I. Introduction

I Get it, But You Don't Have to Teach

When I graduated with a MALS degree with a concentration in creative writing in 2008, I considered a PhD to pursue a professorship. However, academia looked big and scary and the career track seemed long and arduous, filled with adjuncting, low wages and job insecurity before perhaps obtaining a tenured position in North Dakota through years of politicking (read: academic butt-kissing). I also continued attempting to write, though I never really sorted through that option, and after a couple of rejections in the dying publishing market, my confidence sagged into the mire. I had also flirted with the idea of a business degree, though ultimately made the choice to stick with the arts, labeling a MBA as a form of signing the black book. My ‘Renaissance Man’ act, in other words, was shattering up against the hard malice of the no-nonsense professional world. I had a lot of ambitions, but no real direction, unable to settle on any of them in particular.

I had been tutoring two classes of Dartmouth freshman in the writing program for several years, once a week on their essays, and it certainly felt good. To be able to genuinely assist another young human being in their quest to establish themselves as a legitimate thinker? Well, there was no better gift. I didn’t know what I wanted to do with myself, but I knew I could do that and it was a steady income and a job that didn’t involve Microsoft Excel. With only a vague notion of how the professional world worked and little self-confidence to speak of, I applied for teaching jobs as the graduate work wrapped up. A few months later, I found myself in a teaching career, with four courses, two seasons of coaching, advisory responsibility, committee participation, and dorm duty several times a week to keep me up nights. Though I never had, I started drinking coffee every day.

Well, as HD Thoreau once said “Being a teacher is like being in jail; once it’s on your record you can never get rid of it.” I didn’t understand what that meant the first time I read it as a young teacher, barely older than the students I was assigned to, but every year I understood it a bit more. When I arrived at Taft in the fall of 2015, I had been securely reduced to the “golden handcuffs” of boarding school life. There was a lot of BS, I mean a lot. But they provided free housing for my entire family, a dining hall situated a hundred yards away from where we stayed, summers off, and job security no matter what happened in the outside world. In other words, they made it very difficult to quit. 

And yet, as basically any teacher can attest to, the lifestyle was as arduous and trying as it gets. I was teaching four classes(including on Saturday!), coaching two seasons of sports (with away games that kept me out all day and night), managing four separate committees, and dorm-parenting a hallway of 50 or so 17 and 18-year-old boys. Combined with the prep work and the grading and the mountains of ridiculous administrative paperwork, I was logging about 80 hours a week and making what amounted to minimum wage, including the benefits. 

And perhaps more importantly, while I felt the fulfillment of helping young people, I was more ambitious about my life, and felt the need to be doing something a bit more cutting edge. Teaching felt like a surrender to life. A very comfortable surrender. 

And in addition to that, while I sometimes justified the sacrifice as one to help my kids, I barely knew them. My wife spent all her time with them, and I was almost never there. When I got home, most of the time they had already gone to sleep. I drove them to school sometimes I guess, but without much common experience, there wasn't much to talk about. They were growing up before my eyes as strangers, nervous to even embrace their own father, estranged from their lives.

So I torched it. 

I quit my job with Taft halfway through August and essentially told them to take their golden handcuffs and paddle up a creek. There was certainly some drama surrounding the decision. I had gotten a poor review the spring previous, as far as I can tell because I wouldn’t stay up past 2AM on a Saturday and attend all the pep rallies with my face painted red. The discussion of actual teaching amounted to about two sentences. In my THREE DAYS of paternity leave, the substitute had flaked out on me for no good reason, and I was blamed for not checking on it. The final straw was the administration hassling me about the vaccination record for my children who were admittedly a few behind, mainly because we couldn't arrange for trips to the doctor during the busy school year. But they threatened to kick us out of our apartment if we didn’t get it done immediately, and that was about it for me. I had better things to do with my life than the haggling civil-strife politics of boarding school. 

The above had pissed me off pretty good, but in the end it was an enormous blessing, so thank you, Taft. Thank you, deeply. For I now run a burgeoning tutoring corporation of roughly 30 subcontract tutors and 80 active clients and thrive on the passive income earned. I barely knew my first two kids in their toddler-hoods, rushing between senior seminars and freshman soccer games in bum-you-know-what, Connecticut. Now I spend every day, every afternoon, with my four-year-old. We go to the playground and eat frozen yogurt with gummy bears on top. I work two-three hours a day in the morning and make enough to support a family of five living a wealthy lifestyle in an affluent Connecticut suburb, and we barely ever think about money. We have everything we could need and answer to no one, no boss of our lives.

I don’t say this to brag; it’s actually difficult for me to write this, given my inherent modesty that anyone who interacts with me will know. I say it because it’s possible FOR YOU! You don’t have to teach or adjunct or struggle with substituting or academia. There’s no damn reason in the world you can’t do the exact same thing I did and liberate yourself from the BS of bureaucratic education. You don’t have to teach (!!) And you needn’t lose any of the rewards of doing so, either. I tutored a kid who was failing out of college and took to googling “how to drop out of college” when I met him. He just graduated this spring with a double major in Econ and History Magna Cum Laude and attending business school. Again, not tooting my own horn but suggesting that all of the rewards of teaching can be yours, investing a fraction of the time and making multiple times the wages available in traditional education.

All that’s needed is what feels like reckless courage and faith. I was lucky enough to get kicked out of the nest by life. When you find yourself at the next crisis point in your life (we all do), see it as an opportunity and seize it. Here are the simple steps to leveraging your experience and background in education into a career as an educational entrepreneur. There is zero reason why you can’t do the same thing I did. It’s not complicated at all. Dump the tediousness of what you’re doing and follow these steps to starting your own venture– one where you are the boss of a vision that’s all your own.

Complete and Continue