Mental Prisons

let mental prison be any conviction that has a negative impact on our lives.

when asked how i accomplish X or Y, my answer (“mindset”) rarely satisfies the inquirer because mindset is not a checklist of errands.

in this piece i’ll reach into my black box[2] and share principles that produce results people seem to want to emulate.

always / never

if you’ve ever been fat and then skinny, lazy and then hard-working, or late and then on-time, you are acutely aware of the power of habits.

everyone has habits, good and bad, like brushing our teeth or going to the strip club. and some habits are easier to form (or break) than others.

as we age, our tolerance for habits we like and don’t like decreases. we’re more annoyed that we are fat and single at say, 34, than when we were 21 and “would get in shape after graduation.”

and here’s what we do about it: we attempt to break (or form) new habits with tools like Always and Never:

  • i’m never going to drink again
  • i’m going to work out every morning
  • i’m never going to forgive him
  • i’m always going to read before bed

but since humans are fallible, we are incapable of leveraging these tools correctly. so when the system inevitably breaks, we go back to our old ways, eating Snickers and watching re-runs of Lost.

i personally battled with this mental prison through a temporary embargo on my drinking. for 4 months in 2019 i didn’t have a drop of alcohol, and didn’t miss it either. i got in great shape, lost ~28 pounds, and wrote a book about it.

then i spent a month in Italy. suddenly my “never drink” habit was challenged by two objective truths: Italian wine is cheaper than bottled water, and i love Italian wine.

if i were a masochist, i could have ignored objectivity and abstained from alcohol in the same way i abstain from hookers. but a trick called “moderation” afforded me the ability to indulge in something i enjoy, still improve my personal fitness, and remain married.

the pseudo science behind the Always and Never toolbelt is it helps us demonize things we don’t want in our lives, and Infatuate with things we want more of. but is demonizing a glass of fermented grapes, reasonable? is pretending to obsess over a smelly gym, 7 days a week at 7am, normal?

to build (or break) habits that stick, lean into your inadequacies. this is why 1x /week “cheat days” work. it’s not so much about your body being “shocked” by extra carbs or sugar as it is about maintaining your sanity.

conditional thinking

a couple months ago i began teaching myself to speak Korean. i don’t have specific reasons to pursue this endeavor, but i wrote a few down in my notebook anyway:

  • help the intelligence community, e.g. by hacking a North Korean website
  • give a presentation at a Korean tech conference
  • watch Old Boy without subtitles
  • be interviewed on a Korean talk show as one of those weird white guys who speaks Korean

between my daily vocabulary and grammar studies i watch YouTube videos by peers further along than me, describing their journey and sharing tips. then i skim a garbage pail often referred to as the comments section.

“no WONDER you learned to speak so well, you took an immersive class… i wish i knew Korean but i don’t have anyone to practice with where i live… well YEAH you learned quickly, you got to fly to Korea for 4 weeks!!”

and on and on.

these YouTube warrior losers are practicing what i call conditional thinking by deflecting blame (for their lack of learning) on circumstance.

“IF i could solve X (difficult external circumstance), THEN i would Y (easy personal responsibility).”

there is no magic spice in the air that teaches you a language simply by being in the target country. i would know, as i’ve been to 30+ countries and can only say “thank you” in 3 of them.

to avoid conditional thinking, first allow the thought to express itself: “if i didn’t have to work long hours, i would have time to go to the gym.” then attack, or ignore, the circumstance (long hours):

  • attack by quitting your job, getting a new one, telling your boss “no,” hitting the gym at lunch time, etc.
  • ignore by having coffee after dinner, exercising before work, or finding contentment in being fat

the only guarantees in life are death, taxes, and sub-optimal circumstances creating friction between you and your goals. the only option is to do something about it.


i’ve been called a class clown, musician, inmate, CEO, marketer, product manager, worship leader, person, cracker, f-ing retard, writer, bad computer programmer, founder, volunteer, and many other titles.

most people choose their favorite title and then build an identity around it. they constrain themselves to specific behaviors, zip codes, accents, political leanings, and diets that they believe match up with the fake title they’ve chosen.

but why live in a tiny NYC apartment because you are a “starving artist” when you could live on a ranch and paint the sunset every evening? why vote democrat or republican just because you’re insert skin color?

i have never allowed myself to be defined by a title. i am not a marketer, developer, or anything. i am a guy who enjoys iced coffee. and that bothers people who prefer i fit into a box, because they are in a box and misery loves company.

explore a cross-section of disciplines, ideas, and environments, lest titles ban you from their entry.


releasing yourself from these mental prisons will probably take more than 20 minutes. i spent years thinking i was a loser, that i was unlucky, that i was genetically inferior.

i still believe i’m unlucky and mentally ill. but i also don’t allow those circumstances to prevent achievement, and neither should you.

to begin your jail break, investigate recent thoughts or convictions that negatively impacted your life. just by doing this you will be more mindful than most of your friends.

next, figure out the prison to which these thoughts belong:

  • always / never (extreme demonization or infatuation)
  • conditional thinking (blaming circumstance)
  • titles (suppression of identity)

finally, deconstruct why you feel that way.

is being a “new dad” (title) just a coping mechanism to avoid pursuing your entrepreneurial dreams? do you want to learn to code, but can’t afford the education? or maybe you miss your estranged mother, but promised to “never” talk to her again and it’s killing you.

i don’t know your burdens, but these lenses can help release yourself from them. be free.