New gen bosses is a new series created to guide and inspire more people to go out there on their own, either as new business founders or freelancers. And what better way to do that than to ask the ones that already succeed at it? We want to know about big fuck-ups and even bigger successes, and the risky decisions they had to make along the way. We want to be the last little push you needed.

Job title: Photographer
Industry: Fashion and portraiture
Company founder or freelancer: Freelancer
How long have you been doing it: 5 years
Age: 26
Location: Los Angeles, California

What pushed you to start on your own?

I blame being raised as an only child for a stubborn sense of independence. I struggled with making images that weren’t ‘my own’. Two years ago, this frustration and lack of satisfaction pushed me to save up one month’s rent, pack up my car, and drive to LA. Somehow I’m still here.

What was the very first thing you needed to do to set everything up?

Truly, I just needed human connections. It was humbling when I realised that I wasn’t going to be successful with the stubborn independence I mentioned. It’s impossible for me to make art unless I have humans to collaborate and grow with. Making friends in Los Angeles is difficult, but when you find the right team, everything falls into place.

What was the riskiest decision you had to take?

I had enough money to live in Los Angeles for one month, but I did it anyway. This city loves extravagance, but Trader Joe’s frozen dumplings really saved me.

What was a skill you didn’t foresee needing that you had to learn?

I didn’t expect to interact with so many difficult personalities through this process. There will always be a human that you cannot connect with, a human that won’t speak to you respectfully, a human that doesn’t value your work. The biggest lesson for me was learning to stand up for myself and not compromise on my value.

Everywhere around us, new gens are founding businesses and redefining their careers. New gen bosses is here to inspire those who might want to do the same, this time with extra tips, some lols from those who have been there, done that, and £20 in your new ANNA business account if you dare to take the leap.

At what moment did you realise that this was going to work out?

My favourite memory so far is seeing my cover of Playboy on my friend’s coffee table. Things felt right, yet wildly humbling.

What did you spend your money on?

Trader Joe’s and film processing.

What was your biggest fuck up?

One time my camera was on the ‘emergency setting’ and I shot 40 rolls of film underexposed by 2 stops. That kind of fuck up will teach you to check the emergency setting every dang time.

What was your biggest success?

Oof, this is hard to answer. I’m very proud to have shot the cover of TIME. The amount of respect and reputation the publication has, and the fact that they trusted me to make something. Working with Lil’ Nas X felt like making history. I mean, he did make history. I got to capture that.

What do you know now that you didn’t know then?

I used to think that if you were technically capable, you could be a great photographer. I’ve learned now that my technical ability has become 0.01 per cent of my images. That part is second nature. The rest of my work is my connection with the people I’m photographing. (I’m sure a lot of tech nerds are rolling their eyes at this. Sorry.)

What are three tips you would give someone who wants to start on their own?

One: There will always be a backup plan. Failure is a concept relative to your perspective.

Two: Trust your gut. Trust the images you feel proud of. Trust your intuition. This work is yours.

Three: Stand up for yourself (respectfully, of course). Being an artist is painfully personal. Do not let someone make you feel less than because of the incredible gift you are utilising, nurturing and demonstrating. You’re strong, but you’re also graceful.

Feel like you wouldn’t have to survive on frozen dumplings? There’s only one way to find out. Take the leap, open an ANNA business card completely free of charge for the first 3 months and get £20 in it, too.

Want to discuss taking the leap with other new gens? You’re in luck! We’ve created New Gen Bosses, a Facebook group to continue and expand the conversation started through this new series.

New gen bosses is a new series created to guide and inspire more people to go out there on their own, either as new business founders or freelancers. And what better way to do that than to ask the ones that already succeed at it? We want to know about big fuck-ups and even bigger successes, and the risky decisions they had to make along the way. We want to be the last little push you needed.

Job title: Managing Director 
Industry: Digital Marketing 
Company founder or freelancer: Founder
Company name: The Digital Fairy
How long have you been doing it: 7 years 
Age: 31
Location: East London

What pushed you to start on your own?

