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.

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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

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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 to Move Beyond Self Comparison – Part 2

IN SCHOOL, this question annoyed me the most:


“What’d you get on your test?”

I started labeling repeat offenders as TSNs – Test Score Naggers. Even early on in grade school, I avoided  TSNs because something didn’t sit well with how adamant they were in knowing my score. When I did better than they, they would seemingly look defeated. When they did better than me, they would seemingly feel validated. I never understood – WHAT DOES MY TEST SCORE HAVE ANYTHING TO DO WITH YOURS? WHY DOES MY # AFFECT HOW YOU FEEL?

Turns out, this didn’t stop at school. Even in the professional world, you may meet people whose perogative is to find out how much you’re making within the first minute of meeting.

My answer nowadays is usually “enough.”

Whether I’m doing well for myself or not, I don’t want to promote what I believe to be the wrong measuring stick – one that doesn’t align with my personal definition of success. As I wrote in How to Move Beyond Self Comparison – Part 1, having a weak sense of self, manifested through ignoring my own passions, made me a prime candidate for self-comparison.

But even when I found my direction, the self-comparison didn’t end. In my new career (which I enjoy) I am still feel like a beginner. The opportunities for self-comparison still abound.

Like many of the worthwhile challenges in life, the goal is not to get rid of bad emotions altogether – because it’s impossible. Just like how one can’t get rid of stress, one can learn to manage stress. I don’t believe self-comparison can be “cured,” but it sure can be managed.

Thanks to reader Ivy K.

In this second installment, we explore 3 strategies – including useful mental models – to manage self-comparison.

Strategy 1: Choose Your Type of Self-Comparison

Ivy shared that thoughts of self-comparison lead her down two paths: whether it’s something that matters to her, or something that doesn’t actually matter that much to her. It sounds simple, but this clear distinction not only helps avoid pointless stress, but also gives you the power to choose what type of self-comparison is worth it.

Self-Comparison Type A: Something you care about

You might compare yourself to someone who’s doing something that MATTERS to you. This strikes a chord. It can be your job, your craft, a personal skill you want to develop. If you care about it, self-comparison usually means you want to improve yourself in that way.

In How We Judge Others Is How We Judge Ourselves, Mark Manson said that the way you measure yourself is how you will measure others, and how you will assume others measure you. Using this knowledge, you can make self-comparison work for you. Pay attention to what you judge others by – be it looks, career success, healthy relationships – because that in turn identifies what matters to you. I often find myself subconsciously judging others by how entrepreneurial they are, or by the quality of their romantic relationships. Turns out, those are things that I value a lot.

Ivy’s example, when she sees someone who lives a healthy lifestyle: “That person eats really healthy… I should try to be more like that person because that is a trait I want to have, and I think I would be better off if I did.”

This moves us from self comparison -> self improvement, from jealousy -> inspiration. Instead of feeling like the lesser, recognize moments of self-comparison as opportunity – you just spotted someone who might be in your tribe. They might help you realize your goals and dreams. Message them. Meet up with them. Surround yourself with the type of people who are experiencing the type of success you want.

So self-comparison isn’t all bad. Let it inform you what you care about, and let it give you an opportunity to connect with like-minded people.

Self-Comparison Type B: Something you don’t care about

This is what we all want to stay away from. Why do we stress over that LinkedIn acquaintances’ new promotion even if it’s in a completely different field? Or feel “behind” watching friends get married, when marriage is the last of your priorities right now? We stress about things that don’t even align with our personal goals and values.


The best strategy is to actively think “I’m happy for them.” It might feel disingenuous at first. But that’s with all new things. Over time, being happy for other people gives you a twofold bonus: one, you are a more positive and happy person, which will definitely make you more enjoyable at parties. Two – saying “I’m happy for them,” helps you recognize that others are doing things that make them happy, which is a different definition than what makes you happy.

I’ll quote Ivy once again: good self-comparison looks something like “Wow, you completed an ironman triathlon? That’s way more intense than anything I’ve ever done, but I don’t think I will ever be interested in going that. That’s just not me; I would rather sit on the couch and watch the entire Breaking Bad series.”

Strategy 2: Realize How Self-Comparison is Oddly Insulting

“Facebook? Yeah I totally thought of that five year’s ago…”

Everyone has that one friend or crazy uncle who claims that they thought of million-dollar products before they got released, and somehow feel robbed of their ideas.

