The Slow and Certain Heartbreak of Playing It Safe

Posted On: 07.14.16

playing it safe

Have you ever read a book at the exact right moment in your life? This just happened to me.

The book: Playing Big: Practical Wisdom for Women Who Want to Speak Up, Create, and Lead by Tara Mohr. Full disclosure: I went to college with Tara. I didn’t know her during my undergraduate years, but we have connected since and I’m grateful we have. A couple months ago, we met for lunch downtown. We talked and talked and ate yummy food and exchanged books; I gave her a copy of my recently-published novel The Ramblers and she gave me a copy of her Playing Big. On the way back uptown, I began to read it and was immediately hooked, but life is life and for some reason the book got sucked into the ever-mounting bedside stack and I didn’t pick it up until this week. I finished it this morning and now I am sitting at a brand new Starbucks near my daughter’s musical theater camp and I have so much to say. I’m revved.

The book is about many things, but ultimately centers around the powerful thesis that many modern women, many brilliant modern women, are playing small in their personal and professional lives. The book is both a theoretical exploration of why and a practical guide to how we can stop doing this. Tara writes from a place of wisdom and wonder, compassion and firmness, from a vantage of personal experience and professional expertise. If you are a woman and are curious about how to overcome and work with fear, how to transcend deeply entrenched good-girl and good-student habits and mores, and how to move toward a life that is more fulfilling and better integrated with your personal goals and desires, I simply cannot recommend this book highly enough. Buy it. Read it. You will be so grateful you did.

Okay, enough of the sell. What I am startled by is how this book affected me, how it woke me up to some vital truths. One of those truths:

I have been playing it safe.

I have withheld my opinions on, and questions about, certain things, important things, out of fear that I will offend others, embarrass myself, or become less likable.

I have been writing recently for praise and approval instead of for self-expression and service. (This: soul-sucking.)

I have been hiding out in various ways – behind sweet, filtered, glorious Instagram pictures of my family and city and vocation and home, in tiny or tall glasses of wine that bring a twisting shame, by writing fiction when I’m beginning to realize that my heart yearns to write the truth.

I have been sad and exhausted and resentful at times because I’ve spent months simultaneously promoting a novel and accompanying my mom to chemo treatments. (Mom is thankfully now in remission, which is amazing news, but it has been a hard time.)

I have been feeling guilty and quiet because I am the poster-child of white privilege. The events in the world have rattled me and I feel angry and despondent and want to do something and say something, but I don’t know how or even if I’m allowed to. I would like to figure this out. One thing I did that felt right: I talked to my nine-year-old about the police shootings and the massacre in Dallas. I answered her questions as best I could. I saw curiosity and emotion and flickers of understanding and outrage in her eyes. This was something. A step.

I have been confused about what I want to write next. I have so many ideas, have written so many pages even, but something isn’t clicking and I’m realizing that this itself is meaningful. After reading Tara’s book, I’m curious about my own wheel-spinning and resistance and whiteboarding (a fascinating idea she explores). I’m beginning to think that part of it is that I’ve been playing it safe instead of doing what I most want to do.

What do I want to do?

I want to tell the truth. I want to connect with others by telling the truth. I want to help other people see the truth and tell it in their own lives. Truth about what?

Loss. The loss of Dad eight years ago shredded me, but it also made me who I am today. I can only see this now, with the benefit of time and distance. Before Dad got sick, I was one person and after, another. Before: I was a bit full of myself, insecure, well-meaning and kind, but also quite aimless, blind to my privilege, out of touch. Not a bad person, no, but I hadn’t been shaken up by life yet; I took a lot for granted, too much maybe. After: Scared shitless, aware of my own mortality and the beauty of the turning world, full of fiery ambition to become a good writer, a good mother, wife, sister, daughter, to live fully and well, to see and savor my moments. Only when Dad got sick did I pull my manuscript of my first novel out and go to work polishing it. I wrote query letters to agents from the linoleum floor of his hospital room. Dad finished reading my manuscript a few weeks before he died and I’m still not sure what he thought of it, but I don’t think he loved it (Spinoza and Kant were more his jam). The first thing I ever published: his death announcement in the New York Times. Two weeks after he was gone, I signed with my first literary agent. A couple months later: My first book deal. I can say without equivocation that losing my father made me a writer. This is a complicated truth for me, something I am still processing. What if the most terrible thing that has happened to you is also, viewed from a different angle, the best? Loss is part of who I am, how I view the world. I’m a different species of mother (and I would argue a better one) because I’m aware (too aware?) of the fragility of life. I need to talk about this, write about it.

