Corporate 2 Creative, Issue 004: Sara Dalrymple, Headshot Photographer


I left my banking career a year ago now, I remember cluelessly asking myself, What am I going to do now? The response to my following question was the most important of all. Another banking job? Hell no. This was a turning point in my life and similarly so for Sara Dalrymple.

Sara describes herself as a photographer of personality, and I see her as a photographer with personality. Interviewing Sara was like spending time with a friend, right from the moment she stepped into the room and embraced me with a big hug. The immediacy of Sara’s openness became apparent when I listened back to the interview recording - my only regret was not pressing record from the moment we sat down. Having stepped off the muggy Central line tube of the London Underground and climbing the stairs of AllBright Rathbone Place, Sara began to fan herself and share with a smile how much she loves her job.

I was fascinated to know about her transition from a decade of being an investment banker to a headshot photographer, but she paused her interview to get to know me. She was curious about my story and my interview series. Photographers can have a reputation for being mute behind the camera and shy away from the client interaction; I can see what sets Sara apart. After ten minutes of talking, we had spoken deeply about our shared need to change career paths; Sara was intensely unhappy in her job, and I was beyond stressed in mine.

Sara’s tone jumped an octave, “You need someone to interview you - I can do that for you. I mean, if you’d like. I want to hear more!” Maybe one day I’ll take up her offer, but right now, this interview is all about her bold career change. The conversation immediately progressed to her ideals of life and how she went about achieving them.

Over an hour into the interview, I realised we hadn’t had a chance to order a coffee. Long after the Black Americano and Flat White cups were empty, we continued chatting like old pals catching up and insisted on another meet-up soon.

Her story reminds us of how change can be restorative and fulfilling, even when we live in the culturally obsessed notion that financial gain is the exclusive definition of success

Her story reminds us of how change can be restorative, fulfilling and financially rewarding, even when we live in the culturally obsessed notion that financial gain is the exclusive definition of success - whether it’s earning the most in your friendship circle or holding the ultimate corporate title after years of growling study. I’ve been complicit in the belief that financial success is superior to other forms - overlooking the friend taking the brave leap into self-employment and congratulating another on their promotion in a job they endure, ignoring the courage it takes to pursue career contentment.

Sara has been a London headshot photographer for six years now, and since her career transition from the corporate world, she has never looked back with regret. In this interview, she talks me through the culture of the early investment banking years, leaving an unwelcoming parenting environment at work, her first steps of starting a new career and expanding her business.

Anyone who fears to be in front of the camera, as well as the photographer, Sara is your ideal working partner. Sara specialises in working with female founders and creative business owners to produce headshots with personality, colour and none of the cringe. She knows the power of having the perfect headshot to lift your confidence, increase your visibility and grow your brand. She promises to put you at ease, and relax even the most camera shy of subjects. To see Sara’s latest work, check out her website: and follow her on Instagram: @saradalrymplephotography.


Tell me about your earlier career choices.

At school and university, I was one of those people who never knew what she wanted to be when she grew up. After graduating I moved to London and got a job in banking...I had heard a lot about how many opportunities there were in finance for people with languages and it was an industry I knew very little about, and I was curious! 

How were the working hours? Was there a culture of showing your dedication by being at your desk beyond contracted hours?

Working hours were long but not unbearably so, an 11 hour day was fairly typical, and all throughout my twenties posed no problem. The main issue I could see for my future there was that there was no flexible working to speak of at that time. It was a very male dominated team with a typically one-sided approach to anyone having to leave early to pick up children, and even though I didn't have any children myself at that point, I wondered how I'd feel about prioritising getting into work before 8am and being in the office all day long, over anything that was happening at home. I've always been a really dedicated worker, but I was starting to get frustrated with the lack of movement in the way it's always been. I wondered whether there was something out there that would be more flexible that I could do just as well. 

What influenced your career decisions up to this point?

This is kind of crazy, but I realised recently that it wasn't until I was in my 30s that I ever gave much thought to what  I loved doing - how ridiculous is that?! Up until then, I'd always thought of a successful career as being something more traditional, that you didn't necessarily feel amazingly passionate about, but could do well from. At school we were taught that we should maximise our potential and become successful doctors / lawyers / accountants - doing what you love just didn't come up as a credible career path! So I think I was quite influenced by the (entirely incorrect) idea that to be successful you should stick to one of these well-trodden paths. I've always been keen to work hard and be successful, I just didn't realise I could do it for myself until a lot later in life.


Have you always seen yourself as creative?

No, I didn't love art at school and so I always just assumed that meant I wasn't creative. When I look back, I have always loved taking and looking at photographs, and in the pre-smartphone era, I always would be the one packing my massive camera into my handbag to take along on a night out, a wedding or on a girls holiday. Photography was a hobby, not something that I thought could be a career option, but I had got to the point where I knew I didn't want to spend another decade in banking. After we got married and we received our wedding photos back something just clicked in my brain. I'd had a lovely experience with our wedding photographer - I'd been really nervous (because I hate having my photos taken) but my photographer had been easy to have around and got some amazing photos which I just couldn't have been more chuffed with, and I just knew that that was a job I would absolutely love to do.

I'm a real people person and I passionately wanted to make everyone's photography experience feel as positive and relaxed as the one I had. I set about finding a course and the training I'd need, and that was the start of my photography journey. 