Soon after leaving uni, where I was studying communications, I knew I wanted to work in digital. I had an unhealthy addiction to the internet, between my friends, social media was our main communication tool—it was constant. At the time, brands were so boring online and I just had endless energy and ideas to connect them to a fairly untapped digital community. But there wasn’t one creative social media job role in London.

Two of my closest friends were successful business twins, they propelled me to start something, they believed in me and gave me a desk, a small loan, a forecast sheet and my first client, which was Bleach London (a small cult salon in Dalston now a household hair brand). Thanks, Sam and Lou. At the time, a lot of my friends in London were young business owners, creatives, freelancers so it felt scary but exciting and certainly not unattainable.

What was the very first thing you needed to do to set everything up?

Of course, I needed all of the above, but for this to work, I knew that I had to make myself invaluable to clients, so they couldn’t work without me. I was called ‘The Digital Fairy’ so I had a lot to live up to, I needed to graft and up-skill across every area—social media, copywriting, design, development and content creation. I was so basic at most of those things, but I knew when I would eventually recruit for those roles that I would understand the skills I needed.

What was the riskiest decision you had to take?

At the beginning, I was working with a lot of friends as partners, employees, suppliers and clients, and that was risky. There is so much to lose, and while it wasn’t always perfect, I learnt a lot and I gained a lot from starting in a bubble of trust, comfort and support.

What was a skill you didn’t foresee needing that you had to learn?

It sounds obvious but so much resilience. When you own a business it is inherently part of you and your identity, so when something goes a bit wrong it feels personal. It has taken years to begin to train my sensitivity so that I can leave a problem at the office, sleep at night and care less. You also naturally learn strength of character, to keep stable and solutions-focused when absorbing your team and clients’ energies, feelings and problems.

Everywhere around us, new gens are founding businesses and redefining their careers. New gen bosses is here to inspire those who might want to do the same, this time with extra tips, some lols from those who have been there, done that, and £20 in your new ANNA business account if you dare to take the leap.

At what moment did you realise that this was going to work out?

It wasn’t until 12 months—through a relationship and the case studies I’d been working hard on, I got my first big gig doing social media at The X Factor, at the time it was the biggest TV show in the UK and I was just there every weekend, so proud of myself. It led to conversations with other commercial clients such as Maybelline, Miss Vogue, ASOS… brands were beginning to shift into digital. To supply the demand I had to recruit a small team, at that point it just had to work out.

What did you spend your money on?

Like most DIY startups, apart from my essentials, I took a really nominal salary for the first 18 months. I reinvested everything I made back into the company to cushion myself and pay that loan back. I didn’t start spending money until I needed to pay for very junior staff. My next biggest expense would be small gifts and gestures of thanks, it was important that I fostered a culture of appreciation which I still try to keep alive today.

What was your biggest fuck up?

Nothing major to be honest, I feel lucky yet anxious to still be waiting for that big scary thing. But, early on everything was so DIY and scrappy, which made us who we are, but there was no process and I didn’t have the right communication tools. Clients were not contracted, projects were not scoped—everything was based on a vague and friendly understanding—which inevitably led to an abuse of trust and some unpaid invoices.

What was your biggest success?

My first few hires who started as interns have stayed and grown with the company for over 5 years, straight from uni. One is now a senior designer and the other an art director. Above everything and any project, it makes me feel incredibly proud to have created a culture where people can fulfil their long term ambitions, feel safe and develop with us.

What do you know now that you didn’t know then?

That business success to me isn’t about excessive profits and scale, it’s about retaining your personality and integrity, and those things can’t coexist.

What are three tips you would give someone who wants to start on their own?

One: Your business has to work around your personal needs. What are they?

Two: Invest in your staff and company culture—it’s so important.

Three: Don’t allow anyone to be passive in any role, everyone needs a self-starter attitude and everyone’s opinion matters.

Feel like unpaid invoices will never happen under your watch? There’s only one way to find out. Take the leap, open an ANNA business card completely free of charge for the first 3 months and get £20 in it, too.

Want to discuss taking the leap with other new gens? You’re in luck! We’ve created New Gen Bosses, a Facebook group to continue and expand the conversation started through this new series.