Thrillable Hours: Simon Shields, Location Independent Lawyer

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.

18 thoughts on “Thrillable Hours: Simon Shields, Location Independent Lawyer”

  1. Amazing! Consider me inspired, Simon. I’m glad you mentioned things like non-residency, as those are the aspects of becoming location independent that I always wonder about: health insurance (don’t most policies require you to have provincial health insurance, too?) and taxes. What can I say? I’m practical…

    Thanks for a great Thrillable Hours!

    1. I actually don’t have any health insurance at all. Most private travel plans are premised on immediately shipping you back to your country of residence to put you under those local medicare schemes, and even then they are absurdly expensive.

      My experience is that the quality of medical care in most places is excellent and dirt cheap. I’ve never had better and faster medical care than in Malaysia (four visits for various parasites, infections, shingles once, etc), all at $4.00 a visit (meds and dressings included). Also in Malaysia I never waited more than 15 minutes after an unscheduled drop-in at ubiquitous clinics, even in the smallest of towns. Even in Greece a walk-in to the local hospital got me examined for a hernia and an X-ray for $5.00, turnaround about an hour. A private clinic colonoscopy in Greece costs me $150 Cdn, and an ultrasound $60.

      My health plan is to exercise and eat well. If I get something life-threatening or seriously disabling I’ll consider my budget and my options at that time.

  2. A post about a lawyer who works from…Greece could not do nothing else but attract me!

    As a Greek I cannot help it you see :)

    I love this story and I wish Simon (and anyone else who wishes to work from my country) best of luck.

    If you need any recommendations on where to go or what to do from a native, then I’d love to help!

    1. Ciao Maria,

      As I was reading the post, I saw that you are willing to help with places to visit. Although I am not working internationally at this point, I will be traveling from May thru August all over Europe. Greece is definitely on the list of countries I want to visit. It would be amazing if you could help out. Thanks!

  3. I don’t know if Simon will be looking at comments, but if so: Simon, how long do you tend to stay in one place? How many hours a week, on average, do you devote to legal work?

    1. I’ve been doing this just over five years now and my minimum stay is usually three months. I have also stayed in places for over a year. It’s really dictated by whether I like the place and how visa-friendly it is.


  4. See one man’s boring home practice is another woman’s travel destination. I am doing the same thing working back into England out of Ontario, Canada. So far it’s working really well but I am still lumbering along with SKYPE some of the time. Wholeheartedly agree about the ease of email though it works very well. Thank you good to feel I’m not alone although with three feet of snow outside Greece doesn’t sound like a bad option.

    1. Glad to her there is someone else out there doing this, though I have to admit it does tarnish my pioneer self-perception slightly ;-). Who are your clients? You are ewlcome to write me direct as I’d love to swap experiences:

      As for Skype I’m still p.o.’d with them after they confiscated my initial $20 registration credit because I used it so little. While I have some clients who request voice contact it’s usually people who want free consults and unresearched off-the-cuff advice. That’s a formula for liability that I avoid like the plague.

      Self-litigants both need and usually want detailed well-researched advice which they can go back to, recheck and reconsider. Email is ideal for this purpose and it saves me note-taking (which is invariably an interpretation of what was really said). My experience is that voice communications by lawyers are (if they are not bluster) so chock full of weasel words that they are next to useless. Why not go with a method that automatically ‘confirms it in writing’.

      I know you’re not arguing for Skype, I just wanted to make those points.


  5. I’d also like to know the answers to Suzanne’s questions :)

    Thanks for this post, I’m not a lawyer but this is definitely inspiring me to finally take the leap and leave the corporate world behind.

    There’s nothing that makes me happier than traveling, and there’s nothing to drives me crazier than sitting in this office on Madison Ave all day. So I guess my choice is pretty clear, but it helps to hear other success stories! :)

  6. Thanks Maria. Greece is one the best places to live in the world. The land, the people, the fresh produce, the fish, the cheese, the wine, …. they all allow one to live as god intended: simply and well.

  7. Hi Simon,
    Your story is inspiring. I begin my articles in just short two months back home in Canada. I say back home because I have managed to spend 1/3 of my law degree abroad, and am currently completing my last set of courses in Ireland. This is really interesting what you have done, and I commend you for modeling your work to fit your interests. I have often wondered how such a regional profession can ever fulfill my traveling soul. I have a feeling I will have many questions for you in the future…. Thanks for sharing your experience. I am passing this article along to my colleagues!

  8. That’s my dream….I hope one day i can do that also…imagine working while traveling…Wonderfull!!

  9. What a fabulous story. I’m sure many of us aspire to work from home/beach everyday and do a job which we love.

    This is a great example of someone who took the bull by the horns and just did it.

  10. Simon,

    Very inspiring story. Gives me hope other lawyers can do it. Time to work on getting unchained from the desk.

  11. Simon,

    This is an awesome story! I’m an Ontario lawyer too (though I think ‘sorta’ lawyer best describes me now as I don’t practice but do some law-related work). After much soul searching I’ve cobbled together a few location-independent gigs, but am still searching for the key to financial viability. Reading this was inspiring — I feel so close to finding the alternative that works for me — but at the same time find myself battling the urge to go back to the status quo. It wasn’t working for me, but gave me a much clearer idea of how I might have a roof over my head when I’m old! Financial insecurity is scary, especially when I feel like I have ‘legitimate’ other options — any advice about how to stay the course?

    Thanks for sharing your story!

  12. Simon- Thanks for sharing your experiences! I’d be curious to learn more about your business model- after reading your interview I’m still not sure I completely understand.

    I am a new lawyer in Washington state and would like to understand more about what you do to see if I can incorporate some of that in to my own practice. My five year goal is to have a practice that allows me to be on the road for 3 months of the year. Thanks for sharing!


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