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.
_ _ _

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.

The Unconventional Guide to Getting Over Breakups


IT’S UNAVOIDABLE. You will have your heart broken in your lifetime, one way or another. It’s an inescapable part of human existence, but that doesn’t mean it has to be all bad. In fact, I’m confident that reading this article will help you process your emotions in a healthy way, and change the way you think about breakups forever.

Me? I’ve been through 4 1/2 breakups:


*Note: #3 deserves an entire post unto itself. Maybe someday, when I’m brave enough…

As you can see, I’ve been on the receiving end of breakups the majority of the time. Each hurt in its own way, but I came away from each experience a wiser, more grateful person.

What you’ll read next is years of breakup knowledge distilled to their finest essence, and I hope what I’ve learned will serve you well – especially if you’re on the receiving end. Disclaimer: there are obviously some demographics that my advice isn’t the best fit for, such as including divorced couples with kids.


The first thing I’m going to tell you is a bit unconventional. If the breakup just happened… You should be sad. Go head and cry, feel lonely and in general feel like shit. Wait, is this real advice?

Yes. Because it’s what goddamn normal humans do. This is healthy. It doesn’t mean that you should drown yourself in tubs of ice cream and accept depression as a new way of life. The important part is that breakups – just like relationships – are a process. And the beginning of that process is ESPECIALLY shitty. There are no shortcuts around it.

The only real shortcut is to embrace feeling shitty. Because what’s worse than feeling shitty is denying your feelings. Ignoring your feelings is a dangerous thing to do, because it hinders growth and self-awareness (we’ll explore this shortly).

So go ahead. Wallow. Bitch, moan and whine to your friends (you did the same for them, right?) Go run a mile in the rain. Listen to all the sad songs because they’re singing JUST ABOUT YOU. What you might not realize is that it’s actually helping you process your feelings. Invest the time to do this at the beginning of the breakup, because you can’t stay in this suspended reality of sadness forever.

Don’t cut off contact. Amputate it.

If there’s ONE TRUTH to getting over a breakup, it’s to completely and ruthlessly cut off contact. If it helps, first tell the ex what you intend to do and it’s no hard feelings (or maybe it is), but you need to cut off all contact to properly heal. In the meantime, you’ll also:

a. Delete their number and all texts associated with number.
b. Unfriend them on Facebook, Instagram, Snapchat…all social media
c. Don’t see each other. Don’t go to each others’ houses or show up to the same parties. If you can, just avoid being in the same fuckin’ space.

“Don’t talk to your ex,” seems like obvious advice. But no one – including myself – follows that advice because they’re missing the “why.” Why is cutting off contact with the ex such a good idea? A better way to think of it might be the opposite: why is staying in contact with my ex a bad idea?

It’s because of a thing called Hope. The sick kind of hope that doesn’t make you feel good, but makes spin your mental wheels giving you the POSSIBILITY that maaaybe things will work out and maaaybe you guys can get together again. Hope can be the most crushing, damaging thing, because we put our egos and self-worth completely on the line, in hopes for a second chance.


Comfort is Hope’s sidekick. Because of comfort, you end up inviting your ex over for an innocent dinner “as friends,” then somehow end up in the bedroom, clothes off, it feels so right…and end up in an even more confusing and unhealthy place than before. That’s the danger of comfort, because it leads to more hope.

Let’s get it straight: breakups are not supposed to be comfortable. Prepare to be very, very fuckin’ uncomfortable and hating your life for at least a few weeks. Just consider it an emotional bootcamp.

If it’s anything to cause damage to feelings of self-worth, it’s the shitty brothers Hope and Comfort. By completely removing contact from your ex, you leave little room for more unnecessary agony.

You are not responsible for your ex.

After a breakup, neither party is emotionally responsible for each other. This is hard because the gravity of comfort gets in the way. There’s just too many goddamn convenient excuses to “fall back” into acting like a boyfriend/girlfriend after a breakup because you feel “bad” for them:

  • He needs me around because his family’s going through tough times…
  • But I promised her I’d take her on that trip…
  • We have too many mutual friends, it’ll be awkward…

All of the above seem reasonable enough. Until you do this thought experiment (let’s say boy breaks up with girl):

Boy: Hey… just wanted to check if you’re ok.
Girl: Yeah I’m fine, thanks…
Boy: Umm..ok. Let me know if you need anything.

The above has only achieved the following: remind the heartbroken girl of the boy’s existence. She was having an okay day and now he just reminded her of their shitty breakup, and the fact that she got dumped.