OK, OK…that crazy friend was me. Until I realized I was insulting the work of others through superficial self-comparison. It makes absolutely no sense that someone else’s success should take away from my own, and vice versa. When you are successful, do you see that as you taking success from your friends? Hell no, that’s ridiculous. So why do the same do yourself?  For the wantrepreneurs out there, I realized that it was an insult to think that I deserve success by coming up with an idea, as opposed to someone who has poured their souls into doing something great.

Looking at things this way made me realize that over 95% of the time, the people I compared myself to completely deserve the success they’ve made.

An interviewer asked Dustin Moskovitz what it felt like to be part of Facebook’s “overnight success.” His answer: “If by ‘overnight success’ you mean staying up and coding all night, every night for six years straight, then it felt really tiring and stressful.”

All the writers and artists out there might resonate with this:


Self-comparison often afflicts us because we compare ourselves to the wrong things. Comparing your first draft to someone’s masterpiece doesn’t make sense. Comparing your first practice GMAT score to your friend’s 750 doesn’t make sense. What makes sense is to focus on what goes in the background of the success you want – which is usually tons of hard work and discipline.

Strategy 3: A Weird Thought Experiment

IMAGINE the terrible scenario: the lives of everyone you know starts deteriorating. The rich friends you were once jealous of go broke. The annoying, happily married couple end up in a nasty divorce. Shit is hitting the fan – turns out the lives of those you were measuring yourself against are suddenly going downhill.

Does that make you happy?

The answer, if you’re like most sane people, should be a resounding NO. The value of your friends doing well is intrinsically worth more to you than their lives sucking. Even if some of us are assholes, most of us want good things for each other.

The best way to manage self-comparison, in turn, is to realize how fortunate you are to be around people aren’t just doing well…but WHO ARE DOING BETTER THAN YOU. The better the people around you, the better you’ll get.

If I’m the smartest one in the room, I made a huge mistake.

Ever heard of the Rule of 5 Friends? It states that your life will most likely end up like the 5 people you spend the most time with. If the 5 people closest to you are miserable, it won’t be a surprise that you might be miserable. If your 5 closest friends are millionaires (not a guarantee you’ll be rich), you’re probably better off than hanging out with 5 broke individuals.


So imagine this. A community around you in which people are striving to become better every day. The friend applying for her MBA to make a career change. The friend trying to be a great husband. Your coworkers who are ambitiously trying to make it big with their own startups. It’s in your best interest that they all succeed. One obvious reason is that they can better help you if you pursue similar ventures. I completely subscribe to the belief that the value of your network translates to the value of your net worth.

It makes me REALLY excited for my friends to go out there and consistently kick ass. And I want to kick ass for them, because I want to be better equipped to help them if they ever need it.


Let’s close with the simplest, most powerful strategy of all to deal with self-comparison: be grateful for what you already have in life.

If you’re reading this, you are probably privileged enough to have time for personal development. The self help industry attracts those who are relatively high up in Maslow’s hierarchy, such that few are struggling to find reliable shelter, food and work. 

While there is an endless # of opportunities to compare ourselves to others and feel shitty about it, there’s an equally long list of things we can appreciate in our daily lives. Whether it’s being in decent health or having an education, a lot of our stress from self-comparison seemingly melts away when we step back and appreciate what we have. We might not have it all, but we can take joy in what we have.

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How to Move Beyond Self Comparison, Part 1


In this first installment, I talk about how my (initially) unexciting career path leads to a huge realization, and shift in thinking that helped me move beyond self comparison. I’m still writing Part 2, which is about specific strategies to deal with self comparison.

THERE WERE many chances growing up to feel like the black sheep of my family. My late father was an engineer, my mother is an accountant, and my two sisters are both doctors.

So… what’s your major?

I entered UC San Diego undeclared. I didn’t know what the hell I wanted to do. But I knew to pick something between science (I had no brain for it) and English (not mom-approved). So in my freshman year, I started my first quarter out as Economics, my second quarter as Urban Planning, and my third quarter as Communications. Come end of freshmen year, I returned to Economics.

What do you want to do with your life?

My career path was just as meandering. I thought I wanted to be a Certified Financial Planner and manage people’s money. That phase quickly passed and I wanted to be a management consultant (what business student doesn’t?)

Then I went on a life-changing trip to Haiti. It was part of a medical missionary, so I gave dental anesthesia and pulled out teeth. I was inspired to be a dentist [MOM-APPROVED]. I It was meaningful work, but after 3 weeks of returning from Haiti, the thought of back-breaking days telling patient’s “say ahhh” didn’t exactly stir my loins.

