8 Weird Things All Guys Should Do at Least Once
Not a cringe Buzzfeed listicle, dw.
I really have no interest in making this Substack too political. Its branded as “A unique analysis of modern American life”, and that’s more the route I’m going to go.
No, don’t worry. This won’t be a cringe Buzzfeed-style “listicle”. There will be no use of the word “wanderlust”.
This also won’t be one of those incredibly basic “men’s help” style articles that are all the rage, either. You’ve seen those articles- they make a caricature out of masculinity and talk about “power tools!!” and “cigars bro!!!”, and 99% of the time have some affiliate link at the end to shill some preworkout to whatever impressionable young man could stomach to read the whole thing. This is just a unique list of things that would help any guy, young or old.
Lastly, I have way more readers than I thought I would (cool!) so if you happen to be female, pls read it too and send to a guy in your life you think would enjoy it.
(Disclaimer: Try all this stuff at your own risk. Please don’t die or get shot or lose all your money. I’m not liable.)
These are in no particular order of importance.
#1: Throw a lot of money on a long odds bet you actually believe in.
It also has to be feasible. Put aside any biases or affinities and look hard at a sport or competitive arena you know well and put your money where your gut tells you. I know this sounds really dumb (it sort of is at first glance) but hear me out- it’s a great exercise in trusting your intuition. That’s a skill we’re all innately born with, yet so many of us ignore. It’s easy to let personal barriers fall to obligations, let interpersonal relationship issues slide, turn a blind eye to what bothers us. However, in putting one’s own hard-earned money on the line, it coaxes out a new level of prudence and due diligence that normally isn’t tapped into. You’ll be proud of yourself for taking the leap, even if you lose. The funniest thing about this? I’ve done this myself and suggested it to others, and the bet hits more often than it doesn’t. It’s almost as if the universe is rewarding your authenticity.
(I know I’ll get asked for receipts- my longshot bet was on Germany before World Cup 2014 even started. I’ll never forget that extra time period for as long as I live.)
#2 Get into a physical altercation- and lose.
This one should be done in the confines of a gym setting or another form of controlled setting. Please don’t go to the wrong corner in the wrong neighborhood, hop out of your car and say “Everyone wearing a red bandana is a bitch”. That’s not what I’m saying- the idea isn’t you get physically harmed, it’s that you become at home with the fact other people on planet Earth can kick your ass. As men we seem to be born with an internal sense of invincibility, and you can often hear such cringe phrases as “Bro you wouldn’t like me when I’m angry, bro I’m crazy I see red bro!” Fighting experience will teach you that the calm, knowledgeable man wins 99 times out of 100. It will teach you that the wiry 5’9 guy with glasses could be 100x more dangerous than the 250 lb bodybuilder. Bench press 1RM doesn’t correlate to combat nearly as much as the average guy thinks. I trained grappling and boxing all throughout college at a gym that housed several UFC fighters (a couple which became title holders). Witnessing the levels of ability firsthand of some of these athletes was insane, especially when rolling (sparring) with them myself. Eventually you take so many one-sided beatings that the thought of fighting no longer scares you. How does this help your life? Well, if you’re out and things go south, watch as everyone around you starts pacing around, getting their heart rates up, the fight or flight kicks in. You’ll be cool as can be- you’ve been here before, in the worst spots possible, punched or choked out. It’s damn near a superpower, and one you’ll have for life. You’ll also naturally be more respectful of everyone you meet, because you never know who knows what- and you’ll stop being afraid of the “I see red, bro!” guy.
#3 Solve a medical issue without a doctor, or defy everything they tell you.
Hey maybe it can be an injury from getting your ass kicked. All kidding aside, be careful with this one. I’m not saying rip your own teeth out or try to give yourself stitches. However, the medical community gets an awful amount of trust from the general population, even when malpractice numbers are alarmingly high. I’m not being a kook here, you can check the numbers yourself. I’m also not saying never go to the doctor, but the next time you have an issue that isn’t an emergency, see if you can solve it through personal research and trial and error first. It’ll feel empowering and give you a newfound sense of self-sufficiency. As an example, instead of sprinting to the CityMD or Urgent Care (in real estate we call these establishments a “Doc-in-the-box) at the first signs of your annual sinus infection, see if you can give herbal remedies or dietary changes a try. You’ll save $ and won’t have to put powerful, side-effect ridden antibiotics in your system. I recently went through this myself over the summer, I had broken my right arm in a freak occurrence. The original prognosis was “stay off it, give it 8 weeks”. Through dietary implementations (extra protein, daily bone broth consumption, a litany of supplements) and mild strengthening exercises, I cut that time table in half. I’ll never forget the Doctor’s face after my latest X-Ray showed no further damage. “I’ve never seen that quick a turn around before”-he seemed disappointed. That should tell you something right there.
Obviously satirical, but there’s more than a couple inconvenient truths in there.
#4 Tell a girl “no”.
