What I Learned from Quitting my Job at 30

This past spring, I decided to quit my job as a teacher. In retrospect, that may have not been the best idea. I had big plans of taking over the day-to-day operations of my wife’s business while picking up projects doing marketing and copywriting for other small businesses. My wife and I already had a short list of potential clients, and we’d done so well getting her businesses off the ground. What could possibly go wrong?

Tomorrow morning, I will wake up between 5:30 and 6:00 AM. I’ll turn on the coffee, get dressed, eat a bowl of cereal, and leave the house. I’ll drive 45 minutes to school, park the car, and spend the ensuing eight hours teaching middle school students about parts of speech and expository writing. The only major difference between tomorrow and this time last year is that I’ll be doing it as a substitute teacher. I’m essentially a temporary employee; I now lack the stability and predictability of a regular paycheck and the benefits that come along with it.

I screwed up. I left a stable job to become a freelancer without putting in the time and effort it takes to be secure in that kind of work. I honestly thought it would be ok. I thought there was no way I could fail. “I’ve pulled myself out of darker spots and deeper holes,” I thought. “I’m an English teacher with a journalism background. I’ve been doing this kind of thing for a couple of years, albeit behind the scenes or for 12 year-olds. People will be tripping over themselves asking for my help.”

But it didn’t happen, and I didn’t understand why. I finished up the projects I’d booked and waited for the emails to come in. When they didn’t, I applied for jobs as a content writer or a marketing specialist or a “social media guru”. “I do this stuff every day,” I told myself. “This is right in my wheelhouse. With my background and experience, my applications pretty much write themselves.”

I assumed I’d have my pick of jobs by the time the end of the summer rolled around. I couldn’t wait to hand off my keys and my supplies to my replacement. “Oh, no, I had a great summer,” I’d planned to say. “I’m working a bunch of freelance gigs while I decide between moving to California for Facebook or working from home for GitHub.” I applied for those jobs. I interviewed at those companies. Everybody passed on me (with wishes of the best of luck), and I couldn’t figure out WHY.

Then it dawned on me.

Ok, that’s not entirely true. My wife figured it out in a way. While we were discussing what my plans are for after my long-term substitute teaching assignment ends, she asked me a very pointed question. “Not to be accusatory or inflammatory,” she said, “but what, if anything, did your parents ever teach you about humility?”

I thought about it. Like, really thought about it. My parents weren’t braggarts; I can’t think of anyone ever being jealous about what we had, or my mom and dad ever lording it over others’ heads. But I realized that no one had really ever talked to me about being gracious and not taking things for granted.


Growing up, I was small, but I was smart. From an early age, I thought I could outwit most people, and if I couldn’t, I’d still be able to talk myself out of any trouble. To be honest, that lasted for a good, long while. I was awarded the “Most Likely to Sell Oceanfront Property in Nevada” superlative as a senior in high school. In college, I went from lacking a capstone group project to walking across the stage as a graduate in three weeks. On my 21st birthday, when the grocery clerk wouldn’t sell me beer between the hours of 3 and 6 AM (when the great state of Tennessee says we can’t buy alcohol), I said aloud, “Don’t you know who I am? I’m Will Fanguy! I own this town!”

I was kind of a jackass. I wish I could say that it got better with time, but if it had, this was be a lackluster story. When you do something repeatedly and don’t suffer a negative outcome, that behavior is reinforced. When you miraculously get away with things you have no business pulling off time after time, you delude yourself into thinking that it’s not actually miraculous. You start to think you’re just. that. good.

Then you turn 30 and quit your job and your wife informs you that you and your ego can just go sleep on the couch until you both apologize for trying so hard to win an argument only you were actually having.

I’ve never thought of myself as egotistical. I’ve never considered myself someone who walks through life with a sense of entitlement, like everyone I interacted with owed me something just because of who I am and what I might be capable of doing. But I have been, and no one responds well to that. My wife put it best: “Only assholes like other assholes.”


So I’m saying this in hopes of turning it all into a learning experience. I hope that I can take what I see now and what I’ve done, reflect on it, and use it as a guide. I want to be an example of what not to be in the future.

This isn’t a lesson for others so much as it’s a reminder to myself. No one owes you a thing. Not your teachers, not your parents, not your friends. College admissions folks don’t owe you just because you have a high GPA and solid test scores. Potential employers don’t owe you because your dad knows a guy. Recruiters don’t owe you because you have a “decade of varied life experience.” Nobody owes you a damn thing.

So thank you, Facebook. Thank you, GitHub and Lyft and The Wirecutter. Thank you, HelpScout, Jumpcut Studios, Phuse, Ice Frog Productions, and ServerHub. Thank you for saying “no”. Thank you for passing on the guy that wasn’t the best fit, that didn’t have the experience, that had the audacity to assume that you’d jump at the chance to give me a chance.

I could excel at each and every job for which I applied, but I haven’t earned it yet. I’ve got to put in the work and the sweat and the effort, and I will. When the time comes, and I’ve worked hard enough, I’ll be back. Until then, I’ll keep my head down and work; I’ll be the hardest-working editor a client’s ever had; I’ll put enough words and websites together that they won’t be able to ignore my portfolio and experience.

But I won’t be an asshole about it. I won’t brag, and I won’t take it for granted. I’ll do my best to appreciate every hard-fought client and dollar that comes my way. If I don’t, I may be doomed to do it all over again, and I can’t. You only turn 30 and quit your job once.

Show your support

Clapping shows how much you appreciated Will Fanguy’s story.