My story: 10 transition steps from law to career counselling

This post shares some background on my own career transition. Career transition stories usually aren’t too linear and have idiosyncratic twists and turns, but if you get the details of a few stories, you’ll most likely see common themes or strategies. Here, I’m sharing my example in case it sparks some ideas for others looking to get moving on a career change.

Step #1: Admitting the current situation wasn’t working

This step is naturally very challenging for a lot of people and I think, in my case, two things helped me let go of my imagined legal career and seek out something new.

When I started law school, I was very focused on a career in human rights law and activism and pictured myself working for Amnesty International or the United Nations. I stuck with that goal through three years of studies and was pleased to find my interests proved true as I enjoyed my public international law courses and equality-related projects the most of all my studies. (Some interests had not proved true enough to stick with in the past!) But law school wasn’t a great fit and it exhausted me deeply — it exhausted my spirit. So by the time I finished I no longer had the energy or motivation for competitive rounds of internships and interviews at the big name organizations I originally had in mind.

I also had a mortality check at the age of 26 when a friend was killed suddenly in a collision with a drunk driver. It was a sad wake-up call. Life is short — maybe much shorter than we expect. I made a choice to live more in the present and to do my best to make sure I enjoyed my days and did not sacrifice present happiness for uncertain future rewards too often. I was still planning for the future, but with a different approach and a new commitment to myself that made it easier to let go of my now ill-fitting career plans.

I was fortunate to find some human rights-related work locally, in Toronto, and as I made the transition from my student days I stayed attuned to my day to day quality of life and kept my material needs and expectations low for a sense of flexibility. After working with two different organizations, I discovered that I did not have the energy for short-staffed under-resourced non-profits either (they are not all like that, but that was my experience!) and I started to wonder about other career options outside of law and human rights. I held a hopeful perspective that perhaps I could create a more satisfying life and career for myself. I kept working and even took on more hours where I was working at a disability rights organization, but I started exploring.

Step #2: Looking around for ideas and inspiration

My career questions opened up lots of conversations with my friends about their work and career satisfaction. At this point, I didn’t see any personal role models in my circle for making not-so-typical career choices or going off in a different direction from my education. My classmates took legal jobs and other friends were more established in their work, working full-time and often parenting too.

Books became my inspiration. I looked up all kinds of career-related books at the local library trying to get a wider sense of options and possibilities. One book jumped off the shelf at me: “Creating a Life Worth Living: A practical course in career design for artists, innovators, and others aspiring to a creative life” by Carol Lloyd. This was the off-the-beaten-path inspiration that I needed! It was written in a workbook format and included all kinds of interviews with creative people about the evolution of their careers. I did all the exercises over a few months and soaked up all the encouragement for making choices based on your own needs rather than societal expectations.

A couple of other books were really inspiring too: “Voluntary Simplicity” by Duane Elgin and “How to Live Without a Salary” by Charles Long. These books helped me to be more comfortable with continuing to live like a student to some extent. That lifestyle didn’t create the pressure of feeling tied to my job for the income. I was single without kids, so I just had to look after myself and the flexibility of a relatively low cost of living helped to me continue my exploration without feeling I had to settle for the job I had.

Step #3: Building myself up

The good thing about my soul-deep exhaustion after law school and my not-so satisfying human rights jobs was that I was really ready to get back to doing things that made my heart sing and so I committed to those activities outside of my work hours.

Craft projects and art classes were (and are!) at the top of my list for enjoying life in the moment. Over a few years, I took classes at the Toronto School of Art and the Canadian Book Binders and Book Artists Guild, as well as adult education art classes at a local high school. I set up a dedicated craft project table in my living room so it was always easy for me to sit down for a little while and work on something.

At this time I also took up running. Since law school, I had struggled with low moods and my doctor said that vigorous physical activity a few times a week was shown to benefit mild to moderate depression symptoms. Running was my exercise of choice because it was uncomplicated and cheap — I just had to get a good pair of shoes and find a decent path.

These activities at first seemed unrelated to figuring out my new career direction. I just wanted to enjoy my life more. But it became clear that they really did make me feel better and as I felt better I could imagine many more new possibilities for my career and see more opportunities. My hope and commitment to creating my own path only strengthened. It also became very clear to me that I was willing to trade off some income and common work benefits for time. Others had different needs and priorities, but I wanted lots of time for art, fitness, volunteering, and my personal relationships. I was clearer on what was truly important to me. So I figured out that one key criteria for the next step in my career was a fair amount of control over my own time.