Ok what I actually mean here is “tell a girl who would like to come over and spend time alone with you No” (although some of you do need to learn to say “no” to your girlfriends in any context). The rules to this one are as follows: she actually has to be attractive and of interest to you, and also don’t be mean to her, just be like “I can’t tonight”. This one might seem random, but hear me out: too much emphasis is placed upon dudes getting laid in the modern environment. It’s unhealthy, and it causes a feedback loop where guys derive their self-worth from such instances, especially younger ones. Look, you need to know what you’re doing when it comes to girls and dating. However, sneaking out at 2:30AM to link with some 6/10 who will never ever in a million years be taken to meet your mother isn’t exactly the massive conquest most guys think it is. Take a step back and realize you don’t have to swing at every pitch that comes in over the plate- you’ll be much better for it. Plus, if you’re getting these types of propositions, then odds are there will be plenty more of them in the future. Pick and choose, and enjoy the good ones.
She’ll get over it, I promise.
#5 Go out to eat by yourself.
Okay so far you’ve lost a few hundred on a longshot football bet, you have a black eye that you tried to remedy at home and just made worse, and you just told this week’s Tinderella to take a hike. Now you have to go sit in a popular restaurant- by yourself. Also no, scarfing down your double chicken bowl in the corner of Chipotle in 5 minutes flat doesn’t count. I’m not trying to torture you, I swear. The reason I suggest this is that it’s great for breaking out of your shell and learning to establish yourself in a new environment in a short amount of time. This is a life skill that is worth way more than many would think. The easiest way to do this would be at a restaurant that also serves food at the bar. Order something you like, get a drink to loosen up. Make conversation with those around you, with the bartenders as well. There’s an incredible amount of newfound confidence to be gleaned out of this if done right. I know it sounds rudimentary, but ask around and you’ll be shocked how many guys of all ages have never done this. Last bit- get good at this and you’ll start to prefer it to entertaining company on some nights- believe me.
#6. Do a 24-hour fast.
Hope you enjoyed the solo meal, it was the last one for awhile! In all seriousness, this is a tip that has a litany of health benefits, both physical and mental. I don’t want to turn this into a full research paper and cite sources and all that boring stuff (you know, real journalism), but trust me on this. It’s a great way to give your body a break from the constant churning of calories, and it will also burn some fat towards the latter half of the fast as the body turns to fat stores for fuel. (If you feel scared, try doing an 8 hour fast, then a 16. As always, have food on hand if you feel lightheaded or that you can’t make it. Let a nearby friend or loved one know that you’re doing it as well, this will alleviate some anxiety if you’re new to it.) Those are cool features of a day long fast, but the real prize is the mental acuity. You will feel as if you were psychologically shot out of a cannon after about 6 or 7 hours. The razor sharp mental processing you experience in a long fast gives a natural high. The best way to do this is as follows: I like Saturday night into Sunday evening. (It doesn’t have to be 24 hours exactly on the nose) Put aside an intellectual pursuit or project you’ve wanted to do, and dig into as soon as Sunday starts. You’ve already knocked off ~8 hours in your sleep, so you start off a third of the way there. Rip through the project you’ve chosen, ignore the clock, use black coffee and water to keep yourself alive, and reap the benefits. Much like #5, I believe this will become a staple in your life if you do it right. Remember, willpower is a muscle- it grows from actively being used.
Unironically how it feels.
#7 Live alone for at least a little while.
This means in an actual legal domicile with you as the resident. Spending a week or two solo while your girlfriend/roommates/parents are out of town and subsisting on cereal and pizza is not what I’m getting at. Again, the list is compiled of things that I’ve seen almost no one else do, and far too many of my friends have gone down the path of what is called “the mommy-to-girlfriend pipeline”. I currently live on my own and while yes, there are challenges to it and it can get a little lonely, I can confidently say I’m a far better man for it. You’re in control of everything you do- food, clothing, sleeping hours, schedule. It sounds a little dramatic, but it is a sink or swim style test. Nobody is prepping healthy meals, doing your laundry, waking you when you oversleep. I see it as the final level in actually growing up. Lastly, you get a feeling of personal freedom that you never want to relinquish. Once you master yourself and master the ownership of your own time, you’re in a really good position to succeed in other facets of life.
Okay, time for the last one (and my favorite):
#8 Start asking for absurd things (because you just might get them)
This is something that I’ve employed more recently, as in the last 3 or 4 years. The brutality of the real estate industry desensitized me to the word “No”, and I’m forever grateful. This last tip requires some nuance- you want to avoid low life behavior or being insulting. This is best used with experiences or with the artificial barriers life has in place. Think less “asking for free stuff” and more “asking for access”. I’ve used this method for everything ranging from getting to go backstage and meet rappers, getting my sporting event tickets upgraded, gaining new business, and sitting at exclusive tables in bars and restaurants. I’ve even used this method to turn my favorite real estate YouTuber into a client, and to get myself on a Facetime with Conor McGregor, of all things. You never know what will happen if you just ask. “No” won’t kill you, but “coulda shoulda woulda” can keep you up all night.
That does it for this post. Go out and try some of this and let me know how it goes!
Also, if you have some ideas for future writing, I’d really appreciate that.
Have fun and keep warm (winter temperatures finally hitting the Island on Sunday)
Talk soon <3
-John
13 November, 2021






you’re brilliant <3