What Nobody Told You About Being a Freelance Writer

Awkward conversations, loneliness, financial worries and more.


Dan Marticio

2 years ago | 6 min read

Being a freelance writer is pretty amazing — you have a lot of freedom over when, where and how you work. You can work on the beach sipping a margarita if you wanted (I personally wouldn’t want sand in my laptop, but it’s nice having the option).

Freelancing is often painted through a rose-colored lens. Actually working in the field, however, paints a different story. From meeting deadlines and communicating with clients, there’s a lot more to freelancing.

7 Things Nobody Told You About Being a Freelance Writer

I went through these so you wouldn’t have to. Here are seven situations/realizations (plus tips) that caught me off guard as a freelance writer:

  1. How awkward it is to follow up on late invoices.
  2. You’ll get rejected or ignored… a lot.
  3. Money anxiety will follow you around.
  4. Long-term clients are diamonds in the rough.
  5. You don’t need much upfront capital or bells and whistles.
  6. Freelancing is a lonely venture and having fellow freelancers help.
  7. Turning off “work mode” isn’t so easy.

#1 How awkward it is to follow up on late invoices.

Sending invoices is standard practice for any service-based business. You send your invoice and then you wait for your client to pay. And wait… And wait…

Three days until it’s due…

…One day left.

It’s the due date. You think about sending an email but you’ll give them until the end of the day. You’re sure they’ll get to it.

The workday is over. You go to bed hoping you’ll wake up to an email notifying you of payment. No luck.

Gosh, darn it. Now you have to send an email, but you feel like you’re being a bother.

Tip: Don’t ever feel insecure about collecting what you’re owed. State in your contract when payment is due. Consider adding a late penalty fee to incentivize timely or early payment, too. Then send an email reminder in the days leading up to the due date.

#2 You’ll get rejected or ignored… a lot.

If you want to secure steady work, you’ll need to do a lot of cold emailing and applying for freelance writing jobs. Much of your efforts, sadly, will be returned with silence or rejection.

Tip: Don’t think it’s always because of you, specifically. Many times it’s just timing. The contact is too busy. Budget cuts. Content marketing got moved down the priority list. Getting a response is often a numbers game — you might need to send a lot before you finally get a favorable response.

#3 Money anxiety will follow you around.

The feast and famine struggle is real.

Unlike a traditional job, a freelance writer’s income can fluctuate monthly. One profitable month, you’re over the moon. The next month, dread creeps in because your schedule is too free.

Money is always on my mind and it causes me anxiety. Tons of it.

I’m fine now, but will I have enough work next month?

My income is so unpredictable. It’s hard to budget for savings, retirement and investments.

This was such a slow month. What if it keeps going on like this?

Tip: Understand your finances. Identify the base minimum amount you can survive on for one month — if you hit that number, you know you’ll get by. Next, build at least three months of savings to provide a financial buffer during slow times. Ideally, you should have this savings net before you even consider quitting your day job.

#4 Long-term clients are diamonds in the rough.

Retainer clients are clients you work with on a long-term basis. Typically, you’re paid a predetermined amount for providing a certain amount of deliverables, such as four blog posts per month.

The great thing about retainer clients is they offer steady income. Unlike working one-off jobs, your income from retainer clients provides predictability. This can help alleviate some income anxiety.

Tip: Position yourself as a long-term investment: If a client enjoyed working with you once, ask if they’ll set a retainer agreement with you. In exchange for your services, they receive a steady stream of high-quality blog posts to expand their content marketing strategy. Bonus: the time spent seeking more work is used to deliver better quality work.

#5 You don’t need much upfront capital or bells and whistles.

When starting a freelance writing business, procrastination by perfection is alluring. You want the perfect laptop, the right desk setup, a 1080p webcam for video calls and cool software for managing projects and clients. Oh, and don’t forget about a sweet website setup.

In reality, all you really need is:

  • Laptop/desktop
  • Good wi-fi
  • A digital portfolio (ideally with a self-hosted website, but you can get by using a free platform)

I spent a lot of money using a website building service with an annual subscription. I also paid for a music service for boosting productivity. I didn’t need all of this when I was just getting started.

Tips: Start lean and invest in your business as you go. The earliest stages of your freelance writing business should be spent building your portfolio. As your writing samples increase and you start making real money, then you can consider investing money back into your business.

#6 Freelancing is a lonely venture and having fellow freelancers help.

I don’t know any people in my IRL circles who do what I do. Many people have coworkers they can share office camaraderie with. Freelance writers don’t get that.

And sometimes, it can feel lonely. You still have friends and family, yes. But it’s nice having companions who do what you do and can relate to the struggles you face, too.

Tip: Reach out to other freelance writers. I’ve made a conscious effort to connect with fellow freelancers and writers. We check in on each other, ask how we’re doing and even send leads to each other. Freelancing doesn’t have to be an island. Build bridges, grow your network and develop friendships.

#7 Turning off “work mode” isn’t so easy.

One thing I miss about having a day job is the clear separation between your work and personal life. When you leave the office at 5:00, you’re done for the day. You can enjoy your downtime. And if you ever get sick, you often have co-workers who can cover you.

It’s not as easy for freelance writers. You’re a one-person business. That means you’re responsible for every operation — from marketing and client work to customer service and accounting. Oh, and delivering top-notch work, of course.

It’s easy to get stuck in your inbox. You’re always on the lookout for client emails and projects are always looming on your mind.

Tip: Set boundaries for yourself and clients. Create work hours and stick to them. Consider setting “email hour” — a specific time block for handling emails so you’re not in and out of your inbox throughout the day. Remember to create boundaries for your clients, such as how long they have to request revisions or the times you respond to emails (hint: you don’t respond at midnight).

Freelance Writing FAQs

Why do freelancers fail?

Freelance writers often fail due to a lack of systems and preparation. Without the right client onboarding systems, freelancers may lose out on potential work. When project management skills are absent, projects fall through the cracks. And if freelancers aren’t prepared for the responsibility of client work, their businesses will often collapse.

What could be the disadvantages of freelancing?

Inconsistent income is a major freelancing con. Since it fluctuates each month, financial planning is often difficult. Also, freelance writers miss out on employer benefits, such as a 401k and paid time off, often available through traditional employment.

How do you know if freelancing is for you?

Motivated self-starters tend to find more success in the freelancing world. Since freelancers are responsible for managing their schedules and clients, they’ll often need good organization and time management abilities. In addition to sharpening your writing skills, you also need to learn business skills to encourage growth and profitability


Created by

Dan Marticio

Dan is a freelance writer specializing in small business and personal finance. He works with FinTech and B2B companies and has written extensively about small business, from startup guides to payment processor reviews. Hire him to write for YOU at







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