Before I launched my freelance copywriting business, I spent three full months planning my escape from corporate America. (Four months if you count the month I spent over-thinking whether I should quit my day job . . . or not.) 

I read Peter Bowerman’s The Well-Fed Writer cover-to-cover. Twice. I built my web-based writing portfolio. I converted our rarely-used formal living room into an office. And I planned my business implementation strategy. 

My early efforts paid off. Within 90 days of starting my business, I had replaced my full time income. 

Whether you want to start a B2B copywriting business or another type of freelance writing business, there are several questions to ask yourself before quitting your day job. 

Here are my top seven: 

1.  Do you have the writing skills and talent to produce marketable content in your field?  

Reality Check: I wrote a lot of marketing copy for my day job. And it was good stuff. I was confident that other companies would agree. Can you say the same for your writing?

If not, spend time acquiring the right experience before quitting your day job. Take some writing classes. Offer your writing services for free to a non-profit organization or a friend with a small business. Hire a writing mentor. Do whatever it takes to gain the writing skills and talent to compete in your market. 

2.  Do you have the cash reserves to replace your day job income for at least four to six months? 

Reality Check: If you and your family rely on your day job paycheck to pay the bills, you MUST have at least four to six months of income stashed in a savings account. It takes time to build a clientele and project backlog so you will need to supplement your freelance income for the first several months – maybe longer. 

I ended up cashing out a small 401K account to create my cash reserves, although I wouldn’t recommend doing that if you have another savings source. But for me, this was the only choice. (Sidenote: since the recent stock market crash would have killed my account value anyway, I don’t have any regrets for putting that money toward building a business.) 

3.  Do you have the full support of your immediate family? 

Reality Check: Starting a freelance writing business is risky. There’s the real possibility that you’ll burn up your savings without getting your business off the ground. (There’s also the real possibility that you’ll be wildly successful and much, much happier as a self-employed business owner.) It is important that your immediate family, meaning your spouse or significant other who also provides an income to support your family, understands this and supports you anyway. 

I honestly believe that having the support of my family is one of the major reasons for my success. When things didn’t go quite the way I wanted, I had an entire team cheering me on. Without that support, it would have been easy to give up. 

4.  Are you prepared to burn your current employment bridge? 

Reality Check: When I quit my day job, I naively expected my current employer to be my first and best client. After all, I knew their business inside and out and they knew I produced quality content. They gave me one project before realizing that I was also seeking work from their competitors. And that was the end of the relationship. 

My market niche is very focused and very competitive. I work with several companies that sell similar software to the same group of prospects. My current clients accept that; my old employer didn’t. Whether you will be working as a freelance writer in your company’s niche or a different market, it’s important to understand that, when you quit your day job, you may be severing that tie forever. If this does happen, will you be okay with that?

5.  Have you planned your business marketing strategy? 

Reality Check: By the last day of your current job, you should have a complete marketing plan in place for quickly getting your business off the ground. As I mentioned earlier, you should have your office set up, your web site built and your online writing portfolio in place. You should also have a list of prospects to contact and your sales pitch ready. In addition, you might want to get your business bank account established and research any business license requirements in your area. Having all of these things in place before you actually launch your business will save valuable time (and money) once you become an official business owner. 

6.  Do you have the self-discipline to be self-employed? 

Reality Check: Working for yourself from home isn’t always easy. Many potential distractions will tempt you to work less and play more, or spend your most productive time doing laundry or running errands. If you want to succeed as a full time freelance writer, you need to commit a set number of hours each day to your work. And the more hours you commit to your start-up business, the greater your chances of success. 

Friends, family and even acquaintances often mistake my work-from-home lifestyle for a stay-at-home mom existence, so it’s a constant battle to set boundaries around day time commitments. Even my own kids expect me to do things for them during my designated workday. Do you have the self-discipline to make your work a priority when a million other things are vying for your time?  

