Anna Cleland, founder of Work-Happy

Photo of Anna Cleland

Anna Cleland is the founder of Work-Happy, a platform which equips individuals to take control of their happiness at work. In our fast-paced, career-driven world, Work-Happy enables employees to undergo self-analysis, work through guided reflections and make a commitment to action to improve how they feel at work. Work-Happy also provides managers a constructive framework within which they can check-in with their employees. Despite only officially launching in March 2020, the individual accountability and agency which Work-Happy fosters has only become more relevant in light of the pandemic.

Since graduating from Oxford Brookes University with a degree in Human Resources Management, Anna has worked in Human Resources Consultancy all her life. In the early stage of her career, she worked with those who had recently been made redundant, helping them to reflect on what they really wanted out of life and a career.

Anna went on to found the consultancy firm Ixia, which she directed for about a decade. However, she began to become disheartened with the realistic impact employee engagement surveys made in companies. Not only did these ‘quick-fire’ responses tend to produce only polarised responses from employees, but the results typically only acted as aggregated data for company meetings. Without the unique reflection and coaching each employee requires, Anna became convinced that these wide-scale surveys made little difference to individuals’ happiness.

Over the years, she realised she had a choice – she could either collude with this ‘data game’ system, comfortably earning without making the impact she wanted to, or she could take a risk and create something that would genuinely positively affect people’s lives. Work-Happy is the product of that risk.

What is your background? What made you decide to become an entrepreneur?
Work-Happy Logo

Even when I was in school, taking part in Young Enterprise, I challenged everything. I was never going to follow the standard path and do the same as everyone else. That trait of challenging the status quo meant entrepreneurship was slightly inevitable for me!

I have always held the belief that anything should be up for debate and could be changed and if it wasn’t doing what it should be doing or delivering effectively then there was probably a better way to do it.

Over time I found I was working in an industry that wasn’t delivering the outcomes it claimed to so I slowly grew disillusioned with the effectiveness of HR employee engagement surveys in making a difference to employees’ happiness. After years in the industry, gradually all the pieces of the jigsaw fell into place and I decided to take test out the concept of Work-Happy, turning everything on it’s head which could have a deeper effect on people’s work enjoyment.

How has the pandemic changed your business and the work you’ve been doing?
The pandemic unfortunately put us on the back-foot in many ways as we had only just launched in March! On the one hand, the pandemic has pushed wellbeing and the work-life balance into the spotlight. The discussion around wellbeing is often limited to mental and physical health. While incredibly important, these more traditional conversations are ultimately ‘in the moment’ and short term. They don’t ask how work is impacting you or whether this way of life is sustainable. I believe that Work-Happy asks these long-term questions and addresses more fundamental wellbeing concerns. As we enter the new year and the longer consequences of the pandemic are felt, the problems that Work-Happy uniquely addresses will become more apparent and pressing for individuals.

What is your definition of entrepreneurship?
Entrepreneurship is the drive to challenge the status quo. It’s the voice that says, ‘just because something has always been done this way, it doesn’t mean that there isn’t a better way’. There are plenty of entrepreneurial skills you can develop, but the curiosity and determination to explore those ‘what ifs’ is something that can’t be taught.

How and when did you know your idea was good enough to develop it?
When the final jigsaw piece slotted into place and I realised that there was a commercially viable and marketable concept. I tested this out with a number of colleagues, clients and HR industry professionals and they confirmed it would be a fantastic solution.

What would you say are the top 3 skills that needed to be a successful entrepreneur? Why?
Firstly, resilience. As an entrepreneur, you experience lots and lots of knock backs and challenges. You have to keep picking yourself back up and cracking on. It’s hard, but the ability to ride out those lows and put in the energy to create the highs is imperative. You get many more lows than you do highs!

Secondly, vision. An entrepreneur needs the ability to see the future, seeing how things could be in the future, ahead of what exists in the industry now. You need that ability to see a brighter future because it’s what will drive you when you experience setbacks and challenges.

Thirdly, adaptability. An entrepreneur needs to find ways of dealing with uncertainty and ambiguity. 2020 has shown how much is outside of our control. Don’t overthink things – learn to be comfortable with the unpredictable and adapt quickly.

What is your favourite part of being an entrepreneur?
Creativity. I love the two sides of business, both the analytical rigor of data and strategy, as well as the creativity behind exploring a fresh idea. You have to blend both together to get your business off the ground, but I think that ultimately the passion for creating something new is the most exciting part. When you get stuck in short-term details, it’s the creativity and desire to create change that keeps me going.

