So you want to be location independent, have a passive income and make money off what you love, right? Don’t worry, all you need to do is start a company, sell something online and have a blog. The rest will fall into place, since you’ve got passion and know that doing your own thing is the path to happiness.

Can I call horseshit on that?

I get asked for advice on starting/running a freelance business quite a bit, since I’ve run mine for 15 years without ever going into debt, having a second job to fill the gaps or lacking in new paid work. All without any advertising too.


Doing what you love isn’t good enough. It’s not even close to being a recipe for success. You have to do what you are really fucking good at, know it inside and out, and have worked at it for a long time. Going freelance right out of school or right after you learn a new skill can be both a comedy of errors and extremely egotistical (and you’re smarter than that).

Past having the necessary stone-cold expertise dialled in, business is relationships. These relationships take time to cultivate (a lot of time). Your business will come from people you know and people they know, so if those connections aren’t there, the business you need to survive won’t be there either.

Running a business is also an incredible risk. Most of them fail and fail quickly. Even the ones that were started by extremely passionate people.

My advice is always the same—pay your fucking dues first. And in a world of positivity, encouraging Rumi quotes and the mentality “if you’ve got passion, your business will succeed”, I sound like a meanie and total buzzkill.

Be mentored, do the job you want for someone else for a while first. Learn from them what it takes to run that business (on their dime, since they’re paying you as their employee). See how they deal with customers, HR, the government, and difficult situations. Network while at that job with other industry people and build relationships. Make a name for yourself before you need to use that reputation for your own benefit.


My story

I worked for a web design company for years. I started as a junior graphic designer and worked my way up to running their digital department as a creative director. I learned what it took to be “creative on demand” from 9-5 each day and deal with clients (good and bad ones). When I didn’t know something, I asked my boss or colleagues. I actually saw how to merge my passion into a business that made money. I hated the job and my boss, but kept at it. I went to (and spoke at) industry events, met people and cultivated relationships, even though I’m extremely introverted. I got out there and connected with as many folks as possible.

When I finally left that job I was in the perfect place to do my own thing. I had a network of relationships in place that were eager to give me work (including clients of the place I worked that wanted to follow me to where ever I went next).

I had first-hand knowledge of running a web design business because I had worked for someone else’s for years. I paid my dues and learned a great deal before I went out on my own. So when I started my company, I had clients already lined up to work with me.


I say all this not to your crush dreams, but offer a dose of reality and glimpse into the real world of working for yourself. It’s not all glamour and independence—it’s hard work, applying learned skills and having some real discipline. There’s no instant gratification to be found in freelancing, instead there’s cultivation and hard work over time, which leads to lasting success.

Once you’ve spent the necessary time doing that, it can be pretty fucking awesome.