The Dealmaker/Dealbreaker List To Determine Compatibility

Image from andilicious on Flickr

I was talking with my friends recently about what what it takes for a marriage to succeed. As the conversation went on, it become clear that the same principles that make a marriage work are what makes any healthy relationship work. Given that your ideal life partner should also be a best friend, the reasons you chose them should be the same reasons you choose your friends, your housemates, and anybody else you choose to spend time with.

We all have friends that we could never live with, and housemates that we would never even be interested in marrying, even if we get along with them just fine. In each of these relationships, the involved parties require certain criteria to be met, but what you look for in a friend obviously isn’t exactly what you look for in a wife.

Speaking personally, I choose my friends based of our personal chemistry and the interests we share. Then we can spend time together indulging in said interests, to the benefit of all. True, sometimes the interest supersedes the chemistry (for instance, I’ve had sports teammates who I wouldn’t ever see outside of practice, and nerdy video game partners who I only ever saw while next to a screen), but an ideal friend would have just as much fun doing both with me, because they’re things we’d do regardless.

That said, I’m not a total mercenary with my activity partners. Hanging out with someone just to fill out a sports team is lame, and if our chemistry is completely at odds then both are better off avoiding each other. Just as with marriage or cohabitation, friendships require certain fundamental agreements.

I call these Dealmakers and Dealbreakers – a list of must-haves and must-not-haves for any relationship. The list becomes more stringent as you move up the ladder of commitment: I’ll be more picky choosing my wife than a girlfriend, than a roommate, than a drinking partner. But each relationship has its own prerequisites, built on top of the criteria below it. Your list will differ from mine, but as an example, here’s a slipshod version of my own list (I haven’t ever written it down, but it doesn’t require much thought):


  • Dealmakers: Jovial, curious, and playful
  • Dealbreakers: Emotionally unstable, untrustworthy, deceptive.
  • Other: Outside of this list, we can differ all over the board (all the better, for diversity and new experiences), but if they don’t fit these rules we’re unlikely to enjoy each others company.

Living Partners

  • Dealmakers: Okay with my living space being messy, don’t mind me hosting friends for dinner or drinks
  • Dealbreakers: Steal my possessions, make me feel unsafe in my own house.
  • Other: I don’t care if the sink is always full – as long as I can find a dish that’s moot. Yet some housemates require their kitchens to be fastidiously clean, in which case I can wash my stuff along with the best of them. Since it’s not on my dealbreaker/dealmaker list, I can be flexible around the lists of my partners.

Spouse (under construction)

  • Dealmakers: Spunky, confident, ambitious (if I subscribe to GoodGuySwag’s Wife List, there’s a lot more)
  • Dealbreakers: Needy, acts like a princess.
  • Other: This is based off of the romantic relationships I’ve had so far – they’ve all ended because one of us eventually found a dealbreaker in the other. As frustrating as it was at the time, now they’re great examples that have taught each of us what we will and will not put up with. (Related: WaitButWhy on Picking a Life Partner)

Every friend, housemate, and significant other you have refines your Dealmaker/Dealbreaker list. It’s an iterative process, culminating in a perfectly accurate list that lets you impeccably sort out the makers from the breaker.

Everything not on either participants’ list is moot. They’re not relevant to your compatibility – just extras that spice up the game. They may be drastic differences of opinion or lifestyle, but as long as they’re not on either person’s list, you’re good. I’ve had great friends with completely disparate cultures, religions, beliefs, and lifestyle choices from my own, who’ve all taught me great stuff. Since we didn’t differ on any dealbreakers, the differences only served to make the relationship more interesting. We learned from each other.

If you don’t know what your list entails, (hopefully you do by now) then you run the risk of the relationships falling apart due to something the other person does that you can’t stand, or you ending it because they lack something you’ve decided you need.

What’s on your Dealmaker/Dealbreaker list?

PS: My mother notes that as relationship goes on, a new aspect comes into play – shared history. She’s been with Dad for decades, and raised kids with him, which becomes a powerful force for staying together as the shared memories multiply. She may have found new annoyances in his manner with age (I’ve seen a few of them myself), but even if they border on dealbreaker territory, there’s the entire life of shared history to keep things going. They know each other too well.

