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Quitting My Job Was One of the Hardest Things I’ve Ever Done

And I learned a lot about myself

By Casey JunePublished 3 months ago 6 min read
Quitting My Job Was One of the Hardest Things I’ve Ever Done
Photo by Jem Sahagun on Unsplash

My heart is pounding and I’ve been sick to my stomach for a week. I have waited three days for my boss, the company President, to come into the office, but he had other places to be. I’m out of time. So I breathe deeply once again, for probably the 500th time that hour, and with shaking hands I call him on my cell phone on the way home from work. I’m virtually in a panic because I’ve placed The Call. I can’t go back now.


I was always exhausted. I worked the 6:00am to 2:00pm shift five days a week, which is on the early side for most people, but nothing extreme. Unfortunately, my commute was 55 miles in each direction. In Northern Virginia. Which, if you’re unfamiliar, is just outside of Washington DC and more often than not a complete mess of traffic.

To add to this, there was the overtime. There was always overtime. “It’s not required overtime, don’t feel obligated to do anything more than you’re comfortable with,” they told you. And then asked for monthly reports on contract hours worked and how we were going to make up the deficit.

This means I often woke up at 3:30am, showered, got my lunch and coffee ready, spent an hour in the car, and started work around 5:00am.

I thought about changing jobs for years, literal years, but always found reasons not to. The commute was awful, yes, and the extra hours I had to work seemed to devour my soul, yes, but otherwise…

This was almost a perfect job. My company paid me well. Gave great raises and solid bonuses. The job was rarely stressful. I worked with my best friend, whom I consider a brother (and still speak with daily). Our customer was great. My company management was great. I felt I had a real friendship with the company President and the VP.

But I couldn’t do it anymore. I was so tired all the time that I was probably a miserable husband and terribly boring father. Lack of sleep left me feeling sick half the time and fought migraines constantly. I had to keep on top of my water intake and strictly schedule my coffee breaks else my head would be in so much pain I would begin throwing up if I didn’t have enough pain killers on me. My memory was short-circuiting and I struggled to keep my mind on top of the things I needed to do.

I had done this commute and schedule for 15 years. My health was unable to keep up with this continuous sleep deficit as I aged, and I felt like I was failing my son who seemed to be growing faster every year.

I waited until we’d won the new contract. I waited until we had a full team of qualified people. I waited until everything was set up for success. I believe I was subconsciously waiting until another excuse to stay showed up.

But then I found out my wife was pregnant again, and I finally found my motivation and courage.

So after two years of thinking about leaving the office for a remote job, I did it. I applied for at least a dozen jobs before I even got a call. I did video interviews, I asked a million questions. I made sure the interviewers were aware not only of my strengths, but of my weaknesses. I told myself I was making sure I wouldn’t get into a job I couldn’t do, but if I’m being completely honest… I was probably trying to sabotage myself. Not getting hired felt a lot safer than leaving my comfort zone. My shameful little safety net.

But against their better judgement, someone finally hired me for a remote position. A DevOps role. I was ecstatic and also freaking out. Getting a remote job was my dream come true — but unfortunately it also meant quitting. And starting starting completely foreign to me.

I felt like I was betraying my friends. Abandoning my team. I thought it would feel okay because I waited until just the right moment… but instead it felt like I’d been hiding from them. Everyday we shared everything in our lives with each other, and for months I was silent about what I was doing outside of work.

I didn’t think it was going to be easy. It was, in fact, far worse.

That initial phone call was much easier than I anticipated. My usually verbose boss was so shocked he barely had a word to say. I pressed the red circle and felt light. Free! I had done it!

But then I had to go back to work the next day.

I cried. My friends cried — especially that one friend (I’m so sorry!). My boss regained his ability to speak and came into work early to scream at me at 6:15 in the morning (“You only gave me two f*****g weeks!”), and then later also cried. Twice. I probably cried again a couple more times somewhere in there.

But I received hand-written letters and coins and thoughtful gifts and I felt so unworthy of all the beautiful, kind words and generosity. I’ll treasure these memories and items forever, and hopefully one day they supplant the more hurtful parts of this story in my mind.

I think my friendship is over with my old boss. And him being the company president I don’t know if I’ll ever be welcomed back if I were to try and return.

My friendship with my coworkers stayed strong throughout and we now chat daily over IM. It’s not the same, but it’ll have to do for now.

I’ve left jobs before (this was my fourth in my IT career, my 9th in my lifetime) but this was a wholly new experience. A far more painful one than I even expected it to be when I dialed my boss shaking from anxiety.

I learned a lot about myself, though. What I care about, my anxieties, my strengths, where I need to push myself to improve.

And in the end, I started my remote job and it’s perfect. I’m learning a ton (sorry, teammates). I’m home for my growing family. I’m as well rested as one can be with a newborn in the house. I no longer have that deep-rooted gut-clenching dread of my alarm clock every night when I look at the time before bed.

Life deals out some amazing moments and plenty of heartbreak, but you’ll miss all the best stuff if you don’t push through the discomfort. Sitting still, staying comfortable has never helped anyone improve their circumstances or themselves. The more you do the difficult thing the stronger you become, mentally and emotionally. And the easier doing those difficult things will be.


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