Submitted by Shawn Conn on Mon, 01/29/2018 - 20:54

To start 2018, I've made a resolution of maximizing my own happiness.

For the last few years, I've been focused quietly & intensely on my own projects & work, to the detriment of my own mental health. Being consumed with knowledge work (or deep thinking in general), has its own "gravitational" effects; it can pull down your own mental energy, blinding to your own agency as you're consumed with mental models of the world; being consumed in thought can create a type of time dilation where your experienced time feels much slower than clock time; life can pass you by pretty easily this way. Many of these effects have been pushing down on me for a while. 

On the physical well-being side, I think this time of year in the PNW is pretty probably the worst for happiness. Low levels of sunlight & a mild, but not warm-enough-to-be-balmy, air leaves you with an unsettling nature that's hard to point out unless you really reflect on it.

To kick the project off, I've started with reading 40 Ways to be Miserable, a short self-help read by a clinical psychologist. It's a nice short read with a snarky, reverse-psychology attitude about approaching happiness; it's easier to avoid the invisible pitfalls that we can myopically fall into, than trying to scale the massive heights of happiness on the horizon.

For the TL;DR crowd, there's this video that gives you a gist of it (not CGP Grey's best video, I think his format is probably too short to succinctly cover this book). 

I would say there are many lessons on here that seem obvious (especially if you've thought about depression for some time), but are easy to miss, especially for the severely depressed. I say 1/4-to-a-1/3 of the lessons can be described as short-term, quick-fix, happiness adjustments that, ultimately, leave you in the same-or-worse place over time (e.g. eating whatever your heart desires). I'd say another 1/4 of lessons can happen to you by circumstance, and slowly wear you down as you adapt to the circumstances (e.g. toxic relationships). Just being aware of these invisible happiness sinks is a good way to develop vigilant habits to force you out of these ruts. 

As I started reading, I kept a score of how often I did the following things listed. As it turns out, that's one of the suggested epilogue exercises to help you build an inventory of miserable things in your life. I created a simple scoring system for myself, a 0-to-5 star rating, on each lesson to build a misery index (there's something funny about a gold star rating on how miserable you are). The rating values are set to produce a simple score that can work with 40 lessons (or 10 lesson for each 4 parts).

The score corresponds to the following subjective views: 

Never:  🚫 
Less-Often-Than-Not: ⭐⭐
More-Often-Than-Not: ⭐⭐⭐
Often: ⭐⭐⭐⭐
Always: ⭐⭐⭐⭐⭐


The book is broken down into 4 parts, covering different aspects of life, each with 10 lessons you can follow to make yourself as miserable as possible. Here's the breakdown of how I scored myself.


  1. No Exercise | 🚫
    • For about 4 years now I've been the best health I've ever been, losing 40 lbs, trimming myself down to 15% body fat, achieving optimal blood pressure. Having a job where I do nothing but sit, I've offset that by walking almost everywhere (unless time's a concern) and doing exercises everyday to keep the muscles tone.
  2. Eat What You Desire | 🚫
    • While I like junk food as much as the next person, I rarely eat it. I'm more of an eat-to-live than live-to-eat sort of person. My diet stables are various sandwiches or rice mixed with various proteins & veggies. I have no clue what is being advertised in food comercials (another point made in the book), I avoid all kinds of ads like the plague. 
  3. Sleep Irregularly | 🚫
    • Definitely a 0 here. I keep pretty steady 7-8h of sleep a day, which looks to be within range for my age. I do find myself sleep binging time-to-time when I've gone long periods without sleep, but that's about it.
  4. Self Medicate | ⭐
    • It's taken a while to change my drinking habits formed during college, but I feel like I'm pretty good now. There will be occasions when I've overdone drinking, but I've found this less to be the case the older I've gotten. Drinking just doesn't have the same euphoric feeling that it once had.
  5. Maximize Screentime | ⭐⭐⭐⭐⭐
    • I'll admit I'm pretty good at make myself miserable here. Keeping up in the knowledge economy almost requires it. Combined with the fact that my other daily recreational habits involve an electronic screen (of one form or another), I spent a significant amount of time each day looking at screens.
    • For my daily productivity tracking, I use a product called RescueTime. It regularly reports between 50-60 hours / week, which doesn't include TV time too. If I had to guess, I probably spend 70-80 / week in front of a screen. Or to put it in more stark terms, 60-70% of my waking hours is spent in front of an electronic screen.
  6. Impulse Buy | 🚫
    • I'm a minimalist at my core and I hate buying/owning stuff unless it helps me achieve explicit goals in life. Every few weeks look around my home to find stuff to toss out if I can't say, "I use this or will need to use this in the foreseeable future"
  7. Borrow for Impulse Buying | 🚫
    • I haven't borrowed money to buy anything for over 10 years.
  8. Be Consumed by Work | ⭐⭐⭐⭐
    • I do this all the time, I'm in the prime earning years of my life and balance a day job with my own business. I've set a goal for early retirement to avoid the more dreary parts of my life as I get older, so it's kind of by design. If you ever seen the montage in Looper that connects the past/future, it's kinda like that.
  9. Always be informed | ⭐⭐⭐⭐
    • I like being pretty well read about the state of the world, politics, business and the like. Between misc. RSS news feeds sources, Podcasts, & a subscription to a couple of newspapers, I've overdone it here. 
    • In the last few years, it feels like some critical mass of news has been hit where it's impossible to keep up on everything in the world (without it being a full time career). I've marked this as a lesson to improve over this year.
  10. V.A.P.I.D. Goals | 🚫
    • This a cute acronym that refers to Vague, Amorphous, Pie (in the Sky), Irrelevant, & Delayed goals, as opposed to its equally cute counterpart, S.M.A.R.T goals (Specific, Measurable, Action-oriented, Realistic, & Time-defined). 
    • I'm a pretty goal-oriented person and when it comes to my goals I like to break things in small steps with concrete goals. My experience in software engineering has definitely sharpened my mind when it has come to this. It can be a challenge sometimes, but I've gotten better at this through consistent practice in new projects.


