Siobhan's Career Change Story: From project management to entrepreneurship


Siobhan is an Escape School Alum, ex-property project manager, Founder of ToGetHer Further, and author of Finding My Way: Out of the darkness, into the light. With a love of deeper conversations and truly connecting with people, and a hate of small-talk, selling herself, and anything that feels false, Siobhan felt constantly anxious and overwhelmed by her career in high-end property development. But she managed to escape and is now championing women helping women and has just published her first book. Here she shares more about her career change…
Describe your life before you ‘escaped’? What were you doing professionally before you ‘escaped’?
I was a project manager on a high-end property development in London. I was struggling being a woman in a male-dominated environment, so I set up a community called ToGetHer Further, for women to help each other with their challenges at work.
How were you feeling at this point in time?

I was working long days under a lot of stress and pressure, feeling generally overwhelmed and constantly anxious. I was keen to build ToGetHer Further into a business but was struggling with clarity around how to actually commercialise it.
What main blockers were stopping you from making a change before joining a Tribe?
Before I joined Escape, I thought my main blocker was isolation – I had decided to go part-time and was afraid that I would struggle to be alone at home while I tried to work on developing ToGetHer Further. I was also afraid of money issues – reduced income, and then planning to leave work altogether when I still didn’t quite know how I was going to turn it into a business.
When was the moment you decided to make a change & join The Escape Tribe?
I had already decided I needed to go part-time and start making moves towards leaving my job before I signed up for Escape – I knew I would never be able to fully understand and live my truth while stuck in the corporate world. The moment came for me when I was sitting in a meeting at work and I was being given yet more responsibility and additional projects, and every fibre of my being was screaming “No, enough!”. Deciding to join Escape came later, as I faced the prospect of not being in the office full-time, and was nervous about being alone and potentially becoming isolated.
What did the Escape mean to you?
I hadn’t realised how terrified I was of what people thought of me before I joined the Escape Tribe, or how afraid I was of leaving my comfort zone! Edge challenges, and gradually practicing being more visible, helped me to see just how much I could achieve – and quickly!
How did you start to overcome your career-change blockers?
The two questions I asked myself regularly – and still ask myself today – are “what’s the teeniest tiniest thing I can do today to help me get closer to where I want to be?” and “what would I do if I wasn’t afraid of what people thought of me?” I found that I was getting overwhelmed by anticipating huge changes, rather than simply putting one foot in front of the other and then realising I was running! And now whenever I find myself cringing, or wanting to avoid something because I’m afraid of what people will think, that’s automatically an Edge Challenge to overcome!
From your Escape experience, which learning has served you most going forwards?
Most definitely the concept of Edge Challenges! Before I learned about them I used to leap from the Comfort Zone to the Panic Zone and back again, and wonder why I didn’t feel any braver! Now I use the smallest steps possible to stretch and build that muscle, and I’ve grown so much over the last year as a result.
What have you been up to since finishing the programme?
Since finishing the Tribe, I left the corporate world a few months’ later, signed up to do a Post-Graduate Certificate in Coaching at Birkbeck, University of London (after I ‘hustled’ a meeting with the course leader!), I ran events for ToGetHer Further (testing the ‘lean start-up’ concept), I signed up to work with a Business Coach (knowing the investment after the benefits of Escape), self-published my own book (serious Edge Challenge /Life goal / Done is better than perfect!!), gave my first public talk (sharing my story at the Escape Career Change Accelerator!), and reached out and got Harriet Minter and Rebecca Holman to endorse my book (hustle, hustle, hustle!), and I’ve just taken on my very first practice Coaching clients (including some people from the Accelerator!)!
What are you doing now? What does your day-to-day look like right now?
I mainly work from home, in a beautiful office space I’ve made for myself in our spare room, but I also work from Blooms London 2 days a week, which is gorgeous space designed for female founders – it has a soft, feminine energy, perfect for developing ToGetHer Further and running our events there. I spend my days either creating content for the ToGetHer Further community – from articles to blog posts, and facilitating discussion on the group itself – or working with my practice Coaching clients, or working on my book, which I’m currently preparing for paperback release any day now. I have this lovely balance of getting to have space to myself and also getting to meet up with really interesting, inspiring people at Blooms, which helps me to see just how much I can achieve myself.
How did you handle your finances to make your shift possible?
I was very fortunate that I had been working as a freelance consultant for quite a few years, so I had built up a good safety net and knew I was planning to take a full year out to build my business. For anyone who does not have that privilege, working part-time or consulting on the side would have to be the way to go.
What has been your biggest challenge since joining The Escape Tribe?
The biggest challenge has always been money for me – I struggle to value my efforts outside of the corporate world because I’m enjoying what I’m doing so much, and because I’m so passionate about helping people, but I know I need to value my time and charge for it accordingly!
How are you dealing with this challenge?
My business coach, Helena (, has been awesome for keeping me focused and not letting me get distracted with yet another lovely idea that won’t make me money! Now that we’re clear that it’s my Coaching services that will form the basis of ToGetHer Further as a business I need to be brave and start charging for my time. I’ve been working on my ‘money mindset’ with Helena’s help and I know I need to start applying some Edge Challenges here to help me build up to truly valuing myself and my time.
How are you feeling about yourself now?
I’m so proud of everything I’ve achieved so far – it’s been such an exciting year, from publishing the book to growing ToGetHer Further to 950 members, and all the challenges ahead for me to face! I know I’ve learned so much, and grown so much in myself over the last year, and I love how I spend my days. I feel really fortunate that I get to wake up every day and spend my time doing exactly what I want to do – and I know the only obstacle that might prevent me doing that for the rest of my life is me…
Where can we find your work?
My book is available now on Amazon Kindle, with paperback to follow very soon, you can also download a free sample via my website, and if you want to connect with me or the ToGetHer Further community, everything you need to know is at, or follow our social pages: Twitter, Facebook, Instagram. If you’d like to chat drop me an email at!

Siobhan completed Escape’s career change course in April 2017. To join her in making a career change and be part of an exciting community, learn more here.

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