On trading security for life as a solopreneur

And how I knew it was time to quit my day job...

A little inspiration, a tiny bit of rant, and a whole lot of real talk for you.

Jill Clark photo Kananaskis.jpg

As a full-time work-at-home solopreneur and writer, I've heard the same few questions over and over again. A popular one: How did you do it?

It's something that has been on my mind lately, especially as we transition into fall and I pass the 3-year mark of life as a solopreneur; the past 6 months 100 percent self-employed. Living in the moment, it's easy to criticize myself for not reaching my highest goals yet. When I take a step back, my progress is obvious. How did I get here?

First things first: I spend a whole lot more time exploring my Rocky Mountain backyard now that I schedule every single day for myself.

Slow and steady wins the race (sometimes).

I'll admit, it took me longer to harness the courage to quit my day job than it should have. I eased into it, slow and steady. I've realized that's okay.

A bit of context: This post is also brought to you by current marketing tactics. Lately, I feel like I've heard story after story of marketing media explaining how John or Jane quit their day job to make millions online in less than a month. But don't worry! John and Jane claim you and you and you can do it too if you opt in to their exclusive offer that expires tonight. Gift-wrapped happiness courtesy of the internet.

Queue anxieties. Thank you, social media.

I'm not saying it's impossible to make millions overnight. What I am saying is that building a personal brand, genuine connections, and subsequently a life as a successful solopreneur takes work over time. I am also saying that time is different for everyone.

Let's take a step back.

Three years ago, in a little apartment in Montreal...

I finished university. I packed my downtown London high rise apartment into a few suitcases then squished those into my parents' car. They drove 720 kilometres to Montreal to drop me off smack in the middle of the Plateau: my home for the next year. We promptly learned that you can't turn right on a red in Quebec (and have the ticket as proof). I only spoke a few words of French, and I didn't have a job lined up. I did have a freshly printed Bachelor of Arts and dreams of a big city.

I lived the cliché of an arts graduate. I started by working in a restaurant, and taking as many freelance writing assignments as I could cram into my free time. I applied to publications that weren't hiring. I heard back from some, and used that experience to find more opportunities.

I balanced exploring my new city and learning my craft.

If that meant waking up at 6am before putting in a full day on my feet, I woke up early. If that meant staying up late trying to at least finish the first draft of a story before falling asleep, I stayed up late. After about six months, I was able to work full-time from my laptop.

A year later, I moved again. I landed in Calgary this time. Unfortunately, while remote, most of my jobs were Montreal-specific. Because I love my financial safety net, I donned my arts graduate nametag and found another restaurant job. While it was only a couple days a week, it added a sense of security as I found my creative place in another new city.

Jill Clark photo Kananaskis Country Fall.jpg

But when is it time to quit?

I can tell my own story, but I can't decide for you.

What I've learned: stay inspired and stay on track. Don't fall victim to the overnight success stories, or the gift-wrapped happiness sold at a discount online. Instead, examine your values, define your strengths, and set goals to light the way.

There is no magic number. You can't save X amount of dollars, or have Y amount of clients knocking at your door. You have to decide for yourself when it's right. I could have quit my day job years ago, but I've never been a risk taker. I had to be absolutely sure that I could make it work. I had saved enough to maintain my standard of living for 6 months if I made zero-nadda-zip money.

Although that might sound responsible, it can also be limiting. You don't need to save enough for 6 months, or 3 months, or even 1 month if you have the drive to learn to fly when you feel like you're falling, as long as you also have the knowledge to walk the walk. You can do it if you think you can, not because you bought the secret to success from someone else who claims to have cracked the code. I needed the financial buffer. You might not.

But really. How do you know?

Money worries aside, I knew it was time to quit because I felt it. I mean physically felt it. I felt a pit in my stomach while getting ready to leave the house, even though I was only leaving a couple days each week. My mind couldn't rest because I knew I had deadlines to meet, but also 8 hours to clock before I could get back to the work I actually wanted to do.

To clarify: I didn't hate my job like the traditional story goes. I had it lucky. I loved my day job. I worked in the service industry for 10 years through high school and university. I actually loved it. 10/10 would recommend working in restaurants as a young adult. It's social, exciting, and some days it's a work out if you don't have time to hit the gym. It teaches you what hard work looks like.

Plus, I thrived talking to people every day. I loved helping them have the best possible experience at whatever establishment I was currently working at. And the money didn't hurt either.

When stress replaced the excitement I once felt in a shift, I knew it was time to jump into my lifelong career. When I felt exhausted from working before and after work, I knew it was time to leave. When the rush of the industry only distracted me from my long-terms goals instead of motivating me to work for what I really want, I left.

I always knew I needed more. I'm not sure when I decided I would be a writer (probably around the time I first discovered Carrie Bradshaw because I won't deny that I am a millennial with big city dreams), but I always knew that was my end goal.

If you take anything from my story, take the mindset that risks are okay if that aligns with your personal values. Playing it safe is okay too. The when, where, and how are up to you if you know the reason why you want something.


Are you a solopreneur too? When did you know it was time to quit your day job?

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