What I Wish I’d Known

This month, I’m presenting a talk for the WordPress community here in Victoria: “What I Wish I’d Known: Ah-Ha Moments from Five Years of WordPress Freelancing.” If you live in Victoria, feel free to join us on January 22, 2019.

Below is a teaser of a few of the Ah-ha Moments I’m planning to share.

There’s a myth about the fearless freelancer who takes on world with only a laptop, jet setting from Paris to Fiji, living the dream with a four hour work week.

The myth is illusory (and rather self-centered). Most freelancers I know aren’t globe trotters, but hard workers rooted in one place. If the rest of the world is working Monday to Friday, 9-5, you can’t put in four hours a week and expect to stay in business.

Even so, the myth is right about one thing: freelancing is fundamentally an individual pursuit. Most of the time you’re a kind of digital monk, working alone in your cell. Still, I’ve been surprised how much I’ve really needed other people.

I would be lost without my wife to vent with on hard days and to celebrate with on good days. My daughters barely know what a website is and easily take my mind off work at the end of the day.

I would be lost without fellow freelancers – peers with deep technical insight whose advice over the years has fundamentally changed the way I work. You can’t solve every problem by Googling it; other freelancers have been essential to learning the ropes.

My colleague Jacob McKee has also been indispensable to keeping up with the high volume of work that we’ve been given recently.

I would also be lost without a business mentor, a local business professor who sits down with me every few months, asks hard questions and gives bang-on advise about how to grow.

Freelancing can be lonely work – but I don’t think it works well in isolation. I was so excited to be free from team meetings once I left non-profit work in Toronto, only to look up a few years later and realize I was missing something.

A related Ah-ha moment was the realization that I didn’t have to be good at everything. When I started freelancing, I felt so green and intimidated by full screens of code. I thought I was a fake web designer!

I soon learned that I didn’t have to be a rockstar at PHP coding to design great websites. That’s the whole point of WordPress! For other people, it’s the reverse: you don’t have to be brilliant designer to code a brilliant WordPress plugin. You can find another capable designer to help.

Some of the joy of freelancing is offloading skills you aren’t good at. But it takes a community to be able to do this well.

A lot of where I crashed early on was expecting new clients to waltz in the door. With a full-time job, work tends to just show up on your desk. You don’t have to beg your boss for it!

I remained in a very passive mode when I started – expecting clients to come to me. In the early days, I wasted so much time in my office, redoing my own website, testing out new business card designs. It took a while for me to realize I needed to get out there. Soon I joined Meetups, went to all manner of (dreaded) networking events. I told my wife I’d do ‘one crazy thing’ a week such as cold call an organization that needed a new site.

Years later, I still need to spend several hours a week scouting for new business. Now it’s more one-on-one meetings or eNewsletters. For others, that time is spent on social media or podcasting. Some of these efforts may be ‘wasted’ – but they remain essential to the health of a freelancing practice.