On Letting Go, and Being Let Go

Letting Go

In October 2017, I resigned from CoverMyMeds after around eleven years of service, which was an incredibly difficult decision to make.

I wasn't instrumental in getting the company to it's 1.3 billion dollar acquisition, but I contributed significantly to the company's success, and had been rewarded justly for it.

I spent a third of my life (from age 22 to 33) building products and internal tools, leading and/or managing teams (yes, there is a distinction and a difference there), stressing over deadlines and launches and hiring and team dynamics and composition and policy/procedure documents and HIPAA regulations and all the stuff that goes into a successful Healthcare Technology company.

Deciding to leave wasn't a thing that happened one morning, I didn't decide it over coffee. It was months of debate. It was heart-wrenching. I couldn't decide if I really wanted to. I was terrified of leaving, basically my entire adult life was spent working there, and nearly all my friends either worked there or had. In the end, I had to admit some things to myself:

  • Burnout had hit me hard some years ago. I read all the things and learned how folks cope, the time and space and therapy, then I said "pfft I'm awesome I got this" and went back in the very next day. That's what you're supposed to do, right?
  • I wanted to move into Serious Technology Leadership, since the company didn't have a CTO or VP of Engineering then and I thought I could work my way there. CoverMyMeds was very clear that they didn't want those roles filled at all by anyone, so I said "pfft I'm awesome I got this" and burned all of my political capital trying to convince them they did. They were unmoved.
  • After eleven years, I wasn't excited by the work there anymore. Not that they weren't doing cool things, or that there weren't teams I could move to. I just couldn't imagine being a part of any team in the company and being happy.
  • Oh yeah, I was unhappy. That crept in at some point. Probably because of that burnout, you think?
  • I could. I was lucky enough that financially, I could resign from the company and take some time to chill myself out and figure out what's next.

It was clearly time for me to move on. Maybe it had been for a while, and I was too stubborn to see it. But I struggled. It felt like I was giving up on this thing I'd help launch into the world. This was the first non-student job that I'd held for longer than a year, and it was woven into my concept of self pretty deeply. It also felt like I was giving up on me, that I'd tried my hardest to be what they needed me to be and came up short.

My last day felt awkward. I wanted badly to be done, but I also wanted badly to stay. To not pack up my decades worth of accumulated desk toys and office detritus. Folks were shaking my hand, hugging me, wishing me well, and that felt good. Plans were made to stay in touch, and I knew that it was likely I'd drift away from many of these folks. That felt bad.

The first full day at home felt freeing, like a weight I didn't know I was carrying had been lifted off of me. I dropped the kids off at school and came back home and sat down. I didn't know what I was going to do next, but I was elated to have the opportunity to figure it out in my own time.


Being Let Go

I won't be naming any names here. The names aren't secret, and as of publication you could probably figure them out if you had five minutes to spare, but that doesn't feel right to me.

Two months after I left CoverMyMeds, I started working for Beard's consultancy. He'd started it six months previously and had a few employees, but needed an extra hand on a project. I wasn't doing anything except worrying; it turns out I don't know how to be funemployed. I accepted.

Nearly a  year later, Local Startup bought Beard's consultancy. They needed to drastically expand their software development capabilities, and Beard was excited about transitioning to building a product. He'd said that they wanted to hire the entire crew, and he asked me what role I wanted to play on the new team. I told him I'd wanted to help run the software team and grow it and myself into the things I'd wanted at CoverMyMeds. He agreed. Discussions were had with Local Startup. They agreed. We worked out what my title and responsibilities would be.

Three days in, Founder and COO of Local Startup – both of whom I knew prior to this, and one of whom I have a side venture with – stepped into my office, closed the door, and sat in the two chairs opposite my desk.

"This isn't working out, we're not going to hire you," Founder told me.

He said things after that I can hardly recall. I was on complete autopilot after that. I'm relieved to say that my autopilot setting defaults to shake hands, wish well, depart silently and not rage hard, destroy property, shout at people. I remember putting things into my bag, first neatly and organized, and then panicky and rushed, forcing the laptop satchel into a sphere containing everything except a laptop. I threw my big overcoat on and walked the long way around to the door to avoid everyone, eyes ahead, mind fuzzy and trying my damnedest not to shed tears before I got to my car.

I hadn't even been given the opportunity to screw the job up. I was out.

Gone

When I left CoverMyMeds, it was sad and difficult, but it was my choice. I missed (and miss) those folks. I miss what it could have been for me. I still refer people to work there, and celebrate their accomplishments. They earned it. I earned it.

When I left Local Startup, it was sad and difficult in a completely different way. It was not my choice, and the folks I thought were going to stand behind me were literally behind me, growing distant as I drove away from the office for good.

I'd never been fired; or wait, I guess not hired after verbal agreement but after starting the job? Does that make it better?

Does knowing that you didn't do anything to deserve this make it better?

Are you sure you didn't do anything to deserve it?

I mean it was two and a half days, right? You'd know if you did something. It'd be obvious, and they'd have told you. "Here is the line, here's what you did that crossed it, here's why we've decided to renege after weeks of building you up for this position." Is that too much to expect?

At least your finances are in order, so you don't have to suffer the indignity of job hunting right before the holidays or last minute changing of plans. Does that make it better? Does the knowledge that it definitely makes it better but you still can't sleep right make it worse?

Who of the folks you used to call colleagues (or friends) can you still trust? How many called to check up on you afterwards, to express their shock and outrage and ensure you knew they cared? If that number is close to zero, does it validate your fear that you're some kind of asshole that brought this on yourself?

Do you think you can finish the whole bottle of scotch in one sitting? If you do, is there more?


It's been a week. Every morning, I wake up and try my best to shake off the bad feelings. I try my best to keep them from coming back during the day, and so far I have had limited success.

I've been writing this thing for days, editing, rewriting, changing the tense, the structure. I'm writing this for me, because I have to get it all out of my head or it will continue eating me. It is shameful and embarrassing to write these things down, but it's good for me.

I'm also writing this for you, if you've ever been fired or ever do, so you know that these feelings happen to people. I haven't recovered yet, but every day I get a little closer. Zach Holman's pieces FIRED, FIRING PEOPLE, and THE DEPRESSION THING helped me, and they are interesting reads besides. I read them when they were originally published and immediately had to go back to re-read them to remind me that someone else had gone through something like what I was going through, and it would be okay.

If you want to chat, I'm @joncanady and also jon@joncanady.com.

On Letting Go, and Being Let Go
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