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Pick Yourself UK Small Business Entrepreneur of the Year awards and platform for self-starters in the UK


PickYourself UK Small Business Entrepreneur of the Year entries

Jen Eastwood | Starting a business after hitting rock-bottom



This week’s #selfstarterstory features Jen Eastwood, Founder of Rock Rose Digital.

Pick Yourself UK caught up with Jen to learn more about her entrepreneurial journey…

January 2018. Bank balance subzero. Mental health even worse. I was made redundant the week before Christmas, no warning or apology.

I lived on my own, 40 minutes from my nearest family and friends. In an icy cold flat with a top-up meter, often having to decide between food or electricity. Friends sneakily drip- feeding money into my account so that the cat didn’t starve. My 30th looming - skint, unemployed, single, feeling utterly worthless, regularly contemplating the idea of not being here to see in my birthday. I was at rock bottom.

Aside from questioning my existence, the idea of working for someone else again made me want to hurl. The potential commitment and pressure of a full time role, on my mental health, sent me into a spiral of anxiety. But, a part-time job wouldn’t have brought in enough money to keep my lonely flat, and also wouldn’t have been free of the pressure to be ‘OK’ and functional for the rota.

Doing my own thing and working for myself would be crazy, right? Creating my own business would be too much pressure, I wasn’t experienced enough in my industry and I definitely wasn’t business-minded. I’d never considered working for myself before; attempting it now with my brain in the biggest funk of my life would tip me over the edge.

At least, that’s what my inner critic kept telling me. But I didn’t listen. I blocked out the noise enough to do bits of work and keep my furry friend from going hungry. I just needed to do odd bits, get some money in to keep me afloat until I could work out what I actually wanted to do next. I never anticipated doing it for the long-term.

Until I landed my first client.

I did the work, got my invoice paid; things felt good. So I got another client, and the same again and life started to not seem so bad any more. Now, I’m 14 months in to running my own business and I have worked with over 30 businesses, ranging from local sole traders, to a national leisure franchise and an international author launching her first book. I’ve collaborated on a national campaign with the Royal Society for Public Health drawing awareness to our social media usage, I’ve won Jacqueline Gold CBE’s coveted #WOW award and been interviewed by industry publishers for my thoughts and experiences.

Sure, it’s not gone completely smoothly. I’ve made mistakes. I’ve had things go wrong. I’ve had someone threaten me with legal action for THEM not paying MY invoice. (yes, REALLY!). There’s been tears and thoughts of quitting and getting a “normal” job.

It has not been easy, and I know I’ll come across other hurdles and challenges in the future. But honestly, it’s actually not been as completely disastrous as I expected and now I wouldn’t change it for the world!

By about the 6 month mark, after a run of particularly challenging months, I actually started considering myself as a proper business woman. It’s through the adversity early on that I learned so much about my business; what it stands for, how I want it to operate, what kind of clients I want to work with and how I am as a business owner - all knowledge I’m extremely grateful for! I’m lucky that I’m now able to pick and choose who I work with, unlike the early days of saying yes to anything just to keep the money coming in. I’ve learnt the beauty of setting boundaries and the power of no. These are strengths I have NEVER had in my life!

What about before digital? I left a 12 year career within hospitality in 2015, after working my way up to managing a Michelin star restaurant - my dream role. On my first day of this ‘dream job’ I was assaulted by a colleague in my hotel room. The worst way to leave an industry I’d given most of my life to. I genuinely grieved after deciding to walk away.

For years I lacked any real purpose or drive, genuinely not knowing what to do with my life or skills. A lot of recruiters not looking past my job titles towards my invaluable experience and transferable skills. My only options for work being crappy filler jobs only furthering my assurance of what I didn’t want to do be doing.

Up until this point, my working career had always been customer-facing, and service orientated. Hospitality particularly giving me sixth sense for consumer needs and an intuitive, but approachable, tone of voice - all skills that are crucial elements of my marketing arsenal. I’d dabbled in the digital side of the boutique catering brands I’d worked in and found it came naturally, so when an opportunity appeared for a role within a small digital agency I jumped to it!

I could be sorry how it ended, but I don’t think I would have every considered being self-employed otherwise.

I now have complete control and autonomy over my working days, my mental health has never been more stable and I have genuinely never been happier. As well my business, I’ve set up a women’s networking and co-working community, I’m helping on various social impact projects and currently have big investment on the table for a mental health app I’m developing.

I could not be further from the Jen I was on that cold lonely January, and I am so 'effing proud! There’s still a long way to go, things I want to achieve - financial, personal, mental. But for now, I’m going to enjoy the ride and see where this crazy journey takes me.