9 things I’ve learned after my first 3 paid portrait shoots

A few weeks ago, I had my first paid portrait shoot since announcing to everyone I know that I was giving full-time portrait photography a go. Naturally, it was a big moment. I also learned a few things which I was excited to reflect on and share.

But before I got around to sitting down and writing this blog post, I landed another paid job. No biggie, I figured. I’d just write about everything I’ve learned after I’d finished my 2nd job. After all, two shoots worth of learning and experience would be better than one. 

But before I could sit down to write after finishing that job, I booked another. 

And now between booking, shooting, retouching, and delivering the portraits for my 3rd paid job… I’ve had several more bookings. 

Which is great for my slowly growing photography business. But I’ve come to the — perhaps overly optimistic — realization that there’s probably never going to be a perfect time, when I have absolutely nothing on my plate, to share my journey and write these blog posts and make YouTube videos. 

So, I’m just going to have to make the time. 

Now, in the spirit of 100% transparency and honesty, I’m figuring everything out as I go. Besides knowing how to take great portraits, I have no idea what I’m doing. And with only 3 paid shoots under my belt, I’ve got a long, long way to go before I know what I’m doing and can reasonably offer a portrait photographer any sort of advice or guidance. 

But I have learned a few things. Things which would have been handy to know before I began this journey a few months ago. So I guess this blog post is really for me from a few months ago. (Or anyone who’s just starting their portrait photography journey.) 

So let’s get into it. 

1. Getting paid to do something you’d do for free is an incredible feeling

This shouldn’t come as a surprise, but if for some reason you’re wondering how it feels to turn a long-time hobby into a profession and essentially get paid to do something you love… it feels awesome! 

It’s kind of like being paid to eat ice cream, as silly as that might sound. Picture this: you’re going to eat an entire pint of Ben & Jerry’s regardless. But if someone was to pay you to do it, how much sweeter would it taste?

2. Some people won’t value your work. But some people will.

It’s tough putting yourself and your work out there day after day. You’re going to meet people who won’t value your work and won’t be prepared to pay your rate.

There are going to be people who will lowball you, people who will try to negotiate a package deal to give themselves a handsome discount, and others who will straight up tell you that they thought you’d be cheaper because you’re just “starting out at photography”. And this — unfortunately — is just the tip of the iceberg.

But this is 100% part of the process of putting your work out there. And that’s ok. Because while it stings a bit each time someone chooses not to book you, you’re also going to meet loads of people who will value your work, see your style as interesting and unique, and make the decision to work with you.

So it’s best not to try and convince someone who doesn’t value your work that you’re work actually has value. Instead,  move on and spend that same energy trying to meet people who may value the work that you love doing. Because they are 100% out there and 1000% more fun to work with. 

3. People care more about looking good than being in a good photo

This is probably the most interesting thing I’ve learned so far. 

For the personal branding portraits I’ve been shooting, the most important thing for my clients isn’t that the portrait is good (which, of course, is my number one goal). It’s that they look good in the portrait. 

Think about it. Regular people (i.e. non photographers) don’t really care about things like composition, lighting ratios, highlight falloff, colour theory, leading lines, depth of field, and bokeh (to name a few). 

This is why you’ll see people using low-quality, sometimes even out-of-focus and poorly composed, profile pictures. Because photo aesthetics aside, they look great! Even if the photo overall doesn’t.

It’s also why when you’re photographed in a group photo, the first thing you do is find yourself and see how you look. (You know you do.) Because you’re more concerned with how you look than the overall image. 

This was super important to realise. Because I, of course, want to make sure my clients are happy with their final portrait(s). For that to happen, I need to align my goals with their goals and spend more time making sure they’re happy with how they look and how they’re portrayed.

Because the more you care about how your subject looks in the portrait, the better the experience will be, and the happier your clients are going to be with the final result. 

