Are You Ready to Work for Yourself? 5 Questions to Ask


Working for yourself full-time can be a great thing. There’s nothing like striking out on your own to develop your skills, and the freedom you’ll gain over your time, income, and opportunities is incomparable.  

Still, working for yourself is hard – in ways you don’t always imagine when you’re starting out. So how do you know if you’re ready? Start by asking yourself these five questions.

Why am I doing this?

What’s going on in your life that makes you want to take the leap? And if all those situations suddenly changed – if you had a brand-new boss, a raise, and a corner office – would you still want to work for yourself? Pay attention to your answer. You should be ready to make a commitment that lasts through changing circumstances.

How long could I realistically live on the savings I’ve built up?

Figure out how much you think you’ll need…then double it. Particularly in creative industries – where you’re offering a service, rather than a product – the line from successful client acquisition to actually seeing a check in your bank account can be a long one.

Am I ready for EVERY aspect of owning a business?

Making a living from the creative work you love doing is great. But remember that you’ll also have a whole new list of responsibilities aside from the creative stuff. Make sure you’re ready to handle more complicated taxes, find a space (or work from home), and – of course – get out there and find some clients.

What’s unique about me? How can I brand that?

You know you’re a great copywriter/graphic designer/web developer. Remember, though – there are a lot of talented creatives out there. What sets you apart? How can you cohesively and visually represent – aka brand – the things you alone can offer?

Who’s in my corner?

Although you may now be a business of one, success doesn’t happen alone. Think about the network you’ve built over the years…who do you know whose skills are the perfect complement to yours? Now’s the time to brainstorm the partnerships you can build based on those relationships.

Need help figuring out how to brand your services? I’m all ears! Drop me a line: