to answer them)
What are you willing to endure?
Are you prepared to dedicate 80 hours a week to making your mark on the world, or do you prioritize spending time with your family and loved ones? Can you handle volatility, or do you prefer something stable and secure?
These attributes determine how you allocate your time, what you do, and who you spend it with.
e.g. When I took the leap, I was ready to invest more time into my career (30 → 80 hours a week), felt comfortable relying on myself financially rather than an employer, and didn’t mind losing the prestige of working for a well-known company like Google. It was worth the risk for the opportunity of a big payoff.
What makes you forget to eat?
List the stuff here that makes you forget to eat, sleep, and puts you in flow.
It might involve spending doing practicing a functional skill (e.g. writing, drawing), a subject area (e.g. music, space tech), or a type of environment (e.g. the outdoors)
e.g. I thrive on designing experiences that entertain and bring people together. At the moment, this means hosting events, but someday, it might include creating festivals, restaurants, and theme parks. I also enjoy writing and sharing what I’ve learned with others.
If you had to leave the house every day, where would you go and what would you do?
This question is pretty straightforward and reveals how you like to spend your time.
Do you like to create (e.g. write, draw, make) or consume (e.g. read, watch, listen)?
What kinds of physical locations do you gravitate toward?
Do you like to spend it with people or spend it alone?
e.g. I’d spend most of my time creating experiences like events, festivals, and music shows to bring people together. I get a lot of energy from meeting extraordinary people and learning from them.
What would you do if money was not an issue?
Imagine you had $10M, $100M, or even $1B. You do not have to think about generating income ever again.
How do you spend your time? What types of swings will you take? What are the most energizing things you’d want to do?
e.g. Create a massive festival centered around tech, culture, and art. Throw a massive multi-day event on a cruise ship. Build a small town.
I’d spend my time creating memorable and life-changing experiences for others.
What would make your 10-year-old self cry if they saw you today?
Your passions as a child are a good signal of what truly interests you. Strip away all social expectations, judgment, and biases, and you’re left with your child-like curiosities.
Figure out what those things are.
e.g. Not risking to give my best effort to something I believed in, but not leaning so far into something where I neglect my loved friends, health, and happiness.
Fast forward to when I'm 80 years old. What did I regret not doing?
Picture being 80 years old. What are the 2-3 things you regret not pursuing in your 80 years of life?
Act on those things today to avoid that kind of regret at all costs.
e.g. Being more bold and more courageous. Trying my hand at something extraordinarily difficult to see if I could do it. Also, breaking free from norms to pursue what I am independently passionate about.
Light a candle, turn on some lo-fi music, grab a pen, and begin writing.
I hope this helped!
Ready to find your purpose?
When you’re ready to take the next step, I’d love to see if I can help.
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📌 Andrew’s Bookmarks
Fascinating internet things I’ve come across…
40 Lessons from 30 Years – an oldie but goodie. Nat is an excellent writer and shares 40 life lessons on career, relationships. and personal growth.
101 Additional Advices – another “life lessons” compilation that I really enjoyed.
Here lies the internet, murdered by generative AI – a more gloomy take on the GenAI revolution happening in front of our eyes. There’s a lot of content out there on how GenAI/LLMs will benefit our society but consider this contrarian take.
💃 Community Perks
🏨 Traveling for work? If you’re looking for a hotel with cozy rooms and social co-working areas, check out citizenM. I exclusively stay with them. They’ve even been kind enough to offer this community a discount. Reply here.
🚴 Discounted Equinox membership in NYC. Equinox is my second home - I couldn’t live without it. Reply here for a free trial and discounted membership.
🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyer I worked with for my O1A visa.
🍽️ FREE FOOD! I found an app that gives you 30%+ off fancy restaurants in NYC. AND $50 off your bill every month, plus $25 when you sign up. Not sure how long the offer will last. Sign up here.
What other perks should I include? Let me know.
🖼️ Behind the Scenes
My mom came to visit me from Canada this week, and I hosted her in my new apartment.
Growing up, we’ve never had much quality 1:1 time together (product of a traditional Asian household) and it was warming to spend a week with her and show her my life here.
We ate pasta, steak, pancakes, and waffles, saw "Book of Mormon" on Broadway, visited a jazz bar, and spent time with my girlfriend, Nicole, and her lovely puppy, Jasper.
Places we went (and my rating for each one):
Quality Bistro for dinner (4/5)
Devoción for coffee (5/5)
Gelateria Gentile for Gelato (5/5)
Bo Peep for cocktails (5/5)
Union Square Cafe for dinner (3.5/5)
Friedman’s for brunch (4/5)
The Smith for brunch (2.5/5)
Balthazar for brunch (4/5
P.S. one product that I credit for bringing me and my parents closer together: Storyworth. Check it out - I promise you won’t regret it.
