Helping Artists Breathe Again: Jennie Cashman on Building Sustainable Creative Careers

Mike Flynn: Tell us about your background in music, your career path, and how it relates to what you do now?

Jennie Cashman: I’ve been working in grassroots music since 2009, which is when I met my late husband, Abram Wilson, an acclaimed jazz trumpeter from New Orleans. I started helping him with a bit of admin, which quickly grew into looking after every area of his career, from finances to bookings.

When he passed away in June 2012, I needed something to pour my grief into, and that’s how the Abram Wilson charity was born. Over the next decade, I built it from an idea into a multi six-figure organisation that inspires, connects, and opens doors to the music industry so that minoritised young talent has an equal chance to realise their creative potential. That experience is what led me to the work I do now.

MF: You clearly understand and empathise with the people you support. Where does that come from?

JC: I spent years convinced I was going to be a professional actor, but in the end I wasn’t willing to take the risk. Instead, I found myself working with organisations that supported young creatives: British Youth Music Theatre, Tomorrow’s Warriors, the National Centre for Circus Arts, and eventually, the Abram Wilson charity.

[US writer and theorist] Joseph Campbell famously said, “The cave you fear to enter holds the treasure you seek.” He wasn’t wrong. I feared the uncertainty that comes with a freelance career, but it found me anyway, first through Abram, and then through building the charity from scratch. So, when my clients come to me with similar fears, I get it. I’ve been there too.

MF: What would you say to someone unsure about some form of coaching?

JC: The best way I’ve heard it put is by one of my mentors Townsend Wardlaw: no one wants coaching, they want their problems solved and their deepest desires realised.

The thing is, most people don’t know what problem they need solving or how to create something more ambitious for themselves until they start talking to someone who really listens. That doesn’t happen often, because most of us are used to conversations where everyone’s just waiting for their turn to speak.

But when someone experienced truly listens and asks the right questions, you start to see your situation differently. That’s when new possibilities open up and change can begin. Still, change is scary, and many people convince themselves they can do it alone. That’s possible, but it’s harder, and it takes longer.

Working with someone one to one who can act as a trusted guide is a big commitment, but for those who do it, the results can be extraordinary.

MF: You also use LEGO in your work—which might sound surprising. Can you explain how and why?

JC: Absolutely! LEGO® Serious Play® (LSP) is a hands-on method that uses LEGO bricks to unlock creativity, improve communication, and work through complex ideas.

There’s growing evidence that intelligent species play to support brain development. As humans, our brains continue to develop throughout our lives, so the more we play, the more adaptable we become. But we can’t play if we’re stuck in survival mode, which a lot of us are at the moment.

So yes, I use creative approaches because they’re fun, but also because they’re powerful. They help ground people, access new ways of thinking, and they suit the kinds of creative clients I work with.

MF: It’s a difficult time right now, and making or promoting art feels harder than ever. How do you help musicians figure out what to focus on?

JC: Most of the people I work with have already built something meaningful. Their income is steady, their reputation strong, their work in demand. On paper, it’s all going well. But they’re constantly ‘on’. Everything still runs through them. They’re juggling too much, feeling stretched, and they know it’s not sustainable.

They want to grow, but not at the cost of their health or creativity. They want time and space to focus on the parts of the work that light them up, but that feels impossible right now.

My job is to help them think differently. I give them the time and space to reflect, see their challenges through a new lens, and figure out how to change their way of thinking and behaviour to move forward. It’s a process that takes time, patience, and commitment. It’s not easy, but then if it was, we’d all be doing it!

MF: You often ask questions about physical health, money, and income. How are these things connected to making a living in music?

JC: There are four key areas that I believe get overlooked when building a freelance career or creative business:

1. Your Relationship with Money
How you feel about money influences everything, from how you price your work and ask for fees to how you manage your invoices and decide what to say yes or no to.

2. Your Emotional & Physical Health
You can’t build a sustainable music career if you’re always anxious, frustrated or overwhelmed. You’ll burn out. Learning how to notice when you’re triggered and how to calm your body is essential.

3. Your Strategy
If you don’t take time to plan for the long term, you’ll say yes to everything and never get closer to the life or career you really want. But strategy only works when you’ve laid the groundwork with ingredients 1 and 2.

4. Your Network
In music - as in life - real opportunities come from real relationships. Knowing how to connect and stay connected with others is how you grow, both creatively and financially.

MF: Do you have any tips or suggestions for how to reassess your creative or personal life to make it more sustainable?

JC: If something feels off, ask yourself: ‘What’s clogging up my pipes?’

If you’re doing the same thing over and over but not seeing the results you want, there’s probably a kink somewhere in the system. Your job is to find it and address it.

Let’s say you’ve built a great career as a solo artist, but the pressure of doing it all alone is becoming too much. That might be your blockage. So the next question is: ‘What might I need to start doing to get things flowing again?’

It doesn’t have to be huge. Small changes often open the door to big shifts.

MF: Lastly could you give an example of how some of your clients have implemented some of the things they’ve brought up and then gone away and worked on?

JC: One client realised their mini-panic attacks were as a result of forcing themselves to work long hours and not take regular breaks or time off at weekends. They began by reducing their workload so they could go to the gym and spend time with their partner. Very quickly they noticed they were more motivated and had increased energy and focus.

Another client had never really thought about their relationship with money. But during our work together, they uncovered early beliefs rooted in fear and avoidance. They went from regularly staying awake at night thinking about their finances to letting go of the idea that they had to constantly worry about it just to stay afloat. This meant being able to communicate better with their partner and enjoy the life they’d built together.

Despite having built a very successful career one client still found themselves being pulled in a million different directions with no space in the day to prioritise their own work. They went from responding to everyone else’s requests to protecting their time each morning to practice their instrument, exercise and meditate. This resulted in improved communication and better boundaries with their team.

For more info and to take Jennie’s career quiz visit: www.jenniecashman.com/quiz