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The 7 Best Books to inspire Tired Solo Entrepreneurs

This list is for anyone who’s tired of seeing lists of “Bill Gates’ favorite books” and it’s just a bunch of old white guy authors. You don’t have to identify any particular way to connect with the books on this list, but they are definitely books that have spoken to the challenges I’ve faced in the working world as a woman. Which is to say, I found these books in the middle of despair, blind rage, exhaustion, overwhelm, or some unholy combination of all the above. 

A brown woman with glasses reading a book

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I have a confession. I struggle with self-care. No, not the “self-care” of social media, which consists of buying a new moisturizer, scheduling a massage and telling my haters to get bent. I struggle with the self-care of being a human in this world – things like setting reasonable expectations for my productivity, honoring rest when my body feels terrible, avoiding foods that trigger my migraines (I’m getting better at this last one, thirty-eight years later). 

Compared to how toxic the advertising industry can be, building a solo business empire should be a walk in the park, right? There I go, should-ing all over myself again. Don’t get me wrong, working on building my business brings me a lot of peace and a decent amount of satisfaction. It’s just that when it also brings me anxiety, doubt, fear, overwhelm, exhaustion, dissatisfaction or frustration, the call is coming from inside the house. There’s no one else to blame when your biggest enemy lives inside your own head.

Did you know that when people get scurvy, a severe vitamin C deficiency, all their previous wounds can re-open and previously broken bones can unmend? Without vitamin C, your body can’t make collagen–the material that holds scar tissue together. (If you also have a dark and twisted sense of wonder, read more about scurvy here. Content warning: gross.)

Following your dream to launch your own business can feel a lot like that. 

On good days, you’re hopeful, optimistic, confident. On bad days, you’re jiggling your leg, thinking of every unkind word a teacher or a peer or a boss ever said to you, listening to the demon on your shoulder who says you should just give up and stop expecting so much. Just take another crappy job. You’ve survived it in the past. Maybe you just need to toughen up, buttercup. All those old injuries you thought had scarred over just split open, unleashing a Pandora’s box of crappy self-talk.  Back up, scurvy beast. 

If starting your own business, working for yourself, and building a legacy have the power to open old emotional wounds, then you know what else is true? 

They have the power to heal. 

Every time you say something rude to yourself or feel undue anxiety or start spiraling into a pit of doubt, you’re getting the opportunity to heal those things by correcting your self-talk, calming yourself down and building a rope ladder out of your doubt-pit. If you don’t, eventually you’ll just give up. Which means if you’re committed to building your business, you’re also committing to moving past these old blockages. So today, I’m going to share seven books I’ve read that have given me some important pieces of the puzzle. Wisdom, or compassion for myself, or a deeper understanding of how to navigate the maze of emotions that were formed when I was in a much worse place and no longer have a use for. And I’ll tell you why I liked the book, so you can judge for yourself if it’s something you might find useful, too. 

A Word About Libraries vs. Buying Books

I’ll link to everything to make it easy to buy them – but I’m also a huge advocate of local libraries, one of the only places in the world where you can go and not have to spend money. There’s no greater feeling of abundance when you’re pinching pennies than walking into a library, knowing you can have whatever your little heart desires. So don’t feel like you need to buy these books. Go to the library, it’s a magical place.

Here we go.

Burnout: The Secret to Unlocking the Stress Cycle
by Emily and Amelia Nagoski

DID my therapist recommend this book to me when it came out in 2019? Yes, yes she did. But then a funny thing happened – a ton of people in my life also started talking about it. Friends, coworkers, podcasters. It was popping up everywhere. 

This is a book about stress, and how the way we think about stress is wrong. In the United States, a lot of the ways we deal with stress and talk about stress are focused on ignoring stress: we blow off steam; we work hard and play hard; we participate in “happy hours,” where happy just means a little bit drunk. 

This book is more interested with processing stress. Processing stress means feeling your feelings, allowing your body to release the physical sensations of tension, and returning to a place of peace and calm. Rather than pushing stress away, acting afraid of it, you embrace the sensations of stress in order to let them go. 