That doesn’t come into play at the start of a new relationship, but it certainly does with time, and is something to consider alongside the DM/DB list. Is this someone I want to have shared memories with? It’s the past tense version of the decision you’re about to make – is this someone who I want to spend time with? If they have the makers without the breakers, I’ll bet it is.

Tim Ferriss’s NOBNOM Challenge – One Month Later

I recently partook in Tim Ferriss’s NOBNOM challenge for the month of August – no booze or masturbation allowed.  The challenge intrigued me because these are two activities done reflexively without thinking, yet can become powerful negative addictions if indulged wantonly. Just like true alcoholics, everyone says “I can stop whenever, but I don’t want to.” Thus NOBNOM was a perfect chance for me to test exactly that over the course of a month.

And so I signed up to track my progress with Lift, a habit tracking app. I quickly found that while I could successfully avoid both proclivities every day, I was not as good as logging that fact with Lift every  day, despite it’s incessant (and annoying) push remainders to do so. (Indeed the whole challenge was a clever onboarding hack for Lift, which Tim advises. See the Tim Ferriss effect.)

Even though checking in was one big easy button, and even though you’d get ‘Props’ from other users on your accomplishments – I just couldn’t fit the act into my daily routine.  I didn’t care what strangers thought about my achievement, I just wanted to do it for myself. This need to unobtrusively track offline activities is the problem all lifelogging apps face –  since not all of us are meticulous personal historians like Nicholas Feltron.

Anyway, Lift aside, I found that the simple knowledge of the challenge was enough to quell most urges. Normally I have no reason not to indulge, and thus do so without much thought, but for this month there was a secondary ‘No, you can’t, it’s NOBNOM’. And that was that. The simple presence of the challenge and my public participation in it was enough to hold me off, even though nobody would know if I snuck in one or two breaches. Here’s some thoughts on each aspect:


There were a few close calls here, mostly within that half hour before bed when you can’t fall asleep and have nothing to distract yourself with. Usually I would try to channel it to nonfiction reading for personal growth and to make me more tired. But it was very tempting to give up in order to get short term payoff (fleeting pleasure and sleep) at the cost of long term betterment (self discipline and time).

I won’t detail the effects on my libido here since this is a professional blog, (the web claims there’s all sort of health benefits like higher testosterone, higher ambition, and so forth) but I did feel like there were upwards effects in stamina and confidence. It could have been the placebo effect, though.


The drinking aspect was surprisingly  easy. I had been thinking about quitting alcohol after reading stories like that of James Swanwick and Sam Parr, who cite many positive changes, but again, there was no external reason for me to do so. Now there was NOBNOM, and the presence of a scapegoat I could blame as an excuse to my friends proved to be enough. I only drink socially anyway, and so the whole month boiled down to only a few social moments in bars with friends where I’d have to stand strong again the social pressure. My friends respected it, I was still out with them, and it really wasn’t as big of a deal as past me had made it out to be. As long as you have a drink in your hand, you can fit in with the buds – and a nonalcoholic drink is almost preferable, what with the positive effects on the wallet, your mindset, and the morning after.

In the weeks since August ended I’ve only drank twice; with two beers to fit in with friends each time. And it felt horrible the next morning. It was incredible how low my tolerance had become after the abstinent month – and I find that now the results don’t justify the means. I’ve never truly enjoyed the taste of alcohol to be honest; I just binge drank in college to get drunk.

So from now on I’m going to try avoiding unnecessary beers whenever possible, barring sips from new flavors here and there. The confidence is all in your head, and NOBNOM taught me that if you can stick to your promise, the real confidence is much preferable to the liquid kind. You just have to excommunicate the option of drinking entirely.


So why was NOBNOM a legitimate reason? I hazard that is was my conviction to stay true to something larger than myself. This may be the same conviction that grips nationalists and religious fanatics, who place the needs of a ‘greater power’ above their own needs for life or personal liberty (or a cold beer). Add in fellow adherents for group strength and repercussions for failure and you’ve got yourself the same recipe. Though in this case the only repercussion was letting yourself down – Tim’s money prize wasn’t even enough to keep my checking in on Lift. What do you think are the minimum requirements towards getting someone to stick to something?

