Heather Kerr – Reinventing herself from International Tax Lawyer to Artist and Life Coach

When I read about Heather Kerr’s almost unbelievable story of reinvention, I had to meet her to find out how her story started, why she chose to do what she is doing, and what obstacles she faced in the process. This remarkable transformation sends us all a message that we need to listen to our heart’s callings and embrace them. You never know what will transpire if you do!

As we spoke, I could see the pure conviction in her eyes that every decision she has made, regardless of how it seemed on the outside, was a perfect one for her. 

PPP: Heather – tell me about your story – where did it start, and was there a major defining moment/s of realization that changed everything?

I guess my story really began with my father growing up in the dust bowls of the depression era in the prairies in Canada. My Dad never forgot what it was like to struggle for money, and he had a huge focus on me having a financially secure job. Needless to say, a lot of “shoulds” helped me make my career choices.

I was an economist with the government and then went back to law school to become a tax lawyer. I practiced tax law for 25 years. It challenged my brain, which was good, and I liked working with clients. Eventually, I became a partner and responsible for a group of professionals at my firm. What I loved the most about being a leader was mentoring women and inspiring people to be the best that they could be. 

I never really understood why so many women had such a constrained view of what was possible for them – if their goal was to be a partner, I would offer them different points of view to make them imagine themselves as a partner. What decisions should they be making now if they could visualize their future? Ironic that I am still doing that to this day! I thought I would definitely retire there – compulsory retirement was at 58 or 60, but then I had a transformational event which changed absolutely everything in my life.

A Repressed Creative Passion Shows Up

PPP: Tell me about that, Heather!

I went on a trip to Paris in the early winter of 2014. Even though it was February it was quite warm, and I happened to be there during a week when the locals leave for their holiday week, so there were very few people in the streets or museums. I spent a lot of time in empty art museums and walking around the streets, drinking in the art and architecture – just taking it all in. If you stand in front of a painting for a while, it’s almost like you can feel the spirit of the artist. That all just infused in me.

Then it began. I started having completely vivid dreams of me painting in front of large canvases. I could feel the paintbrush in my hand, and I could see every detail of every painting. I would wake up in the morning and write down all I had dreamed of in great specifics. I ended up getting to 51 paintings – all dreamt in perfect details and images in my brain!

PPP: That’s incredible! What did you do with these visualizations?

I wasn’t quite sure what to do with them! It was strange, because I hadn’t thought about my creative or artistic side since I was a child. When I was in grade 5, my art teacher made a really unkind remark about my art – which was quite traumatic for me because I remember crying about it for a month. I was highly sensitive, and expected praise but instead got suggestions which I took as criticism. After that, I labelled myself as not creative. In fact, if anyone suggested we do a “creative” activity, I’d immediately feel incapable.

When I came back to Toronto from Paris, my brain tilted completely! My first thought was to notice I wanted change at work. Maybe I should switch to a new practice area. Or maybe I could move into HR at my firm and help women specifically. As I was sorting this all out, I joined a networking club for women in Toronto called Verity. It had a lot of entrepreneurial women and I thought maybe I could explore the entrepreneurial tax world.

The ironic thing was, as I went to every networking session, the only women I seemed to meet were artists or creative people! Only 5% of the women at this club of 800 business-oriented entrepreneurs were artists or creatives, but these were the people I always seemed to meet. Interesting how the universe works! 

Heather Kerr Unveiling a Passion

From there I was invited by well-known Toronto artist and Verity member, Gail Hill, to join a group where she taught us a process called CreativeSelf. This group was instrumental in helping me begin to see myself as an artist, even though I was still a tax lawyer and hadn’t painted since I was child.

My whole mindset started to shift as the women in CreativeSelf and at Verity viewed me as the artist I talked about becoming, rather than the tax lawyer I was. I signed up for a short summer art course and then in a weekly art course in the fall.

My mindset shifted so rapidly that by the end of October, I left my partnership and the tax world and started to paint! My vision of myself as an artist was just so clear and compelling that I physically could not sit at my desk and solve tax problems anymore. I had 3-5 years left till full fledged retirement but I couldn’t wait.

