Written by 9:40 pm business, life • 2 Comments

Am I an Entrepreneur?

I’d like to tell you about a question that I’ve been wrestling with for about a year now, ever since I started my business, Modern Marketing

“Am I an entrepreneur?”

I think about it every day. I worry about it every day. I wonder if I’m cut out for this. If I have the intestinal fortitude, the strength, the drive, or the talent to be successful. If it’s something that you’re born with, or if it can be learned.

The truth? I’m not a natural-born entrepreneur, hustler, or workaholic. All of which would be great traits to have as a business owner in this hyper-paced world that we live in.

The thing that initially made me ask myself this question was an answer Gary Vaynerchuk gave on the #AskGaryVee Show a few years ago…

I know that I shouldn’t let someone else dictate who or what I am, and I’m not, but I figure that I should respect the opinion of the guy who has been around the block and has seen more than his share of 20-something entrepreneurs come and go, and likely knows what he’s talking about. Asking myself this one introspective question may save me a lot of trouble. After all, what if this is all for naught and I’m just kidding myself?

For those who might not know, GaryVee is the CEO of a 600-person digital agency, and a world-class hustler who claims to be the hardest-working person on earth. No argument here. There’s also no debate that I won’t ever be able to reach his level of business acumen. However, do I have what it takes to be moderately successful, or should I pack it up and just go ‘work for the man’?

Why do I even want to be an entrepreneur?

I can’t sit in a classroom or work for someone else. I mean, I can tolerate it, and have in the past, and perhaps will again in the future, but it’s makes me miserable. I’ve taken good classes or had good jobs over the years, but either way my mind is constantly thinking of all the things that I could be doing instead of listening to a lecture or working that day job.

Even if owning my own business means more work and less pay than a routine 9-5 job, I’d prefer to do it for the flexibility and work fulfillment that it offers. I doubt many bosses would move things around to let me take my dogs to the woods on a beautiful day, take a week off on short notice, or give me fulfilling work that I enjoy. Not to mention, even now I have an enormous amount of pride in myself that I’m doing my own thing, even though it’s not successful yet. Entrepreneurship offers these benefit, if I have what it takes to make it work.

Arguments against

I’m historically lazy. I do attribute this at least partially to a health issue growing up, but my actions over the years leave little room for debate… Growing up and into the early years of adulthood I was known to sleep late, play video games all weekend, and not go the extra mile on almost anything.

I have to sleep eight hours a night. A mentor of mine once asked me, during a time when I was really struggling with my hustle and drive, “What gets you out of bed in the morning?” I knew the answer he was looking for, but couldn’t say “passion” or something similar. I thought about it for a minute, then answered “Commitments.” I got pretty down on myself because all of the entrepreneurs I look up to jump out of bed in the morning with that fire in their bellies. I can’t help it, I’m not a morning person. I need eight hours of sleep.

I’ve never sold anything. Selling is business 101. If you can’t get people to buy your product or service, then no one will. Some people grow up selling people’s own garden flowers back to them, and those people are destined to be entrepreneurs. I never traded hockey cards, or flipped things on eBay, or started a business in high school, which has made me question whether I have “entrepreneurial DNA.”

I don’t have a passion. One quintessential part of entrepreneurship is the drive that makes you not mind the late nights or long hours. What fuels that drive is supposedly passion. Marc Anthony said “If you do what you love then you’ll never work a day in your life.” I don’t feel like I have that one calling that I live and breathe, that I want to do more than anything else, that pushes me to wake up an hour earlier in the morning because I can’t bare not working on it. I just don’t have that feeling about anything. Does that mean that I don’t have one of the fundamental ingredients? If I decide to work on something that I only “like,” will I lose interest in it over time?

Arguments for

It’s hard for me to get started from zero, I work best when I build up some momentum. The problem is that as a startup/freelancer, there isn’t always business momentum. My work ethic, productivity, and results have all increased exponentially since January when I made a New Year’s Resolution to hustle. I still have my off days, but 1 is always be greater than 0. It’s hard to break a lifetime of bad habits, but I’m working to improve a little bit every day.

Sometimes people make me feel bad that I want to sleep that much, but now I’m starting to feel more comfortable with that being okay. I don’t have to be like everybody else. What matters is that I’m sleeping eight hours and not ten. What matters is the work I’m putting in when I’m awake, not the time I spend asleep.

