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The Heart of the Leader; Asking the Courageous Question.

Updated: Oct 27, 2023


I received this inspirational gift from someone who was my leader and mentor many years ago. It has been a catalyst for me to rethink many problems, decisions, or ideas that felt mountainous to overcome. It is the perfect reminder of the one thing that can get in our way of pursuing what we truly desire or what truly serves us. Fear.

I was looking at this on my desk, as I do every day. Some days it hits me… answer it! But this day, I began reflecting on the big goals I’ve achieved because of answering. I thought it might be worthwhile to share and reflect with you. None of these were easy. They took soul searching, determination and resilience to pursue. But I've found that answering this question is worth it. I hope you do to.

I Quit! Smoking that is! This was the first big answer to the question. As a 20-year smoker, from a family of smokers, I did not think I’d ever be able to quit. Believe me, I’d tried. At least five times by this point. And because I witnessed both parents suffer from the long-term effects of smoking, I chose the attempt and became determined that I would not fail.

I asked my long-time doctor to prescribe a new drug that helped with quitting. They told me no; it was too new. So, I switched doctors. While going through that process, I learned all I could about what successful quitters did. I found that cravings of any sort only last 3 minutes and that a craving was simply a pathway in our brains that create a habit. If I could get through the 3 minutes with each craving, they would eventually decrease. I used the support of my doctor and the reminder that I can get through anything, for three minutes. It was HARD! I lost focus, I judged myself for being to weak to continue, but I did. I haven’t smoked in 15 years, and I can’t remember the last time I craved one.

I Donned a Cap and Gown! My beliefs in childhood were that I wasn’t college material, nor would I be able to afford it. I was taught to pull up my bootstraps and get to work. I knew that putting in hard work was worth something. But I’d always wondered if I should get a degree.

When people in the workplace would recommend a degree or certification, I had a attitude. Am I not good enough because I wasn’t privileged enough to go to college? Had I not demonstrated that I knew how to do the work and do it well? What I came to realize was that it wasn’t about the piece of paper, it was about what I would learn. I was all in. But I had to do it my way. It needed to fit my lifestyle, allow me to do the work, and to do the most in the least amount of time. I found a program that allowed me to use my experience to gain credits, with what was then a new online program, and I finished my degree in two years. I then pursued my Project Management certification. I felt so accomplished, but moreover I now had experiences and information to help me succeed! Not only did I set and achieve the goal, but I did it in a way that served me best. Plus, my stepson who was 16 at the time gets to tell everyone how he tutored me through college, because let's face it, who really loved their Statistics class?

I Trusted. I’d been working for the same company for quite some time and was not under a new leader for the 3rd time in as many years. I wasn’t getting opportunities and frankly I felt like my skills weren’t valued. I was considering leaving. It was scary and I was not at all sure where I stood. Would I have to start over? Would my bench knowledge be transferrable? Would it matter if I stayed? I had an opportunity to have dinner with a leader from an adjacent team and I decided on a whim to trust and share with them what I was thinking. I didn’t know this person well, but I felt like I needed an outside perspective, and I sensed I could trust them. The conversation felt scary. I was risking that someone would say something, and I’d be on the way out before I knew it. Instead, I received feedback on perceptions, and an offer to transition to a team in which I could grow and learn. I landed where I could make an impact, gain additional learning and lead and mentor others.

I Pursued my Dreams! If you read my website, you’ll know that through all of what I just described, I began to realize, I don’t remember this being the dream when I was 12. I was questioning everything. So, I decided to dream into it and determine what I loved to do. This took several years of questioning and months of thinking, visioning, reflecting. Certainly, there was much of my

career that was joy filled, but how could I be more intentional about that? Coaching presented itself and so, instead of a master’s degree, I pursued a coaching certification, for me. When I was done figured out how to start my own business. You might say, people start their own businesses all the time. True, but I’m at the later part of my career and need to support all the financial obligations that come with that. To paraphrase Frank Sinatra, again, I did it my way. It took me a few years of working full time and in my business. But eventually I created enough that I can now do all the things that I love.

I write all of this to ask you the question. What would you do if you couldn’t fail? How would you do it your way? What if you asked your team this question? Think of the ideas!

I’m hopeful that all who read this will be inspired to put aside any what ifs. I encourage you to answer as if you could not fail. Ask others to join you. Get your own mentors and coaches. Engage your teams to figure out how. Be a courageous leader by asking these questions. I had several who helped me along the way. Including the leader who first asked me the question. Ask and then…. Keep asking!. Look for the purposeful path in the process. As I sit down to do my business planning for next year, I will ask again. I’ll let you know how it goes! Wishing you a joy filled journey!


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