Matt Yao
@matt__yao
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1,711
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🧭 Wayfinder Coach: ✍️ Essays: 🐌 Helping @schlaf build @Downshift_me
NYC and Tahoe ⛷️
Joined April 2019
Don't wanna be here?
Send us removal request.
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It's been over a year since I quit my job and went on sabbatical!
In my newest blog post, I reflected on the entire year and covered the 4 phases of my sabbatical as well as how I've grown in key themes like money, work, identity, uncertainty, curiosity, healthy, and
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since quitting my tech job I've unfollowed all the VCs and started following random people who just tweet about their feelings and the meaning of life lol
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9am: yoga
11am-4pm: reading + writing in the cafe with weak coffee but strong A/C
4-7pm: surfing until the full moon replaces the sun as our light source
$11 homestay, $7 yoga, $3.5 surfboard rental, $5 boat ride to the surf
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it's a huge privilege to be forced to be frugal (I make no money rn) yet have zero worries about my long-term finances (worst case I just get a job)
my relationship with money has been reset in a healthy way and now I'm figuring out what I actually value
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considering sending a quarterly-ish email to friends + fam + mentors + professional connections
kinda how startups send updates to their investors, but also not really
a combination of what I've been up to, what I'm consuming + creating, ways to help me
has anyone does this?
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I've been living off sublets for 4 years
Finding sublets is tedious, but the flexibility and lower cost is worth it
Recently, friends have been asking me to help them find sublets but also list their places so they could travel
This led
@0FJAKE
and I to start The Subletter 🏠
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NYC is the only place I’ve lived in where I’ve highly ambitious and highly creative which is why I’m based here now
SF has plenty of ambitious people but fails to recognize value of things outside tech
I felt creative living in Hawaii or in the mountains, but lacked drive
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@seanrose
working next to friends in a wework who all work at different companies has major college library vibes (in a good way)
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1. Here in SLC for a week of solo skiing + solitude
2. Wanted to get a upper body lift in mid-week
3. Look on google for gyms that offer day passes
4. Find a nearby gym and drive over but no one is there and the door is locked
5. Call the number on google maps and this dude
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I have reduced my cost of living by 40% since quitting my job with no noticeable decline in perceived happiness
My life is less convenient and less extravagant, but those things are less important to me now because I no longer need as much convenience or material things
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I’m stoked to share that today
@0FJAKE
and I are launching The Subletter, a marketplace for finding and hosting sublets!
For the last 4 years, I’ve been living without a lease. This way of living started in March 2020 when I moved to NYC expecting to be there for 6 months for
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We need more ways to experiment with work. Quitting your job / taking a break / going on sabbatical / traveling the world is amazing and more of it is needed in the world, but it doesn't directly solve the separate-but-related problem of not knowing what to do. Leisure and work
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it's mind-boggling to me how we all want more time (quantity)
and at the same time, the best quality time is in flow state where "time flies in the blink of an eye"
the best way to spend time is when it goes by so fast 🤔
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I'm excited to share that I'm starting an apprenticeship with Steve Schlafman (
@schlaf
)!
This marks my first step towards the coaching path and reinforces my commitment to a lifetime of learning.
Here's how I thought about coaching, apprenticeships, and finding the right
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I quit my job! 💥
Walking away from my Senior Product Manager job took me over a year from initial seed to actually quitting. Along the way I meticulously documented my thoughts, emotions, conversations, and helpful resources.
Shared it all here:
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friend asked why I'm in nyc if I'm living off savings
it's bc I switched from defense to offense
conserving cash -> in pursuit of something
nyc is an accelerant for what I want, the city equivalent of a triple shot espresso injected directly into the veins
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solo travel and quitting your job are similar because you craft your entire day down to every moment
it's a crazy dose of freedom, agency, joy for anyone who's been living under someone else's constraints for a while
only realizing this bc I'm doing both at the same time rn
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In my coaching practice, I found a common pattern: my clients are all mid 20s-30s ambitious high-performers who have already achieved conventional success relative for their age, already sense there's more to life, and they each possess a latent creative energy dying to emerge.