Alcohol. This continues to be a thing for me. Probably because I have overthought it and made it one. The truth is that I have had periods of terribly unhealthy drinking in my past. College. Law school. Early motherhood. Times of wild, worrisome excess, even blackouts, self-loathing and shame. Simply: I was on a bad path. And then I got off it. I took a year off from drinking. I saw the world through a new window. I felt peace and learned tons about myself. I wrote about it. And then I went back to drinking. I have been back and forth – as those of you who read my stuff know – but never have I returned to that awful spot I was in. Not even remotely close. And what I am seeing now? This is something! I caught myself. I must be careful, yes, and quite (I believe we all must be with alcohol as it is an addictive substance) and this is what I am doing, being careful, in my own intriguing and sometimes utterly maddening way, but I must figure this out for myself. I must banish perfectionism and realize that this does not need to be about black and white, all or nothing. Maybe, for me, for many of us, it must be about self-awareness and presence and making my life one that I do not want to numb out and escape. What I want: to bring this conversation to the center. There are SO MANY of us who fall in the precarious middle of the spectrum, who are not addicted to alcohol but who do fear its effects and worry sometimes, people who are not unable to give up drinking, but who are maybe (for complicated and compelling reasons) unwilling to. I am more curious than ever about this topic, about why so few people are exploring the vast middle ground, about why it figures and features so prominently in my own existential narrative. Drinking has been part of my identity and my family’s; my grandfather drank moonshine with Hemingway. This is interesting and worth exploring and I want to talk about it. What I don’t want: to be a role model. I do not profess to have this – or any one thing – figured out. I want to feel my way through this, to learn – and perhaps write about feeling my way through it, my lessons – in a way that is open-minded, personal to me, but never do I want to come across as giving advice.

Privilege: Ugh. I don’t know what to say about this one but around this topic, I feel the need to be most careful, to play it safest. Why? I don’t know. It scares me, but that also leads me to believe that there is interesting ground here. I will be the first to admit that I have had incredible opportunities, educational and otherwise, in my life so far. I have had the freedom to pursue my passion for writing without worrying about repaying law school loans. We are living in Manhattan and sending our three daughters to the wonderful private school I attended as a kid. All of this is true and I’m grateful beyond measure and I wonder sometimes what effect any of this has on how I see the world and how I’m seen. Some of my most biting reviews of The Ramblers hinge on the fact that there is so much privilege at the center of the narrative. These reviews hurt me and I now see why; there is truth there. My characters, though they have heartache and are truly struggling in their lives, are ultimately deeply privileged people. I’m not sure I saw this so clearly when I began writing the book and bringing these characters to life. Maybe I was too sequestered in my Ivory Tower, 1% world to appreciate that their struggles and pain, while legitimate and defining and real, were also rooted in privilege (complicated, but undeniable) that not many know or enjoy. And yet. I love my characters. I love the book. I’m so proud of it and I believe, more than ever, in its message: We must allow ourselves to ramble in life, to stumble and swerve our way toward happiness and meaning. I realize that this is exactly what I’m doing – with these fast-flying words, with the books I’m writing and dreaming of writing, with the questions I’m asking and even avoiding – I’m finding my way. I also realize that all of this talk – about happiness, about purpose, about hiding and seeking, playing it safe and speaking up – is itself privileged talk. If we are worried about survival, we are not talking about this stuff.