7.  Can you handle the stress of self-employment?

Reality Check: Self-employment is stressful. Some months I’m buried in work and other months I run short. Deadlines constantly nip at my heels and threaten to crush my creativity. If I’m too sick to work, I don’t get paid. Same thing when I take a vacation. The constant stress associated with full time freelance writing isn’t for everyone. But if you’re like me, and overwhelmingly prefer this stress to a “real” job, start planning your escape today!

 “I’m a freelance writer, but I don’t know anything about copywriting.”  

I recently had a conversation with a down-sized corporate administrative assistant who was trying her hand at freelance writing. She told me that, although she was a freelance writer, she didn’t know anything about copywriting. (I take that back. She did know one thing about copywriting: it paid a LOT better than her current assignments.)

That’s when I showed her how her odd freelance writing jobs and personal communications experience had given her the tools she needs to enter the more financially lucrative world of B2B or even B2C copywriting. She just needed the vision to tweak her talent to fit the corporate mindset. 

From Freelance Writer to Marketing Copywriter 

To illustrate how different types of freelance writing translate into copywriting, here are five ways your experience can pay off in the corporate world: 

1. If you write print magazine articles, then you have the experience to be a corporate ghostwriter of trade magazine articles and advertorials.  
2. If you write fictional short stories, you have the experience to write case studies (truthful storytelling with liberal customer quotes and a marketing twist). 
3. If you write content for article marketing purposes, you have the experience to write content for a corporate blog, internal employee newsletter or external client newsletter. 
4. If you write technical documents or manuals, you have the experience to write marketing white papers.  
5. If you have social media expertise, you have the experience to set up and manage a company’s Facebook page and Twitter account.

Before making the leap from freelance writer to copywriter, you might want to study the type of content that relates to your experience. A wide variety of case studies, trade magazines, white papers and newsletters can easily be found with a quick Google search. 

Copywriter Confession: Years ago I used to write 750 word feature articles for Better Nutrition magazine. My ego loved getting a byline, but the pay was really low. Ghostwriting 750 word articles for construction trade magazines may not be as inspiring as natural health, but the pay is a whole lot higher!

In business, the Lunch and Learn is a good way to teach employees something valuable without cutting into their main productivity time. Let’s say a company recently upgraded their software. It might host a Lunch and Learn to demonstrate all the new features to its employees. The company plans the training session and buys the employees lunch. In turn, the employees forfeit their lunch break to sit in a conference room, eat free pizza and learn all about the new software version. 

If you’re a freelance copywriter that works from home, there’s no such thing as a free lunch. And if you’re like me, you tend to work through the noon hour while nibbling at your desk anyway. But that doesn’t mean you can’t initiate your own version of the Lunch and Learn – the freelance version. 

Free Lunch and Learn Reading Material 

One of the best ways to become a better copywriter is to consistently read really good copy. But if you want that copy to qualify as Lunch and Learn material, it also needs to teach you something valuable. 

I’ve chosen three documents (in no apparent order) that I think qualify for the freelance version of the Lunch and Learn. Each one can be read start to finish in an hour or less.  And they are all free to download (no registration required). 

So grab your lunch and get ready to learn!  

1. 279 Days to Overnight Success

 This engaging manifesto by Chris Guillebeau is touted as:

 ”11,000 words of free advice on how to create your own success with your own project.”

 2. A Human’s Guide to Freelance Living

 This easy and entertaining read by Charlie Pabst is also touted to be a manifesto:

“It features tips on finding ideas, staying organized, getting clients and ultimately making money doing what you love.”

 3. The Death of the Salesletter

Michel Fortin’s report on Web 2.0 and Its Impact on the Future of Internet Copy is insightful and educational. Michel says: 

“I want as many people, copywriters, marketers and buyers alike, to get this information, because, as a copywriter for many of the web’s top marketers, I’m seeing a significant transformation occurring that simply cannot be ignored.”

