How 5 of my biggest mistakes turned into my greatest life lessons
Confessions of a high achieving woman

In my experience, life will keep serving you the same lessons until you decide to learn them. 

I have a deep belief that all of our “mistakes” are actually guiding us towards a more expanded version of ourselves. That although we may deem them as failures or as being misguided, they actually are pointing us to our deeper work and possibilities for our lives. The question is, can we give ourselves the grace and compassion around these “mistakes” and embrace the lessons behind them or will we continue to judge and berate ourselves, looking at them from a place of lack, rather than a place of learning? 

It took me a long time and a dedicated practice of self-awareness to shift my mindset from “mistake” to lesson. Like a broken tape, my inner critic always had a way of telling me how I should know better and needed to just strive harder. “How come all of those other women can do it all and you can’t keep up?” the negative voice would play again and again in my head. I held a lot of shame about my mistakes and my failures, often making them mean something about me and my character, rather than having the compassion to simply see my humanity. What was life trying to teach me? 

I work with women now in my coaching practice from all over North America who are on their path of expansion and empowerment. Women who are brilliant leaders and entrepreneurs, taking brave and bold steps towards their deeper truth. Many of whom, like me, are still being challenged to learn the hard lessons served to many high-achieving women. 

These are five of the biggest mistakes learnings on both my personal and professional path and how they became my greatest lessons. 


At work and in relationships, I was a classic over-functioner. It may have seemed like I had it all together but have no doubt, over-functioning was a way I managed my anxiety. I would swoop in and save my team a lot, doing their jobs for them or completely rewriting things. At home, my over-functioning started early in my first marriage and came from a place of wanting to be a “good wife”, taking care of everything at home. I remember when my therapist pointed out my over-functioning at an appointment with my ex-husband. We were scheduling our next session and I leaned over and said to him, “hey honey, you might want to put that in your phone”. She immediately called me out on it and I got defensive, explaining how I had to do that or he would forget. “Let him”, she said, “that’s not your responsibility”. It had never occurred to me how much I had been over-functioning in our relationship, thinking I was just being a “good wife”. This morphed into maternal gatekeeping when our first baby arrived. Only I could rock our daughter the right way, know what she needed and put her to bed. Little did I know that my over-functioning would impact his confidence in having the ability to care for our daughter. The ironic thing is, I then began to resent having to “do it all”, without recognizing my responsibility in the matter. My over-functioning led to exhaustion, resentment and burnout. 

What are the ways you are currently over-functioning at home or at work? What are you worried might happen if you stop? What is the cost of continuing to over-function? 


For about 20 years I was a hustler for my self-worth. I felt better about myself when I was achieving, accomplishing and excelling. I remember my identity crisis during maternity leave like it was yesterday, whispering to myself “now I am just a mother”. When I wasn’t leading and accomplishing, I had no idea who I was. I never thought of loving myself purely because I had existed. That there was nothing I had to prove, no award I needed to win, no title I needed to have to prove that I was worthy. I just was. I was raised by loving parents and in a fairly functional family and yet still, I kept learning this lesson over and over again. The unhooking from praise, productivity and validation has been more freeing than I ever could have imagined. But it didn’t come without a complete unraveling. During the early days of Covid I lost all my non-profit consulting and I had too many emotional breakdowns to mention. Everything needed to be stripped away in order to remember who I was. And that even without a title, a job, or cash flow – I was still worthy. I am grateful for that lesson. 

What is more important to you than praise and validation? What are some ways that you show up to value yourself beyond your work and productivity? 


When I first started my career, most of my mentors and role models were men, or women who were anchored into their masculine power. Masculine power is very linear and easy to measure and quantify. It is more focused on power, control, goals, bank accounts, achievements, job titles. For many years I was all masculine power and forgot what it means to be connected to my feminine power. I believe wholeheartedly that a big part of why I burned out was because I had no access to my feminine power, and was totally severed from the head up, in the doing, racing through my life. 

Feminine power is non-linear and much more receptive and open, it is curious, connected and creative. When you are anchored into your feminine power, you are attuned to your intuition, and that will rarely lead you astray. When I look back at how I was living my life for 20 years, I see how I led me away from myself, my inner knowing, my intuition. I rarely listened, had “time” for stillness (or saw that as being unproductive). It was only when I started reconnecting with my Feminine Power that my path in life started to become clearer, and clearer. 

Instead of asking yourself in the morning what you have “to do” today, ask yourself how you can serve yourself today. Then listen. 


If you told me that fear was driving my actions for the better part of a decade, I would have scoffed at you. But in retrospect, I can see how fear drove most of my actions. I would say yes to things all the time (people-pleasing) because deep down I had a fear that if I said no, I wouldn’t feel worthy or I wouldn’t be needed. I had an inability to put up boundaries because deep down there was a fear if I said no, I wouldn’t be liked. I did “it all” because I was scared to ask for help in fear that it would make it look like I couldn’t handle it. I worked out at 5 am every morning, not because I wanted to be a pillar of health but because I was afraid of gaining weight. So how much of your life is being driven by fear? 

I recently heard that every decision we make (yes every single one) is either driven by fear or by love. My path now is one of consciousness. How can I approach my decisions from a place of love, not fear? Each time we make a choice or decision in alignment with love, we move closer to ourselves. Every time we make a decision based on fear or lack, we move away from our true selves. So how do you want to live?


“I am not creative”, I told myself this for years based on some feedback I received in an art class. My very linear mind at the time anchored into a story I wasn’t creative because I couldn’t draw. I remember being in my 30’s and someone told me I was creative. “No, I am not”, I said. She then pointed out how I very creatively structured a strategic partnership and pulled together some very abstract thoughts into a succinct platform that resonated in a deep way for the company we are pitching. I had an “a-ha” moment. Oh maybe I am just not good at drawing, but I am still creative. I loved to dance, to write, to create ideas, companies, presentations. Maybe I was creative.

Now I question and am curious about everything. How old is this story I have been hanging onto and is there overwhelming evidence to support its truth, other than the filter in my mind?

I live by Byron Katie’s four questions. 

  1. Is it true?
  2. Can I absolutely know for sure that it’s true?
  3. Who am I, how do I act, feel etc when I believe that thought?
  4. Who am I without the thought?

Question your thoughts, change your life.