Should you quit your job to freelance: 6 questions to ask yourself

One of the biggest questions I get asked is how to get started and become a freelancer. I took that leap of faith long before this whole gig economy became a thing. I was working in the corporate world when my son was born and that Mommy hormone kicked into high gear and I just couldn’t bear going to my office every day and leaving him behind. But I’ll be real, I also couldn’t give up the money I was making to fuel my lust for finer things, like travel, spa treatments, and shoes. That’s when I decided to become a freelancer.

So after many late night discussions with my ultra-conservative husband, I had convinced him that I could make decent money working from home as a PR freelancer. Here’s how I did it:

1. Is your financial house in order?
This has to be your starting point. This means saving up for at least six months. As a freelancer for 28 years, I can tell you it is a feast or famine business. Either you’re swamped with work and making tons of money, or you’re watching General Hospital and napping everyday and buying boxed wine to save money. You’ll also need to figure out what non-essentials you can live without. Getting your nails done every week? Letting those expensive highlights grow out for awhile? I already mentioned boxed wine.

2. Are you a self-starter?
This is another biggie. If you’re not organized and a good project manager, you’re probably going to have problems running your own business. You’re your own HR department. Your own finance department who has to manage invoices and payments. You’ll do your own research. And often you’re tech support. It’s just you.



3. Who do you know?
I’m serious. This was the one area that helped me convince my husband that I could be successful at freelancing. He saw the quantity, but also the quality, of my vast network of contacts I could reach out to for work. But it goes beyond that. Those contacts are connectors (anyone remember The Tipping Point?). You’ll use those contacts to introduce you to other contacts. It helps to be a natural-born networker.

4. What’s your 8-second elevator speech?
What is it you do? What is your business? If you’re not familiar with the concept of an elevator speech, pretend you’re riding up an elevator and the person next to you says, “So what do you do?” You have less than eight seconds (3 floors) to tell them what you do. This will become your schtick. You’ll use the list of contacts you created above to introduce yourself and your schtick. Any time I find myself in a famine, I create an updated list and reach out to those contacts with my latest schtick.



5. How well connected are you?
Put yourself out there. Join local or trade associations that align with your business. Follow blogs and thought leaders. Join social media groups to connect with others. This is how you’ll get ideas for how to market yourself while expanding your network.

6. Are you willing to work for free?
Huh? What? But I’m doing this make money. In order to establish yourself as a resource and to gain a little experience as a freelancer, you may have to give away some work or projects. One of the first things I did when I made the leap was reach out to the local American Cancer Society (my father had recently died of cancer) and I volunteered to do some writing or event planning for them. They asked me to join their marketing committee which had several professionals on it who became contacts, but it ultimately led to a position on their board which opened so many doors for me (and was personally fulfilling).


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