So think about it…if you broke up with someone, and have the urge to contact your ex, is it really for them, or is it for you?

I’ll go ahead and answer that – it’s for you. It’s you who feels bad for dumping them, but it does nothing for them. They feel worse. You just reminded them that you exist. I was such a selfish mofo before. Don’t be like me.

You’re no longer responsible for each other, so don’t feel guilty, and don’t make the other person feel guilty. Whatever has happened is in the past, and now you are two single people trying to live in the present.

Part 2: Reflection, or, How to Not Waste Your Breakup

For me, breakups were always something like a wake up call. One moment you’re in the dream of a relationship, the next moment you wake up in bed alone. This is a confusing time and some questions might run through your brain, as they have mine:

Was I not good enough?
Maybe I shouldn’t have told her _____
How long will I be alone for?
I wonder if she’s going to end up dating that guy she keeps talking about
Maybe if I do this one thing, that’ll change her mind?
Maybe I’ll try online dating [link]

If it’s one thing that breakups for us, it’s to make us look hard at ourselves in the mirror.

Invariably, self-defeating thoughts creep into the post-breakup psyche. But I think this period of pensiveness can also lead to honest reflection…and potentially the most emotional growth of your life.

Want to maximize your self-reflection time? Spill your guts out in writing.

Write everything. Write how you feel. Write why you think your relationship ended. Write your side of the story, then write your ex’s side of the story. If you are lucky and ridiculous enough like me, ask for a letter from your ex.

The exercise above will serve you in two ways. The first is catharsis. To sort out feelings, clarify thoughts and help you process the breakup. The second is to learn, and to hopefully incorporate lessons learned into future relationships.

Look, relationships are one of the most important things in life but it’s never taught in school. So take this time to do some real homework. Breakups are actually an amazing opportunity to learn about yourself and get life figured out.

So don’t waste your breakup. Learn from it.


A great way to waste your breakup is to jump into another relationship. Doing so is like having an open wound and repeatedly ripping off the scabs, preventing you from healing properly.

Special note: If you’re an attractive person, especially an attractive girl, it’s very likely that others will pick up on that new single scent and hunt you down.

Be friendly but curt to friends who are pursuing the new single you. Don’t try to win the breakup by racing to be the first person to start dating again. That’s playing a losing game. You don’t want to jump from one trap into another. Resist the breakup-validation cycle.

And trust me, the allure of rebounds will be great. Rebounds are a great way to deny your own feelings and waste someone else’s time.Not to say that rebounds can’t turn into healthy relationships. There are just too many gray areas to cover in one article.

My recommendation is to, at the very least let a season pass. That’ll be 3 months. But what will you do in these lonely few months?

I’m glad you asked.

Part 3: Moving On

Inspiration strikes at the oddest moments, so I’ll share with you a scene from World War Z. Brad Pitt’s character finds temporary safety in the apartment of a Latino family. Knowing that the apartment will soon be overridden with zombies, Brad Pitt tries to move everyone to the rooftop, in hopes of catching a helicopter. The Latino family won’t leave their apartment, fearing that they’ll get eaten alive upon stepping outside. To which Brad Pitt says: “Movimiento es vida.”


Movement is life. Those three words pack so much truth. At a molecular level, if you don’t move, you are literally dead. Your heart needs to beat. Electrical impulses need to be sent. In the same fashion, you literally need to move to get on with your life.

So pick up a new hobby. Sign up for a class. Go get that beer after work with coworkers. Do a zombie run. Build a social community around you, however small. The common denominator is that you are doing SOMETHING.

Don’t like where you are? Move. You are not a tree.

In the wake of my last breakup, moving unintentionally and intentionally did wonders for my personal happiness. I moved to LA and shortened my daily commute to 30 minutes a day (round trip, BOOYA). I started practicing Spanish and found a weekly group to converse with. I signed up for salsa classes and ended up really enjoying them. Every couple of weeks, new students pop up in class. I make an extra effort to be friendly to them. Who knows, maybe they’re trying to move on from something too.

Remember when Forrest Gump just takes off running across America non-stop for three years? Crazy mofo. I watched that movie so long ago that I forgot why, but the power of Google makes it known: no, it wasn’t because Forrest’s mother died. It’s because his love Jenny just took off one day. It was the worst kind of breakup, the disappearing kind. So Forrest decided to move. He ran and ran and ran and literally started a national movement.

You don’t have to run across the country, but you need to start moving.

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Moving on mentally.

Let me make it clear right now – I don’t like the “just think positive and the world will come to you” advice as advertised in gimmicks like “The Secret.” I actually regret telling you about it and giving that facile work even more attention. But positive thinking can have a very constructive role in helping you move on mentally.

Imagine the difference between how two individuals can handle a breakup: one thinks of the event as 100% negative / 0% positive. He has a victim mentality and begins to make unsavory assumptions about every other female in the world. Without coincidence, this mentality only serves to distance others from him.

The same breakup can happen to another individual, who manages to see the silver lining. He’s not giddy after being dumped. But he sees this as an opportunity to reflect, to grow, and improve himself. Even if he can eek out a 51% positive / 49% negative experience ratio from this breakup, that’s a win. Ultimately, it’s up to you to tweak that ratio yourself.

Breakups can seen as a totally bad thing. Or you can see it as a good learning experience. There’s literally NO upside to the former and only upside to the latter. Positive thinking is a choice and responsibility. Some people say that perception is reality. I tend to agree that life really is in how you frame events, You’re already winning if you can manage to focus on the good.

It’s not 3014, so the memory-wiping technology of Eternal Sunshine of the Spotless Mind is not available yet. But guess what – you can make new memories. According to the primacy effect, human memory (obviously) discriminates favorably towards newer, more recent experiences. Leverage this and allow new experiences to occupy space in your mind. We can’t delete memories, but we can choose to have new ones that surely become just as, if not important than our old ones. If that’s not the case, then starting a new relationship will be impossible.


*(Un)Fortunately, we can’t erase our memories. But we can make new ones.

So with that, allow me to impart with you what I’ve found in the past several years to be the healthiest, most helpful frame of thinking one can adopt after heartbreak:

You were part of her process, and she was part of yours.

Experiencing a relationship means that you and your ex were part of each other’s process in finding love, compatibility, shared values…all the intangibles that make life great. For some couples, that process comes to an end when at least one half of the couple has learned that the relationship is not what he/she wants.

Two people who hit it off when they were 15 and end up married for 30 years are experiencing their own process. That doesn’t mean it needs to be yours.

It’s like graduating from college and expecting to land your dream job that you’ll be passionate about for the rest of your life. (Again, it’s possible, just not probable). The reality looks more like this: you start in an okay job but you know it’s not where you want to go. But it gives you enough experience and skills to take on the next job. And then the next job. You keep learning. You’re pleasantly surprised that some of the skills you learned in old jobs become useful, and uniquely advantageous in your new job.

It’s not a perfect parallel, but just as different jobs can be stepping stones in your career, each relationship helps you grow and learn to hopefully make the next relationship better.

I’ll end with this scene from To Those Nights (WongFu video). It’s a bit cheesy but the conversation, which I’ve transcribed below, is gold:

Boy: I wish we never ended the way we did, I just wanted you to know that
Girl: You’re learning about yourself, and who you ultimately want as your companion. I was part of that process, and you were part of mine. You don’t need to feel sorry anymore.
Boy: I’d be better now if I had another chance
Girl: I know you would. But you’d be better for someone new. Don’t waste all of the pain we’ve already endured on trying to mend the past. Use it to learn, and grow for the future. Even if I’m not part of it.


1. Suffer Fully
2. Amputate Contact. Eliminate Unnecessary Hope.
3. Reflect. Write. Capture your lessons learned – don’t waste your breakup.
4. Start Moving, Physically and Mentally.
5. Know that It’s All Part of the Process. Move On.

What are your experiences and lessons learned from heartbreak? Comment below or send a message to

Be well.

Shit. I Was a Rebound.


This letter should thoroughly describe why we couldn’t work. You wanted raw honesty, here it is: you were my rebound.

I must have read that line a hundred times.

It was a turbulent Summer 2013. My ex at the time just broke up with me. After doing the most ridiculous thing I did to any ex, I finally received the breakup letter that explained everything. I was her rebound.

In retrospect the signs and my feelings all direct towards that epiphany. You were right, I may have denied my feelings for [my ex] and believed that they were nothing more than friendly sentiments.

_ _ _

EVEN IN THE BEGINNING, I had clear knowledge that she wasn’t over her ex. The chips were heavily stacked against my favor: they were together for four of her formative years, high school through college. He was considered part of her family, and vice versa. She relied heavily on him for everything from mental therapy to car maintenance.

Then I came into the picture. I saw all the red flags. I sought the counsel of wise friends. To which I said: “This is trouble. I know what I’m getting into. But I’m going to do it anyway.” Delivered with a smirk that only a twenty-something with naive confidence and plenty of runway can have.