The lack of NOBNOM going forward means I’ll have to find another greater power to keep me going – assuming I decide to continue. I don’t regard masturbation or social drinking in moderation as truly harmful, but they are insidious distractions from other, better uses of my time. And it is another great way to build self discipline (which is strengthened like a muscle), which is important to me.

So we’ll see how it goes in the future. But at least this NOBNOM has taught me that yes, I really can stop if I want to. That fact alone, and the accompanying self respect upon success, has made it worthwhile for me. I encourage all to try cutting out something you think is needed from your life and see what happens (although you don’t need to be as serious as Leo Babuta, who experiments with going without big things like sitting, computers, or cell phones.)

Why Every Straight Man Should Go To A Gay Club

I’ll never forget the first time I entered a gay club. I was in Barcelona, hot in pursuit of a beautiful Brazilian I had met the week before. She had invited me to meet her inside the club along with her flamboyant gay friend and his boyfriend – but the problem was, this particular establishment had 4 stories and was packed.

I spent a nervous twenty minutes wandering through the sweaty mass of humanity within, skirting the edge of the mysterious ‘Dark Room’ in the basement, (from which telltale sounds emanated) trying not to make eye contact with anybody, and turning down the bold advances of many a young Spaniard. When I finally found my friend, I latched on to her with both arms and pleaded with her to promise not to let me out of her safe grip.

Never before in my life had I been on the romantic defensive. I have always been the aggressive party, pushing forward blindly and perpetually worried about rejection. Now I was the one doing the rejection. The hunter had become the hunted.

And this was no easygoing neighborhood bar. This was a gay nightclub in the heart of a gay neighborhood, and the majority of the clientile were rightly unleashing their libidos in one of the few places they can freely do so. I have no problem with that – the only issue here was that all of it seemed aimed at me. Many of the pairs of eyes I saw carried unspoken invitations. The dancefloor had minefields on it – brush too close and your neighbor sees it as a flirtatious move. Men would come up to me unrequited, ask me where I’m from, and grab my hands and tell me how beautiful I was. Safe to say I was entirely out of my element.

And yet this is the scenario that most women confront within almost any nightlife location. Mispercieved dance moves, perilous eye contact, unwanted physical attention – these are standard features for female nights out. The aggressors are me and my ilk – I certainly spend my time at straight clubs trying to make a connection of some kind with the ladies, be it visual, conversational, or physical. Though I have never ever physically accosted a stranger, the men in this club were only a step further along the same action sequence I had often fantasized of – only aimed at the opposite sex. I understood their thought process.

This is why I contend that all straight men should go to a gay club at least once in their life. Only there can a straight man come close to understanding what it is like to be a woman in a straight club. And this is advantageous for both parties – with a knowledge of the other side, a straight man will approach women more effectively, yet with greater respect. The closer he gets to understanding how she feels, the better off both will be.

And he’ll never get it otherwise. There are aggressive women out there, but they only come along once in a while, and never will you have multiple individuals come up to you unbidden in one night. No, you need to be on the receiving end of male libido, and while you will not get that in every gay club you enter, you will certainly get closer to it there than anywhere else. Most of the surroundings are the same (dim lighting, expensive drinks, prohibitively loud music), with the only difference being the sexual preference of the clientile.

A man who does this will discover (as I did, and as all women know) how vulnerable you feel without a girlfriend by your side in a room full of hungry males. They will discover what it feels like to have stranger’s eyes boring into you with no invitation. And they will ceratinly understand why women go to the bathroom in pairs. Any man who remembers those feelings when he next descends onto a dancefloor in search of a partner will do so more respectfully, effectively, and thankfully.

Yes, I know that not every gay club is a raging mass of unselective homosexuality; results may vary. But entering the tamest of gay establishments will illuminate the paradigm shift that I’m talking about, even if nobody makes a move on you. My predatory experience in Barcelona was an extreme of that environment, yes, but it is certainly not singular. You’ll just get more looks and fewer gropes depending on where you go.

