Your Work

About a year ago, I posted a video on Instagram with the caption, “I QUIT MY JOB,” to announce just that — I had quit my job, and was committed to growing The 1440 full-time.

In that caption, there’s a line that reads, “committing yourself to something that you feel at your very core is your work.”

Damn. That sounds pretty slick right? Some of you read that and feel inspired. Some of you read that and feel frustrated. You begin looking around and asking, “am I doing my work?”

What is your work?

At the time of the post, and for the 6-months leading up to it, I was still in the honeymoon phase of being an entrepreneur. The 1440 was my side hustle; I still had a regular pay cheque from my full-time job in tech. But I had created something, and it felt good. It felt surreal. It felt big, way bigger than it actually was at the time or is currently.

It didn’t feel like work.

Until it did.

If you embark on the journey of starting your own business, most of what you’ll find online is a mirage of romantic and inspirational Youtube videos and articles from Fortune 500 CEOs and founders telling you to quit your job, tough it out, and pursue your passion.

After all, if you do something you love, you’ll never work a day in your life. Right?

Is that good advice?

I’m not so sure.

I love what I do. But I work way harder than I ever did before, and I still wake up feeling stressed and scared shitless that it might all go down in flames one day…

The key piece of this puzzle is one word. Work.

One of my good friends and clients sent me this article last week called Stop Asking Kids What They Want to Be When They Grow Up, and it re-focused me in a way that I didn’t know I needed.

My favourite excerpt from the article is about job expectations. Grant writes, “Instead of painting a rosy picture of a job, you’re better off going in with a realistic preview of what it’s really like, warts and all. Sure, you might be a little less excited to take it, but on average you end up more productive and less likely to quit.”

While you scroll Instagram during your lunch hour or to keep from falling asleep during the next Zoom meeting, keep this in mind. No one is just earning passive income because they’re lucky. Everything comes at a cost.

When you quit a job and start your own business, it’s all really exciting in the beginning. There’s this huge build up and every decision you make feels meaningful. You feel hugely prideful and free. You boast about “being your own boss.” Sidenote: whenever my fiance would ask me if I could do something, I used to say, “let me just check with my boss real quick,” then I’d look up for a moment as if I was peeking into my own brain, and then go, “yep, he says it’s cool.”

That joke wasn’t nearly as funny the second time. After the 3rd time, her eyes were rolling before I could say “let me check wi…”

You get the idea.

The drain that I’m circling here is the work.

No matter what you do — whether you enjoy it or not — nothing works unless you do.

The only difference between being an entrepreneur and an employee is getting to decide what that work is. If you feel like you’re on the edge and ready to make a change, consider reading the article above first, and then deeply consider exactly what work you’re signing up for.

None of this should be read with a tone of regret — I know I’m doing exactly what I’m meant to be doing. Rather, the advice that’s more relevant is to start trying to figure out what your work actually is. This process usually starts with figuring out what it feels like to do someone else’s work first… (ie. that job that you don’t like).

Nothing works unless you do.