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Confessions of an Entrepreneur - Loneliness

Confessions, EntrepreneurLesley PocklingtonComment

When you're an entrepreneur, working on your own can get lonely. It’s true. Especially if you work from home. It doesn't have to be! Here are some tips to combating the entrepreneurial blues and places where you can cowork with real-live people in Toronto (and beyond).

Cultivate an Entrepreneurial Community

Whether you join an existing group, or surround yourself with a select group of fellow entrepreneurs; they're the ones who will understand the feeling of loneliness. They'll also appreciate and respect the challenges and dedication it takes to run a business on your own. Connecting with fellow entrepreneurs is a positive way to feel like you're in it together, and you'll be able to support and learn from each other as well.

That said, it's important to prioritize those relationships. You can't be friends with everyone, so don't try. Invest in good relationships and friendships. You only have so much time. Make it count. How does the quote go? “Leave the table if love (or respect) isn’t being served”. Doesn’t that go for a lot of things in life? Edit.

Take a Break

While your hustle is not in vain, don't forget to take a break every once in a while. Entrepreneurs are busy people, but remember to do other things you love too. Yoga, getting outside, traveling, reading, hanging out with friends. Whatever it is you need to decompress, is important for your mental and physical health. Recharge and come back feeling less lonely after connecting with your world again.

Work with Others

Finally, a lot of entrepreneurs that work solo, also work from home. Get out of your physical comfort zone and work in a coworking space. You'll connect with other entrepreneurs (socially and professionally) as mentioned above. Below are some of the best places to set up a workspace for a day, or on a regular basis in Toronto. They all offer flexible types of memberships, plus events to help you get out there and crush those goals.

Make Lemonade

326 Adelaide Street West - 6th Floor

New to Toronto is Make Lemonade. A workspace dedicated to women. The design-forward coworking environment is tropical and bright. It's a space meant to inspire and support, with strong coffee at the ready and spaces that include board rooms, phone booths and even an outdoor patio. They encourage a community of women to make some magic and get sh*t done! Make Lemonade also offers events for female entrepreneurs from goal smashing to self-care for startups. Photos from Make Lemonade.


Multiple Locations / Multiple Cities

Need a space to breathe between meetings? Or, maybe you need a space to host a meeting (small or large group). Breather has various locations around Toronto and in other cities like New York, Boston, Ottawa and Montreal where you can set up shop for a few hours, or a whole day. The spaces are beautiful and welcoming. Just think of it as an Airbnb for office spaces. Photos by Breather.

Love Child Social House

69 Bathurst Street

Love Child is a coworking and social space for entrepreneurs, creatives, events, workshops, and nightlife. They believe collaboration is the real mother of invention, so they created a workspace designed for connection. With memberships that include social events, you'll never feel alone in this fun space. Photos by Love Child Social House.

We Work

Richmond Street and Bloor Street

The global coworking chain has cropped up in Toronto with locations on Richmond and Bloor. Featuring a cafe, group and individual work areas, this dynamic space is well-known around the world for being a comfortable place to set up shop. With a focus on humanizing work and helping you grow, they've thought of everything. By grabbing a membership you'll be able to set up in a familiar space no matter where you are (almost, there are 59 cities). Photos by Toronto Life.

The East Room

50 Carrol Avenue

Located in Toronto's East End, the East Room offers a stunning coworking space with services catering to freelance creatives and small businesses. Packed with curated antiques, this space is perfect for photo shoots (or just feeling inspired), individual and group spaces, mail services, etc. Membership applications vary offering a more casual workspace to something more permanent. Photos by The East Room.

Confessions of a Entrepreneur

Confessions, EntrepreneurLesley PocklingtonComment
  Confessions of a Entrepreneur by Swell Made Co.

Confessions of a Entrepreneur by Swell Made Co.

We all have pivotal moments in our lives. Ones that set you on a trajectory without intention, but force you (or at least encourage you) to take action. While it was a gradual process, it started in my early twenties. I was fresh out of University and employed at my first corporate job. I was a graphic designer at a marketing company in western Canada. I'll admit, I was hugely naive. Who isn't at 22? I still had a LOT to learn, but I was "good" at my job.

