Gift Guide: Book Recommendations for your Favorite Entrepreneur

I’m constantly buying new business books (my accountant teases me for my endless purchases) and listening to podcasts & audiobooks in my car (my poor toddler son will be talking about sales funnels & positioning by kindergarten). It’s no secret: I’m a giant nerd.
So when a friend recently asked me for a list of recommendations to share with her husband for Christmas recommendations, I got really excited. And the list quickly got quite long.

So I figured, instead of overwhelming her poor husband with an insanely long Google Doc, I’d write 2 blog posts to share my recommendations — the list below is full of many of my favorite business books on 4 topics (setting yourself apart, optimizing your offerings & life, creating a positive mindset, and learning design & online strategy) and don’t miss out on part 2: a post with all my favorite planning tools, food gifts, and self-care products.

It’s no secret: I’m a giant bookworm. A friend recently asked me for recommendations, so I'm sharing so you can also enjoy these great business books too!

Affiliate Disclaimer

Many of these books are listed with affiliate links, meaning that I will get a small commission if you buy from the link on this page. I would recommend these books even without the potential payment, because I have read them all and learned something from each of them.
Also, in a few spaces I recommend the audio version of the book; I’ve been an Audible Gold member for years to build this library. If you’ve never tried Audible, you can try 2 Audible books for free

So without further ado, here we go:

Finding your unique business positioning

One of the most important steps to starting and evolving your business is to figure out what makes you different from other businesses in your industry, then using that knowledge to structure & sell your services. Here are some great resources to determine what sets you apart & how to capitalize on that:

The Conquer Kit by Natalie MacNeil

This book is an incredible overview of all the things you need to get organized to start your business, and goes over the order to complete them in so you don’t get overwhelmed. Figure out your approach, determine what you’re selling, get your legal & financial affairs in order, come up with a marketing plan, hire a team, build a vision and develop a 12-month plan for implementation.

If you have an aspiring entrepreneur in your life, this is the book to help them get everything up & running.

Your Business Sweet Spot by Racheal Cook

If you’re just starting out your business and want to figure out how your personality can direct you to the right business model, this is a great jumping off point. Racheal begins with a quiz that helps you find your “sweet spot archetype” (options are maker, maven, mentor & mastermind); once you know this, she goes over how to validate your offerings and getting them into the hands of your target audience. She covers a lot very quickly!

Quiet Power Strategy by Tara Gentile

As a business strategist, Tara’s seen a LOT of formulas about how to get rich quick, and she’s a little tired of hearing people yell about what worked for them. She takes a tailored approach: find out what makes you unique (she calls this your “quiet power,” because you don’t have to scream to be heard when you know what you do best) and then make your plans based on what you do best, not based on what worked for someone else.
An empowering book about creating your own leadership instead of following someone else’s formula.

Make a Killing with Content by Lacy Boggs

Maybe you want to start a blog. Or maybe you have one but you’re not seeing any new leads or sales come out of your blog posts. Either way, this book can help you blog with a purpose: to use your blog to strategically guide people to buy from you.
This book is short (67 pages), affordable (less than $1 at the time I’m writing this!), and packed full of actionable steps. An absolute must if you want to be a more focused blogger.

Optimizing your business to balance your life

Your business is up and running, great! Below are some resources to allow you to balance your business with your life:

The Sweet Spot: How to Find Your Groove at Home and Work by Christine Carter

If you feel like you’re stretched thin & have to choose between growing your business and spending time with your family, you’re not alone. The internet is full of conflicting advice to fix this — delegate! prioritize! multitask! work more! work less! — that can lead to more overwhelm & exhaustion.

Thankfully, Christine Carter is a a happiness expert at UC Berkeley’s Greater Good Science Center, and she looked at all the research to determine some strategies that helped her balance her work and still spend time with her teenage step-daughters. A lot of this is tied to creating & automating new habits (which create new paths in your brain the reinforce good behavior) to create optimal workflow without making us feel depraved.

