My early entrepreneurship journey

Like this Australian police dog, we each have a job to do. Unlike this Australian police dog, we can promote ourselves. (State Library of New South Wales)

In the journey of entrepreneurship, there are a few leaps to make.

One is to go from working for someone else to working for yourself.

Another is to go from being paid directly for the work that you do — often, by the hour — to being paid out of the proceeds of the business.

Then, you can make the leap to start something new.

These leaps are not necessary for everyone to make, nor do they always run in a linear progression. But here is the story of how I did it.

The first leap wasn’t that hard for me because I had very little to lose. Having trained as a music educator, my first “real” job was as an elementary school music teacher at two schools in Kittery, Maine, serving about 500 students in grades. The job paid $22,500, plus benefits. The year after I left, this base salary was raised to $28,500, and I think it’s still something close to that today.

It was tough to survive on that. I made more money waiting tables. I did start to attract some private music students, though, and that got me thinking. At $50 an hour, it would take less than 10 hours a week to equal my salary as a full-time teacher.

Thus, I left my teaching job after just one year and struck out on my own. I complicated matters by moving to a new city, but I still came out ahead — hadn’t even been able to afford an apartment in my previous town.

Things weren’t exactly smooth financially in my new situation, though. While it didn’t take me long to equal my previous salary as a freelance music teacher, that salary hadn’t been enough in the first place.

Plus, I was now running my own business. I no longer received paid vacations. I had to do my own marketing and set my own policies. New in town, I started working as a contractor at a local music school at $32 an hour and at a local preschool for $25 an hour. I was a lot less trapped than I had been in my salaried role, but I was still kind of trapped.

I was young, so I was fine with this setup at the time. I put my energy into writing songs and performing. But as I attracted more students than I could serve, I started to focus more on my teaching. I brought additional music teachers into the neighborhood, provided them with students and a place to teach, and now I had a music school of my own.

This was the first major step in leveraging what I had built so far, but I didn’t execute it particularly well. I figured that I would be paid a commission on each lesson. However, given our pricing and volume at the time, there really wasn’t much left over after paying for all of the additional expenses.

Worse, there wasn’t enough for me to pay someone else to do the administrative work, so I was essentially going from a $50/hour job to a $15/hour one. Or really, a $0/hour one — the first few years, the music school barely broke even and I made only enough to pay myself for the lessons I was teaching (which was just as many as ever).

Over the next few years, I worked hard and learned a lot. I was able to hand over some administrative tasks and cut back a little on teaching. I wasn’t making more money, but I had a little more time. I used this to start another school.

This new school at the same problem as the music school: I was basically just adding a job for myself. However, financially, I needed another job for myself. Adding this new role in this new business, I was finally able to get my income past the $36,000/year threshold where I had been stuck for my entire career as a music teacher.

With these two schools to play with, I configured and reconfigured pricing, expenses, staffing, and my role in order to find a way to have a steady income without having to work twelve hours a day. Some years, it worked better than others, but I started to get the hang of it.

Most importantly, I began to see myself differently. I realized that I didn’t have to be an employee of my business, and I was most effective (and happy) when I wasn’t. My income didn’t have to be directly tied to the work that I did.

Before long, I began attracting opportunities that I never would have been able to enjoy if I were still running my schools alone (or working day in and day out as a music teacher). I did some curriculum development work for Khan Academy. I was able to attend conferences to learn new things. I began coaching for the Akimbo Workshops. And I experimented with some new hobbies and business ideas.

These days, I am wary of any business venture that requires me to show up hour after hour. I’m not afraid of commitment — the challenge is that I already have a number of commitments. I can’t go back to working in a business. I need to be free to support my employees and deal with crises that come up. There has to be an exit plan in anything I start. I have to see the end in the beginning.

That said, I love to explore ideas — mine and other people’s. I love to share what I’ve learned. I love to connect with my fellow business owners and offer them support so that they can reach their goals faster than I did.

Sometimes, I get paid for this work and sometimes I don’t. I don’t worry about that too much. That’s not because I’m incredibly wealthy — it’s because I have a bit of time freedom because I don’t have a job. Now you know how I got there. I’m happy to help you do the same.