Perfectionism: At some point along the way, I became a raging perfectionist. I’m not sure when it happened. I have distinct memories of struggling in school, of being in the “low” reading and math groups, but I also remember being untroubled by these things. And then something clicked for me and I took off academically and maybe this is when I became addicted to praise and approval? Oh did I love getting A’s and scoring that winning goal in the homecoming soccer game. Achievement. Applause. Accolades. Yes, please. But adulthood is a different kind of space, isn’t it? There are no gold stars. Things are murkier. There is no room for perfection. We cannot parent perfectly. We cannot be perfect partners and friends and children and writers and citizens of the world. There are no ready rules or roadmaps; no one kind-faced teacher at the front of the classroom to smile and say Good job or You are on the right track! For me, and I suspect many of us, perfectionism continues to be a real problem, a robust road block. If we are continually striving for some illusory perfect self and perfect life, we will be miserable. (Again, perfectionism is itself a badge of privilege. I see this.)

Anna Quindlen said, “The thing that is really hard, and really amazing, is giving up on being perfect and beginning the work of becoming yourself.” Sitting here, at Starbucks, in a sea of New York City strangers, I read her words again and again and I smile into my screen. Beginning the work of becoming yourself. This is what I’m doing. This is what these words today are. They are a big old fuck you to the fear that’s been holding me back (which includes the fear of using profanity), to the good-girl, heartbreaking act of playing it safe. These words are a messy ode to telling the truth. Telling the truth in a way that is not reckless, but thoughtful. I believe this is possible.

These words? They are the beginning of something for me. The seeds. I don’t know yet what that something is, but that’s okay.

I’m excited.


Have you been playing it safe in your own life? Are there things you would like to talk about or write about or do, but are too afraid? 

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36 Comments for: "The Slow and Certain Heartbreak of Playing It Safe"
  1. Cristina Scudder

    YES. MORE OF THIS. BEST POST YOU HAVE EVER POSTED. Love from a fellow yalie.

    • Aidan Donnelley Rowley

      Thank you, Cristina. So much. (And always happy to cross paths real and virtual with other Yalies!)

  2. I think it’s possible that this post of yours has come around at exactly the right moment of my life. Playing it safe. Yes. I have spent a lot of time lately feeling unsatisfied and a little lost in the shuffle of my life. I suspect that a lot of these feelings come from the march of early parenthood – my baby just turned one. I have spent a lot of time making excuses for not doing the things that I really want to do, namely writing the book that I know is somewhere inside me and becoming again the long distance runner I once was. I suspect that part of the reason for this is that it’s unpopular as a parent to say that being a parent isn’t enough. So I have been safe – morning routine, working, coming home to the hurricane of dinner/bath/bed, and the collapsing on the couch in a heap of exhaustion. But reading your words makes me not so afraid to admit that I both want and need more than this, and to start to figure out how to have it.

    • Aidan Donnelley Rowley

      Thank you, Sam. This is all so important and interesting… I do think so many of us fall into patterns of playing it safe, of doing what we think is expected of us, of avoiding the very things that might make us feel most fulfilled and happy. And parenthood. It complicated all of this, too, because we are examples and time is swift and we want to absorb moments with our littles, and enjoy them and yet we do not want to lose ourselves in the shuffle, which I think is in some sense inevitable. Or maybe more accurately: We become different selves once we become parents.

      Thanks so much for this thoughtful comment. xx

  3. Denise

    Yes. Yes. Yes. Profound. True. Real. I am on a similar journey and am so very grateful you wrote these words.xo

    • Aidan Donnelley Rowley

      Thank you, Denise. I suspect many of us are on similar journeys… there is something universal about some of this stuff. Grateful to have your eyes and words. xx

  4. Laura

    Thanks for writing this, Aidan. So much of it resonates with me. I saw your Instagram post about Tara Mohr’s book & immediately ordered it (it fittingly just arrived today), because I’ve been playing it safe & for quite some time now, I’ve been wanting to (& I’ve been trying to figure out how to) reach for more.
    There’s so much in this post to respond to, but I just want to say one thing: so many of my favorite posts of yours seem to tell the truth in a thoughtful, but not reckless way. The world needs more of that, and you’ve already started doing it!

    • Aidan Donnelley Rowley

      Oh, thank you, Laura and I cannot wait to hear what you think of the book as it spoke so powerfully to me. All of this stuff is so tricky and so important and I’m happy that I’ve allowed myself to start talking about it. Now to sustain the courage… I’m grateful for your comment and encouragement.

