A reading list for the existential period of mid-life


Peter Sellers 1979 performance in “Being There”

Why the reading list?

After 40, a number of things start to give you a perspective on your own mortality that can be utterly terrifying if you’re not prepared for it, including:

  • You start to attend funerals more frequently.
  • You watch your parents and your kids age, each of which provides different kinds of frightening perspective on the finite nature of your own timeline.
  • Your career takes various twists and turns.  If you’re successful, you might think you’re working too hard and missing out.  If not, you might bemoan the fact that by now you feel you should have accomplished more.
  • You watch friends make spectacularly huge mistakes in their personal lives, which can cost them friends, family, health, security, and sadly sometimes their lives.

Into this mix comes a collection of books and resources that I have read that I have found useful in my own inner dialogue on the topic of life, meaning, and happiness.  Some of them are particularly cheesy, but all have contributed in some way to advancing my thoughts on this process, so I wanted to be helpful by documenting them.

Quick questions for people in crisis

Friends: “I feel like I don’t have any friends.  Or any good friends.   I sometimes feel like the friends I spend time with aren’t really my friends at all, or don’t really have my best interest at heart.”  Read: “10 types of odd friendships you’re probably a part of.

Happiness: “I feel like I’m less happy, even though I’m doing the same things.  Why do hobbies not thrill me like they used to?  The romance has left my relationship.  Work is not as fulfilling.”  Before ditching these things, you may want to learn a little science about how human brains create (and adjust to) happiness.   Read anything by Sonja Lyubomirsky, but start with “The Myth of Happiness

Work: “I’m not happy in my job.  Am I even in the right career?  Am I doing things that make my happy?”  A short, brilliant treatise on finding meaning in work and life was done by Hunter S. Thompson (“Tips for Finding Meaning In Life“) but a longer, deeper exercise can be found in the five questions posed in this exercise done at Harvard for their students, “How to live wisely“. I want to add that everything you’ve learned in life can predispose you positively to taking up an entirely new profession, but only if you’re willing to put in the work (see Malcom Gladwell, “Late Bloomers“).

Love, sex, and long-term relationships: “I miss the spark in my long term relationship.  What happened to the passion?  I want to feel that again.”  Watch this Ted talk video from Esther Perel, “The secret to desire in a long term relationship”, a NYC-based therapist who does a good job of describing the interplay of intimacy and passion in long-term relationships.  Then go read her book, “Mating in Captivity“.

The full bibliography (new items are added to the top of this list)

“Inside you there are two wolves” or “This is why you’re not happy”, selected quotes from Matthew McConaughey (YouTube video): I hesitated to post this because it’s a bunch of unrelated McConaughey quotes and it’s delivered in the “far out in left field” style that McConaughey is known for over a piano soundtrack and video clips added by an editor….

…but the thing is he’s absolutely right on a number of issues: finding joy in your work vs finding happiness and knowing the difference, defining success correctly, feeding your good intentions, studying how the choices you make change you, etc. Listen with a grain of salt and since McConaughey is what you get if you sobered up Gary Busey but kept all the weirdness, he’s actually notably insightful as the editor jumps around his body of spoken wisdom.

Your best professional working days are either ahead of you or behind you:

  • You’re done: “Your Professional Decline Is Coming (Much) Sooner Than You Think: Here’s how to make the most of it.” (The Atlantic): This article was much better (and much longer) than I thought it would be going in. There’s a lot to think about in here, but I think that the underlying research has issues. The prime evidence for this article is the author citing his own personal professional arc, which is fraught with observer bias.
  • Late Bloomers (New Yorker): Malcolm Gladwell surveys the research around when people hit their stride professionally and discovers that age isn’t that much of a factor. In fact the wisdom, maturity, and work ethic you’ve developed earlier in years can allow someone to take up a profession later in life and be surprisingly successful. Surprise, though, it’s still a ton of work.

