From Moonlighting to Freelancing

I’m working on a new Freelance column for the next issue of HOW Magazine and I need your help. Here’s the question:

Do you need confidence to make the leap from moonlighting to freelancing? And if so, where does it come from?

2 thoughts on “From Moonlighting to Freelancing

  1. Neil Renicker

    Hi Ilise,

    I thought I’d share a quick bit since I just made a transition like this. Here’s a few key things that did it for me:

    1. A goal. I determined that I’d make the leap by date “x” (about 1 year away at that point). I told my current employer and other friends and family about the plans, so it would have been hard to back out.
    2. Talks with inspiring, successful people. I had meetings with people that gave me good advice and told me it could be done. I believed them. They told me to have a vision, get help from others, and don’t spend much money. That made sense to me.
    3. A commitment to hard work. When you realize that your venture is going to have to ‘keep bread on the table’, you don’t have much choice but to work like crazy. The commitment to work tirelessly to get this thing off the ground helped me out a lot.

    Hope that helps!

  2. lidia varesco design

    Neil makes some great points.

    I agree that it’s important to talk to your current boss and make a plan. If you’re lucky to have a supportive boss, it will make the transition easier. And you may end up leaving with a new client! (after all, you know the business already)

    I also had many talks with self-employed friends/family who became mentors and go-to persons for questions. This is invaluable when starting out and is a great way to boost your confidence. Simple questions such as, do I need a second phone line? how do I handle taxes? can seem overwhelming until you talk to a seasoned pro. And over the years, I’ve paid it forward by being an adviser and “cheerleader” for lots of others who have taken the solopreneur plunge.

    Along those lines, be prepared for the naysayers. I was lucky to have supportive friends and family, but there were a few “Are you sure about this? How will you pay the rent?” questions that threatened to derail my confidence. Brush it off and move on with your plan.

    Having a certain volume of work helps. Most freelancers I know decided to go solo when they realized they were putting in more time after-hours than in their day job. Knowing you’ll have at least a project or two when starting out helps give you confidence.
    Lastly, I agree with Neil’s point about hard work. Be prepared to work twice as hard (at least in the beginning). But the satisfaction of having your own business and creating the life you want makes up for all those long hours!