Working smart, Working hard

“work smart not hard”

“hard work pays off”

“no one ever did anything great without hard work”

“hard work got me here”

“work” takes up the majority of our waking lives

We form emotional ties to “hard work” and “smart work”

Yet 99% of us work just to make ends meet

And the top 1% face a burnout epidemic, an identity crisis, a great resignation

I began in the 99%: Bankrupt, broke, etc, and now I’m in the 1%

I wrote this post to understand 3 questions that captivated me these last 10 years

  1. what does it mean to work hard / work smart
  2. when does smart work matter, when does hard work matter?
  3. how do you work smarter / harder

What does it mean to work hard / work smart?

Working smart = quality of thinking

Working hard = quantity of doing

“quality” is hard to measure but in any moment you’re between 0 & 100% of your peak

ask yourself

  1. what’s a time I was doing my best work?
  2. am I in a similar mental state now as I was then?

entrepreneurs call it “clarity”

artists call it “inspiration”

programmers call it “flow”

It’s your mental state when you’re doing your best work

It is tempting to define “smart” as “doing the right things” but this has 2 problems

1. it depends on outcomes

you can play an “optimal” strategy in poker and still lose, life is rarely under your control

2. it assumes there are “right things” you can know to do

we often don’t have all the information, we have to guess, make bets

When smart work matters, when hard work matters

The poverty plateau: Working smart becomes more important with wealth

When working a job that pays for hours worked & not for output there isn’t much value in working “smart” because it doesn’t impact your pay

But when doing an output based job there are many ways to play, and you are rewarded more upside if you make a few correct decisions

I’ve seen friends grind for years trying to make a company grow with $0 revenue

I’ve seen other friends spend a few hours building a demo or sharing a tweet and raise millions of dollars in days [2]

More ways to play a game seems to mean high quality thinking dominates in importance

I find so many individuals who are born poor & identify with “hard work”

And they grind hard without focusing much on how to think smart

For example this camp of people will often take a job paying $5/hr full time and suffer through it to pay bills instead of taking an interest free loan and 6 months job-free to learn new skills so they can get a better job.

I call this the poverty plateau.

When you’re in poverty you have no choice but to work hard

You develop coping mechanisms to justify doing really hard work

A common coping mechanism is to just make “hard work” part of your identity

The problem is later on, you have to also “think smart” and not just “hard”

This may cause some coming out of poverty to have an identity crisis

They’ve never thought about other options before, or taking what feels like “the easy way out”

The solution is to expect to re-assess your identity as you gain wealth.

Your friend groups + activities will radically change and so should your identity.

Wealth plateau: “smart work” being important doesn’t mean “hard work” isn’t

I’ve met many people who seem allergic to the idea of working hard

These are the people on twitter who call you toxic because you celebrated a strong work week, or work on the weekend or late into the night at times, even if it’s what you enjoy

They seem to conclude “working smart is often more important” therefore → “don’t work hard”

and their growth plateaus

i call this the “wealth plateau” as it seems to primarily affect those born wealthy

When born wealthy I suspect there is less need to work hard to meet baseline needs

And your immediate network has more wealth so they likely value “smart” work more

So “work smart not hard” is an understandable conclusion. But this reasoning is incorrect

Imagine a simulation with 2 people both pursuing the same goal

Assume both people are equally smart, i.e., both are capable of the same patterns of reasoning

And assume the criteria to “succeed” has an element of randomness

Across many simulations the person who works more will reach the goal first and more often

What’s the balance?

Both are key, if you demonize hard work or smart work you’ll likely plateau

So I do 2 things

  1. figure out how to get into highest quality mental state for work
  2. work in that state as much as possible

Ok cool, but how?

Over 10 years of experiments I got from 2-3hrs/day to 8-12/hrs per day of high quality work

You have to figure out what works for you. I hope my journey inspires ideas!

