Live Your Pretty Good Life

Lee Howard,

I admire Oprah Winfrey. She’s got the most triumphant rags-to-riches story ever, she proved that TV talks shows could be more than lurid schlock (but think twice before you accept the free car), she’s brought inspiration and Eckhart Tolle to millions, and she’s a terrific actress.

The Color Purple, 1985

A Wrinkle In Time, 2018

I used to subscribe to O, her magazine. I loved the combo of earnest, positive-thinking idealism and unapologetic commercialism, and I’m a big Martha Beck fan. Every month for years I read the mag from cover to cover, ogling the clothes, taking voyeuristic pleasure in Dr. Phil’s script for the relationally befuddled, and deriving inspiration from the spiritual pep talks that sprinkle O‘s pages.

But O is a big dang magazine. Over time, its back issues started to weigh down my coffee table. And gradually, I recognized that the oft-repeated admonitions to live your best life were beginning to weigh down my spirits as well.

Don’t get me wrong. I get that positive thinking is way better than negative thinking, and that life is meant to be more than a succession of maintenance activities. And whether or not you believe that our thoughts create our reality, they sure do determine our experience of it, so it’s a good idea to stay focused on the bright side. Moreover we all need to shine our own lights into the universe. All good stuff.

The problem with the live-your-best-life mantra is that it leads to keeping score, to grading our lives as if they were term papers. This is when the ego kicks into high gear. On one level or another, we’re either worse than or better than pretty much everybody else. So we vacillate between feeling superior and inferior.

What if, we fret, we are not living our best life? What if we’re not all that special? What if we are, when rated on some vast invisible scale, just okay? And how do we know how well we’re doing at life, unless we keep anxiously comparing ourselves to others?

I had my kids in the 1980’s, at the height of the obsession with children’s self-esteem. This was when we were constantly telling our progeny how unique and wonderful they were. Which is lovely — every kid should get to feel special sometimes — but we left out the other half of the equation.

If everybody is special, then it follows that we’re all also just, well, regular folks. Meanwhile, life, however we evaluate it,  is composed of a succession of moments, some of which are wondrous, some of which are terrible, and most of which are utterly ordinary. If we want a shot at being happy, seems to me the key is to embrace that reality.

As for where we fit in on the scale of wonderfulness or lack thereof? I’ve heard this teaching ascribed to both Judaism and Buddhism, but this is a thought I find helpful: picture yourself putting a slip of paper into your right pocket and another into your left pocket. On one paper is written the words “for me the world was created,” and on the other, “I am nothing but dust and ashes.” Both statements are true, and as you stand in the center of them you will find yourself in balance.

You may actually be living your best life today. Or perhaps at the moment your life rather sucks. In either case, it will change, so relax. We will all get to the finish line, no matter what. Meanwhile, do the best you can. But lighten up about it, for heaven’s sake: you’re fine as you are.

I wish you many blessedly ordinary moments — and as always, your comments are special to me, in the best sense of the word, so please chime in!


  1. This is so true. I think the key to getting through your life is to find a way to laugh about the dull and ordinary things and even the tough times. I try to find some fun in my daily life because it helps balance out the challenges. And we all have them and some of them are terrible.

    I think the “you are so great” way of raising children carried over into the nineties and is still very much a part of raising children today. In the beginning, I used to buy into that, but now that my kids are older, I see the problems it can create once they enter the real world. Better to keep them grounded and not give out a medal every time they do their homework.

    Great post – I’m a believer in making your own happiness, but you are right, let’s not keep score.

  2. I’ll bet most honest parents will admit to having had to do a course correction at least once along the way while raising their kids — I sure did! But you know what, I think they’re pretty great anyway 😉

    Glad you like the post, and thanks!

  3. As usual,your comments are insightful and beautifully stated. I am transitioning into retirement and these sentiments are helpful for adjusting to new goals Thank you.

  4. What a wonderful post! Just what I needed to hear. I was having a conversation with a friend about this one time, and she asked me if I was “living my best life”. I told her that I wanted to “live the life that is right for me”. I think there is a subtle, but important difference.

  5. Whenever I start to assess “where I’m at,” I remind myself that I am lucky just to be alive. There have been more than a few close calls in my life that I survived, and a few health crises that threatened me with a shorter life than I could ever have imagined. Remembering that my stated goal for 2017 was “No trips to the Emergency Room” (which was achieved!) keeps me grateful, with a balanced perspective about my life and my “now.” Thanks for sharing YOUR perspective! ❤️

  6. Great post, Jan! Glad I am not the only one who feels this way! It goes hand in hand with current admonitions to always be unique. It seems if you’re not doing everything you can to stand out from the crowd, then why bother.

  7. I agree with everything you said 100% – which must prove you’re correct, right? Oh, and wise! From the O Magazine trajectory (including piled up back issues, love of Martha Beck and then noticing the repetiveness of the topics addressed) to the two pockets/two slips of paper. And being unsettled that “living your best life” seemed to turn into a questioning recrimination rather than a constructive cheer. You have a clear eye, my friend, and you state it all very well. Keep up the good work.

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