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1. Start by going freelance.
I don’t mean you should just up and quit your job without notice. No, that would be lunacy. What I mean is start freelancing while you have a full-time job. A study by the Academy of Management found your businesses is 33 percent less likely to fail if you launch it while you’re still employed.
So find your first client well before you quit your day job. Look on Flexjobs, Craigslist, Worknola or whatever, apply and (hopefully) get hired. Once you have built up some recurring work, test-drive freelancing by taking a day or a week off and working on freelance projects during that time. Pay attention to what you like or don’t like about it. Do you enjoy being at home and working? Do you find it easier to get things done in a shared workspace or a coffee shop? Maybe you’ll find you miss the structure and camaraderie of your office. Whatever you learn, take that knowledge and use it to decide whether or not freelancing is right for you. Before I took the plunge to full-time freelancer, I scheduled a whole vacation week during which I only worked on freelance projects. I loved it! And I loved that I knew I loved it.
2. Track your bare-bones expenses for a couple months on a spreadsheet.
I did this so I knew the bare minimum I needed to survive. I found out I can live comfortably on $24,000; I can scrape by while maybe feeling a little deprived on $18,000, and I can survive on $12,000, but just barely. Those numbers give you something to aim for as you build up your roster of clients.
3. Build up more freelance clients and income sources until you can easily meet your minimum expenses.
The great thing about getting clients is this: once you start, if you do a good job, your existing clients may give you more work or refer you to others. As work snowballs, you might find yourself with an additional part- or full-time job on your hands. Yes, this might mean long days, working on weekends and a lot of stress. Remind yourself it’s temporary, and that there’s a light at the end of the tunnel–self employment! A career with unlimited growth and income potential, flexibility and opportunities to work from home with your cats.
4. Start a website.
You should actually do this before you start freelancing. It doesn’t have to be fancy. Just let it be your digital placard in ye old Internet land. Feel free to optimize your website toward your business or just use it as a place to blog and share information about yourself. The great thing about blogging/creating websites is that it’s perfectly fine to figure it out as you go along. And once you start your website and optimize its SEO and hook it up to Google Analytics, you can learn not only about yourself, but also about the people who are taking in the stuff you’re creating. Take this blog, for example. I had no idea what its purpose would be when I created it, and it’s still a work in progress–but I can tell which posts are the most popular ones (that’s the microblading piece, by a landslide) and see the need they’re filling. Also, clients like it if you have a website. Why would they hire someone who’s a virtual blank space when they could hire someone they “know?” On the same note, max out your LinkedIn real estate, too, and get aggressive on social media.
5. Buy a house or refinance your mortgage (or both).
I actually did both of these things. I closed on my house in 2014 and refinanced (sweet, sweet 2.8 percent, baby) in 2016. The reason I refinanced wasn’t only because interest rates were good. It was because banks won’t even look at a self-employed person until they have two years’ of freelance income to present. So I knew I’d be locked out of the real estate market for a MINIMUM of two years.
6. Project your income for your first year and get Obamacare based on that income.
Yeah, you need to get on that Obamacare fast, because who knows what’s going to happen under this new administration? There’s some possibility that existing users may be grandfathered in, though. So figure out your projected income based on the work you’ve been doing for the clients you have. Err on the conservative side. Then pay for the year up front on a credit card, preferably one that offers cash back or air travel miles. Here’s to your health.
7. Save up a nice money cushion.
This should be easy because of all the freelance work you’re doing on top of your full-time job. As tempting as it may be, don’t treat yourself with your additional income. Put it in the bank where it can serve as a cushion during that precarious first year as a freelancer. I saved $10,000 before putting in my notice. Which is comforting, because I’ll be ready in case there’s a client who pays late or not at all, a pet who needs emergency surgery, etc. etc….
8. Go to the doctor, use sick days, and max out your cafeteria plan.
Get your health-related issues worked out while you have got a solid health insurance plan and paid sick days. Do any surgeries while you still have a cafeteria plan. I used paid vacation days and my company’s cafeteria plan to have PRK eye surgery– and I’m really glad I did. Neither of those luxuries would have been afforded to me if I was a freelancer.
9. Talk to other freelancers who’ve made the leap.
I found invaluable advice, support and encouragement from talking to other freelancers. In fact, Juliet Meeks gave me the advice in #6.
10. Quit your job and tell people why.
When you quit your job, people are going to be curious about your reasons for leaving. This is a prime opportunity to tell them you’re going freelance and hey, you’re available for work. Also, if there are cocktail parties, events, industry mixers, etc., that you usually opt out of, well, STOP. Go to that shit. Tell people you’re freelancing. SING IT TO THE WORLD. (Just like I’m doing now … cough, cough.)

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