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5 Books to Rekindle Your Freelancing Confidence Over the Holidays

Whether you’ve been freelancing for years or have only recently taken the plunge, it’s important to take a step back every once in a while and recharge your creative batteries. And what better time to do that than during the holidays? The following books are chock-full of the kind of inspiration freelancers thrive on. Not a bunch of self-help fluff, but real, hard-earned wisdom. They’ve been a great help to me. I think they will be for you as well.

Creative Confidence — Tom and David Kelley

You’re not going to find a more on-the-nose suggestion than this. Creative Confidence by Tom and David Kelley (the brothers behind IDEO) will help you find exactly that. Full of anecdotes and advice, this book debunks the myths surrounding fear, failure, and the fear of failure. The Kelleys write: “Creative geniuses, from artists like Mozart to scientists like Darwin, are quite prolific when it comes to failure — they just don’t let that stop them.… Their ultimate ‘strokes of genius’ don’t come about because they succeed more often than other people — they just do more, period.”

Werner Herzog: A Guide for the Perplexed — Paul Cronin

This long, strange book is culled from years of conversations between filmmaker Werner Herzog (Grizzly Man, Encounters at the End of the World) and editor Paul Cronin. While it centers on filmmaking, it reads like a manifesto for creativity of all kinds. Over his long career as a director, Herzog has learned the value of pushing himself into unknown and often frightening situations. It’s become a hallmark of his work. Spend some time inside his head, and you’ll come out the other side a more fearless creator. A sample:

“Always take the initiative. There is nothing wrong with spending a night in a jail cell if it means getting the shot you need…. Never wallow in your troubles; despair must be kept private and brief. Learn to live with your mistakes…. Carry bolt cutters everywhere. Thwart institutional cowardice. Ask for forgiveness, not permission. Take your fate into your own hands…. Walk straight ahead, never detour. Learn on the job…. Don’t be fearful of rejection. Develop your own voice. Day one is the point of no return…. Get used to the bear behind you.”

Steal Like an Artist — Austin Kleon

Steal Like an Artist is short and funny, and it hits like a hammer. It reads like an extended permission slip to be yourself and find inspiration all around you. Kleon writes, “Every artist gets asked the question, ‘Where do you get your ideas?’ The honest artist answers, ‘I steal them.’” Rather than getting all worked up about being “original,” Kleon encourages artists to simply be productive. Make things. Write things. When you stop worrying so much about being yourself, you suddenly become who you are. You’ll be able to read this one in a few hours, but I guarantee you’ll go back to it again and again.

Essentialism — Greg McKeown

Building a sustainable freelancer’s life is all about structuring your time. What is worthwhile? What isn’t? Often what feels like burnout or a loss of confidence is simply an imbalance of priorities. Greg McKeown’s Essentialism is all about gutting the fluff and spending time on what is truly essential. It’s not just the way to a good freelance life; it’s the way to a good life. In McKeown’s words: “Essentialism is not about how to get more things done; it’s about how to get the right things done. It doesn’t mean just doing less for the sake of less either. It is about making the wisest possible investment of your time and energy in order to operate at our highest point of contribution by doing only what is essential.”

Daring Greatly — Brené Brown

Overcoming fear does not mean overcoming vulnerability. In her brilliant book, Daring Greatly, Brené Brown argues that by making ourselves more vulnerable, we can unlock our true creative potential. Stepping out there might be frightening and painful, but it’s nowhere near as painful as shying away from what we’re truly meant to do with our lives. “Vulnerability sounds like truth and feels like courage,” Brown writes. “Truth and courage aren’t always comfortable, but they’re never weakness.”

Do yourself a favor and dig into one of these books over the holiday break. I think you’ll find the inspiration you’re looking for.

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