27 Personal Lessons From This Year of Living


Today, I turn 27. You might think I’m young or old. Until relatively recently in our history as Sapiens, it was rare for our species to get old enough to be grandparents. So I’m just glad to have made it here in good health.

I wrote a list of things I learned when I turned 25. Today, I continue with more personal lessons and experiences learned this past year.

Are you ready for all 27?

  1. Same idea; new perspective. What’s different about this list is that many lessons reaffirm what I’ve already learned. Experience is the best teacher. Even if I’m already familiar with a concept, there’s many opportunities to re-learn something with a new perspective. This year I want to re-read some of my favorite books, and delve deeper into tracks previously crossed.
  2. Identify where the fear comes from Much of my resistance in life comes from fear, in some form. Identifying where the fear comes from has been hugely helpful to me to chill the fuck out and have less anxiety. This thought pattern has been helpful to me: “How am I feeling? Why am I feeling fearful? Where is this fear coming from?”
  3. Touch is communication. Touch can be deeply therapeutic even in small amounts. An arm around a friend, a squeeze on the shoulder. Trying to make sure I don’t go too far.
  4. Prioritization is the enemy of perfection – yes, I came up with this one all by myself :p  
  5. I no longer have a travel itch… but I still want to travel. My itch to travel in the past was often anchored in escapism – not wanting to be where I was at the moment. But now I want to experience different cultures at a deeper level, to be more of an explorer-local than a tourist. I feel like I’ve seen a good amount of the world and can die happy, but alas I’m alive and can see more.
  6. Revealing abs: Set good macronutrients and track them. That got me 80% of the way there. I recommend using MyFitnessPal.
  7. Invite Mara in for tea – Tara Brach shared a memorable parable in which Buddha invites Mara, “the Evil One,” in for tea. When I experience negative emotions, this is a good reminder to not reject those emotions, but sit with them instead. This lesson has helped me be a better friend to myself.
  8. Presence is the mother of connection – Being present helps me connect to myself, which then helps me connect to other people.
  9. Releasing & taking control: it gives me peace mind to focus on things that are within my realm of control, and to let go of things that aren’t. I’m not responsible for other people’s actions, emotions, or how they react to me. But I’m in control of what I learn, who I listen to, and where I go. Letting go of what you can’t control is very freeing. I guess that’s why one of my favorite quotes (whether you’re religious or not) is: “God grant me the serenity to accept the things I cannot change; courage to change the things I can; and wisdom to know the difference.”
  10. Psychedelic experiences – everyone should try at least once. Reintegrating learnings – even a small fraction – can have an immensely positive effect on your life. But be careful, “the only difference between a drug and a poison is dosage.”
  11. Meditation is awesome. It also comes in many forms. The past year, I subscribed to Headspace and started meditating. I meditated over 200 days in the past 365 days, and the level of self awareness has been beneficial. I also learned that meditative practices can take on different forms, whether it’s lifting weights, taking a run, or even sketching. Whatever puts you in a state of flow and full engagement can be a meditative practice. However, for the average person I can vouch for the benefits of guided meditation.
  12. Starting small + being consistent has always been more effective for me than trying to summon a heroic effort to pull something off in one go. Humans, we are creatures of habit. I should take better advantage of that.
  13. Accountability and social deadlines work if there’s something big that you have to get done, set a deadline and make yourself accountable to at least one other person. Even more effective if there’s a huge disincentive to not follow through, like giving up money or an event you’ve already committed to.
  14. Bars and clubs are low ROI for me If I turn down your invite to go out drinking, don’t take it personally. The first reason is that I simply don’t drink much alcohol. I average something like 1 drink every 2 weeks. The second is that I prefer intimate spaces where I can hear the person and have a good conversation.I would go to a house party or housewarming over a bar ANY day.
