Becoming a Freelance Writer: How to Smoothly Transition from a Full-time Job — An In-Depth Discussion

About a week and a half ago, I received the following email from an aspiring freelance writer.

Hi Yuwanda! Hope Jamaica and business are treating you well.

I am in retail right now and I just graduated college. Currently, I am looking for a job as the money in retail is not enough to pay off debt and eventually move out of my mom’s house. I also want start freelancing on the side of my new job. How do I market myself so I don’t confuse my target audience? I want to use LinkedIn for part of my marketing but I was told by my job hunting mentor that I should use LinkedIn. [sic]

As you can see, she wants to keep her job while freelancing on the side. This question gave me the idea for this post, which I wanted to take in another direction because it’s one a lot of freelancers struggle with.

Also, I asked several freelancers to contribute to a book I was contracted to write on freelancing. Cathy Miller – a long-time freelance writer – told why she made the transition years ago. You might not want to do what she did – let’s just say she quit suddenly. She gave some excellent tips for how to transition – and possibly take your old employer as a new client when you venture out on your own.

When I first started freelancing years ago, my old employer was my biggest client for almost a year after I left. They remained a client for the first few years, which made the transition to freelancing so much smoother. But there are drawbacks to this as well, which I’ll address at the end of this post.

7 Things You Should Do Before You Leave Your Job to Freelance Full-Time

So, following are seven things I would do to make the move from working full-time to freelancing full-time if I were to start today. I did it so wrong years ago, it wasn’t even funny. But thankfully, it’s all worked out. Live … learn, no?

1. Write a Business Plan

It doesn’t have to be a thirty page, venture-capital worthy plan, but you’re starting a business. Writing a business plan will force you to get in that mindset. You’ll be able to flesh out what niche you want to target, research fees and services, know how much your business expenses are going to be, and how much you’re going to need to earn to meet your financial obligations month in and month out.

How to transition from a full-time job to freelancing full-timeHere’s a really simple business plan for freelance writers. It only has three sections that need to be addressed – and you’ll be on your way. It truly doesn’t get more simple than this.

FYI, here’s some great advice from other freelancers on some areas to address in your business plan for your freelance business.

Getting back to finances …

2. Financially Plan Your Exit

Figure out how much you need to cover ALL of your bills – including your new business expenses – for one year, and start socking it away. If you do any research online, you’ll find that many experts recommend having anywhere from three months to nine months’ worth of expenses on hand.

Of course, the amount you need will vary depending on what your expenses are, and you may be the type of person to feel secure with less than a year’s worth of expenses in the bank. So why do I personally recommend a year? It’s simply because the bigger the stockpile you have, the more secure you will feel being out on your own. And, consider this …

It may take you a month or two to land your first gig. Then, it may take another month or two to get paid for that job. Right there, that’s a possible four months of no money coming in. And let’s just say you had six months’ worth of a cushion – that leaves you with only two months of money in the bank.

With this mindset, you’ll undoubtedly start to panic, especially if you’ve never freelanced before and you have dependents. With this type of mindset, it’s hard to focus on and grow a business. Working out of panic mode may be good for some (and sometimes it’s just the kick in the pants you might need), but why start your freelance writing career that way.

With eight more months’ worth of expenses in the bank, you still have time to evaluate what you may be doing wrong and fix it. OR, to wait out a slow season. OR to just have to patience to know that you’re doing everything right – it’s just going to take time (and you can afford to wait it out).

Here’s some great insight on how to save enough money to quit your job, which brings me to my next point …

3. Get Set Up before You Quit

All of your behind-the-scenes prep work should be done before you quit. This includes doing a business plan, getting your website up and going, deciding on rates, setting up your home office, and deciding which services you’re going to offer.

On day one of your freelance writing career, you should be able to push the “Go” button – and start marketing for clients. This brings me to the next tip …

4. Start Freelancing before You Quit

As in, get clients, complete jobs, invoice clients and get paid. This serves a couple of purposes. First, it will reinforce the fact that your dream is really possible, and secondly, it’ll give you a dry run of what’s working/not working with your business processes.

Some Things You’ll Learn When You Start Freelancing While Working Full-Time

Even having completed one job will give you some insight into what it’s going to be like, ie:

How clients will contact you (eg, email, Skype, phone);

What they will say/want/need;

How they’ll act throughout the process;

What types of feedback you may receive;

How you’ll respond to clients throughout the process (and what you may need to tweak):

What you’ll charge;

How they’ll react to what you’re charging;

How you’ll invoice them;

How long it’ll take to get paid;

How they prefer to pay;

Whether or not to charge late fees if they’re late paying;

How to “chase” your money if they’re late paying; and

So much more.

