The awkward person’s guide to better photoshoots


I’ve been starting posts with “fun facts” lately, so here’s another: I’m incredibly difficult to photograph.

While my wonderful photographer friends (shout out to Jeff and Juliet) would never say it to my face, and the adage “No one likes their own photos!” is fairly universal, I know the above is true for a few reasons:

1) I have an alarmingly expressive face and large, deep, and long dimples. Seriously — I have absolutely no poker face, and I’m a terrible liar because of these damn parentheses carved out of my cheeks. When I smile, my face goes from long-with-high-cheekbones to overly-excited-moon in a matter of milliseconds. Seriously, I’ve had multiple friends tell me I don’t resemble myself in some of my pictures. I dunno whether this would make me a great spy or something, but I hope to find a use for that, uh, talent one day.

2) I feel intensely awkward in front of a camera, despite the fact I love the end results of my shoots. You might not know it looking at my photos, but for every 1 fantastic shot on my site or social media, there are roughly 800 of me cross-eyed, derp-faced, or slouching.

3) I end up cracking loud jokes to put myself at ease. So that means there are a ton of straight-to-the-trashcan images of me with an extra-elongated face forming “o” sounds, half-laughing, or clearly struggling over consonants.

Which brings us to why I wrote this guide:

If you’re a goofy-faced, joke-making, oh-god-am-I-doing-this-right photoshoot strugglebus rider like me, I think I might (finally) be able to help you.

Photos are challenging — and a yuuuuge element of your personal brand if you have one — so I understand the pressure you might be putting on yourself. I put it on myself, too.

You want to look professional. You want to look cool. You want to stand out. And at the same time, you want it to feel like you.

That’s one hell of a balance beam to be walking on, emotionally and mentally.

I’ve been doing roughly 1–2 shoots/year for 5 years now, and I still get nervous every time my over-stuffed makeup bag, pile of wardrobe options, and I arrive on location. It really makes me look back at all those America’s Next Top Model reruns and think, “Damn. Some people get all the talent.”

But don’t despair, my fellow awkwards: If I can do it, so can you.

So here are a few tried-n’-true tips to make you feel at ease the next time you step in front of the lens.

Tip 1: Work with people you trust.

I’m spoiled, because I’ve never worked with a photographer I haven’t known for years. But that’s also intentional.

The awesome humans who do my photos know me very well. They know my voice is loud, and my forehead and eyes can get powerfully line-y, and they’ll tell me when I’m doing that weird thing with my fingers. They don’t hesitate to say “Hill. Chill.”

But if you don’t know your photographer, that’s OK too. To calm your mind, see if you can hop on the phone with them for a chat, or send an email before you work together outlining any concerns you might have.

Do this whether it’s your first time, or you’re a veteran, because it’ll make you feel infinitely better when you’ve told your photographer what to look for, what to avoid, and why.

Tip 2: Plan ahead. Purpose builds confidence.

Fact: It’s a bad idea to walk into high-stakes situation like a photoshoot with no idea of what to do.

So take some time to figure out what you want, and don’t want. What’s going to make you different? What do you want to avoid? Are there any cliché poses, or locations that make you roll your eyes? What do you want to capture about yourself?

For this, I recommend starting with a “Photoshoot Inspiration” board on Pinterest to try and nail down your aesthetic. I have one you can check out right here.

Inspiration matters, because being clear on your vibe helps you get in the right headspace for the big day.

When I did my photoshoot for my website, I sent my photographer Jeff a pile of Terry Richardson and Juergen Teller inspiration, and a ~10 page creative brief about my goals for the shoot.

Was I over-prepared? Definitely. Was it annoying? Probably.

But I didn’t want another stereotypical “personal brand” website, full of stock images of me barefoot on a couch drinking coffee while laughing at nothing in the distance, or sitting on a city curb for no apparent reason, or pretending to be on the phone.

(No hate on people who do this, by the way. There are industries in which that’s a necessary norm.)