  15. AirBnBs make for awesome group trips – thanks @ProductCharles for introducing me to the idea of taking retreats every other month or so. Sharing a nice AirBnB with friends makes for such a memorable, adventurous time.
  16. The benefits of planning a trip extend beyond the trip itself – I love the positive anticipation of upcoming trips & events. Having stuff to look forward to in the future is the easiest happiness hack.
  17. I learned to be productive when my brain is dumb – There were many wasteful nights when I had no energy but still tried to tackle work. I now know to save my focus for deep work, the type that takes a lot of cognitive lifting and strategy. When I don’t have that mental focus, I have a list of secondary tasks such as reading books, watching tutorials or answering email. These secondary tasks help me feel productive when my brain is on “consumption” mode vs “executive mode.”
  18. Improv is fun, scary as hell, and a metaphor for life – Improv is a hugely underrated form of present-state training. The best scenes aren’t the ones in which someone has an idea they want to rehearse, but rather it’s built from two players being fully engaged with each other and allowing the conversation/scene to develop. One of my friends swears that improv has skyrocketed his skills with women.
  19. Facing myself is still the hardest – much of my life and personal growth is driven by the relationship I have with myself. It’s easy to be distracted by external things. Whether it’s relationship problems or trying to tackle a goal, the true battle always lies within. So does true peace.
  20. I can drink milk – I used to be somewhat lactose intolerant and didn’t drink milk for ages. When I decided to bulk up, I added milk to my diet and prepared for rough times on the toilet. Turns out it had no effect on me at all. I was pleasantly surprised, but there’s a chance that lactose intolerance is just dormant waiting to strike back someday.
  21. I can better appreciate fluid relationships – My perspective on romance used to be more binary. Either someone’s with me (girlfriend) or they’re not. This year I learned to better appreciate the spectrum of relationships that can happen, and not to force things and let each connection unfold on its own. It’s been an enlightening exercise for me in un-attachment and staying present – for example, enjoying someone’s company instead of worrying about whether or not we’ll continue dating.
  22. There’s a certain season for things This is a longer version of the productivity hack called timeboxing. It’s difficult to start something new when I put the pressure on myself that it’s going to go on forever. Instead, I try to think of things in terms seasons – like an experiment I’m going to run for a certain amount of time. I might lift weights with a certain programming for a season or two. I cycle off dating apps, especially when they feel too distracting. Or I pick up a new hobby/skill and dedicate the next couple months to it. Having this perspective helps me adapt to new situations faster and recognize that I’m sometimes bogged by down activities that don’t make sense for me anymore.
  23. Understanding women a bit more This year, through traveling, dating and experiencing some fluid relationships, I had the opportunity to see some things through a woman’s perspective. The things they have anxiety over. They’re feeling of safety (or danger) in a certain place. The things they have to consider, that I take for granted as a man. I will never fully understand women, but I’m willing to learn.
  24. Focus on feeling good – When around some women I’m attracted to, I try to act too cool. This is my ego’s defense mechanism against rejection. I learned that instead of trying to be cool, I should focus on feeling good (and making each other feel good). Warm is always better than cool.
  25. Seeing conversations as an exchange of energy – rather than simply facts and ideas.
  26. Niche communities are amazing way to test and validate business ideas. If you see the same pain points and questions being asked again and again in a forum, Facebook group or Slack group, that can lead to some good product ideas. 
  27. Accepting I’m not confident all the time… makes me more confident I also used to be too binary about this. I had this thought that I needed to be confident about everything I do, or I’m not confident at all. I realized this was stupid, and that sometimes I’m very confident about certain things, and other times I’m totally not. Giving myself the freedom to fail and suck once in a while (or often) has been so much better for my psyche, and counter-intuitively, it has made me more confident.

