Overcoming self-doubt in the entrepreneurial journey

It is not at all times when business leaders are confident of themselves or of the decisions they make. The reality is that there are moments of self-doubt, which can often freeze you on your tracks. We wonder, when such instances occur along the business journey, how do entrepreneurs overcome their weaknesses and move ahead towards their goals?

KHQ Lawyers Founder and Managing Director David Kelly and Lights Lights Lights Director Danielle Mastro reveal how they embraced the experience and used it to strengthen themselves.

“Over the years I have learnt the hard way that my self-doubt is one of my greatest strengths.”

-          David Kelly

Founder and Managing Director of KHQ Lawyers

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For David, self-doubt is not always a bad thing. “It keeps me sharp. It helps me see the other person’s perspective. It saves me from hubris, arrogance and blind faith in my correctness,” he stated. But it was not an easy thing for him to do.

“It took me a long time to get to this point – a lot of reading and even some counselling. Now, I cherish my self-doubt as one of the keys to whatever success I have achieved in my life. If I didn’t have self-doubt, I think I would much more frequently blunder into mistakes by making assumptions and that I would not be at all self-aware or prepared (not that I’m saying I am very self-aware or prepared) for anything,” he reasoned.

Because of that, David has come to accept that part of him and uses it to be more conscious of himself and others. “I have come to love my self-doubt.  Whenever I interact with another person who seems to have no self-doubt, who is sure they are right, who just knows they are right, I see a risk. I see a gamble. If that person is truly right, then great. They can congratulate themselves on their self-belief and their unshakeable confidence. However, if they are wrong and their lack of self-doubt leads them to blunder again and again into the same mistakes, I see a fool and I remind myself that my self-doubt is not my Achilles heel but a great asset.”

“The moments of uncertainty give birth to my most abundant personal growth.”

- Danielle Mastro

Director of Lights Lights Lights

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Self-doubt can happen in different points of one’s entrepreneurial journey. It can occur even to someone who has tons of experience and successes on their backs. Especially at present with a pandemic and economic crisis to face, many people, including business owners, start to rethink of many things, including their views of themselves.

“Let’s face it, amidst the madness of 2020 and the madness of life in general, there are moments when I sit in uncertainty and chaos. In these moments, there is a pervasive and natural tendency to question my skill, my ability, and my belief in myself,” Danielle shared.

She continued, “I will start by saying that I am still a work in progress. But when I face self-doubt, I journal it while doing it beside a soft light and with the scent of Palo Santo to cleanse my space as I write. I write for pages and pages. I dump my often nonsensical thoughts onto paper and as I furiously try to keep up with the pace of my mind, I expose my thoughts and begin to make sense of the stories. This plants a seed that maybe, just maybe, the story I originally told myself has another ending. As the day progresses, the words and memories and moments of journaling surface in my mind and my narrative changes. This process of a mind-shift only works when I create space and time to find and collect my thoughts. Fresh air, breathwork, and some tunes as I walk in the moonlight of the early and late hours of the day help me to find the answers I needed to the questions I didn’t know I had.”

For Danielle, those moments of uncertainty enabled her to grow. “Each time I go to an EO event I take with me the words of Carlos Santoro: ‘What was the ONE BIG THING, the single greatest moment of learning that will stay with you from this EO event?’ Well, some time ago I sat with my EO family under the Leonard French stained glass ceiling of the NGV in the evening (I still have to pinch myself whenever I remember the moment) and I listened to Janine Ellis say, and I loosely quoted, ‘Facing self-doubt and challenge was like taking a subject at University on how to survive a challenge, how to learn about yourself and how to sit in acceptance of the now.’ That was the ONE BIG THING I learned from that night. I have taken that with me in my quest to overcome the moments when I have uncertainty on myself.”

It is a moment of great realisation for Danielle. “Once I make it past the initial reaction of catastrophe, fear and guilt (the list goes on), I write, I breathe, I listen to my thoughts and I study the moments, the feelings and the beliefs. I pass the subject with honours and learn at the very least ONE BIG THING in the university of my life.”

From such realisations blossom swift actions that lead to great successes. “I have introduced the ONE BIG GOAL (OBG) into our business. We collectively set an OBG for each member that stems from a growth point that each of us has encountered in our life. We make it our focus for 3 months and we openly discuss it with the team. It has nurtured personal and professional growth in a way that connects us to our life’s journey in that the OBG is something that we find ourselves, not something that is imposed upon us. It is natural and effortless and the LLL family love it,” she remarked.

What do you do when you experience self-doubt?

If you have experienced it ourself and want to share your story, email us at communications@eomelbourne.org or leave your comment below.