Startup Life Is Scary, Reflections on My Past Two Years as An Entrepreneur.

Alex Jackson
Sep 1, 2019 · 7 min read
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Photo by Aaron Burden on Unsplash

September 1, 2017, 3:53 am. The loud and invasive tones of my portable radio screamed at me to get out of bed, someone, somewhere needed an ambulance. I worked an opioid overdose that morning on a 19-year-old kid; he would never get to see his family again.

It was time. The concept of starting a technology company had been a goal of mine for the past nine months. I had an idea to use Virtual Reality (VR) as a means of practicing high-acuity, emotionally charged medical calls for paramedics. The goal was to perfect muscle memory and also help prepare for the emotional toll that working in emergency services puts on your mind and soul.

I love the concept of entreprenuerism. It’s energetic and engaging to say your an entrepreneur. I’ve heard some incredible assumptions when I introduce myself as an entrepreneur. You’re successful and wealthy, or you’re going to end up broke and living in your parent’s basement. You’re crazy! Or you must be on your way there.

It’s easy to say, with little opportunity for folks to validate or watermark your successes much beyond what they see and hear, which depends primarily on you. Which brings me to the most powerful lessons I’ve learned over the past two years as young, still wet behind the ears entrepreneur.

1. “I’m an entrepreneur” is easy; being an entrepreneur is not.

I’ve found success in my “why,” my son specifically. My goal for him is simple, grow up to pursue what he wants and be happy and successful in doing it. The metrics are for him to decide upon as he grows, but my responsibility is to facilitate it and make sure he gets every opportunity I can provide.

I would suggest success in entrepreneurship stems heavily from your why, your ability to dig deep and hold onto something much more significant than yourself. The reality is the path is dark, cold, and challenging; its meant to be, anything worth having isn’t easy to get. What’s really interesting is that you learn to love the process as much as the prize.

2. Develop a passion for learning.

Traditional methods of learning, such as registering as a student didn’t work under my new schedule (work, work, work, sleep, gym, eat, repeat). I was forced to expand the way I learn. I started taking online courses and keeping myself accountable for showing up and more importantly, completing the work digitally.

The other part of learning I would propose is the willingness to reflect on past decisions objectively, and utilize those lessons moving forward. I can’t begin to count the number of times I’ve F***’d up over the past two years, it happens and will continue to happen. My desire to learn and my willingness to let myself screw-up and learn from my mistakes has been a tremendous asset in the journey.

Objectively reviewing my mistakes has also helped to improve situational awareness moving forward, a classic case of “I’ve done that dumb idea before, let’s try a new one instead.”

3. Listening, really learning to listen.

“You’ve got two ears and one mouth for a reason”

- My Mom.

Learning to listen has been a life journey and one that I continue to work on daily. Being in business, especially a start-up that I run, I’ve had to learn to STFU a lot. I realized very early in this journey; it was not about being right; it was about listening and achieving consensus to move the team forward.

When I learned to listen actively and started practicing the skill, I had a different takeaway from what people were saying.


Asking someone to confirm what I thought they said was so powerful. It helped alleviate misunderstandings, but also helped to indicate who was paying attention and listening to me.

Listening has been fundamental in keeping our start-up alive and moving forward. I’m grateful and incredibly lucky to be surrounded by a lot of brilliant people with a wealth of expertise. Learning to listen to them, and utilize their input in the decision-making processes has been a critical component to our momentum and growth.

4. Learning to say no.

- My Grandfather

I initially tried to chase every and any opportunity and internalize and utilize every tidbit of information everyone who claimed they knew something told me. It was my hamster wheel experience, and it lasted a while.

Then I learned to say no, or some exciting variation thereof. IT WAS AMAZING! Life changed; I wasn’t in meetings and seminars and conferences and networking galas all the time.

