Posts tagged Side Hustles
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,


Making acquaintances with imposter syndrome

I felt sick to my stomach last week. My editor assigned me a story in which I had to write about a subject that I tend to avoid like the plague.

What subject, you say?

Student loans. Specifically, mine.

These old friends. The presence that’s been in my life since I was 22. My longest-running intimate relationship to date, longer than any of my romantic partners and even better at keeping me awake in bed.

I was comfortable with them as long as I could talk about them privately to select people, in specific environments, and long after a trusting relationship has been established.

But talking about them openly in a major publication evoked a dread I didn’t know I had within me. I felt nauseous, I started trembling, I was annoyed. I looked for something to be mad at, then realized what was wrong.

Nothing. I only had to tell the truth.

I feel sympathetic for the Hollywood youngsters who had to grow up before America’s eyes, because now I feel like I am doing the same, reckoning with choices I made a long time ago with an audience of people who can judge, question, and critique in ways that are – let’s be honest – sometimes valid.

And here’s the thing – I realized the only way I am going to become comfortable talking about them, dealing with them, and moving through all this drama is by simply doing it.

So I sat down.

I wrote the article.

(It’s yet to be published.)

But now, of course I feel much better.

People think that writers have to be experts. And in many cases, we are. But in an equal number of cases, we write to make sense of the world. That’s how we got started in the first place.

It’s easy in a culture of idolatry, when brands, personalities, and celebs (not that I am one) are held in the highest regard to assume the false belief that in order to know anything a writers has to know EVERYTHING in order to have any value.

But that is simply, I’m learning, not true.

“I told you,” wrote Maggie Nelson in The Argonauts, “I wanted to live in a world in which the antidote to shame is not honor, but honesty.” 

Honesty. What an interesting idea.

Well, then. If we’re being honest, here is what I thought before I had the opportunity to write about something that made me profoundly uncomfortable:

I thought that before I’d ever write about personal finance, I’d have a lot more money in the bank.

I thought I needed to be perfect to be worth listening to, and that I had nothing credible to say because I had made mistakes in the past.

I thought that one day, after I’d privately arranged my life into perfect working order, invested more money in school, or a better website, or a branding coach, you name it – THEN I would deserve a spot behind the mic.

But then I realized – this resistance to taking a risk is exactly the kind of thinking that convinced me to put off earning extra income with a side hustle through college, and the same kind of thinking that told me to take out student loans with no plan because “one day” I’d have the answers straight.

And then I decided to, simply, give it a try.

The shaking stopped. The walls, to my knowledge, have not caved in. I’m still here, the same me only a few dollars richer than I was before the piece was written.

I got out of my way. I said the thing that was scary. And everything is better for it.

Shame is a powerful riptide. And the only antidote is honesty.