Starting to freelance is like driving somewhere you’ve never been before. You may have directions, but until you’ve traveled the road, you have no idea of what kind of potholes, smooth patches, traffic lights, traffic flow, etc., you’re going to encounter. Once you’ve driven it though – even once – you gain insight into what it’s like, which gives you more confidence as you traverse it, right?

5. Get Out of Debt

Circling back to finances for a bit, get out of as much consumer debt as you can before you start to freelance. While it may not be possible to pay off a mortgage or your student loan debt, you try to pay off:

Credit cards;

Car loans (or trade down to a vehicle you can pay cash for, which lessens your insurance payment); and

Any personal loans (eg, that one to your mother that’s been outstanding forever).

Having only your rent/mortgage and utilities to pay for should be your goal, for two reasons: (i) again, you’ll feel less stressed with a lighter financial load as you enter the freelance world; (ii) it lessens your monthly outlay, which means you have to save less to meet your goal of one year’s worth of expenses in the bank; and (iii) it gets you on the road to fiscal responsibility.

Freelancing is an up-and-down existence. There’ve been months where I’ve broken five figures, and there are months where it’s been in the low threes (as in only earning a few hundred dollars). Yes, it’s true!

That’s why I no longer get excited when I have a really good month, because I know that there will be those slow months and it’ll all even out at year’s end. It’s also why I’m a prolific saver. Freelancing taught me this. I’ve never been one for designer clothes and stuff like that – thank goodness. My weakness has always been travelling – and I will spend money on hair (hey, a sista has to have at least one spending vice!).

But I have no consumer debt. I pay off my credit accounts each month and for big purchases, I have to see my way to paying it off within three to six months – or it has to wait.

I’ve been in debt up to my eyeballs before. I’ve had to borrow from friends and family to pay my bills, and let me tell ya, it’s not a good feeling. I hated it. I was brought up to always pay my own way, so I practice living below my means so that I will never (knock wood) have to go down that path again.

And when you don’t owe anybody anything, you’ll be much more hesitant to get back in debt again. As I was telling one freelancer friend recently, it’s one of the reasons I moved to Jamaica. I made some financial mistakes that I’m recovering from because retirement is literally right at my doorstep (I turned 50 this year). It’s no longer something that’s years away that I don’t have to worry about now.

Always, always, always have a financial cushion – you’ll sleep better at night, trust me.

6. Apply for Credit

It’s really hard to get credit when you freelance, so while you have a steady, full-time job, apply for some credit – that is to be used ONLY in an extreme emergency. Having an extra credit card or a line of credit in the form of a home equity loan can be extra financial padding – over and beyond the years’ worth of expenses in the bank – if you should need it.

After you quit, this door will probably not be open to you (at least for several years until you can prove a steady income – and even then, it can be difficult, unless you’re earning goo gobs of money). So be sure to apply for credit before you quit your job. And again, don’t use it. It is JUST for extreme emergencies.

Here’s some insight on how to build credit as a self-employed contractor/freelancer. FYI, I disagree with incorporating and building credit in your business name. In my opinion – and experience – it’s not necessary to incorporate as a freelance writer. If you want to, that’s fine, but it’s not a necessity, as I discuss in this free ebook on starting a freelance writing career that I contributed to from eJunkie, along with ten other freelancers (see #IV).

As long as you keep your personal credit good and you can prove your income, you will have no problem getting – and keeping – a good credit history.

7. The Right Way to Leave Your Job

When you do decide to leave your job – no matter how much you may hate it and can’t wait to leave – leave in a professional manner. Give proper notice; more if your help is needed on projects until your employer has a new employee in place.

Offer to make the transition as smooth for your company as possible. Offer to train your replacement, stay late to tie up existing projects, work weekends to meet deadlines, etc. All of this will be remembered by those you leave behind.

Also, when you leave, be sure to sign up to for the company newsletter, to their social media accounts, etc., so that you can stay in contact with previous co-workers and company happenings IF you want to take them as a client.

This way, you can stay abreast of what’s going on and keep your foot in the door “unobtrusively” by sending along congratulations when promotions happen, when someone gets married or has a baby, when the company makes a great acquisition, etc. Then if/when you decide to approach them as a freelancer, you’ve left in good standing, which speaks volumes about how you’ll handle them as a client.