Copywriter Confession: When I take a break at my desk to eat, I tend to surf the web and read online news. Bad idea. The news is so depressing, but for me it’s like a train wreck: I can’t help but watch. So do as I say, not as I do. Stay away from the news and spend your learning learning something useful.

My 15-year old daughter recently asked if she could go to a concert. Her friend’s dad offered to take the girls, hang out nearby (but not too close – and probably with ear plugs) and bring the girls home afterwards. She also had her own money to pay for the ticket. 

Sounded safe, sensible and well-planned, so I said, “Sure.” 

A few days later, when I found out that the concert was on a school night and my daughter wouldn’t get home until after midnight, I changed my answer to, “WHAT??!!! There’s no way you’re going to a concert on a school night!” You can imagine how well that went over. 

So, since the plans were made and the tickets were bought, I agreed to let her go as long as she got up for school the next morning and did not whine about how tired she was. 

The problem was, I made the assumption that the concert was on a weekend. And wrong assumptions cause all kinds of grief, regret – and for a freelance copywriter – costly problems. 

When Assumptions Fail. Miserably.  

Making assumptions tells your prospects and clients that you don’t care enough about their business to ask thoughtful questions before beginning a project. If that’s not bad enough, making wrong assumptions causes you to do things like underestimate projects and create copy that misses its mark. 

I once assumed that a prospect requesting a sales letter wanted a one-page document – he even called his project a “one-page sales letter” – and I quoted the job accordingly.  Although I asked detailed questions about target audience and product benefits, I didn’t ask the prospect how he would be using his sales letter. 

Come to find out, what the prospect wanted was a long-form, web-based sales letter – that would be displayed on a one-page web site! (Big difference between that kind of “one-page sales letter” and the kind that is printed on letterhead stationary and mailed in a #10 envelope.) 

Moral of the Story

I honored the quote and ended up writing about seven pages of copy for a “one-page sales letter” price. I’m pretty sure I earned less than minimum wage for that project. But I learned a very good lesson: Never assume that you know what your prospect or client wants. Continue asking questions until you have a crystal clear understanding of the scope of work. 

Copywriter Confession: While I’ve become pretty good at not making assumptions when it comes to my copywritng business, I clearly have some work to do on the child side. In my defense, my daughter is a master at manipulating me to get what she wants. (My dad tells me that I was just like her at that age. I think that’s called karma.)

Nearly five years ago, I walked away from a well-paying marketing job to launch a freelance B2B copywriting career. Within two months, my freelance income was paying the bills. During my first year of copywriting self-employment, I learned many things that improved my business savvy and monthly income. Here are 10 tips I wish someone had given me before I launched my freelance copywriting business.

1. Expect to Succeed

When I quit my day job, freelance failure was not an option. My monthly financial needs had to be met and my family life was too challenging to continue working a standard eight-to-five shift. From the moment I made the decision to start my business, I expected to succeed.

Why this is important: I met many potential roadblocks during my first year of freelancing. Attitude from friends and family that, as a work-from-home mom, I was really a stay-at-home mom is one example. It would have been easy to put aside my work to assume the stay-at-home mom role, but my business would probably have failed. My driven expectation to succeed kept me on track.

2. Request Half Now, Half Later

I typically invoice clients for half of the approximate project cost before getting started. This provides a steady cash inflow, especially during longer jobs, and ensures that my clients have a financial investment in project completion.

Why this is important: During my first months of freelancing, I accepted an assignment and negotiated a fee to be paid upon final approval. Although I delivered first draft copy within a week, the document sat in my client’s email inbox for weeks. When he finally got around to reviewing the copy, he requested minor revisions. I made the changes and returned the document. Then, I heard nothing.

I finally invoiced this client with a note to let me know if he needed additional modifications. Two weeks later I had a check. But the length of time between project start and project payment taught me to request half now, half later.

3. Get It in Writing

For most new clients, I create a quote that outlines the project scope, deliverable(s), estimated cost, what isn’t included and the payment terms. The client must sign this quote and return by fax or email before I begin work.