And one more just for good measure… Don’t get gum surgery on your birthday – ‘nuff said.

The Only Dating Metric That Matters


If you’re a caveman and woke up with today’s technology, you’d be ecstatic. At first.

There are these things call smartphones, which have dating apps that allow you to look at and evaluate almost as many partners as you want. On top of that internet, social media and mass marketing that bombard you with images of unrealistically attractive pepole. And lest you get horny, you can have virtual sex with a limitless amount of porn stars, virtually for free.

Not a lot of actual work is required.

Let’s look at an adjacent example from the corporate world.

“A 2012 McKinsey study found that the average knowledge worker now spends more than 60 percent of the workweek engaged in electronic communication and Internet searching, with close to 30 percent of a worker’s time dedicated to reading and answering e-mail alone.” (Barking Up the Wrong Tree)

This has a name: pseudowork. It feels like work to you, but it doesn’t get you anywhere.

In dating, there’s a lot of pseudowork. Getting Tinder match notifications on the phone. Checking the OKC messages that hit the social tab of your Gmail. Texting that girl you’ve hung out with that one time, weeks back.

Many times, this feels like progress. All the conversations, emoticons, texts, flirty banter. It all feels like it’s going somewhere, and sometimes it does. The feeling of validation doesn’t hurt either.

But those are all the wrong metrics. The only dating metric that matters is…

the number of times you meet in person, face to face

Let’s consider this for a moment.

When you’re dating, the one true thing that really matters is how often you meet in real life. The number of times two people meet already indicates sufficient attraction and connection between them.

Practically speaking, using the number of times met metric removes a huge chunk of stress from your dating life:

  • Wondering about the mixed signals she’s sending? Doesn’t matter if she doesn’t meet up with you.
  • That confusing/sweet text he sent you? Texts are pointless if you two don’t meet up.
  • Infatuated by that girl you met at the club? It means nothing until you see each other again, outside the club.

I’ve been in that anxious state before, hingeing on to every text a girl sends. Does that mean she likes me? What does she mean? Thinking in terms of # of times met acts like a system-override, reality-check button button for me. If someone continues to see me, they care. If we don’t ever see each other, we can hardly claim that we really care about each other.


I want to get serious for a moment and underscore how important this is.

Why does it matter so much to meet in person? It’s not only because nice things like touching and sex can’t happen online.

It’s because presence is the greatest gift we can give each other. 

Break out the tree bark, cause I’m about to get sappy.

  • When you’re in a hospitable bed, there’s nothing more you want than to have a friend stop by.
  • When someone dies, you think about the last time you spent time with them.
  • When you die, you think back on times spent with loved ones.

Your greatest resource is your time.Brian Tracy

Time is the greatest resource and the scarcest. Time is life. When you show up and meet someone, you’re literally giving away a piece of your life. And when you treat your own time and life with that much value, other people can’t help but sense it and respect you and your time.

Eighty percent of success is showing up.Woody Allen

So that’s my treatise, folks. To date more happily, just worry about the one metric that actually matters.

_ _ _

Other Considerations

1. But what about long distance relationships?

Even long-distance relationships start with a series of intense meetups to establish a baseline of intimacy, until one partner or another has to move away.

Does this mean two World of Warcraft players can’t fall in love over the internet? Of course not, that can happen but it’s by far the exception.

The higher the amount of upfront investment, the longer that two partners can reasonably be apart. For example, many of my friends have fathers who’ve started businesses abroad, leaving wife and kids home in ‘murica save for a handful times a year. But typically, the husband and wife have spent years together building up their relationship before making a life change like this.

Here’s what relationship guru Mark Manson says about long distance relationships:

“You don’t get a sense for the actual relationship until you’re there, in person, and in each other’s faces non-stop, whether you want to be or not.”

2. Maybe you’re jaded because you’re from LA 

Some friends argue that I’m jaded about dating in Los Angeles. “In places like New York, meeting up with people is so much easier.”

I retort that this doesn’t change the # of times met metric for dating – it may just be easier to increase that metric in different dating markets.

Let’s put it this way. Show me two different pairs of daters. One pair has seen each other twice over the past 5 weeks. The second pair has seen each other every week over the same time period, sometimes even catching a two-fer in week. All things being equal, who would you bet your money on to turn into a couple?

I’d bet my money on the second pair every single time.

Issue 1: Curated Reads for Men’s Personal Development


You haven’t heard from GuyGuides in a long time, but we’re back from the dead. This time, with something new (other than a new look):

Curated articles on men’s personal development, delivered fresh to you weekly. The format is simple: once a week, get a trove of the best articles that we hand-pick, along with a blurb of why we selected that content.

