Getting Started With My Headshot Photography Journey

2026 marks the fifth anniversary of starting my portrait and headshot photography business (May is the actual anniversary), so I have decided to publish a series of articles to recount the process, hopefully providing some meaningful lessons along the way. Since 2023 I have also offered photography education in the form of workshops and mentorship, if what I say over this writing resonates, feel free to reach out - I take on a small handful of mentees per year.

Over the next ten or so weeks I will publish one article per week with a different theme that outlines the hows, whys and whats of running a photography business. Alongside this, I will gather together the most helpful lessons I’ve learnt into a series of “guides” that will be available to purchase on my website - click the link below to sign up to the mailing list so you’ll be notified when this comes out. My hope is that my stories will help people realise not only what is possible when you combine the art form of photography with the life changing potential of running your own business, but also give some helpful advice along the way that can be used to further your own portrait photography career. This will be written as a series of anecdotal vignettes rather than a step by step guide - my journey will be different to yours, my experiences, advantages, preferences etc are not universal, and any approach that tells you there is only one way of doing things when it comes to the complex world of the business of photography, is bullshitting you. However, there will be some universal lessons that can be drawn out, extrapolated, and adapted - so if you’re looking for advice, keep your peepers peeled. I will do some of the extrapolating work myself and try to formulate some advice along the way.

As you can probably already tell, my writing style is not going to be algorithmically optimised, parsed by Ai or written to capture the attention of distracted readers - the posts will live on LinkedIn and Substack (or at least shorter versions will) in order to reach as many people as possible, the blog on my website (the extended versions) and at some point I will make them into videos for YouTube and carousel posts for Instagram. I’m being transparent here because this is also a marketing tool - and hopefully you can get to see in real time the way I use content production to drive traffic to my website.

A note before we begin chapter one; I have a long background in academia, art, politics and philosophy - I have a PhD in art theory and teach in a politics department, all this to say, I have been actively engaged in art production, display and curation for twenty plus years, and I have been a socialist (or near as dammit) my entire adult life - and yes, starting and running a for profit business has challenged me in ways I didn’t expect. As much as I maintain that its perfectly possible to hold a socialist political position and run a business, the last five years has definitely sharpened my mind about this - I will address the potential contradictions of this in a later post. But, fundamentally, the core principles that guide my socialist beliefs around justice, care, humanity, the environment, equity etc are also the ones that guide my business.

Now, on with the story.

When I first started taking photos back in 1996/7 with my dad’s Pentax film camera I had no idea what the future would hold - and ditching the photography entirely after a year’s foundation course at Exeter College with Pat and Pete - my first experience of wonderful art educators - certainly didn’t indicate I would take the art form seriously. But, twenty something years later, and here I am making a (decent) living with a camera in my hands. I spent the intervening years in art education, curating exhibitions, running galleries, getting disillusioned with the art world after being treated like shit by some collaborators, running art residencies, organising conferences, doing a Masters and then a PhD. It was only when that big thing happened in 2020 did I pick up the camera again.

I was lucky, my flat in SE London had a spare room that I could turn into a simple studio and for the first six months of the business I used that space. I mounted three constant lights on the walls on accordion arms to allow some adjustment and got myself some simple modifiers. As many aspiring headshot photographers do, I found Peter Hurley’s Headshot Crew early on in my journey and joined up, learning lighting, posing and simple guidance for how to shoot the Hurley style headshot - in all honesty this was a steep learning curve and getting to know lighting quickly was very helpful, but the process has its limitations and I don’t think I really fit into the vibe of the Crew. So after a few months I left, staying in touch with Ivan Weiss, a portrait photographer based in London who I had become friends with. Ivan was a decade ahead of me in his business and had a lot of helpful insights at the beginning - often acting as an unofficial mentor when I needed some advice.

During this period I did a number of things that I think set me up well for the rest of my business journey. The first, and most important thing, I shot all the time. I nearly always had my camera in hand - not just portraiture, but street, landscape, cityscape, documentary style. I always wanted to see the world through the camera. I knew because I wasn’t a youngster any longer, I had to work twice as hard and push myself to create constantly. Improving shot by shot, session by session. Just to make sure that I got to a place I was able to bring in clients and provide the best possible photography and service as quickly as possible. These days, whenever my mentees are struggling to get past a problem, I always tell them to “shoot through it”. Keep trying out ideas, keep practicing. I would always want to update my portfolio as regularly as possible - if there was an image in there more than eight months old, I should get rid of it - not because it was bad, but because my work would be progressing quickly enough to make it obsolete, not representative of my style or skill level. These days I can be more chilled about it as the style progresses much more slowly.

The second thing I did during this period was to listen to, read, watch and basically consume everything I could about photography - lighting, posing, editing, business and marketing. And not just portrait photography, I would watch Mark Denny and Henry Turner standing in fields taking photos of their respective local mountains, I poured over the wedding photography stories of people like Jessica Kobeissi, or lifestyle and fashion shoots by Vuhlandes. I watched these young photography YouTubers talk about their craft and passion every day. I listened to business podcasts on my bike rides, or as I edited. I watched Chris Do talk about pricing countless times. And all of this was a continuous stream of fuel to the fire under my arse. I still listen to podcasts and YouTube videos regularly - but during that first two years, I was voracious.

The third thing I did was shoot my friends. With a camera. There were two specific friends, Devyani and Sanjit, who I did some lovely early photos of. And both of them were incredibly helpful - posting those photos to their Linkedin, Instagram and probably even Facebook profiles. From these two alone, I got numerous clients through word of mouth. It was a vital start to my lead generation process. I am still in touch with some of the amazing clients that came from those two posting, and am still generating business from those initial leads.

During this early stage of my business I was nowhere to be seen on Google - buried deep in the basement of the search engine - so had to rely on Google ads, word of mouth and networking to generate any leads. Most of my business spend went to Google ads, just to get to the front page now and then in the hope that people would click. And they did! I managed to generate fairly consistent, if not massive amounts, of business by running adverts. By mid-2024 I was spending somewhere in the region of £1700/month on these ads (right until I realised I was number one on organic search - but that’s another story).

During this first year I was fortunate enough to catch the attention of another headshot photographer, Dwayne Brown. Dwayne runs Headshots Matter, and he reached out to me asking if I’d like to join. HSM is a growing group of headshot photographers all over the world, and joining has been by far and away, the best decision I ever made. Not only is the group supportive, helpful, engaging and constantly challenging, but its exactly what a group like this should be, encouraging of difference - different styles, different ways of running a business, different approaches to the photography journey. And all of this comes from the kind heart of Dwayne and his lovely partner Jennifer. More recently I have been fortunate enough to get more involved in HSM, joining them to become a mentor - something that has brought be great joy over the last few years and combines my two loves - photography and education (I have taught at university level for over twenty years).

There is so much to recount about these first years of my business, and in the next articles I will do a deep dive into some of the important decisions I made, some mistakes, and some wins. One win in particular this year has been to cross the £360k turnover threshold, which has been quite astounding, and the plan for the next five years is to get my regular turnover to around £250k sustainably. I will track how I do this on these articles going forward.

Next week join me to talk in more detail about generating leads through multiple avenues - and what I wouldn’t do if I had to start again.