Instagram Photo tips, Pitching and Dealing with Anxiety with Olivia Bossert

I talk to my students and my clients a lot about how important visibility is when you are starting a business. A big part of the success equation is that you need to have people to sell to. 

I see so many people launch their business, launch their website, and maybe even spend months and months creating a product, only to then be let down when they launch it and nobody buys.

That’s why a big part of what I teach in my programs, like Simply Business, is building an audience of people who know, like, and trust you and selling them solutions to their problems. 

And, today, we’re going to talk about a crucial component and skill when it comes to increasing your visibility: pitching.

Olivia Bossert is a fashion photographer and entrepreneur who teaches other photographers how to get clients and how to build their businesses specifically using the skill of pitching. So, let’s jump right in!

If you did like this episode be sure to screenshot and share on Instagram and of course tag me @erinmayhenry and @oliviabossert.

Story telling is at the heart of my work. Always relaxed, natural, romantic and feminine, my ideas stem from a deep fantasy to retain the escapist and ethereal memories and emotions that dominated my childhood.


Olivia has always wanted to do something creative and the fashion industry, particularly, attracted her interest, so when she discovered Flicker at the age of 15, photography became her link between the two.

“There were loads of kids, essentially my age who were also on that website and sharing their photos they were doing. And I was like, Oh my God, people, my age are doing that. So I became obsessed and I stole my parents’ DSLR that they had lying around the house. And I started just learning everything that was to know about photography.”

After graduating high school, she got a degree in fashion photography and has been full-time as a fashion photographer ever since. Plus she now teaches other fashion photographers how to get clients and how to set up their businesses. 

“There are a lot of photographers who teach the technical side of photography, but I’ve always been more interested in the business side of things.” 

The fashion photography industry has a lot of particularities that are not known about in other industries, so she wants to help others who want to get into fashion photography create success.


To be a successful fashion photographer, especially in the day and age of the internet, it’s all possible. So anyone can do it if they want to. It’s just about pushing through and being resilient. It’s about not giving up. 

Olivia started as a wedding photographer, thinking that she simply wouldn’t have access to the fashion she loved from her small town. And….She hated it.

“It was something inside me that was screaming so loudly that I had to do what I wanted to do, which was fashion, that there was no other way.” 

It’s hard, when you are first starting.  There are a lot of voices in your head telling you “it’s impossible”, “stop trying”, “do the thing you have to do to make the money”.

But, it’s about ignoring those voices and being really, really steadfast in what you want.  

  1. Spend a lot of time journaling and exploring your dreams. 

  2. Make a point of looking outside of your industry to get ideas. 

  3. Look beyond your little bubble and see what other people are doing. 

This will help you push through any boundaries and tap into how other people are staying inspired and motivated.

Books To Read To Help You Get There

  1. Feel the Fear and Do It Anyway by Susan Jeffers

  2. Daring Greatly by Brene Brown 

  3. How to Win Friends and Influence People by Dale Carnegie

  4. You are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life by Jen Sincero

  5. You Are a Badass at Making Money: Master the Mindset of Wealth by Jen Sincero


Olivia teaches people how to really get their foot in the door of a very popular industry. And one of the ways in which you do that is through pitching.

Visibility is so important, building an audience is so important and a part of building an audience in today’s sort of digital age is obviously being seen.

Visibility can come in so many different forms: through more traditional media, through collaborations, through podcast interviews, etc, but they all involve pitching yourself and your brand. You have to market yourself to them.

“When I started out as a fashion photographer and I was living in Cornwall, I was really not able to attend networking events, which are the things that most people do, and I wasn’t able to go to meetings that editors of big magazines go. So I was like, well, how am I going to reach these people?”

And the best way to reach people is to literally just email them.

If you want something, all you have to do is ask. The worst that could happen is they say no, but if we don’t ask, we’re never going to get anything. 

It doesn’t have to be as long winded as you think.

  • Find the relevant contact details: Find the company on LinkedIn. The contact information for the relevant person will be on there.

  • Be Personal: When it comes to the emails, you always want to address someone by their first name. If you can avoid emailing that sort of generic email you’re going to be so much better off. It’s really worth spending the time looking for that person to email and you’ll get much more results from that. 

  • Keep the emails as short as possible, sort of like two to three paragraphs. 

  • You always want to include a really short introduction to who you are, your name, where you live, what you do.

  • If you’ve worked for any previous brands or had any previous collaborations that have been, you know, exciting definitely mentioned those, but if you haven’t, don’t worry about it too much. 

  • The main thing that people will be looking for is the value you can bring them. And that is the really key thing. You don’t want to make this email about you. You want to make the email about what you can do for them. 

  • You always have to put yourself in the shoes of the person receiving the email. I don’t know about you, but if you’ve ever received an email from someone and being like, hi, please hire me because I’m really good. And yeah. And then you’re just, you just go, why, why should I hire you? Who are you to like, want to be like why? But if someone emails you and says, hi, you know, I really love what you do. Um, I think I could really help you with this particular area because I can see that it would bring this for you and make it about the person you’re emailing and you will get a million times more replies and more responses than you ever would otherwise. 

  • Do your research: Know who you’re emailing, make it worth their while to read your email and you will be successful a million times over. 

  • Email more
    people than you think

  • Follow up: If you don’t hear back within a week, absolutely make sure you follow-up with someone because that is where you get the golden responses. Because people see that you’re actually serious and you’re taking the time to really, really get in with them.


Rejection is something that everyone struggles with. You will definitely have days where you get something back from someone ultimately saying, Thank you, but no thank you. And that can be really difficult. 

