Reality Check: 7 Questions to Ask Yourself Before Quitting Your Day Job

by Patty

BeachBefore 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!

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{ 2 comments… read them below or add one }

hezy

There are actually 8. What the hell have I done?

That’s a nice picture but I figured with a son in the marines you would be just a bit older. Seriously nice article.

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Patty

What have you done, Hezy? Made the choice to live the dream, that’s what! You and Tamara both :)

(Thanks for the compliments on the post and the pic.)

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