I Quit! Why, When, and How I’m Leaving My Steady Job to Run My Business Full-Time

Greg Thumbs Up!

If you’ve read my blog post, How the Hardest Month of My Life Made Me Believe in Myself and Follow My Dreams, then you know that, back in October, I was in hot pursuit of a very enticing Manager role in my own office. You’ll also know that I didn’t get that job and, though it went to a good friend of mine who totally deserves it and has been doing a great job so far, I was crushed

The night after I got the bad news, I woke up at 2:00am, completely unable to sleep. My failure weighed on me and my mind bounced back and forth between the past; replaying every little piece of the final interview to see where I went wrong, and the future; imagining walking into work to face all my co-workers, embarrassed that I was not selected, and then having to deal with the reality of staying in my current job. It hurt. And I could not sleep. 

Call me a weirdo but… 

By 5:00am, after conceding that I would not fall back to sleep, I comforted myself in the most Greg way I can imagine. I sat on the couch, popped open my laptop, and fired up Microsoft Excel. It was time to make some spreadsheets. 

I told you you’d call me a weirdo…

Sometime between 2:00am and 5:00am, I had concluded that I couldn’t go back to my job (which I had been doing for 5 years) without a concrete exit strategy. So I started crunching the numbers to see when I could comfortably afford to leave the working world forever and pursue my business full-time. 

I made a monthly budget to see the bare minimum I needed to survive… it was a lower than I thought. Then I took stock of all my assets (my Tax-Free Savings Account investments, my pension, my business bank account, my personal savings accounts, and my chequing account). Then I estimated how much I could put away from my various income sources per month if I continued doing what I was doing. When I had all the numbers out in front of me, I felt a lot better. I knew that I could leave immediately if I wanted to… 

But... 

I wanted to wait until I had enough money that I wouldn’t have to touch my long-term savings if I needed to supplement my income for the first year or so. And I also wanted a sizable operating budget for my business so that I wasn’t pinching pennies and stunting my growth potential. Long story short, if I wanted the comfortable nest egg that I was picturing for myself, I’d have to stick it out in my current job for at least 9 more months

This left me feeling… still bad… still really bad to be honest. I had an exit plan which would allow me to comfortably leave the world of work and pursue my dreams full-time, but it felt a bit soul crushing to go back to a job that I had grown out of and tried so hard to leave. 

And then...

An opportunity. 

At this point, I have to give a lot of credit to the people I work with. They knew I didn’t want to stay in my current role, so when they decided to give the manager job to my friend, they started looking around for another option for me and thankfully, something came up. 

In fact, the moment I was informed that I did not land the manager job, this other opportunity was presented to me… now at the time, I didn’t care to hear about some random other job (I was a bit distraught), but after settling down and talking to a few people about it over the next couple weeks, I opted in. 

So this other job… 

There’s a lot of really cool stuff about this new job. It’s still at York University, where I’m working now, and I’ll be working with some people who I really like and the job promises to be very challenging (which you know I love). And what’s really, really exciting about the new job is that it’s a 6-month contract. 

6-months. 

Starting at the beginning of February. 

Ending July 31st. 

And then... I’m out!

Done. 

After this contract, I’m leaving formal employment and going full-time as an entrepreneur. ← a scarce few sentences have ever brought me more joy to type than that one. Wow. 

Let me just say it one more time: On July 31st, 2020 at 4:30pm, I will become a full-time entrepreneur (what a way to celebrate Harry Potter’s Birthday). 

I’ve officially given notice at my current job. My final day will be February 3rd and I’ll start the new job on February 4th. 

Since I put in the paperwork to leave, I have felt… a lot of... things. 

I’ve felt super sad to be leaving all my friends and students in my current job. That does always seem to be the way once you commit to leaving. Then again, I’m going to be working about 55 steps from my current desk (same building, same floor) for the next six months, so it’s kind of a gradual transition out. 

I’ve felt anxious and worried because I’ve been living in an unchallenged comfort zone for a long time. I’m giving up my steady income, pension, and all sorts of stability to pursue my goals (luckily I’m enrolled in Ariana’s benefits so my health is still covered). 

I’ve felt lonely in advance. Knowing that I’m giving up structured social interaction (coming to work) and that it’s going to take a lot more effort to see and interact with people. This has been stressing me out a bit… but I’m working on that too!

I’ve felt free because there are a lot of times when I’ve just felt like I don’t quite fit into the box of employment. My bosses have always been great about giving me autonomy to create and lead and everything… I’ve been super lucky with this… but there’s only so much freedom you can get when you have a boss. 

I’ve felt proud of myself because I’ve wanted to do this for a long time and now I’ve finally committed. This is the decision that has felt “right” in my professional life for a long, long time. And it wasn’t easy (it took me years to build up to this), but I freaking did it. 

I’ve felt unwavering excitement for what’s to come, for the possibilities for my business and myself. I see new ways of marketing, expanding current income streams, adding income streams, doubling down on what’s working and always trying new things. Whenever I stop to think about it, my heart starts beating faster and I feel this overwhelming energy surging through my veins. 

It may have taken me a few years to make this decision official… but it happened. I’m doing it. And it feels great!