I decided to write this guide because I have been pretty happy recently. I would go as far as to say that I am the happiest I’ve ever been (in a sustained way) in my adult life, and completely independent of my external circumstances. This is how I’ve done it.
In our society today it is easy to get caught on the hedonic treadmill: the belief that happiness is just around the corner if one can only achieve the next milestone, or experience the next life experience. This is a trap. As someone who has achieved more and more success over time, and experienced more and more fun, positive, exciting things, no achievement or experience has ever resulted in a sustained increase to baseline happiness for me.
Expectations for how you will feel once you achieve your goal lead to an endless cycle of suffering. Either you get what you want and then set new, higher, loftier goals, or you don’t get what you want and end up feeling miserable. In The Score Takes Care of Itself, Bill Walsh tells of winning three Super Bowls in ten years, only to quit at the height of success because victories felt like they didn’t count any more.
Because of my observations during achievement phases, I used to believe that it was impossible to change your baseline happiness: that each of us has a certain level of happiness he or she was born with, and after momentary spikes up or down we will always revert to the mean. In the past year I’ve reversed my thinking, as doing the following things has collectively improved my happiness.
Note: I started off as a beginner in each of these areas, and personally have relatively low willpower. The following things aren’t very hard to do, they just require repetition, consistent reminders, and practice.
Forming Good Habits
The key to staying consistent with all of my practices has been creating regular habits out of all of them. There are two strategies that have worked for me to form habits:
- The Seinfeld Strategy: using a habit tracker app for all of my habits, and just trying to create the longest unbroken streak possible. I am currently at 530 days of meditation in a row as of this writing. Some days it’s been 11pm and I really don’t want to meditate, but I do it anyways because if I don’t I’ll ruin my streak.
- Social accountability: I often make pacts with friends to do something consistently, and then we hold each other accountable. Not wanting to let yourself down is motivating, but using our inherent need not let others down is extra motivating.
In order to help myself and others form healthy habits, some friends of mine and I created Kin: Social Habit Tracker, a free app that lets you share your habit progress with friends. I’ve been using it myself for months now and found it has been helpful for myself and others in creating a positive feedback loop around doing the positive things I want to do in my life.
I also recommend reading James Clear’s excellent Atomic Habits as a practical guide to habit formation.
Five Minute Journal
I started off using The Five Minute Journal, a simple app that asks you every morning to name three things you are grateful for, as well as three things you are going to do to make that day great, and the positive affirmations you have for yourself that day.
Explicit gratitude is important because it helps re-contextualize the short term negative things that happen to you throughout the day in the greater context of all the positives in your life.
The good thing about the journal is that it really just takes five minutes a day. My recommendation is that you commit to it for a week (that is only a commitment of 35 minutes) and then see if you feel better.
After using the journal app for six months, I decided to create a gratitude master list, which is basically a google doc listing out all the things I was grateful for (I thought of 58), all the lucky breaks I’ve gotten to get where I am, and what the Justin of 1, 2, 5, 10, 15 and 20 years ago would have thought if he knew where I am now. I try to look at this list occasionally for additional re-contextualization of my present state.
One Stoic practice I’ve adopted is negative visualization, the practice of imagining (with as much detail as possible), what your life would be like if something bad happened to you. What if you got cancer? What if you became paralyzed? What if your company fell apart and you had to get a job?
By imagining the worst case scenarios very vividly, two things happen. First, you realize that you would adapt to them: the human mind and body are very adaptable and people have adapted to far worse things that you have or will likely ever experience. Second, when you are done you will wake up in your real life and realize how awesome it is.
I am pretty new to meditation. I started off using Headspace, which worked reasonably well to create a sense of calm for me throughout the day. After a couple of months, I would do focused meditation following my breath (on average once every other day) for about ten minutes.
I am now doing Transcendental Meditation (TM), which Ray Dalio recommends in Principles: Life and Work. TM is a form of mantra meditation that is quite easy to adopt, that you do in two 20 minute daily sessions (I do them right when I wake up, and then in a supply closet at work in the afternoon). While this is a big time commitment, I feel like it has paid dividends to my daily happiness, energy, and ability to be present (note: it is hard to disaggregate this effect from the other things I am doing).
There is a TM center in San Francisco and in Palo Alto that you can go to where they will teach you, or I can recommend a teacher to you.