My process

  1. Put stuff I will do in my calendar
  2. Show up and start on task I’m most inspired. Continue chugging through stuff I planned for the day. Bias to stuff I feel inspired for, but if I have something that must get done then make sure you show up and start it, you often become excited once doing it.
  3. while working
    1. If a <2 min task hits my mind, just do it, otherwise slot in calendar
    2. if after 20 minutes i’m still not engaged in work (<50% of what I know is “peak”) & feel inspired to do something else then do that thing
  4. if i still can’t focus on anything then go exercise, relax, socialize

The goal is to get (4) down to ~0% & never feel fogg

(a) and (b) are fallbacks for ADHD that may look bad but they make me super productive
  • Most of society pushes the “just be focused” mindset, stick to it.
  • This can sabatoge my productivity because on a neurological level my focus is chaotic
  • It leads to me grinding with force, not getting stuff done, feeling bad, repeat.
  • yet when I’m fixated on something I can grind on it for 17 hrs and move mountains.
  • So I choose to just do what works for me.
  • e.g., (3.a) When I catch small tasks on my mind I can unblock so many projects in a day, make intros, followup on sales, finish chores, instead of pushing it into a task list and making it a grind. If I schedule “chores/sales/etc” I almost never do it at that time.
  • (b) takes advantage of my tendency to procrastinate even if I want to do a thing. In most cases if I postpone it I’ll do something else in the present with more energy, and this gives me a feeling of progress, then I usually end up spontaneously becoming excited about the original task at some point in my day and I come back and crush it. I end up getting both done way faster than if I just forced one at a time.
    • e.g., I may have guitar practice scheduled but not feel it, so I just code instead, and then suddenly I’m like “ITS STIME TO PLAY GUITAR” and i practice way harder.
    • If I never become inspired to do something even after a week, if it always feels like a grind, it may mean I shouldn’t do the thing.

What I’ve learned works for me

sleep: 7-9hrs of sleep per night, wake up naturally, sleep more if needed
  • tried less, it blocks me from hitting same clarity
  • more makes me feel groggy, unless i’m training hard or sick
  • the optimal is to get up naturally right before my alarm at correct time
sleep: go to bed at time that lets you get the things you care about done in day

mainly social constraints influenced this

80% of social events are 4pm-9pm

so going to bed by 8pm is dumb it forces me to pick sleep vs social

during university I went to be at 9pm, up at 4am, because I had classes

this changes depending on environment

for a while 11pm for bed made sense when growing my company

when growth focused more on engineering, i had to code >12hrs/day

11pm didn’t make sense because it meant i get one coding block per day, and then have to either code way longer without break or prioritize social life

going to bed at 4am gives me two blocks:

code from noon-7pm, social/fitness from 7-10pm, code from 10pm-3am but it limited my coding ability

point is just wake up at the time where you can get the things done you want in life.

it changes often.

diet: 16hr fast
  • i focus better in fasted state. if it goes too long i get distracted thinking about food
  • maintains my weight
  • diet: don’t eat <3 hours before bed
diet: stimulants: varying 0-200mg spread throughout day depending on sleep/diet.
  • ADHD symptoms largely dominate my life.
  • having a stimulant vs not means going from not being able to sit still, to being able to sit still and think. it’s like having a lightening storm in my mind vs stimulants feel like a calm grassy meadow.
  • 10-30mg methylphenidates/day historically have helped a lot. i go on/off experimenting
  • 10-200mg caffeine per day, also experimenting
exercise: if my goal is to refresh my mind make it social * explosive

