I see myself as a poster-child for risk-taking. I believe it is the only way we learn, grow and reach fulfillment – in life, love and work. Everyone has a different threshold for risk. I lean more toward calculated risks but I take lots of them.

In reflecting on the many risks I have taken in my own life, I struggled to limit my discussion to only five. I decided to choose a few that I thought would really resonate with others – perhaps because they too have been at  similar crossroads in their lives and took big risks to move forward.

So here are five big risks that have paid off.

1 // Moving to Toronto for school

At the age of 17, I had a lot of choices to make as I graduated high school and prepared to start a new chapter of my life. I considered so many different schools and cities – from coast to coast – in my decision-making but I ended up choosing the University of Toronto.

Risk: Leaving my family, friends and my home community for the big city. Being 100% responsible for myself, studies, work and so on. Going to a massive university where I could potentially become “just a number”. Becoming lonely.

Reward: A meaningful education with bridges to continuous learning over the years. An amazing community that supported the launch of my first social venture (which achieved its 10-year milestone this year!). Mentorship from some extraordinary instructors and professionals. A great friendship with a young man who 8 years later became my husband.

2 // Ditching my career aspirations for the unknown

At the age of 24, I discovered that my lifelong dream of becoming a lawyer wasn’t such a fairytale after all. So I said sayonara to my life plan – 20 years in the making (yep, decided at 4 years of age) – and set out to find a dare-to-be-great situation. And I found it – less than a year later!

Risk: Forfeiting tuition and taking on the burden of debt-without-degree.  Disappointing others. Disappointing myself. Possibly getting lost in life.

Reward: So many good lessons that I could only have learned from failure.  The scenic route down a crooked path.  A wicked story to tell. Self-made. Vulnerable. Liberating.

3 // Letting go of people

There have been times in my life that I have found the need to let go of different connections. These might be contacts, friendships or professional relationships that weren’t the right fit anymore. Perhaps they weren’t reciprocal or healthy. Maybe it was that they couldn’t survive change. Each situation is different and so is the rationale for disconnecting but the act of letting go of someone is universally the same. And I have done my share of this.

Risk: Separation anxiety. Feelings of hurt. Misunderstanding. Possible regret. Loss.

Reward: It can feel liberating and productive like spring cleaning for your soul. It can help you become un-stuck. It can test your courage and bring you closure.

4 // Speaking courageously

In 2012, through a civic appointment to a City of Toronto ABCC, I received a true education in what goes on in municipal politics. In the early days, as a staunchly non-partisan citizen interested purely in the priorities and programs designed to serve (specific segments of) the Toronto population, I fell short in my duties. After a few months of feeling intimidated by procedure, deferring to the expertise of others, witnessing group think and otherwise participating in ill-conceived decision making, I realized what it actually meant to be held to a standard of due diligence befitting my role. I had to choose whether to “swim with the current” or “stand like a rock”.

Risk: Judgement from others in a highly public forum. Being labeled and dismissed as “one of those people”. General distrust of my views and the rationale behind them.  Refusal to provide necessary information to which I was entitled in order to make decisions for which I was accountable. Misrepresentation of my position in order to undermine it in the eyes of other decision-makers.

Reward: Being able to face myself in the mirror every morning knowing that I spoke (and voted) my conscience. Learning how to steer clear of “the noise”.  Being recognized by some as a “voice of reason”.  Finding and acknowledging an inner strength (and level of self-respect) I had never before realized. The satisfaction that comes with actually doing the job I was entrusted to do.

5 // DIYing

I am a really big believer in self-teaching. Although I greatly value what others have to share, for certain things, I learn best by “doing” it myself. I have taught myself everything from contracts to accounting to graphic design and yes, even some basic HTML code. I do not profess to be an expert in any of these things but I like to think I can get by.

Risk: It takes 10 times longer to learn and accomplish a task. There can be an exponential increase in the number of mistakes I make when I figure it out for myself versus having someone tell or show me how to do it. It can be an extremely frustrating process. It can be disappointing and demoralizing to realize that achievement does not grow in proportion to effort. People might think my results are mediocre (even though I might think they are awesome).

