getting the courage to quit your day job

*Editor’s note: We are so happy to have Eleanor back on Dear Handmade Life for her intuitive business tips and advice. We especially love this post because eleanor gets personal as she talks about her own struggles to make her full-time job be doing what she not only loves but is great at!

-nicole s.


The original title I proposed for my first book was, “Grow: How to Take your Do it Yourself Project and Passion to the Next Level.” When Joe, my book publisher suggested we add “and quit your job!” to the end of the title my first response was protest, “I can’t quit my job! I need health insurance!”

I have worked full-time since the day I graduated college. Over the past ten years I built a career working for arts organizations and with creative people, helping them actualize their projects. In my professional roles I honed much of the time, money and business management ideas wrote about in Grow.

However, as Grow’s June 1, 2013 release date approached and I threw myself further into the world of creative entrepreneurship that is the book’s focus, I felt an inkling that it was time for me to move on, employment-wise. But something was holding me back. I started to make a lot of excuses. Despite being surrounded by people who had made a career change or quit their jobs to pursue their passion I was still unsure if I was up to the challenge.

The idea of quitting my job and pushing myself into the freelance world was a big risk. It meant confronting my fears, expectations and hopes for myself around work. Some of those fears were:

Money. How would I earn enough? Freelance involves finding clients who would pay me fairly to do the work I love. It also means paying for my own insurance, a higher percentage in taxes, and trying not to run through all of my savings.

 My sense of self-worth and value. Though American culture celebrates entrepreneurs and creative ingenuity, it also places a huge amount of value on employment status. Being gainfully employed provides you with external, society-proven proof of self-worth.

Focus and direction. My work with Grow had opened up a new pathway in my career towards entrepreneurship and business development and I wanted more time and space to explore it. However, a new direction is a step into the unknown and can feel like an unfocused free fall.

Over the past year I have slowly addressed these fears. I’m proud to say that at the end of September I took the plunge! I began a part-time, freelance event planning gig and have been writing grants and teaching workshops as well. While I’m still unsure of what the future holds, most of the time I feel excited about what’s next. I wanted to share a bit of my process here because I hope to create meaningful conversation and connections around the challenges, and rewards we face when following our DIY business (and life!) dreams.

In January of 2013 I set my goals and intentions for the year. I knew that in order to pursue the independent and creative life I desired that I would need to consider working for myself. To finally make this leap I took a thorough look at what I needed to do to make that possible:

I got a handle on my personal finances. I took several months to really understand how much money I needed to make to live, save and pay my bills. I also readjusted my spending habits and moved away from conspicuous consumption. Now, I’m not only in the habit of saving and documenting my receipts for tax-purposes, but I have confidence to make decisions about how much I need to get paid from my freelance jobs to cover my expenses and save a little as well.

I activated and cultivated my support network. I made it a habit of networking with and talking with people I admired and respected who had made a similar career transition, worked in a field I was interested in, or were pursuing their dream project. I also set up a regular, monthly check-in with a friend who is making a similar career shift. We talk regularly about how are goals are evolving and what concrete tasks we need to accomplish to move towards them. I call her my “accountability partner,” but she is also there to support me emotionally as I navigate starting a new, professional life.

I acted with diplomacy. It’s tempting to get all “Office Space” and envision quitting as a triumph over an oppressive system, but in reality my decision to leave my full time job was a natural evolution of my own career process. I approached my (now former) employer with an attitude of, “How can I help you as I make this transition?” Because I valued them and my role there they asked me to stay on part-time for an additional month to help wrap things up and I felt I could move forward knowing I had been responsible and ended my job on a positive note.

I worked to accept that there would be a transitional period. I knew I couldn’t go from full-time work to freelance rock star over night. I’m still in a period of exploration and haven’t found solid footing. I constantly remind myself that the reason I chose this path was to give me room to explore career-wise. I need to accept and learn from the discomfort that comes with that.

Taking the leap into freelance is a proactive step in a new direction for me.

Who else has made a similar transition? And how did you plan for it and cope with your hang-ups? Personally, despite my fears, this is a career move I’m celebrating, inviting my network to celebrate with me, and making my exploration process public. I’ll let you know where I end up!

-eleanor whitney

About Eleanor:

Eleanor Callott Whitney is a writer, rock musician, educator, and arts administrator raised in Maine and living in Brooklyn. She finds joy in bringing order to the chaos of creativity, empowering artists with the tools they need to think of themselves as entrepreneurs and in managing and facilitating creative projects with panache. She is the author of Grow: How to take your DIY project and passion to the next level and quit your job! and writes extensively about art, culture and nonprofit management. She published the personal, art zine Indulgence for 15 years, as well as co-founded the Portland Zine Symposium and has worked for the New York Foundation for the Arts, the Brooklyn Museum, and P.O.V./American Documentary. She is the proud recipient of a Master’s degree in Public Administration from Baruch College where she learned to stop worrying and love statistical and budgetary analysis.

eleanor whitney


  1. Thank you for the good advice, Eleanor. It was great to hear about your fears and how you addressed them. Many blog posts just urge you to follow your passion and quit your day job without addressing the real-life challenges we face, such as healthcare. I’ll be checking out your book right now!

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