Becoming My Own Boss

For about a year now, I’ve been mulling the idea of starting a business. Earlier this week I decided to announce my intention publically, ready or not. So, here we go: Over the course of the coming year, I plan to track my progress (here’s hoping) through a new series I’ll call Becoming My Own Boss.


If nothing else, I hope my explorations can give you some dose of courage. Have you, too, decided to put your foot on a new path? Who knows, maybe something I encounter on mine will help you navigate yours. First up: I need to get clear on exactly why I’m doing this.


Entrepreneurs tend to be shiny-object types who have lots of new ideas, and I am no exception. But at 42, I’ve come to know that time and energy aren’t infinite. I’ve learned the hard way that self-care isn’t a luxury, and I’m committed to protecting it with a fierceness I never knew in my 20s or 30s. So before I rush ahead, I’m making sure I understand my motivations so I can stick to them as I go.


Evidently midlifers often change careers to find purpose. Flush with cash but empty with meaning, they seek a deeper call. For me, though, a primary motivation is precisely the opposite. For 15 years I’ve worked at a nonprofit whose mission is dear to my heart. My roles there allow me to contribute to an undertaking I still say is the single-most important in society: education.

But a funny thing’s happened over the past year or so, as my inner entrepreneur has emerged. Its voice started quietly but has grown steadily louder. These days, it’s nothing short of a scream. For the first time in my life I’ve started to realize, “Hey, wait a minute, I want to make more money.” Not enough to earn a spot on Richard Branson’s Spaceline or anything, but enough to build a freaking savings account.

What’s more: I’ve gained skills that are worthy of being paid accordingly. I wonder if you have any idea, though, how hard it is for me to say these things. For the better part of a year, my inner dialogue has gone something like this: “Huh, I wonder if there’s a way to add to my savings rather than drawing it down?” Then: “Whoa, hold on a minute there, Missy! Who do you think you are? Educators don’t make money. Niether do artists or creative types like you.”

Even as I type this, I feel a strong sense of guilt. I’ve never had to worry about where my next meal’s coming from, and hunger is a crushing problem in my city, for starters. (Just ask Second Harvest Heartland.) I know I’m privileged in a myriad of ways. Still, as I’ve contemplated starting a side gig, I’ve had to face some deeply ingrained assumptions around finances, earnings, and worth.


One resource I’ve found helpful is Kimberly Palmer’s Economy of You. Through stories and an approachable tone, she underscores the importance of “recession-proofing your life.” I found the book so useful I took notes and found the experience empowering. I didn’t formally use her exercises and worksheets, but I’m thinking now they’re worth a second look.


Palmer’s book also resonates with another of my entrepeneurial whys: I’m inspired by women business owners and I want to join their ranks. There are many reasons for this, but here’s a main one: I’m tired of asking permission. In recent years I’ve observed the amount of energy I’ve wasted, waiting for it to be bestowed: Permission to speak, permission to lead, permission to be noticed.

Yes, we still live a society where women are rewarded for compliance and constantly feel the need to apologize. (Oh, how I adore Amy Schumer’s skit skewering this phenomenon.) I recently came to the understanding that I’ve been waiting, for years, for somebody to give me a shot. I’ve yearned to be given the chance to put my skills together and make an impact. At some point in the last year, though, I had a new realization: Daaaaang, what if the person I’ve been waiting for all this time is me?


Why not me, indeed? After all, nobody is better equipped to know my skill set. Barriers to the marketplace are growing ever thinner. And thanks to podcasts, youtube, online communities, networks of fellow doers, and good old-fashioned books, I have access to a multitude of tools. (My warm appreciaton goes to commenter Peggy for sending me “Artist’s Statment Part Two” from The Pale Rook, which absolutely struck a chord.)

And so, after months of pondering and research, I’ve narrowed my ideas to two possible business ventures. Though I love both, I must force myself to choose. I still work a full-time job, after all, and I need to be realistic about the fact that anything I start will be a side gig.

This is where Quest2016 comes in. Yesterday’s prompt came from the ever-inspiring Jonathan Fields, who runs the camp for makers and world shakers I attended this summer. By the way, it’s responsible for much of my recent entrepreneurial audacity. Here’s his prompt:

You wake up to discover a knock at your door. A wealthy uncle you barely knew has passed and left you a fortune. It’s more than enough to live out your days in glorious splendor, but there is a condition. To be eligible to collect, you must commit your full-time working energies to the pursuit of an answer to a single question of your choosing for the next 12 months.

You are welcome to continue that pursuit after the year ends, for years or decades if it warrants, but you must remain fully focused on seeking the answer until the last minute of the 365th day. A minute shorter, the entire inheritance goes to your annoying and equally long lost cousin, Philly.

What is your question?

For me, defining the question was relatively easy, as I’m already on the path to exploring it. Seeking the answer, though . . . now that’ll be the trick! Here’s the question I’m contemplating:

How can I start and maintain a side business that hits the sweet spot among these criteria: 1) heart and meaning, 2) gifts and flow, 3) skills and tools, and 4) value and profitability? I came across these pieces in Lisa Sonora’s The Creative Entrepreneur, which gives its own prompt for journaling about this, in the form of a creative mandala.

creative_entrepreneur_mandalaI posted about this book the other day and was surprised to receive not one, but two messages from women who know the author. The fact that an ACTUAL PERSON wrote the book came as an odd suprise to me. Sure, it’s filled with personality and heart, but–hey–my only encounter with the book had come through a random search on Amazon.

Independently, both women informed me Lisa Sonora would be pleased to know her work is impacting me. Now I feel doubly encouraged that I’m on the right path of owning my dreams and putting them out into the world. That said . . . I’m curious see what comes next.