With regards to selling, while I don’t think that it’s in my blood, there have been signs over the years from which I deduce that I can sell when I want to…

  • I remember in elementary school a friend and I wrote and drew a comic book or two and sold copies for $0.25, from which we made something like $2. Better than nothing.
  • When I was once short on money I sold my own DVDs at the flea market and made $200.
  • When I worked various retail jobs over the years, both with and without commission, I did pretty well for myself. At my video game retail job, I spoke to one couple about a gift for their son for about an hour… they decided to do a price check next door at Wal-mart. Even though it was cheaper over there, they decided to come back to me because, I guess, I had done a good job selling it.
  • I once came a cross a table in the mall where someone was selling those spiky dryer balls. I was curious and asked the salesperson some questions. Later, when I was with my mother and she stopped at the table, I told her about the balls and made a better case for them than the salesperson did.

I guess for a long time I just expected that I would find or develop that passion. I really don’t have that “one thing,” but maybe that’s okay. Maybe it’s okay to like several things at 75% than just one thing at 100%. I found this video from a YouTuber, blogger, and lifelong learner Thomas Frank, in which he addresses this phenomenon and quoted Cal Newport as saying:

“Pick something you have an interest in, and then go full-bore and try to get as good at it as you possibly can.”

Thomas goes into more detail, but essentially you can turn any interest into your passion by simply getting really good at it. I like to write, I like the internet, why don’t I get better at writing by doing it on the internet, and then create a business writing for other people on the internet?

And that’s exactly what I enjoy, and it’s exactly what I’m doing. I wrote the draft of this post from 9pm-11pm on a Friday night, so I must like enough to do it as a career.


This is something I don’t broadcast, but I’ve been living with my parents since I became unemployed just over two years ago. I lived on my own for over five years, so moving back in with them was extremely humbling. I feel like I could have gone out and gotten another job that would have given me the means to move into my own place again, but once I decided to start my business, I realized that I would much rather live with my parents, in my childhood bedroom, sleep in my childhood single bed, and drive a 16-year-old hand-me-down car, all to be able to work for myself instead of working for someone else.

[Update: about two weeks after writing this post, I broke my phone, and my car, and the person subletting half of my office moved out, all within 24 hours of each other. What else have you got for me, universe?]

I’m learning to curb my spending, because that’s what it takes. I’m also a notorious impulse spender, opting for instant gratification from eating out or being entertained than the long-term benefits of pinching pennies. Even though I always knew the difference in my head, whenever I had got a little money in my pocket I was very short-sighted. Over the past couple of months I’ve been much more diligent. Cash is oxygen, after all, and I’m making sacrifices so that I can breathe for as long as possible.

I work a retail job, and it’s my second priority. As you may have heard in that video earlier, Gary said:

“If you have a full-time job, you’re not an entrepreneur … You may have entrepreneurial tendencies, you may have aspirations to be an entrepreneur, but if you are an entrepreneur, then you can’t breathe having a job.”

This one line is what made me start to question my entire foray into entrepreneurship in the first place. I may be hustling at my business now, but I’ve had full-time jobs in the past. I wanted the steady paycheque, so I settled. Does this mean that I’m not an entrepreneur, period?

The idea is that if you have a 9-5 job, and you work on a side hustle in the evenings, you’re not an entrepreneur. I feel, however, that if you reverse that and your business becomes what you do from 9-5 and your “make ends meet” job is what you do at night, then you are an entrepreneur.

Well that’s what I’m doing… I work at a greeting card store, of all things, to keep the lights on until my business becomes self-sustaining. Trust me, I don’t like it, but I do it, because my business is my number one priority and I have to put as much time into it as possible if I’m going to have a shot at making it work.

I’m bootstrapping my entire business. Well, mostly. When I opened my business’ bank account it came with a few thousand dollars of overdraft that I could dip into, and I did, to pay for rent and internet to get me started. But, I do have to pay back anything I use. Everything else is coming out of my own pocket and/or revenue. I’m not coasting on investors or venture capitalists, I’m making my own money. Am I struggling sometimes? Sure. But there is a lot of pride and practicality in the fact that I’m subletting half of my office space, all of my office furniture is second-hand (and doesn’t match), my computer is four years old, and I made my own website.

I think I surprise myself when my back is against a wall. Maybe I’m not a purebred entrepreneur, but I’m the next best thing. I see something that I want, that wouldn’t exist if I didn’t do it, and I’m doing it. I think the point is that I’m executing, and execution is everything. I’m not just dreaming about it, or just reading about it, or just talking about it… I’m doing it. And even if I don’t make a fortune, I’m going to continue doing it.

So, am I an entrepreneur?

I think I am, but the history will decide if I am a successful one.

(Writing this post has been very cathartic.)

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