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working hard on things you care about >
not working hard, but knowing what you care about (low energy/in a rut) >
not working hard, but also don't know what you care about (feeling lost) >
working hard on things you know you don't care about (grinding, investment banking)
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Ran the NYC marathon in 4:00:51 and finished raising $3k for autism research on Sunday
My first race longer than a 5k which was probably ten years ago
Thanks to everyone for the support 🙏
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Reversing the Hedonic Treadmill 🏃♂️
My first three nights in NYC consisted of crashing on my friend’s air mattress in her A/C-less apartment. Facing a busy street, the window was propped open so a fan could blow out the hot air. Since I had earplugs with me, I made the tradeoff
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My friend's neighbor became an empty-nester and decided to finally commit to mountain biking. They're in their 50s and upper-middle class so they were able to afford a high end bike with all the safety and comfort add-ons.
But once they actually hit the trails, they realized
Guy plans to do more sports when he retires, then at age 46 realizes his body can't take it
There are seasons of life -- be sure not to miss yours
What's something you want to do this decade that would make your life incredibly rich & meaningful?
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in one of my recent blogs, I casually mentioned my 1,000 calorie, 70g of protein oatmeal recipe that I eat almost everyday for lunch
two people have emailed me about the recipe so I feel compelled to share
tips:
1. mix everything up a few hours before eating so the oats and
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Two ways to live:
1) Make $$$ and then figure out who you are and what you love
2) Figure out who you are and what you love and then work out how to sustain your ideal life
I'm going with the latter. I think figuring out what you want in life is harder than making money
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For almost a year, I've been tinkering with the idea of taking a career break. As someone still early in their career, leaving the corporate world for an undefined period of time is daunting.
... so I reached out to 16 friends who have done it already
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We are not meant to stare at screens 8 hours a day
Recently have made the switch from zooms to phone calls
Not for every situation, but most
Instead of spending the late afternoon cooped up inside and straining my eyes, I went to the park and enjoyed the sunset
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“I used to judge my success by how many unpleasant things I could force myself to do. Now I judge my success by how few things I have to force myself to do.”
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working on my next climate newsletter when this guy strikes up a conversation when he saw “climate” on my paper
turns out he’s a French physicist who quit his job in 2020 and has been researching (and surfing) the oceans for his entire career
serendipity strikes again
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saw a cool job posting just now and thought hmm maybe I'll just apply out of curiosity
got to where you upload your resume, realized I had to update my resume, opened my resume in its current outdated state
and became aware of how foreign the idea of a resume is to me now
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@SchrodingrsBrat
“Every time you're given a choice between disappointing someone else and disappointing yourself, your duty is to disappoint that someone else. Your job throughout your entire life, is to disappoint as many people as it takes to avoid disappointing yourself.”
―
@GlennonDoyle
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I’m often misunderstood because I’m trying to figure out the life I want to live and then making it sustainable over the long run ($) while the typical way is the reverse: make a bunch of $ and then figure out what kinda life you want to live
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dude at the gym is reading Meditations by Marcus Aurelius in between sets
not sure whether to be intimidated, confused, or in awe
but he’s also drinking a red Gatorade so that probably cancels things out
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why does it seem like there's a New Grad phase of life which is 22-25ish and then a Settling Down phase of life around 29ish-35ish with a nebulous in-between phase
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since leaving my corporate job with stable income just a bit over a week ago, I've already noticed my relationship with money changing in unexpected ways
I didn't know what to expect but intuitively thought that living off savings would make me worry about money more, but the...