To treat someone as an equal, you have to understand them. And I doubt I speak for myself when I say that I do not understand women. But thanks to the above experience along with the several dozen gay nightlife excursions that have followed over the years, I have some insight into the enigma. I would encourage all of my heterosexual male friends to do the same. Push aside the mild discomfort and learn a little more about those different from you, be it in gender or orientation.

Plus, it’s a lot of fun! I’ve found the gay community to be generally friendlier, the drinks cheaper, and the music better. (Remember, gay Detroit men invented the forebears of house music which is currently the global young soundtrack) Bring along some female friends if need be – women love it because they don’t have have to be on the defensive the whole time. Just don’t pitifully clutch their arms for protection the whole night like I did…

(This piece originally appeared on Thought Catalog)

True Friends, or Fellow Fans?

The two best things in life are doing things that you like and spending time with people you like. If you don’t care about the activity or the people you’re doing it with – why do it at all? Obviously, if you combine these two into enjoying both the activity and the people, then you have the stuff life memories are made of. Yet due to a variety of reasons you usually lack one of the two – preferred friends or  preferred activity.

I’d say the first is more important than the second – with friends, even the most odious of experiences can become treasured. But this is also the most likely obstacle. Due to work, jobs, or a cavalcade of obligations for both parties, the ability to spend time with people you choose doing the activity of your choice is often limited to short tired weeknights or longer adventures on the weekends. It depends how adventurous your social circle is.

Yet this  means that the majority of your waking hours will be spent in the company of people not freely chosen. Instead, they’re individuals who you interact with out of necessity. Coworkers, the people who live in your building, the guy you buy a hot dog from for lunch, and so on.

If you’re lucky, super friendly, or highly compatible, these people can become your friends even while they fufill their roles of worker, housemate, or service person. But those are the happy exceptions rather than the norm – most requisite interactions are marked by polite acquiesence in order to get the job done, not in order to spend undue time with you. Not many people chitchat with the taxi driver or the receptionist.

Alternatively, you could have time and people to play with, but face the problem of your friends not enjoying the same activites you do. A prime example would be friends of mine who I can spend a lovely dinner or bar night with, but would never want to go on a daytrip with, or indeed, partake in most of the things they choose to do with their free time. Then you’d have to search outside of your existing network to find people who like the things you do. Yet this brings with it another problem.

It is the nature of leisure activities to pull people towards them who are also fans of said activity. (duh) But unlike jobs, eateries, or transportation, leisure activites are optional, which means that when choosing recreational activites, you are not just choosing the activity but also the fans – the people you will be spending time with as a result of that activity.

In theory, this is great, because it will introduce you to other people who already have one half of the recipe for happy life memories – they have the same favorite activity you do. But just because you both like the same thing does not mean you will get along – that interest is only one facet of a personality.

You’ve likely seen this firsthand in almost anything you do on the weekends, but here are a few interests of my own with wildly disparate fanbases: the outdoors, electronic dance music, and startups. All of these have different clientile – not exclusively of course, but here are some of the traits I find unusually correlated.

The Outdoors

The people who I often encounter in REI and on hiking trails are usually easygoing, liberal, white, and own mid-sized dogs. I can empathize with them on the above and with national park recommendations, but on matters of personal ambition there is often a disconnect. I’ve noticed over the years that many of them are content to spend their lives entirely in the mountains as wilderness guides. I knew one guy who was fine doing part time jobs he was apathetic about for most of the year because it gave him the money and time to get back on the slopes during winter. That’s fine for him, but I want to accomplish more in my life than a list of mountains summitted. I can’t talk matter of business or productivity with most people I meet on the trail.

Electronic dance music

Fans of these genres are usually millenials like me, but if the concerts and raves I’ve attended are any indication, they have a lot more tattooes, piercings, and interest in recreational drugs than I do. I can connect with many of my peers on a deeply passionate level through song and artist commiserations, but outside of music, I have almost nothing to talk about. You can see this just by browsing Soundcloud comments and seeing how many needless drug or sex references there are.