Suddenly, I had time for myself, and I wasn’t spending money on things that didn’t add significant value to my efforts. Learning to say no also brought me confidence, which I’ve found I needed a lot of on this journey. I’ve always felt I was a confident individual but learning to politely and firmly tell people “no,” brings a different level of self-empowerment to the engagement.

5. Time is my most valuable commodity.

  • My Dad.

I get where he was coming from when he used to drop those cheesy lines on me as a kid. He wasn’t wrong, time flies, whether I want it too or not.

Being an entrepreneur has taught me so much, but learning to manage my own time, all 86,400 seconds a day, effectively and productively has been hard. Really hard actually.

Younger, dumber, and ignorant me would have told you I was on top of my schedule. I was always 30 minutes early for work, and I knew when/where/why I had appointments and made them on time. I generally only showed up 15–20 minutes late when I went out for events in the evening (insert cheeky comment about being fashionably late here).

Beyond fixed commitments, my schedule was whimsical, I was working, or I wasn’t. However, there was no dedicated learning time, no morning or evening routine, and no dedicated one-on-one time carved out for my son.

Entrepreneurism taught me quickly that I had to manage my time, and initially, I thought that meant use all of it to work. This behaviour is both unenjoyable, and unsustainable if you haven’t already tried it yourself. I quickly learned to schedule my time, keep my schedule, and spend my time on things that were important to me and my goals (bye-bye Netflix).

Entrepreneurism to me is…

life is not meant to be easy, or happy; life is suffering; therefore, to survive and thrive in life, you must pursue something meaningful, that has a purpose. When you find those moments of happiness, you enjoy them, but they should not be the goal of your pursuits, your pursuits should be something great.”

The concept of enduring suffering for a higher purpose is what entrepreneurism represents to me. An opportunity to embark on this incredible journey I initially thought would be easy, quick, and full of riches, but it wasn’t.

Instead, it’s been an incredibly difficult and trying path thats pushed me to the absolute limits of what I thought possible. More times than I can remember, I’ve been drained and wanted to quit, I’ve been broken and fed-up, unable to pay myself and beyond frustrated I left a career in EMS for this gong-show. My answer, when presented with all of my challenges and setbacks, has been and while continue to be “good.”

The reason I say good is because the growth has been the most potent part of the entire experience. Here I am, still working away, harder, smarter, and mentally more robust than I ever thought possible. I’ve learned to embrace challenges and adversity head-on and not shy away from it. Most importantly, to never quit, even when things are very dark and bleak.

Emotionally I’ve matured immensely in 2 years, and most importantly, I’ve humbled. I’ve learned to enjoy the little successes, and how to regulate myself during the immense and what sometimes feels like regular failures.

I’ve developed an internal process for evaluating failure and utilizing each experience as a lesson learned, not to be repeated, but utilized to influence new future crazy ideas.

I’ve come to realize the value of my most precious commodity, time. Not time working, but the time spent with loved ones playing trains on the floor, or cold beers with close friends over spicy wings and good laughs.

I’ve learned to support others and be empathic to their frustrations and plights. This understanding of others has helped me to develop a new understanding of our need as humans to connect and feel like we “belong.” Developing this understanding has helped me to create that type of experience as a leader.

Entrepreneurism isn’t easy, but it has been the most rewarding experience of life so far. Win, lose or fold, there is a treasure chest of life lessons to be learned and an opportunity to grow and evolve as a person and I continue to uncover new treasures every day.

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Alex Jackson

Written by

Entrepreneur, explorer, life-long student, sharing my thoughts and perspectives on life and all of its beauty.

ExtendNode’s Blogs for Entrepreneurs

We share educational know-how and inspirational stories written for and by founders, business leaders, and investors.

Alex Jackson

Written by

Entrepreneur, explorer, life-long student, sharing my thoughts and perspectives on life and all of its beauty.

ExtendNode’s Blogs for Entrepreneurs

We share educational know-how and inspirational stories written for and by founders, business leaders, and investors.

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