In my freelance business, I’ve learned a lot from my mistakes. This is the story of how it all began.

A powerful influence on me are my parents. They’re two creatives who went from barely “getting by” to thriving. My father,  is an actor who has been in a ton of movies, tv shows, and plays.

Then there’s my mother who has an incredible resume. It includes everything from being a Toronto Sun journalist and running her own diaper business, to contributing her design and grant funding skills to the not-for-profit and social enterprise sectors.

So, I grew up with an enlightened view of what being a freelance business is really like.

But I also had a powerful desire to monetize my passion for putting my creativity to work. When I went to school, and eventually entered the professional world, I struggled with fitting in.

I didn’t seem to be good at much besides writing. What made that even worse is that I live with a disability called Dyspraxia, and most people I’ve met don’t even know what it is.

With that disability, I get lost really easy, am super clumsy and accident-prone, can’t focus when I’m in a high-stimuli environment and have zero spatial skills, fine motor skills, or sense of space/ time.

This excludes me from everything from driving a car, arts and crafts activities, and playing team sports, to navigating my way around everywhere.

It also has other effects too, like being a socially awkward human being around people I haven’t spent a ton of time around.

But my disability’s weaknesses are meaningless when I write.

I learned how to read and write at a slower rate than my peers.Then, it became an addiction.

E.G: I’m often associated with an image of ink stains on my hands, notebook scribbling (and reading).

I didn’t think that running a freelance business was possible…

 The future of journalism is bleak. Then there’s the influence of social media and the internet. This has made it difficult for independent presses and bookstores to survive.

I also remember the early days of the housing market becoming inaccessiable.

When I finished university I was so afraid. I’d heard awful stories about my generation struggling for opportunities.

After submitting more job applications than I can count, I heard nothing.

Then I created a Kijiji ad. On this platform, I said I was for hire. I also advertised my skills. My rate was based on the same jobs I’d applied for (and didn’t get). This triggered a lot of responses.

Because the ad linked to my blog, and some short-term freelance writing projects I’d gotten through pitching editors.This helped get people’s attention and led to a huge number of offers.

I fell in love with my freelance business but felt a sense of emptiness in every other aspect of my life

 I fell in love with the man I’m still with today, bought two custom domains, and wrote for a lot of really great startups, websites, and small businesses.

But I was lacking a conventional business mindset.

They don’t teach that sort of thing in school. But my clients were the first thing to welcome me with open arms. 

Then, I joined entrepreneur-focused communities on and offline.

Then I gained something that more people should have access to:

The ability to learn from other like-minded peoples’ failures and mistakes.

Probably the closest I’ve ever gotten to feeling like I wanted to do something else was the summer and fall of 2017.

Back then, my partner’s surgery led to multiple months of his hospitalization.

Because so much of energy was going into taking care of him, that I was emotionally checked out of my business. Motivating myself to not just get a “regular” job was really hard. Luckily, my family was a huge source of support back then.

When he finally got better, I hired  a business coach. Because I hated my own work.

This helped me get back on track and think more realistically about where my freelance business was heading.

Then, I re-branded to suit my changing priorities. By attracting an equal of ideal and non-ideal clients, I gained a better understanding of what I wanted.

First I eliminated tactics that weren’t working for me from my work week. Then I took self-care seriously, and didn’t answer emails after a certain time.

And I’m feeling optimistic about the future of my freelance business overall

Retainer and long-term arrangements with clients I’ve worked with before started to be discussed shortly before the holidays.

I’m also writing a memoir about my life experiences with Dyspraxia, and am on track for my new year’s resolution of 100 pages by Christmas 2020. Even on days that are quieter than I’d like, all I really need to do is remind myself that good things are currently in progress. And that, to me is a sign of progress.

This post was originally published on my Medium Digest page. If you want to support future articles like this one, view the original Medium Digest version and click the hand clapping symbol.  

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