Books That Make You Feel Okay When Struggling

  • Post last modified:September 18, 2021

The books You’ll Grow Out of It by Jessi Klein and I Might Regret This by Abbi Jacobson are stacked on a wooden floor next to some other books. A strand of warm twinkly lights lies across them, and there is a potted plant in the background.

“As a wolf, I’m a diamond in the rough. I crack jokes. My whole life is about trying, about speaking up in order to be seen, about howling with laughter or howling out how I see the world.”

– Dolly Alderton

It’s rare that I come across those kinds of books that just make you feel better somehow, but when I do, it’s hard to shake them from my mind. I’ve been thinking about the shift I’ve experienced recently with the type of books I like to read, and am trying to be more attentive to what I’m drawn to and why — I suppose it’s like intuitive reading? I think that what you want to read can reflect your mindset at that moment, especially if you are one who turns to words for comfort. For example, my own uncertainty about life right now is probably why I’ve been falling in love with so many memoirs lately. Because they are real and consist of concrete stories. To see someone endure the same struggles and make the same mistakes as you is incredibly reassuring, but I suppose that’s no secret. But pair those experiences and wisdom with gorgeous writing and you have a book that you’ll be coming back to for years. The three books chosen below were result of me looking at my bookshelf and drawing out those that have given me something valuable in uncertain times. Coincidentally, they are all essays/memoirs written by successful women I admire greatly. This is one of those posts you write knowing that you are leaving some stuff out, but I know I won’t remember the other books that belong here until after I hit “publish”. If I find any others, I’ll mention them over on Instagram.

The book I Might Regret This by Abbi Jacobson is against a light wooden background with a strand of warm twinkly beside it.

I Might Regret This by Abbi Jacobson

Out of those on this list, I think you’re most likely to know Abbi Jacobson, co-creator and actress on the comedy Broad City. I Might Regret This is pitched as a memoir written over the course of a solo roadtrip across the country, and it is — but there is a lot more to it than that. The criticism I hear most often about this one is that it tends to be a bit disjointed (which is strange considering the premise seems pretty linear), but they aren’t wrong. I personally am one for a bit of strategic mismatching, and I think Abbi did a wonderful job of expressing the chaotic nature of life. After all, she is going on a roadtrip to sort some things out, and she makes the reader feel as if they are right there with her. Abbi keeps her sense of humor in this book, and reminds me a bit of my own journaling with her mix of words and drawings.


This picture is a simple black handlettered quote from Dolly Alderton’s book, Everything I Know About Love. It reads “To choose to love is to take a risk.”Everything I Know About Love by Dolly Alderton

This book makes my favorites list pretty often, so you might have seen me chatting about this one before. If not, it’s probably because I listened to it on audio and don’t have a physical copy (huge bummer because I could annotate this baby to death), and therefore can’t take any photos of it outside of bookstores. So, I’ve tried to make up for it with a handwritten quote I like. This book is full of quotes I like, and considering most of them constitute passages, it came down the length here. Everything I Know About Love resonated the most with me out of the three here, and in my opinion, was gorgeously written. Highly, highly recommend. If you want more Dolly wisdom, listen to The High Low podcast where she co-hosts.



You’ll Grow Out of It by Jessi Klein

You’ll Grow Out of It is the one out of the three here that surprised me the most. Jessi Klein is most recently known for voicing Jessi on Big Mouth (if you haven’t seen it and can handle a horrible amount of relatable cringing, go watch), and I didn’t really know much else about her when I picked up her book. I’ll let June-of-2018-Grace tell you what she thought in a post from way back then, when I first read it: ‘Her talents clearly go beyond voice acting and screenwriting, because this was a great memoir, relatable especially if you are chasing a creative career.  Klein addresses everything from her youthful insecurities to her present-day struggles, exploring success and what it means to “make it.”‘ Over two years later, this one is still memorable for me, and might deserve a re-read.

The book You’ll Grow Out of It by Jessi Klein is held up against a light wooden background with a strand of warm twinkly lights in the background it.

Well, that’s it for now! If you have any recommendations for me, please let me know! I hope you are feeling steady right now.

Much love,



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  1. Kate

    Great post! All of these are on my tbr pile I must get to them asap! ♡

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