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two things that have surprisingly changed my relationship with money
1) traveling to SE Asia, India, LatAm and realizing that people w far less money are just as happy as me
2) backpacking - enjoying time in the outdoors (costs $0, can always do more if I run out of money)
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something I haven’t seen much on sabbaticals:
my physical health has never been better, not due to having more time, rather more energy and ability to fully direct my attention
you can “find yourself” while also “getting your shit together”
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@krishnanrohit
yeah I’ve sorta had to put the blinders on to social status (might be a good thing to do regardless) and also find other people doing the same thing (quitting their tech job to rest/wander/explore)
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when I see a friend pursuing something that they truly care about, it almost feels like it's my duty to encourage them
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5 months into sabbatical:
most challenging: consistently not meeting my own expectations + self-imposed deadlines for when I'll get stuff done
best thing so far: how fast I'm learning, it feels like I went from linear to exponential, all from unbounded self-directed curiosity
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lately when I work has become intertwined with nature rather than 9-5 Mon-Fri
when conditions are good: I ski
when they’re not or my legs need to rest: I work
it’s been snowing a lot so I haven’t been working much 😬✌️
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in the context of being on the wrong path, the benefit of skill acquisition is overvalued and the work associated with untangling identity sludge is undervalued
people will often stay in the wrong path even when they know it's not right for them because they believe they're
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I graduated in Dec 2018 and had my first job lined up to start Aug 2019. The 8 months of freedom combined with the certainty of my next thing was magical. I went to Taiwan + China with family, hiked the Inca Trail in Peru to see Machu Picchu, backpacked in Patagonia, and lived in
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writing a well-crafted sentence is incredibly satisfying like a deep tissue massage or biting into a juicy apple
on the other hand..
a poorly written sentence sits with you like a pebble in your shoe, water stuck in your ear, having to burp but not being able to
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Full circle moment joining
@schlaf
on
@p_millerd
’s pod tomorrow ☺️
I credit The Pathless Path as the first domino that led me to leaving my past life and starting this new one.
I remember the feeling of sweaty hands while talking to Paul on the phone because it was the first
Big day tomorrow!
@matt__yao
and I are joining
@p_millerd
on the Pathless Path pod to talk about apprenticeships,
@downshift_me
, and whatever else emerges.
This is a long time coming. Very excited.
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recently re-learned that when a caterpillar is undergoing metamorphosis and is in the chrysalis, it literally dissolves into mush
and that's how I feel rn being actively unemployed or in "hard leisure" mode, a pile of jobless goo that will hopefully turn into a butterfly - tbd
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hot take: if posting pics of food was somehow banned, avg frequency of dining out would decrease
part of going out to eat is signaling that you have enough money + time + friends to eat out
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w/ daily journaling, this one question has been coming in clutch:
"What's 1 thing I'm avoiding"
usually it's a task that is <5 min to complete but is mildly uncomfortable, I've realized that once I write the thing down, the activation energy lowers and I just do it right then
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my hunch is that a lot of people would rather take a job that pays 1/2 as much in return for 1/2 the time
$100k job for 20 hrs / week seems way more appealing than $200k for 40 hrs / week
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in doing my own thing (I still don't even know how to articulate it), one of the most counterintuitive things is the collaboration + community
you'd think that individuals each on their own path would feel isolated, but I've felt more connected now than when I was an employee
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"The most valuable real estate in the world is the graveyard. There lie millions of half-written books, ideas never launched, and talents never developed. Most people die with everything still inside of them." -
@sivers
ooooof this hits
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I'm running the NYC Marathon on Nov 5th🏃🏻♂️
as someone who hadn't more than 6 miles in July, it's been a fun, but demanding training block
my latest blog:
Simple, Hard, Enjoyable - The 3 Ingredients to Earned Success
full post is in my bio!
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commitment is paradoxically freeing because once you decide you must do something, the effort decreases
it's easier to fit things that you need to do into your day than having to decide whether you're going to do it or not
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Only 2 months in, but I'm spending significantly less than I budgeted for when deciding when to quit my job
I budgeted based on what I was spending at the time, but since I quit, I've cut spending on things I stopped caring about like dinners, drinks, trips not with homies
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Most of my friends don’t want to be digital nomads 100% of the time, but would really like to live more flexibly than they do now.