Then I started an accounting society with some friends and decided to pursue the safe and approved route of auditing [MOM-APPROVED]. Come hiring season, I was faced with 2 options: Big 4 or a rotational program at a huge corporation? I chose the latter, because even then I wasn’t exactly sure what I wanted to do – and this opportunity would give me 6 opportunities to test out different areas of business.

Finally, fast forward and now I’m a User Experience Designer [MOM-WTF IS THAT?]. After two dozen years of living, I found my direction. I knew I wanted to create, to write, and to design.
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All throughout that time, I was exploring my interests…but damn, a lot of that time was spent miserably comparing myself to people who seemed to have it all figured out. I would be pulled in other directions like a kite in the wind. Talked to someone who was a successful internet marketer? Man, what am I doing with my life, I need to do that instead! Then talk to someone who learned how to program and snagged a Silicon Valley job? Shit, I need to learn how to program too and get my act together. Friend is making tons of money in sales and the work is easy? I should just do sales, right?

You can see how productive that way of thinking was.


Jealousy and self-comparison fall within the same realm, and you may even argue it’s the same thing. But something is lost in the connotation. Jealousy often conjures up thoughts of a crazy, tire-slashing ex, or a possessive friend who doesn’t like it when you get chummy with new friends.

But you take a second look at jealousy and realize what it really is – a manifestation of insecurity. Insecurity means not having a secure sense of self. It implies a lack of self-investment, which means being prone to the undulating waves of external life events; someone is more attractive than we are, someone is making more money, someone is more… groovy.

In relation to my zigzagging career path, I learned how to stop comparing myself to others only after realizing that I, myself, was insecure. I was ignoring myself. I wasn’t listening to my own wants, needs and passions. Which brings me to this truth:

More often than not, self comparison has less to do with jealousy, than than the dissatisfaction of living a life untrue to yourself.

Once you have even the vaguest idea of a direction you want to pursue, you must chase it down. Only if you keep pursuing what makes you feel alive, will you feel like you’re your own person. I mean, shit, I was blogging about personal development since I was 18. It never occured to me that it was something really enjoyable to me that I needed to nurture and develop. It took several years for me to wake up and treat it like the earnest hobby it is, and give it love on a weekly basis.

I reference this Huffington Post article a lot, but the #1 biggest regret of the dying is this:

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

It’s tough to know what you want. It’s tough to define your personal version of success. It took me a long time to decide that I need to be the CEO of my own life, and not follow the latest fad, trend or “22 things I must do as a 20-something” article. It doesn’t make any sense whatsoever to want someone else’s version of success, just for the sake of achieving that exterior validation of success.

Always be a first rate version of yourself and not a second rate version of someone else

Or, as I’d to say, if you don’t define your own version of success, someone else will do it for you.

Prime example: parents. My younger self used to always let my mother’s suggestions govern what I should do career-wise. To her, job security was tantamount,  so she struggled to understand why I left a stable job to pursue a completely different career.

It took time to realize that my mother comes from a different generation with a different type of thinking with different values. A lot of those values are good and make sense – but they don’t necessarily fit my interests nor what I define my personal success as.

If you feel like your parents are still trying to define success for you, the most important thing you need to know is that they all just want you to be happy and successful. As long as you do the work it takes to discover your direction, pursue it, and tell your folks that’s what makes you happy – they don’t want their kid to be unhappy, right? –  that should be enough. If it’s not enough, the responsibility is on their end to understand that success has a different meaning between you and them.

To this day, I’m still defining my own version of success. And now writing this, it strikes me that as with all worthwhile things – finding love, getting good at something – defining personal success will probably be a never-ending, lifelong journey. All that matters is that we keep walking.


When I was 18, I thought I’d be a millionaire in my twenties, cruisin’ down the street with a nice BMW I bought for myself. Of course that would still be nice to have, but my priorities have changed. I still care about money, but now I want to spend it on experiences, more so than material goods.  If you look at my bills, a disproportionate amount is spent on food, events and salsa classes. If I could, I’d get rid of my car.

What you thought you wanted at 25 will change when you’re 30. And what you prioritize in your 30s will be different when you’re 40, and so on.

So go ahead. Find the beat of your drum. Know yourself well. Literally take care of yourself. If you take care of your passions, they will take care of you.

To establish a sense of who you are and what you want to do, is to put the specter of self comparison back in its grave.

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I’m not done writing about self-comparison yet…so subscribe below to hear about How to Move Beyond Self-Comparison: Part II.