The Transformation Book Club: Career Edition


What should you read if you want to dismantle your whole career?

A strange question to ask. But I started asking it a year ago, prompted by a variety of soul-shaking events in my life, which ended in me leaving my job and city

One of the hard realities I started facing was the fact that while I had been successful in my job, and there were elements of it that I truly loved, the overall life I had with my work was not working for me. I was overwhelmed and exhausted much of the time. (Am I hearing a chorus of “Amens” out there?) My health was suffering, and chronic stomach woes had taken over most of my days. It took nearly all of my weekends and vacations to get myself back to even zero baseline, physically and sometimes mentally. When I went on vacation, I felt the distinct sense that I had been holding my body tensely while walking on a tightrope, and only now while on vacation could I relax and breathe again.

I was a middle school teacher. I loved my students dearly, and I built an arts program from the ground up. But I was constantly in deficit (time, energy, rest, and health), and I was making far less than I ultimately felt I was worth.

But taking a good, hard look at that, and admitting that perhaps I what I really wanted was something else, was very, very hard.

As part of the Transformation Book Club series, I want to share with you some of the reads that helped me as I wrestled with changing careers. It’s still a work in progress, but after reading a lot (my strategy: get everything on Audible and plow through these while commuting to work or other mindless daily task), here are some of my picks.

The Way We’re Working Isn’t Working (Tony Schwartz)

This was a game-changer for me. Well, it didn’t so much change my game as it put words to exactly how I feel about our paradigm of work in this culture. If you’re struggling with work-life balance in any way, this would be my #1 read. My biggest takeaway: we as humans are not designed to work non-stop for eight hour days. We are not designed to go long stretches without breaks, we are not designed to spend our days at desks, and we are not designed to multi-task. We are not only healthiest but also more productive when we can focus deeply on one thing for 90 minutes stretches, interspersed with mental and physical breaks. This is something I feel passionately about, and I will stand on my soap box to promote a paradigm shift on this in our work culture.

Originals: How Non-Conformists Move the World (Adam Grant)

If you’re one of the “originals” Adam writes about (see my review of his other great book, Give and Take here), you chafe against the notion that success means you walk the traditional path of education, get a good corporate job, and tow the line working 40, 60, or 80 hour work weeks for a fat salary and security. If you’re a creative and you want to think big (and weird), read this.

Leap First: Creating Working that Matters (Seth Godin)

In a similar vein, Seth Godin is the brilliant writer, sage, and influencer whose work is inspiring those of us who want to do profound, meaningful things that go against the traditional grain. I read a bunch of Seth this past year (including Tribes and The Icarus Deception), and I flat-out loved everything. I had the sense with his writing that someone wrote a book directly for me, that spoke to exactly what I was thinking and feeling at this juncture in my work life. He’s incredibly inspiring. Biggest takeaway: we need to define “making art” as making work that matters and touches people. We need to think and act boldly to do that, and we need to “ship our art” and put it out into the world.

Start Something That Matters (Blake Mycoskie)

Get this on audiobook and listen to Blake’s calming Southern drawl. It details the story of how he started TOMS shoes, and it shows that a model of social entrepreneurship really works. TOMS was one of now many for-profit companies that have a model for giving back built in, which can be both good for business and good for others.

The 4-Hour Workweek (Tim Ferriss)

OK, so I was kind of late to the game on this one. Ten years out, it’s still a bestseller that has changed a lot of people’s lives around how they think they can live and work. While the title is kind of a sensationalist hook, what Tim really writes about is how it is possible to leave the model of 40-hour (or 60… or 80…) office work week behind. This book really changed my thinking around what is possible for the way we structure our life and work, and I’ve since become a big fan of Tim’s other work (the podcast is great). Biggest takeaway: the most precious resource — and measure of true success — is freedom of time. If you can structure your life and work such that you get more time back to pursue the things that bring you joy and peace, you have truly won the game. Tim also advocates for the flexibility to work from anywhere, which brings us to…

Vagabonding (Rolf Potts)

I read this because Tim fanboys on this one, having been very influenced by Rolf’s philosophy of “lifestyle design,” whereby you get not only time freedom but also geographical freedom to travel and work from anywhere in the world. The idea here is to structure your work so that you you don’t have to defer all the fun experiences you want to have until retirement. You establish geographic flexibility, and then you optimize productivity so you can take “mini retirements” in between work stints. While I’m not really planning on backpacking around the globe with one pair of underwear, I do love travel and I have reached a point where, more than anything, I want that flexility of time and place. 

The War of Art (Steven Pressfield)

This came highly recommended by many authors and podcasters I consumed. Steven Pressfield is a writer who had meager external or financial success with his writing for many years. (He authored The Legend of Bagger Vance, which of course went on to do just fine.) His main point is that the biggest challenge as a writer (or creative, or entrepreneur, or whatever brave, unconventional thing we are doing) is showing up every day to just do the work. Honestly, it’s hard. It takes a tremendous amount of discipline and stubborn stick-to-it-ness to forge ahead with your own work and Just. Do. It. Every. Day.

Big Magic: Creative Living Without Fear (Elizabeth Gilbert)

Liz Gilbert talks about a similar thing in Big Magic. I love Liz and her way of marrying down-to-earth humor with a spiritual curiosity. A lot of this books speaks directly to writers, but there’s a lot of good stuff here about what Liz calls “creative living.” Are you a person who chases having more creativity, happiness, joy, and “aliveness” in your life? Read this. Also, Liz is brutal in her reality check of not making art to make money. It just may or may not come out of your art. You have to want to do it anyway. Which is how I find myself contemplating data science bootcamp to marry a lucrative tech skill to my skills as a teacher, writer, and artist…??

The 10% Entrepreneur: Live Your Start-Up Dream Without Quitting Your Day Job (Patrick McGinnis)

For those of you who are like, “Girl, that all sounds like a nice pipe-dream fantasy of globe-hopping freedom, but there’s no way I can quit my job right now,” I offer you this. A great read on how to structure your “passion project” work while still maintaining the day gig, and optimizing the side hustle over time to become a second income stream, or even a full-time thing.

Of course, I kind of ended up quitting my job and leaving my apartment behind in one fell swoop, so I’m not sure I totally took Patrick’s advice… but I am a practical girl too and realize that sometimes sweeping change happens in small steps. :)

Share your favorite reads and resources on careers (books, podcasts, websites, etc) with me here.

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