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.

Finding Freedom in Structure

Thanks to an email sent from Deltasig Bro, I was able to catch Ramit Sethi’s and Tim Ferriss’ LiveStream today. Let me tell you, the learning experience is completely different when you’re listening to your two favorite authors/life coaches over webcam. Something that stuck with me from their LiveStream is the practice of having rituals.

Tim Ferriss says one of his rituals is to wake up every morning and have 30 grams of protein. It’s automatic and gives him a kick start to his day. Besides the physiological benefits of protein consumption, Tim and Ramit argue that there’s something powerful in having rituals – it provides focus and structure to one’s life. I think this is really counter-intuitive because habits and rituals often seem like they require massive amounts of self control. They don’t. You have a habit of logging onto Facebook the moment you turn on your laptop. Does that take much control?

We admire early birds who wake up at 5AM, run 2 miles and finish a blog post before others get up from bed. I myself have wondered: “how do these freaks of nature do it? They must be so disciplined.” The truth is that although habits are hard to form, once solidified they actually give much-needed structure in the chaotic lives we lead. Good habits make life easier. Those freaks of nature wide awake in the morning actually depend on their 5AM ritual and other rituals conducted the night before. They know too well that sleeping in one day until 7AM, then 6AM the next, will make them tired and subject to the same mediocre habits that govern most of their peers.

It’s been almost 2 years since I’ve read the 4-Hour Body. And I’ve pretty much had the same diet these past two years: every meal consists of meats, veggies and/or beans. One cheat day a week. I don’t drink calories. And yes, like Tim I consume 30 grams of protein upon waking. People have commented that my diet is boring, or that it must take such self discipline to eat pretty much the same damn thing every day.  The truth is, I need to eat like this now. This ritual makes it brainless for me so I don’t need to expend energy thinking about what to eat next. I find freedom in this structure, as opposed to the dietary prison others assume.

I want to learn from you and ask – what kind of rituals do you have that give you necessary structure in your day-to-day? I’d love to know.  It’s time to develop some more good rituals J

To Be, Or Not To Be (Together)?

[quote]He said he wants variety. The irony is that I wanted variety too. But I wanted variety in a solid, stable committed relationship where I would wake up each morning asking “What are we going to do today?” not asking “Who are you going to do today? – Aimee Lane[/quote]

I think young twenty-somethings often go through this dilemma: should I pursue a relationship with the one I’m dating or keep dating around?

I don’t have an answer. But one conversation with a friend brought forth many good points about dating in our twenties. Let’s explore them.

The Single & Casual Dating Life

Single life can be beneficial to a twenty-something’s personal development. You develop independence. You have flexibility to date around and schedule plans as you wish. This is great if you’ve been hopping from one relationship into another. Being single can also help solidify an identity of your own, rather than just being someone’s boyfriend/girlfriend.

Variety is another pro. You get the luxury of dodging emotionally unstable people before committing. It’s fun to date around and open your eyes to the possibilities of who you can date. You have more opportunities to test the question: what kind of person am I looking for? And I don’t think it’s ever too early to start questioning.

On the flipside, extended periods of singleness can make the adjustment back into the dating world rough. People get set in their ways, which may make dating down the road a more difficult ordeal. Suddenly having to share your life with another can feel unnatural, even draining in the beginning.

The worst part about being in a continuous casual dating phase is being used to under-committed relationships. Getting used to a lifestyle where relationships are based on convenience and superficiality can be fun, but costly to one’s capacity to develop deep, sustainable relationships down the road. Which brings us to our point…

The Relationship Route

Beyond the obvious factors of companionship & intimacy, relationships in our twenty-somethings are largely responsible for the outcomes in marriage, for better or worse. On the positive side, relationships can teach us real commitment and to take a long-term approach to life.

A friend said that those who commit to you in your twenties – when you don’t have it made and still establishing yourself – should sit high on your priority list. The ones who stick with you despite your struggles understand you on a different level than those who’ve only known you as successful and are attracted to you based on your success. Indeed, as time ticks closer to the dreaded age 30, people may start focusing on some criteria more than others: financial & physical health, more so than personality, creativity and ambition.

My 2 cents?

It’s not easy to be young, mobile and experimental and balance that out with a committed relationship. People can change. A job opportunity can place you in a different part of a country. But if you think you’ve found someone special, and you’ve thought through what you want – then it may be time to throw your hat in the ring and get committed.

Awkward Goodbyes

I rotate assignments every 4 months. Different cubicle. Different coworkers. For the most part, different type of work. But the goodbyes that come at the end of each rotation are always the same: awkward.

Today was the last day of my current rotation. So those in my work group kindly stopped by, said a few words, and that was that. The funniest thing that happens is when people know you’re leaving and you’d have these halfway conversations with them throughout the week. They “save up” what they want to say, in a sense, because it’s awkward to say goodbye and end up seeing that very same person and have a normal conversation again.

It’d be weird if they were giving me a final farewell and I ended the conversation asking how their kids’ baseball games are going. In some sense, I can be a very nonlinear (some call it ADD) guy when it comes to conversation. I’ll jump from point A to D and back to C.

And invariably, this closure ends with a hopeful projection into the future. “Well, I know we’ll be in contact. Let me know if you need anything or have any questions.” These types of farewells smooth out awkwardness, and sometimes feel more like they’re for those staying rather than those leaving.

This time, I learned – When it comes to goodbyes, people are linear. They want an end, a closure. And I’m okay with that, even though I’m returning the very next damn day to pick up my stapler.

I tend to like the parting words that erred on the side of too casual than too serious.

“Alright cool man, I’ll catch you later.” That’s what my immediate boss  said. I liked that.