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Day 1: The First Day of the Rest of My Life, January 2, 2020

Is this the most over-used picture of a “digital marketing” work station on the internet?

As of January 1, 2020 I am no longer working a 9-5 job. (Actually it was 10-6.)

Instead, I am focusing all my energy on my own business.

This site will chronicle my experiences, challenges and successes as a “solopreneur”, i.e. an entrepreneur running a business completely by myself.

I hope you find what I have to say interesting and worthwhile.

Why Am I Doing This Now?

I have worked my entire adult life as an employee.

I am 38 years old. I began working when I was 16.

From 16 until 21 I worked a summer job as a “building attendant” for the City of Toronto. A building attendant is a job combining customer service with janitorial duties – they let people into public pools and then they clean up later. I was fortunate enough that this was never more than a summer job. It was also (relatively) well paying.

I had my first office job (another summer job) at 22. I worked for an NGO as an administrative assistant.

At 22 I started a Master’s Degree and became a tutorial assistant with the goal of becoming a professor in political philosophy. Unfortunately, the Master’s experience soured me so much on academia that I did not start a PhD program.

Instead, I temped for most of a year – mostly for insurance companies – saving up money for a trip I thought I would never take when I was older and more settled.

At 25 I spent 9 weeks driving around Canada. (Without a cell phone!) While sitting by myself on the shore of Charlie Lake, British Columbia one evening, I decided I would not be able to live with myself if I didn’t write a book about political philosophy.

So, for the next 5 years, I worked as a glorified mail clerk for an insurance company in Hamilton, Ontario while I wrote my book.

When I finished it, I realized I had to properly join the work force. But I was already 30, with a Master’s Degree in an impractical field, with no quality work experience.

A small business owner took a chance on me, hiring me as a research assistant. So for the last 8 years I have worked as an internet marketing jack-of-all trades for this business and some others. I have learned skills I never thought I would learn. And I discovered that I actually really like doing this work.

My business is actually a few year old. I have been doing work on the side for a couple of years now, but the safety net provided by my day job meant that I never really actively pursued clients. Working 40 hours a week in a job you like for a company you like for enough money to live on is not the kind of experience that makes you quit your job to focus on your own business.

But things have changed for my (former) employer and me. And when that happened, it became clear to me that now was the time I had take the leap – to actually prove to myself that I have value to offer business owners and that I can make a living from it, without an office job to pay the bills.

So I gave my notice a few weeks ago, and I worked my last day just before the New Year.

And now I embark on a strange, crazy, kind of terrifying journey, where I have to figure out how to spend my time and where to focus my energy.

I have no idea how to do that.

What Am I Doing?

A number of years ago, the company I used to work for hired an SEO company to help market the business. They charged a 4 digit retainer. For that retainer they provided a little bit of custom content, a little bit of social media marketing for that content a monthly analytics report and a little bit of technical SEO work. (I can’t remember if the technical SEO work was extra. It might have been.)

After a number of months of this, we realized we could do this ourselves. And we did. With pretty spectacular results (millions of site visits a year, a popular YouTube channel, etc).

Small business owners are experts in their business. But they may not be experts in how to market their business, especially online, where everything changes. So they rely on others and pay them to do the work for them.

But I’m not sure business owners are getting what they pay for. Consultants and service-providers regularly charge more than necessary for their services. They hide behind impressive-sounding jargon to make it seem like they are doing things only experts can do. And they over-promise and under deliver. (“First page on Google!”)

The business owner pays a lot, doesn’t really understand what is being done, and eventually fires the company or consultant because the results were disappointing. That is my experience and I’m betting it’s the experience of many small business owners.

So my hope is to teach small business owners how to market their businesses online, using their websites, and using social media or pay-per-click ads, or whatever else we decide is appropriate. So they can do it themselves. Or, if they don’t want to do it themselves, they can properly evaluate the work they pay for.

That is my goal.

Early Challenges

I’ve had at least two major challenges since I started trying to do this a few years ago. One is a personal challenge, the other suggests that maybe I’m offering the wrong thing.

I don’t like asking for things from other people. I don’t like asking for help and I don’t like asking for favours (or anything that feels like a favour).

And I must say that sometimes I even struggle to offer help, even unconditional help. I’m a little shy and sometimes I don’t offer directions to someone clearly lost because I’ve got some stupid worry like they will tell me they’re not really lost, or they will be mad at me for offering to help with directions.

So looking for clients has been a challenge so far. It’s partially been a challenge because I had a 9-5 job and security. But it’s more of a challenge because I’ve always felt that I was bothering people, imposing upon them, even though I know what I have to offer is valuable.

To fix this, I recently took a course in learning how to engage people through email. I’m hoping what I learned can help me feel more comfortable with this process.

The other challenge is that, so far, most of my clients don’t want to learn how to market their businesses online.

They say “Yes, I’d love to learn how.” And then they don’t have the time, or they don’t have the inclination just now. And so, instead, they pay me to do it for them. Which is basically the opposite of what I’m trying to do.

Going forward I’m going to have to stick to my guns. But I don’t know if I can do that. (Or maybe I just need to rethink this entire idea!)

How is it going so far?

Today, my first day ever as just a solopreneur, with no full time job to fall back on, I did some work for two clients. And then I wrote this.

I think I wrote this because it made it really easy to ignore the most important thing I need to do each and every day in 2020: outreach to potential clients.

It’s the thing I’ll struggle the most with, I’m sure. Because I’m a good and patient teacher and I have nearly a decade of experience to offer.

But I know that getting in front of people is the hardest part. And it’s the part I like least about all of this.


In this space you’ll see regular updates about my struggles trying to get new clients and who knows what else. I hope that, by reading about my struggle, you’re inspired to chase a similar dream or, if you’re already on this path, that you will find something here that resonates with you.

Thanks for reading.

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