One tactic that has worked well to keep my meditation practice consistent is to use a streak tracking timer to track my daily meditations. I use Insight Timer to track the 20 minute sessions, and every time I run the timer Insight Timer will automatically add to my streak of how many days in a row I’ve meditated. At this point, I’m so invested in keeping my streak alive (and not starting over from zero) that I refuse to miss my meditations every day.
You have voluntarily decided to carry around a toxic, time-wasting Skinner-box in your pocket at all times, from the second you wake up in the morning to right before you fall asleep at night. This is incredibly stupid, and yet every smart person does it.
After turning on Screen Time, I realized I was spending 5.5 hours a day on my phone. Even worse, I self justified this by saying that some of it was work (email and Slack), even though a large portion wasn’t (Twitch, YouTube, Instagram, etc). Last year, I finally decided I needed to kick the habit, and that even the work related things could be contained to times when I’m on my laptop without productivity really suffering.
I tried to go phoneless, and replace my phone with an Apple Watch, but unfortunately I still wanted to use some utility apps like Uber and Venmo.
The solution I’ve settled on is that I’ve turned my phone to greyscale (to reduce its addictiveness; go to Color Filters in Settings), deleted email, Slack, and all entertainment apps (YouTube, Twitch, Instagram, and even the browser), deleted the app store (locking it with a passcode that I don’t have access to).
My phone is now only useful for reading, music, texting; I find myself using it much, much less, at basically no cost to my quality of life.
Exercise and Diet
I try to exercise every day, even if it is just five minutes of crunches or push ups. In order to hold myself accountable, I have a trainer who shows up at my house 3x a week (I built a small gym in my garage). If you can’t afford a trainer, I suggest committing to meet a friend at the gym on a regular schedule: a social commitment will further obligate you to go to the gym, and remove it from being an active decision that you need willpower to make.
Since tracking my meditations through Insight Timer worked so well keeping me compliant, I started tracking my workouts through Kin. I’ve found that trying to keep the streak alive of working out every day has kept me motivated to at least do the bare minimum workout, even if I need to do it in the office!
I started experimenting with diets last year as well, after discovering that I was particularly sensitive to carbohydrates. For the first six months of 2018, I tried to stick to eating a ketogenic diet (this is a good guide to keto), which worked well to increase alertness and reduce fatigue throughout the day, but was hard to keep to. For the second six months, I tried intermittent fasting (IF) and eating only one meal a day during the weekdays (dinner), and eating whatever I wanted for that meal. YMMV, IF seemed easier to stick to and had about 65% of the benefits of keto.
I also quit drinking this year. My entire life I’ve used alcohol as a way to escape from negative emotions I’ve felt. Recently, I’ve felt that this has prevented me from understanding the full nature of my consciousness (as well as making it difficult to work out every day), and I decided to make a change.
I used the Kin to add a “Didn’t Drink Alcohol” today task, which has helped me stay compliant. I also created this Telegram support group for people who want to join me in being alcohol-free here that you can join.
I was very resistant to trying therapy. Finally, after a breaking point at a previous company, I realized I had to make a change and found someone. This was life-changing for me: I worked through a lot of paralyzing guilt around failure that I felt, and learned how to detach myself from my daily emotional ups and downs. I still see someone (different) today.
I think therapy fundamentally works because it is cathartic to talk to other people about your problems. Unfortunately, many people don’t have a close, impartial person they can talk to: therapy simulates this by making it someone else’s job.
If you are new to therapy, I recommend that you talk to a couple of therapists before picking someone. You want to find someone you vibe with, who you feel you can learn from and that you respect. That might take a few tries.
I try to actively remind myself that attachment to outcomes (future successes, or even things staying the same as they are now) will only cause my own suffering. Of course, this is very hard to actively hold in your mind.
The truth is that one day we will all lose everything we have, will ever have, love, and will ever love. Your friends and family will grow old and die, your fame will be forgotten, your health will fail, and eventually you will die. That might seem scary or sad, but it’s not!
The sooner you accept that life is change and that you can’t control the outcomes, the freer you will be. This is difficult to do in practice, and I am a relative novice in all these things; what I try to do is to regularly remind myself that I am going to die and in the greater context of the universe, none of the outcomes I want to happen really matter.