  5. Cannot share this fast or far enough.

    “I’m not sure I am even allowed to.” That statement holds so many people back. You have done a great thing. I hope you keep going.

  6. What Amanda said. Whose approval are we waiting for? I am too, whoever it is. Tara’s book moved me as well. I’m so grateful you wrote this. Keep going. xox

    • Aidan Donnelley Rowley

      Whose approval are we waiting for?

      I have no idea. Not a clue. But we will never get it. We need to just go for it, whatever that means. So so much easier said than done, I know. As always, so honored to have you along for this ride. xx

  7. I read THIS at exactly the right time. I am working on my own very difficult book of truths and it is scary and uncertain and I feel like I don’t have the right to write it at times. I can relate to the loss of a parent making you a writer and I am so deeply sorry to hear that your mother is going through chemo. I have been there. Thank you for this honest post.

    • Aidan Donnelley Rowley

      Anne, it is so tough and scary to write the difficult stuff, but I so believe that it is worth it in the end (if we can do it thoughtfully, with care and compassion. I do not believe in truth at all costs, in knowingly hurting people). My mom is actually in remission now, which is amazing news and we are all over the moon, but it was a wrenching few months. (I’ve edited the post now to clarify this!)

      Thank you.

  8. So much honesty and truth in this post.

    I like many have been struggling with my own demons lately – demons about failure and not being good enough and disappointment (for myself and others?). It has been a crazy time for me.

    And the worst part about it is: I sometimes think to myself that I have no right to feel this way. Because in a world where really terrible things are happening (mass shootings and war and such), my life is not that bad. I have friends and family enough that love me that will help pull me through. And for that, I am incredibly grateful.

    But I also still have twinges of intense fear. And the past few weeks have led to almost crippling anxiety about my life. Because I know that I can do more and be more than I am right now. And I know that I just need to work harder (another first world problem probably).

    Anyways, thank you for your wonderful words. I will have to put Tara’s book on my TBR list.


  9. Lara

    Thank you for writing this. So much of it resonated with me. I too have been holding back and playing safe – a lot, actually. So much so that I’ve felt paralyzed creatively, personally, professionally for some time now. You’ve inspired me to seek and speak and write the truth (my truth, anyway). Off to order Tara Mohr’s book…

  10. AG

    You are you and this blog is you and that has what has continuously kept me coming back to it for many many years. Yours still ranks as my favorite blog of the many I read. I never feel bad about my own life or like I am not enough after reading your posts….instead I am fueled with thoughts and passion to let my mind wander. Your writing and honesty is a gift to all of us. Also I just ordered the book and am so excited to dive into it….

  11. Hope

    Great post, ordered the book just now. It really struck a cord with me. I have been one to play it safe. Always a people pleaser of sorts. It struck me how you talked about as an adult there is no perfect or right way to do all of this. As a kid that is all we get feedback for the grades, sports accomplishments and it does not translate to adult life very well. I have seen the perfedtionism in one of my daughters especially and we have been focusing on process vs outcome goals. It has helped her zero in on the prices and look at things in a new way, less of a zero sum game if you are not perfect.

    For me as an adult the hardest thing I have been coming to grips with is no matter how perfect I live my life and make my decisions I cannot control others in my life. I always knew this but it is another thing when a person who is the closest to you shatters your world. It has really been a process for me. In a way I have become more guarded and removed. It feels safer to isolate and protect yourself but that is not living.

    I look forward to reading the book be also more from you in the future. Thank you!

  12. Bumby

    Nicely Done!

  13. Amy

    I’ve missed your words and I needed these. Just turned 40 and am struggling with letting go of approval and pleasing others. Thank you for opening up. I ordered the book as I’m sure I can learn from it.

  14. Amy

    Do you listen to on being? I’ve flagged this page for future conversation with my young kids. Thought you would appreciate.

