Being a business owner isn’t easy. There are amazing highs, but the lows are often quite intense as well. Somedays it feels like the problems never stop – regardless of how much success you achieve. The problems just grow, evolve, morph. So we asked business owners if they sometimes wonder what it would be like to just have a regular job and have shared some of the highlights below.

Raven Jackson

Yes, I am generally happier as a business owner—but that doesn’t mean it’s without its doubts or difficult moments. The freedom, the ability to build something on my own terms, and the fulfillment that comes from seeing my vision come to life all bring me a deep sense of purpose. But there are days when the weight of responsibility makes me wonder what it would be like to have a regular 9-to-5 again. Read more>>

Matt/Messy Martineau/Margaret

I absolutely love that I own my business. Prior to starting Messy Productions Canada I worked in the restaurant industry and while I am grateful for the experience, it simply wasn’t what I wanted to spend the rest of my life doing. I have a theatre arts diploma from Algonquin College and I also trained at the Second City Toronto in their improv and conservatory programs. Pursuing a career in acting has always been the dream and I have had some success in that median, but it wasn’t until I started drag that my performance art career really took off. Messy Margaret was born on January 8, 2020 and it’s been an uphill climb ever since. Read more>>

Jerainnie Concepcion

Honestly, I don’t wonder what it would be like to have a regular job again because I’ve lived it. I remember exactly what it felt like, and I have zero desire to go back.

My last “regular” job was in a call center. The kind of place where you wear a headset for eight hours straight, your lunch is timed to the minute, and you’re judged on how fast you can solve someone else’s problem over and over again. I can still hear the constant ringing, the scripted greetings, the frustrated voices on the other end of the line. The repetition. Read more>>

Christie Evenson

Most of the time, I love being a business owner. I get to create designs for clients in an industry that I love and have fun working on the business strategy as well. However, in the last couple of years, I’ve thought a lot about the pros and cons of being an entrepreneur compared to having a regular job. I had been successfully working full-time in my business for five years when my son was born, and while I loved the work I was doing, I felt resentful of my unpaid maternity leave/vacation time and increased pressure to bring in more money to support him. Corporate benefits and a paycheck that looked the same every two weeks sounded pretty nice. So when an opportunity came up that I was passionate about, I took it and worked in a corporate role for a year, running my business on the side. It was exactly what I needed at that time.  Read more>>

Gail Rubin

I have been self employed since 1990, with a few employment gigs since that time. The idea of a regular job repels me now, but long ago, the idea of “security” in a regular job was attractive. My background is in television and public relations/event planning. My last regular job was as a public relations professional for an arcade game/computer game company. That was actually a lot of fun, as I went to a number of conventions in places like San Antonio, Las Vegas and San Francisco to help promote the company’s products.  Read more>>

Jess Kidd

I’ve spent almost 20 years working in different fields to figure out what I wanted to do as a career.

Most of my time was spent in customer service, hospitality and the food/service industry serving and bartending.

There was about a 6 year stint where I even had my own business as a “Jess of all trades” where I would do anything from cleaning and reorganizing to yard work and small home improvements. Read more>>

Roxy Bunce

There are definitely moments I ask myself that question, especially when things feel heavy. I remember sitting in my car a couple years ago, overwhelmed after a long day of navigating stylist dynamics, cleaning issues, and juggling my family’s schedule. I thought, “Wouldn’t it be easier to just show up, do my work, and go home?” The idea of clocking out mentally when I left a job sounded so tempting. Read more>>

Lilli Summers

Do what you love & it’ll never feel like work…I live & breathe by this statement. I’ve had the privilege of knowing exactly what I wanted to do with my life since the age of twelve. Photography felt so natural to me, & not because I thought I was perfect for it, but more like it was perfect for me. We went hand-in-hand, inseparable from the start. Over time, all things visual media (video, editing & graphic design) went under my umbrella of skills, all leading back to my eye for composition & color. I’ve fallen in love with observing people through a lens, connecting with their vision & reflecting their joy & happiness on camera. I cannot imagine myself any happier than I am right now, doing what I love, never feeling like I’m working.  Read more>>

Samone Scurry

Overall, I love being a business owner, but it does have it’s challenges. Because, I have serveral businesses, I may think about this more than I’d like. With my childcare business, It Takes THE Village, I find myself missing the classroom setting and co-workers. I took for granted, the value of being surrounded by like minded people daily. I also miss having a co-teacher to feed ideas off and share those silly moments. Not to mention, Early Childhood Education is a profession of patience and we are all human. Not having support during trying times is something I had to figure out and find a way to cope. Read more>>

Dante

say with full confidence that I am happy working for myself and starting my storytelling business with my camera. In fact this year marks 10 years of my journey ! I started DANTE’S CRAFT with high hopes to make a living taking photos and videos, that was my baseline and if i could accomplish that i would feel successful. I felt entrepreneurship was the only route to consistent happiness. Being an artist my whole life led me to this decision. I had no interest in any other line of work. Im someone who must live only as themselves each second of the day. That alone prevents me from working for another company or field have no connection to. Read more>>

Dr. Kemia

I enjoy being a business owner because it allows me to pursue my passions and turn my ideas into reality. I find fulfillment in creating something of value and seeing the positive impact it has on others. The freedom to make my own decisions and shape my own path is incredibly rewarding. While there are challenges like stress and long hours, the satisfaction of achieving my goals and growing my business makes it all worthwhile. Being a business owner gives me a sense of purpose and the opportunity to constantly learn and grow. Read more>>