i workout 10x harder in groups

explosive feels like i get same amount done but faster & boosts my energy after

exercise: if goal is to process emotions workout alone * slow

slow to think inbetween sets & journal, alone to be in my head

this method consistently snaps me out my lowest moods in a few hrs

routine: biphasic day: work → rest → work → sleep
  • historically across 5+ years i have a clear circadian rhythm
  • first 6 hrs of day i’m focused af, no matter when i wake up
    • if its 5am wakeup i’m good until 11
    • if i wakeup at 7am i go until 1pm
  • then i crash a couple hrs, just can’t focus even with caffeine
  • then evening time i get a spurt of energy that usually leads into bed time, to point where its hard to fall asleep
  • so i just work with this. i get up and immediately begin working
  • i work until my crash
  • then i hit the gym + do social stuff
  • then i catch my second wind in evening
  • sometimes if i’m super engaged i don’t need a break, i’ll code for 17+ hrs but usually i have this natural energy dip
routine: 2hr Weekly Reflection + Planning
  • this gives me more perceived control over life, boosts my emotion
    • historically when I have my todos listed out for week I work harder than when I don’t
    • I have at visual proof that based on my estimates I can get this all done
    • so all that’s left is showing up. let’s goooo!!!
routine: 2 hour free-time blocked per day
  • gives me flexibility to complete stuff if it ends up taking longer than normal
  • gives me off-time for recovery if i need it
  • gives me additive time to get ahead of i have tons of energy
  • overall just gives me stronger perceived control over day by accounting for uncertainty
  • before this i was super rigid, would get stressed because 3 hrs in day would become chaotic and my schedule wasn’t working
  • schedule has to work >50% of time for me to use it consistently
  • and if im stressing about the schedule itself, then the schedule isn’t serving me well

meta: Flexible daily, rigid weekly
  • if i’m struggling to engage with a task on day i scheduled it, just push it out
  • i feel like sometimes days don’t go how you want, so change it up
  • giving myself that flexibility lets me recover when needed
  • but if i can’t find time in a week to get something done, something is wrong
  • i anticipate in this case i just don’t value the thing enough and should stop trying to do it
    • either delegate or delete it
  • things i care about i’ll get done if i slot them in a week

meta: iteratively develop a clear understanding of what i value in life
  • this is the compass that determines if i’m broadly going to keep pursuing something
  • figure out who i am, what i value in life, and experiment to align them better
  • i reflect on this naturally, probably every few days as i experience new situations in life
  • ask “how did this situation make me feel” → what values do these emotions imply I have
meta: S.M.A.R.T goals for daily work

e.g., if i’m doing a workout, have a list of the # sets and reps to do. i strictly do better with ambitious goals even if i miss, than not having a goal

e.g., if coding, have a clear thing you’re trying to ship. you don’t have to. but know what you’re after and why it matters. If the goal is to just try stuff and see what happens, then do it

  • meta: you can context switch while in deep-work, but have to still be in focus state
meta: follow curiosity when it happens organically

when i have clear goals i’m pursuing i naturally get curious about adjacent things

it historically feels better for me to follow that curiosity and go on little tangents

in practice: if i’m working on some specific task, don’t be afraid to detour for 5-10 minutes to something you find interesting

i find curiosity hard to create but powerful to harness

i can learn more in 5 minutes when curious about something than in 5 hours when i’m not

and following curiosity gives me more energy to do the original thing I was doing, as long as the tangent isn’t too long or acting as some form of subconcious avoidance of my main work

meta: stack things
  • e.g., in my calendar i stacked 3 goals I had: build community + do more deep engineering + try something new
  • I did this by starting a live streaming channel on twitch, this put together nearly 15 hours of tasks i had slotted in the week into one slot.
  • You can do a lot if you think about high level themes you care about and find ways to do activities that hit all at once
meta: i do way better work when overwhelmed
  • when i take on more than i can chew i think more clever, i push harder, when the stakes are high i just rise and do better. i grow into harder environments, and grow soft in weak environments and so setting expectations * goals to be higher is key to do my best work

things that didn’t work for me

mid day nap

ive napped like 5 times in my life

every time i do it i wake up feeling like i’m on a different planet and feel sick/dizzy

some people can clearly nap, this historically doesn’t work for me

if i get hit with absolute exhaustion i still try to nap as some sleep can be valuable

but i seem to go further by just having a long good-nights sleep, napping limits that

morning routine checklist

atm i just roll out of bed and code

my life falls apart biweekly and i have to spend hours just fixing everything (laundry etc)

would be nice to have a checklist in morning

for 10 yrs this has never stuck

the dopamine reward of repeating something causes the routine to fall out

i find its better in my life to optimize for positive habit-loops

this means figure out a routine that happens naturally, that you don’t need a list for

and if its not natural, focus on making it natural, not on how to check it off a list

for e.g., i keep forgetting to floss. so i put floss next to my bed, and now i floss

