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  • Writer's pictureKayla Droog Consulting

What I’ve learned on my entrepreneur journey (so far)

Today's going to be a little bit different than my usual content. Today is more of a story time. 

I'm going to tell you the story of my brand, where I come from, how I happen to be here doing what I do and running this business, and what I’ve learned so far. 

So if you don't know me, this is going to be a full introduction for you! And even if you’ve been following me for a while, I guarantee you don’t know my full story!

if you're not familiar with my company, it’s called Kayla Droog Consulting, and we support small business owners with back-end tech setup, systems, and automation to make things run smoother, to take tasks off their plate that they don't need to be doing personally, and to reduce the stress of growing and running a business. But I did not always do this, as you might imagine. 

Listen to the audio:

How I got started

So where to begin this story? Well, if you had told me 10 or 15 years ago that I would end up being an entrepreneur, I would probably still be laughing, because I never thought that this is what I would be doing with my life. But I'm so happy and grateful that this is where I ended up. 

I have three sisters, and if you had asked our parents when we were growing up which of their four children would end up being an entrepreneur, I guarantee that my name wouldn't have been at the top of the list! Not that they wouldn't have thought that I was capable, but they wouldn't have thought that this was the direction that I would choose to go. 

Being a business owner has a lot of risk. It doesn't always have stability. You have to be a bit adventurous. You have to trust the process sometimes. As a recovering perfectionist, sometimes these things are hard for me to do! 

I'm not going to say that it has been easy. It definitely hasn't! But it has been a very rewarding experience. 

If I look back over things that have happened to me in my life, I think that some of this entrepreneurial spirit started when I was 18 years old and I decided that instead of going straight into more school when I left high school, I was going to take a year off and move to New Zealand by myself. 

Yeah, that sound you're hearing? That's my mom freaking out. 

But my parents let me go, and it was amazing. I had never really been on my own before. I had never been anywhere near that far away from home. And I had to rely on myself. I had to figure out what I was doing, and where I was going, and how I was going to take care of myself. 

I did go through a work abroad program that helped me a little bit, but for the most part I had to figure everything out for myself. It was challenging at times, but I also loved it. 

At the time I didn't think that I was doing anything super crazy. But now as an adult, every time I tell someone, "Yeah, when I was 18 I moved to New Zealand by myself for a year." Their response is, "Oh my god, that's adventurous!" And yeah, I guess it was. It didn't seem adventurous at the time, but it was. 

That really started me on this journey of realizing that I don't have to do things the way everyone else does them. 

My education and work journey

Now, it took a while for that lesson to sink in. When I returned from New Zealand, I went to school. I spent six years in school after that. That's a long time to be in school! 

I did an undergraduate degree, I did grad school. I was on a trajectory to have a very organized life. I had a specific plan for what I was going to do, and I was going to become a professor. That didn’t happen. 

I ended up going into the arts and culture sector and worked in that sector for several years at some of the biggest museums and art galleries in Canada.

When you were in high school, did you ever have to fill out one of those aptitude tests to tell you what careers you were most suited for? So when I was in high school I filled one of those out, and according to that evaluation my career in arts and culture should have been my dream job. It hit all the things I was good at. It hit the things that I was interested in. It should have been my dream job. And it took me many years in that industry to realize that it wasn't. 

Two things happened. One, I did not love the work I was doing the way that I expected to. I didn't find the sense of fulfillment in that work that I was looking for. I realized that part of the problem was I never got to see the impact that I was having on people. I knew that what I was doing was important, but I never knew if a child came and visited a museum or an art gallery that I was working at and had a great experience, if that influenced them to go home and study art or history or science or literature. I never got to see my impact. I realized that I personally need that. 

Then the other thing that happened was I spent several years working in a toxic environment and I did not have a supportive boss or administration above me. It really was not a healthy place for me to be. It reached the point in my last year there that I was so stressed out from being in this environment that I started experiencing health problems and I knew that if I did not leave this toxic environment I was going to have some sort of health crisis. So my 30th birthday gift to myself was that I got to quit this job! 

I was so stressed out, so sick, and so anxious that I actually quit that job without having another job to go to. Again, I think that was some of that sense of adventure, that sense of being willing to trust that something better was going to happen for me, because I wasn't willing to just wait around for it to happen. And I was privileged enough to be in a position where I could spend a few months not working if I needed to. 

