Christine Cordon has had a varied and unusual career. The first in her family to go to uni, she didn’t do a training contract but was an associate at Ashurst and has worked in America and in-house at the big banks. Now she’s the top lawyer at the holiday start-up Secret Escapes.

You don’t come from a privileged background – how did you get into law?

I was the first in my family to go to university and one of the first from my school to go to Oxbridge. I felt I was a bit of a trailblazer – the irony was I was being a trailblazer by making the most conservative decisions possible!

I did jurisprudence at Oxford, then I did the bar course and wanted to be a commercial chancery barrister. I went on mini-pupillages at all the best chambers, sat with judges in the Court of Appeal, utilised all the Oxford contacts and played it safe. I found that going to the most ‘prestigious’ places simply didn’t fit with me and my personality. After doing lots of mini-pupillages I found myself working as a paralegal at Ashurst to pay the bills.

I never thought I would end up doing financial services in the City. I started off doing temp paralegal work – just the typical admin stuff – but when Ashurst discovered I had an Oxford law degree they started giving me documents to draft.

It turned out I had a knack for the structured products work, which was fairly commoditised but also quite technical. So I progressed from a temp to permanent staff and then to legal manager. I had done the BVC and had two years of working that was equivalent to a training contract, and loads of contentious experience so I wrote to the Law Society and I qualified without doing a training contract.

What was your time at Ashurst like?

I started at Ashurst at the tail end of 2006 and qualified in 2009, having been fee earning since 2007, so by 2010 Ashurst were treating me more or less as a 3PQE. I was working on a range of stuff for JP Morgan, which was the firm’s biggest client, but also Goldman Sachs, Citigroup and Credit Suisse. I got bored doing structured products, so I worked in other areas as well to get a wider range.

Then in 2010 Ashurst opened an office in New York. I was getting itchy feet and I think they were worried I might be poached by a client, so they sent me to New York as a London ambassador. It was more of a business development-focused secondment, introducing the lawyers to banker clients in New York. By this time I had done secondments at JP Morgan and Credit Suisse, which is why I had those contacts. I also did some work with the lawyers in the US, retraining them in structured products. Again, it was quite an unusual situation to be a junior associate teaching senior lawyers how to do something.

When I came back I didn’t want to churn out the same old documents so I went on secondment for another six months at Goldman Sachs and when I came back I think by that point I had gone feral. I was only back at Ashurst for a few months when Credit Suisse offered me a job.

At Credit Suisse I was in the legal team responsible for structured products. It was less transactional and more of a governance role advising on the direction regulation was going in and what they could do with the products.

Then after six months Erica Handling, who had been at Ashurst but had taken a GC role at Barclays Investment Bank, gave me a call and asked me to come and work for her team. I jumped at the opportunity. It was a platform to be involved at a strategic level, not just advising but actually looking at “where is Barclays Investment Bank going?” I was there two years and then I was approached by Goldman Sachs, who were looking for someone to manage a structuring team in their front office.

In fact, you’ve gone through plenty of jobs and employers in quite a short career. There are always conflicting views about how long you should stay in one place…

Having a lot of switches in your career is okay – you are allowed to feel your way through your career. And no decision is forever. The idea that you pick a traditional law firm and stay there until you make partner is quite anachronistic nowadays.

So I jumped around a lot but learned a hell of a lot and gained huge amounts of confidence.

You’ve worked in law firms and in banks – what are the differences between them?

Law firms are very conservative when it comes to risk. In private practice, it’s intense but it’s slower-paced and you use that time to think. You get an office.

And you are the asset, the revenue generator. It’s a culture shock to move to a bank and realise you are a control function – there is the bias that as a lawyer you are a deal killer.

You have got to think on your feet in a bank, especially as a lawyer. You will find yourself in meetings being asked to give advice there and then, which will be acted on 30 seconds thereafter. So it is advising on a hunch, which requires a lot of confidence.

You learn that the most valuable commodity in that environment is credibility: you are constantly in meetings with senior people, and you have to be very considered in the soft skills – how you carry yourself and delivering advice in a clear, confident manner – almost psychological tactics.

I enjoyed the no-nonsense, ‘get it done’, focus on the big picture environment of banks. On the other side, the culture was all about your personal brand, and there is a lot of hierarchy and politicking and internal competitive tension.

So you left to go to a start-up… was that another big culture change?

