Top 8 Books to Get You Through Every Milestone of Your Twenties

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Spoiler Alert: No one told me life was going to be this way!

Growing up I only dreamed of the days when I would finally move out from my parent’s house and start a life of my own. As a woman both ambitious and driven, I envisioned a lifestyle rich with that Sex and the City -esque type vibe.

I saw quaint apartments and cozy coffee shop dates in my future. I believed in the luck of finding Mr. Right amid 20,000 or more strangers whom would also find home in whichever city I happened to settle down in post-graduation. Heck, I figured life would somehow magically fall into place if I just stuck to my plan- college, internship, career, marriage, babies…

Sure, there’d be midterms to cram for, an insane number of lectures to attend, and a ridiculous amount of paperwork to fill out regardless of what path in life I chose, but there would also be exhilarating & stress-free vacations and drunken nights spent with some unforgettable friends.

And it would be inevitable that during the entire process I’d be broke as broke could be. But it would be the kind of “poor” that you laugh and reminisce about later in life, after you’ve made it big.

You know, the kind where you ask yourself did you really steal coffee creamer out of the cafeteria to save the $3 it would cost for a new bottle at Walmart or what were you thinking riding your bike to campus in the dead of winter to avoid buying a parking pass?

The days of eating ramen noodles for breakfast, lunch and dinner or couch-surfing between friends’ homes were not to be feared. No, they were most certainly a rite of passage. Something that everyone must experience at one time or another.

And perhaps because I knew about that rite of passage, I was alright with it when it happened to me. I expected it, I had time to mentally prepare for it, it was a necessary stepping stone to reaching a bigger milestone. But I swear, no one ever told me of what else to expect in my twenties.

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Of course, you hear about such things as heartbreak and failure; defeat, rejection, debt, and a myriad of other “adulting” problems but you half expect that they won’t happen to you (or if they do, you pray and hope that they will resolve themselves).

You start to think that maybe you’ll be one of the lucky few; you’ll make it into your thirties practically unscathed and with positive energy still flowing straight out of you as if that’s where it always belonged.

But then reality will hit and you’ll suddenly realize you’re not as invincible as you claim to be. And when it does, know that you are not alone.

8 Must-Read Books for Women

There’s plenty of people that talk about these life displeasures, but truth be told, it’s such conversations that often fall on deaf hears. Seriously who wants to be reminded of all that could go wrong when it’s so much more pleasant to think of all that could go right?!

As an almost thirty-something I write this blog post not to dim the opportunistic thinking of those just entering their twenty-something years, but to guide those dreamers and goal-seekers to the resources that will get them through those expected (and not so expected) milestones that hit every person in their twenties; A sort of what I wish I had known sooner type guide to living your best life imagined.

So here you have it: the Top 8 Books Every Independent and Motivated Woman Needs to get through the Milestones of Her Twenty-something Years.

8 Books Every Twenty-Something Woman Should Read

This post may contain affiliate links, for more information, see my disclosures here.

1). You are a Badass: How to Stop Doubting your Greatness and Start Living an Awesome Life by Jen Sincero

I’ll be the first to admit, I often avoid the self-help section of any book store, for I fear that the promises these authors make are all a bit too good to be true type deals. However, I can say with certainty that Jen Sincero delivers. And she does so with an unparalleled bit of sass that kicks the entertainment factor of this book up ten notches.

Reader beware, this book is not for the faint of heart and if you squirm at the sight of curse words then you might as well just run in the opposite direction. But if you can relate to her unconventional sense of humor you may just find yourself changing the self-sabotaging beliefs that keep you from getting what you want in life. Sincero helps her readers create a life for themselves that they can totally fall in love with, and more importantly she helps them create it NOW!

As the book jacket detail, By the end of YOU ARE A BADASS, you’ll understand why you are how you are, how to love what you can’t change, how to change what you don’t love, and how to use The Force to kick some serious ass… (Click for More Info)

2). The Rhythm of Life by Matthew Kelly

This book is along the same lines as the above book by Jen Sincero; however, it is written with less of an edge, and in a more politically correct tone.

Kelly breaks down his six-part process of living each and every day with passion and purpose. He talks about creating the best-version of ourselves and why that matters infinitely more than what we choose to do or what we have in our lives. I especially love the personal anecdotes he adds to each chapter; it’s a personal touch that really brings the material to life.

Perhaps the greatest message I took away from this book was the reminder that Everything is a choice. This is life’s greatest truth and its hardest lesson. Not power over others, but the often untapped power to be ourselves and to live the life we have imagined… (Click for More Info).

3). 20 Something, 20 Everything by Christine Hassler

I first opened this book and was stunned by how easily I could relate to the author and her experiences. To keep from being too over-dramatic, all I will say is that from the first chapter I got the eerie sense that I was, in actuality, reading my own autobiography.