These are the people I get along with the most. Since self betterment is a philosophy that encompasses a wide range of lifestyle choices rather than what you listen to or do on the weekends, I have a lot more to talk about with fellow wantrepreneurs. We can trade productivity tis, book recommendaitons, personal creations or writings, and so forth. If I had to find a problem with this group of people it’d only be that some of them are overly business minded. It’s not common, but some are in it for the money and prestige – they could take a lesson from the outdoors group on lightening up and having fun.

Knowing the above about my fellow  fanbases, I take care to cultivate my personal brand to be a lantern that attracts the kind of moths I want to hang out with. You’ll notice my website isn’t devoted to the outdoors or music – that’s not just for professional reasons. On the trail I mention the other adventures I’ve had, in the club the other concerts I’ve been to, and at conferences my website and the book I wrote. Only as the connection grows do you start to learn about the rest of me. Rightly so – having friends with one deep but narrow interest in common would get old quickly, whereas those with many mutually preferred activites lead to long fruitful friendships spent doing varied things we both care about.

Are you conscious of the ways your interests bring you into contact with likeminded people? Which of your fellow fanbases has the most in common with you?

Why Pickup Artists Make Good Entrepreneurs – But not Vice Versa

A few of the people on my Heroes tab  (a list mostly composed of self made entrepreneurs) got to where they are through the Pickup Artist (PUA) community. People like Tynan and Mark Manson explicitly walked that path, but many of the others have skirted close, even if they were not ever ‘full time’ pickup artists (like Maneesh Sethi having lived with Papa from The Game and Michael Ellsberg, who almost wrote an ebook aggregating interviews with the best PUAs).

This is no coincidence – the lifehacking mindset that comes with pickup fits well with ‘anything to get it done’ mindset of an entrepreneur. However, I believe that a PUA perception of the world is intrinsically poisonous, while the latter can be applied healthily towards any pursuit. Here’s the similarities I see between the two, and why I condemn the PUA mindset.

Both embrace repeated failures

Pickup artists recognize that you have to fail at picking up a woman in order to understand what to do in order to succeed. It’s not uncommon for them to approach over a hundred women in one day and only get a few numbers, but hey, then you got some numbers and a whole lot of practice. There’s all sorts of self enforced rules they espouse to facilitate this, like requiring you to talk to a girl within five seconds of thinking about it, so as not to psyche yourself out. Or demanding at least twenty approaches per establishment, in order to overcome the nervousness and learn from each approach.

Similarly, entrepreneurs regard failures as valuable learning experiences that they can use to fuel their next endeavor. While they would probably like to succeed on their first business ventures, it is not uncommon for most successful founders to have several burning wrecks in the past before she got to where she is now. Accordingly, the community applauds ‘failing forward’, making Little Bets that don’t always work out, and acting in moments of doubt, just like the doubt inherent in approaching a stranger. Thomas Edison’s ‘You haven’t failed, you’ve just found 1000 ways that don’t work.” applies to both mindsets.

Both require false confidence bordering on arrogance

Walking up to a stranger and immediately presenting yourself as a possible partner puts your personality, appearance, and ‘manhood’ on the line, and is thus incredibly difficult to do without believing in your own worth. This is what draws many men to the PUAs – they promise to quell this self doubt and restore self confidence. There’s all sorts of ways to do this – I remember in The Game Mystery would have his disciples run around their living room giving each other high fives and shouting in order to build up adrenaline and testosterone for a night out of approaches. To become a PUA you must believe in yourself, which is a worthy goal, but sometimes leads to a false swagger that can be inimical to authentic relationships.

Likewise, for an entrepreneur to throw himself into a venture, he must believe in himself, his team, and his idea completely – there can be no room for doubt. Of course, his idea is not always valid, and nobody is perfect, so he must develop a sort of warped reality to get him through the naysayers as he throws his entire waking life at an idea. This confidence must be all-encompassing, or else his doubt will poison his decision making effectiveness. Likewise, this shield of arrogance that could ruin him if it hides the business weaknesses in his venture.