I cringe when I remember sitting in a lunchroom with my boss and co-workers. We were tossing around casual jokes and conversation. I don't even remember what the topic was, or what I said. Then it blindsided me. My boss, in a deadpan tone, called me stupid. Not once, but twice. This person was going through a rough time personally, so I'll give them that; but from that moment forward I vowed to never work in that type of environment again. The corporate world had revealed its true face and it wouldn't be the last time (because, that's reality).

I've endured far more devastating comments and events in my life. Being called stupid is rather petty. I get that. However, that comment from the mouth of a respected mentor/leader haunted me for years. It directed me on a course that has simply allowed me to "do good work, with good people" on my own for the past decade. For that, I am very grateful.

Not all workplaces are toxic. I have had hugely enriching experiences from being employed accross Canada; but if you've experienced one or a few of these environments, you've probably thought about going out on your own too. Thankfully, the definition of work has changed drastically and there are countless opportunities to define and create what work looks like. The majority of my daily interactions are with people who are living a entrepreneur life, or making the leap and it's truly inspiring.

I'm no expert. Truthfully, I'm always learning and figuring things out. Aren't we all? Here are a few lessons I've learned (sometimes the hard way) from being a entrepreneur I'm sparing you with the logistics of making the transition. There are loads of articles and books out there to help you out. Plus, it really comes down to you, and how you design that transition. Gradual or quick, there's no right way.


Life is short. It really is. Taking any type of shit from anyone is NOT worth your valuable time (more about time coming up). Sh*t pay, sh*t work, sh*t attitudes, sh*t offers, sh*t hours. If you smell sh*t, walk away. You are so much better than a pile of sh*t. That goes for anything in life. Phew! Got that one? I'm trying to be as clear as sh*t. I promise, I'm moving on to more enlightening and serious content.


You will meet a plethora of wonderful people throughout your career. You were brought together for a reason. Nurture those relationships well beyond your given time together. It will serve you well. As a entrepreneur, the majority of your work and inspiration will come through connections you make throughout your career (employed or solo). Thriving and respectful relationships will open you up to collaborating with talented and smart people, just like you. If a relationship feels sh*tty, refer to the tip above.


Kindness matters and goes a long way. It doesn't cost a thing to be kind. Don't take shit, but be kind even when it's hard. When good (and bad) things come your way, be grateful for them. See the value in experiences big and small and express gratitude. It helps the world make sense.


Don't stop creating. Whatever creating means to you, (writing, beer making, cooking, photography, painting, designing, etc.) just keep doing it. In your career, you'll go through a body of work and some of it will be sh*t, trust me. Keep working HARD. The more time you invest, the better you'll become and one day you'll find your way. You'll find yourself. You have talent. Don't give up. This quote by Ira Glass helped me through the creative process years ago. I still repeat it when I hit a rut, as you do. Grit and hustle really do go far.

Nobody tells this to people who are beginners, and I really wish somebody had told this to me.

All of us who do creative work, we get into it because we have good taste. But it's like there is this gap. For the first couple years that you're making stuff, what you're making isn't so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.

But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you're making is kind of a disappointment to you. A lot of people never get past that phase. They quit.

Everybody I know who does interesting, creative work they went through years where they had really good taste and they could tell that what they were making wasn't as good as they wanted it to be. They knew it fell short. Everybody goes through that.

And if you are just starting out or if you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you're going to finish one story. It is only by going through a volume of work that you're going to catch up and close that gap. And the work you're making will be as good as your ambitions.

I took longer to figure out how to do this than anyone I’ve ever met. It takes awhile. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.

- Ira Glass


Time is your most valuable commodity. Guard it fiercely. You will always find ways to make money. After all, you're smart and full of ideas. You CAN'T get time back. Spend your time wisely. Personally and professionally. Edit, edit, edit.


Success is a subjective and nuanced thing. Don't worry about what anyone else is doing. Just focus on what success means to YOU. You have an opportunity to create your OWN reality. Define what that means and take the steps to make it happen.

For me, success means doing good work, with good people. I do what I love with equal amounts of discipline and flexibility. I make time for my career/personal passions and for my family. I learn something new every day. Over time, that definition will change and I will continue to adapt. So will you. It's part of the process and life of a entrepreneur, but worth every enriching moment.

That's all I got! Keep it real and work hard. If you're a entrepreneur, does this resonate with you? What else have you got to tell me? I'd love to hear what you've learned.