
Volume 3, Issue 2, February 2024
Welcome to Volume 3, Issue 2 of The Root.
In order to support our growth, we require a strong network of roots. They anchor us and serve as a conduit for nutrients to help us develop and deliver on our goals.
I started this newsletter as a way to stay disciplined as a new entrepreneur as I grew my business, and as a toolkit for myself and others whom I advise and coach. I hope you will find these useful.
This year begins my 2nd full calendar year as an entrepreneur, advisor and coach. On this path, there have been my own doubts and growth. The aim of this issue – is to remind us that the doubts and next steps are actually part of the growth.
Each month, I aim to highlight books, articles and/or podcasts related to the chosen topic. I hope you will find helpful information to identify and manage burnout before it overtakes your daily life.
Thank you for following along our journey to Aspire to Grow.
Check us out at www.aspiretogrow.co <the .com domain was taken, but I like to think of it as “.co” for co-create>.
Off the Shelf – My Book Pick
Reboot: Leadership and the Art of Growing Up by Jerry Colonna
I decided to read Reboot: Leadership and the Art of Growing Up by Jerry Colonna at the suggestion of my own Executive Coach. I picked it up to continually learn to be a more effective coach senior leaders and executives. Jerry is known as the “CEO Whisperer”, so I didn’t expect the insights this book had for all leaders searching for more meaningful paths.
Colonna, a former VC investor turned Buddhist and Executive Coach shares his path from Executive to Good Human and the reawakening along the way.
Through his journey, he reminds us that some of the most important lessons in childhood that kept us safe and have allowed us to strive and thrive as leaders may show up again to hold us back. The hypervigilance that kept us safe as kids, may now inhibit our growth to become our truest selves.
To be honest, I didn’t see that coming.
And it hit me – like a brick.

Radical Self-Inquiry
As leaders reach mid to late careers, some face feelings of uncertainty, fear and unworthiness. Despite accomplishments and income, there seems to be something more to aspire to.
Colonna suggests that we look deep inside ourselves to understand this feeling of fear, unworthiness or self-criticism as we move into greater uncertainty in our lives.
This uncertainty is not abnormal. (that’s right, there is nothing wrong with you if you are feeling this way).
Sure, it may be easy to continue along the path of increased responsibility and title, but at some point, for some folks, it no longer is enough.
A void still exists.
Colonna suggests radical self-inquiry to determine the root cause of these feelings. This self-inquiry can help you make meaning of this discomfort and find your true self that you need to find at this stage in your life.
Some of the questions involved in his self-inquiry include:
- What was the belief system I grew up with?
- How is this showing up for me now?
- How can I use loss of status or change that challenge my self-esteem to find the leader I was meant to be?
- What have you learned about yourself through your experiences?
- Why am I so depleted and exhausted?
- Am I chasing after something that no longer serves me?
- How did my childhood define me?
- Is this definition still true?
- What’s my true purpose – how do I grow and define meaning?
- What do I need now?
- What are the patterns I’ve seen through my life?
- What shows up for you as you reflect upon major moments or inflection points?
- What is enough?
- You are enough
Each question is represented within a detailed chapter in his book.
The Pathless Path
There is so much to discover in this book, but I will keep this focused and relatively succinct.
The concept of the “pathless path” was so insightful to me. Often times, my clients (and myself included) have pondered:
- What is my path?
- What is next for me?
- Why am I not satisfied?
I’m here to remind you, you are no alone if these questions arise.
Colonna, who studies Buddhism, suggests that perhaps that not knowing what is next is possibly the path. Perhaps being lost on this journey is actually part of the path?
<which is great, unless you need to pay the bills Jerry, LOL>
Part of this growth and the radical self-inquiry, is the willingness to sit in the uncertainty and trust yourself.
During this process, you may experiment and acknowledge your true purpose and the “why” behind your leadership.
You are not alone in these feelings of uncertainty and trepidation.
How can we define worthiness outside of job promotions, new titles, higher salaries and better “things”?
Colonna suggests, as we find our true selves, these things are not as necessary to justify our success. He suggests that living with the congruency of our values and beliefs will be enough, and our progress and growth will be enough.
For those of us who cannot see the clear path, feel that we may be broken and do not belong — this book is for you.
The search for Aliveness may be the answer.
Where we no longer live to work, but include meaningful work in our lives.

Your Values: VIA Institute Strengths
Rooted in Your Values
I’ve found that being rooted in our values is so important and helps us reach more peace and balance in our lives. A former coach led me to the VIA Institute Character Strengths assessment as a great grounding exercise.
The VIA Strengths Survey is a free survey that provides a report of your unique 24 character strengths in order. It’s insightful to see the top 3 character signature strengths and how these may show up in your life.
Experiencing these can impact our sense of meaning and sense of happiness.
A few important questions I use with my clients are the following:
- How do your strengths show up in your life?
- How do you feel when you are using these signature strengths?
- Are you surprised by any?
- How might you strengthen any of those at the bottom of your list?
Find a way to engage those strengths during our day to help us feel more alive and engaged.☀️
Here’s a great overview by Dr. Laurie Santos: The Wheel of Virtues from @The-Well


