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!

 Technology is amazing. Except when it isn’t.   

I do a lot of interviews for copywriting projects like case studies and white papers and I record the conversations using an online conference call service. When a call is complete, I simply download the mp3 file and email it to my transcriptionist.

This process is a huge improvement over the “olden days” when I used to hook a small micro-cassette recorder up to a landline telephone and then physically deliver the tiny tape to the transcriptionist. 

My conference call service  is super easy to use, has great customer service and, in three years, I’ve never had a problem with the system. But recently, a case study interview failed to record. (I realize now that I can monitor the recording online while on a call so this will never happen again without my knowledge.)

This was an interview with an important client of an important client, and when I realized I had no record of it, I broke out in hives. (The really itchy kind that requires multiple doses of Benedryl to control.) 

The Best Case Scenario 

After spending an entire weekend drowning my sorrows in chardonnay and fretting over how to tell my interview contact that I wasted his time (while imagining all kinds of worst-case-scenario reactions from him), I picked up the phone on Monday morning and blurted out the bad news. I explained what happened, truthfully stated that this has never happened before and apologized repeatedly. (Sidenote: never deliver bad news via email. While your voice can convey your sincere remorse, email can’t.) 

Imagine my relief when the contact said, “Well, I’m sure this won’t be the worst news I get this week. I guess we’ll have to do the interview again.” We scheduled another interview date for later that week. Tragedy was averted. 

I re-did the case study interview this morning and it actually turned out better than the original. Armed with the knowledge from the first interview, my questions were more direct and the contact’s answers were more concise. Plus, a recent development on the client’s side added a great anecdote to the story that the earlier interview didn’t capture.  

Falling on Your Sword 

When something goes wrong in your life or your business, take responsibility for it and apologize to the injured party in the most sincere way possible. Don’t make excuses like a teenager that just missed curfew. And don’t blame someone else for the issue. 

When you take responsibility for a problem by falling on your sword, an amazing thing happens. The other person will come to your rescue because it’s human nature to help others who are in pain. Excuses and blame, on the other hand, put people on the defensive and makes them question your integrity. (If teenagers would learn this early on, they would spend a lot less time on restriction.) 

But falling on your sword does not mean berating yourself to someone else. If you repeatedly say something like, “I’m so stupid for letting this happen!” you might convince the other person that, yeah, you are. Instead, apologize emphatically for the inconvenience and ask if there’s any way you can make the situation better. 

More often than not, the person will suggest a work-around (like my interview contact offering to schedule another interview). On occasion, however, the situation won’t be salvageable. If this happens, know you did your best to correct the issue and then let it go. Even if that means losing a client. 

Perfection is Overrated 

People aren’t perfect, and sometimes things happen that suck. As a copywriter and fallible human, you will make mistakes. When this happens, fall on your sword. Most of the time, you’ll be saved. But once in a while, you’ll be left to bleed out. Either way, get over it and move on.    

Copywriter Confession: Falling on your sword is actually a sales tactic used at the company I used to work for and was often used to manipulate prospects. I don’t use the tactic for this purpose and don’t recommend that you do either. As a small business owner, your integrity is everything. In the long run, sincerity will serve you better than deceit.

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.)