At the end of the relationship, there was a weird solace in knowing that I chose to pursue the relationship, regardless of how well it was set up to fail. Sure, I had plenty of hope. But it was my responsibility. She was an experience I wanted to experience and I experienced it.

That doesn’t mean it didn’t hurt.

I wanted to be over [my ex]; I wanted to move on. I didn’t know how, I also didn’t know that I hadn’t yet. When I was finally over [my ex], my feelings for you seemed to have changed as well.”

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There’s this movie called About Love, which I watched well before the occurrence of this relationship. In one of the vignettes, a boy develops unrequited interest in a girl. But the girl asked the man for a favor: a ride to her ex-boyfriend’s place to get some closure. She comes back from the conversation, seemingly down.

It’s pouring rain as the boy gives the girl a ride back. They enter a long tunnel, giving the pair brief solace from the rain. In this moment, the boy realizes that he too was a tunnel for the girl. The rain represented the emotional turmoil she was processing, and the tunnel was a temporary haven that she would surely have to leave.

I think I was a tunnel too. And I have no regrets. That relationship taught me a ridiculous amount about what I want, don’t want, and importance difference between chemistry and compatibility (hint: it helps to have both). For those who have been following the Breakup Series, I’ve been working towards several unconventional guides, one of them including The Unconventional Guide to Breakups. Subscribe below to be the first to hear about it.

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Thank you so much for writing the letter, I know it wasn’t easy.

I’ll try my hardest to learn from my mistakes and hope not to repeat them. I regret making you feel the negative things you felt, but I don’t regret the times we had together, good and bad… [edit] I wish you infinite happiness and joy. Perhaps our paths will cross again.




If You Think Being Single is a Problem, Think Again


Were you feeling lonely on Valentine’s? Maybe you saw your coworkers receive flowers at the office. Or non-single friends kept asking you what plans you had for February 14th. Or, most likely, you saw your Facebook blow up with Valentines content, pictures of couples each other, etc…

I didn’t have a Valentine’s this year. To my surprise, I didn’t mind. I was happy for my friends who were in solid relationships and had plans for their special Friday. I didn’t feel bitter, alone, nor even annoyed at the surge pricing of flowers and chocolates that comes with this particular holiday. Maybe part of it was just growing up. But I did feel anxious about something else.

Perhaps this thought will hit you like a ton of bricks the way it hit me:

This has nothing to do with being single. This has everything to do with finding the right person.

We get preoccupied with the label of being single. In our hyper-networked culture, single is associated with loneliness. Not a twenty-something will dare eat or watch a movie alone in public. To be seen as alone can be viewed as inferior, hearkening back to primordial days when being singled out was literally a matter of life and death.

But it’s 2014! The age of Amazon, disposable condoms and handheld devices that can hail the equivalent power of 150 horses to give you a ride 2 miles away. Being single is not really a problem in this modern age.

Being single is a state of being. It means that you’re not involved in a romantic relationship with someone else. At face value, there is nothing wrong with this. The real issue single people face is the frustration of finding the right person and establishing mutual attraction. It requires hard work – sometimes even heartbreak.

Taking the time to get to know someone isn’t easy. Building an intimate connection isn’t easy. Finding both compatibility AND chemistry isn’t easy.

If dating was easy, thousands of dating sites and tens of millions of dollars wouldn’t be expended to solve the ancient problem of building a real connection between humans.

At first I was shocked that there were so many attractive girls on dating sites. My first thoughts were “look at them…how could they ALL be single?” It’s obvious how short-sighted that notion was: attraction requires more than just looks.

Many of the gorgeous women online can have free dinners every day of the week – and some do – yet they still haven’t found the right guy. They didn’t find the right fit, that mutual attraction, or a number of other possible reasons.

CONVERSELY, if you go out enough, you’ll find that there are lots of people who want to date you…but you want nothing to do with them. In this sense, being single is a choice.

This hypothetical may once and for all cure any notions that being single is the problem:

What if, in some fucked-up alternate universe, you HAD to be with someone? In this universe you would be stuck with whoever is assigned to you and that’s it. (I guess some people might call that arranged marriage.)

Now that we’ve established that being single is a choice, not a problem, we can begin to explore the core underlying issues:
how do I figure out what I want in a relationship? What do I need to work on to become a more attractive person? What can I do to meet that special someone? 

These are all questions I’m working to answer…to be among the first to get notified of pending works like Slow Dating, an Unconventional Guide to Finding What You Want and more, subscribe with your email below.