How to Start a Successful Freelance Writing Business When You Have a Day Job

Double exposure image of businessman holding smartphone with a row of money, coins, and analog clock

One of the biggest questions I get from new and aspiring copywriters is how to start (and work) a part-time copywriting business when you have a full-time job.

It’s a question I know intimately — because I agonized over it for years when I was making my own transition into self-employment.

In 2003, my goal was to become a full-time freelance copywriter. But as my family’s sole income-earner, I couldn’t just quit my day job. Instead, I had to build my business gradually until I could afford to make the leap into full-time copywriting.

Doing it this way, I learned a few lessons along the way that you’ll find useful. You can use these tips and ideas so you can build and run your business on a part-time basis safely and methodically.

From Fire Hydrants to Copy

Until I became a copywriter, I had been in sales for my entire professional career. I sold everything from fire hydrants (yes, someone actually sells those things!), water-main pipe, valves, and fittings — all the way to professional technology services, PCs, servers, and software.

My last job was for a small software company. I was earning a six-figure income, but I had to put in long hours to meet our aggressive sales quotas, leaving little time to work my copywriting business. Not only that, but we had just had our first child, and my wife had left her job to stay home with him.

So, basically, I had a high-pressure sales job where I couldn’t afford to slack off. My family was depending on me. I wasn’t willing to sacrifice my six-figure income … and I had very little extra time to do anything on the side.

Chicken Entrepreneurship

With all these constraints, I realized that the only way I could transition out of my day job was to launch my side business methodically and over time. So I drafted an action plan that would take me from where I was to becoming a full-time freelance copywriter over the course of two years.

The plan was based on Mark Ford’s “chicken entrepreneur” approach, which I had read about in an Early to Rise article a few years earlier. In that article, Mark explained that being a chicken entrepreneur is all about launching and growing a successful business without taking unnecessary risks.

It’s not the sexiest approach. But it was the best way for someone in my situation to safely transition into a full-time solo business.

In the context of freelance copywriting, being a chicken entrepreneur is all about keeping your job (and a steady paycheck) while you work this business to ensure that:

  1. It’s something you actually enjoy
  2. It can support your financial needs and goals. That way, if you aren’t able to make a go of it after a reasonable amount of time and effort, you can try something else and you won’t have lost too much in the process.

Plus, you’ll still have your job and your paycheck. And of course, if you’re successful, this approach is a great way to get out of a dead-end job without having to starve for a year or put your family in financial peril.

In June 2006, after 27 months of learning B2B copywriting in earnest and working my copywriting business part-time, I had enough clients and enough work to quit my day job!

Finding the Time to Work Your Business

There’s one aspect of this whole thing that’s going to be difficult, no matter how you go about it. And that’s finding the time to work your copywriting business. Fact is, you’re going to have to find the time. This means you’re going to have to look at how you spend your week now and make some tough decisions and tradeoffs.

In my case, I would either wake up an hour earlier every day or put in two or three hours at night after our son was in bed. I would also work Saturday mornings from about 6:00 am until noon. I tried to keep Sundays off limits, but the occasional deadline meant putting in a few hours Sunday afternoons.

You may also consider approaching your employer about either telecommuting and/or working four 10-hour days rather than five eight-hour days. Such creative arrangements can free up a lot of time to work your business. Telecommuting, even if it’s only one or two days a week, can help make you a heck of a lot more productive, since you’re not constantly interrupted by colleagues who want to catch up about last night’s ball game or office gossip.

So, if you can get eight hours’ worth of work in five or six — and skip a two-hour commute — that leaves you with some time to work on your business. Just make sure to always be ethical about this. You have to be fair to your employer. Don’t work on your own thing while you’re on the clock.

Increase Your Productivity

As you find the time to work your part-time business, you’ll also have to find ways to increase your productivity. That means staying focused when you’re working. No email, no Facebook, no Twitter, no phone. If you’ve dedicated 8:00 p.m.-10:00 p.m. Monday through Thursdays to your business, you have to work exclusively on your business during those hours.

What worked best for me was having a list of tasks already written down before I sat at my desk — it would help me dive straight into the work. I would also give myself a 20-minute break at the end of each hour to clear my head. Additionally, I would set weekly objectives to work toward in terms of sales letters mailed to prospective clients, outreach to people in my network, progress on my own website, and so on.

Prospecting for Clients When Time Is at a Premium

There are dozens of ways to prospect for clients. But the challenge for part-time copywriters is finding prospecting methods that won’t interfere with their day jobs. There are two great ways to do this: prospecting emails and tapping your network.

Short and personalized prospecting emails are very effective. They’re also easy to produce and send.

Also, reaching out to people in your network is another great (and proven!) way to land clients when time is at a premium. Not only do they trust you already, but it's often easier and less stressful to approach people you know than it is to contact complete strangers.