Reward: Discovering how to be both the teacher and the student. Developing a greater ability to be resourceful and problem-solve. Patience expands with each new trial. Learning victories are hard won but that much sweeter as a result. Appetite for risk grows as insecurities shrink. New knowledge that will probably never be forgotten.

What is one big risk you have taken that really paid off?

Working with the right people is all about attraction. Positively charged ions. Magnetic connections. Sparks fly when you’re surrounded by your dream team.

But who are they and how do you find them?  When I was a young, doe-eyed university student in the early days of heading up a student organization, I struggled to attract the right people. No one was committed enough or willing to develop the skills necessary to get the job done. (Hey I had a lot of growing to do too and plenty of mistakes to learn from!)  I couldn’t understand why until I realized that all I was doing was drawing in “interested” not “quality” people.

Sixteen months later, with a little bit more experience under my belt, I orchestrated a ground-breaking campaign to establish an innovative grant-making body with committed annual funding at the largest post-secondary institution in the country. Big stakes. Possibly an unachievable goal. What I was endeavoring to do was definitely no pub night. Yet I reached out and amazing people came to me in droves. So what changed?

I learned about leading others and discovered four key criteria that would enable me to collaborate with the right people and build dream teams.

Trust: Arguably a key ingredient in any functional professional or personal relationship. When you establish trust as a leader, others are more willing to sign on and commit. I garnered a bit of a reputation in my university days which got me a successful confidence vote. People knew I wasn’t a power hungry ego-maniac like so many other student leaders (sorry but it’s true!). I worked harder than anyone else, took on the least glamorous tasks and developed necessary skills at a rapid rate. People could see my determination and my own personal growth.  It is amazing how that kind of investment of self, attracts others. Likewise their commitment enables you to entrust them with the responsibility of a role instead of merely a task.

Mastery: I always gravitate toward people who are masters in a subject, skill or practice in which I would never personally claim to be an expert. I have my superhero power and they have theirs. What makes for a great team is that we do not duplicate strengths but instead complement one another. I look for people who can do it “better” than I can. (Otherwise seriously wouldn’t I just do it all myself?) In the last 3 years, I have engaged 10 very different people to support a critical project for (what I call) an anchor client. This allowed me to collaborate with people who have extraordinary work ethics, brilliant ideas, fierce risk-taking abilities and extremely unique expertise. None of them were like me and most of them were quite different from one another.

Initiative: I have always maintained that I do not manage, I lead. If you are looking for a manager, then we aren’t destined to work together. Managing others is a concept we really need to eliminate from our consciousness and replace with the idea of leading others. It might seem like semantics but the reality is that managing people is about fitting them into a pre-determined mold that benefits mostly you, your agenda, your company/organization, etc… instead of guiding them toward creating mutually beneficial possibilities. To that end, I love a person who can anticipate needs and take initiative because for me, that means playing an equal role – not a lesser one. It also means that they are confident in their own abilities and comfortable enough with their own autonomy to take risks, to pull it off and in the event they fail, to fix it and learn from it. (Gasp could there actually be something positive about failure?)

Aspiration: I have a highly acute BS-detector (one of my superhero powers) and when someone tries to convince me that our collaboration is the be all and end all for them, whatever chemistry we had disappears. Tell me about the mountain you want to climb or book you plan to write. Talk to me about your professional aspirations, the next step on your journey that you hope to be able to leverage our work together in order to achieve. My team should be one of many stepping stones and knowing that allows us both to maximize our time together. Is that different from what most managers want? Yes it is. They want someone to commit forever and give up their first-born so that all can remain stable and easy. I seek fluidity, fresh ideas and new people – all the time.

While there is more work involved in creating these kinds of dream teams, I believe the results are far superior.


Some people call it the daily grind. But I’m all about the daily groove. I figured this was the perfect thing to post today as a way to metaphorically dust the cobwebs off of this blog.

Let’s start at the beginning…I run a coaching and consulting business with a social mission. I work 7 days a week but I choose to start and end my day by LIVING. About 70% of the work I do is virtual which means that my home is my office, board room, lunch room and castle.

