How to Get There from Here

Heather Greenwood Davis is a friend and colleague from my days practicing law at a large Canadian firm. We met after we had both chosen to make career detours that took us off the partnership track and onto a small team driving an unpopular new initiative that most members of the firm wanted nothing to do with.

Hmmm.  Interesting career move, you say?  You’d be right.  And it gets more interesting.  Today, Heather is a widely-published freelance writer about to embark on a year-long, blog-recorded trip around the world with her husband and two children.  Here, in her own words, is how she got to that place.


When Linda asked if I’d be a part of the stories told on this site, I had two minds about it. On the one hand, I’m honoured. I love what she’s doing here and I believe in its importance. On the other hand…what to say?

I decided I wanted to share the one thing that has been a common thread and the most use to me throughout my life…losing control.

It has come to my attention that I am not to be trusted to steer the direction of my own life. Trying to do it has rarely met with success.  The opposite is also true: when left to its own devices, my life almost always ends up exactly where it is supposed to be.

As a kid, the lists I’d make in the spiral-bound school-years album where my mother kept each year’s school picture detailed all the things I wanted to be when I grew up – everything from a maid to a doctor.

Somewhere around the fourth grade, the notations changed. I wanted to be a writer. That year I started my first newspaper using the school’s old mimeograph machine and writing stories about classmates and school teams. Looking back, I’m not sure who read it, but I didn’t care. It was the writing of it that mattered.  There was no going back.  I wrote entire novels in grades 6 – 8 that never made it beyond my bedroom door and were based almost entirely on people I knew and crushes I had.

A co-op placement in grade 11 meant I was in a real newsroom for the first time. Our local weekly paper let me write a column about our school and suddenly, with better copy editors and a glamorous headshot photo, I was doing the thing I had fallen in love with years earlier.

There was never a question – despite foolish guidance counselors who tried to dissuade me – that I’d go off to Journalism school. And when I was done I knew where I wanted to be: The Toronto Star. And though it took more than just forcing an interview with the City Editor (did that), I did eventually get a job there.

End of story right? Girl dreams. Girl works hard. Girl gets wish.

And yet, no.

It seems sometimes – often – life hands you things you didn’t know you needed.

Three months into my contract position at the Toronto Star, a girlfriend called with a dilemma. She was studying for the LSAT (law school acceptance test) and had no one to practice with. I was working the night shift at the time and agreed to send away for the materials and do the practice exams with her. In order to get the materials, you had to list three law schools that you planned to apply to. Whatever. I picked three and got the materials. The questions were tough, but I did them the way people do Sudoku or crossword puzzles, never thinking I’d need to pass a test. And yet, when the time came for my friend to write the exam, I gave in and wrote it with her just to see how much I knew.

I passed with flying colours and was accepted to all three of the schools I’d listed despite having no interest in attending. I found it hilarious. I had only done the test for gloating rights, and gloat I did.

I walked around the newsroom telling anyone who would listen that I’d gotten into law school. Word got up to the paper’s Managing Editor who promised me heaven and earth – or at least consistent contractual work – if I went. I agreed and that September started law school at the University of Windsor.

I hated it from the start. Classes were fine but I felt like I was missing out on real life. Who cared about classes when there were stories waiting to be told?

I went to class sporadically – opting to spend mornings at the gym and afternoons napping – and grabbed notes from friends to study from. I became the Toronto Star’s Southwestern Correspondent and covered everything from labour disputes to Isaiah Thomas, the Detroit hero who was then basketball coach of the Toronto Raptors.

I thought I was maintaining control of my life.

When I finished school and went back to the Star looking for full-time work, editors had changed and it was suggested that I finish the lawyer process (write the bar and article (intern) at a firm) before coming back. I grudgingly agreed.

And that’s when I lost all control.

The year I accepted an articling position at a Bay Street law firm was the only year in the firm’s history where they offered a 2-for-1 special: article with the firm and you were guaranteed a first year associate position when you were done. At a salary that would put me very close to six figures, the hourly wage from the newspaper began to slip out of mind. From the moment I signed on, I was like a hamster in a fast-moving wheel. Except that I was not the one controlling the speed of the wheel.

Looking back, it wasn’t all bad – I found myself working with people I loved and who remain friends to this day; I learned a lot about people and our judicial system; and I grew as a person.

But while I was living it, it was a nightmare. Days would blend into night and I barely saw my new husband. Twice I worked 36 hours straight, sleeping in my chair. One of those times I was 7 months pregnant.

The next time I came up for air I was on mat leave with that first child.

Flipping through a Fit Pregnancy magazine I came across an ad that changed my life. There was a spa in Dallas, Texas that was dedicating a week to the ultimate in mother pampering. I dug out my Rolodex, called the spa and the newspaper and was off on my first travel writing story assignment. The story was a hit and I was offered a columnist position with the paper. I took it and for the next 5 years I took advantage of every weekend and holiday to dash off to somewhere else (while continuing to work at the law firm) and rekindle my passion for writing. I had rediscovered my lifeline.

Three years later, now the mother of a second son, I left the firm.

I am now a full-time freelance writer specializing in travel and lifestyle articles. I occasionally write about the law as well.

In July, I’ll fulfill a dream to travel around the world and my husband and two children will join me.

It is not where I thought I would be at this point in my life. It is not the straight line to a newsroom journalism career that I imagined for myself as I sat with the mimeograph machine in grade school.

It’s better.

My time at the firm was only one of several things that made no sense to me as I was living it. What was I doing in a law firm when I wanted to be a writer? The fact is, that seemingly off-side move was necessary for me to have the life I do.

Every wrinkle thrown into my life, including a completely tangential career in the law, has served me well.  What it has taught me is that there are no mistakes, just choices. And every one of them has the potential of offering you an even richer, more fulfilling time on this planet than you might ever imagine on your own.


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