Skip to content

How Do You Pursue Happiness?

Be honest. Nobody’s listening. How happy are you?


If you’re a person so motivated by empathy that you’ve had no choice but to devote your life to easing the suffering of others, or if you’re one of those constitutionally easygoing people who came out of the womb radiating goodwill, then probably this is not the post for you. Likewise if you were born into war and/or extreme poverty in a miserable corner of the world from which there’s little chance of escape. Not that you’d be reading this anyway, but if you were, it would probably only annoy you.

I’m writing for people who, like me, are living and working in relative material comfort in this early part of the 21st century. People who were brought up with the belief that happiness is a thing you can and ought to pursue. And people who would not, in spite of a lot of education and opportunity, answer the question, “Are you happy?” with an unqualified, “Yes.” And while I’m not going to attempt a definition of happiness in a blog post, what I’m talking about isn’t simple contentment or a state of excited distraction like being drunk at a nightclub. I’m talking about an abiding sense of satisfaction with your life choices, your relationships, who you are as a person, and how things, overall, are going.

Be honest. Nobody’s listening. How happy are you?

If the answer is anything less than, say 70 percent, I’d say we’ve got a problem to address. Life is finite. I don’t believe in souls or gods (in spite of having spent a lot of time reading and thinking about them). And both nihilism and #YOLO strike me as lizard-brain responses to mortality. In spite of being finite, life and humans are complex and interconnected, and working toward the kind of happiness that will nourish others by extension seems like the only sane alternative to suicide.

But how do you pursue happiness? If you’re like me, you think, write, read, and talk about it until you’re blue in the face. Then you start making lists of the things that naturally make you happy in life and work. Then you try to do more of those things. Then you commit yourself to so many of those things that you become overwhelmed and unhappy. Then you try to get “back to basics.”

One of the few substantial longitudinal studies of happiness that has ever been done was the Harvard Grant study, initiated back in 1938 and still ongoing today. The limitations of the study are well-known and have been thoroughly criticized elsewhere: Its subjects were mostly socioeconomically privileged, and all white and male. Fair enough. But these weren’t robots, either — they were individuals with careers, relationships, and aspirations. Some ended up wealthy, some in poverty. Some suffered terrible mental or physical ailments, including drinking themselves to death. And many experienced years — or a full lifetime — of unhappiness. But among those who called themselves truly happy at any point in their lives, two factors were near-universal: good relationships and work they loved (regardless of how wealthy it made them, or didn’t). To that, Daniel Kahneman, the Nobel Laureate cognitive psychologist and behavioral economist, might add that even with good relationships and a job you love, extreme poverty will make you pretty miserable too. As will extreme wealth.

Bertrand Russell, in his magnificent, accessible, often hilarious 1930 classic The Conquest of Happiness (can more brilliant philosophers write self-help books, please?) starts by analyzing the root causes of our unhappiness. Mostly, he claims, they come from a modern state of affairs (even more true now, perhaps, than it was then) in which everyone rushes around all the time complaining about how busy they are. If you are surprised that this was an issue back in 1930, consider this quotation from Roman emperor and stoic philosopher Marcus Aurelius, written sometime in the second century, CE, in a list of the most valuable things others had taught him:

“Alexander the Platonist cautioned me against frequent use of the words ‘I am too busy’ in speech or correspondence, except in cases of real necessity; saying that no one ought to shirk the obligations due to society on the excuse of urgent affairs.”

And Marcus was in charge of an empire.

Russell argues that we fill up our lives with more or less meaningless activity as a way to mask deeper insecurities we don’t want to face. At root, maybe, the fact that we’re mortal, but above that more mundane things like the fact that our job sucks or we’re unhappy at home.

Modern urban life, with its endless distractions and financial pressures, encourages this state of affairs. The self-imposed busyness then makes us anxious and irritable, which drives us to more distraction in the form of a stiff drink after work, hours of Candy Crush Saga, Facebook, etc.

To make matters worse, Russell says, when we’re not busy solving the problems that keep us so busy, we’re busy worrying about them, all at once and without sufficient clarity of mind or focus to solve even one of them: 

“It is amazing how much both happiness and efficiency can be increased by the cultivation of an orderly mind, which thinks about a matter adequately at the right time, rather than inadequately at all times.”

I don’t know about you, but when I’m busier than I ought to be, I have abstract dreams of perseveration. I’m trying to do something ridiculous, and can’t get it done. In the most recent one, I was at the airport in some city far from home. I had parked my car and was nearly at the gate for my flight. And my flight was about to leave! Then I realized that I had failed to take note of my parking space and hadn’t given the keys to the person who runs the special service that will fly my car back home to me. I tried to get back to the car, but was afraid I would miss my flight. Also, I couldn’t remember how the service worked, exactly.

After such dreams I wake up at some ridiculous hour like 3 in the morning in a state of terror. The obligations swirl around in my mind, but there’s no way I can get it together to start working that early. In the past, that was it: I was up for the rest of the night and ruined for the day ahead. These days (thanks to about a year spent meditating regularly) I’m usually able to focus on breathing and calm myself back to sleep.

Invariably the cause of this situation is that I’ve gotten myself into something at work that doesn’t make sense, or I’ve turned something someone has asked me to do into a much bigger deal than it needs to be because it doesn’t make sense to me, and I’m pissed off that I have to do it. The solution Russell suggests (and the only thing I’ve ever found that works) is calming down, staring the thing directly in the face, and realizing it’s not so important in the scheme of things, after all. And neither are you:

“Our doings are not so important as we naturally suppose; our successes and failures do not after all matter very much.”

