You Work For Yourself, or How To Fire Your Boss


Depending on who you talk to, I’m either a half-retired entrepreneur or a lowly wage slave. You can read about my five sources of income and decide for yourself. Whatever you think of me though — and whether or not you think of yourself as an entrepreneur — doesn’t matter today. All you need to know is, starting today, you work for YOU. You no longer answer to a boss or clients you don’t want to. You’re now in charge of everything. Your only goal now is building the career life you’ve always wanted. Here’s how.


I get it: It’s easy to feel trapped by a job. Remember “K”? He’s now welding long hours with a nasty 1-hour commute every day. Even at one of my workplaces, management changes are happening, and it hasn’t exactly been sunshine and rainbows. I started looking at other opportunities for the both of us. In just minutes on Craigslist, I’d found backup options. I found “K” a welding opportunity in the same city, and it had the potential to reduce his commute time by 75%! I found a job almost identical to mine on the other side of town where there’s considerably less traffic, potentially saving me time and gas! In the end, we decided to stay at our current jobs, but feeling trapped was no longer an issue. We weren’t, and we came to realize we were never really trapped in the first place. There were always options, mere minutes away and at our fingertips. I don’t know about you, but to me, that sounds like I can “fire” any job I don’t like and “hire” any job I want. If that doesn’t sound freeing or realistic to you, here’s a practical way you can get closer to making this a reality.

Losing income between jobs is a real problem. This is why virtually every personal finance writer suggests creating an emergency fund. A simple three months of income stocked away is all you need to become a boss. It automatically increases your “hiring” and “firing” abilities, and gives you more time to find the work situation you really want. You’re no longer taking the first thing that comes along so you can put KD on the table. You have the freedom to flip through job descriptions — I think of them as résumés — and “hire” what’s right for you! Build an emergency fund that covers three months of income. If you feel like you can’t climb the job ladder, there’s your first rung.

Pull this off properly and your whole worldview might change. You might realize your “boss” isn’t really the boss of you at all. They’re just a coworker. The tasks in front of you aren’t mandatory. It’s a gig you’re doing, and you get to choose if it’s worth it. Feel stuck? You’re not. You have THE ENTIRE GODDAMN INTERNET to help you find a new job to hire. Don’t like your job? FIRE IT.

I’ve always told freelancers they should make every job decision based on passion, profit, and prestige. Whatever you’re doing, do it for at least two. Start thinking of yourself as a freelancer, and think of your bank account as your business. Job hopping is the new normal anyway, so in a way, we’re all freelancers.

The truth is you’ve been your own boss all along. Are you ready to work for yourself?


Pride Was Making Me Poor

my pride cost me

When people ask me what I do for a living, I don’t even hesitate. “I’m a wedding photographer,” I tell them. “I’ve been doing it for 10 years!” Lately, the next question has been weirder: “So you do it full-time?”

That’s usually where my brain stalls.


The truth is, no, I don’t do it full-time. I haven’t done it full-time since 2015, but how do I explain to people I was only shooting “30 days a year” and making ends meet, but decided to take on “three days a week” working at a liquor store too? A quick bit of napkin math then reveals an unglamorous truth: I actually work as a liquor store clerk 5x more than I do as a photographer! Though being solely a wedding photographer was enough for me to get by, I realized that a boost in income from working a regular job too allowed me to save more, attack my debt, and get out of the house more. By the numbers alone though, I’m more a liquor store clerk than I am a photographer! WHY WAS I LYING TO PEOPLE?

Well, there are two answers to that: 1) It’s a matter of marketability. In order to get more wedding bookings, I needed to present myself as a wedding photographer first. Presenting myself as a liquor store clerk isn’t gonna get me more liquor store bookings, ya dig? 2) I had a lot of pride associated with being a wedding photographer. Entrepreneurship was sexy, wage labour was not.

I was actually turning down shifts because in my mind, I was a wedding photographer first. It wasn’t until I decided to help my coworkers out during the holidays that I realized how much I was saying no to. In 2017, because there were times I’d rather be sitting at home just content with being a wedding photographer, one of my lowest liquor store paycheques was $389.14 for two weeks. My most recent paystub just arrived: If I pushed my limits a bit, two weeks could net me $1,048.01! My pride cost me over $1,300 a month.

Someone coined a word for this a while back: “egotrage”, what Mr. Groovy calls “The strategy of advancing your financial position by doing something that is ‘beneath’ your socioeconomic status.” In that article, he talks about how his ego kept him from attaining wealth at an early age. “A man of my stature–I did have an illustrious journalism degree from Long Island University, after all–didn’t wash cars.” (Sound like anyone you know?)

I’ll just admit it: I was afraid. I was afraid that working 40 hours a week doing wage labour would somehow negate everything I’d built as an entrepreneur. In reality, I’m adding to it. The extra income will allow me to buy that Profoto A1 with less financial strain on my business. My seniority at the store will allow me to increase my flexibility with time off, letting me take on new photo opportunities. Simply getting out of the house will improve my mental health and allow me to form new connections with people. It was all an obvious win, but my pride was holding me back! Well, it’s time to let that go. From now on, I’m no longer allowing “wedding photographer” to be my defining attribute to the detriment of everything else.

On the other hand, I have no idea how to introduce myself at parties now. Thoughts?


“So, what do you do for a living?”

“Uh, I’ve got, like, five jobs. Can we please talk about something else?”