I was at Goldman Sachs and getting my feet under the table and starting to carve my path but aware something wasn’t quite right, and it was really intense in terms of hours.

Then a friend approached me for advice – he was considering whether to get a legal counsel, and just through conversation it was decided I would be good for the role. So I made the jump to [children’s debit card business] Osper, which really was as ‘start-up’ as it comes.

In complete contrast to a bank, at a start-up the big picture is ‘Are we going to run out of money in six months time?’ I found myself doing all sorts of things – I was pitching to investors at times and it was almost a COO role at moments, where I was managing the workforce and looking at hiring and retention. I was there for 18 months and I still help Osper out quite a lot. You do get quite emotionally involved.

And now you’re at Secret Escapes…

It’s really fun and challenging. You think because it’s a start-up you’re going to go somewhere really laid back, and it is the polar opposite of a traditional law firm where you are shackled to your desk. But it is intense.

The key difference as a GC in a start-up is that you have finite resources – you can’t do everything. It is definitely ‘back foot’ rather than ‘front foot’ lawyering, particularly when you are the first lawyer through the door.

With a company like Secret Escapes, which has grown internationally and in a haphazard fashion, you find a lot of unknown legal risk. You keep turning over rocks and finding creepie-crawlies under them. You don’t have the resources to fix them all, so you have to be hugely big-picture in your thinking: ‘Is anyone going to go to jail for this? If so, okay let’s fix it.’ There has to be a lot of prioritisation.

It’s not a stable business in that it is constantly looking at new jurisdictions and products, so the ground is constantly shifting, So as a lawyer you see IP, M&A, disputes – all the same basic legal work as in any other company, but the skills set is very different. There is no list of projects that you want to achieve in the coming year, where you delegate them to others, then check in on a weekly or monthly basis and slowly tick them off. It’s ‘What’s our biggest risk this week and how do we deal with it?’

That’s really exciting, but that healthy appetite for risk can be very stressful for juniors. If I hadn’t jumped around in my career I’d probably be having a minor nervous breakdown in this job. But having been in banks going through the credit crisis has given me those skills to deal with uncertainty and risk.

What advice would you have for aspiring lawyers?

The first thing – it sounds really trite, but it’s a cliché for a reason – is ‘nothing ventured, nothing gained’. It’s so easy to think, ‘I’m never even going to get in to Oxbridge, I’m never going to get into that job, I’m not going to apply.’

I wasn’t top of my class, I was just a super-hard worker. I was academic through effort rather than excellence. If I got a knockback, that was okay. I have never been put off by the prospect of failure. I applied for lots of stuff that I thought I would never get, and I got turned down a lot, but I also got some offers.

The other thing I would say is, don’t worry too much about the future. Especially when it comes to aspiring lawyers, you know a lot of people who have a five-year plan.

I had that. I took myself so seriously at 18. I had it all mapped out – when I would do pupillage and at what chambers. I took this plan so seriously when I inevitably got to the stage when things went awry – because that’s just what happens – it’s hugely destabilising. You have to reconsider everything you hold true, and I started to realise the plan was nonsense.

People change as they are growing up too – what’s important to you at 18 isn’t what’s important to you at 25, or 35. And make decisions based on what you enjoy rather than on what you thinks looks the best on your CV.

One thing that is consistent with almost every lawyer I know is that none of us put ‘having fun’ at the top of our list of things we look for in work – which is ironic because lawyers spend a huge chunk of their lives at work. I’ve yet to meet a lawyer who doesn’t check their emails on weekends.

Trying to achieve work-life balance is one approach but since most lawyers are incredibly bad at doing that, the other alternative is to have more fun at work. All of the rest is nonsense – forget salary, job prospects. It’s a sadistic thing – lawyers know they are going to work every hour God sends but they refuse to make it enjoyable for themselves.

One of my first mentors gave me some advice that stuck with me for years: “The definition of a job is someone paying you to do something. By definition it’s something they don’t want to do themselves – so any job you have is something someone else can’t be bothered with.” It took me 10 years to work my way out of that mindset.

The other thing I’d say is, gone are the days where people look for the best redbrick universities and best magic circle law firms and the best academics on your CV. I think those prejudices and biases are starting to dissipate. In the world of start-ups and disruption, commerciality, smartness, and being able to hit the ground running are the important things.

Law less ordinary | Acting for start-up companies