4. Everything takes longer than you expect

I’m an impatient person. When I decide to do something, I want it done as fast as possible and with as few delays as possible. Preferably no delays at all! I hate having to wait and I especially hate being made to wait because of factors outside of my control. 

This is something I’m working on and I’m slowly coming to terms with it. Because the timelines of initial portrait shoots have been very uncertain and have all taken longer than I initially expected.

People take longer to email back than I expect. People aren’t available until much later in the year than I expect. People take longer to book a haircut before they can book a portrait than I expect. 

Everything. Single. Things. Takes. Time. But it will happen. So just be patient.

5. You need lots and lots of leads

This leads me to my next point. Pun 100% intended. 

It can take a long time for someone to go from a lead to a client. So if you want to be constantly working, you need a lot of leads. 

So far, each of my paid clients has come from a different source. The first came from a Reddit post I made looking for people interested in a free portrait. My second client was a friend of someone I photographed from that initial Reddit post, which has since evolved into the Face of Toronto series. And the third came straight from Instagram. 

It’s still very early days, but so far I haven’t figured out a single source of finding work. Maybe I never will. But it goes to show how important it is to put yourself out there in different ways to meet new people. Because you never know who your work will resonate with.

6. You might be a little nervous about taking the portrait, but your clients might be nervous about having their portrait taken. 

You want everything to go perfectly. You want to make sure you get the perfect shot with perfect lighting the perfect pose and the perfect expression. You want the client to be happy. There’s a lot on your mind and it’s totally normal to be feeling the pressure and perhaps be a little nervous about the shoot. After all, nerves are good. They show you care.

But it’s also important to realise that the person you’re photographing might also be nervous. Maybe, like most people, they don’t have their photo taken very often — if ever by a professional. 

(I’m still getting used to calling myself that.) 

Also, people can be a little self-conscious about having their portrait taken. They don’t want to look bad and they’re going to be sharing this portrait with everyone they know and all of their own future clients. 

Of course, you want them to look their best too! So it's important to make your clients feel as comfortable as possible and ensure they know you’re doing everything you can so they look their best.

This is why it’s so important to build some rapport at the beginning of the session and take the time to have a bit of a chat beforehand. If someone is nervous, you’re going to see it in the portrait. They’re going to be guarded and look stern. But once they’re relaxed and the nerves have gone away, they’re going to look confident.

7. Lots of people have had bad experiences with photographers 

This one has come as bit of a shock to me. But it turns out a lot of people I’ve met and worked with have had a terrible experience with a professional photographer in the past. 

While surprising, it highlights the importance of communicating your ideas and process to set expectations. You want everyone to be on the same page and for there to be no surprises or misunderstandings. 

Proper communication is over-communication, as they say.

8. I (probably) spend too long retouching

I don’t think my portraits look overly retouched. And I’m very happy with the final result. But given that I’m starting to be paid for my work, I’ve become very conscious of wanting to deliver the best possible portraits and not let down my client. 

So I’m doing my absolute best to over-deliver.

This has resulted in spending a lot more time retouching than I usually would. While my clients are happy, this extra time has meant I’m left with less time to work on other things, like editing the Face of Toronto series, which is starting to pile up! 

I don’t really have a solution to this yet. Right now, I’m hoping that as my retouching skills improve I’ll become more efficient and learn faster techniques. 

9. I need a better way for clients to select their favourite portraits 

Right now, I’m sharing low-resolution previews via Google Drive and asking my clients to share the filename of their favourite image(s). The system works, but there are a lot of steps in the process which makes it error-prone for myself and my clients.

On my first shoot, I made a mistake and marked the wrong image in Lightroom. Thankfully, it was brought to my attention before I spent several hours retouching. But it could have been an even more awkward scenario.


And that’s it. Thanks for reading this far. 

To be honest, this probably should and could have been 9 different blog posts. And perhaps these are topics I’ll dive into and explore in the future as my understanding and skills improve. 

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I’ve been taking Instagram way too seriously

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The Face of Toronto portrait series