If you are a personal brand, remember photos aren’t necessarily supposed to make the viewer feel like you’ve checked off all the boxes of what entrepreneurship “should” look like (i.e. you, barefoot, on a couch). They’re supposed to convey a sense of who you really are. They should feel natural to you.

So I stripped away all those “make me approachable” tropes in favor of things that felt more me — like striking a power stance in high heels on a rooftop, or looking dead-on into the camera with an eyebrow raised, or making silly faces. Because that’s who I am, and the more proud of that I feel? The better my shoots will be.

Tip 3: Practice, practice, practice.

Yeah you heard me. Stand in front of a mirror, and practice your expressions and poses for a while. Muscle memory will be your saving grace when you start to feel that “Gah, this feels so strange!” tension.

You don’t have to grin like a maniac in every photo. Practice calming your face, and creating micro-expressions that feel more natural, and true for you. Stand with your feet one way, then another. Relax your jaw and eyebrows. Open and close your mouth. See how you feel with your hands on your hips, or your arms crossed, or sitting down.

One great trick? Take in a big inhale, and exhale slowly as your photographer snaps your photos. This will relax your whole body, give you something to focus on, and help you look much more calm and collected.

Tip 4: Dress in stuff you feel great in.

In almost every shoot I’ll do 3 different outfits (casual, party-formal, and business fab), 3 different hairstyles, and 3 shades of lipstick.

You’ll notice that in all my shoots, I’m dressed intentionally simply in blacks, whites, and blues. The silhouettes are sometimes unusual, but not so unusual that you’re wondering how I squeezed into them. The only real pop of color is either in my jewelry, my lipstick, or my blazer.

That’s intentional, because a) I often do shoots in front of white walls, and b) too many prints tend to distract me in photos. When I’m dressed in monochrome, or chic contrasting colors, the little voice in my head that’s speed-stressing things like “Omgisthistoomuch? AmItoomuch? Isthisgaudy? WhatamIdoing?!” snaps shut.

But before you go throw out that awesome crazy print dress you planned to wear for your next shoot, remember: This is just my opinion. Dress in whatever makes you feel awesome — that’s the key.

Tip 5: Have a drink.

Yes, really.

Now don’t get me wrong — I’m not advocating you walking on-set with bloodshot eyes and a sloppy grin. Don’t get drunk. Just sip on something like a small glass of wine or whiskey to take the edge off your nerves, if that’s something that you know might help. (No red wine, though.)

Do I drink at all my shoots? Absolutely not.

Will this tip work for everyone? Probably not.

But starting my shoots with some friendly banter and a little nip of something has helped me relax, and have a bit more fun without worrying whether I’m making a strange face. Maybe it’ll do the same for you.

Tip 6: Try to care a little less.

Ask any photographer worth their salt for advice before a shoot, and they’ll tell you the same thing:

“Be confident.”

It’s good advice, but not entirely complete advice for someone like me. While I can feel confident in short bursts during shoots, before long I’m wondering if the photographer thinks I’ve been staring into the distance too long, or if I look too silly, or too serious, or I’m trying too hard, or I’m too… anything.

So my advice? Try to keep calm by not sweating every. single. shot. Give yourself time to warm up (for me, it’s usually an hour or so). Sure, you’ll probably have a few duds when you review the raw footage, but a great photographer will be able to spot, and hone in on, those moments when a sense of power and confidence is coming through your eyes.

And remember: Great photos are a matter of capturing split seconds. There’s no way all of them are going to be awesome — but at least a few will be.

You might blink. One eye might be open more wide than the other. Your hair might be a little out of place in some shots. That’s OK — and the longer you sit with those “off-beat” photos, the more you might realize you actually like them.

How do I know? Because for every photo that hits the trash can, there will be a fantastic photo that shows the world who you are, and what makes you great. And having photos that capture your essence as an entrepreneur, brand, and human? That’s priceless.

So try to relax. Try to have fun. And “Say cheese!”, my fellow awkwards!

Photo by Jeff Weller.

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