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Leadership Lessons I've Learned From Entrepreneurship

By: Jessica Takimoto

I was honoured when the QWIL team asked if I would contribute an article to the WILpower blog. Not so long ago, it was my biggest goal to be a leader in the Commerce, and Queen’s, community.

I thought that would mean holding a Co-Chair or President or Director position. I thought it meant being recognized with a community service award or managing a certain team size.

I had a strong vision of what leadership looked like. I have learned that there is a huge difference between holding a leadership position and being a leader.

I run a business called SHINE - a group fitness program based that you can join digitally AND physically (

Throughout this article, I will share with you some of my story and the lessons I’ve learned about leadership over the past 4 years.

When I applied to Queen’s, one of the questions asked, “Describe an experience where you demonstrated your leadership skills. What challenges did you encounter? How did you respond and what did you learn about leadership from this experience?” I talked about my experience as Vice-President of my high school’s student council and how I learned to lead from “behind” because in my opinion, our President did not demonstrate strong leadership skills. My lesson learned was “I have learned that I don’t always have to be ‘in charge’ to lead.”

While writing this article, I dug up my application and re-read it… very full circle and slightly cheesy, I know. Reflecting on not only my leadership experience over the past several months as an entrepreneur, but also over the past 4 years, Grade 12 Jessica had a lot right – and also a lot to learn.

You see, I talked about leadership skills in terms of taking command during meetings, delegating tasks, setting deadlines, and creating plans. This makes sense given this was leadership of a high school club – and anyone who has been on a high school club likely can relate to the difficulty of actually executing on ideas.

The type of leadership position I have now is so vastly different. In the summer, I was a solopreneur in every sense. I taught classes, did the marketing, accounting, sales, and everything else in between. In the fall, I hired a team of 6 instructors, and I now have 3 part-time interns/volunteers helping with business-related tasks – plus a team of 5 Brand Ambassadors. I went from leading my participants in fitness classes to now leading 12 people across 14 positions (and growing soon!).

Needless to say, taking command during meetings, delegating tasks, setting deadlines, and creating plans are essential. It’s what I do – but it’s not who I am as a leader.

I have had the privilege of considering who I want to be as a leader. To me, that means asking myself: what type of environment do I want to create and what type of relationship do I want to build with my team?

And it has NOTHING to do with a title.

I think our system has become obsessed with the idea of leadership. We study it, we emphasize it, and we encourage students to hold leadership positions. Whether it’s a university application or a job application, it seems every administrative body wants to know what leadership positions you have held.

I am grateful for the seemingly endless student leadership experiences the Smith Commerce Society and Queen’s University have provided me. I have held numerous positions, from 3 years on ComSoc Assembly, to 3 years on QLEAD, to the Get Your 150 Initiative, to countless part-time jobs, to leading Group Fitness classes at the ARC. I’ve held front-line positions, done busy work, been a coordinator, and also been a Co-Lead and a Director managing highly sensitive personal and financial information.

Most days, I still feel like a student but in reality, I own a federally incorporated, for-profit business and there is no student government or school administration looking over my shoulder. The governing body is the federal government – and that’s scary! I can say that without a doubt, my student leadership experiences were integral in shaping me into the leader I am today.

Student leadership is like leadership with training wheels. It gives you the autonomy to think about who you are and who you want to be as a leader within the comfort of a student government system. There is always an administrator or body looking out for you and as big as decisions feel in the moment, many decisions have no real-world consequences. It’s a safe space to make mistakes.

I would urge anyone that hopes to hold a leadership position one day to throw yourself wholeheartedly into student leadership. The skills you will learn are not things you can learn from a textbook. Those skills prepared me for leading a team in the real world. Hopefully you can learn from this list, and create your own over the next few years.

1. Being a leader is HARD.

There are no guarantees in life. Especially mid-pandemic, we are living in constant uncertainty. Our brains don’t like uncertainty. I won’t get deep into the neuroscience, but we are hard-wired to want answers and consistency. We don’t want to make mistakes or be wrong, and often this means that we look to others to call the shots.

In my work, I have to make decisions that have real-life impact on my team members – every single day. I know they don’t always like my choices and sometimes it means extra work or inconvenience. I am the first to admit I don’t have the answers. I face being wrong, making a mistake, or upsetting someone with every decision I make. When I call a shot, I take on that risk and that responsibility. I accept that I might make a mistake, and I am 100% prepared to own it. It’s emotionally draining to know your actions have a direct impact on someone else’s life and wellbeing. If you feel that fear, know you are not alone. That’s part of being a leader, which leads into my next lesson…

2. Being a leader requires COURAGE.

Calling shots and accepting the responsibility/risk of doing so requires courage. One of my favourite quotes is, “Courage isn’t the absence of fear; it’s acting in spite of it” (attributed to Mark Twain). Being a leader doesn’t mean you aren’t scared. It means you don’t let nerves stop you from acting.

A prominent recent example that comes to my mind is running in-person fitness. In the fall, my team was running outdoor classes and wanted to move inside when the weather got colder. I was excited, but also terrified. I remember calling KFL&A Public Health, reading every rule online, and negotiating a rental agreement. Someone bringing COVID into a class or contracting it during one of my classes was a very real fear. If it happened, even if it wasn’t my fault, it would be my responsibility. I would face the consequences.

We prepared as best as we could, followed every guideline that existed, and made safety procedures. I was the one who called the shot to say, “we’ve done everything we can to prepare, let’s start”. The fear of starting was worse than actually starting, and thankfully, everything has been fine. As a leader, there will come a day when you are scared to act, and that’s okay. That’s part of the job description. Nothing is risk-free, so do everything you can to mitigate risk, and then just START.

3. ANYONE can be a leader.

Leadership isn’t a position; it’s a choice. It’s waking up and choosing to believe in yourself. It means standing up for what you believe is right – even (and especially when) you are the only one standing. If you are working a minimum wage job or volunteer position, that’s leadership. If your goal is to have a positive impact on every person you interact with, that’s leadership. Leadership is believing you can make a difference, no matter how large or small, with what you have right now. Remember, all change starts small.

In summary, your risk and responsibility may look very different from mine. Starting a business is an inherently risky process. There is far more uncertainty than certainty in my life. In fact, the only things I know for certain are:

· I love my customers, and my customers love SHINE

· I have an incredible team, and I trust them wholeheartedly

· We won’t have all the answers, and all we can do is aim for 1% better every day

If you can’t relate to some of what I’ve shared yet, that’s okay. I try to be as authentic and truthful as possible in what I share in the hopes that one day, they will help you and you won’t have to learn the hard way like I did. I mean, isn’t that the goal of leadership – to pave a path that makes it easier for those that follow behind?

In our digital, disconnected reality today, leadership is more important than ever. I read once that the way to measure the success of a leader is by how many other leaders they create. It’s not a zero-sum equation. Because someone else is a leader doesn’t mean you can’t be too. The more people acting like leaders, the better. I want to see a world where every single person is a leader.

Leadership is like an exponential multiplying function – and it starts with you. Make the hard choices, act with courage, and choose to make the world a little brighter with every interaction you have.

Jessica Takimoto

*Anyone can reach out to Jess on Instagram @jesstakimotofitness or LinkedIn.*


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