Are You Ready to Get Into Freelancing?

Freelancing can be a great move to make. It can change your outlook on life, improve your financial situation and give you more freedom. It can also open up opportunities that you didn’t have access to previously, like traveling to new places or maybe a book deal.

But freelancing also can be a bad move, in some circumstances. Many people get desperate and throw themselves into this line of career without thinking and planning. The result? You’re worse off than you were when you started.

So when is the right time to move to freelancing? Is it a good decision for you? Will it be everything you hoped for? Read on.

Are You Emotionally Ready?

Cons: Freelancers take some hard emotional knocks. Rejection is common, and so are revision requests. You might hear, “This isn’t what I want,” or, “I don’t like what you’ve written,” often. You’ll need to be able to distinguish and separate your work from your self-worth. You may feel like clients boss you around, and sometimes clients can be rude or blunt.

Pros: Moving towards self-employment and a freelancing career can make you feel better about the work you do and your contribution to the world. You might feel more valued, as if your writing makes a difference. Your self-esteem could rise substantially, and your confidence as well. You could even feel relieved, now that you’re away from employment you found oppressive.

Tip: Learn that rejection and revision requests are no reflection on who you are as a person. Writing is very subjective, and some people will like what you do. Some won’t. That’s okay – you’re still a great individual with plenty to offer the world.

Are You Financially Ready?

Cons: If there’s one thing that freelancing doesn’t offer, it’s a stable income. You may not get paid every week, and you may ride an income roller-coaster of great highs and terrible lows. You’ll need to invest money into improving your business or skills and have cash available for expenses. A cushion of savings to fall back on when times are tough is crucial.

Pros: Preparing to weather highs and lows means you have good plans in place to ride out tough times. A cushion provides financial security, so you’ll feel more comfortable. You’ll be able to adjust your rates and schedule to find the optimal income flow that meets your needs. Learning to budget effectively also tends to improve your financial situation overall.

Tip: A proper plan for marketing your services helps you keep income flow steady. Market steadily, whether you have plenty of work or none at all, to make sure that you never have an empty plate. It’s better to have a waiting list than have no work at all.

Are You Business Ready?

Cons: Freelancing often equals freedom, but that doesn’t mean freedom from paperwork, business plans, proper accounting systems and more. Launch yourself into your career, and you’ll discover you’re not set up to accept payments, keep track of income and expenses and show banks you have a serious business. The result? Improper business planning can cost you an organizational mess and extra expenses down the line – sometimes to the tune of thousands.

Pros: Plenty of online sites and offline organizations provide help and advice, checklists of ‘must haves’ and resources to set you up with your business needs. By preparing up your business properly before starting, you’ll reduce wasted time, eliminate headaches and have smooth operations all the way to success.

Tip: Don’t try to do it all yourself or take on tasks that require skills you don’t have. Accounting is for accountants. Web design is for designers. Technical support is for techies. Focus on what you do best, and invest in the right people to make your business more successful.

Are you Stability Ready?

Cons: Many people turn to freelancing when the situation is desperate. They want a way out, an escape or a rescue from current circumstances. They forget to consider that switching career paths sometimes just changes four quarters for a dollar and doesn’t solve anything at all.

Pros: Rushing into anything often creates more problems than it’s worth. Yes, sometimes desperate situations call for desperate measures, but see if you can’t hold on to what you have for stability’s sake while setting up your business. Preparing for a launch over a period of six months often produces better results than a rushed, save-me decision to freelance.

Can you think of any other situations you need to be prepared for before you start freelancing? What troubles have you run into? What did you learn from your own startup? What other situations do you feel you need to be ready for before taking the plunge?

Want to learn more ways to prepare yourself for a damned fine freelancing business? Get The Unlimited Freelancer and tap into secrets the successful freelancers use to get ahead.






5 responses
  1. Allen Taylor Avatar

    Nice writing. You are on my RSS reader now so I can read more from you down the road.

    Allen Taylor

  2. Lisa Avatar

    The “financially” ready point is a biggie: even if you are working, and even if your client is legit and intends to pay you in a timely manner, you may not see a nickel for a month or more after you get started. That means – a month without a nickel. Can you weather that?

    And then there are the clients (often big ones in this economic climate) who pay not 30 days net but 45 days net. By the time you’ve gotten your contract, done some work, billed, and gotten paid… well, you can do the math!


  3. Alik Avatar

    The two biggest sections in this are the financial stability section and the self worth section. Having a financial cushion is SO important, and if you haven’t started freelancing yet and want to get into it, try to save as much as humanly possible before you start. The term “feast or famine lifestyle” has never been so literal. I try to have enough money in my savings account (that’s not earmarked for bills or anything else) to cover at least the next business quarter or longer. I also set monthly and quarterly quotas of what I need to earn in order to pay my bills and survive, and another quota of what I’d ideally like to make to have “fun money” and money to contribute to savings.

    As far as self worth goes, in the beginning of a freelancing career it’s easy to work on a first draft really hard, become really proud of it, and then have it rejected leaving you feeling crushed. I offer two rounds of revisions for free with every project that I do, so try to keep in mind that a first draft is a first draft for a reason – there are more drafts to follow. Learn to expect your client to want revisions instead of crossing your fingers that they’ll like the first draft. Plus, if they like the first draft and don’t need revisions at all, then you’ll feel like a million bucks!

  4. David Dittell Avatar


    Good “checklist” to make sure you’re ready to make the move.

    As someone who writes “on spec” creatively, it’s much the same. The one thing I can say for criticism/rejection is that a lot of the time you learn from it — not just how to become a better writer, but how to figure out what somebody wants from you. I couldn’t tell you how many times someone has even specified a problem in my writing, only for me to figure out that the real problem lies 50 pages earlier.

  5. Lizjul Avatar

    Thank you James for this article. It helped me to think about the goals I want to achieve through freelance writing. I was sharing my thoughts with my mom and dad about venturing into the world of Freelance Writing. My dad, who has good knowledge on business and business practices, asked me simply what my objectives would be for freelance writing. I was able to tell him without fidgeting and stumbling on my words. I was able to convince him that it was a good move for me to take.

    I am new to finding work as a freelance writer. But I have to say out loud, mostly to myself that I am not interested in making Freelance a career. Instead it would be a part of my career. I want to get my writing out there to share my knowledge with others and to earn extra money. I do fret at rejection, but I need feedback on what I’m writing. I love to write, I always had. I have had feedback from friends and family members. But I need more. I even questioned if I was a good writer. I literally went back to looking at old college and graduate school reports I had written. I did very well. But I realized that strengthening my confidence is pertinent. And I do believe there are people out there who would appreciate the work that I do. But just the fact that someone who would hire me as a writer, is a breakthrough in itself: added on with the critiques and changes, I have to say I would appreciate. It’s similar to work in that someone is investing in your talent enough to make sure your work is the best it can be.

    I also want to thank you James, for emphasizing planning. That to me is key to “being ready” or getting ready to be a freelance writer. I began to write down topics I would write, if and when I am hired, the niche I would want to reach, methods on how to reach and find my niche and so forth! I currently have a small business, so I would possibly have a good business flow.
    I believe I am ready for this! Freelance writing assignments come to me!

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