Meet our Freelancer and Entrepreneur: Jenny Stallard, an ACC accredited Coach specialising in working with entrepreneurs and freelancers.

Jenny Stallard is a coach and experienced media professional. She is an ACC accredited and trained coach, specialising in working with entrepreneurs, freelancers and the self-employed, under her platform Freelance Feels.

We caught up with her and she shares her transitioning journey from working as a media professional to becoming a freelance coach.

What led you to become a freelancer?

Becoming a coach came as a slow burn – I used to speak to (and still do!) lots of different coaches for the articles I wrote, which immersed me by default in the coaching process. Interviews were often mini coaching sessions, and I found I rather enjoyed it! I liked the idea of joining their world and of having their insight.

I also knew some friends who were training as coaches and agreed to be a client for them while they trained. That also led me to feel curious about the world of coaching and whether I might fit into it as a coach.

Do you consider yourself as an entrepreneur or a freelancer?

I find it strange to call myself an entrepreneur! But I know I am, as well as calling myself freelance. I’ve been freelance on and off for 15 years, and went ‘freelance for life’ in April 2017 after redundancy from a national newspaper.

For me, freelancing is like dating – we often date ‘self employment’, but I decided I wanted to settle down!

Can you tell us a bit more about your work?

My work and business is twofold – I’m a writer and speaker on all things freelance and entrepreneurial, as well as coaching. I specifically work with freelancers, the self-employed and what I call the freelance curious (those considering entrepreneurship).

What type of coaching do you specialise in?

I now specialise in working with freelancers and the self-employed. I can speak about being or going freelance, being a woman in business, being self-employed post-pandemic, making the leap to starting your own business, and the mental health challenges of self-employment, too.

Can you also tell bit more about Freelance Feels?

Freelance Feels (Wellbeing for humans who work for themselves) was founded in June 2019 following my own struggles with mental health and self-employed life. Initially a blog, it now has over 2800 followers on Instagram and an average download rate of 63% for the monthly newsletter. The Freelance Feels podcast just reached over 11.1k downloads since launch in Autumn 2019.

The USP for Freelance Feels is how self-employed and working from home life feels. I share my own experience as well as talking to those who are going through it too. I offer advice, but it’s less about how to do the taxes, more how putting off the taxes impacts our emotional and mental health.

What sets you apart from other coaches?

During lockdown, I retrained as a coach and qualified as ACC (Associate Certified Coach) in April 2022. ACC is very important to me, as it shows a certain level of training and practice that arguably sets me apart from other coaches. Being ACC means I’ve completed more than 100 hours of coaching and sat an ICF approved exam. Being self employed and working with the self-employed means I walk the walk that they do – I am living the freelance life and bring those ‘feels’ to the process, too. They know from the start of working together I ‘get it’. 

What does being a female freelancer (or entrepreneur) mean to you?

Moving from ‘just freelance’ to entrepreneur has brought a real sense of power for me. I feel like I am more in the space I belong in, not just talking to the coaches but being one! I love the flexibility of entrepreneur life. I’ll be honest, I love the kudos, too! There’s pros and cons but the freedom and the kudos of saying I’m self-employed are big things for me.

What challenges or obstacles have you faced as an entrepreneur or freelancer?

The challenges all link back to mental health for me – loneliness, isolation, professional ghosting (which I’ve written about for my site). The seemingly endless hustle, and the noise from others in the same space. I find it hard to detach from work, but I’ve come to realise that’s just part of being self-employed!

What has been your success story so far?

My success story so far is reaching ACC accreditation. That for me was a huge moment of ‘yes, I’m there!’. ACC means I’m accredited to the International Coaching Federation and have completed a certain level of training as well as over 100 hours of coaching. That, to me, is a big wow/yay moment I can truly celebrate.

To learn more about Jenny, her work and Freelance Feels head over to and the instagram account is @freelance_feels