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My Lone Wolf Journey to Entrepreneurship

by Sandy Wong April 04, 2023 4 min read

My Lone Wolf Journey to Entrepreneurship

For the first 3 years of my business, I did it all by myself.  And it worked fine because I am naturally driven and disciplined.  These are two traits that were engrained in me since I was little.

My parents are of Chinese descent and were the first generation to immigrate to Canada.  Growing up, my dad worked night and weekend shifts at a hospital and my mom was a seamstress.  She went to work during the day and brought bundles of fabric home with her so she could keep working on the weekends.  At a young age, I was taught that working hard was the only way to success and so, when I felt called to start my own businesses, it was never a question of will.

Advantages and Challenges of Being a Lone Wolf Entrepreneur

When I started Rugs by Roo, I took a course about "How to start a drop ship eCommerce store" and away I went.  I was the shop operator, the customer service, the writer, the order processor, the returns department, the shipping expert and the accountant. 

I was loving the freedom and control I had over every aspect of my business.  I loved that I didn't have to get the "buy in" from anyone to make a decision.  I didn't have to manage anybody other than myself.  I felt fulfilled and confident about my decisions, and the sales were rolling in nicely.

And then we got bigger.  1.5 years into the business, we hit a quarter of a million in sales.  The decisions I was making around my business involved thousands of dollars instead of hundreds, which meant that mistakes were more costly.  I was spending a lot of my time researching vendors and software, and getting into territory that I was unfamiliar with.

On the family front, I was now juggling two kids with a third one on its way.  I knew that my capacity would only go down in the next 6 months rather than up. 

Lone wolfing had its perks up until I was ready to scale my business.  I recognized that I was limited in my knowledge and capacity.  I also felt a general sense of loneliness as most of my network of friends were not business owners, and those that were business owners were mostly male.  While male entrepreneurs who were also fathers may understand part of the parent-preneur journey, I was not prepared to discuss with them how hormones, mood swings and mom guilt was a challenge for me. 

Overcoming Challenges

I was pregnant with Daphne when my coach asked me about my game plan for when I had to give birth.  Who would help me with my business during the first month after I give birth?  I realized that I didn't have a plan and I had four weeks to figure it out.

The first person I ever hired for my business was a virtual assistant based in the Philippines.  Ria was brought on to process orders, fulfil orders and then eventually, to answer customer emails.  The challenge was trusting that she would do a good job.  The solution was trusting that she would do a good job.  I realized that one fed into the other.  Ria's confidence grew the more I exhibited trust in her, and the better she became at her job.  It became a game of trust.

The next person I hired was April, our marketing coordinator.  Having been the face of the business all these years, I was worried how that would look from the eyes of the customers.  When I was interviewing candidates for this position, I knew that whoever I hired must have a deep care for our products and our customers, and it must be genuine.  This was more important than any skillset she had on her resume.

April opened me up to seeing marketing through a new lens.  She had her finger on the pulse when it came to understanding our customer behaviours and really knew how to speak to them.  I realized that what I knew as "marketing" was extremely narrow and one sided.  In hindsight, my lone-wolf mentality was cocky and full of blindspots.  This discovery was humbling and a huge breakthrough for me as I saw that my want to do things alone came from a place of not wanting to be accountable to others.  And this was costing me my business.

Pursuing Passion and Purpose

Now, I am obsessed with connection.  One thing that is often shared by Tony Robbins is the phrase "it's not what you know but who you know".  I have surrounded myself with advisors, coaches, mentors, other female business owners and a team of people who are knowledgeable in their fields.  When up against a roadblock or a challenge, my question is no longer "what do I do" but rather "who am I calling".

When I share with people the reason why I started Rugs by Roo and what we are out to accomplish, people get so touched by our purpose that they automatically sign themselves up to be a part of our journey.  They take on whatever it is they feel compelled to take on without being asked.  The self-propelling nature of it all is what makes this journey so beautiful.  What I'm realizing is that the bigger the mission, the easier it is to build.


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