Avoiding the edge

Last week, I received my first 'real' freelance check in the mail. This was a partner company I'd worked with in California. They asked me to refresh their logo. Simple, straightforward and not too creative. I sent a contract. They agreed. I did the work. I sent a bill. They paid within 30 days. It's how it's supposed to work, but I've rarely experienced a client relationship that works that smoothly.

As a result of that check, I've set up a DBA ("Doing Business As") and have a sole proprietorship in [My Name] Design. The name is nothing creative (though I like my idea for a logo), but it's simple and straightforward. I've reached out to people in the neighborhood and have a list of web coders I could work with to make my site. They're also potential collaborators if I do the freelance road and need web resources.

A couple months ago, I contacted a woman who is friends with our realtor. She got back to me last week and we met today for lunch. Here in Dallas she's one of the leading event planners for events in the 300-500 person range. She's got a few contacts if I'm interested. She works with a designer in the area and might connect me with her.

I've just finished creating the brand for a dear friend who is going into Executive Coaching. Along the way he's had various people ask if I'm available.

When I reached out to a former co-worker now freelancer extraordinaire for some ideas, one of her contacts then reached out to me.

I know that one of my former creative directors would like to work with me. I think my current company would be willing to work with me as a contractor.

So, the issue is, do I opt to make my life hellish for a while and go for the freelance gig until it takes off and I can quit my current job, or do I play it safe and keep plugging along as is?

I would like to be doing freelance by the time Brex is in kindergarten and it takes a couple years of hustle to get it moving along. On the other hand, I'm now 40 percent vested in my company and the money gets fairly big now each year I stay on as a full-time employee.

Paving stone by paving stone I keep laying the path, just in case. I set up a business account today thanks to that freelance check. I emailed those clients to thank them and tell them I'd happy to work with them in the future. They emailed back right away to say they may have more work later in June.

It just feels like those paving stones are leading to the edge of a cliff. I can get to the edge, jump and hope to fly, or risk crashing hard, or not risk anything and stay where I am. Yikes!