Or as the Nagoskis put it, “To deal with your stress, you have to complete the cycle.” 

They go on to describe how human beings can complete the cycle of stress: physical activity, deep breathing, positive social interaction, laughter, affection, crying, creative expression. 

Have you ever had an almost-car accident on the freeway? A near miss? Do you remember what happens after the near-miss? You might scream inside your car at the person who almost hit you, or call yourself names if you were the one who messed up. Your heart beats a mile a minute, adrenaline surges through your veins. 

And then, your body starts shaking. 

In fact, a lot of animals shake after they’ve experienced intense stress. It’s our body’s way of completing the cycle by burning off the adrenaline that makes our blood vessels contract, sending more blood and energy to your muscle groups in case you need to, you know, sprint away from a lion. 

But in our modern lives, our threats aren’t often physical threats. We don’t need to sprint away from predators. Most of our stress is mental or emotional – an abusive boss, expensive repairs to our car or home, a relationship or friendship breaking up. None of these things give us an adrenaline rush and make our body shake – but we still need the same kind of whole-body release. 

We still need to process and discharge our stress. 

This book goes into a number of ways to complete the stress cycle and keep going in the face of persistent stressors. If you’re feeling overwhelmed and stressed every day, start reading this book as soon as you can. 

designing your life: how to build a well-lived, joyful life by bill burnett & dave evans

This book is unlike anything I’ve ever read before. It’s a book about how to design the kind of life you want— 

NOT how to get promoted, make more money, find love, master parenthood, travel more, eat better, live forever, conquer the galaxy… 

Literally how to sit down and design a life that would align with all your most important values. 

The word “design” is used intentionally here. Bill Burnett is the Executive Director of the Design Program at Stanford, and he worked for years in product design for Apple and other Fortune 100 companies. His co-author, Dave Evans, is a co-founder of Electronic Arts (one of the biggest video game creators around) and he’s spent years forming the corporate cultures of major corporations, mentoring executives, teams and young adults on the very questions that would lead someone to this book. 

“What should I do with my life?”

They walk you through the same process they would use to design a product to help you figure out what features your ideal life needs to have. 

One of the first exercises you do is to rate your happiness in a handful of areas as though the score is a gauge—is your love gauge full? Your work gauge? Health? How about PLAY? 

Once you have a starting measurement of your happiness across those four areas, you set about figuring out what you value, what actually brings you happiness, what you do just because someone, somewhere, at some point said you should

“You can’t know where you’re going until you know where you are.”

They ask you to track which tasks in your life make you feel energized, and which make you feel drained. Because when you’re living parts of your life on autopilot, the first step is to notice that you’re living parts of your life on autopilot. 

I’ve definitely spent way too much time in my life doing things because I thought I should, or because it would make someone else happy, or because I didn’t want to look stupid or like I was losing something everyone else had. 

Staying friends with people who made me feel drained after we hung out, and convincing myself it was nothing. Taking jobs that weren’t a good fit in the long run because I needed a break from another terrible job but didn’t have the courage to let people see me struggling. 

It’s really easy to listen to other people talk about this stuff—the ways they’ve ignored their intuition—and convince ourselves that we’re not like that, we totally honor our true feelings and know what’s right for us all the time. 

But honestly, that’s bullshit. 

We all have areas of our lives where we let emotions take the wheel, instead of logic. Where we make choices based on what we don’t want, instead of what we do. Or in order to not lose something, instead of to gain something better. 

So if you’re looking for a little guidance around how to organize your thoughts, organize your feelings, and quantify your life—with the goal of actually being happy, and not just doing what seems to make other people happy—this book is a lifesaver. 

“A coherent life is one lived in such a way that you can clearly connect the dots between three things: who you are, what you believe, what you are doing.”

