Day Jobs & Creative Entrepreneurship

The Day Job Desk(Note: This piece is excerpted from this podcast)

Recently I’ve received a lot of questions about creative living and the day job. Maybe it’s because after the holidays everyone’s back into their regular routine and feeling it. I have a lot that I want to share about what it means to live a creative life while being in our regular jobs but I want to start the exploration from a bit of a different angle: creative entrepreneurship. I want to start there because it seems like these two concepts have become inextricably linked.

It’s as though creative entrepreneurship is the light and the day job is the shadow – but that’s not the whole picture.

If it’s right for you, creative entrepreneurship is gorgeous, inspiring and deeply fulfilling. It’s also gruelling and heart-breaking and brave.

Creative Entrepreneurship: The Myth & The Beauty

There’s a powerful myth being shared again and again and again (and by “myth” I mean a powerful story that represents something compelling in our collective unconscious) and that is the story of the creative entrepreneur. It tells of a stifled, creative soul who works in a dreary unsatisfying world of grey, longing beyond longing to strike out on her own, to pull all the colourful threads in her heart out into the world so she can weave them into a magnificent tapestry and share them with the world.

This part of the story is profoundly familiar. It has the ring of truth because it is our story. We are creative souls. We have experienced being stifled. We know what it is to live in a world of grey when our hearts beat in full colour. Yes, this is who we are and this is our longing.

And so we want to know, what happens to this creative soul? What’s next in her story (and our own)? How does she come to share her creative heart? In our current landscape the story is that she becomes a creative entrepreneur.

I love the story of the creative entrepreneur. I’ve lived it. I help other people to live it. But I often think that in the popular telling of this myth, the tale  has lost its teeth. Instead of the creative spirit becoming a hero who goes through trials and tests in the service of her quest, facing losses, victories and dragons along the way, all the while becoming stronger, all the while becoming who she is meant to be, instead she becomes a Disney princess.

In that version of the story, the creative entrepreneur tucks herself away in her castle, delighting in creative pursuits, every now and then dipping her toe into the pool of the world, offering a rare and precious gift she’s created which is embraced immediately and enthusiastically by her people who then shower her with love and abundance so she can remain happily ever after playing, imagining, creating and Instagramming it all.

No wonder we all want to do that! No wonder we get it in our hearts that this day job chains our soul, has us sorting peas like Cinderella! But one day, if we’re good, someone will see that we’re special and we’ll go to the ball, right?…..Right?

Trust me, I’m not denigrating this story. I love this version of the story. I love immersing myself in its magic, particularly on Pinterest and in Stampington & Company magazines! It’s the story of our longing and our dreams and it is beautiful.

Creative Entrepreneurship: The Myth & The Heartbreak

But it can also be pernicious.

We start to believe that if everything isn’t magical and shiny and fast and abundant, than creative dreams aren’t for us.

We start to doubt ourselves, thinking, “Oh, maybe I’m not a creative soul after all. That glass slipper isn’t for me or people like me. It’s only for people like her.”

We sign up for program after program investing more dollars than we have in hopes that this teacher this time will be our fairy godmother and get us into the ball.

And even if they do, what a heartbreak to get there and discover not a Technicolor palace but instead the hard slog of endless work – some meaningful, some tedious, some frightening – that you may or may not get paid for.

Maybe that day job isn’t all shadow and creative entrepreneurship isn’t all shine.

I can tell you that in my story creative entrepreneurship has brought me much fulfilment and delight. My days are warmed by creative fire! I’m generating ideas, content and classes all the time. I am exploring, wondering and bringing things to life. I fill my days with writing, recording, books,  conversations, music, yarn, art and my camera. I believe deeply in the work and I know it makes a difference and that gives me a profound sense of meaning and purpose.


I have also felt beaten down when I’ve failed – and that’s plenty of times. I’ve been exhausted by the workload, mortified by missteps and hurt by being left out and critical feedback. I’ve sobbed in desperation having no idea what to do next and felt so alone in having to decide. I’ve offered up my heart and had absolutely no response. I’ve had times when I’ve invested more money than I’ve made. I have worried, obsessively, about whether what I was doing was right or good or going to work at all.

I am not saying this to discourage you.

I’m not saying this to shatter entrepreneurial dreams. I believe in them – and in you – with my whole heart. I’m saying this to try, as best as I can, to tell the whole story, at least the Jamie version of it. Yours will be yours, whatever you choose to do.

I am saying this because here is what I know:

You are a heroic creative soul. And your story will not be like anyone else’s. Your story is your own and it must be lived and breathed and experienced and created by you. That is what creative living is all about.

Wherever you are, whatever you do, whatever your situation, creativity can be a breath of fresh air, an awakening whisper, a wild dance, a deep roar in your life and in you.

You can be creative every day because that’s your birth right. It is who you are and what you’re designed for. Discover the path that is right for YOU!

Live your own story.


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  2. CLP says:

    Jamie – This is fabulous, deeply beautiful, and necessary. I think many (most?) of us feel like we want the Disney version, and I’ve been witness to your knocking out your creative entrepreneurship week-in, week-out for at least 5 years now. And what you show me (repeatedly) is that just by showing up, you bring the energy, you make the thing. Thank you for showing up every day, in all of your stellar ways.

  3. I love this, Jamie! I’ve absolutely lived it, and have such a clear vision of what it’s like from many angles. There is value in ALL of our work. Even the grueling parts, even the parts we really don’t like doing … do they bring us income that allows our heart to create into the wee hours of the morning? I have regained balance, and love that I use all parts of my brain to earn a predictable income and to be creative! :) I appreciate so much inspiration from so many, along the way, but I do think that so many are saying, “do the work, follow your dreams, believe with all your heart, and the universe will take you there” … I’m afraid many people are setting themselves up for a really difficult road by believing this unconditionally. Dreaming, and following dreams is what makes life wonderful … but also be able to pay your bills … running out of money creates much hardship and blocks creative endeavors.
    xo Jane

  4. Thank you so much for pointing out how the current narrative of creative entrepreneurship (which seems to be entrenched even now in 2018) has now morphed into the ‘Disney princess’ idea. It can be frustrating to see so many happily sharing on Instagram but rarely speak the truth of the hard work and frustrations of self employment, but if you do that then you are bursting the bubble of the princess narrative! 🙄 And there is another entrenched narrative that has been going on for some time, one of ‘the creative who abandoned creativity during childhood, only to find it again in adulthood’, which is a popular narrative, but not one that I fit in with since I always pursued creative channels, and still pursue well into adulthood. I understand it is a ‘heros journey’ narrative that is appealing, rather than a narrative of someone who stayed true to their creative instincts throughout their life. Just joined your email list through your recent love letters and I’m loving this rich library of posts! Thank you again for this one, I needed it! 😊

    • Jamie says:

      I’m so glad you’re here, Monica, and thank you for pointing out the powerful narrative of “the one who stayed true”. I’d love to hear more about what that story means to you.

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