Delivery method: I recommend listening to this as an audiobook. It’s read by the author, who adds a lot of emotion and action into her delivery.

Re-Work by Jason Fried and David Hansson

This is my go-to book whenever I feel stuck in a funk & need a kick-in-the-ass. It’s easy to pick up, skim, and put down, because it’s essentially a series of snappy blog posts with memorable illustration.
Here’s one of the sections I have dog-eared so I can pop it open as a quick reminder:

Unless you’re a fortune- teller, long- term business planning is a fantasy. … Writing a plan makes you feel in control of things you can’t actually control.
Why don’t we just call plans what they really are: guesses. Start referring to your business plans as business guesses, your financial plans as financial guesses, and your strategic plans as strategic guesses. Now you can stop worrying about them as much. They just aren’t worth the stress.

Check out some excerpts to see what I mean about the cute illustrations & quick chapters.

Delivery method: Definitely get this one as a paperback. I bought the audiobook first & it just wasn’t as satisfying without the drawings & ability to consult it quickly.

Business Brilliant by Lewis Schiff

What makes millionaires different from middle-class? Lewis Schiff explores this in great detail, including how wealthy people ask for more money, delegate tasks that they don’t love, and they take advantage of opportunities.

The book is full of great storytelling to explain these concepts: how Bill Gates became successful, not because he was the best programmer (he certainly wasn’t) but because he found ways to position Microsoft smartly in the market and work with manufacturer demand. How a hospital automated their processes to decrease their mortality rate practically overnight. How Richard Branson built his business by focusing on vision, not execution.

Delivery method: I accidentally walked 5 miles one day listening to this audiobook, because the time passed so quickly & I was so enveloped in the storytelling & lessons. (My dog LOVED this book for that reason!) But I also wish I had a physical copy so I could reference the 17-step process outlined in the final chapter. So either delivery is wonderful in its own way.

The Brain Audit by Sean D’Souza

Ever wonder why customers buy at certain price points, and ignore it at others? Or why some sales pages are incredibly successful, and others tank? Or why pushy sales people make you feel skeezy?

This book really digs into customer psychology, studies the decision-making pattern that we use everyday, and helps you find ways to discover what you’re doing “wrong” and improve your customer experience.

Delivery method: Definitely get this as an ebook. The audiobook has weird noises between chapters that are super distracting.

Overcoming challenges and developing confidence

Back in my days as a salaried employee, I had a boss to tell me what to do. She set my priorities, created boundaries, and gave regular evaluations.
But now that I’m self-employed, I don’t have anyone to give me the rules. And while that can be empowering, it can also be terrifying, leading to self-doubt & confusion. (Especially since the internet is full of people screaming about “if you just follow my simple plan you’ll make six figures in 20 minutes!”)
Here are some resources to move through the fear, determine what works for you, and be successful … whatever that means for you.

Get Rich, Lucky Bitch by Denise Duffield-Thomas

Denise’s online course Lucky Bitch Money Bootcamp was a total gamechanger for me, as I discovered all the ways that I was holding myself back from success because I was too afraid of what I’d have to sacrifice to be financially successful. (Could I make money without working 80 hour weeks? Would people resent me if I made more than them while working less?)
But Denise turned my belief around, teaching ways to re-adjust the way I think & behave in order to create the life I love, without working all the time and still having plenty of time to spend with my family.
This book is an abridged version of the course for a fraction of the price. Get a free chapter to find out more about her approach.

The Desire Map by Danielle LaPorte

I listen to The Desire Map every December, as I plan for the year ahead. Instead of focusing exclusively on the milestone goals to achieve (which are important — I’ll get to that in my “products” post which has a whole section on planning tools), I reflect deeply on how I want to feel. Because what’s the point of making millions of dollars if it leaves you feeling stressed, overwhelmed, and burned out? But if you focus on your “core desired feelings” as Danielle calls them, your victories will be sweeter because you won’t be chasing goals that don’t fulfill you:
You’re not chasing the goal itself – you’re chasing the feelings that you hope attaining those goals will give you.
For a hyper-abridged version of this book, you can download the Ultra-Lite Version for free; in that document you’ll find a coupon code for 20% off if you want to buy the full Desire Map book or workbook.