Drop the Ball: Achieve More by Doing Less
by Tiffany Dufu

This genius little gem of a book holds some incredible wisdom. Tiffany Dufu writes about sexism in the workplace and home life, how women can stop the tyranny of perfectionism, how to ask for (and receive) more support from a spouse, and how to be ruthless in our priorities rather than feel like we need to cross every item off our too-long to-do lists. 

The anecdote I remember the most from this book goes like this: Tiffany was drowning at work, and realized she needed to shift her priorities and ask her husband for more help at home. She asked him to pick up the dry cleaning one day, something she would normally do herself. But when she got home later that day, her husband was out meeting a friend for dinner, and she started spinning with anxiety and resentment – where were the dry cleaned clothes? Didn’t he know how important it was that she have a clean work outfit for a very important meeting the next day?  As she was in the middle of a pity-party about how no one helped her and how her husband didn’t really care about her success, the doorbell rang. 

Her husband had asked the dry cleaners to deliver the cleaned clothes. 

There’s a whole section about getting over “home control disorder” and delegating tasks to other people. The trick of it is – you gotta stop giving a shit about HOW they get things done. As long as its within your means, it doesn’t matter if your partner cooks dinner from scratch or orders a meal for delivery. It doesn’t matter if they fix the landscaping themselves or hire someone to help. It doesn’t matter if they find a different way of accomplishing the same end result than how you would’ve done it. Because in order to focus on your priorities, you gotta loosen the reins on the things that are NOT those priorities.

Some other highlights: 

“Just because you’re better at doing something doesn’t mean it’s the most productive use of your time.” 

This is equally as true in the work realm as it is in the home realm – just because you’re the best at writing social posts for your business doesn’t mean you couldn’t delegate it to a helper. Just because you can get the whites whitest or the towels the fluffiest doesn’t mean no one else should do the laundry. 

But there are things that ONLY you can do. When you’re building your business, only YOU can sit down and do the deep work of building a strategy, prioritizing which elements fit your values, and creating content or a product based around your personal expertise. That’s something you can’t delegate. Focus on that first, and figure out how to hand off, systemize or ignore the rest.  

“I’m asking you for help with this because you doing so will help me to live my passion and purpose.” 

Dufu calls this “delegating with joy.” In a nutshell, this is the difference between, “Can’t you PLEASE just get the groceries this week? How do you not know what we need??” and “Honey, if you can plan and shop for the groceries this week, I can use that time to work on my business and build a more sustainable, happy, flexible life for us and the kids.” (Or whatever.) Do you see the difference? In a word, it’s context. People don’t actually love it when you’re resentful and exasperated. People WANT to help you. By offering them context, you remind them that their help (even in something they don’t like doing), is serving a greater purpose. Their help provides great value and meaning to you. 

The flip side of that coin is that you gotta let go. 

You have to release yourself from the expectation that everything in your life should be perfect and that you’re the only one who can make it so. Are you (and any kids) fed? Is there a roof over your head? Are the lights still on? Everything else is just a detail. Most things we fear could happen don’t actually have long-lasting consequences. Cut yourself some slack. 

The obstacle is the way: The timeless art of turning trials into triumph
by ryan holiday

Okay, look, this is a book about stoicism. I have real mixed feelings about stoicism’s role in our current cultural moment, because it definitely seems like it gets used as a crutch by the kind of tech bro who would rather read Epictetus in the original Greek than talk about their feelings. 

How-Ev-ERR, I agree with a lot of ancient Greek philosophy. This book is a wonderful resource that takes elements of Marcus Aurelius and other stoics to create some guiding principles that would serve anyone well, regardless of the present era. 

Have you ever heard someone talk about how getting laid off from their job was the best thing that ever happened to them? The obstacle (getting fired) becomes the way (a door to a better opportunity). 

The first half of the book deals with learning to see the world through a different perspective. Through learning to control our perspectives, we can control our reaction to adversity. If you go around telling yourself you’re going to fail all the time, you just flat-out won’t see the opportunities for success that are available to you. He talks a lot about learning how to be calm and steady, see the world more objectively, and focus on the things you have power over rather than the things you can’t control. 