She’s 103 and Just Ran the 100-Meter Dash. Her Life Advice? ‘Look for Magic Moments” (NYT): Asking for happiness advice from older people is like asking for a big dose of survivor bias (literally), but there’s always a few gems in these interviews.

Mating in Captivity” (Esther Perel): Why does passion fade in long term couples that are still in love with each other?  Dissatisfaction with one’s sex life is one of those things that hits you in midlife as you begin to start evaluating things.  Perel’s theory is that intimacy obliterates the distance between couples that is necessary for passion.  Her TED talk briefly explains this, but her book makes the strongest case and provides some direction about how to put that distance back in a relationship and reignite passion.  Her work on infidelity is interesting as well.

“The Tail End” (Wait But Why): Tim Urban perfectly nails the sense of perspective necessary to realize just how important it is to prioritize your life.  (If you’ve had cancer, you’ve already been through this thought process.)  He shows you that for many adults past college age, you’re in the tail end of many things, such as the final 5% of the time you’ll spend with your parents.  The final 5% of time spent with life long friends, etc.  The last 10% of your time with adult siblings.  For some good perspective, read it and make your own graphs.  (The blog Wait But Why is the only resource to make it twice into this list.   You should subscribe.)

What makes a good life?  Lessons from the longest study on happiness” (Ted Talk): Robert Waldinger is the fourth director of a 75 year long study, the Harvard Study of Adult Development.  The study has tracked 724 men for 75 years asking them about their work, their home lives, and their health.   60 of the original men are still alive and participating, providing data at the ends of their lives.  I recommend you read the transcript rather than wade through the video if you are pressed for time.  TLDR; People with strong interpersonal relationships are happier (quality not quantity), loneliness is toxic to both your mental and physical health, a successful career is not replacement for personal relationships, and drama free romantic connections are better for your long term health than tumultuous ones.  Most importantly, The people who were the most satisfied in their relationships at age 50 were the healthiest at age 80.”

4 Rituals that will make you happy, according to neuroscience” (Time): Neuroscientsts know there are specific actions we can take that increase certain chemical levels in your brain that make you happy.  This article excerpts a number of new books about rituals that activate parts of the brain that produce those chemicals.

How to live wisely” (NYT, Richard Light, Harvard Graduate School): This is the most cogent and concise method for evaluating your life I’ve ever seen.   The five questions you answer in order to evaluate your life (and tune it) are part of a noncredit course at Harvard called “Reflecting on your life“.

I asked atheists how they find meaning in a purposeless universe” (Buzzfeed): It’s a Buzzfeed article without numbered lists, which in an of itself is great.   But for those who doubt (or actively disbelieve) in one or more gods, there’s a lot of great thinking in here.

Daytripper, graphic novel by Fabio Moon and Gabriel Ba: This well-executed graphic novel explores a dozen or more branches of a man’s life, where he dies at many different ages: 8, 18, 28, 32, 48, and so on.  It lays out as a meditation on death, it’s role in finding meaning in life, and how not to miss the value of what’s in front of you.    It’s a substantive read without being heavy-handed or preachy.

The Power of Good Enough” (The Atlantic by Olga Khazan): Unless you’ve renounced your worldly possessions, acquiring stuff is something that happens, and therefore also a certain amount of “Buyer’s Remorse”.   The article touches on a book that covers the differences between people who hunt for the perfect product for them (“maximizers”) and those who settle for things that are good enough (“satisficers”) [sic].  Purported research (not cited) says that satisficers are happier than maximizers.  In general, the concept of “enough” comes up a lot in happiness research, with the ability to be satisfied with enough a key factor in happiness.

Tips for finding meaning in life” (Hunter S. Thompson): The great Gonzo has some intelligent things to say about finding your own path.

“In search of lost time: Why is everyone so busy?” (The Economist): A great read if you’re well-employed, busy, and starting to play ways to improve your work life balance.  This long-read reviews the data on leisure time, both from a measured and self-perception point of view, and combines it with data about hours worked usually associated with the labor market.  It helps explain some of the modern cultural workplace phenomena such as “face time, does it really make me more money?” and the “having it all” struggle” working women go through.

