4 Leadership Insights from an Entrepreneur

I became an entrepreneur 20 years ago. I was 30 years old at the time and had recently left my career as a medical social worker in order to follow my dream of moving to an island. That move forced me to start my own business. I had both an expertise and a passion for self-care and burnout prevention within helping and healthcare professions, so I decided I would start offering workshops on these topics and my business was born.

There are many things I wish I knew when I started my business.

I have learned many leadership lessons on my entrepreneurial (self-employed) path. I hope the following ideas will have value for you and your own leadership:

1. Work with what you know and delegate the rest.

There is an endless list of things to do as a leader, and there’s often the tendency to try to do it all. However, nobody is brilliant or skilled at every aspect of running a business or leading an organization. You might be good at training, for example, but need help with crafting a vision and mission. Or you might be great at the relational side of motivating people, but need help organizing your time and managing projects.

As leaders, it is important to know our strengths, and to build teams with a diverse set of skills so we can delegate tasks that are better suited to someone else. Delegation is a leadership strength.

2. Work on your business (organizing, planning, growing) rather than in your business (doing the work, serving clients, etc.).

It is easy to get swept away with working in the business, doing all the work that needs to be done. It is truly never ending. However, experience has taught me that it is important to invest time and resources on my business. Working on my business includes scheduling time for things like goal setting, planning, systematizing, and tending to other envisioning and growth activities.

For example, I publish a weekly newsletter as part of my marketing and communications with subscribers and readers. I have an annual newsletter planner where I have monthly themes identified for this content, publication dates, and more. I never used to have this system in place and would write newsletters ad hoc – it was not a priority, which meant they were published inconsistently. As a result of taking the time to plan, I have successfully published a weekly newsletter, without fail, this entire year so far. This is important because I have learned that successful and consistent communication results in increased revenue.

3. Seek Mentorship, Support, & Learning

When I started my business, I had no idea how many highs and lows I would have to survive to stay on this entrepreneurial path. I also wasn’t aware of how isolating it could feel to be self-employed. We have all heard the saying, “It can be lonely at the top,” but I’m not sure what being at the top means. It’s unique for everyone, but the more responsibilities a leader takes on, the more isolated or pressured they might feel.

Over the years, I have learned how important it is to find mentors, seek support, meet with peers, and engage in meaningful discussions that foster growth, learning, and connection as a leader. I am also committed to my ongoing professional development and do a minimum of 60 hours a year of intentional learning through attending courses, reading books, watching webinars, and going to conferences.

Leadership is about taking risks, getting outside of your comfort zone, and constantly asking what’s possible.

4. Be open to possibilities.

When I started my business, I was facilitating workshops on my own. Over the years, however, I have offered my training and facilitation skills to or through other organizations and groups, which was never my intention when I started out. I began doing this because I missed having people to connect with as colleagues and peers.

As a leader, being open to new possibilities – to the energy of “Yes, I can try that” – has resulted in many opportunities presenting themselves and being created over the years. I recently acquired a new business that someone else founded, and when they wanted to retire, I took it over, rebranded, and relaunched it. Growing this business is now the heart of my work in the world. I could not have imagined this happening three years ago, but now I am leading an international association and growing a membership community.


For me, being an entrepreneur has always meant being a leader. I had previous leadership roles prior to starting my business, but that one decision caused me to step up and grow in new ways. Leadership is not just a role – it is a way of being. I have learned that it is about maintaining a growth mindset, always striving to do and be my best, and helping others to do the same. Leadership is about taking risks, getting outside of my comfort zone, dreaming beyond limiting beliefs, and constantly asking what’s possible. I have also learned that self-awareness, regular reflection, and asking powerful questions are key aspects to my growth as a leader.

Pause & Reflect
  • Are there key areas or tasks that you could delegate to others? What is your experience with building a team?
  • How often do you step back from the day-to-day work of your organization and do more macro level strategic planning, thinking, and systematizing?
  • Do you seek regular support and inspiration as a leader? What are some of the ways you engage in your own leadership development?
  • As a leader, what potentially beneficial opportunities are you opposed to? What opportunities are you intentionally cultivating for yourself and others?

For more free resources, visit our resources page.


Lynda Monk

Trainer, ACHIEVE Centre for Leadership

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