What Happens When You Finally Quit Your Job?
It’s usually different than you imagined
Today is the day, you’ve had enough. Enough of the overwork, undervaluing, borderline abuse, and lack of caring. You’ve put in your time, you’ve tried more than you should have. Today’s the day you quit.
Back in June of 2021, this was me. I had been working for a tech company for 5+ years. We developed software for OTT (Over The Top) and I was their Head of Product. I wore so many hats that I didn’t even know what to tell people on calls, so Head of Product never really rolled off the tongue. I felt all the things mentioned above, while feeling lost and overly burnt out. Like most workers these days I had a side hustle, well, more like a few. I had ideas and plans, but couldn’t truly capitalize on any of them due to the lack of energy. Earlier that year I was awarded a grant from Adobe to create a documentary series that I pitched them, but didn’t have the time to really focus on it. So, after much thought, I quit.
See, I quit due to a lot of reasons that happened to line up for me. Working as a Head of Product I made a solid salary. I was underpaid for sure, but still more than I ever made in my life. While making this salary I had the opportunity to pay off all of my debt, minus my car and school loans, and save a solid amount. My wife also had a full-time job, with benefits. In addition to all that, I spent about 10 years refining other skills outside of tech that I was planning on leveraging. Lastly, I had that docu-series looming over me – a paid project that needed to be finished.
My plan was to relax, recoup, and become a professional storyteller. Hopefully, as a documentary storyteller.
That next week was my first week in 20 years that I did not need to work. It felt wonderful and really weird at the same time. I had time to relax but also time to work on my ideas, including that docu-series that I didn’t have energy for. So what did I do? Chill, relax, go offline – Nah, I worked. I curated that idea list and I planned out a strategy to finish my docu-series, but rest, I did not.
So the stars aligned, great, where to start? It’s obvious right? The docu-series. I then spent the next month and a few weeks heads down editing. I already had all the filming and interviewing done, so this was the last leg. This part was hard. I started, then stopped, then burned it all down, and started again. I actually did this three times. I am a very fast and efficient editor, so I can do that and not lose much momentum. I even switched between Premiere Pro and Final Cut Pro X at some point. After a month and a half, I released the last episode of The Gray Area of Remote Work on August 4th, 2021.
The relief of finishing that project was amazing! A huge goal of mine complete. So, do I rest now? Yeah, I did. It was hard. I took about two weeks of relaxing, playing games, catching up on reading, cooking, and taking a ton of walks. My wife said that she was happy to have me back. Apparently, I was missing for the past 5 years. This time was great, but it was also the time my docu-series started to get some attention. Let me be clear here, it was not a lot of attention, but enough to start pulling me back to work. A few of the people that I interviewed started sharing and they have large followings and are known in the remote work world. I was getting offers to collaborate on projects and to consult around this new idea called remote filmmaking.
This moment seemed huge for me. It seemed like it was going to be the moment where my years of experience paid off. This was the perfect culmination of my storytelling and tech work intersecting right where it should. I did end up doing remote filmmaking consulting which was great, but it hasn’t really gotten that far. I also had offers to speak about remote filmmaking, but that fizzled out too. I did write the most I have in years, both for this newsletter and my new newsletter. Most recently, I started working with a remote workspace consultancy which has been great, but definitely not what I was planning at all.
The point of this recap is not just to hear about what I achieved and failed at, but the point of quitting your job is generally different than you imagine. I did not become a documentary storyteller, yet. I did create a documentary, but with little recognition or popularity. I did grow my newsletter and wrote more than I planned, but did not grow to the scale that I had hoped. I am making steady money and have plenty of savings left, but nowhere near the income that I planned. All in all, it has been great. I don’t feel undervalued, but I am working even more than before. This freelancing, self-employed, contractor thing is hard. It is nowhere near as predictable as a traditional job, which is great and exhausting.
I have learned a lot since June. Mainly, no matter how good you are, how much knowledge you have, success is not always up to you. I have found that success is a combination of what you are good at + who you know. You cannot be successful without both of these. This is my downfall right now. I don’t have a real network of people. I don’t have fans, mentors, or peers. I am planning to go into this more in another edition, so let me know if you are interested in this topic. I have also learned to be agile when you quit your job. Expect to change and adapt, to work more than you did. It will feel more rewarding, but it will be exhausting.
If you are feeling what I felt and have the drive to go solo, do it. First, make sure you have the resources. Second, make a plan. Third, plan to throw that plan away and pivot to what actually works for you. I am not going back to a traditional job yet, I still have faith in myself and the things I make. Faith in yourself is key because quitting is not linear, it’s an unpredictable ride.