I emailed my photographer and suggested a course that he and a few photographers run on wedding photography. It was a year-long programme, and I signed up for the next intake. The course worked out perfectly to coincide with my maternity because I was taking a year off. It was really early on in the course that I knew I was going to give up my job to become a photographer. I was an amateur starting without an SLR camera. I was signed onto an SLR for beginners course before starting the year-long wedding photographer course. I had a mentor, which was amazing, and the course was phenomenal.

How intense was the course? If someone was thinking about doing it alongside a full-time job, would they be able to do it?

You can do it alongside a day job. It’s a year-long programme, and there are six modules and two days a month in the classroom. Once every month you go there and have two intense days of learning and every week or two, you have coursework to submit. The first few months involved lots of photoshoots of different subjects, like couples engagement shoots and group shots of people. I learned how to pose people, how to relax them, find backdrops and good light. You submit the work for critique by your mentor, and you’d have a call to gain feedback. By the end of the module, you would feel like you’ve put into practice everything you had learned in the classroom.

It’s incredible that he was happy to take you under his wing and talk through your options.

Yes, I thought if I had chosen any other photographer, I would never have ever known about this fantastic course. My wedding photographer became my mentor on the programme, and I second-shot at his weddings. It was such a great experience. The course starts you off from zero to at the end of the year you have your website, your accountant, your company is established, and you have on the ground experience. I’m a perfectionist, and I knew I couldn’t be going into anything half-hearted.

I find the feedback can be the most essential part when you are learning something new. You can learn the theory, but it can be challenging to know if you are getting the desired outcome.

The feedback was great. I got feedback from my mentor, he’d say he could see I was interacting with people well and they were relaxed, but my technical abilities needed improving. It felt complex at the beginning but it was what I needed. My mentor and I had a few extra sessions where he’d set me tasks, such as finding a suitable spot of light and backdrop. I’d get immediate feedback because he was right there.

Now, looking back, it is clear to me that it has always been photography for me. I’ve now been a wedding photographer, a family photographer and a headshot photographer - they’re all completely different, and any one of those would be a fantastic job in their own right. I’m learning this late in life compared to if I was 18. I don’t regret any of my career choices, but I do think it would have been a game changer if I had started at sixth form.

What were you feeling when you first jumped into self-employment? Do you associate it with a good time?

Yes, I do. I have never looked back - I know I have done the right thing and I've never been happier with my work than I am now. Of course, there have been periods where it has been overwhelming - running your own business can be hard sometimes, but the good far outweighs the bad for me. Getting the balance right has been hard for me, because I'm a people pleaser so I want to give people what they want right away, but I know my home life suffers when I take on too much; I'm really clear on the fact that in busy periods I'm booked out weeks in advance. 


Do you have a network that feel like work colleagues?

Yes and it’s really great. At first I struggled with being on my own at home all day - I missed my team and I missed being around people. Working on your own, you don't get an appraisal or a friendly pat on the back saying you've done a great job, so you can easily start to question yourself.

My advice is to go out and find people that are like-minded, either in your local area or at networking groups or coworking spaces - that's been a game changer for me. It’s crucial to have friends that are self-employed too I think because they understand and share the same challenges - and wins! 

If someone is starting their own business, would you say that finding a network is one of the first things they should do?

Definitely! Turn up and share your ideas, you'll gain so much because networking events tend to be full of the exact kind of people who are able to help.

If you are introverted and don’t want to meet people face-to-face, then social media is also excellent for building a community. There are lots of ways to get involved and connected now - almost too many - but you pick your favourites and off you go!

Are there any aspects of your photography career that you didn’t anticipate? What would you suggest someone in a similar position prepare for mentally?

Where shall I start?! I'm not afraid to say that I completely underestimated the number of tasks outside of photography which are involved in running your own business - being a good photographer is probably only about 10% of the whole picture! Then there's website designer, marketeer, salesperson, blogger, accountant, social media manager...and don't even get me started on IT! I miss IT support so much because now I can lose a whole day to IT issues (and have done!). 

In a corporate environment, all these aspects are taken care of by another department, so it’s suddenly overwhelming when you’re on your own. I also work more hours now than I ever worked before. I can choose my hours now, which is massively important to me, but I do also work long hours into the evening when I need to. None of this is off-putting to me because I love what I do, and I think that's the key: finding what you love and then accepting that working for yourself is one long learning curve! A very rewarding learning curve. 


How did you find introducing yourself to people as a photographer compared to an investment banker?

I guess the main thing I would say is that I'm always smiling and happy now when people ask me what I do, because it's something I can talk passionately about. It's hard to sound passionate about financial instruments used in the City, but taking photos of people? I'll never get bored of that. What's interesting is that from time to time I'll meet someone who can't get their head around why on earth anyone would want to leave a stable, well-paid job to set up on their own. It's a case of trying to reposition their views so that they understand how fantastic my experience has been!

Did you struggle to assume the identity of a photographer?

Going from a corporate role to a creative career was obviously very different, but it was a positive change. I've always just been myself and done just fine with that. The adjustment was more to do with backing myself and becoming as successful in my new career as I had been in my old one, which felt really important to me. Some people still seem to think I’m the crazy for leaving banking, but I think it's the other way round!  Things are changing, and we don’t all have to go into offices to be successful. Success can be made on your own terms. 

What is your version of success? 

My version of success is being able to work in a job that I absolutely love in a way that suits me, and for that work to allow me to support support myself and my family. 

Thank you to Sara for giving me your time. I loved every moment of speaking with you.

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© Rachel Matthews 2020