What individual, company or organization inspires you most? Why?
Someone like James Dyson or Richard Branson because they failed so many times. I find the most inspiring people to be the ones who, when it all went wrong, overcame adversity and tried again and again. They held onto their dream and said it was worth fighting for.

If you had 5 minutes with the above individual/ company/organization, what would you want to ask or discuss?
I’d ask what kept them fighting! Why and how did they keep picking themselves off the floor when it would have been so much easier to give up?

What has been your most satisfying or successful moment in business?
I think it’s still to come as Work-Happy is at such an early stage. I’m still striving for it. So far, the most encouraging, affirming moments have been when senior people in the HR world have seen my work and said, ‘you are really onto something’ and that people love the product we’ve created.

What would you say have been some of your mistakes, failures or lessons learned as an entrepreneur?
There have been two. First, when I was just starting out, I hadn’t realised how difficult it is to be a solo founder, specifically a solo female founder. I should have tried to find others who were passionate about this issue and who wanted to bring the vision alive with me. It’s still possible to do it on your own but being part of a group would have made certain challenges easier to overcome.

Second, I wish I’d thought more about sales and adoption in the early days, rather than just focusing on the development of the product. While I don’t know what I would have specifically done differently, I regret not dedicating more time to thinking about it.

How have you funded your ideas?
Work-Happy was initially self-funded, myself and others worked on it for free. As the potential grew we raised money through friends and family and a number of Angel Investors. I’ve learned that as an entrepreneur you have to be willing to ask people for money. This can be difficult, especially for women who can often feel more sensitive or responsible when borrowing money than their male counterparts. However, it’s something you just need to get used to.

Are there any sector-specific awards/grants/competitions that have helped you?
Unfortunately, Human Resources grants don’t really exist in Oxfordshire, so most of my support comes from the South-East.

What is good about being an entrepreneur in Oxfordshire? Bad?
Oxfordshire is very heavily influenced by the Bioscience and Healthcare start ups, so it can be hard when you are in a social science sector. There are a number of opportunities specifically for University of Oxford alumnus or spin-offs, which limits the investment and accelerator opportunities if you aren’t from the University.

If a new entrepreneur or startup came to you looking for entrepreneurship resources, where would you send them?
Tech Nation is a brilliant organization which offers amazing support to tech start ups and their founders. Also, OION (Oxford Investment Opportunity Network) is another great network that connects founders to potential investors.

Have you faced any challenges as a woman entrepreneur? If so, how have you overcome them?
The challenges of your business are constantly fermenting in your brain. No one else loses sleep for your business in the same way as the founder. You can’t just switch it off. As a result, one of the biggest challenges I’ve faced is being a mum, a wife and an entrepreneur. In many ways, your business can be like a second baby that you’re growing – and they both need all your attention! Sometimes it can be really hard to clear the mental space to make quality time with your family and not let the stress seep into how I talk to my family. Of course, this can also be difficult for men as well; however, it has been a particular challenge for me as the more nurturing parent.

What resources would you recommend for other women?
I haven’t found any specific ones, but the most important thing I would recommend is to find people, men and women, who really believe in what you’re trying to achieve. When you struggle, anchor yourself back to these people. They are the ones who will champion you to the world when you don’t think you can champion yourself.

How could institutions such as the University of Oxford better support women entrepreneurs?
Despite living around Oxford since I was a student at Oxford Brookes, I have never really connected with the University of Oxford. These institutions seem to be very alumni centric. However, I think that the more diverse people you can bring together, the better the discussion and product you will get. I would love institutions like the University of Oxford to provide more opportunities for alumni and non-alumni to work together in teams of founders and various University programmes.

Do you have any advice specifically for other women who want to be entrepreneurs?
Do not let the fear of failure stop you. This is really hard for everyone but I think women worry more about letting other people down than men probably do. Talking about gender differences is always tough because I don’t believe in stereotyping; however, we know from research that women tend to ‘feel’ more than their male counterparts who ‘think’ more. This potentially helps male founders to rationalise setbacks more easily whereas women are more likely to worry about the impact on others of their success and progress. Even so, I passionately believe that women can bring such a different approach and solutions to the market which is essential for the development of our world. So, no matter what, feel the fear and do it anyway!

Any last words of advice?
Really think twice before you go it alone. When you’re starting out, you are bold and brave and think you can conquer the world. The temptation may be to just get on and build it on your own, but when things get hard and everything ultimately comes down to you as the founder, it can get very lonely. Find people who want to share the journey and the responsibilities equally with you.