Both demand the dedication of a monk and the memorization of a nerd

PUAs memorize different opening lines, study other artists’ stories of their nights out, and familiarize themselves with all sorts of pickup workshops, books, and pedagogy. It’s no academic subject, but it is a discipline just like any other with rules to be learned and facts to be known. Many PUAs contend that you must devote yourself entirely to the ‘art’ or you will fail – so long hours hitting the books are required for entry.

Entrepreneurs must be knowledgable as well, but their ventures can fall into many different industries and thus their body of knowledge is more varied than studying the few thousand ways other men have endeavored to approach women. They have to know about industry current events happening, be familiar with the technical aspects of their product, and know how to sell themselves with their idea in pitches and branding. Hence all the books and school courses on how to be an entrepreneur (although the best way to learn is to start something yourself). You don’t have to be a scholar, but you have to know your stuff.

Both push you towards writing

As PUAs become known in the community they invariably start to teach what they have learned to the masses of losers they rose up out of  – for a price of course. Almost any name brand PUA has workshops, books, and tapes available for sale on their personal site, and some of them make a living entirely off of this material. I would guess that this happens because their study of pickup takes up so much of their life that they want to monetize it by teaching what they have learned to others. It all comes off as rather smarmy, however – look at any pickup site plastered with ads full of supermodels and promises to help you “sleep with any woman you see within hours”.

Meanwhile, any successful entrepreneur has books written about them (if not by them), and many who tried and failed have written about the experience in one way or another. From Paul Graham to Joseph Walla to Daniel Tenner, founder blogs, books, and journals are everywhere. The monetization rhetoric here is obvious – as an entrepreneur, of course they will try to turn their experience into a business.

But they are not the same

Since the two pursuits have so many habits and mindsets in common, it’s no wonder that many PUAs become entrepreneurs, although the reverse transformation is not as common. I believe this is because the pickup mindset is fundamentally misogynistic and limiting – unless it was what introduced you to lifehacking you aren’t going to embrace it from an existing position of success. While there are plenty of pickup techniques that normal men can use, once you start calling yourself a ‘pickup artist’ rather than just using a technique you read about online, you’ve crossed a line.

This is because at its core, pickup is about making people like you who wouldn’t otherwise. (Read: pretty women) It’s great that these men can find inner confidence and girlfriends from pickup, but think about it – they are changing their  personalities in order to appeal to random women at the bar. And they’re just doing it for the sex. Sure, they’ll end up with a steady girlfriend after enough attempts, but that’s not why they started pickup – just look at the way they talk in the forums and the ad copy used.

And they’ll never find a wife that way – because they’re using carnival tricks and deceptive techniques in order to garner these womens’ attention. You’ll never attract someone that way who likes you as much as someone attracted to the authentic you. Otherwise she is being attracted to a charade you are putting on, not the real you. Look at how many pickup artists have found their perfect life partner and settled down with her: None (that I’ve heard of). The smart ones have moved on to writing and other pursuits post pickup, while the rest continue peddling their workshops and techniques while rotating through a never ending parade of unfulfilling relationships and sexcapades. (Or try to build a  ‘mens’ rights’ site)

This is because the PUA mindset views women as nothing more than a challenge – rather than a human being. Their philosophy  deconstructs women into archetypes in order to succeed, losing their humanity in the process. Plus, they’re meeting these women mostly in bars and nightclubs, (often on weekddays, in order to have more practice time) which is a self selecting subset of the public; it’s not indicative of all women. Plus, they tend to view ‘no’ as a sign that they botched their approach, instead of a sign that she actually isn’t interested. Sometimes it’s true that a ‘no’ isn’t absolute, but obviously, internalizing that worldview is a dangerous path.

Entrepreneurship doesn’t come with any of these specific shortcomings, since it is focused on successful business endeavors rather that on getting with women. Leaning how to market a product, pitch yourself, and achieve product/market fit are all useful skills to bring to the rest of your life without an accompanying chauvinist undertone. Whereas if you go vice versa, you’ll have to unlearn some internalizations if you want to have fulfilling romantic relationships. Yet they are both very empowering philosophies.