The Clothesline by Vanessa Chiasson

The Clothesline by Vanessa Chiasson

Headshot tips & tricks for freelance writers

Yes, it's time you updated your photos. Really!

Vanessa Chiasson's avatar
Vanessa Chiasson
Jan 16, 2026
∙ Paid

Let’s talk about resolutions and goals for a moment, shall we?

I know that ‘getting new headshots’ is on many of your lists, and for good reasons. As much as we thrive with written material, our work requires us to put a face to a name from time to time. You need to put your best foot/face forward for your website, your social media channels, and the many bios you’ll have in publications throughout the year. Additionally, in a world saturated with AI-generated images, with readers rightfully questioning what’s authentic and what’s manufactured, seeing your face and trusting in it matters more than ever. A great headshot makes you look your best, but it’s not hyper-edited. You still look like YOU, just with great lighting and extra shiny hair.

​Of course you could just use a great photo you happen to have. If you have a lovely yet professional photo of yourself, use it. Or if you think there’s a solution that doesn’t require a professional photographer and that works for you, go for it. I’m all about saving money! But I think there are a few things to consider here.

First, we tend to cling to older photos of ourselves, photos where we look a little bit younger and perhaps a little more svelte. We need photos that look like the people we are now, if for no other reason than to avoid people’s shocked faces when they meet you at a conference and realize that you’re no longer 27 years old. ​

Secondly, a good photographer gives you directives. When I went through the headshot process, the photographer said things like “dip your head down a tiny bit to the left” or “now raise your eyes up and to the right”. At the time, I felt silly. Now I realize they were very subtle shifts to eliminate shadows and catch the light. I’m glad I went with a pro.

I did feel a bit awkward tilting my head and adjusting my arm positions.

So how do you go about getting headshots – headshots that you’ll love?

Method One: The Sensible Method.

Step one: Crowdsource some recommendations. Ask your network to suggest photographers Check out their websites. Do you like their style? Do you like the packages they offer? Go with your gut.

Step Two: Crowdsource some clothing recommendations. Ask your spouse or best friend which of your three blue shirts looks the best. (When in doubt, always go with blue.)

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Pro tip: Oversized elements (like a bold pattern on your shirt or statement earrings) might overwhelm your humble headshot. Tiny details (a lightly patterned tie, dainty jewellery, subtle lipstick) disappear when your headshot is cropped, reproduced, or published in grainy black and white. When in doubt, opt for clean lines and a medium-scale for accessories.

Step Three: Once you’ve booked your appointment with the photographer, book an appointment with your hairdresser. Everyone looks better with a fresh cut and a fresh blowout.

Step Four: Think about what you want to convey with your photos and have a frank conversation with the photographer. Do you want to appear scholarly and serious? Do you want to appear warm and approachable? (Honestly, this is the hardest part of the process and also the most overlooked).

Step Five: Crowdsource the results. Most photographers take many photos, and you get to choose which one (or ones) you keep. It never hurts to ask people to vote on your finalists. Sometimes we play it safe with our own image, and it’s always illuminating to hear what others think looks best on us.

Same photo shoot, same outfit, but one photos uses a shawl and hides the necklace, while the other uses a blazer and highlight accessories.

Pro tip: If you can afford it, opt for a package that allows for an outfit change. You’ve put a lot of time and effort into organizing this photo shoot – changing up your look halfway through is like two photo shoots in one. It’s often very helpful to have two different looks to choose from in the results. Perhaps you want something relaxed and inviting for your website (like a soft sweater) but something more structured and professional for your byline images (perhaps a blazer and bright shirt?)

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Method Two: The Vanessa Method.

Take all the steps above and obsess over them, knowing that a headshot isn’t just a photography session. It’s a line in the sand, a benchmark by which you need to assess who you are, where you’re going, and how the difference between the light blue shirt or dark blue shirt is going to make or break your professional future. And, come to think of it, maybe the shirt should be green.

You can be damn sure I booked a haircut before my headshots. I also booked a blow-out on the morning of, and I spent the month leading up to the shoot using a variety of products that promise to tame my frizz and add a youthful shine to my hair. I found them at the drug store while I was searching for a mega-whitening toothpaste, something recommended to me by the aesthetician who waxed my brows, extracted my pores, and tried to do something about the circles under my eyes.

I wish I were kidding.

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