It reminded me a lot of the principles of radical acceptance. 

Radical acceptance is a principle in dialectical behavioral therapy that emphasizes accepting what is, and not judging it. You know those moments in your life when you screw something up, big time? You crash your car, break something that can’t be replaced, say the absolute wrong thing to someone who has the power to make your life difficult? 

It’s easy to beat ourselves up and say, “God, if ONLY I had done X, Y, Z differently! This never would’ve happened.” Radical acceptance is not berating yourself, choosing instead to say, “Well, that happened,” and focus instead on what you can do about it now

After all, you can’t bargain with the past.

If that framework of experiencing the world appeals to you, check out The Obstacle is the Way. It’s especially calming and centering if your life is in any kind of chaos or turmoil. Holiday explains the principles of stoicism with illustrations from real historical events, and laying everything out so clearly that thinking like a stoic feels like the easiest thing in the world. 

rise: 3 practical steps for advancing your career, standing out as a leader and liking your life
by patty azzarello

I’ve bought, no lie, seven copies of this book. I have the receipts to prove it.

This book was written for career-track women rather than business owners, but there’s so much good stuff in here. I purchased seven copies over the years just to hand them out to friends like Halloween candy. You got a promotion? PHENOMENAL! Here’s my favorite book.

Patty Azzarello talks about how to build systems and focus on the things that matter so you can free yourself from never-ending busywork on things that won’t actually move the needle. 

“No one cares how hard you work. It’s about results. Not taking vacations is not something to be proud of nor is it a precursor to great success.” 

I think reading these words was the first time it had ever occurred to me that hard work wasn’t something to aspire to. Obviously, everyone loves a “good work ethic,” but what she’s talking about is effort. Would you rather hire a house painter who tries really, really hard and takes three days to paint a room to your satisfaction? Or would you rather hire a house painter who’s so good at one they do, they can bring one other person and have the room painted, edged and cleaned by the end of the day? 

In this case, nobody cares about your effort. 

Being good at something means that it’s not hard for you anymore. And everything is hard when you’re trying something new. If you can get the same results in half the time using a different system, DO THAT. Because truly, hard work for hard work’s sake is just wasting time. 

And you don’t get “partial credit” as a worker or a business owner just because you tried really hard.

This is also the book that introduced me to the idea of getting above the work. Working hard is fine; building systems to help you rise above it is better. It’s the difference between cooking dinner every night from scratch, taking an hour out of your day to stand in a hot kitchen, or meal prepping on Sundays so you can just toss some pre-cut ingredients into an Instant Pot and go do something else for 45 minutes. Both deliver a tasty, nutritive meal. One just uses a system to make it a hell of a lot easier. 

There are three sections to the book: 

  • DO Better: Working the right way to have more impact 
  • LOOK Better: Standing out and developing your personal brand to be more visible
  • CONNECT Better: Build authentic connections with key people to grow and get ahead

All those things relate to issues that business owners have to deal with, too. How to prioritize what will have the most impact, how to develop a brand that stands out, and how to authentically network and promote yourself to succeed. 

I’d give you a copy, but I’m fresh out. 

playing big: practical wisdom for women who want to speak up, create and lead
by tara mohr

Tara Mohr is a leadership coach who helps women stop doubting themselves, step into their personal power and tackle their most ambitious projects. No matter where we are in our lives, we each have a different vision of what “big” might look like in our businesses – building a million dollar brand, making enough money to focus on raising a family, or finding work that allows you to make a living from your nomad van. In this case, big is whatever you want it to be.

In the book, she says, “Playing big doesn’t come from working more, pushing harder, or finding confidence. It comes from listening to the most powerful and secure part of you, not the voice of self-doubt.” 

You might also call that a calling or a purpose. 

I learned two amazing, related life lessons for this book, which have guided me well over the years. The first is that you cannot live your life seeking praise and avoiding criticism. You HAVE to rely on your own inner guidance to tell you what’s good and what’s not good. 