i had trouble with maintaining a 16hr/fast per day, if there’s snacks in my room i just start eating without knowing. so i stopped storing snacks in my room. this fixed it

yoga before bed

i never do this lol. like ever. it’s always “i’ll do it” but i don’t

because i’m too tired by end-of-day, just last thing I care about

maybe i’ll do a bit, but not like a serious routine. just feels too hard for a simple thing

if i want to do yoga i book a class to do it and workout with others. 10x better

this is probably due to my ADHD being worse later in day or when not on meds

15 min schedule blocks

worked for a while in University

outside of Uni its hell

life doesn’t go according to plan

so i spend most of my braincells stressed that i’m not following my schedule

very little smart work on this schedule, good for doing dumb but hard work

purely inspiration based work: 0 systems, 0 scheduling etc
  • tried not having a schedule I removed all my systems and wanted to see what would stick
  • It was pretty stressful. I had a lot of comfort that came from some level of certainty
  • kept feeling stressed I wasn’t reaching my goals
  • Scheduling gives me a perceived feeling of control, if i schedule something and do it I can at least claim I’m doing things. if I have no schedule at all then i can’t look back and justify im using my time well
  • so consequentially i’d feel i’m not improving as quick as i could
  • and this feeling of inadequacy is a huge driver for me to change things
  • so i began adding back weekly planning and more systems
  • also there is an element of ADHD in my brain that benefits from have systems i can follow. i near-pathologically enjoy making numbers go up, that may explain why i get so hooked on gambling and video games. i don’t want to not leverage something that’s fundamentally part of me since i was a child.
Set goals, no schedules

Had a period if time where i stopped scheduling and just set weekly goals for myself.

This was great because it removed the scheduling fatigue, removed pressure of having to do stuff. it lead to more spontaneous moments, but i had way too many goals and would never hit them I think because

  1. they weren’t scheduled at any time, so i just forgot about them.
  2. it just felt like i had a massive list of stuff to do at any given point with many moving goals

also without this schedule i also lost all routines like sleep/diet etc

3 hours of workout/routines/hobbies etc in morning

thrashed between this a lot.

had some “work life balance is everything” phase where i tried to force myself to work less

if you work first thing, feels higher output for my company. i can workout later in day as a break and then work more in evening but often i just get super tired mid-day and don’t get my exercise done and then feel bad which affects my work the next day

then i i feel behind on life and then can’t work in morning or workout in afternoon

so now i feel i’m failing at everything and this spirals into burnout so i tried forcing myself to workout/do life stuff in the morning instead:

  • i’ll often do this for a while and then eventually have a morning where i really want to work but i scheduled i have to workout. it stresses me out, i don’t enjoy the workout, i don’t feel i’m getting as much work done as i want and then i start having anxiety about this. eventually i just skip workouts in the morning, have some good morning workout routines but feel bad because i’m not following my routine, so again i just feel guilty/etc and it stresses me out

tl;dr is this is a meta topic across many experiments i’ve tried.

i don’t like rigid routines.

i need the flexibility to pivot out of something when its not working for me

so for exercise this means wake up and focus on the #1 thing i need to do until I can’t, then go exercise.

Sometimes the best thing to do in my morning is hit the gym, sometimes i want to code for 17 hrs and then just sleep, in this case i workout the next day. you can fit it all in a week, historically and this radically improves my clarity in all the work i do

doing the #1 thing
  • i read about this in some book, about how you should just obsess about the #1 thing to do and do that before other things
  • this caused me anxiety as the “#1 thing” changes often, and i can’t stop feeling guilty doing anything but this #1 thing so it just makes it feel like some stuff in my life is important and some isn’t
  • e.g., i’d be on a date and be like: coding is my #1 task this date is therefor wasting time
  • but that’s not true… shit isn’t all 1st order like this, there’s tons of longterm consequences of actions you can’t just plan it all out perfectly
  • also scoping what my #1 thing is was really hard so just too much thinking not enough doing good work

[1] This is a hard thing to accept for me but it’s something I’ve seen consistently from successful people I know. They all optimize working smart first before grinding out hours, but they also grind out hours it’s just not the first class citizen of their work.

[2] Debuild, Banana, Lexica