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  • Writer: Matt Heelan
    Matt Heelan
  • Feb 1, 2023
  • 4 min read

Updated: May 22, 2023



What is confidence? Have you ever lost your confidence? Where did it go? How did you get it back? I lost my self-confidence in 2008. In that same year, my wife gave me a compass to help me find it again. On the compass was an inscription that said,

“What lies behind us and what lies before us are small matters compared to what lies within us. - Emerson.”

I used this compass to find my way back to the self-confident person that I was before 2008. Unfortunately, there are several factors that don’t allow some of us to recover from this loss. So what is this mysterious thing that some of us have, many more want and some never seem to be able to get it? What is confidence? We oftentimes believe that confidence is something that everyone either has or doesn’t but that’s not true because confidence is not a fixed attribute. Confidence for me has traveled on this sort of spectrum throughout my lifetime.

The definition of confidence for me is the attitude or belief that I have in myself to be able to do something. I also, over time, have learned to trust in myself that I have the knowledge, skills, and abilities to do something. It also means I can learn new subjects and concepts, rise to new challenges and hold myself accountable if something doesn’t go as planned.

There is also an important link between self-confidence and self-esteem. Self-esteem is the value that I put on myself. The mistake that I made for many years was allowing other people to assign me my own value vs. defining my value for myself. The day that I shifted to caring less about what other people thought of me was also the beginning of my becoming a more confident person. I say to people all the time that the only people whose opinions I truly care about are my wife, my kid, and my parents.

"You wouldn't worry so much about what others think of you if you realized how seldom they do." - Eleanor Roosevelt

Additionally, I could not have pursued a path to leadership and management roles without high self-esteem and self-confidence balanced with a healthy amount of humility and gratitude. I believe that because of the valleys that I experienced with low self-esteem and lack of confidence really prepared me for all sorts of challenges I faced as a leader. In one example, I was able to rely on my own confidence when I had to lead an organization through a crisis that could have caused the company to go out of business.


Also, a number of the entrepreneurs, founders, and CEOs I have worked with have also struggled with self-esteem and self-confidence issues. I don’t know why I always found it interesting that these individuals that had such great wealth, built great organizations, and impacted so many people also struggled to assign their own value and believe in themselves. The lack of self-esteem and self-confidence are not only reserved for certain zip codes or income brackets.


"If you hear a voice within you say 'you cannot paint,' then by all means paint, and that voice will be silenced." - Vincent Van Gogh

I don’t pretend to have some magical advice for you but here is what has helped me:

  1. Understand Neural plasticity. When a person has a stroke the brain begins to restructure or reorganize itself, create new connections, and create new neurons. Keep that in mind when you lack the confidence to learn something new - your brain can do amazing things it just needs you to believe in yourself.

  2. Create a trusted network or personal advisory board. As I mentioned earlier, I rely heavily on my family when I need help boosting my self-esteem or self-confidence. Over my career, I have also built a trusted network. This network consists of people who have gotten to know me over the years. These people have witnessed me as a success and as a failure. We have earned one another’s trust by giving each other sound personal and professional advice. I also make sure that this personal advisory board encompasses many different people with a broad array of skills, knowledge, and experience.

  3. Stop listening to your inner critical voice and remember your greatness. When our confidence is low we may have a tendency to listen to this inner critical voice. I am generally a positive-thinking person but when I hear this critical voice I make a conscious effort to reject it. How? Listen to the words in your head. If you truly examine what this critical or negative voice is telling you about yourself it is typically not based on actual facts. As a former college athlete, one of the proudest things I can say is that my father never missed a single game. After each game, my father would then get the local newspaper and cut out the box scores that would detail my performance. He would then send me the box scores. He always told me that sometimes you need to look at your old box scores to remind yourself of how great you were and can be in the future.

  4. Exercise regularly. I have always understood the value of exercise as an ex-athlete but as I have gotten older the value that it has on my own confidence and mindset is undeniable. There is also a relationship related to (1) in that exercise prevents neuron loss in the hippocampus and increases new neuron formation. I need all the help I can get.


If your confidence is low reach out to me and I would be happy to help in any way that I can. We can start with your box scores. matt.heelan@thaystack.com

  • Writer: Matt Heelan
    Matt Heelan
  • Jan 20, 2023
  • 3 min read

Updated: May 22, 2023

In 1997 I was at the Kansas City Airport, I was getting ready to board a plane for a business trip and I needed something for the trip to read. I picked up the April/May issue of Fast Company magazine. On the front cover in big bold letters was the word, “Change.” I quickly identified with the content because I had just been promoted to manager and the company was experiencing explosive growth.

