Canada

The View From Up North: Practicing Law In An Ocean Paradise

What's it like to practice law in the Cayman Islands? Tranquil.

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I had a lovely vacation on a cruise ship last week. I won’t mention the cruise line, but the boat was filled with “characters” and the elevators played some of the most beloved movie songs of all time. Anyway, the weather was gorgeous, the food was super, and my family had a wonderful time. But, don’t be hatin’, because I came home to frigid temperatures and a foot of snow in my driveway. It all evens out…

If you follow my column, you know I am writing a series about lawyers who are doing different or interesting things with their lives. My cruise ship happened to stop in the Cayman Islands. That meant I got to have lunch with my friend, David Dinner. David is an ex-pat Canadian who has been living and working in Cayman since 2008. He recently opened his own law firm, Dinner Martin.

Cayman is blanketed by blue skies and enveloped by the warm and inviting Caribbean Sea. The country enjoys a very high standard of living with modern housing and great restaurants. There is no corporate or income tax. It has a large, vibrant legal bar that helps tax evaders international businesses manage their affairs. Imagine charging Seven Sister billing rates, working hard (but not crazy hard), and paying no income tax? There are a lot of wealthy lawyers kicking around Cayman.

Prominent firms that you may have heard of include Maples and Calder, Appleby, and Conyers Dill & Pearman (home to very friendly Canadian Rick Finlay).

As a public service for those of you staring out your window at snowdrifts and dreaming of something better, here is my slightly edited dialogue with David about living and working in Cayman Islands.

Steve M. Dykstra: What were you doing in Canada before you left for Cayman Islands?

David Dinner: I was working as a litigation associate in an insurance defense boutique.

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SMD: Why did you pack up and go to Cayman?

DD: At the time I was dating a woman who had recently gotten a job at one of the governmental authorities in Cayman. I came for a visit over Christmas in 2007 and her recruiter got wind of the fact that I was a lawyer. He asked me to bring a suit and he would see if he could set up some interviews, which was difficult considering how everything in Cayman grinds to a halt during Christmas. Despite this, he managed to arrange two interviews and I was offered positions with both firms. At first I was not particularly interested in moving to Cayman and leaving my predictable workaday life in Toronto, steadily marching lock-step towards partnership. I went home after that visit having turned down one of the offers and postponed the other. It took about a month of being back home and things just seemed different. My girlfriend and I were training for Ironman Lake Placid (my first) and it was so lonely to be doing it by myself in the dead of winter, in darkness, while she was training in the beauty and warmth of Cayman. In early February I contacted the second firm, negotiated my salary, etc., and looked forward to starting anew in a new country.

SMD: How hard was it to find a position?

DD: If you’re not from a Magic Circle firm in London or a sexy set of barristers, preferably London-based, it can be a struggle, especially with the big firms. The mid-tier firms are a little more flexible, but there are fewer positions available. I was lucky in that I found a firm that had a lot of personal injury work that they needed help with and my experience fit the bill. It wasn’t until after I moved down here and got to know the market that I realized just how serendipitous it was for me to find my position. Truly a case of being in the right place at the right time.

SMD: When you first arrived on the Island what did you find most interesting?

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DD: Interesting? Hmmmm. The people are the most interesting part of living here. Everyone is connected in some way, and usually a couple of phone calls can sort out all but the most intractable of problems. I’ve been lucky to be brought into their lives and their families and I hope they feel the same about me.

SMD: Why did you start your own firm?

DD: Although it’s always been a dream of mine, I didn’t have much of a choice, really. The firm I was working for had a nasty partnership dispute and a number of attorneys left en masse. Although invited to join them, I decided against it and my partner, Randall Martin, and I began joking about, and later planning for, our own firm.

SMD: Does owning your own firm mean you’re never leaving Cayman?

DD: Pretty much. This is home now and I must admit I miss it whenever I leave. I have a house on the water and two dogs, lots of friends, and no desire to return to Toronto. Life there was such a struggle; it just seemed like you couldn’t get in your car and spend anything less than a half an hour in traffic. Rush hour here lasts about 30 minutes, and only adds 5 minutes to your trip! The difference is stark and I feel so much less anxious here than back there.

SMD: What is it like living in Cayman?

DD: Well, some would describe it as boring, others would say it is serene, but I would say it is more tranquil. God, I must be getting old!

SMD: Do you use sunscreen all the time? What SPF?

DD: I should use sunscreen, but typically don’t unless I’m going out for more than an hour. It sounds horrible to admit it, but it’s true. I hope my mother isn’t reading this… When I do use sunscreen, I go for spray-on SPF 30.

SMD: What do you do in your spare time?

DD: I like to do triathlons, so most of my spare time is taken up with swimming, cycling, and running. Aside from that, I like to putter around the house.

SMD: Do you get “rock fever”?

DD: I used to. I used to try to get off the island once a month, either for work or pleasure. But as time went on, that feeling faded and I’ve only been off-island twice in the last year, and one of those trips was to compete in Ironman Cozumel.

SMD: How hot is it in the summer?

DD: Surprisingly, not too hot. There is relatively little temperature swing from winter to summer, maybe 10 degrees Fahrenheit. So it gets up to around 90 degrees in the summer, sometimes 100, but it’s still livable.

SMD: What’s the best part of living in Cayman?

DD: The size. It’s so small you can be anywhere within a few minutes. There’s a special level of Dante’s Inferno where people just drive around in their cars for eternity. I can’t do it. I don’t want to spend my life in my vehicle.

SMD: How expensive is it to live?

DD: It ain’t cheap. On average, everything is 25% more than it would be back home. The worst part is that some items can be 50-100% more expensive, without rhyme or reason. Try shaving cream for example. If it’s $4 back home, it’s $10 here. Why, you ask? No idea…

SMD: Is there anything you miss about Canada (don’t say snow)?

DD: I miss my friends and golfing in the spring and fall. I miss being able to drive for a few hours and be in the middle of a forest or beside a lake.

SMD: What do you recommend to people who want to practice law in an offshore jurisdiction?

DD: Make sure you’re cut out for it. If you think you’re coming here like a bull in a china shop, upsetting apple carts and forcing your will onto people, forget it. This place is bigger than you. Also, if you come here, be sure you have a hobby (aside from drinking) or a sport to occupy your spare time. And if you come with a family, make sure your spouse is cut out for it too!

That’s the View from Up North. Have a warm week.

Steve Dykstra is a Canadian-trained lawyer and legal recruiter. He is the President of Keybridge Legal Recruiting, a boutique recruitment firm that places lawyers in law firms and in-house roles throughout North America. You can contact Steve at [email protected]. You can also read his blog at stevendykstra.wordpress.com, follow him on Twitter (@IMRecruitR), or connect on LinkedIn (ca.linkedin.com/in/stevedykstra/).

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