How to Take a Vacation When You Work for Yourself
Self-employed? Taking vacations is essential, and easy to pull off if you plan ahead, communicate, and stand your ground.
I carry a book most places I go. I’m the first to “go to a book” when I have a question and want to learn something new, and my transition to freelance work was no exception. Since then, I’ve padded my bookshelf with books designed to help me create routines, organize my ideas, and build this new life.
Check out these reads to spark your own imagination and help you do your best work. Just getting into the game? Download Fiverr Workspace’s “Welcome to Your Independence,” a free playbook for the newly-minted self-employed hustlers among us.
“Do Cool S**t,” Miki Agrawal
Serial entrepreneur (of WILD and Thinx) Miki Agrawal’s book came along at a point where I was getting ready to consider taking the leap away from my full-time job. Her no-nonsense approach to not only taking that leap, but building my parachute on the way down, was essential to some of my first creative marketing efforts.
Miki’s approach isn’t for the faint-hearted by any means, but it serves as a great nudge out of your comfort zone when considering if freelancing could be right for you. For the more established freelancer, “DCS” could serve as an excellent booster, a reminder of the energy that you first started out with.
“Real Artists Have Day Jobs,” Sara Benincasa
I was drawn to this book after reading the title essay, an incredibly encouraging dispatch about trusting yourself to make things you may only dream of. The rest of the book is comprised of 50+ essays on topics of personal wellness, prejudice and bigotry, and even housekeeping (one that I continue to revisit, especially now that I work from home).
Sara’s own journey as a freelancer is a varied and prolific one, and this book is a great reminder of just how much power we have to shape our own personal, emotional, and professional lives when we choose to accept the title of “real artist.”
“Give and Take,” Adam Grant
“Give and Take” is billed as a business book, but actually illuminates a life philosophy that has served me well when finding, interacting with, and collaborating with clients. Grant’s book introduces readers to the concept of “givers,” “takers,” and matchers,” and explains the benefits and disadvantages of each orientation toward life.
As I connect with new people in my travels and through marketing, I can’t help but assess each new relationship through the lens that Grant introduces; it helped me reevaluate how I work with others, seek out collaborators, and continue to build my social and professional networks.
“The Freelancer’s Bible,” Sara Horowitz
This one’s a gimme. Sara Horowitz, founder of Freelancers Union, released this companion guide to the website in 2012 as a how-to guide for the newly minted independent worker. Addressing all stages of the process from establishing your business and getting work, to growing and managing it, it’s an easy-to-read comprehensive guide to this world of work. Freelancing can often feel difficult to navigate; “The Freelancer’s Bible” often helps provide me much-needed stability and direction.
“Everything I Know,” Paul Jarvis
After following his blog and newsletter, I raced to pick up Paul Jarvis’s book about how to build a creative career on one’s own terms. Paul’s straightforward and occasionally coarse style isn’t for everyone, but he counts on that—his “rat people” (his term for the tribe you build through a common understanding of your work) are the ones for whom he creates, and he advocates building similarly unique niches in your work.
My greatest takeaway from Paul came in his discussions about managing fear and anxiety in the freelance world. His saying “fear and action can exist in parallel” has given me far more comfort than he knows; for the freelancer stuck in one place by fear, I highly recommend Paul and his writing. He’ll snap you right out of it.
“Essentialism,” Greg McKeown
As a freelancer who speaks, writes and podcasts, I tend to get bogged down in a lot of clutter. Emails, writing assignments, networking events, requests for connections, and the like. I worried as I started freelancing about my ability to manage all those things. What would I say yes to? What would I say no to? Would I miss good opportunities if I said no?
Greg McKeown changed all that for me. His philosophy on essentialism isn’t about which things you’ll say yes or no to, as many other books in this vein often do. Rather, he writes about building a life that prioritizes what’s essential to who you want to be and what you want to do, and turning down the rest. Seem simple? It is, and isn’t—Greg will elaborate on it. I’ve spent a great deal of time with this book, and its holistic approach to creating a life that leaves you feeling in control has been invaluable to me.
This list is far from complete; what books would you add to it?