Why this is important: I once took on a sales letter project without outlining the scope. After all, how much work could it be to write a sales letter? As it turns out, much more work than I had anticipated!

My idea of a one-page sales letter was this client’s idea of a four-page direct mail piece. Because I hadn’t outlined a project scope, I felt obligated to deliver his “letter” as requested. I ended up earning less than minimum wage for this job. Now, I get project details in writing.

4. Ask Clarifying Questions

In the example above, I made assumptions about the sales “letter” assignment based on my own experiences. I didn’t bother to ask clarifying questions.

Why this is important: If I had asked more questions to clarify my clientís expectations and use for his sales ìletterî, I would have had a clearer picture of his actual needs and I could have quoted a higher price.

5. Trust Your Instinct

You have an internal guide that, when heeded, will help you make wise decisions around your freelance writing business.

Why this is important: I was working on a project for a client based on a detailed discussion with written objectives. But the writing direction just didn’t feel right. Acting on instinct, I veered from the original scope and created an entirely different document, knowing I might never get paid for this work. However, my client loved the end result and hired me to do additional work. Trusting my instinct paid off!

6. Push Delivery Dates Out When Possible

Even if I have nothing else on my plate and can easily deliver a writing project within 24 hours, I will ask my client if a three- or four-day turn-around time is acceptable. On larger jobs, I often add an extra week or so to the production time.

Why this is important: Flexible project due dates allow you to meet change and challenge by reprioritizing as needed. I recently had a client call with a copywriting emergency. Because I had delivery date buffers in my schedule, I was able to accommodate this client’s rush needs while earning a premium rate for my trouble!

7. Suggest Other Projects

Repeat business is the easiest money a freelance writer can make. Getting more work is often as easy as asking.

Why this is important: After editing web copy for a client who had his site redesigned to leverage two new products, I suggested that he hire me to write and distribute a series of press releases announcing his news. He happily agreed. Now I suggest other projects to all my clients.

8. Treat Your Business like a Business (Not a Hobby)

A hobby is something you do for personal enjoyment, with little heed paid to planning for the future. That’s why, if you’re interested in earning a living at your craft, you must treat copywriting as a business, not a hobby.

Why this is important:When I started my copywriting business, I had a clear plan for how I was going to market my services, the number of hours I needed to work each week to meet specific business milestones and how to pay my bills while building a clientele. By creating and following my business plan, I was soon earning enough money to pay my bills.

9. Put Paying Tasks at the Top of Your Daily To-Do List

At the top of my daily to-list are projects that are almost complete. (A finished project means that I can invoice for that work.) Next, are the longer jobs that I need to move forward. Non-paying work tasks are next, such as balancing my checkbook. Finally, I add personal time and household chores.

Why this is important: During one holiday season, I shirked my work for socializing and shopping. When the new year rolled around, my accounts receivable were in sad shape.

As a freelancer, if you don’t work, you don’t get paid. This doesn’t mean you can’t have lunch with friends or spend an occasional afternoon on leisure. But it does mean that billable work must be completed before the fun begins.

10. Expect Peaks and Valleys

Even if you follow your business plan to the letter, put paying tasks at the top of your list and ask your clients for additional work, peaks and valleys in your workload and cash flow are inevitable. Plan for them!

Why this is important: When I have peaks in my workload, I get up early and work weekends to catch up. I take the extra income that results from the flurry of activity and put it in my savings account. When a work lull rolls around, I indulge in a “paid vacation” by tapping into my reserves and taking a few days off to recharge.

If you are considering a foray into freelance writing or have recently launched your own business, I invite you to learn from my experience. Heeding these 10 tips could pave the way to greater prosperity!

Copywriter Confession: Although I’ve updated this article with minor revisions, it originally appeared in the July 12, 2006 issue of Writers Weekly, a fabulous e-zine for freelance writers. Three years later, these 10 tips still hold true. Heed them!