Entrepreneurship Isn’t For Everyone and That’s OK

Today I was on a call with a girlfriend discussing the challenges that come with being an entrepreneur. The last time I was home visiting, I actually had a date scheduled with her and my niece; we had it in the calendar, it was planned and I was excited. As I was en route to her place, my colleague called and said our 12pm call had been pushed to 10am and I had to be on it (it was 5 minutes to 10am by the way). I got on the call, walked into my girlfriends house with the phone on mute and hugged my beautiful 2 yr old niece who was so excited to see her тітка Cleo. I promptly proceeded into her walk-in pantry, where I spent the next 30 minutes on a client call while my niece ran in periodically to show me her “Selsa” drawings (read: Elsa from Frozen) and her toys.


To put this in perspective, I go home to Edmonton once every 8 months or so — and I spent 30 precious minutes of my heavily scheduled visiting time on a work call rather than playing with my sweet babe and visiting with my friend of 20 years. I know it sounds like half an hour is a minor thing, but when I only have two hours of visiting time once every 8 months, 30 minutes is A LOT of time.


I say all of this because something I hear often from people is how “lucky” I am to work for myself, how nice it must be to create my own schedule and how everyone and their dog wants to be an entrepreneur. Let me tell you two things:  

  1. This. life. is. not. for. everyone. AND THAT IS OK.
  2. I am NOT lucky — please don’t reduce this to luck, because that suggests that the culmination of my success is nothing more than fortune, and that is neither fair nor true.

My success was not luck, it was a combination of Serendipity (10%), Likability (10%) and Discipline/Work ethic (80%). 


I want to put a few caveats on this, before we dig in.

  • I love my life.
  • I love my work.
  • I love the people I work with — literally I only work with humans that I have love and respect for.
  • I love being self-employed.
  • I was meant for this life.

I am grateful that I have gotten to the point that I am in my life and career, and I am thankful for every single human who has ever taken a chance on me, or hired me to work with them (shout out to Coco, P, Lissa and every client who has ever hired me). But I’d be lying if I didn’t tell you that this road is hard AF.


This post isn’t one of those entitled complainer blogs. I’m here to keep it real about the challenges that come with owning your own business. I spend a great deal of my time disabusing people of this glamourized notion they hold of entrepreneurship and part of that is my own fault.


It’s Feast or Famine… For Real


Everyone sees the “cool” stuff that I do on my IG stories, and don’t get it twisted, I do cool sh*t and hang out with cool people. But that’s maybe 10% of my life. The rest of my time is spent managing schedules, planning, emailing, strategizing, being in meetings and basically making sure nobody crashes any planes. Thrown in there is a meltdown or two every month for good measure.


The entrepreneurship life is more often than not a constant oscillation between feast or famine and if you’re someone who needs:


  • To know when you’re getting paid next
  • To know the amount of money you’ll make in a month
  • If you’ll be able to pay your rent next month…
  • That you have benefits like dental and eyewear…


Then this probably isn’t the life for you, friend. It would be disingenuous of me if I didn’t honestly say that I feel an itty bitty twinge of envy at people who leave their jobs at 5pm and aren’t obligated to answer their email. I miss the days where weekends were a time to rest and hang out.


The thing is, when you’re self employed, if you’re not doing something, you often feel guilty because you could be doing more. It always feels like you should be doing more, because guess what, you have no idea where your next pay cheque is coming from. So we as entrepreneurs very often get into the habit of working into all hours of the day and night in search of this fleeting need to feel productive and like you’re putting in that WERK. And while that is partially my own fault (#boundaries), the reality is that sometimes often you do have to work long hours, cancel on friends last minute and spend your “vacations” (I use that term loosely) on calls in the car or up at the crack of dawn to get emails out of the way.


You Get to Make Your Own Schedule, Cleo!


This one is a crowd favourite: You’re so lucky, you get to make your own schedule.


There is a heavy price I pay for being able to “make my own schedule” and while it means that I get to go home to see my family for a week, or work from home, it also means during that time I am always on call and always working — I don’t get vacation pay. If I don’t work, I don’t make money and I’m not at the point in my life yet where I can afford to take a week off and turn my phone/email off. There is nobody to do the work if I don’t do it and there are no sick days. Again, I know this makes it sound like my clients are mean (they’re truly not, I have the best clients ever). I know if I emailed them saying I was sick, they would absolutely understand and nobody would give me grief, but when your business is in its infancy, the work is there no matter what. If I don’t do it today, I still have to do it tomorrow. Real talk.


Being the Bad Guy is Tough


Another big piece of this and something I’ve learned is a particular skill of mine is having to be “the bad guy”. I don’t mean this in the sense of being mean to people or anything like that — I mean it insofar as when you own your own business, you are responsible for holding yourself and those around you accountable and sometimes that means making the hard decisions. I hate that I am a really good bad guy and I take no pleasure in it. Many of the decisions that I make in business impact not only myself, but my business partner, colleagues, clients and the people who work with/for me; that level of responsibility is scary sometimes and the pressure that comes with it is no joke. I consider myself a fair, reasonable and sound decision maker. I try to make all decisions from a place of reason and never emotion, and always with as much fact based information as possible, so that when I make the choice, I’m confident in that decision. Even with all of that, I’m not immune from the worry that the decision could be the wrong one, and I am hyper aware of the possible consequences of those decisions.


Everyone always wants to be “the boss” ← I hate that term by the way. But not everyone who is in business for themselves is capable of leading and that is okay. If leading isn’t for you, find you a business partner who can lead or work with people who have complementary skill sets to your own. It will make your life much easier, I promise. This leads me into another super important piece of information that will help you immensely if you are journeying down the road of entrepreneurship:


Collaboration> Competition


I would literally scream this from the rooftops if I could. It’s probably in the top 3 pieces of advice I give to everyone who asks me about business. There is enough room for everyone to shine and I promise you, collaboration is almost always the better route. Now, let me be clear, this doesn’t mean handing your ideas over to people for free, not using contracts or doing handshake deals — do NOT do that. But if you can find a space where you can work with other people who compliment your skills, are working towards a similar goal as you, or have some kind of added value, it will make your journey infinitely easier. Not to mention, the more perspective you have, the better. I work collaboratively with a boat load of different people in both of my businesses, because there is no need to reinvent the wheel. Everyone needs help sometimes, and I truly believe in helping people, whether that is in your personal or business life.


*Just make sure your contracts are on lock.


It Ain’t All Bad Baby


I know I’ve spent a great deal of time scaring the shit out of you in this post, but I promise you, it ain’t all bad. Working for myself is by far and away the best decision I’ve ever made, and as the spawn of two entrepreneurs who have been from the top to the bottom (shout out to mom and dad), I am very proud of not only the work I do, but the people I work with and the life I have built for myself. Every single day I am humbled and honoured to still have my businesses and clients — I work with powerful women and men every single day and no matter how tired I am or how stressful the work can get, I would never trade this grand life of mine.


If you choose to embark on this journey for yourself, know that it is the most rewarding and challenging things you will ever do. Don’t be afraid to ask for help, don’t be afraid to make mistakes and always focus on the solution. Problems will always be there, what matters is how we solve them.


Until we meet again my loves,






This post is in dedication to and in honour of the people who have helped me on this journey, I would like to send love + light to each of you. To every soul who has collaborated with me, hired me, helped me when I was in dire straits and encouraged me, I want you to know that I would never ever be where I am without your support.



For You