Embracing a New Creative Expression

I didn’t continue with my art class for long. I found that the art world was also full of rules. I felt freer and more creative than I ever had before and I realized the creativity was coming from a deep place within. I wasn’t going to constrain that by complying with anyone else’s rules or learning about what other artists had done before me. I decided I’d teach myself by painting and trying whatever emerged and just letting it flow.

This was a huge departure for me. I’d always been very self critical and overschooled. I had nine years of university before I started my job, and I always wanted to do more and be better. But when I did my painting – it’s like, nobody had to tell me what to do or approve what I was doing. I felt like everything I created was beautiful!

PPP: That’s an unbelievable revelation and journey, Heather. How did people around you react, and what internal and/or external obstacles did you face at that time?

There were a ton, Kavita. Don’t get me wrong – I was going through constant freak-outs! I was terrified, and I thought I was going crazy. I often thought “what would my father think if he were alive?” Obviously there was a huge financial hit as well, as I’d alway been the main breadwinner. My kids were kind of shocked as was my mom.  They were a bit worried and they also welcomed the change. I’d always been a workaholic and they knew at some level that this was good for me.  And they’d see me more.  

Many of my work colleagues were unpleasantly surprised. When you change up your life, especially when you’re a leader, it has an impact on the people who look up to you. They wondered why I was doing this. Why would someone give up their job?  What did this mean about their choices? 

When you make a change, the people you leave behind often feel personally threatened by your choices. Change is something that our brains hate. If the person you look up to changes their path and finds a different one, you begin to question yourself as well. 

Creating Resilience in the Face of Change

PPP: How did you overcome these obstacles and stick to your decision?

I think that if anyone is contemplating a change you need to have two things, which I had. One is a vision. The vision I had in my head about my future self painting was compelling and blissful. I think it is very helpful if you have a really compelling reason or intense vision about what you want to do in the future. It helps to counterbalance the uncomfortable feelings you are going to have as you navigate all the changes you’ll need to make.

The second thing is support around you. If you have a supportive community who is in favour of your change – a squad of supporters who can reflect back that image of you that you have – it becomes so real. I had that with my CreativeSelf group and Verity supporters and they helped me navigate change, failure, switching, and learning. If you want to make a change, it’s so important to have people surrounding you that can imagine you as the person that you are becoming, and not the role you have always played.

PPP: It sounds like your vision and community helped you to be where you are today. Where are you now, in your journey of reinvention?

I am still growing. I painted full-time for two years, but still had that psychology and mentoring piece inside of me. I also was developing a different view on creativity. People say you need 10,000 hours of working on a skill or a ton of schooling to really master something, but I disagree with that. There isn’t a set time. The more open and free you are, the more prepared you are to listen to your inner knowing and intuition, the faster it can happen. 

Heather Kerr A New Purpose

I believe that if someone like me who had no artistic talent at all can suddenly do beautiful things, anybody who desires to create anything can do it if the calling inside them is strong enough! I believe that the calling is there to tell you CAN do it!

My next step was to learn how to serve people to help them create whatever they want to create in their lives as well. I studied with a variety of alternative teachers – energy workers, a Reiki master and a shaman, and eventually got introduced to life coaching, which I found to be transformative. So I studied under two life coaching programs – Martha Beck’s coach training program and The Life Coach School’s life coach certification program and now work with clients as a Creative Expansion Coach. And of course I still paint.

My clients are entrepreneurs, career women, and other high achievers who are yearning to create something new in the world – whether it’s art, writing, new business ideas, or even new ways of doing things in the world. Some of them are still in traditional jobs, and some not. It doesn’t matter. They’re all suffering or frustrated because they’re not creating at all, or not at the level they want to be, and they have a deep yearning to do that. The biggest thing I bring to them is my belief that they can do it. 

And now I have my own space, in beautiful Prince Edward County – where I hang my art and a workshop space where I can hold events. I’ve literally changed everything in my life. Yet everything is here that I need, and I am happy.

How to Navigate Your Own Reinvention

PPP: From your experience, Heather, what would be the main lessons learned which you can share with our audience to help them with their own journey of transformation?