10 types of odd friendships you’re probably a part of (Wait But Why): Why is it so hard to make friends after college?  Why do I feel like I don’t see my friends enough even though I’m always going out and my calendar is full?   This brilliant article explains the mish mash you end up with post-college of friends, how to differentiate the different types, and the various traps you fall into.

“Candyland and the Nature of the Absurd” (Existential Comics): Don’t try and take solace in either Sartre or Camus during the midlife crisis process.   But read this comic because it’s funnier than it is depressing.

The Real Roots of Midlife Crisis” (The Atlantic): An excellent read about scientists in multiple, separate places trying to understand a puzzling pattern of unhappiness in midlife that keeps recurring in their happiness research data, and how likely you are to be happy at 27, 47, and 67.  TL;DR: In midlife you suddenly see both your birth (your kids) and your death (your parents) at the same time, and it gives you a healthy perspective on life you did not fucking want.

The Dalai Lama’s Ski Trip: What I learned in the slush with His Holiness” (Slate article): A waitress asks the Dalai Lama “What is the meaning of life?”   Despite it’s brevity, I found this to be a very useful article.

Man’s Search for Meaning” (Viktor Frankl): Viktor Frankl survived the concentration camps of World War 2.  He draws a line between what he saw in the camps and how we can have a more healthy relationship with the concept of suffering.  While helpful, I find it difficult to extrapolate too much from his concentration camp experiences, in the same way that lawyers argue that “hard cases make bad laws.”

“The Myth of Happiness” (Sonja Lyubomirsky): If you’re wondering, “Is there a researcher out there who runs studies of happiness and then translates those results into mass market paperbacks?”, the answer is yes, and her name is Sonja Lyubomirsky.  Her book The Myth of Happiness is exactly what you’re looking for when you wonder, “Why does my long term relationship not make me as happy anymore?” or “Should I change careers?  I don’t feel as rewarded by my job as I used to.”

“The Book: On The Taboo Against Knowing Who You Are” (Alan Watts): This is a fairly dense text on the nature of self, non-self, and the fallacy of the separation between them.  It doesn’t veer into crazy hippie claims about “energy”, but resembles classic philosophy texts that reason their way through issues of perception, self, and the nature of being.  It is not without its flaws through.  Broad generalizations about religion will prove to be annoying.   I think the first chapter is probably the best, and you would be excused for putting it down after that.  Previous readers of Huxley, McKenna, or Leary will be completely at home in Watts’ work.  As an aside, Alan Watts is a national treasure that I hope is rediscovered by every generation in the future.  His ability to lead a serious discussion of identity and self without resorting to many of the bizarre and unsubstantiated metaphysical claims of his contemporaries makes his work uniquely valuable and timeless.

“The Myth of Sisyphus” (Albert Camus): Camus’ famous discussion of the validity of the choice of suicide as a rational response to existential despair.  I found this essay unreadable except by my 25 year old self who was in the middle Philosophy minor at Purdue.  My 47 year old self did not finish it.

“Give me gratitude or give me debt” (Glenn Doyle Melton): Melton’s essay is a much more entertaining and longer version of my personal slogan (“Any three of these is the Life Trifecta: a roof, a job, food, health, or love.”) that often comforts me when I lose perspective.  It’s a quick, satisfying read.

How the other half works: adventures in the low status of software engineers” (Michael O. Church): The link to this piece is contributed by an anonymous friend re-constructing his career in mid-life.  He has been an engineer historically and has occasionally suffered at the hands of a less-than-competent manager.   This piece is about someone re-contextualizing a software engineering career as management-grade.

Last letters from the dying

Periodically someone will realize they’re going to die (sooner rather than eventually, as we all do) and write a profound letter that circulates on social media.  I find these not always particularly helpful, but I’ve collected some where anyway.

Powerful advice from a dying man (Reddit): A 24 year old with terminal cancer provides advice for others on a life he will never get to lead.