The Active Work of Imagining Your #DreamJob and Entrepreneurial Career

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I decided pretty early in my University degree that what I was studying was not a good fit for me. Much to the dismay of my parents, who immigrated to North America in early 2005 from Nigeria with myself and three siblings, I realized in the summer of 2015 that I was not passionate about my degree in Mechanical Engineering. I had just completed (more like barely survived) my first year with average grades, a sub-par experience and was really struggling to find what would stimulate my 19-year old mind.

I vividly remember getting an email from one of our Engineering advisors while sitting in class during my second semester of my first year. The job opportunity was to work in the Student Experience Office as one of twelve Summer Orientation Leaders – current students who would be responsible for welcoming first years and their families through a series of guided tours, presentation and Q+A sessions run by the University, while also having a specific portfolio within the office that would help us enhance certain professional skills based on our portfolios. At this time, I was just starting to explore my interest in business and was instantly attracted to the Digital Marketing and Sponsorship portfolio. At that time, my part time job was packing carts at Costco and although I was loving the free membership that came with employment, I was ready for a change. 

Fortunately,  my application was successful and I started working at SEO in May 2015. That was the starting point that would then lead to several positions within that office, ultimately giving me the chance to lead the sponsorship and partnership efforts for Carleton’s Fall Orientation (FROSH) program, transitioning into an executive positions with the Carleton University Students’ Association (CUSA), and become a member of the Venture for Canada 2019 Cohort. 

Although I don’t currently run my own business, (a goal I’ve held for myself for quite some time) I believe that each of these experiences shaped my definition of the word ‘entrepreneurship’, and helped me develop some of the most important skills that I attribute to that word.


My Personal Experiences (I should have made a Vlog Channel)

When VFC’s Training Camp wrapped up at the end of June 2019, I tried to cram my schedule with as many interviews with Toronto-based start-ups as possible. I decided that after ten years in Ottawa, it was time to move on to a big(ger) city. Eventually, I found an entry-level sales role at Planswell, was inspired by the company’s mission to increase the financial health of all Canadians and joined the 50-person team in August 2019.

The first thing I learned is entry-level sales is a freaking grind and without buying-in and taking ownership of your work, it’s very hard to be successful. And so, I bought in and bought in hard. I also learned that working hard gets you 80% of the way to your goal. 

Being fresh out of school, I didn’t have all “right lines” to say to close a deal, I had just started learning sales theory, so I focused on my inputs (dialing, texting and emailing as many people as I could.)  My first three months were going well, I was seeing results and getting recognition. And then, kind of suddenly, we ceased operations.

I remember the day we got the news in an impromptu town hall meeting and questioning why I had abandoned a relatively safe major for the rollercoaster world of start-ups. Was I in the right city? In over my head? Was this being courageous or careless?

After a couple of days, I was back on the VFC job board, LinkedIn, Slack channels – whatever it took to get into a new role. I can’t say that I had or have the answer to all those questions but being able to learn from my experience at Planswell and take that into my next company was all that was on my mind at that point.

Entrepreneurship does not mean you have everything figured out, sometimes it feels like the literal opposite, and that’s okay. New challenges arise every day and sometimes things get so difficult that it can be overwhelming. For anyone who reads this, I’d summarize the main takeaways as:


  • Thinking things through as a combination of inputs, processes and outputs.

  • Entrepreneurial skills are developed by putting them into practice. There is no master course or quick way to learn.

  • Be courageous enough to take leaps of faith, aware enough to learn from potential failures and content enough to celebrate successes.

  • You do not need to have launched a business to practice an Entrepreneurial mindset. 


By no means do I have it all figured out, but from my story below you’ll see how I got here.. I’m definitely still on the journey myself. Maybe one day, I’ll end up being the successful entrepreneur I’ve always dreamed of being. And maybe, I never will. 

But hey, at least I’d have learned something. 

