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The flexible working entrepreneur: An interview with Dana Denis-Smith

When you grow up under communist rule in Romania, with no market economy, as Dana Denis-Smith did, you don’t expect to become an entrepreneur – the concept doesn’t exist. However, the experience did impart some useful lessons. “It taught me resilience and gave me a total lack of fear of failure, which has been very valuable,” she says. “I don’t have, like some people do, a constant fear of losing status because I’ve been in a situation where you have no choice and no freedom, and that’s when things can’t get worse. It gives you a sense of perspective. Not being scared of failure, especially in a professional sense, is an advantage because being a high achiever, validated by school achievement, and this is especially true for the legal profession, can generate a fear of failure.”

By Editorial Team. 1 July 2020.

This fearlessness has driven Dana to achieve an extraordinary amount. An entrepreneur, journalist and ex-Linklaters lawyer, she founded Obelisk Support in 2010, which is now a multi-million-pound company with nearly 2,000 lawyers on its books. The business matches City lawyers who want to work flexibly with law firms who need additional support. It has transformed the careers of many women lawyers who leave full-time work to have children and often find it difficult to return.

On setting up Obelisk, for which she has won several awards, Dana says: “I had a simple idea. It was a case of supply and demand. I’ve always had a social conscience and I want to maintain the dignity of work. When I started Obelisk, the situation with mothers returning to work was nothing like how it is now. Nobody was talking about it, apart from the Law Society, and they were looking at the profession as a whole not just City firms. It was about leveraging the capacity that goes to waste from people who want to work from home, and matching needs to clients.”

She was a journalist for several years after school before studying History, a Masters in Political Economy and then Law. She worked at Linklaters for two years before setting up her first business, Marker Global, a research agency that provided strategic business intelligence for companies looking to set up shop in emerging markets, particularly Russia and the Middle East.

In 2014, she created the ground-breaking history project, First 100 Years, which charts the journey of women in law since the Sex Disqualification (Removal) Act 1919 which allowed women to qualify as lawyers for the first time. It comprises a digital museum of 100 video stories that celebrate women’s achievements, whether that be Titanic survivor Eliza Bowerman, who was called to the Bar in 1924; Theodora Llewelyn Davies, the first woman to be admitted to Inner Temple, in 1920; or more recent pioneers such as Baroness Scotland, the first black woman appointed QC, in 1991; Barbados-born barrister and academic Sylvia Denman, who conducted the Denman Inquiry into institutional racism in the CPS in 2000; barrister and broadcaster Helena Kennedy QC; or the much admired first woman President of the Supreme Court Lady Hale. First 100 Years has also branched out into podcasts, guided walks, a book and an art exhibition and holds the annual Inspirational Women in Law Awards.

“It went well beyond what I expected, and overachieved,” says Dana. She started First 100 Years “because no one else did. I asked questions, tracked down the woman in the photo, traced a chronology of the timeline and built on it. People helped, and the professional bodies helped, by contributing stories. It became a full-time job, on top of my other full-time job.”

Despite its success, however, she still meets people who are surprised to find out about the centenary, which “makes me sad. We have to educate people about this history. This story has not travelled far enough. We need measurable milestones. It’s not enough to say something is a problem – you need to be able to measure and define how far you’ve come by looking back.”

Her advice to current law students is: “Be yourself, know what you’re good at, and always have a five-year plan. You have an incredible amount of choice in what you can do, so think ahead, but also remember that it’s okay to change your mind. Have curiosity. You don’t have to have what society says you should have. Be strategic, because that’s how you make big leaps forward. I didn’t know I could manage a business with nearly 2,000 lawyers in it. I love people and I love to see them flourish. For me, it’s about allowing other people to be great at what they can be. But always be professional, have good standards and never be sloppy – that’s the minimum.”


This article was first published in our Verdict magazine - Read Pioneers and Innovators Special, the issue #5 of Verdict magazine.