Step #4: Not paying attention to everyone’s opinions on my life

Back in the year after law school and after my year of student-at-law work to qualify for the bar, I decided to work part-time and got my first job at a Toronto human rights organization working three days a week. That’s when it became clear that other people were going to react to my career choices and share their opinions with me — helpful or not!

I figured out from those reactions and replies to my questions about new options and other fields that people have a lot of fears about career uncertainty. Fears about joblessness I easily understood — we need income to survive — but I was earning income and looking after myself and so I was surprised by how unsettling my ideas and questions were for some people. Those reactions to my career ideas and choices said much more about those individuals than about what I should do for myself.

I became more careful about what I shared with whom and I sought out people who related to my interests and were inspired by my career exploration and determination. People who cared about me a lot but were inclined to worry (hello Mom and Dad!) received thoughtful updates, not outpourings of all my confused feelings and ideas for experiments.

Step #5: Experimenting

At some point I realized just how much I liked reading all those career books and talking about them — more than most other topics. And I also noticed that I was giving bits of advice to friends who were unhappy in their jobs. I was the person to call if you hated your job but your parents wanted you to keep it! My approach was: Life is short. What else could you do? Why not try to make a new plan?

I had the idea to look into career counselling as an occupation and discovered a Career and Work Counsellor program at a local college. Having recently invested 4 years and thousands of dollars into legal studies only to realize I didn’t want a legal career, I was a little shy about throwing myself into more education! But $250 for a weekly night class over 12 weeks sounded like a low-risk investment to see if my interest and curiosity about the field had any legs.

I enjoyed the course and was inspired by the textbook: “The Career Counselor’s Handbook” by Howard Figler and Richard N. Bolles. That one course led to three more at the college, one after the other, and then a university Psychology 101 course that I did through distance education. The college courses also connected me with people working in that field and others with interests in different kinds of counselling and social service work. I was finding that in many ways I had more in common with the counsellor-types than lawyers and project managers.

During this time I was very fortunate that I made a connection that led to some on the job testing of my career counselling interest. Then working on a women’s rights project at the law library at UofT, I met the Director of student Career Development Office at the law school. We chatted about her career transition into career counselling, my interests, and the course I was taking at the college. Later, when she was suddenly in need of some part-time help for a couple of months, it was a golden experiment opportunity!

At any point here I could have decided that career counselling wasn’t a good fit for me and then started exploring another interest. My idea was to take my time while still working in a law-related job to get enough of a taste of this new field to find out if I wanted to commit to becoming a career counsellor.

Step #6: Getting the necessary skills

The threshold for “enough of a taste” of the career counselling field was totally personal to me and my situation. After a few classes in the college program, which was focused on training people to work in employment counselling agencies, I thought that I would prefer to work on my own, perhaps similar to how some other kinds of counsellors and a lot of therapists work.

This focus on self-employment in a new field meant that I needed to be confident in my counselling skills and also develop some business skills. I chose to explore more in-depth counselling training and talked with a friend who had studied at the University of Toronto for her Masters in Education in Counselling Psychology. I also looked into some coaching programs as well, but as a back-up to my self-employment idea I was interested in career counselling at college and university career centres and it turned out that the credential those offices required was an MEd in counselling psychology. I gathered more information about the program, the admission requirements, and how many students were accepted each year.

I also discovered Enterprise Toronto, a small business centre that had workshops and business advisory services for free. I learned just enough to give more form to my business idea and start planning in a way that worked for me. Later on, I was turned on to a helpful business book for therapists and counsellors, “Building Your Ideal Private Practice,” and worked through the chapters to develop my idea and plan how I would find clients.

Step #7: Being deliberate about finding support

Making the decision to go back to school was hard. I never thought I’d go back to university again after completing law school! And it was a big investment for me. I decided to meet with a career counsellor as I was grappling with this decision. Those sessions were a great support in sorting through my questions and feeling confident in my decision. (Also, it was good for me to be a career counselling client myself and have that experience for the work I was planning to do – so it was kind of an experiment of sorts from that angle.)

As my business idea developed, I realized that moving from part-time work and part-time studies to working on my own had the potential for loneliness and isolation. I am the kind of person who likes to put my head down at work and be busy and I build work relationships relatively slowly so working on my own really suits me in some ways, but I knew not being in an office with others meant missing the friendly Monday morning chats and the offers to run out for lunch together that can offer positive shifts in energy. I lived alone and I had already had a few short stints of working from home and I realized the real challenges of too much time by myself.