  15. Rachel

    Seeking the approval and pleasing others will eventually eat one alive,if not make one sick. They will not thank one, and even if they do, does one need other’s approval to make oneself happy? Not really. If you don’t self actualize your truths, your honesty, then you’ll end up feeling shame, guilt, sadness. It will just make you sick, physically, mentally, emotionally.
    I love reading the article, because it brings so much to home, the way I’ve been living, leading my life. We are not perfect, none of us. I’m trying to be compassionate to myself, my mistakes, my attachment to the ‘creature comforts’ which haven’t made me happy. I forfeit my happiness to please my dad; my husband, my ex-boss, my siblings, my best friend, etc. At the end of the day, I didn’t make myself happy. Sigh. I hope to turn things around. I have to be a living example to my 1 child. I want passion in my life. Passion for others, hobbies, helping others.
    thanks for your good work!

  16. Kendra

    I agree with the first commenter – this is a great post. I felt excited reading it. I think you hit on something so essential to dealing with the issues you discuss: owning them and your own thoughts about them, regardless of what other people think.

    I wanted to comment on alcohol. I originally found your blog because of your year without wine (I’ve commented several times over the years). It was an added bonus that you are a writer, as am I. For many years I self-medicated with wine (to deal with depression/anxiety issues and because I plain old like to drink). I have worked hard to get to a better place circumstantially in my life, and recently stopped self-medicating (or to put it in terms that sound more honest, I stopped abusing alcohol). Like you, I am in that middle ground. I love drinking, and am prone to overindulging when I do drink, but am not an addict or alcoholic (of course many people who see drinking too much at any time as a sign of alcoholism would disagree outright with that statement, but I stand by my self-assessment and I trust my judgment of myself). Like you, “quitting” does not necessarily indicate not drinking ever (although this remains a possibility I consider). It means stopping my regular dependence on wine, and creating a life I want to be present in. Like you, there is always a feeling of process and experimentation in terms of when and how much I feel comfortable drinking. I accept that I will always love to drink and I will always tend toward overindulging. Those are the parameters that I am working with and they will never change. Finding my own path within them, whatever it is, is my own business, though I am happy to share my experiences. But I accept no judgment from anyone other than myself. I (try to) feel no shame about this aspect of my life. It is who I am, it is one of my struggles. I deal with it, just as I do my depression. I allow myself to change my mind and develop different perspectives of my struggles, and pick the one that feels right to me at the time. Another way of describing this seemingly dangerously subjective process is – personal growth!

    I would be interested in joining the conversation on the middle ground, if it’s one you want to develop.

    • Jenny

      Love this comment! I have been obsessing about my drinking for several years and it is nice to know there are others out there in the same boat of trying to find a middle ground that isn’t all or nothing.

      • Kendra

        Thanks, Jenny! I appreciate your reply. There are plenty of us out there, having our successes and our failures, learning and living!

  17. I have spent my whole life being afraid and seeking approval. Again, approval from who? It continues to be the biggest road block in my writing. Thank-you for the post and the book recomendation. Can’t wait to read what you write next!

  18. I read this and felt, whoosh, a feeling of relief. I felt my shoulders relax and the tension leave my body. It is a relief to read about others dealing with their privilege, wanting to speak up but not being sure how to, and also about wanting to write more but being scared to. I, like, your daughter, feel outrage too, some of it aimed at myself for not having opened my eyes for so long. But I like to believe that we are able to change and grow, and now that we can’t turn away, we won’t.

  19. Lynn

    Ahh yes I am also a fellow Yalie and this is exactly what I needed at this exact right moment. A few weeks ago I threw out nearly everything I owned, gave up my Manhattan apartment and moved back to my childhood home on LI – luckily my job is allowing me to work remotely for the summer. Where to next? I have no idea! But my mother died just about a year ago and this is the first step for me in trying to sort it out. Trying to put aside the fear and need for approval but I have no idea what I want or even what I think about some topics as it’s so deeply entrenched. Thank you for your words and candor. Looking forward to continuing to follow you!

  20. Relate very much, especially to playing it safe. Ordering the book!

  21. It’s sad that so many of us relate to how you feel about playing small, perfectionism, our skewed vision of the world, etc. But I love that this is becoming a conversation among us because often we feel so alone in our feelings.