Delivery method: This book is the reason audiobooks exist. Danielle is clearly a poet, and her soulful way of speaking helps the lessons she’s teaching sink in. The book is good, but the audiobook never disappoints.

Daring Greatly by Brene Brown

There’s a reason that Brene Brown’s vulnerability presentation is among the 10 top-viewed TED Talks of all time: It’s really scary to share emotions and put your genuine self into the world. Brene shares detailed insights from her academic research about courage, shame & vulnerability without getting too jargon-y; she writes in the way of a natural storyteller, and is engaging, deprecating and non-judgmental.

Delivery method: I have this as a hardcover & an audiobook, and love it both ways.

The War of Art by Steven Pressfield

Pressfield is primarily a novelist. In his early writing, he used to wait until “inspiration” struck him, which would leave him with large gaps of time without writing, feeling like a failure because his “muse” had left him. But he discovered that by just sitting down to write, every single day, his writing started to change. His “muse” was more likely to appear, his writing became better & more consistent, and the words began to flow onto the page. It wasn’t always easy to sit down at his desk — there were always distractions & excuses — but he found that as long as he sat at his desk every day and tried to write, the “inspiration” would eventually arrive.

The 3-word summary of this book, then, is “Do the work.” Pressfield speaks in this book to creative entrepreneurs who may be waiting for the iron to be hot in order to strike, but he discourages this “wait and see” approach. Essentially, if you wait around for your business to grow itself, you’ll be waiting a long time; but if you “do the work” every day, you’ll start to see subtle shifts in the way that your business grows.

Design, strategy & user experience

Design is a Job by Mike Monteiro

Mike was my introduction to the business of design, as I binge-listened through his podcast Let’s Make Mistakes and discovered his presentations, the most famous of which is the popular F— You, Pay Me.
In this book, he gives advice about the client services side of design: how to communicate well with your clients, set clear expectations, and not get steamrolled by clients who want to pay you nothing in exchange for your blood, sweat & tears.

Think like a Digital Strategist by Marie Poulin

Marie is my design mentor, through her program Digital Strategy School (which will be opening again in January, get on the waitlist!), which totally transformed by thinking about design from “let’s make something pretty” to “how can I help my clients solve their problems and move through a process smoothly?”
This book is an introduction to many of the goal setting and customer experience exercises included in DSS, and a great overview of the kinds of things that every business owner should be tracking & measuring to see their businesses grow.

The Strategic Designer: Tools & Techniques for Managing the Design Process  by David Holston

Once I realized that “being a designer” was more than “making pretty things,” this book helped me figure out the workflow & processes of setting up my workflow & thinkign about the client experience. It covers a lot of ground, starting with research, then concepts, mockups, and delivery of finished products. And most importantly, it talks about how to make this process smooth & enjoyable for the designer AND the client.

If you’ve started a design business but are struggling with getting your systems to run smoothly, this book is a great resource to help you learn Best Practices and incorporate them into your own business.

Universal Principles of Design by William Lidwell et al.

This is an amazing introductory primer into many areas of design, and each topic gets a 2-page spread: the left page is an explanation of the concept, the right page is examples & practical applications. Because each topic has limited space, this really serves as a high-level overview of lots of types of design and makes connections between how they fit together.
If you’re just getting started in “design” and want to figure out which parts interest you most — workflow? user experience? psychology? accessibility? — then this book is a great way to figure out what to read next.

Delivery method: This book is best in print, not kindle or audiobook, because of the unique 2-page layouts.

Make sure to check Part 2 of this series: my favorite planning tools, food gifts, and self-care products.

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