Reality Check: 7 Questions to Ask Yourself before Quitting Your Day Job By Patty Harder

Reality Check: 7 Questions to Ask Yourself before Quitting Your Day Job By Patty Harder

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 book, The Well-Fed Writer, cover-to-cover. Twice. I built a website and created an online portfolio. I converted my rarely-used formal living room into an office. And I planned my business implementation strategy.

These early efforts paid off. Within 90 days of starting my business, I had replaced my full time income. Whether you’re planning to start a 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 or a reduced rate to a non-profit organization or a friend with a small business. Hire a writing coach. 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 cashed 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.

3. Do you have the full support of your immediate family?
Reality Check: Starting a freelance writing business is risky. There’s a possibility that you’ll burn through your savings without getting your business off the ground. It’s important that your immediate family understands this risk 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.

Whether you will be working as a freelance writer in your current company’s niche or in a different market, it’s important to understand that, when you quit your day job, you may be severing that tie forever. If this happens, 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 website 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 a full time freelancer.

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

Reality Check: Working for yourself from home isn’t always easy. Many 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 daytime 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!

Patty Harder is a freelance copywriter and marketing consultant in the Seattle area. In between client projects, Patty shares her insider secrets for launching growing and managing a freelance writing business at