    Whatever world we live in, I think deep down we all seek purpose and to live a life is meaningful. . So many of us play small because we think “Who am I to do this?” “Who do I think I am?”

    We tell our children all the time to “You can do and be anything!”,”Follow your dreams”,”The sky is the limit!” but all of that goes in one ear and out the other just like “Make your bed” “Brush your teeth” “Don’t fight with your brother.”

    One of the hardest lessons I’ve had to learn (still learning) is to live the life I want my kids to live. That means I must SHOW them what a well-lived life looks like. I have to play big in order for them to learn to do the same. Kids watch what we do and they will eventually do the same. This mentality has been forcing me to look at how I spend my days. Am I pursuing my own dreams? Am I “going for it” in my writing, coaching, etc.?

    My kids are my motivation to play big because I want so much more for them than I gave myself for the first half of my life.I didn’t have the role models I needed to show me what a well-lived life looked like. We’ve already broken so many unhealthy cycles but we have a long way to go.

    Thank you so much for sharing Tara’s book and for expressing your vulnerabilities. Clearly, we are all right there with you!

  22. Pamela

    This is beautiful Aidan. Thank you for acknowledging the murky things. I too play it safe and small and lately it’s been causing me some sleepless nights. Mostly because when my husband was deployed for a year I didn’t play it safe or small because I couldn’t. I was forced to show up and it was really fucking hard but also kind of great and I’m trying to get my courage up to get back there again.

    And of course I hear you about wine – I love it too much and have to be vigilant. I so appreciate the middle conversation:)

    In terms of privilege, you were born lucky, but there is no need to be ashamed of that. I grew up and still am middle class and I DO have to scrimp and pinch at times, but I am still privileged. I have enough food and a car and my kids go to a great charter school and I have enough. There is no point in qualifying our privilege just as there is no point in qualifying and comparing our pain.

    Much love to you as you begin the big work of unraveling.

  23. Yes to so much of this, Aidan. Thanks for your vulnerability. Ordering the book. xo

  24. Aidan This piece resonates deeply with me for many reasons. (Changed forever by loss — oh yes.). But rather than go there I just want to say how heartened I am to realize I’m not the only one who’s been struggling with the risk of writing my own truth. What I learned this week is that the risk is real. People will lash out, they will unsubscribe, they will say (as several have to me) “Keep your opinions to yourself.” They will be angry that your views don’t match theirs. I’m a bit bruised by all of that. But I still say “Go for it.” We need more truth and we can survive with less approval. So glad Lindsey Mead pointed me in this direction this morning.

  25. Leigh


    Love this so much! Thank you. I’m in the process of trying to assert myself and not be such a “yes man” (or woman ) and I am definitely going to check out Tara’s book.

    I love what you said about alcohol and perfectionism. So true. I have had a complicated (to say the least) relationship with booze for most of my life and after nearly a year and a half of working to quit drinking, I’ve been sober for a little over 2 months. I too am deeply working on becoming my true self and in the process have made it my lifelong goal to abolish perfectionism. I love what you said, “There is no room for perfection.”

    Just wanted to say thank you for sharing your truth. Keep it up ❤️


  26. Michelle

    Aidan — Great post; I can’t wait to read the book you mentioned.

    I don’t have much to add beyond what the other commenters have already said, but as a longtime reader of your blog (and, now, both of your novels), I am very glad that you addressed the concept of privilege in this post. It is something that you’ve hinted at here and there on the blog, and as you note it’s something that’s woven into “The Ramblers,” but it has always irked me a bit that–to my knowledge, but I could absolutely be incorrect–you’ve never really addressed it head-on in a blog post. Of course, you shouldn’t be ashamed of your past and present privilege, but it is important to acknowledge. It might be weird or awkward to talk about, but I think that especially for those of us who haven’t always lived a lifestyle as you do, it becomes an absolutely glaring omission when you ignore it because it’s a difficult topic for you. (To be entirely frank: I’ve been tempted to stop reading your blog on occasion because it seemed to me that you were sometimes oblivious.) Thanks for opening the curtain, even just a little bit.

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