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Welcome to Part Three of my Pitch to the Top™ story, where I will tell you all about how I became a self-employed writer.

Today’s post is all about self-employment mistakes I made when I first tried to start my own business in 2014, and how I’m still learning from them today. Thankfully, I embrace a growth mindset, as opposed to a fixed mindset. I believe in our ability to adapt and learn from experiences for the better.

I’ve always embraced risk-taking, even when I was working for basically nothing and using student loans to earn my master’s degree. I wouldn’t necessarily recommend you follow every one of my footsteps, but I’ve learned a lot about self-employment through trial and error that I want to pass on to new writers.

Why mistakes are important

When I was a kindergarten teacher, I taught my students to give me a high-five any time they made a mistake. The first thing I said after they showed me their error was “Great! Now, what did you learn?”

Mistakes are nothing to be ashamed of, though shame is of course a normal part of the human experience. If we can get past the shame and learn to look soberly at our mistakes, they contain some valuable lessons. No matter how “successful” you get, this process of self reflection never ends. In fact, the mistakes sometimes get even messier once more and more of your livelihood is at stake. My business coach, Lisa Fabrega, calls this process “building your capacity.” It’s not like we wake up one day as fully self-actualized sages who’ve mastered every process in life. It’s a continual work in progress that just gets deeper and deeper.

My first attempt at self-employment

In 2014, while in graduate school and living with my then-boyfriend, I decided to start a business leading yoga and writing workshops. I wrote a little bit about this in my CNBC article, Stop saying personal finance is simple—it isn’t. My thinking was that I would use my student loans as a safety net, share resources with my romantic partner, and launch a fully thriving business in the three years I was in the program.

But being self-employed doesn’t stop life from throwing you surprises. Just a few months into my “master” plan, my boyfriend kind of, sort of cheated on me (it was complicated), and I was on my own for money without a steady job or enough clients.

Befriending and managing your inner child

At age 23, I should have been experienced enough to know this, but I had developed a brazen, take-no-bullshit inner persona that marched onwards no matter what risks were ahead. I used to think this persona was me, but I’ve since learned she’s actually the protective older sibling to all of my inner child’s wounds. This persona plows into all dangers, often biting off more than I can chew and saying “too bad, we’ll figure it out along the way!”

Of course, her traits are helpful, even necessary, at times, for any kind of entrepreneurship. This part of my story reminds me of the time I spoke with TIGER 21 founder, Michael Sonnenfeldt, who told me that some of the billionaires in his exclusive club for the ultra-wealthy are former misfits now motivated by the chips on their shoulders. The successful adults of today are often just kids who once had something to prove. I can relate to that, since my inner tough-girl child always has something to prove — and this fuel has brought me success!

So, rolling with the punches isn’t always bad. The problem was that this brazen, tough-girl persona isn’t a great planner, nor does she value herself enough to build in enough buffer and room for error. She only prepared for a best-case scenario in which I HAD to succeed…or else.

And when I didn’t succeed the first time — I learned what “or else” meant.

Self employment lesson #1: Save an emergency fund

After raising money through an Indiegogo campaign, maxing out my student loan disbursements, quitting my salary job (which only paid $27,000 at the time), I started leading yoga and writing workshops around town. I taught at my university and in a few local yoga studios. After months of learning marketing, planning curriculum, and also juggling the workload from my master’s degree, my boyfriend and I went through our messy, unpleasant, and disruptive break-up.

There was lots of drama (thanks tough-child persona). And off he went — along with my financial safety net. Because I hadn’t planned properly to be stuck on my own, I had to back-burner my self-employment dreams right then and there. I once again was back to the “pick me!” pattern of finding any old job to make ends meet.

What did I learn? A proper emergency fund (or what Paulette Perhach famously called the F*ck Off Fund) would have allowed me to continue on with my self-employment plan until money started coming in. But, I chose to put all my faith and trust in a man. It put too much pressure on our relationship, too much pressure on myself, and too much pressure on my baby business.

ABOVE: Me with my yoga props after raising enough money to buy them through Indiegogo.

Self-employment lesson #2: Nothing is actually lost

While I licked my wounds and decided it was time to look for a stable source of income (spoiler alert: I became a kindergarten teacher), the idea for a podcast came to me.

Which brings me to self-employment lesson #2: Nothing is ever really over. It’s all just a big learning continuum, and every project feeds into the next.

My yoga and writing workshops came to a pause, but a friend and I started a podcast that was very part-time and heaps of fun. We interviewed epic guests like accessible yoga teacher and co-creator of the Yoga for All teacher training, Dianne Bondy, and Jesal Parikh from the Yoga is Dead podcast. I didn’t know it at the time, but I was sharpening my interview skills for when I’d one day interview thought leaders such as Deepak Chopra and revolutionary money experts like Rachel Sanborn Lawrence, lead financial planner at Ellevest.

In a recent post circulating through social media, Bridget Thorenson writes, “I’m rejecting the career ladder metaphor in favor of the career river.” I like this imagery. What if careers aren’t a step-by-step, hierarchical progression, but instead a stream of experiences all flowing into one another, sometimes splitting off into tributaries, ultimately leading towards an ocean?

Self-employment lesson #3: Don’t overthink (or worry) too much

I have a neurodivergent brain. That means I overthink a LOT. I am also often riddled with anxiety (though I’m working on putting boundaries in place to calm my nervous system down, and it’s helping).

Before I started my business, I got a permit at the local city hall. I got insurance for the maximum penalty, because the mere thought of a potential lawsuit was enough to make me tip my wallet over and fold it inside out, handing over all of my money to any insurance company that would claim to protect me. I fretted over which email software to subscribe to, which membership platform to pick, which microphone to buy for the podcast, how I should format my spreadsheets (do I use brand colors?) — speaking of brand colors, do I have to hire a graphic designer before I do ANYTHING!?

How to manage overthinking

Here’s what I’ve learned about overthinking: It doesn’t work. Now, I give myself time limits on how much I’m allowed to think, zone out, worry, etc. And then, I change the subject in my mind and focus on just the things I can control. That’s why you see an imperfect website and blog headers that look like works in progress. Now, I put my energy where it matters, which is producing high-quality content for my clients, following-through on deliverables, and only partaking in marketing efforts that lead to an outcome.

Of course, there is some trial and error involved, and I’m certainly not doing everything perfectly. But I have learned to be much more to go with the flow. I still have my days, which is fine. Nobody can halt patterns overnight. But by practicing boundaries with my own tendency to overthink, I am working on becoming someone who overthinks less throughout the years. I expect this to pay off (it already has started to).

Self-employment delivers up an intense learning curve. It takes a few years to get a handle on all the moving parts of running a business, and nobody has it perfectly figured out. I make freelance business mistakes every day, but with experience I have learned to freak out about them less and prepare for them more.

The last big lesson that I’m always practicing is that you have to be willing to shed who you are every day in order to become the person you desire to be inside. I believe we all inherently know who we are, and life is the process of shedding, refining and growing until we re-discover it. Business is one way to practice this process, which can be profoundly spiritual and even transformative for some self-employed people.

Keep on keeping on, peeps! And check back in tomorrow for Part Four of this blog series, where I will finally dive into how I went from teaching kindergarten to being a CNBC reporter in under two years!

Don’t miss:

My Pitch to the Top™ story Part 1: The unpaid internship phase

My Pitch to the Top™ story Part 2: How I finally got paid to write


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