It may include quotes, key takeaways, or a particularly good point about why 20-somethings are so obsessed with themselves (smirk).

Finally, a tropical island amidst a vast ocean of social media. The service is for those who want to read truly good content, which we deem to be as such:

  • insightful – all curated articles must contain at least one useful insight or story
  • balanced and mature – no content demeaning either sex or valorizing the YOLO lifestyle. I’m talking about you, Elite Daily.
  • minimum list articles – if we do come across a good “listicle,” it better be the best damn listicle you’ve read all month.

With that, I’m happy to announce the First Issue: Curated Reads for the Attention-Deficit (Male) Brain

Thanks for continuing this journey with us.



Stop Wasting Your Fucking Life (Johnny Wolf)

Starting with this piece really sets the tone for the rest of the weekly curated articles.

But if you’ve been in the pick up community for more than a year and still haven’t actually improved your life. Get out. You are wasting your fucking time.

Johnny Wolf is the moniker of a (former?) Asian pickup artist who’s actually pulling away from the pickup community. While he credits PUA for making men more motivated and entrepreneurial, Johnny also cautions how focusing on tangible goals like starting a business or working on your physique can do way more for a man’s confidence and lifestyle than just practicing “picking up chicks.”

The Incessant Tweets Aren’t Helping You, Man (AskMen)

This piece reads a bit prescriptive, but the overarching point is a fresh reminder to mute the incessant notifications and put the smartphone away once in a while.

A lot of men – especially those in new relationships – feel compelled to spend every waking moment with their bae. This may lead to an exhausting upkeep of texts, tweets, Facebook tags and likes. But remember – she doesn’t need to know everything about you, and vice versa.

An air of mystery will gradually entice a woman to subconsciously make an effort to find out more about you; what’d compel her to exert the effort if everything she could ever want to know was retrievable from a quick click to a history of your 2013-2014 timeline with everything you’ve ever done, ever?

Fixed vs. Growth: The Two Basic Mindsets That Shape Our Lives (Brainpickings)

In high school, my best friend shared something interesting with me. He told me, “I wish my parents never told me I was smart. I think that made me lazy.”

Turns out, my friend was 7 years ahead of the game. Maria Popova highlights research on the difference between praising children for their ability (“You’re  so smart”) vs their efforts (“Good job, you must have worked hard at it”).

The former group, on average, becomes interested in protecting the status quo of being smart, and thus want to minimize mistakes. This leads to what the author calls a fixed mindset. The groups praised for their effort were shown to appreciate mistakes as learning opportunities to grow and become better . Thi leads to what is called a growth mindset.

There’s a lot more to the article that just how to praise your kids, so give it a read.

How to Avoid Decision Fatigue (Tim Ferriss Podcast)

I’m the biggest fan of Tim Ferriss and not shy about it. This short podcast (I would start at the 4:30 mark) on how to avoid decision fatigue is especially intriguing and useful.

The main takeaways:

  • Willpower is finite, and it needs to be protected. As the # of choices you have to make go up, the more it drains your willpower.
  • Systematize the # of unnecessary decisions you make.
    This is why Obama and the late Steve Jobs always repeat the same outfit. Similarly, I never think about breakfast because I just drink 30grams of protein (also from Tim Ferriss) every morning.
  • Start small: decide what you’re going to do for the first hour of your day, which may include what you’ll wear, eat or read.

How to Master Your Time (Oliver Emberton)

Oliver mother-effin’-Emberton. I love his in-depth posts and his stick figure drawings. In this article, he simplifies time management not through a series of tactics, but focusing on the fundamentals: what tasks should your prioritize?

The secret to mastering your time is to systematically focus on importance and suppress urgency. Humans are pre-wired to focus on things which demand an immediate response, like alerts on their phones – and to postpone things which are most important, like going to the gym. You need to reverse that, which goes against your brain and most of human society.

This is one of his best articles on identifying the subtle, but huge difference between doing urgent things vs important things. Choose the latter.

Jim Carrey’s 2014 Commencement Speech at Maharishi University (Youtube)

I’ve always loved the darker, more serious side of Jim Carrey a la Eternal Sunshine or The Truman Show. In this video, Carrey gives a crap ton of sage advice in a highly motivational speech.