I can recall reading the entire magazine from cover to cover before I ever landed in Florida. There was a specific article called, “The 10 laws of Change” that seemed to describe what I was feeling about the changes personally and also what the company seemed to be experiencing. Also, in 1996 John Kotter published his book called “Leading Change” where he looked at several companies' efforts to transform their organizations. John concluded that there were eight steps to transform your organization:

  1. Establish a sense of urgency

  2. Forming a powerful guiding coalition

  3. Creating a vision

  4. Communicating the vision

  5. Empowering others to act on the vision

  6. Planning for and creating short-term wins

  7. Consolidating improvements and producing still more change

  8. Institutionalizing new approach

The question is not only how the transformation will work but a more basic question that I had was understanding why we needed to change the organization. If you look at what changes in our daily, monthly, and yearly lives and business you can look at these factors:

  • Social-Demographics (People/Society)

  • Competition/Substitutes

  • Economics/Ecology

  • Political/Regulatory

  • Technology

  • Industry/Suppliers

  • Customers/Consumers

In Systems Thinking there is a concept called, “The Iceberg of Change" or "Theory of Change."


This concept explains that when you are going to change any system there are four elements that come into play. 0.1 Content. The content of the change; the change-related tasks and goals. 0.2 Processes. The process of change; is how we carry out tasks and meet our goals. 0.3 Structures. The structures or frameworks within the content and process operate; the arrangements we must set up to manage change. 0.4 Culture/Commitment. These are the values, assumptions, or beliefs that we have.


In most organizational change efforts we focus on the things that we can see which are those that are listed above the water line in the diagram below. The reality of what we should be focused on when changing organizations is that 87-90% of those factors/issues that are below the iceberg. The reality is that as organizations change and grow we should be focused on also building the appropriate amount of processes and structures necessary in order to make these changes. Additionally, we need to be listening to the organization to understand how these changes are impacting our beliefs, norms, and behaviors which make up our culture.



In the original Fast Company issue they talk about people being “Change Agents.” Over my career, I have never really viewed myself as a change agent but in the latter half of my career, I have found that most Entrepreneurs, Founders, and CEOs have hired me for that exact reason. They want my experience and expertise because they had a goal or mission to change their organization in some meaningful way. The change may come in the form of high performance, scaling the business, or using new technologies to create some optimization.


We naturally want to avoid change - we prefer the status quo, with its comfort and familiarity, and stability, rather than pursue change with its awkwardness, uncertainty, and ambiguity. However, we can increase our chances of transforming the organization if we have: (a) a clear understanding of why we need to change (b) a clear structure for change and (c) a framework that helps us manage the change

  • Writer: Matt Heelan
    Matt Heelan
  • Jan 5, 2023
  • 3 min read

Updated: May 22, 2023

Since I began my career in 1995, I have worked for 6 different entrepreneurs/founders. All of these individuals started these companies and have since either sold the company, closed the company or they still exist. I have kept a journal of all my observations of the organizations and the Entrepreneurs/Founders I have worked with. The majority of these notes were for me to be able to learn from the strategies that worked and to be able to learn from their failures or challenges. I recently went back through these notes to understand what some of the common themes were around their challenges. Here are my notes:



  • The technical founder failed to acknowledge how his/her role needed to change for the long-term success of the company based on where he/she was at in the company maturity process. Over the course of time companies, leaders and team members go through a maturity process. Note: I created a maturity assessment checklist and matrix to understand a common way to understand where each company is within that maturity timeline.

  • Entrepreneurs/Founders failed to acknowledge their lack of business acumen and waited too long to hire the necessary people or team. A relatively old book but still some relevant content around this topic can be found in the EMyth by Michael Gerber.

  • Entrepreneurs/Founders failed to pay attention and respond to trends in the marketplace for their product or service and then lost their competitive advantage. Think of Polaroid not responding quickly enough to digital transformation. Note: Although there has been a resurgence as the old is now new again.

  • Entrepreneurs/Founders lack the ability to leverage or learn from their network/community. When the business is struggling, his/her unwillingness to rely on their network or community for help. I think if you are willing you can find your community of executives who have already lived through some of the challenges you are facing. I always find it surprising when I still talk to CEOs who think they are the only ones that can solve their issues or problems. The organization and maybe your board may not tolerate this approach or attitude.

  • Entrepreneurs/Founder's inability to think strategically about innovative ways to grow the business beyond traditional methods. (new markets or new applications of a product or service). I worked for this company that built software for the fintech world. They had one product that they kept iterating around but the idea of building anything else for a different industry or selling services around that product was just foreign to the leadership team.

  • Entrepreneur/Founder failure to hire competent executives and leadership team members. Also, inability or unwillingness to fire incompetent executives or leadership team members. The old term is “hire slow, fire fast.” I have witnessed more damage done by CEOs to their own organization because they were unwilling to fire underperforming leaders. Conversely, I have observed senior leaders unwilling to pay top dollar to executives that could take their company to another level.


  • Entrepreneurs/Founders ignored or did not understand how to build a culture of excellence. Yankees vs. Brewers. The Yankees have won 27 World Series titles. The Rangers, Padres, Brewers, Mariners, Rockies, and Rays have never won a world series. I have worked for companies that were considered the Yankees of their industry and the culture was so distinctly different, expectations were high from each other, and being really good was always a lot of fun.



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