How I accidentally became a professional portrait photographer

TLDR: watch this 4-minute video instead 😅

This is the story of how I accidentally became a professional portrait photographer. 

At the end of last year, I left Amsterdam and moved to Toronto with my wife Michelle. My plan was to rejoin the world of advertising after spending a few years working in tech. First, for a Dutch startup as a full-stack developer, before I co-founded Troopl.

Now, I’m no stranger to Advertising. I have several years of experience as a copywriter & creative director, a handful of awards, and an award-winning (and somewhat reasonable) portfolio of work.

So, I naively arrived in a new city, with no contacts, and not enough winter clothing thinking to myself: “It shouldn’t be too hard to get a job, right?”

Oh, how wrong I was.

Because I spent my first few months in Toronto being rejected and ghosted by almost every agency in town.

By this point…I’m starting to get a little bummed. I start questioning what I’m doing with my life. Whether I’ve completely ruined my career by leaving advertising in the first place. Whether I should become an Uber driver. Whether Uber would even hire me!?

On top of all this, I haven’t been creating. I haven’t been coding… I haven’t been writing... I haven’t even been shooting.

All I’ve been doing is working full-time at having (metaphorical) doors slammed in my face.

So I decided to try to get myself out of my funk by shooting some portraits — which are one of my favourite things to shoot.

For years, I’ve shot family, friends, colleagues, and pretty much anyone I can get in front of my camera for a few minutes. See above.

But I’m new to Toronto and I don’t really anyone. Which means I don’t have anyone to shoot a portrait of. (Because there are only so many portraits my wife can endure!!)

So around 1 am on a whim, after re-working my portfolio and resume for the 100th time, I fire up Reddit and post that I’m shooting free portraits in Toronto for anyone who wants one and I share a link to a few of my favourites, including the above.

Then I went to bed, hoping — best case scenario— maybe one or two people might be interested. 

Maybe.

The next morning I fired up Reddit while having my morning coffee and was blown away by what I saw.

Already, I’d received about 50 DMs from people requesting a free portrait. Plus, countless more comments on the post. And this number would continue to climb into the hundreds over the course of the next couple of days.

I was completely overwhelmed by the response. And completely humbled that so many people liked my work enough to want their own portrait.

My funk was starting to subside!

Now, I’m aware that the internet loves free stuff. And this was on my mind as an entirely rational explanation for the outrageous number of responses.

But as I started going through the messages and comments and organising shoot times, something interesting happened. 

Among the hundreds of requests for a free portrait, there were real paid job offers. 

Production companies, businesses, startup founders, and a bunch of strangers from Reddit reached out asking for my rate and availability. This confused me. Because I not only didn’t have a rate… but I’d literally just offered to shoot for free. I really wanted to practice shooting portraits but — mostly — I just wanted to start creating something — anything — again.

But here I am with a handful of paid job offers to do something that I legitimately love doing yet have somehow never considered doing professionally. Which is strange, because much to my parent’s dismay, I’ve had quite a few careers over the years. (But that’s a story for another time.)

Now, as I’ve started shooting the free Reddit portraits, something else interesting has happened. People have started to pay me small amounts for shooting their portraits.

A few of the things I’ve received so far:

• A shelf

• 6 bottles of wine

• A giant bag of Lindt chocolate

• Chocolate

• Special Maggi noodle flavour

• Several tips of various amounts

• Coffee

• Thank you card containing cold, hard cash

• Dinner offer

Now I’m still not 100% sure if this is because my work is good, or it’s just that Canadians are the nicest people ever, but it’s inspired me to give shooting portraits professionally in 2023 a go. 

Because if I can get paid a little bit by putting myself out there for free work. Maybe — just maybe — I can get paid enough not to starve to death by putting myself out there for actual paid work. 

So I’ve just launched my new portrait portfolio (which you’re reading this blog on) and I’m going to keep documenting this journey and see what happens. 

I am 100% not prepared for this. But if there’s one thing I’ve learned from trying to build a startup is that the best way to start anything is to just launch too soon and then figure it out as you go. 

But my startup didn’t really work out… so perhaps that isn’t the best advice. 

Well…wish me luck!