I would say I have five lessons that I’ve learned which may help people to navigate their own reinvention:

1, How you label yourself in your mind changes everything! I went from saying that I am not artistic or creative to telling myself that I was an artist. More importantly, I started visualizing it; I started believing it, and I started talking about myself that way. Our brains can’t tell the difference between what’s real and what’s imagined. So an imagined experience is just as real and transformational as having a real experience. Our brain eventually starts to believe the things that we are imagining. That’s why coaching for athletes and visualizing the future you want is such an important step. Visualization may not even be the right word. I actually imagined holding the paintbrush – with all my senses – like it had already happened. Feel it in your body like it’s already been done. 

2. Know that you are inherently creative! I truly believe that all humans are inherently creative, and that’s important because there are infinite ways to create what you really want. It’s so important to be open to the ideas that arise within you – to trust in that openness and allow your own ideas to emerge. People will give you evidence that it won’t work, but you need to be open and allow your own unique ideas to come through. The more you believe that they are uniquely yours, the more successful you’ll be. 

A lot of us want to have a transformational change, but then we bring our own self into it. We bring in all those old constraints that boxed us in before – we become the same person we always were but in a different environment. So if you’ve got a yearning inside of you to change up your life, if there is something in you that wants to come out – you need to be open to try. Do exercises to drop you out of your thinking mind – anything that drops you into your senses and out of judgement and limiting beliefs. Try different activities to train your brain, like slow breathing, contemplating an object, going for a walk, anything. Ideas will pop out of you when you least expect it.

3. Failure is a good thing! When you are in the transformational world, we all want everything to be inspirational and rainbows and daisies. But when we are evolving, we are testing our limits! When we test our limits our brain is going to hate it – because our brains are wired to keep us safe. For example, you could be in a job that you’re unhappy with and is super boring – but when an opportunity arises – your brain will tell you that’s a bad idea. You may even get physically ill. Our brains never want us to change. Even if you’ve got a great idea and are really inspired – your heart knows it’s the right thing to do – but your brain is going to freak out.

There have to be obstacles in your way. And sometimes we will get it wrong! Someone once said to me, “Everything we do, we are either winning or learning!” In a transformational world if you are not failing, if you are not overcoming obstacles or hurdles, you are probably not evolving as much as you could be. Shift your mindset to believe that. 

4. Try and remember to enjoy the process! With change, you will need to learn a lot of new things. For example, as an entrepreneur you may need to learn new technology, how to sell, or other things that get you out of your comfort zone. Your brain will start telling you you’re not good at it, but try and train yourself to think of three ways to make the new task fun. Learn to enjoy it and it will create peace of mind. Good things will come out of it!

5. Don’t strive for perfection! When I started coaching I thought I had to be the consummate professional and I was striving to be polished. Yet I wanted to be coached by people who are not perfect, who would share their struggles with me. People are going to love us more if we are not perfect; they will give us the benefit of the doubt. Giving myself the permission to be imperfect has made me enjoy the process so much more. When I painted I went into the mode where I didn’t have to be perfect. Yet, in fact I believe everything I create is perfect. That’s because I just loved it so much!

PPP: Those are great lessons Heather – thank you. What would you say you are most proud of at this moment?

I think I’m most proud of learning to love myself and give myself a break. As I learn to love myself, I enjoy what I’m doing more and it just makes everything better. That’s something I definitely struggled with all my life. I don’t have to succeed to be worthy! I’ve really developed a lot more compassion and love for myself. That’s what I’m the most proud of because that’s been the hardest part for me. To have my own back, and to honor what I want to do. It’s a constant practice. It’s like if you’re a marathon runner and don’t run for five years you will be flabby. I think self love is a practice that requires intention and practice. And awareness. 

PPP: Thank you Heather. Do you have anything else you’d like to share?

I think that especially with what’s been happening in the world in recent months, there has never been a time when the world needs our unique ideas, solutions and talents more than now. I think we all have to step into our creative possibility. We have to step into who we are and who we can be. Our intuition is important to listen to, because it tells us what we are capable of doing in this world. We never know what small changes we make might have profound impacts.

PPP: You’re so right – if we don’t do that – then the world won’t have the gifts we have to share. Thanks Heather.

Thank you. I want to encourage you and commend you on the platform you are creating to inspire people around the world – it’s so important.