Calculated Risks

Entrepreneurs by nature love starting new things.

And it’s a great gift to be able to launch out into the unknown and act on your dreams.

I quit my job in 2011 before I had all my ducks in a row to start my own freelance copywriting business. And it wasn’t easy. That first year I made very little money.

But fast forward 6 years and I’m getting the hang of it. I stay booked pretty solid. My big struggle now isn’t, “How do I find clients to pay me well for copywriting work?”

Instead it’s, “Do I even want to keep doing this? I want to do something new!”

And I am. On the side I’m growing a small marketing agency for insurance agents and financial advisors. But my bread and butter is still copywriting.

Will my marketing agency take off so that I can one day fire myself as copywriter and focus all my energy on creating and managing the systems of my agency?

I hope so. But until then I must focus on what’s proven to work.


Because being an entrepreneur doesn’t mean you have to take stupid risks. I’m married with three kids. My wife is a full-time mom and so I’m the sole breadwinner. I can’t afford to just jump in the deep end anymore and see if I’ll sink or swim.

I must be more methodical and more pragmatic. You can’t avoid risk altogether but you can learn to take calculated risks.

I learned this the hard way. Last year I thought I could just dive in the deep end and figure it out. I fired myself as the copywriter and focused 100% on my new agency. You can read more about it here.

Bottom line: that was stupid!

Cash flow dried up and it created a lot of stress in me and my marriage. It was a horrible experience that I never want to go through again.

So what’s the alternative? Get a job? Ha! I don’t think I’m employable anymore after having my own business for six years.

No, the alternative is to focus most you efforts on what’s already proven to work vs constantly starting new things.

This is why I’m still committed to copywriting until my new “side hustles” reach a point where I could safely stop writing copy for clients.

What about you? What products or services have proven to be reliable for you in the past? How can you optimize those and grow them steadily while you work on the “new thing” on the side?