So I deliberately sought out new professional connections. I found an association of career counsellors and a women’s entrepreneur networking group that both had regular meetings. I looked for occasional conferences and workshops to attend that were related to career counselling or to self-employment. Eventually I also found a couple of small groups of like-minded counselling colleagues who agreed to meet every so often and later I asked some colleagues to get together for a counselling-themed book group.

I built a network of people who understood what I wanted to do and how I worked and who were there to call on if I needed ideas or advice and I also built a schedule of professional social interaction that balanced out the isolation of solo-entrepreneurship.

Step 8: More experimenting!

My personal experience, studies, and reading led me to want to focus my work on creative living and finding meaning in work. I decided I wanted to focus on artists and activists as I started my own career counselling practice. Artists tend to seek meaning and personal expression in what they do and I had an affinity for artistic pursuits and the arts and culture world. Was this a good focus? What did I need to learn?

I discovered the Artists’ Health Centre in Toronto and decided volunteering there might give me a better perspective on the support that artists need for their lives and careers. I offered my time to be useful — mostly doing filing and making phone calls — but met people, learned lots, and made a connection to the Artists’ Heath Centre Foundation (now the Artists’ Health Alliance) and its education program that would be a great benefit for personal growth and also for my business growth. I eventually facilitated workshops through the education program and was introduced to the Dancer Transition Resource Centre where I remain one of the career counsellors on their roster for referrals. You never know what might develop from a once a week volunteer commitment!

And of course, beginning my private practice was an experiment itself! That kind of business is a slow build. To take the pressure off, I had part-time career counselling contracts at the University of Toronto on and off for several years.

Step #9: Being patient

You’ve probably gathered from this story that it took a few years from my decision to explore options to my various experiments, studies, jobs, volunteering, and then having my own business. It did! I was puzzling over things and reading career books starting back in 2002, took my first college career counselling course in 2004, started my counselling psychology Masters in 2006, and launched my own business in 2007. Others move faster, but this was my journey.

And it wasn’t completely a smooth ride! Lots of experiments in my career exploration didn’t work out for me.

At one point I thought about starting a craft business and put some energy into that only to realize I was a slow maker and didn’t like the mass production aspect. I volunteered a couple of places where I didn’t fit in or where there weren’t enough opportunities to interact with others and learn. I took a part-time career counselling job at a University of Toronto faculty that didn’t work out at all – after I did the training, I didn’t even have one shift!

So I learned to expect setbacks did my best to be patent with my self-imposed timelines. I kept my eye on the next experiment and opportunity and focused on the next step I could take to clarify my goal. Sometimes it takes the time it takes, but support and learning can work wonders.

Step #10: Balancing focus with flexibility

So with that combination of patience, curiosity, and effort, I reached the day when I could introduce myself as a Career Counsellor. I launched my private practice with a self-made website and funky business cards designed by a friend of a friend and I rented just a few hours a week of office space on Madison Avenue.

I refined and implemented my outreach and marketing plans and followed my vision with one of my favourite career theories in mind: Planned Happenstance. This theory posits that we need goals and vision to take action and feel focused, but we benefit from paying attention to chance events and welcoming them. (See the book “Luck is No Accident: Making the Most of Happenstance in Your Life and Career” for more on this perspective.) Good fortune has played a role in how things have unfolded for me over the last 10 years and my openness to unexpected events has served me well. Who knew that the earnest young 25-year-old law student would travel a bumpy career road and transition into a career counsellor at 34 and an entrepreneur at 36? This path could not have been predicted, but it has been fulfilling.

And that’s a not-so short account of my transition! It appears a little more linear than the way things really unfolded, but I hope the emphasis on what helped me find my way offers some ideas and inspiration!

This month marks 10 years since I took the leap into entrepreneurship and started working with career counselling clients as a private practice business! To celebrate, I am sharing some “top 10 lists” and other 10-themed resources. (You can find links to all the 10-year resource posts here.)

If you like these kinds of career transition stories, I highly recommend checking out the stories on the Careershifters website, a UK career change organization with a great blog and a whole bunch of personal career stories:


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Thanks for sharing your journey, Anne. As a former satisfied client, I fondly recall the work we did together in your downtown Toronto office. So glad you went down this path because you really helped me a lot!