Whether you’ve dipped your toe in freelance writing or you’re an intermediate writer, you may have considered quitting your day job to freelance full-time.

When I started freelance writing, I did it intending to eventually leave my 9 to 5 — and I did. Being my own boss was incredible. I could sleep in, take 90-minute lunches and schedule vacations without needing PTO.

But the initial rush and luster faded when some stark realities kicked in. Learning how to manage your money… Balancing multiple projects. And understanding that working on your business is just as important as working in it… I had to deal with these challenges as they came.

And it was hard.

To ensure you’re fully prepared for the transition, ask yourself these questions.

7 Questions to Ask Before Quitting Your Job For Freelance Writing

1. Do you have a clearly defined niche?
2. Is your portfolio and website marketing you properly?
3. Are you acting like a business owner?
4. Do you have a financial plan?
5. Do you have work in the pipeline?
6. Will you be leaving your job on good terms?
7. Are you willing to assume the risks of self-employment?

#1 Do you have a clearly defined niche?

Are you a specialized writer or are you a generic wordsmith? While writing across the spectrum opens the work pool, you may be stuck working on low-paying projects. That means increasing your volume (more time and labor) to make ends meet. If you’re not careful, you may wind up working more hours than your day job.

Choosing a freelance writing niche has its advantages:

• Higher expertise = higher rates
• More experience = write more quickly and accurately
• Easier to market yourself

When picking a niche, consider your interest, experience and background. More importantly, confirm there is a market demand for that niche. Writing within a niche where there’s no money means you make no money.

#2 Is your portfolio and website marketing you properly?

Your freelance writing portfolio should always be future-facing. That means continuously updating your writing samples with higher-quality and more relevant writing samples (writing within one niche helps ensure all your writing samples maintain relevancy).

As you gain more experience, you should also be updating your website with testimonials and case studies. Look for other ways to level up your website — invest in a compelling layout and build your brand visuals (font, color, logo, etc.).

Your website and portfolio are more than storage for your past work — they are real tools that should be working for you to secure future work.

#3 Are you acting like a business owner?

Learning how to go freelance is more than being a good writer — you need to be a business owner. That means working in your business and on your business.

Do you have a process for onboarding new clients? Are you setting aside money for taxes when clients pay your invoice? How about creating a system for pitching prospective clients?

Look at your professional habits. Do you find yourself procrastinating and submitting work last minute or possibly missing deadlines? Before leaving your day job, build the discipline needed to operate your freelance business full-time.

#4 Do you have a financial plan?

When figuring out how to prepare for freelancing, start with getting your financials in order. When you decide to do freelance writing full-time, income stability is often the tradeoff. To hedge risk (as investors would say), save at least three months of living expenses saved up before quitting your day job — this will offer some relief during slow months and emergencies.

Make sure your freelance writing income is enough to sustain you. Ideally, you should be making equal to or more than your day job. If you’re not making enough, gain more experience and increase your freelance writing rates so you can afford to live on them.

#5 Do you have work in the pipeline?

Client retainers are useful for providing stable, predictable income. If you’re working one-off clients, try convincing them to sign a three-month (or more) retain with you before quitting your day job.

Before I quit my day job, I had two client retainers. I had my savings built up and I had comfort knowing I would have revenue coming in within the next few months. Also, retainers if you’re easily anxious about your finances, this stability offers some peace of mind.

#6 Will you be leaving your job on good terms?

Don’t burn your bridges. Make sure you give your employer at least two week's notice (ideally, more) before going freelance full-time. Also, offer to help facilitate the transition by helping train your replacement.

Freelance writing isn’t for everybody. It’s tough running a business and income insecurity can be stressful. If you realize it’s not for you, you have your old job to possibly fall back on.

#7 Are you willing to assume the risks of self-employment?

When you’re self-employed, you have total responsibility. You have the potential to build a highly lucrative enterprise, or go broke. If you’re not a self-starter that delivers high-quality work while simultaneously nurturing business growth, quitting your day job may be a bad idea.

Leaving your corporate job to freelance and enjoy life on your terms sounds romantic… until the well goes dry. Always weigh the freelance writing pros and cons before making your decision.

Freelance Writing FAQs

Should I leave my job and start freelancing?

If you desire income stability and you’re not a self-starter, it may be best to stay at your day job. Freelance writers that possess discipline, business management skills and a willingness to learn and adapt are better suited to freelancing full-time.

How do I quit my job and be a freelancer?

First, ensure that your freelance writing business has the right systems and is producing enough revenue to support the lifestyle you desire. Consider choosing a niche, building an impressive writing portfolio and securing client retainers for stable income. Also, be sure to have a savings buffer of three months’ living expenses to tide you over during slow months.

Can you make a living off freelance writing?

Yes. Many full-time freelance writers generate enough revenue to support their lifestyles. Financially successful freelance writers tend to be self-starters nurture both their writing and business management skills.

How long does it take to start making money as a freelance writer?

Beginner freelance writers can potentially earn money after completing their first freelance writing job. As they grow their writing portfolio and experience, they can eventually work with higher-quality clients that offer better pay.

How do I break into freelance writing?

If you already possess excellent writing skills, first focus on building your freelance writing portfolio. You can create relevant writing samples (usually unpaid) through guest blogging and pitching to Medium publications, which you can then list when pitching freelance writing clients.