This is how I got my groove.

Fuel up. I find it impossible to do anything well without a good meal. I try to take a clean and balanced approach to food. I love my coffee (decaf, these days) and treats but the bulk of my day is filled with whole fruits, lots of veggies, nuts, vegetarian protein sources and yummy grains like quinoa and spelt bread. I find a little bit goes a long way in fueling my brain and body.

Check-in with your Zen Master. My most important meeting of the day is always a morning check-in with my personal Zen Master. Her name is Khailee and she is a 2 year old all-black shih tzu. She has a very soulful, all-knowing energy about her and that’s all I need to set my day right.

Be insatiable. I am always working toward goals and priorities. Everyday I put together a list of priorities and action items from my workplan for myself both in biz, health and life. As much as I love checking things off my list, I love knowing that I have more to work toward tomorrow.

Pick your moments of genius. You probably already know the optimal conditions for your own productivity and genius. Maybe you are a very early morning person who likes to get it all done quietly while the rest of world is still asleep. Or maybe you hit your creative peak after the kids are in bed or catch a second wind just after your 4:30pm yoga class. For me, I am oddly most productive during very specific periods of the day. For example, on weekdays between 8 and 11am, then again in the late afternoon/early evening between 3 and 7:30pm. But I really rock out on weekends – especially Sundays.  As a result, I can transform myself into a conduit for creativity and innovation at the right times.  (Psst RescueTime can offer some intel for those who haven’t yet found their most productive moments.)

Set boundaries. For me the most empowering word in the English language is “no”. I have learned through painful trial and error that sometimes you have to say “no” to others in order to say “yes” to yourself. So I am very conscious of setting boundaries on myself and my time. Trust me, the anxiety or discomfort that comes with having to say “no” is insignificant compared to the burden you will feel in biting off more than you can chew.

Forget multi-tasking. I used to be the poster child for the multi-tasking generation. I recently stepped down because my brain was too full that I was no longer able to juggle so many ideas. I have resisted the urge to open yet another tab in the browser of my mind. Try it.

Take a confidence vitamin. A positive pick-me-up or break from those hum drum feelings could be what you need. Writer extraordinaire, Alexandra Franzen has a whole whack of confidence vitamins to get your groove on.

Ditch the Debbie attitude. Have you become a Debbie Downer? Negative thinking is an act of volition. Business guru, Marie Forleo suggests giving yourself a spiritual smackdown. I did this recently and it worked wonders.

Contact the complaints department. Little hiccups in life happen every day and they can really get under my skin. About half the time, I forget about them pretty quickly. The other half of the time, I feel the need to state my case to the universe. I’m a big externalizer so in order for me to move on and be able to re-focus on the important stuff, I need an outlet. Usually a quick conversation that lets me get my frustration off my chest is sufficient. I have my go-to people for different types of annoyances. Once its shared, the complaints department is closed. Let it go and move on.

Breathe in. Fresh air can do wonders for productivity. It is a mood enhancer. The other day I opened the outside door of my sunroom along with all of the windows and let that beautiful breeze free flow as I got down to business.

Create your daily soundtrack. When you don’t want quiet, I think it is good to be mindful of the “noise” you have around you. I like music. A lot. I have playlists for everything: my mile run, commute via transit, weekend house cleaning, cooking, different types of work, road trips, etc… Here’s a favourite playlist to get you started.

Carry a personal totem. There are days that I know will require a superhero level of energy, grace and patience. And on those days especially, I carry with me a personal totem like this. That totem changes but usually there is some kind of symbolic or sentimental value attached to it.  Whatever it is, there is something about being accessorized in love that helps me to take on the world.

Show gratitude and love. There are 3 amazing creatures, without whom, I would be significantly less groovy: my husband and my two dogs. But truthfully, there are so many people I engage with on a daily basis that add so much value to my work and life. Collaborators, friends, clients, family, and team members are part of a larger community for which I am grateful. The trick is not just acknowledging that but spreading the word.

These are just some of the many things that I do to transform the daily grind into my daily groove. I am curious to know: what works for you?