The speech was so good, I filled up a page of notes. Here are some of the quotes that struck me:

  • You can fail at what you don’t want, so you might as well do what you love
  • The effect you have on others is the most valuable currency there is
  • Your need for acceptance can make you invisible in this world
  • Risk being seen in all of your glory
  • I was concerned with going out into the world and doing something bigger than myself, until someone smarter than myself, made me realize there was nothing bigger than myself
  • My soul is not contained within the limits of my body – my body is contained by the limitlessness of my soul
  • No matter what you gain, the ego will not let you rest. How tricky is this ego, to tempt us with something we already possess?
You will only have two choices, love or fear. Choose love. And don’t ever let fear turn against your playful heart.

And I want to gratuitously title this part as “How to Be Successful:”

  1. Tell the universe what you want
  2. Work towards it
  3. While letting go of how it comes to pass

Things I Do Have Instead (mmlist)

Each new Thanksgiving seems to bring with it a renewed focus on consumerism, with ridiculous new antics like stores opening on Thanksgiving Day.

Reading someone else’s gratitude list (my term for the opposite of a wish list) brings a new perspective, and I thank Leo Babauta for that.

Here’s my own shortlist of things I already have that I’m grateful for (nothing is too little):

  • A career doing something I actually like
  • My minimalist backpacking setup
  • Airport miles that let me travel for pennies on the dollar
  • Good mentors, caring friends and a loving family

_ _ _

From the GuyGuides Vault

How Pickup Artists Market to Men

This article delves into the darker side of pickup artist industry works by promising instant results and making men chase down a fruitless path of pickup “tactics” and “skills.”

Some takeaways:

  • Internet marketers appeal to people’s lazy side: get instant results with minimal effort (“Get laid after 1 weekend of my workshop!”)
  • The industry survives by making men think they always have to learn just one more tactic or trick to get women. In reality, it never ends – there’s always one more thing you can do.
  • It’s interesting that you almost never see PUAs bragging about healthy, long-term relationships.

_ _ _

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How My Douchey Profile Won Tinder

It’s hard to define doucheyness. Some guys can rock the summer tank top no problem and others…it sets off the douche-alarm immediately.

But if you take a step back, more than anything, it seems to be a combination of two things:

  1. Blatantly soliciting attention in a contrived way – any dude in a sports car, wearing Oakley’s; wearing jeans and jeans only to a rave; being that guy who brings his own guitar to parties.
  2. “Trying too hard” or incongruence – any white guy wearing traditional Asian garb for basically any occasion that isn’t a Japanese tea ceremony (Steven Seagal, I’m lookin at you).

From casual observation: the douche factor is rising.
And here’s the case for why:

Simply put, being a douche must get results. Standard behavioral psychology. If the behavior is rewarded, it will happen more. In the interest of science and easy poon, I took to Tinder, hypothesis in tow.

The test itself was relatively simple.
With a sample size of n=200 for two very different profile pictures, how much more likely was I to get a match (i.e. initial attraction) based purely off my level of douche.

Each wave, I would use a different picture. The user profile was the same in both cases.

Picture 1) Understated, black and white, dressed in a vest and tie. Normal, almost standard Facebook profile picture.


Picture 2) Over the top abs everywhere, surrounded by women. My old housemate was originally in this picture, but his abs were nicer than mine so I cropped him out. Again, for science.



After long periods of the mind-numbing boredom that only “incessantly swiping right on Tinder” can prove — I arrived at the following:

Doucheyness wins by a goddamn landslide (ladies, y’all are just as shallow as we are). I not only made almost 3x the amount of connections, but I also connected with more women to whom I was physically attracted.

Now this isn’t a guarantee of marital bliss or even successful dating for that matter, but even playing this as a sheer numbers game and doing nothing to intentionally spike interest, as a doucher, I come out WAY ahead.

Is there a lesson here?


Sometimes your success is more important than how you appear to other people. Maybe even all the time. If I am looking for my soulmate and I succeed…are the strangers I weird out along the way even relevant?