Instead of constantly bopping around from place to place, they wish they could just take 1-3 months a year to travel, avoid the harsh seasons,
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the ideal work environment is living walking distance to my friends and we rotate hosting everyone else (if we all had big enough places)
each person working on their own project
and the host makes everyone coffee and slices fruit like an Asian mom
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a lot of people including myself say they have a hot take but then it's not that hot, it's more lukewarm, but now I have what I think is an actual hot take:
video games are net negative on society
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There are two types of friends:
Type 1: deep, introspective conversations, long walks in the park, hanging out on a friday night doesn't come with the assumption that it involves drinking, compare meditation and journaling practices, read each other's blogs, send voice memos,
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in multiple words: redwoods, yoga, sunset run by the ocean, group meals, bonfire, falling asleep to the rain, reflecting on the year
in one word: vibezzzzzzzzzzzzzzzz
Make inspiring, impactful things with your friends is my favorite takeaway from 2023. Rounded out the year doing just this and carrying this intention straight into 2024 ☺️
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looking to talk to more folks who are living in interesting ways!
hmu if any of these terms resonate with you / if you're living in any of these ways:
- seasonal living
- digital nomading
- living in airbnbs
- subletting
- multi-place permanence
- bicoastal living
Introducing Subletter Stories!
A series of tweet-sized interviews with people living outside of the 12-month lease.
Saalik (
@SaalikLok
) and his wife are currently exploring Asia with Taiwan as their home base.
Their story below 👇
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a simple but kinda dumb strategy to find work that you love is to work for free
if you worked for free and didn't like it, you would intuitively stop doing it
if you work for free and enjoy it, then all you need to do is figure out how to make money from it
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It took me 10 months to quit my job. Then it took me 5+ months of experimenting to find my new path.
People talk about this thing called 'intuition' all the time and it has always seemed pretty abstract to me.
In the context of decision making, I think it's less about going
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I was reading at a cafe, sharing the long table with a mom and two kids and I could tell she felt like her son was disturbing me but it was chill
I started talking to her and turns out she's Indonesian but was in the US for 12 years
she told me her son has asperger's..
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run club, writing club, reading club (different than book club), journaling club ++
something is going on here
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the process!
fractured my fibula 5 weeks ago while skiing
declined surgery despite a slight displacement
went to the ortho today and looks like it is healing better than expected, the displacement somehow self-corrected itself
went for my first proper walk outside today in
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@rrhoover
VR hardware repair person
VR experience becomes good enough for mass adoption and then a bunch of people start running into walls and breaking their stuff
kinda like what happened when the Wii first came out and people were throwing their Wiimotes into the wall
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Committing psychological warfare on myself by rewarding myself with two almond butter pretzels for every 30 min of writing
These are 2x the price of the peanut butter variety but 5x tastier
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looking all the untouched items on my to-do list wondering how the day went by so fast and realized I spent 4.5 hours calling people I care about so it was still a "productive" day
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big enough for random strangers to send me positive messages, small enough to read and respond to each one intently
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have been in nyc for 3 days and now I remember why I want to live here
my brain feels like it’s on fire in the best way possible, I have met more people in 3 days than 3 weeks in other places
here for the next month! hmu if you wanna hang :)
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making plans and setting goals are substitutes for action and belief in yourself
extreme example:
if you had 100% confidence in yourself, in things working out, in the universe, then you wouldn't need to plan your future or set goals which are at best approximations of reality
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great day so far:
- recorded a podcast
- new bench PR at the gym
- session with my meditation coach
- interviewed founder of Maui Nui Venison for my climate newsletter (which I was kinda nervous about because he's been on Tim Ferris and Peter Attia's pods)
later today:
- dinner
Full circle moment joining
@schlaf
on
@p_millerd
’s pod tomorrow ☺️
I credit The Pathless Path as the first domino that led me to leaving my past life and starting this new one.
