“We need to take ourselves seriously as business owners” with Sophie Cross

I heard Holly Dannhauser speak about our relationship with money and immediately thought, I need to get her on the podcast. She talked about how the things we believe about money, what our work is worth and what we should or shouldn’t be earning can influence the decisions we make without us even realising it. And it made so much sense to me. I’ve met so many business owners who struggle with money and their own sense of worth, and I know from my own experience how easy it is to pick up beliefs about money without really questioning where they’ve come from. Holly is the founder of Moon and Mountain. She works with people on the practical business stuff like strategy and direction, but also the things going on underneath that can get in the way, like confidence, money and what we believe we deserve. In this episode, Holly shares her own money wake-up call after becoming self-employed and what happened when she realised her relationship with money was influencing the way she was running her business. We talk about the beliefs and behaviours we pick up around money, why understanding them can help us make more conscious decisions, and why creatives in particular can find it difficult to put a financial value on what they do. We also get into undercharging, overdelivering because you feel guilty about what you’ve charged, and one question from Holly that I’ll definitely be taking away from this conversation: why not me?

I’ve known Sophie Greenwood for a few years now, and she’s one of those people who can take all the ideas flying around your head and help you work out what you actually want to do with them. A couple of years ago, she ran a capacity planning workshop for my Blueprinters that was a bit of a lightbulb moment for me too. Coming from the creative agency world, I’d picked up some pretty bad habits around saying yes to work and simply working more hours to fit it all in. So I knew a conversation with Sophie about planning, capacity and how we actually make our ideas happen would be an insightful one. Sophie Greenwood is the founder of Three Beams Thinking and a strategy and planning mentor for small, creatively minded businesses. In this episode, we talk about those bigger ideas we have for our businesses – the things we’d love to do one day but perhaps don’t say out loud because we’ve got no idea how we’d actually make them happen – and how planning can help you start bridging that gap. We also get into capacity planning, why so many of us overestimate how much we can realistically fit into our working week, and why having a plan doesn’t mean you have to rigidly stick to it when things change. And we talk about how Sophie has gone from chasing the next job, promotion or pay rise to being much more driven by curiosity and making room for work that excites her.

When I first met Emma and heard the story of how she started Bobbin & Bumble, I was struck by how matter-of-fact she was about the whole thing. Because it’s a pretty incredible story. Emma didn’t set out to start a business. She needed a more practical cover for her IKEA high chair, so she bought a £5 sewing machine and taught herself how to make one. Then she realised she wasn’t the only parent looking for more practical accessories for IKEA baby equipment – and what started as something she made for herself gradually became Bobbin & Bumble. All while Emma was balancing work and motherhood. In this episode, we talk about how she went from making products herself at home to building a baby and children’s brand and moving into manufacturing, without ever really having a grand plan for where the business would take her. We also get into something I found really interesting: despite everything she’d built, Emma spent a long time downplaying her creativity and what she’d achieved. We talk about learning to take your creativity seriously, the assumptions we make about what ‘hard work’ is supposed to look like, and why doing something you enjoy doesn’t make it any less valuable. And Emma is really honest about the harder parts too – building a business alongside motherhood, having no maternity leave and struggling with postnatal depression. What you’ll learn in this episode: How Emma turned a problem she wanted to solve for herself into a product business

Helen actually pitched herself to be a guest on this podcast – which, as you’ll discover in this episode, is very Helen. I’ve known Helen for a few years and have loved following the evolution of her business as an illustrator. And one of the things she’s got really good at is putting herself out there, asking for opportunities and not letting the fear of rejection stop her. She even set herself a challenge to collect 100 rejections, which completely changed the way she thinks about hearing no. Her business has evolved a lot too. She started out thinking she’d sell cards and gifts, but over the last five years she’s tried lots of different things and gradually worked out what she enjoys, what she’s good at and what makes money. Live illustration came from trying something and seeing what happened, and it’s now a big part of her business. In this episode, we talk about experimenting until you find what works for you, getting more comfortable with rejection and having the confidence to ask for the opportunities you want. We also get into pricing creative work, why fewer, better-paying clients have given Helen more space, and how she protects her creativity now that being creative is also her job – including taking herself on regular creative dates. What you’ll learn in this episode: How getting more comfortable with rejection can make it easier to put yourself and your work out there

I worked with Rich on his brand a few years ago, and since then I’ve loved seeing him really grow into his confidence and identity as a creative business owner. When Rich first went freelance as a graphic designer, he thought he’d found the freedom he wanted. But in reality, he still felt like he was working for somebody else. Then he realised he’d love to be a sign painter. Over the next few years, Rich gradually changed his business so that sign painting now makes up around half of his work, alongside graphic design. And along the way, he’s had to unlearn a lot of the rules he brought with him from employment and stop worrying so much about what he should call himself or how other people might perceive what he does. In this episode, we talk about giving yourself permission to build a creative business around the way you actually want to work, being the boss you want to work for and making space for the different creative things you enjoy. We also get into Rich’s move into sign painting, why working with his hands helped him reconnect with his creativity, and why you don’t necessarily have to choose one thing to be known for.