
When you guys pitched in to fill out my survey last month, I was super excited to respond to 30+ individual and interesting questions. One thing that really jumped out was the fact that much of the Five Figure Writer audience wants to transition into full-time freelancing, but hasn’t made the leap yet. In fact, about 75% of you guys are patiently biding your time, filling up your savings accounts, and picking up clients on the side.
(If you want to take the survey, sign up for the mailing list here and you’ll get a link to it).
There’s no shame in that! In fact, it’s the smartest way to do it. Plenty of people start freelancing as an emergency (that was my story) but it’s far, far better to have that runway time to save money, find clients, and generally not be frantic about your business.
So, for all you cube-dwellers building up your writing business on the side, here are five things you can do now to ease that transition:
Get your budget together & save a bunch of money
Let’s get the boring advice out of the way first: budgets and savings accounts are a freelancer’s best friend. I can’t say it clearly enough: cash flow kills 25 percent of small businesses early on. If you don’t get a grip on your spending or build up a bit of a cushion in the bank, freelancing will make you absolutely miserable and you’ll probably end up back in a cubicle.
If you don’t get a grip on your spending or build up a bit of a cushion in the bank, freelancing will make you absolutely miserable.
There are many ways to start tinkering with your finances before you transition into full-time freelance. I prefer the Dave Ramsey Financial Peace Plan and EveryDollar app, which helped my husband and I figure out a bare bones budget, organize and minimize our outgoing expenses, and save up $6K for a safety net (note: technically this is out of order of the FPU plan, but it was a necessary departure for the health of my business). You might enjoy a different finance guru or program, but it’s vital that you actually find one and use it to guide your decisions before you’re broke and waiting on a client’s check.
Financial stability (not necessarily security, which is a long-term concept) is about more than freaking out over late checks. It’s also about your attitude and your sense of desperation when you pitch new clients. If you have three or four month’s of expenses in the bank (and low expenses, at that) you can take your time with clients and make sure it’s a good fit and a good rate instead of jumping on low-paying work because your rent is due.
Embrace a farmer’s schedule (AKA 100% 24/7 is a myth)
One thing non-freelancers seem to assume about quitting their day job is that the transition into full-time freelancing means you’ll suddenly wake up filled with caffeine energy every day, ready to give your best to every client, crank out words, send newsletters, be on Twitter, and all that jazz.
In reality — and I wish someone had passed this along sooner — everything about freelancing goes in cycles. Much like a farmer, there are times of reaping and there are times of sowing. There are low income months and high income months, low referral times and high referral times, and, yes, there are low energy months and high energy months.
Everything about freelancing goes in cycles — there are times of reaping and there are times of sowing.
When you are tired and burnt out during your hustle, take it as a sign to take a break, not crank it out, so that you can get a feel for what it’s like to have cycles of high productivity and low productivity.
Start living by the phrase, “A man has as much luck as he has seeds in the field,” and practicing the art of reaping and sowing: write emails to people just to make connections, not to ask for any favors. Follow people on Twitter just for fun, not for business. And write things (and work with people) to spark creativity, not to build up your client list or land gigs.
Understand that confidence is a result, not a cause
Hands down the most popular topic, question, or concern in the survey was about confidence: How do I charge someone? How do I get my first gig when I’m not sure what I’m doing? Who’s going to hire me just because I want to write?
Listen, I had the exact same darn questions when I first got started. I was unprepared but dreadfully curious about how people got into this freelancing thing. And then I got laid off, and you know what? I wasn’t curious any more, I was desperate, so I just made it happen.
This is so, so important to understand: confidence is a result of doing good work and having good customer interactions. It is not a cause of those things. If you wait until you feel confident to pitch that client, send that email, send that proposal, or send that invoice, you will never. get. anything. done.
Confidence is a result of doing good work and having good customer interactions. It is not a cause of those things.
Is it scary and weird to start charging people money for something you love to do? Yes, at first. But once you do it for a while you start to build up that confidence that takes you to the next level, and the next, and the next. But if you don’t step up without confidence (and with fear and butterflies and maybe even some grasshoppers in your stomach), you’ll never reach the point of having actual confidence.

Find something bigger than money
There’s no denying that money is a big motivator for freelancers. Like I said in the budget section, cash flow can make or break your business, so income will always be a sign of the viability of what you’re doing. But despite your dreams of rolling in the dough and taking on a housekeeper or private chef, money only takes you so far in the freelance game.
I started this wanting to prove I was worth more than a $50K salary, and I did that. But pretty quickly after achieving that income goal (as well as earning five figures in a month), I lost my gusto again. I learned pretty quickly that beyond a certain ego factor, money isn’t enough to get me out of bed every morning.
Money isn’t enough to get you out of bed in the morning, and it’s not a compelling reason for people to work with you.
Money also isn’t a compelling reason for people to work with you. Think of hiring a lawyer or doctor for a huge moment in your life. Who would be more attractive, the one who got into it for the money, or the one who got into because they realized law/medicine was their ultimate calling and they find themselves renewed with every client or patient they help? Money doesn’t inspire others to join your cause or support your mission; you need a bigger “why” to make your business attractive to you and your clients year after year.
Accept “what you like” as a calling, not a fluke
As you try out different forms of writing as a part-time freelancer, keep your eyes peeled for what you actually like to do. Don’t punish yourself and assume that whatever you hate most is what will make you the most money — that’s a false value you’re bringing with you from the traditional working world, where the crappiest jobs often get the highest paycheck. It will also completely drain the life out of you.
For example, I spent more time than I want to admit thinking I had to write high-volume SEO blog posts and deliver social media strategy instead of white papers. Three years in, I’m finally unashamedly making white papers my specialty, and I won’t touch social media with a 10-foot pole (except for myself, of course). It took time to understand that some writers love social media and I hate it, and some writers don’t like writing white papers, and I happen to love it. These aren’t flukes — they’re signs that propel us toward our best work.
When something comes easily to you and you love it, don’t dismiss it.
When something comes easily to you, don’t dismiss it. If you love something, it’s not necessarily because the thing is awesome, it’s because you love it and you’re meant to do it. We all have unique talents and interest. You owe it to the freelance community to think about what you really, really love and focus on it.
What freaks you out about the transition into full-time freelancing?
These are just five of the lessons I’ve learned in almost three years of exclusive freelancing that would have been very helpful to learn early on. What other questions do you have for me about making the transition?

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