  1. Reliving the Past | ⭐⭐⭐⭐
    • This is something I do often and too much. I like to learn from my mistakes, but there's something to be said about overdoing it. Or better put, it helps to learn when it can be productive to reflect much on past where things didn't go the way you hoped. Sometimes it can be an opportunity to learn, but often there's elements of circumstance that you couldn't have changed regardless.
  2. Blame Yourself, Credit Others | ⭐
    • I've learned this early on in trying to combat depression. It helps to reward yourself often, especially for trying new things that you want to be good at. Crediting yourself is just as important as crediting others.
  3. Rehearse "3 bad things" Daily | 0
    • This is the opposite of a positive "3 good things" thinking technique where you recite 3 good things that happened to you at the end of each day.
    • There have been moments of dread in the distant past where I worried about soon-to-be-presents events, and the possible bad things that could happen. This really doesn't happen anymore. If anything, I keep looking toward future expected events that I want to happen.
  4. Imagine Future Hells | ⭐⭐⭐
    • This is the act of envisioning things that could go wrong for you. I feel like this lesson is double-edged sword here; it helps to think through painful worst-case scenarios to plan for contingencies down the road; on the other hand, doing it too much can pull yourself down for things that, more often than not, won't happen. There's a balancing act to learn here.
  5. Place Hope Over Action | 🚫
    • I'm more of an action-oriented sort of person when it comes to things so I've been lucky to avoid this one. 
  6. Be a Toxic Optimist | 🚫
    • "Toxic Optimist" gets defined as someone who's an optimist to the point of blinding themselves away from potentially catastrophic events, in other words, not being a realist. This is one thing I've been lucky to avoid and I've actually done the opposite (see #4 above). 
  7. Focus on Negativity | ⭐⭐
    • This one happens all the time, again, it's a part of worst-case scenario planning. I think my job causes this to happen often; part of programming is writing code that will execute consistently under the same, limited, set of inputs; in order to do that, you really need to filter for the negative, think of all possible situations where things will go wrong.
  8. Place Yourself Elsewhere | ⭐⭐⭐
    • Aloofness is a reoccurring trait of mine. My mind tends to drift a lot. Being present is something I've been working on for the last 3 years, but it's been an uphill battle. When I think about this, the term default mode network comes to mind. I think being in a world where everything is changing constantly causes the mind to drift into mode of thinking where you're constantly having to reassess everything you know, and thus wearing itself out.
  9. Insist on Perfection | ⭐⭐⭐⭐
    • Another thing I do too much. Rehearse, re-rehearsing, re-re-rehearsing, etc, is the only way to improve something. Finding that point of diminishing returns is easy to miss sometimes. Especially, if you like focusing in on all the small details like I do.
  10. Keep Working on Your Self-Esteem | 🚫
    • This is another lesson that falls into the category of focusing-directly-on-unhappiness is a sure way to stay in that mindset. This is another lesson I've learned not to do anymore. Plus, self-deprecating humor is funny sometimes and teaches you to not treat everything so seriously.


