I did it. I quit.
I had never resigned from a job before. I’ve had a handful of employers over the past decade, but every job I’ve ever held seemed to come with a predetermined end date – a summer-long gig, a four-month internship, or a multi-year consulting contract. For the past five years, though, I’ve worked for one company. For the first time in my life, I needed to sit down with a boss and break the bad news.
I’m not good at breakups.
Walking away from this job was different, too. Five years ago, the company didn’t even exist. As the first full-time employee, I spent a year working on whiteboards in garages. For months, I slept on a friend’s floor when we traveled to meet our first prospective client. I went a year without a paycheck. That dynamic changed quickly, though. Investors took majority control of the company, brought in new leadership, and relocated our corporate headquarters 2,500 miles away. It’s not the little startup it once was. But in some ways, it still feels like my baby. All that history has certainly made it difficult for me to walk away.
I spent most of the day this past Wednesday writhing with anxiety. Over and over again, I rehearsed how I would break the news. I would have preferred to do it in person, but it had to be by phone. I envisioned all the disgruntled reactions I might get from our CEO – disappointment, anger, frustration. I pictured our General Counsel being called in to have me sign non-disclosure and non-disparagement agreements. I envisioned my e-mail being immediately cut off and a request for my laptop and phone to be sent back by end-of-day. I imagined awkward phone calls with colleagues and clients as I was forced out.
And then, everything went just fine.
In fact, it was literally the best conversation I’ve ever had with our CEO. Though he expressed his deep disappointment, he shared that he was excited for my travels (and a bit envious). He opened up about his life, sharing his own experiences traveling and living abroad. I learned more about his personal life in 20 minutes than I had in all the time I spent working with him. He complimented my working style and my work ethic. He heaped on more praise and positive feedback in 20 minutes than I had ever received from him. “Wow, maybe I should have threatened to leave a long time ago,” I thought.
Just before the conversation, I had been reading about the Mad Fientist’s experiences with quitting. Three times, he’s resigned from a job and been offered far superior working arrangements: higher pay, more flexible hours, or location-independent work.
He was right. Quitting didn’t restrict my career options, it expanded them:
- “Is there anything we could do or change about your role to persuade you to stay?” (Not really, but I appreciate the offer)
- “Would you be willing to do some contract work for an hourly rate while you travel?” (I’m certainly open to talking about it)
- “If you ever decided you wanted to come back to the company, we’d be more than happy to find a place for you” (Thank you; it’s always nice to have a safety net)
There’s an old saying that goes, “I have known a great many troubles in my life, but most of them never happened.” Looking back, I don’t know why I was so stressed out about the encounter in the first place.
We talked about timing and transition planning for a while, and then I hung up the phone.
It was over. I did it.
I had fantasized about this exact moment for years, but I didn’t feel ecstatic or even particularly happy. Just relieved. I felt free in a way I haven’t felt for a long, long time. Like a massive weight had been lifted off me. Like I was floating.
Every ordinary experience over the past few days has felt extraordinary: the warmth of flannel bedsheets, the first sip of morning coffee, the sound of my favorite album playing on the living room speakers. I remember feeling this way once before: my senior year of college, after handing in my very last paper. It was short-lived then, and I suppose it will probably be short-lived now.
But there is one notable difference:
I never have to work a real job again.
Years of living frugally and banking 60-80% of my income have paid off with the ultimate freedom. I have no idea exactly what the future holds or if it might include full-time work. But if it does, it will be 100% my choice, on my terms – because I want to be doing it, not because I need the income.
Meanwhile, Daniel also put in his notice last week, in much less anxious fashion. We’re wrapping things up a month or two earlier than originally planned, which will give us time to sell some of our things and prepare for full-time travel. Or, maybe we’ll try to take advantage of ski season and do some road-tripping in February and March. We’ll figure it out.