I remember the feeling of sweaty hands while talking to Paul on the phone because it was the first
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Luck Emerges in Positions of Uncertainty
I recently changed my mind on luck after experiencing enough positive unexpected moments that I knew it couldn’t be due to pure chance. I savored a private 9-course tasting menu at one of NYC’s finest Italian restaurants, free of charge.
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While it may seem like it's "just a newsletter", it's just the beginning.
Unlocking the most expensive component in cost of living enables people to optimize around seasons, travel more often, and stay closer to family.
Learn more by visiting the newsletter (link in bio)
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not having to set an alarm is a type of wealth and a sign of health
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It has been 15 months since I left the corporate world and my past life in tech where I finally feel like I have focus. There's a much smaller number of things that I'm directing my attention towards right now. I feel good about the things that I'm focusing on. I feel a bit of
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I am realizing that there are fewer and fewer things that actually matter
and the things that matter, matter more than I previously thought
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I wanna start a service where I show rich people how to have fun with less money by charging them money and then taking them to do fun, cheap things
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@girdley
the new suit is having a high quality zoom setup with not just upgraded mic + webcam but also a carefully designed background and having the camera at the right angle
tired of seeing CEOs / rich people on video calls with the laptop cam pointed up at the bottom of their chin
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I think the dichotomy of nature-lover vs. city-slick is false
friends have asked me why I want to be in NYC when I like surfing, skiing, backpacking so much
I think I'm just drawn towards intense environments - each with their own unique raw energy
Tetons
Kauai
NYC x2
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the fact that these supplemental products exist says something about our default relationship with modern tools
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meet lawyer friend at 9pm
he arrives with backpack, I ask if he came from the office, no he came from his apt, but has to have his laptop just in case
carries 2 phones around at all times, checks apple watch every few min, we hang for 45 min before he leaves to do more work
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@brelow
nah not really, it’s been a week lol
but I think this is part of the process to bring myself closer to my authentic self
the content you consume is a mirror for who you are in that snapshot of time
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feeling lost -> productivity hacks to get more “free time” -> still feeling lost -> turn to philosophy/spirituality/religion -> realize it’s not that deep -> figure out what a good day means to you and just do it over and over
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met a guy on a chairlift a couple weeks ago who mentioned he runs a ski shop, came by today because I needed a full tune up ($70-100), he hooked me up, refused any payment
now I’m gonna go there every time (and bring my friends)
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As I continue to wade in uncertainty during this liminal period, I'm starting to learn the importance of focus
Only in the last couple weeks have things started to feel like they're "working"
Now I need to simplify, reduce, and focus for things to actually work
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opposite seems to be happening
I'm not sure why, but I'm starting to increasingly view money as a tool to help create the ideal environment / vibe that I want to live in vs. viewing it as an asset that I invest in order to plan for my retirement
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This tweet led to a 7 hour 1:1 private tour of Singapore including free entry to 3 museums because the guy is a docent
any question would get answered instantly and my brain was on fire the whole time
I slept 10 hours last night as a result
he also wouldn’t take my money
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I quit caffeine a month ago and also quit alcohol about a year ago
wrote about it through the lens of self-reliance
link in bio
a lil snippet:
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This is what I've been up to the past couple weeks. It's been a lot of fun to work on something so aligned with my experiences, interests, and skills.
I've also been having more conversations with people who are interested in sabbaticals, winding down their startups, or having
I'm thrilled to announce the launch of Downshift, the world's first decelerator program tailored for high performers in transition.
Downshift is a transformative, 8-week journey aimed at fostering presence, self-discovery, and renewal.
Designed for diverse professionals who've
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@soren_iverson
need to add a ruler on screen otherwise dudes will buy small furniture just to look bigger
same dudes that are 5' 10" and say they're 6'
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observing my lawyer and banker friends attempt to port over hustle culture and brag about how much they worked
"I've been working 14 hour days"
"sorry late response, pulled an all nighter"
within these circles it's a status signal, but I'm just like ok cool?? get some sleep?
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