My Early Misconceptions of an Entrepreneur  

I used to believe that a person who did not have their own successful business could not be an entrepreneur. I did not care about how many of the buzzword entrepreneurial characteristics an individual demonstrated (grit, hustle, grind, hunger…you know the ones).

If you had not started a successful business, you could not mention the word entrepreneurship to me and hope to keep my attention.

This perspective came from my early interest in business after deciding that Engineering was not my end goal. After my first role at the Student Experience Office, I fell in love with student business conferences and quickly romanticized the idea of being a founder for the sole purpose of wanting to be characterized as an entrepreneur. I kept a list of day-to-day problems that I encountered and possible profitable solutions in the Notes app on my iPod Touch. I made the words of founders like David Segal (David’s Tea) and Ethan Song (Frank and Oak), who I got to see speak, my business bible and was discouraged when I could not think of any idea that was sensible or feasible enough to turn into a profitable business.

One of my present-day mentors, Alyshahn Kara (CRO @ GooseChase Adventures) constantly challenges me to change my thought process when faced with work-related challenges, which I know understand as a concept applies to an entrepreneurship mindset. He always talks about thinking about the input, process and then the desired output. As young adults, many of us are guilty of thinking solely of our desired outputs and become so fixated on end goals, that we forget about the inputs and processes that are required to get there. 

We (I doubt it’s just me) think of outcomes like “running my own business” or “become a Director of Revenue.” Although these are extremely impressive and achievable goals, it’s important to take a step back and think about the input and process required for each of these.

In hindsight, this was a subconscious mindset change that I made in University, that has shaped the way I view entrepreneurship today.

While starting a business is the output that I’m striving for, there are many steps that come before that could begin the shaping of the entrepreneurial mindset. The biggest qualities or skills that can create this mindset is the courage to take on the unknown and the responsibility to face the challenges that might come as a result. With each of the decisions that either I have made so far in my extremely short career, there has always been a choice of either betting on myself or playing it safe.

The upside in making a bet on myself has always outweighed the possibility of failing. 

There is always a takeaway from having that level of courage — be it an enlightening lesson learned or a sweet commission cheque. I believe that’s the gamble we take as entrepreneurs.

My Interpretations of an Entrepreneurial Mindset

In the final semester of my university degree, I was excited knowing that I would be spending my summer at VFC’s Training Camp at Queen’s University with 80+ other young professionals who shared my interest in the start-up world. At this point, I was only three courses away from completing both my major and minor and a couple months removed from wrapping up my term as President of CUSA. That academic year was a challenge to say the least (not jealous of the shoes some of you are in right now). 

Taking on the responsibility with five other student leaders to lead 27,000 undergraduate students with no guarantee of success and accepting the consequences no matter what. At that point, my time at CUSA had the greatest impact on cementing skills that I believe are extremely important to my present-day mindset — courage and responsibility.

Courage, in the context of my experiences, having no fear of the unknown or disallowing fear or nervousness to rob me these certain life-shaping experiences. Responsibility is being able to accept the results of those experiences —being able to celebrate the successes that might come or learn from the potential failures. Either of these values can be shaped regardless of where one chooses to start or build their careers. 

These are not experiences that are purely unique to start-up environments, but start-ups do provide a certain level of exposure that I find extremely attractive especially for recent graduates.

After finishing up my term at CUSA I felt “ready” to throw myself into the Fellowship Program, thinking that I was ready and fully equipped for everything that was to come. 

A year removed from that point in time, I now understand that the learning never stops. There’s always more to learn. 

And my experiences across three start-ups has been the ultimate teacher.


David Oladejo is a 2019 RBC Honorary Fellow recipient, and a 2019 VFC Fellow. David is the Sales and Operations Lead at Upsiide, a division of Dig Insights. He studied Mechanical Engineering with a Minor in Business at Carleton University. He is interested in writing about figuring out life post-University and the importance of being a member of multiple communities.

Be courageous like David. Be a Fellow.

David Oladejo is a 2019 RBC Honorary Fellow recipient, and a 2019 VFC Fellow. David is the Sales and...