“I’m constantly pitching people and I teach this stuff and I’m really good at this, and I also don’t hear back from like 75% of the people I email. It’s just reality.” 

It’s just about building up the resilience to it and knowing it will get easier with time. Just keep picking yourself up and keep trying because the yeses make those no’s so, so worth it.

You just have to keep trying and pushing for them. The worst case scenario we can think of is you trying all these things, you are pitching yourself and like emailing a hundred people and no one replying never getting booked, but that doesn’t happen. People are really nice. Like 99% of the population of the world are nice people. You understand that you’re emailing them.

In fact, people are expecting you to email them most of the time, especially if they’re in the media or they run some kind of business, they are going to be used to getting ideas for things and they want them. 

“I can guarantee you that writers for magazines want you to pitch their ideas to them because they are running out of ideas themselves. It’s really hard for them to constantly generate ideas and come up with things and come up with podcast guest ideas. So if you think you’re going to be a good guest for someone, you would be almost doing them a disservice by not reaching out to them because they might really need you and want you.” 

So if the fear of rejection is what’s stopping you, getting in the way of yourself, please just think about all those things and just keep pushing through it, reach out for help, you know, make a little support group with some friends who are also doing this and just help one another so that when you do get an email back with a “thank you, but no thank you” or you send out 10 emails that day, you have that place of support.


Take baby steps. Taking one step, 1% towards that thing every single day. 

Talk to the camera on Instagram, for example. It’s about being really brave and just one day saying, okay, one, two, three, four, five, I’m going to do it now. And just getting your phone out, doing one story and then putting your phone away for a couple of hours and not checking it and not looking at how it’s performing or anything like that. 

Our brains are always going to protect us from the scary thing. Our brain doesn’t know the difference between something that’s just scary and something that might kill us. So we have to show our brains that we won’t die when we do things that are a little bit scary. Feel the fear and do it anyway. Just set yourself a tiny little goal, one little thing, go out and do it, see how it feels, prove to yourself that you didn’t die. And then the next day, or a few days later build up that courage a little bit more. Try it one more time. And the more you do it, the easier it gets, the more you realize that you don’t die when you do it.

Take time with yourself, be patient with yourself, but don’t stop yourself because of the anxiety. 

If you keep everything that you want to do just in your head and just is stuck inside you, it will never be able to come out and that can be anxiety inducing in itself. So releasing that in a little small way, can I think really, really help,


Use the Kali Dame Method—She’s also an educator in the photography space and she’s fantastic.

Go on Pinterest and just go wild pinning stuff. Anything that you’re visually attracted to. And then after about 10 minutes, 15 minutes, however long you feel drawn to do it for go back to that Pinterest board and sort of grab a piece of paper and just write any words that come to mind when you’re looking at those images. Is it the colours? Is it the mood? Is it the vibe? Is it the locations? Is it the clothes that are being worn? What is it that you’re keep seeing a recurring theme of? And then you can actually also go through and delete any images that are feeling like they’re not quite speaking to you when you look at it as a whole. And then once you’ve got those words on that paper, those are your like anchor words for your imagery, whether it’s for your work as a photographer or for your work as a coach, and then you want to have in your, whatever those may be, and then keeping that somewhere safe, where you can constantly refer to it. It’s taking all those elements and making it into a nice big pot so that whenever you put on your Instagram account everything ties together because it’s all within that sort of bucket of stuff. 

And it doesn’t really matter how you lay out the images. They will always look good together because everything’s going to be cohesive. And in the little realm of what you’ve created for yourself, if you stray from that, that’s when things will start to look weird.

Like if, if everything you do is very coastal vibes and very pastel colours, and you’re always, um, where the, you know, white backgrounds and have everything very clean, and then you suddenly have a block image of you on a black wall. It will look really weird and it won’t be in keeping with everything. 


  • If you can’t invest in a photographer, then it’s about finding good light. Facing windows is the biggest tip you will ever get. It will make your face look bright and light and you won’t have any creases in your faces. 

  • Take a lot of photos. We’re not shooting on film anymore. So we don’t have to limit ourselves. If you’re going to feel better by having a million photos taken and then sifting through, go for it, you have no limits on how many images you can take. That being said, be kind to yourself and ask your friends and families what they think looks good because we are often the most critical of ourselves.

  • Listen to the people around you who are telling you it’s a beautiful shot and you will have a lot more imagery to choose from. 

  • If you’re asking your partner to take the pic for you, ju
    st literally set the shot up for them, do everything for them, test it with them in the frame, if you need to, and then just show them exactly what you want them to do. Just take the time to show them, set it all up and then have them take a million images. 

  • Keep moving! Every time that button gets pressed, move. It doesn’t have to be a lot of movement. It could be really subtle, like moving your head from side to side, up and down, shifting your shoulders around, lifting your shoulders up, putting them down, moving a hand across…just keep moving. 


“My theory is remove things that would not normally be there, leave everything else.” 

Retouching has been happening since the dawn of time, we’ve just become more aware of it now. And, that awareness is really, really important. 

“I have a lot of clients who hire me specifically because they don’t want their images retouched. They want to keep everything raw and real.” 

If it helps you to get online, if it makes you feel better to put on some makeup or to use a filter, go for it! Do whatever leaves you feeling good about yourself!





Webinar Link: 

If you haven’t already, be sure to join us in the Game Changer community on Facebook or on Instagram – @erinmayhenry.

are you ready to start creating your dream life?


© chillpreneur 2023 | Legal

web design/development by hAus of kyme