It just makes the most sense to play to your strengths.

Do you have to be tryhard or incongruent with it? No. Absolutely not. But you should be putting yourself in  position to naturally utilize those strengths to your advantage.

  • Maybe you ARE awesome at guitar. Well bub, it’s time to start hitting up open mic nights at your local cafe.
  • Maybe you’re rich. Show you use your wealth for more than just your own well being.

Being a douche works. But bringing actual, unpretentious, PURE value to the table — it just feels so much better. Oh and it works better, too…probably. But that’s a test for another day. Till then…happy Tindering.

Over and out,



How to be Disgustingly Good at Small Talk

*This new post is by new GuyGuides wordsmith, Rob.

To be a good conversationalist. You need small talk.

  • Maybe you don’t want this skill set.
  • Maybe you think being a chatty person is the same thing as being an annoying person.
  • Maybe you think it’s beneath you to make small talk and you’re all about “deeper” conversation


Here’s the thing. If you’re nodding in agreement, it probably means you’re awkward as fuck. No hard feelings. Nearly everyone is.

Conversation is something everyone thinks they’re good at. For about half of you, that’s not true. For an unfortunate 5% of you, that’s a lie of such monstrous proportions it puts the North Korean propaganda machine to shame. (golf claps and begrudging nods of approval for you)

The thing is when we talk, we gauge our abilities off when we talk with our friends. That’s cheating. You have history with your friends. You can read their micro expressions.

It’s easy to keep the ball rolling because you know their past, their present, ambitions, and are mutual friends with their cat on Facebook.

With strangers, suddenly that crutch is removed and every so often you’re left poking them with the question stick until it’s time for everyone to awkwardly leave. Even people who weren’t involved. It’s just that bad.

Again. No hard feelings.

Running into someone who can actually hold a conversation is borderline miraculous. It’s enjoyable, fun, and endears you to them. Everyone has a friend they enjoy hanging out with because conversation flows so naturally with them (and not so naturally with others).

What most of us don’t realize is that conversation flows easily because those friends facilitate for your flawed communication. Whenever there would be an awkward lull, they pick up the slack for you. No fear though. This isn’t really your fault, and is something everyone is capable of fixing.

Even better, conversation is the most scalable skill you will ever learn. It is SO useful and applicable so universally, it’s unreal. Literally every encounter you have with another human being is an opportunity to connect with someone who can add value to your existence.

Everyone is amazing at something, and you’re missing out when you don’t or can’t stop and figure out what that is.

Once you even attain a baseline competence at this…you will look like an amazing person and people will want to have your babies*

So how do I inspire baby fever in perfect strangers? The first of many steps is holding their attention. This involves learning how to talk like you’ve got the worst case of ADHD you’ve EVER seen.

Step 1: Begin talking about something you see.

Step 2: Once you’re warmed up, transition over to another related subject

Step 3: Now transition again.

Step 4: AGAIN.


Step 6: Now keep doing this for an hour a day for 6 months.

On transitioning: All you’re doing is simple word association and then talking about it. If I started off on apples it’d be easy for me to transition into apple cider, and then how apple cider reminds me of Christmas, and then to family holidays and how no one in my family can handle their booze because we’re all “asian glow” happy. Then I could talk about how the UCSD VA used to run a research study where they got Asians drunk, etc. etc.

As you go, you’ll find that you’ve naturally become higher energy, more interesting, and generally more attractive as a human being. This is a pain in the ass, and WILL make you look like a crazy person unless conducted in a contained environment.

I like to save this for my commute to work, but if you don’t like your neighbors and/or generally don’t care how obnoxious you get, feel free to do this in public. The extra pressure will help you improve faster….probably.

If you pay attention to any good conversation, you’ll notice it’s an exchange of statements, not question and answer.

What you’re doing through this brain hack is reprogramming your brain to run with any topic and smoothly transition into new ones with less effort. Over time you’ll develop the ability to not only tread water indefinitely, but to make it massively entertaining.

You’re welcome.


*Unless you’re a ginger. Then all bets are off.