3 Tips for How to Handle Your Employer after You Leave Your Job

Badmouthing a Former Employer: Never, ever bad mouth a previous employer, especially on the web. What you put on online stays there forever in one form or another, and if a potential client ever discovers that you’ve done this, their thinking may very well be, “If she spoke about them like that (even if everything you’ve said is true), then how will she talk about us if things ever turn sour?”

Just don’t do it. If you don’t want a previous employer as a client, leave in a professional manner – as discussed above – and leave negative vibes behind.

Handling the Inevitable, “Why Did You Quit” Question: When someone asks why you quit, just say something to the effect of, “I wanted to start freelancing; it was time to take my career in a different direction. I’m glad I gained the experience there – it helped better prepare me for my journey now.”

Again, keep it moving. Even if they were horrible to work for and you hated every second and you want to scream from the rooftops about how inept they were as an employer (barring serious issues like sexual harassment and discrimination (sexual, racial, age, religion, etc.)), just focus on your exciting new beginning. Leave the negative in the past.

Meeting Ex-Coworkers “for Drinks:” This can be a trap waiting to bit you in the bazooka; not in the sense that you or your ex-coworkers intend for anything bad to happen, but you know how it can go.

You meet up with a few of your ex-coworkers who are friends, and inevitably the conversation turns to the job – their current job; your ex-employer – and you all start commiserating about the good, the bad and the ugly.

Watch out for this. Inevitably something you say can filter back to your ex-employer. So if you keep in contact with co-workers who’ve become friends, steer clear of conversations about your old job that can turn negative. Keep it light, positive and brief because the longer you talk about an old job, the more likely you are to say something that could be construed as negative.

Freelance Writers: How to Turn Your Previous Employer into a Client

If this is your goal, be sure to leave professionally, as discussed above. Also, offer to take your old boss – and/or a few of the key people in the company who can give you work — out to lunch.

Let them know what kind of career you’re embarking on. Tailor a sales pitch specifically for them. After all, you worked there. You know their pain points better than any outsider possibly could. This is akin to having insider trader knowledge. Capitalize on it!

Caution: First off, make sure there are no non-compete clauses before you approach your old employer, or any of the contacts you made while working at the company.

And, if you do land your previous employer as a client, be sure not to rely too heavily on them as your only/main source of income. I made that mistake.

My previous employer was giving me so much work when I left my company that I got lax. I’d been freelancing for them on the side while I was working full-time with them as well, so I got lax. Then, when the work suddenly dried up, me and my partner had to scramble to find other clients.

Luckily, we kind of fell into staffing (sending editorial freelancers on site to fill jobs), so it all worked out. But it was a big lesson in diversifying. Never rely on just one or two clients for the bulk of your freelance income. You should always be marketing to bring in new client, while continuing to service and upsell existing clients on a range of services.

FYI, I discuss all of this in the free ebook you get when you subscribe to Inkwell Editorial’s newsletter, which you can do from the right-hand side of any page of the site.

Here’s some great advice on how to “outsource yourself” to your previous employer as a freelancer, and avoid some of the common pitfalls that come with doing this.


Taking an old employer with you as a new client into your freshly launched freelance writing business can be a great way to get started because of the familiarity of the work. So if that door is open, by all means, do your best to walk through it

But, if that’s not an option and you’ve taken the seven steps outlined here, you’ll still be on your way to building a successful freelance writing career.

I hope this insight helps, and good luck as you make the transition. Freelance writing is a wonderful way to make a living. Contrary to some beliefs, it doesn’t have to be a feast-or-famine existence. It can provide the financial freedom you never thought you could achieve – and on your own terms. How awesome is that!

What You Need to Know Before You Quit to Freelance Full-timeP.S.: Are you dying to quit your job to freelance full-time? This ebook is a realistic roadmap of exactly what quitting to freelance full-time is all about. A review of this ebook left on Amazon sums it up, saying in part:

This book is just what it says. It will give you a good idea of the pros and cons of becoming a freelance writer.

I really like it that the author gives a lot of personal information about her situation. After reading this book, I feel that I have a good insight into the life of a freelancer – the pitfalls as well as the joys.

P.P.S.: Did you know that you can now order any of our products (like this online freelance writing e-course) and take up to 6 months to pay? You can.

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    1. The idea of starting with a business plan is solid advice. Great tips!
      Angela Alcorn recently posted…Here’s Why Slack Communities Are Due For A RevivalMy Profile

      • Thanks Angela.

        Yeah, it’s a roadmap. I’ve never been a big believer in business plan, but as my freelance writing and self-publishing business has grown, I totally see the need and appreciate how it makes you think futuristically. Thanks for stopping by, and continued success.