Spreadsheets, Google Docs, and Mailchimps – oh my!


It took me years to finally become profitable as a self-employed person. I started with a zillion spreadsheets but had nothing to show for it, even after exerting TONS of effort. This time around, I have I realized the most important tool is not about project management, budgeting, or email automation. It’s not about spreadsheets, Google Docs, or Mailchimps –

It is about mindset.

Let me back up. In 2015, I tried my hand at self-employment for the first time. Well, make that the first few times.

I started a yoga and writing workshop business that helped dozens of folks explore their voices and their bodies…and made about $1500 in 9 months. I wrote a children’s book that brought in $27 of royalties after 3 years of work (but gave me good reason to keep in touch with my dear friend and illustrator). Finally, I started a podcast with ANOTHER friend that was fun, but not-so-lucrative.

With my tail between my legs, I told myself the jig was up. Time to find a reliable job. Which was for the best, truly. I gained some financial stability, learned how to negotiate a good salary for myself, and worked as a teacher at two great independent schools. I spent time with some inspirational young people and met some great families. Teaching fed a particular part of my soul, and I thought that writing in the summer time would be enough for me. Sounds reasonable, right?

Wrong. I loved teaching, and I was even a fairly effective teacher! But the deal I had struck with myself sacrificed the integrity of what I actually wanted. I was not making enough money to do much more than teach. And the schedule messed with me – utmost regimen from August-June, then total freedom in the summer. It left few opportunities to travel for writing retreats, and when the summers came and I had no structure to my day I felt, mostly, confused.

And I was pouring all of my creative juice into the children I had grown to care for.

So what did I do? I boldly declared that I, the writer, would WRITE! I crafted a plan to exit teaching and found my way into freelance writing IMMEDIATELY!


Wrong again.

I decided I needed a SECOND master’s degree.

I traveled to Ireland for a low-residency program, took out $10k in student loans, and when I got there my mentor asked me what I was doing in such a program.

Not because I wasn’t welcome. Not because I wasn’t benefitting.

But, she said, I had so much life experience. More than the average student. What was I doing in a classroom? Get home and WRITE she said.

But I had no confidence! I wanted to do the thing I was good at doing so badly, but how?

One year later, I am celebrating the first month that I will replace my day job income from – you guessed it – writing. I enacted a new series of habits and routines that I discovered through some very affordable online courses on how to earn a living by freelance writing. I found the affordable systems of support and began to LEARN BY DOING, not by expecting perfection. And the best part – I didn’t even need more student loans!

That’s the spirit in which this blog was founded. I’m still processing my journey from broke to brazen - how I went from a broke idealist to a self-employed solutions journalist & freelance writer.

I let go of perfectionism, and just…simply…started.

And here I am, still going.

To imperfection,