Thrillable Hours: Simon Shields, Location Independent Lawyer

Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

One of the many questions I receive from lawyers and non-lawyers alike is framed around my choice to abandon the practice of law. I tend to answer conservatively – after all, there are certainly aspects of being a lawyer that I miss (like negotiating), and perhaps I will return to it one day. But the golden carrot in alternative careers for lawyers (at least given the emails I’ve received) is to practice law from somewhere more fun, enabling people to use the degree they earned, but do so outside the typical ‘rat race’ in private practice.

Simon Shields first contacted me through my site to talk about his practice and I promptly asked him if he’d be interested in a Thrillable Hours interview. He not only maintains a practice, but he does so as a location independent lawyer. His clients are regular people from Ontario, Canada who are prepared to self-litigate with his assistance. He doesn’t subcontract to other firms, but rather works in the same domains as his  prior private practice in Ontario – administrative and civil litigation. He just happens to do so from somewhere really fun – at present, Greece. Thus far, he’s also been to parts of Central and South America, across the South Pacific (Tonga, Samoa, Rarotonga), New Zealand, Tasmania and Malaysia.

Simon has also built a site called Is That Legal, with legal guides and statutory links to several of the areas of law from his practice. He also notes that there are additional factors that have led to his ability to fund his life with assistance-based legal services, namely (1) the proliferation of self-representing clients. often experienced in business or government in their own careers, (2) clients who want an alternative to hourly billing models (i.e. a flat-rate model), (3) modern payment services like Interac (Canada) or Paypal, and (4) significantly-improved internet access in many far-flung places.

With that intro, here are the regular Thrillable Hours questions!


Looking for more information about location independence? See my 7,000 word resources page about working from anywhere around the world.

What made you decide to leave private law firm practice and work as a location independent lawyer in a flexible setting? Was there a particular moment that catalyzed the decision for you?

I have always have practiced privately as a sole practitioner – I haven’t worked for a firm since articling 17 years ago. Having achieved success in my chosen field I just got bored with the office practice. For the five years before I started travelling (i.e. 2002-2007) I schemed endlessly about I how I could work portably. For a long time the financial numbers never seemed to work until one day I just said “screw it, I’m going” and over a few months did all the necessary wrapping up to do so. Of course overhead dropped to next to nothing, and Canadian income tax became a thing of the past with my non-residency. Also, no need to charge my clients HST (the Ontario value-added tax) – life became a lot simpler and cheaper.

I do remember one day when a friend of mine, another lawyer dropped in my office to chat and I quite spontaneously just popped out with “I don’t want to do this anymore”. If there was a particular moment that was it – probably in about 2002.

Simon Shields Location Independent Lawyer
Simon, practicing from paradise.

What do you find most fulfilling about your current job?

The legal work is just as interesting, and less stressful as I don’t do the face-to-face or hearing work anymore. You may have heard the adage that “law is great, except for the clients” – well this life of mine is as close as possible, I think, to do litigation without clients.

Of course the option of doing this anywhere in the world (given widespread broadband coverage) is an unparallelled lifestyle bonus. I mean, it’s just what others dream about but most never try (or can’t with family obligations).

When people ask me about it I always say that permanent travel isn’t all that it’s cracked up to be, but luckily it is most of it – and I’ll settle for that.

Do you have any advice for professionals who are interested in branching out from traditional private practice but concerned about what is out there?

Do exactly what I did. There are several major areas of Ontario law that I don’t practice where a person could do this, particularly family and criminal (and I am unaware of anything like this model from other jurisdictions). I often say that any lawyer who puts the work into writing and posting (for free) a thorough family law guide, thus placing themselves high in the search rankings, can write their own ticket for world travel. We all know how many family law litigants are self-repping today.

As well, what with legal aid cut-backs (in Ontario, eligibility only where there is a prospect of incarceration) there are heaps of criminal defendants crying for affordable quality advice and litigation support. There are of course numerous other fields out there where it can be done as well – lots of ’boutique’ practice room on the internet.

Don’t worry that your guides might be “giving it away for free” – people still want the experienced guidance and will hire you for that. As well, I have never had any liability concerns arise for what I have posted online – zero/zip/nada. (Ed: I asked Simon about insurance issues and he said as part of his requirements for admission to the Ontario bar, he does have a policy for E&O insurance.)

What are the downsides to working abroad, if any?

Time zones are fine, just apprise your client of the situation at the beginning. You’d also be surprised by the number of night-owls (or insomniacs) that I end up e-chatting with in the middle of their night. I promise 48 hour turnaround on all emails (and usually provide much shorter).

I can use Skype but do not out of choice. Email is so superior as it automatically creates a word-searchable, verbatim record of what my client and I have said. It also allows communications to be so much more considered and verified. Verbal communications with lawyers are peppered with qualifiers all stemming from the fact that competent advice needs to be verified – even in fields that you work in regularly. Memory fades since the last case, law changes, the context of the case needs time to gel, etc. Imagine a practice where all your communications with your client are by letter – and all advice, promises and expectations are crystal-clear. Both my clients and I love it.

What do you have to say to those who tell me lawyers can’t have fun?

Once I explain to people or colleagues how I practice they never ask that – it would be a silly question, and besides – their minds are too busy churning away on how they can do it to ask.

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