6 Secrets to Amazing Headshots

I’m gonna go right out and ask a slightly uncomfortable question. When is the last time you had a professional headshot taken? A year ago? 3? Never?


You know that as a creative entrepreneur, you are the face of your brand. You know your headshot is a big part of the impression you make. And you know an iPhone selfie doesn’t at all cut it.


But if you’re anything like me, even the thought of having your photo taken makes you break out in hives. Nothing feels more awkward than having a camera lens pointed right at your face, right?


I knew it was time to update my headshots when I realized I was working with photos more than 3 years old. And when I had those taken, Wild Olive wasn’t even on my mind. I was trying to get a flashy design agency job!


Needless to say, the look and feel of those shots just didn’t match up with my current brand.


So I took the leap and hired my friend Susie Moreno to take some new photos of me. And I’m completely in love with the shots she captured!


I couldn’t keep the things I did to make these headshots such a success all to myself! 


So here’s a completely self-celebratory post with my face plastered all over it! Along with the 6 secrets that helped me nail these photos so you can get headshots you love too.


1. Know your Brand

This is the first step you should take whenever you’re doing anything for your business. Take a little time to get back in touch with your brand story, your ideal client, your place in the market, and your goals. That will help you plan for photos that build your brand and fit in nicely with your graphics.


When you have a clear idea of your brand in mind, it’s much easier to see what kind of headshot makes sense for you. I know I’m building a casual, earthy, and inspiring brand so the industrial white backgrounds in my old shots weren’t working at all. A warm outdoor shoot made so much more sense.


Strong intentional on-brand headshots don’t happen on their own. You have to do some work, make decisions, and plan ahead. If you need a little help figuring out your brand, sign up for 5 Steps to Brand Clarity, my new email course coming this winter!
Outdoor Earthy Headshots


2. Make a mood board

Once you have a decent idea of the style you’re going for, put some imagery to your thoughts by creating a Pinterest board. Do a search right on Pinterest, but also add in photos you run into on Instagram, Facebook, and the web that capture the overall style you’re going after.


A good moodboard is a great way to communicate your vision to your photographer and make sure you’re both on the same page. It can also help you brainstorm locations and start a list of places you might want to shoot at. And it can help you plan your wardrobe changes since you’ll have outfit ideas in the photos you’re pinning.


Once you have a few photos collected, step back and take a look. Is there a cohesive aesthetic to your board? Does it feel on-brand? And does it communicate the most important tones and feelings you need it to?
Headshots Moodboard

3. Hire the right photographer

I kind of lucked out on this one because I have a really close photographer friend who just happens to take amazing photos that totally fit my brand. But if you have to look for a photographer, this is what you should do:


First, make sure their style matches your brand. Photographers develop their style over time. You shouldn’t expect your photographer to completely change it up for your photoshoot. Look through their portfolio and compare it to your Pinterest board. How do they match up?


Then, meet your photographer ahead of time if possible. At the very least, try to get them on the phone or a Skype call. Being in front of a camera can be awkward. You want someone on the other side of the lens who makes you feel comfortable. Bonus points if they can make you burst with laughter! 

Casual Laughing Headshots


4. Plan your outfits

Dressing on brand is a whole other blog post just waiting to be written, so we’ll stick with the basics for now. Use the moodboard you’ve been working on to narrow in on the style that makes the most sense for your brand. Does your brand call for a super professional look, something pretty a-la Jessica Day, or a completely casual outfit? 


Next, look at your brand colors. You don’t necessarily have to dress in your official color palette (actually, I might even discourage that a little bit), but you definitely want to wear colors that compliment it. Think of where you’ll use your photo and what colors it will need to flow with.


Now, look through your closet and see what you’re working with. Chances are, your personal style is already pretty aligned to your brand. In my case, all I really needed was a new sweater and shirt to complete my outfit lineup. I headed to the mall with a short list and called it a day!


Try on all your outfits to make sure they all make you feel amazing! If something happens to be on-brand and really really pretty, but it makes you feel totally uncomfortable it’s not going to give you great photos. Go only with the clothes you feel like absolutely amazing in! 

Casual Outfit Headshots

5. Pick a familiar location

Since I hired one of my close friends to take my photos, we considered making a fun trip of our photoshoot. We would explore the small towns between our two cities and find chic little coffee shops to stop and shoot in. It sounded like a really fun day, but in the end, we ended up shooting at one of my favorite parks here in town.


Going somewhere familiar means you know you’ll get the shots you need. You’ve probably already pictured them while you’re there! Plus, it allows you to share a sneak peak of your life with your audience. Whether it’s your favorite chair in that coffee shop or your family’s favorite hike, a personal detail add depth to your shots.


Shooting in one of your favorite places will also make you feel more comfortable. For me, the thought of people staring or even just walking by while my photo is taken feels super embarrassing. But at this park, I knew we’d have enough privacy and quiet to keep me comfortable.

Headshots in the Woods

6. Embrace body positivity!

All the careful planning I did for this photo shoot definitely made a big difference. But the biggest game changer, what really made me absolutely love these photos, was finding the body positive movement a couple of years ago. I’ve been working hard to get past my body image issues and love myself exactly where I am. And it’s totally paying off!


Not only was I able to relax and enjoy the photoshoot because I wasn’t worried about a roll or my double chin showing, I can also definitely see my hard-won confidence shining through! It looks amazing and it feels even better! And for the first time, I was genuinely excited to get my photos and look through my gallery.


Getting past those nasty thoughts we all have about ourselves does wonders! It makes you more confident in your photos and able to see your them for what they are. But the benefits go far beyond your headshots!


So start telling your “problem” areas that they’re actually beautiful. Start smiling at yourself when you look in the mirror. It takes time, but it is possible to learn to be kind to yourself. 

Confident Headshots are Possible!



I know getting your photo taken can feel nerve-wracking, but I hope these tips help you plan a fun and empowering photo session so you can finally replace that selfie with a professional headshot that you love.


Is it time to update your headshots? What would help you take the leap? Tell me in the comments below!

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