Just take the opening chapter for instance. Hassler writes, At the age of twenty-eight, let me begin by saying that my twenty-something years definitely have been my twenty-everything years. They simply have not been the type of “everything” that I thought they would be. I know that many other twenty-something women can relate to this feeling. After all, we are young women in a society where an unbelievable amount of attention is focused on doing and having it all- it’s only a matter of time before Prozac becomes an impulse buy at Starbucks…

I personally feel as though this is a must-read for every twentysomething whether you are going through a quarter-life crisis or not!(Click for More Info)

4). Conscious Uncoupling by Katherine Woodward Thomas

I never had a high school sweetheart, and even in college I wasn’t a serial dater. I had plenty of guys who were friends but none whom I was eager to let cross the line into the world of “boyfriend”.

Let’s face it, my mother may have been right- I’m as independent and stubborn as they come. So, heartbreak wasn’t something that was exactly on my radar; however, when it did finally peak its ugly head into my life it did so with such a vengeance that I didn’t feel like myself for months.

In this book, Katherine Thomas does a wonderful job of breaking down the process of healing post-breakup into 5 relatively simple steps. Though Katherine isn’t an official twenty-something she details her experience with a divorce that ended her own ten-year marriage with such eloquence and beauty that I find myself once again believing in happily-ever-after’s.

Whether you’ve just recently ended a fling, been dating for years, or trying to love again after a divorce, you’ll take comfort in realizing love doesn’t always have to hurt. (Click for More Info)

5). Wild by Cheryl Strayed

I must admit I watched the movie-version of this real-life tale long before I ever cracked open the book.

Though in all honesty, I felt more in-tune with the author’s thinking and as though I gained a more in-depth and personal accord of her 1000-mile trek along the Pacific Crest Trail only after reading the book.

For me, this book was about healing and evidence that our lives can turn around even after an endless amount of hardship.

This story is powerful and is truly a source of inspiration to find one’s self. (Click for more info)

6). #AskGaryVee by Gary Vaynerchuk

He was an entrepreneur before it was cool. An original.

I can’t help but love the advice given in this book in regards to making things happen in a big sort of way.

He is straightforward in how he talks and gives no-bullshit answers to the questions that plague many young business-minded individuals today.

I especially love how his focus goes beyond the traditional methods and he shares how-to truly harness the power of social media platforms such as Twitter, Facebook, and Twitter in order to build a following that will help entrepreneurs alike reach whatever goals they happen to set.

Gary Vaynerchuck is brutally-honest, upfront and a living example of what it truly means to hustle in this ever-changing world. (Click for More Info)

7). Broke Millennial by Erin Lowry

Because what twenty-something isn’t freaked out by finances?

With so many life-altering purchases on the horizon (tuition, apartment rent/mortgage, car payments, credit card debt), it is so easy to get overwhelmed. And it’s even easy to get lost in the never-ending stack of bills that seem to pile in your mailbox, but Broke Millennial shows step-by-step how to go from flat-broke to financial bad-ass.

Erin Lowry is a financial expert that presents this age-old topic in new light (and with a bit of humor). Here’s just some of what you can expect:

  • Understanding your relationship with moolah: do you treat it like a Tinder date or marriage material?
  • Managing student loans without having a full-on panic attack
  • What to do when you’re out with your crew and can’t afford to split the bill evenly
  • How to get “financially naked” with your partner and find out his or her “number” (debt number, of course)  . . . and much more. (Click for More Info)

8). I’m Happy for You (Sort of…Not really) by Kay Wills Wyma

Last but not least, with a list full of guides on how-to create the best-you possible, it wouldn’t be right to not include a manual on overcoming comparison.

Let’s face it, we all do it! We think our lives are going great and then we hop on to Instagram or Facebook only to be reminded of everything that we have not yet accomplished. Talk about defeating!

In a world that so eagerly advertises the good that goes on in our personal lives, it’s important to understand that we are all capable of finding the same quality of happiness. This book is all about taking back the joy that excessive comparison often robs us of! (Click for more info)


There’s no instruction manual for life- but it’s my hope, friend that this list of books may help you navigate your years a little more easily!

Now it’s your turn! Add your own suggestions in the comments below on what resources most helped you in your quest to achieving success during your twenty-something years!

Here to Support YOU! XO- Britney (

Browse more: Personal Growth Happy Goal Setting

Top 8 Books to Get You Through Every Milestone of Your Twenties
Britney Zondlak

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I'm Britney,

Just a small-town gal with a passion for fitness + health- Using my little corner of the Internet to spread light and positive vibes. It is my mission to encourage all women to step into the best-version of themselves possible. After all- you deserve it, girl!

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