From college graduation until maybe my mid-30s, I was not a happy camper at all. For one thing, I was intensely focused all the time on my career, without the insight or the presence of mind to do anything about it. I knew I was “creative” and also “intellectual,” but I wasn’t sure what I should be creating or thinking about. Between 1994 and 2009, I did the following things in the following order:

  1. Went to graduate school in Santa Fe for “Eastern Classics,” the “great books” of India, China, and Japan.

  2. Flirted with conversion to some kind of modern Orthodox Judaism, and went to Jerusalem to start a second master’s degree in Ancient Hebrew and Biblical Studies.

  3. Quit that program after six months to move back in with my parents in Maryland.

  4. Co-founded a theater company in Washington, DC, then quit it after directing one successful production.

  5. Moved back to New York (where I’d gone to college) and spent six months recording a solo singer-songwriter album on my computer.

  6. Came very, very close to moving to Japan to teach English for two years (I signed the contract, then tore it up).

  7. Taught middle school English for three years.

  8. Wrote a bunch of children’s books for educational publishing companies in Korea.

  9. Taught community college English for two years.

  10. Got a second master’s degree in Developmental Psychology.

    But what of the relationships? If, as the Grant study found, good relationships are the single most important factor in determining overall happiness, what was I doing about those? As you might imagine, I was a weird dude, relationship wise. I did not go out of my way to meet people and spent most of my off-time reading or journaling or fretting about my non-career. In both friendship and romance, I was a one-person-at-a-time kind of guy. And I probably devoted most of this one-on-one time to complaining about my inability to figure out what I ought to do for a living. In other words, being a fairly crappy friend.

    After tracing the causes of unhappiness in the first half of the book (envy’s the other big one), Russell says it flat-out:

    “Fundamental happiness depends more than anything else upon what may be called a friendly interest in persons and things.”

    This “friendly interest” is deceptively simple. Russell means a kind of warm, scientific curiosity, not raw vulnerability. He doesn’t advocate letting other people emotionally destroy you. This is the curiosity of a person comfortable in her own skin and prepared, therefore, to meet weirdness with interest and compassion up to the point where polite retreat is necessary, which it almost never really is.

    For me, the boundaries of self and other have always been way too permeable. An intense vulnerability to other people’s emotions and demands makes me defensive and paranoid. If I let new people in, they’ll want things from me. They’ll make me feel guilty and bad about myself for having failed to meet their expectations. Much safer, then, to turn inward to writing or outward to books that allow you to slip into other people’s consciousness without fear of them slipping back into yours.

    Russell says that this position of “friendly interest” is only possible for someone who is free of the demons of anxiety and envy, a freedom granted either by your constitution or earned through hard work. But what if you’ve done years of what feels like hard work and still the weasels thrash about in the fighting-weasel pit of your brain, albeit somewhat more transparently than they once did?

    In my 20s, the pursuit of happiness was a zero-sum game. A lifetime of happiness or misery seemed to hinge upon every cover letter, every party, every conversation with a potential “connection.” When the claustrophobia and isolation would become too intense, my approach was always to dive headlong into the discomfort, hurling myself into the situations that terrified me the most. Auditions. Parties full of strangers. A year spent volunteering at a community outreach theater working with urban kids whose lives and culture I didn’t understand at all. I treated these kamikaze acts as a kind of cognitive behavioral therapy that was supposed to smash through my shell and change me from the outside in. Embrace your fear! Leap off the cliff! I must have metabolized at least some of this forced experience. Soldiers in wartime must gain knowledge and bits of wisdom, too, but PTSD comes along with them. They expand their horizons and narrow them simultaneously. In the end, the arithmetic doesn’t really work out.

    Smarter faster: the Big Think newsletter
    Subscribe for counterintuitive, surprising, and impactful stories delivered to your inbox every Thursday

    Russell’s right, I think. You need to be secure, at least to a certain degree, before venturing forth. Otherwise you just end up confirming your own worst hypotheses.

    If you’re not blessed with ease, joy, and natural warmth, or if early life deprives you of them, the only thing you know how to do is to keep moving. Keep pushing. Keep trying within and at the fringes of what your limitations will allow until something gives and a little light breaks through. And whenever it does, to the best of your abilities, you seize upon that thing and run with it.

    But the pursuit of happiness is mostly an uphill battle until you’re able to appreciate and find some measure of happiness in the things you already have. Your own positive qualities. The people who love you in spite of everything that’s wrong with you. The people you love, once you’re brave enough to stick your head far enough above ground to see beyond yourself. For me, only time has made that even remotely possible. And once you’re there, even a little bit, the pursuit of happiness becomes something less a pursuit in the sense of chasing something unattainable, and more a pursuit like gardening. You shuffle out, bleary-eyed, into the sunshine and look around, blinking. You notice something that needs watering. Something else that needs trimming. You take pleasure in the things that are flourishing. It’s a feedback loop like the mild PTSD I described before, but one that reinforces and expands your potential for feeling and creating happiness, even when faced with the worst horrors life has to offer.

    Happiness, then, isn’t about feeling ecstatic all the time or floating, untroubled, on a calm, open sea. It’s not about finally reaching some point beyond disappointment and pain. However imperfect you still are, it’s about knowing you’ve got the power to make things better, putting that power to use, and being able to enjoy the results.

    Talk to @jgots on Twitter.

  11. Related

    Up Next
    New technology will surely improve the lives of older adults. However, there is a secondary effect of today’s technological innovation — it raises our expectations for life tomorrow. Technology is teaching baby boomers and every generation that follows to expect more and better in older age.