A year and a week ago today, I sat across the desk of the man who had once been my manager, waiting for the man who currently was to arrive.

I tried to act casual as we made small talk, even though my heart felt like a hamster wheel about to fly off its axle. Could he tell, I wondered? Was I sweating or fidgeting a lot? Was I giving away my reason for being here?

In moments like this, I tend to double down on intentional body language. So I leaned back in the chair and crossed my leg, all the while keeping the two envelopes in my hand concealed from him.

“How’s everything at home?” he asked.

“Fine,” I said.

“And you?”


We both nodded.

He asked if I was copied on some ridiculous email thread or another. There were a lot of those at the time. Although budgets and staffing levels had been shrinking steadily for the past few years, the expectations of The Board were at an all time high. Which resulted in a fair amount of interdepartmental strife that played itself out either in too many too-long meetings or endless email threads.

I told him I was, and we spent the next few minutes commiserating about it. This is how our conversations always went whenever I made the long 2-hour commute into the office in Manhattan. Which wasn’t often. Rarely did we talk about the kids or what our vacation plans were. Mostly it was about how broken we thought the company was, and how little progress was being made on pretty much every front.

Then, during a pause in the conversation, he hit me with the question I’d hoped he wouldn’t ask. “So what is this meeting about anyway?”

Since I was the one who’d scheduled the meeting, I should have had a quick answer ready for this. In fact, it was unlike me not to. As an introvert, one of my key coping mechanisms is to plan for every possible contingency. Yet for whatever reason, it never occurred to me to script a response for that simple question.

The truth was, I hadn’t counted on one of them being so late, and had figured I could simply float into the room, hand them each an envelope, ask if they had any questions, then float back out again. Maybe even catch an early train back to Connecticut and finish out the rest of my work day there.

As it turned out, I paused a second too long. My ex-manager narrowed his eyes and grimaced at me. Not quite a smile and not quite an expression of pain, but a little of both. “Are you giving notice, he asked?”

“Yes,” I nodded, barely able to hear my own voice as blood pulsed behind my ears. And yet, as the word left me, the relief was as palpable as if I’d flipped open the lid of a screaming tea kettle. I had been holding onto the secret of what I planned to do that morning for the better part of a week, only telling my girlfriend and one trusted coworker. Now it was out. And I could breathe again.

He simply shrugged, as if to say, “I’m not surprised.”

I handed him one of the envelopes, inside of which was my resignation letter.

“For what it’s worth, I don’t blame you,” he said, as he opened the unsealed envelope and unfolded the letter. I knew he wouldn’t. But it was nice to hear him say the words anyway. “This place …” he started, as if considering which direction to go with the sentence, then simply lost his way.

He read to himself the letter I had spent the last two days crafting. I had been very careful with my words, putting the I (intellect) over the E (emotion). Since I knew it would be part of my “permanent record” with the company, I wanted it to document in at least some small yet professional way the frustration that had led to it, and the fact that things were ending like this.

The closest I got to this sentiment was the second paragraph:

“For the most part, I have enjoyed my time working [here] these past 5+ years, and value many of the relationships I have made. I only regret that the company’s expectations of me and my expectations of the company have diverged considerably in that time, and so it is for this reason that I feel compelled to move on to new challenges.”

The rest of the letter was me assuring them that I would do everything I could over the next two weeks to facilitate my transition, including whatever documentation or training was needed, and wishing them the best of luck in achieving their goals going forward.

Just as my ex-manager was putting the letter down on his desk, my current manager walked through the door. Almost ten minutes late. He offered no apology. “What’s going on?” he asked, no doubt sensing there was something off about the tone of the room. Too quiet, maybe.

I handed him the second envelope as he closed the door behind himself.

To be honest, the next fifteen minutes or so is kind of a blur for me, in large part because my adrenaline was running high at this point. Without getting into the details, because that’s not what this article is all about, suffice it to say that I didn’t have a great relationship with my current manager.

I do remember him asking me where I was moving on to. As in, who was I going to work for now. And when I told him nowhere, he seemed genuinely shocked. When I clarified that I planned to return to freelance work, they both nodded, but didn’t seem to know what to do with the information.

What they didn’t–and couldn’t possibly–realize was that when I made the decision a week earlier to give my notice after a year of being terribly unhappy, I knew it meant I was not only leaving the company. I was putting behind me once and for all the idea of working as a salaried employee for any company.

“Are you sure?” the current manager asked. “What about your family?” And then he offered me some kind of “extension,” which I politely declined. In my head, of course, I phrased it as, “I would prefer not to.” (For those who don’t understand this joke, please go read Herman Melville’s classic short story “Bartleby the Scrivener” right away.) But I’m sure I just said something like, “No thanks.”

Yet when one of them, I don’t remember which, asked if I would be willing to do some contract work for them until the new sites were launched, I said, in as cool and detached a manner as I could, “Sure. We can work something out.”

Honestly, this was exactly the offer I’d been hoping for. In fact, if one of them hadn’t brought it up, I was going to myself. But it felt better having them do it. And that’s how I ended up in the somewhat enviable position of continuing to do steady work for them for several months after I struck out on my own.

This of course turned out to be both a blessing and a curse for me. It kept me stuck in the technical world of web development, which wasn’t really where I wanted to be anymore, for much longer than I might have been otherwise.

But things often happen as they do for a reason. If I hadn’t experienced the severe drought of work that kicked in after that, I would never have made the time to write articles and engage more and make connections and friends on LinkedIn.

And if I hadn’t done that, then odds are I would never have achieved the clarity needed to make the decision at the top of this year to focus primarily on writing and messaging. Which has not only brought me far more happiness but has also brought with it more success.

A year and a week ago today, as I sat on the long train ride into Manhattan, trying to imagine how the day would go, I was terrified. Why was I even thinking about leaving a salaried job with benefits? Why wasn’t I just going out and looking for a new job like a normal person? Was I crazy?

Thankfully, my partner in life, my girlfriend of almost ten years, told me I’d be crazy not to do it. She could see how unhappy I was. How unhealthy I was. She believed without reservation that I could be a success on my own, and helped convince me that I should believe it too. And I’m grateful that she did.

Because a year and a week later, as I sit writing this even though I’ve got a ton of client work to do, I think, “What a wonderful problem to have.” Don’t get me wrong. I’ve still got a long way to go yet. I’m barely “net positive” and have no clear growth strategy and should be charging way more for my services and some days it feels as if I’m flying completely by the seat of my pants.

But again … what wonderful problems to have.

To be fair, I can’t in good conscience advise anybody else to do things the way I did them. Technically, I acted in a fiscally irresponsible manner by leaving a job without a replacement source of income lined up. So sue me.

I did what I had to do for me. I let go of the trapeze bar without a safety net, and figured I would teach myself how to fly on the way to the ground.

And for better or worse, I still haven’t hit it yet.