So why bother at all? I think about life and success like playing a board game on a rainy Saturday afternoon. When you are playing the game, you want to play by the rules (live a moral life), and you want to do your best to win (do well, be successful). But after the game is over, you will put it away in the box, and a few hours later you probably won’t even remember or care who won. That’s like life: you will die and it won’t matter afterwards but while you are playing you try to live a good life anyways because those are the rules of the game that are hardwired into humans. Just don’t get too bent out of shape while playing!
In an effort to connect in a more deep and authentic way with people around me, I’ve started to try to tell people more of the positive emotions I feel towards them. This applies both in life and in work. In today’s society, we are often afraid to say what we truly feel: we find it awkward, we are scared about how other people will react, or we don’t think it is appropriate. This is very unfortunate because it shallows out our connections with those around us.
For my friends, I have tried to find times to tell them the positive qualities that I appreciate about them, even if I feel awkward about it. I will literally say things like:
“I just wanted to tell you that I appreciate your friendship, and I’ve always admired that you are someone who connects well with other people as that is something I’ve always aspired to myself.”
At work, it might be something like:
“I wanted to tell you I appreciate your willingness to give me constructive criticism; I know it is not always easy to honestly criticize the CEO. I think that takes guts and it has helped me improve.”
The responses I’ve received have been surprisingly positive. Instead of being awkward as I’d feared, my friends and relationships have expressed gratitude for these authentic sentiments (ironically, because as a society we are collectively scared to express how we feel, authentic connection can be a very rare treat for people).
Of course, when you do this, it is important that you are actually authentic and not just blowing smoke up your friend’s ass.
Feeling and Naming Emotions
I have been incredibly fortunate to have amazing coaches and mentors in my life that have helped me on my self-growth journey. One very impactful program that I’ve experienced is Leaders In Tech (founded by Carole Robin and Joe Greenstein). Leaders in Tech is a T-group program, focused on building a learning group where you can test your mental models and develop your understanding of your own emotions. Going through the program helped me learn about being vulnerable with others and how to get in touch with my own emotions. I recommend joining a T-group if the opportunity ever presents itself, as it was one of the highest impact learning experiences I’ve had in my life.
The big realization for me was that emotions (anger, sadness, fear, joy, excitement) are just a signal. Emotions are neither good nor bad; they are just a form of data. Unfortunately, from a young age we are socialized to suppress the emotions considered “bad” (anger, sadness, fear), in both our work and life. Ironically, by doing this we don’t let them pass through the body, and instead they linger and become long-lasting moods.
I’ve become committed to feeling all my emotions (and not trying to avoid them through escapes like drinking alcohol or distracting myself through media). Also, I’ve tried to develop the skill of being able to name those emotions explicitly with myself and other people (“I feel anger right now”) as a way to drive more deeply into the underlying interpersonal issues (“I think this may be because I don’t feel heard by you in this conversation”). This was very scary to do when I was first starting out (generally we are afraid that talking about our “bad” emotions might cause others around us to withdraw their approval), but has really helped me connect more deeply and authentically with people around me, both at work and at home.
Since the evolution of mankind, 100 billion human beings have walked the Earth. If you are reading this, you are likely in the top 1% by any measure: opportunity, security, happiness. In fact, you might be in the top 0.1% or even 0.01%. What incredible good fortune. What an amazing opportunity. You are truly among the blessed.
I love you and I wish you the best,
Postscript: If you are interested in joining a community to help support each other in implementing these practices in our lives, I have created a Telegram chat group for this purpose here. Please join us!
Additional Reading List
The Untethered Soul, Michael Singer.
Amazing adaptation of Buddhist philosophy for a Western audience. This book was very impactful in helping me realize that I am not the events that happen to me, nor am I the emotions I feel or even my thoughts: I am just the observer of those things.
Leadership and Self Deception
Helped me understand how starting with empathy was critically important for improving my relationships (at work or otherwise) and also allowing me to accept my share of the blame when a situation is going bad.
The 15 Commitments of Conscious Leadership
This book has helped me figure out how to change my work life. By embracing Conscious Leadership, I’ve become more curious (“What is the universe teaching me at this moment?”) and more in touch with my emotions and comfortable naming them at work. It has been night and day for my team.