So I quit that job. I did have to do some other jobs in the meantime before starting my business. One of the jobs that I did for a while after that was I did legal intake for several law firms in the US. People reaching out looking for a lawyer for various things. I would talk to them, take detailed notes on their story, and schedule an appointment for them to talk to an attorney. 

This was a rather stressful job as well in a different way. Every time someone was calling in, they were calling in about something negative, because they were experiencing often the worst things in their life. They were having trouble with custody of their children, or they needed a divorce, or someone had passed away and they were dealing with their estate. Things like that. So these were often not enjoyable conversations to be had. It was very common for people to break down when I was talking to them. It was common for people to yell at me because they were in such high stress situations. I burnt out of that job in less than a year, because just emotionally that was not a good fit for me. 

Deciding to become an entrepreneur

At that point, I had known for several years that I wanted to be self-employed if I could make it happen. I was starting to feel like I did not fit into a traditional work environment and if there was any way I could work for myself, I wanted to make it happen. 

I started a couple of businesses that didn't really go anywhere, and I was getting discouraged because I knew that a successful, full-time business doesn't happen overnight. I was worried that I didn't have what it takes to build a full-time business and work a full-time job on the side, so I didn't know how I was ever going to make it happen, to build a business when I still had to work, because of how much just having to work took out of me. 

This sounds like a very weird thing to say, but COVID 19 was actually lucky for me, because of the government assistance that I received from being laid off and unable to work in the field I was working in at the time due to COVID. I was able to keep paying my bills and create a business. If that hadn't happened, I don't know if I would have the business that I have today. I was incredibly lucky. 

What kind of business to create

I had been thinking for a while about what kind of business I should create. What am I good at? What do I enjoy doing? 

And either the Instagram algorithm read my mind and started pushing ads at me - I guess that's more likely - or the universe was trying to push me in a specific direction. But I kept getting ads about having a virtual assistant business. 

Finally I decided that it made a lot of sense. It was a skill set I already had. Every time I had supported a small business owner in the past, I had really enjoyed it and been good at it.

And it’s definitely a business where you're helping people and you get to see the results, the impact, and the outcome. I decided to pursue it and see where it went.

I ended up taking one of those courses that the ads were pushing at me. I probably didn't need it. I already had the skill set. But it gave me that confidence that I needed to take myself seriously and actually move forward. 

And I did quite quickly. I went through all of the videos and training materials for that course in one to two weeks, and then I hit the ground running. I set up my website and a few other things that I needed. I started going into Facebook groups connected to that type of work, and just talking to people, telling them what I was doing. 

Within a month or so things started falling into place. I got some random “right place at the right time” type of connections. Every time those things fell together, kind of like magic, I felt like it was a sign I was heading in the right direction and that I was doing the right thing.

How it’s going now

I had started off offering fairly general services, because I didn't know what people were looking for or what I could do. Or I knew what I could do, but I didn't have confidence in it. Then again, these fluky things happened. Because of specific softwares and systems that some of my early clients had, I ended up becoming very competent in software that I had never heard of and never knew existed. I started realizing that what I really was interested in, what I really enjoyed doing, was systems. 

My business has really evolved over time. I've had a team for quite a while, and that has changed and morphed over time as well. I have tried having an agency approach. I've tried some different approaches in my business. I realized that I don't want to spend my time managing a team instead of having that client connection. That's the reason why I started my business in the first place. 

So that's where I'm headed right now. Come back in 3 to 5 years and see if my business is even recognizable at that point! But that's one of the things that I love about being an entrepreneur - you get to grow and change, and your business gets to grow and change with you. It's never adult dull moment. And if it becomes a series of dull moments, then you pivot and you change direction, and you find something to get excited about again. At least, that's what I do. 

I hope that this story has been interesting to anyone who's not my mom. I would love to hear about your business journey and how you've gotten to be where you are. Let me know down in the comments or feel free to reach out. I would love to hear from you.



Kayla Droog Consulting supports heart-centered small business owners with the back-end systems setup and updates they don't have time to do, so they can focus on serving their clients and growing their businesses!

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