Plus, if you're just getting your freelance career started, talking to friends, colleagues, and relatives about what you do enables you to develop and refine your message in a less-threatening environment.

Start with the people who know you best. Even if your closest friends can't take advantage of your expertise, they may know someone who can.

Handling Prospect Inquiries During the Workday

The best way to manage prospect inquiries while at your day job is to use your smartphone. This will enable you to respond to prospects and clients faster while giving you a temporary business phone line. You’ll want to set up a simple voicemail greeting and have the unit pick up messages until you can get back to people during your breaks and your lunch hour.

Once you make the transition to full-time freelancing, you can then change your official business phone number to a landline or you can simply keep your mobile as your main number. I know many freelancers who have opted for the latter because they prefer the portability of a mobile phone.

How to Manage Client Expectations

How do you manage your limited time and your clients’ expectations when working both a full-time job and a part-time copywriting business? A lot of aspiring copywriters get hung up on this for no reason. I was one of them!

Here’s the deal. Clients are already used to freelancers telling them when they can take on a project and when they can deliver a draft. So the fact that you can’t turn around that case study or white paper in one week shouldn’t trouble you. If you can’t do it that fast, you just can’t. A full-time copywriter with a solid workload would face the same dilemma if she faced a similar request from a client.

Your schedule is what it is — limited. Accept it. But be very diligent about keeping track of your availability and current commitments. Don’t over-commit to anyone. Keep an updated schedule with all your current and upcoming projects (I keep mine in Excel) and be honest with yourself about your availability. Squeezing in a 20-hour project into 12 hours of available free time is a big mistake. Better to say “No” than to miss the deadline or submit subpar work.

Staying Motivated

One of the biggest obstacles part-time copywriters face is staying motivated. Especially when their goal (quitting their day job) seems so far away!

There are a few things you can do to stay on track. First, try not to focus too much on the big goal (say, the date by which you’d like to quit your day job). While important, this big goal can seem bigger than life when you’re just starting out. Instead, focus on shorter-term goals. Break down your big goal into yearly, monthly, and weekly milestones and objectives. And focus on reaching those.

Celebrate these little wins with pride. Let the excitement of finishing your website or completing a small copywriting project — even if it’s for a friend — drive you to keep going.

Second, make sure you have the full support from your family. Working a side hustle while you keep a full-time job is challenging. You’re going to have to sacrifice some family time to reach your goals. And that’s going to require that your spouse, kids, and other loved ones understand what you’re doing it and why you’re doing it.

It’s okay if they don’t fully get it at first. But try and get as much support as possible. Then, share your successes with them as they happen. It won’t be long before they realize that you’re fully committed to changing things for the better — and that you’re getting tangible results. Seeing them excited will feed your enthusiasm and reassure you that you’re on the right track.

Third, if your goal is to eventually quit your day job, avoid the temptation to spend your part-time income earnings. Try to save all your business income (after taxes and expenses). Stash it away in a savings account of some sort. Seeing your savings grow will be a huge motivator. It will make all the hard work and sacrifice feel worthwhile. Plus, it will give you the cushion you need to confidently make your move when the time is right. (There’s nothing like money in the bank to help you sleep well!)

Above all, never forget why you’re doing this. If you have good enough reasons to build your side hustle, you’ll persevere and succeed.

What questions do you have about getting started while you work at your day job? Please share with us in the comments below so we can help.

Editorial Note: Your road to freedom starts with solid training. And Steve Slaunwhite’s foundational B2B copywriting program not only outlines everything you need to know about writing for the massive B2B industry, he tells you how to land good-paying clients also. Get all the details here.

Modern B2B Copywriting

Modern B2B Copywriting

Learn everything you need to know to succeed as a B2B copywriter from marketing your services to writing copy and everything in between. Learn More »

Click to Rate:
Average: 5.0
Published: November 29, 2018

1 Response to “How to Start a Successful Freelance Writing Business When You Have a Day Job”

  1. I work full time in healthcare which I find is very challenging; often after a 12 hour shift, it is very difficult to think outside of the events that I have come across during my shift.Your article helped me to feel as though I am moving in the right direction along with giving extra guidance, I question if a blog is a good place to begin on a new website or will this sidetrack me from my goal of becoming a copywriter? Much respect, Loretta


Guest, Add a Comment
Please Note: Your comments will be seen by all visitors.

You are commenting as a guest. If you’re an AWAI Member, Login to myAWAI for easier commenting, email alerts, and more!

(If you don’t yet have an AWAI Member account, you can create one for free.)

This name will appear next to your comment.

Your email is required but will not be displayed.

Text only. Your comment may be trimmed if it exceeds 500 characters.

Type the Shadowed Word
Too hard to read? See a new image | Listen to the letters

Hint: The letters above appear as shadows and spell a real word. If you have trouble reading it, you can use the links to view a new image or listen to the letters being spoken.

(*all fields required)