In my last job, I had a client who was mercurial as hell. One day, she would love everything we were doing, buttering my team up with kind words. The next day, she would trash the very thing she had praised the day before. The jury is still out on whether or not this woman is an actual, real-life comic book villain, but we talked about this concept a lot on our team. 

Knowing we couldn’t anticipate whether or not this client was going to like something on any given day, we had to rely on our own standards of excellence. 

There was just no way to anticipate what would make her happy! But because we had an awesome team of amazing people, we damn well knew when we were doing excellent work – because we all held ourselves to high-but-achievable standards and collaborated extraordinarily well. 

That client later fell into a ravine and had her face eaten by a mountain lion. (In my head cannon, at least.)

The second, related concept is that when someone gives you feedback, they can’t tell you about you. They can only tell you about themselves. 

When your mom tells you she hates your new short haircut? She can’t tell you that your haircut is objectively bad or ugly. All she’s telling you is that she prefers long hair. 

The catch, though, is that this is true for both criticism and praise. When your mom tells you that you look so pretty in a floral dress, well, she can only say that she likes you in a floral dress, not that your husband or girlfriend or partner or pageant judge will think you’re pretty, too. 

On a practical level, what this means for a small business owner or solopreneur is that you’ve just got to follow your own internal compass. 

Feedback from your social followers or your customers or clients can only tell you so much. So don’t listen to the relentless critics. But don’t listen to your mega-fans either. 

Constructive criticism has a place – by all means, ask what your customers might want more of, or how you can serve them better – but at the end of the day, nobody’s praise or criticism can tell you anything more than what they like or don’t like. 

And spending your life trying to keep someone else happy doing stuff you don’t believe in is a fast-track to misery. 


set boundaries, find peace: a guide to reclaiming yourself by nedra glover tawwab

There was a discussion about boundaries on Twitter a few months back and a lot (a lot, a lot, a lot) of people really seemed to struggle with the distinction between a request and a boundary. And that makes sense, because our culture is designed to trample over the boundaries of a lot of people. 

Did your boss say something kind of skeezy? Don’t speak up and make him uncomfortable. Does your drama-loving friend expect you to spend an hour a night talking to her about her horrible dating life? Suck it up, you wouldn’t want to be a bad friend. Feeling sick and need to go home? No you don’t, we need you here. 

Nedra Tawwab is someone you might know if you’re on Therapy Instagram at all. She’s’ a licensed therapist and relationship expert who creates social media posts about how to be a healthy, well-balanced person. In the book, she covers six kinds of boundaries and how to create them – physical, sexual, intellectual, emotional, material and time.  

When you’re building your business, boundaries are important, both with what you will do and what you won’t. 

For example, you might set a boundary to stop working at 5:45 every day so you can make yourself a delicious, healthy dinner as an act of self-care. Or you might set a boundary that you’re not going to worry about any social channels other than Instagram until you get really good at that. 

The difference between a request and a boundary can be huge, and I know a lot of people really struggle with holding their boundaries. 

A request is something you ask of someone. A boundary are the terms you set around your needs. 

“Can we please order something other than pizza this weekend? I’m so sick of it,” is a request. 

“If you order pizza again this weekend, I’m not going to join you for our movie night. I’d rather go out with friends to grab some different food, I’m really sick of pizza,” is a boundary. 

In one, you’re asking someone to honor your needs. In the other, you’re honoring your own needs by setting your terms and sticking to them. 

“The hardest thing about implementing boundaries is accepting that some people won’t like, understand, or agree with yours. Once you grow beyond pleasing others, setting your standards becomes easier. Not being liked by everyone is a small consequence when you consider the overall reward of healthier relationships.”

Honoring your own needs is a cornerstone of good mental health. If you struggle with setting boundaries, saying yes when you should say no, taking on too much, sacrificing much-needed rest, letting people push you around or struggling to speak your needs into existence, this book is for you. 

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I’ve spent 16 years in advertising, and now I’m using that knowledge to help creatives grow their own small businesses. Will that include you this year? 

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