You Are Bad at Making Yourself Happy

Jane - 1997 in Cambridge - maudlin and idealistic youth

Jane - 1998 in Cambridge, England - maudlin and idealistic youth

My job as Writer’s Digest publisher often leads people to remark what a great life I have. So young, so accomplished, so happy!

Well, you know the old cliche about people who appear to be living the perfect, enviable life?

Right—well, I am thankful and lucky for what I have. I won’t go into the happiness question because as soon as you start to talk about it, it disappears.

But here’s the more interesting question: Is the life you lead the one you expected for yourself?

What if you knew that, at age 21, I envisioned this:

  • Working in Peace Corps
  • Getting a PhD and teaching/living abroad
  • Marrying a man I’d spend the rest of my life with

If this is what’s supposed to make me happy, then I’d be living a nightmare right now—divorced in the Midwest with a corporate job in publishing.

We all have idealistic (perhaps misguided) dreams in our teens and twenties. I was supposed to stay at F+W for about 2 years, then get on with my “real” life. Obviously something else happened.

So what happens when we end up on a path we didn’t envision for ourselves?

It’s a question that Victoria Zackheim asked and edited an anthology on: The Face in the Mirror. I highly recommend it.

Back to the happiness question. I read a book, Stumbling on Happiness, that made a convincing argument that humans are very poor judges of what will make us happy. Malcolm Gladwell sums up the book on its Amazon page:

What distinguishes us as human beings from other animals is our ability to predict the future–or rather, our interest in predicting the future. We spend a great deal of our waking life imagining what it would be like to be this way or that way, or to do this or that, or taste or buy or experience some state or feeling or thing. We do that for good reasons: it is what allows us to shape our life. And it is by trying to exert some control over our futures that we attempt to be happy. But by any objective measure, we are really bad at that predictive function. We’re terrible at knowing how we will feel a day or a month or year from now, and even worse at knowing what will and will not bring us that cherished happiness. Gilbert sets out to figure what that’s so: why we are so terrible at something that would seem to be so extraordinarily important?

In making his case, Gilbert walks us through a series of fascinating—and in some ways troubling—facts about the way our minds work. In particular, Gilbert is interested in delineating the shortcomings of imagination. We’re far too accepting of the conclusions of our imaginations. Our imaginations aren’t particularly imaginative. Our imaginations are really bad at telling us how we will think when the future finally comes. And our personal experiences aren’t nearly as good at correcting these errors as we might think.

And this in turn, reminds me of one of my favorite passages from Fear of Flying by Erica Jong:

I want, I want, I want, but you don’t know what you want or how to get it. You hardly know who you are. You go on instinct. And your instinct mostly pushes you toward adventures you won’t grasp until you look back on them. Life can only be understood backward, but it must be lived forward.

Finally: The Abandoned Dreams Depot

And finally-finally: The Riddle of Experience vs. Memory (amazing TED talk on happiness)

Posted in Life Philosophy, Reading, Work-Life.

Jane Friedman (@JaneFriedman) has 20 years of experience in the publishing industry, with expertise in digital media strategy for authors and publishers. She is the publisher of The Hot Sheet, the essential newsletter on the publishing industry for authors, and was named Publishing Commentator of the Year by Digital Book World in 2019.

In addition to being a columnist for Publishers Weekly, Jane is a professor with The Great Courses, which released her 24-lecture series, How to Publish Your Book. Her book for creative writers, The Business of Being a Writer (University of Chicago Press), received a starred review from Library Journal.

Jane speaks regularly at conferences and industry events such as BookExpo America, Digital Book World, and the AWP Conference, and has served on panels with the National Endowment for the Arts and the Creative Work Fund. Find out more.

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Christopher Gronlund

In high school, I thought I'd go into the Peace Corps…until I found out that you needed a degree. I thought I could go someplace other than where I was, help people, and be taught how to do cool things. I've found that I'm happiest when I do things I can do most days: going for walks and hikes, juggling (I've been a juggler for 28 years), enjoying a drink with my wife or friends. In fact, the happiest I am is when we have friends over for dinners. I'm happier on those evenings than I am when I see… Read more »

Patricia V. Davis

Great post, Jane.

dave malone

This is so powerful, Jane. And I think the Jong quote is amazing and really hits the truth. I think Alan Watts says it well too about the stream of life. We're all in it. And you can fight the stream, or you can just go with it. I think it's in that awareness, “Here is the stream of life. And I'm in it. No need to fight.” That's where the true adventures are, without agendas, a sort of Joseph Campbell, following a bliss, (doing what you love in the stream) and not fighting the flow. I read a quote… Read more »

Marisa Birns

I've spent so many years “looking” ahead at the end of the path, and thinking about how happy it will make me to reach it. Of course, there are forks in the path and sometimes I had to take different ones because the one I was on was blocked by something or other. I forgot, though, to look around and see where I was. And derive the happiness that comes from being in the moment and accepting all the good things I didn't appreciate because they weren't part of the “plan.” Having goals for the future is great. Not appreciating… Read more »


What? You quoted FOF! One of my all-time favorite books during my tragic twenties? Love that. 😀

You're making me think now. What did I envision at 21?

I'm not sure. I'd been sideswiped by a personal tragedy in college and was pretty much in full-on rebellion mode. So I ran away to Chicago with the biggest bad-ass I could find and didn't look back for seven years.

Not that I stayed with that one no-goodnik for seven years. There were plenty of other perfectly inappropriate men for me to choose from. 😉

Viva, late bloomers!

[…] my happiness post, I realized I didn’t comment on one of the key linchpins in happiness: […]

Jacki Welsh

Thanks for all the recommendations. You address a very interesting topic here, and I'm looking forward to reading more on the subject.

I'd have to agree with this, I'm bad at making myself happy. Terrible, in fact. The times I've really really been happy were those times I haven't expected to be happy at all! What's funny is that I sometimes try to replicate the same situation that made me happy, like a formula or a manual to follow. But it doesn't work. Happiness cannot be replicated, it can only be received one surprising moment at a time.

Bob Iozzia

So many/too many of us define ourselves by our jobs and stations in life. I don't care who or what you are, the reality can't measure up to the fantasy of who and what we want to be and think we deserve to be. Our definition of happiness is too frequently joined at the hip of this dilemma. I had fallen into this trap—when I gave up my life as a starving musician, I no longer had a creative outlet. I settled into and out of a lousy, brief (luckily) marriage, and then eventually into a fulfilling marriage that has… Read more »


We are bad at making ourselves happy because, first, we don't clearly understand what happiness is, and second, we don't know how to do it. Ultimately, every creature seeks pleasure, good feeling, happiness, or however we call it. Humans go about it in clueless ways. Most of us have lost touch with our inner selves, therefore we don't know what would make us happy. So we run around like headless chickens, trying to find what's lacking.How many of us respect scenarios that Life offers us? How many believe that maybe what we have is much better or more relevant for… Read more »