  1. Be a Lonely Island | ⭐
    • In other words, not spending time with other people. I think I've been aware of this for awhile, and I've actually been countervailing it in my recent life; living in a large metro area has sort been a bit of a culture-shock, having lived in a suburban environment for a good portion of my life; I've come to learn, and appreciate the value of being a part of different types of social groups. 
  2. Always Reflect What Others Tell You | ⭐⭐
    • In other words, being a people pleaser to the point of not telling others what you really think. This lesson is a general conversational skill that gets better with age, I think. Always reflecting back thoughts/beliefs in a conversation makes for a pretty boring time I've found; additionally, trying to always follow others' thoughts/beliefs without challenging them (especially if you feel strongly otherwise) is a good way to destroy your ego. Sometimes I do get overly diplomatic just for the sake of pointless argument.
  3. Compare Yourself Lower to Others | ⭐
    • This is one lesson that I've gotten better at with age. Everyone has a different set of abilities & skills that are the product of their background. You're always going to find someone that's "better than you" depending on how you frame it. Even if you are "the best" at some arbitrary metric you can create all kinds of hell for yourself trying to stay every vigilant to defend it.
  4. Always Compete | 🚫
    • The only thing I ever feel like I'm competitive at a perhaps trite things like video gaming. I can't think of anything else where I'm competitive to the point of being a toxic asshole. 
  5. Keep High Expectations of Others | 🚫
    • The only expectations I hold over others are the standards at which they present themselves to.  
  6. Have No Personal Boundaries | ⭐⭐⭐
    • Most of these lessons on the list are pretty self-evident if you've spent some time fighting against miserable. This one surprised me, but makes complete sense when taken to the extreme; trying to accommodate everyone is a good way to turn things miserable. 
    • I do this more often than not, unintentionally, because generally I'm looking to maintain a calm & easy-going attitude.
  7. Bond with Others' Potential, Not Reality | 🚫
    • This is presented in a relationship context, but I can see the general case here too. You can wear yourself out trying to focus only on the good side of person who doesn't want to change their toxic behaviors.
    • For me, I've only judged others by their potential (like someone who has wasted their opportunities in life), but not bonded. If I feel like someone should change their behavior, I try to let them know it. 
  8. Demand Loyalty (of Others) | 🚫
    • Yeah, I don't treat life like it's Game of Thrones.
  9. React to Motives, Instead of Messages | 🚫
    • I probably spent too much trying to think about people's statements so I can discern what I think/feel about what others say. I guess I've been around mostly good of people in my life, where I've not built up an inherent skepticism of others' motives.   
  10. Cultivate & Love Toxic Relationships | 🚫
    • I'm feel like I'm pretty lucky in life to have met and know the people I do. There's been only a few people in my life where I would describe the interactions as mostly "toxic". 


  1. Focus on the Small Picture | 🚫
    • Small picture thinking isn't really my thing. If anything, I'm probably the opposite, perhaps thinking a bit too much on the big picture (see Cultivating Your Presence).
  2. Always Follow Your Impulses | 🚫
    • I'm pretty much the anthesis of impulsivity.
  3. Focus Only on Yourself | ⭐⭐⭐
    • I rank myself up here, because I think, objectively, I'm less-than-average on the selflessness scale. Not that I'm selfish asshole, but rather I don't spend much time thinking about helping others. There are occasional situations where I've had agency to help out, but it's just not an emphatic skill that I routinely foster, which is, I believe, what's needed to really cultivate this.
  4. Chores Now, Life Later | ⭐⭐⭐
    • I've definitely been guilty of this often. It's easy for me to fall into a one-track mindset where I'll started blocking out the fun things happening around me, to my own detriment.
  5. Live to Others' Standards/Expectations | 🚫
    • I'm pretty luck to have had parents & peers that have no expectations of me other than being successful & happy in my own life pursuits. I can't think of any other close people in my life who set me to any standards/expectations of their own.
  6. Stay in Your Comfort Zone | ⭐⭐
    • I'd like to say I'm doing this less-than-often. "the only constant in life is change" is a mantra that has stuck with me for quite some time. If I was realistic, I say it occurs time-to-time.
  7. Avoid Solitude | 🚫
    • I enjoy my solitude and I've definitely recognized my limits of social time. 
  8. Follow Fashions, Don't Develop Your Own Style | 🚫
    • This is something that has gotten better with age. I'm comfortable with who I am, and learning what I'm not, while still willing to try new ways to present myself.
  9. Always Pursue Happiness | 🚫
    • As I've gotten older, I've recognized the futility in trying to force my feelings. Sometimes sadness happens; it's better to ride through it's courses than trying to force it away.
  10. Focus on Improving Yourself | ⭐
    • There's been times where I've been relentless in a pursuit to make myself "better" at times in life. I'll mark this as 1 star just because I'm doing this right now in this post. 


As mentioned, scoring was intentional to produce an easy score index. Each star represents a negative value that can be added up then multiplied by a constant to produce a simple 0-100% misery index. I've done this for each part to get a relative sense of which part of life is the most miserly, as well as an overall score. 

For each part, we multiply the cumulative rating values by -2%. For the overall score, we multiply the cumulative rating values by -0.5%

LIFESTYLE: 72% (14 x -2)
THINKING: 66% (17 x -2)
PEOPLE: 86% (7 x -2)
PURPOSE: 82% (9 x -2)
OVERALL: 76.5% (47 x -0.5)





Objectively looking at these results, I'd say they are pretty accurate. My manner of thinking is probably the worst for my own happiness; that horrible D+ rating is the result of worrying too much about past & future, with a negative outlook too focused on perfection, while not even being in the present sometimes. My lifestyle is an OK C-, that could be helped with a drastically reduction in screentime, work, & news consumption. I have a decent B- in purpose that could be raised with less obligations and more helping others when I can. Lastly, I have a solid B when it comes to personal relationships that could be helped by strongly defining my own boundaries and being more assertive on my opinions even if they cause dissonance.

Overall, happiness looks to be to be an OK C rating, that could be better. Improving my own thinking and lifestyle are the big targets, but there looks to be smaller improvements I can make for personal relationships & my own sense of purpose.

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