The internet is flooded with tips on getting started as a freelance writer. It’s an exciting transition, after all!

But when we talk about freelancing, I’ve begun to notice how disproportionately focused the offerings are on that first client, that early coffee shop hustle, that victorious job-quitting moment…

We’re saturated with information about the early milestones of freelance writing. This is likely because freelance mentors are constantly catering to new waves of freelancers who are just getting their feet wet—and there’s nothing wrong with that!

But there’s a part of freelance writing that folks talk about a lot less: How it feels when you’ve overcome that threshold of being a newbie and have put in almost a decade of your life freelancing.

What does the “light” at the end of the new freelancer tunnel really look like? I thought I would provide some insight as I celebrate my own freelance milestone this year. I got started in 2009, and it’s been a wild ride, but I dare say it has afforded me some wisdom to impart.

So here’s what it looks like from my end of the spectrum.

Read on to learn some of the things no one tells you about being an experienced freelance writer.


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Rejections aren’t the end of the world.


Events in your freelance life become less emotional because you learn to separate yourself from your work.

You think more like a business owner and less like a lone warrior trying to defy the odds of the 9-5 path originally laid out for her.

You chill out on that whole idea, in fact.

This means the urge to follow up several times or chase down would-be clients ceases to exist.

When a client goes MIA, you file them away and move onto the next prospect. You’re not reliant on one opportunity carrying you through to the next month because you’ve set your business up accordingly.

Long story short? It isn’t personal.

There’s another side to this coin as well.

Things working out in your favor (like landing a big contract) doesn’t feel like a reason to bust out the champagne—unless you’re like me and you just normally have champagne at the ready. ๐Ÿ˜‰

You don’t get all hyped up over a new client. You’re used to landing your dream gig over and over.

Which is good, because hyping up clients can lead to an unbalanced working relationship, which leads me to the next point…


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You might become a bit of a diva.


Working over the weekend? Overnight turnaround? Unpaid tests before a project begins? Haha. No.

When you start to feel like a business owner and not just a floating no-man’s employee who gets to work at the cafe sometimes, you’ll instinctively refuse to work outside of the terms you’ve set.

You may refuse to work with certain software or with a certain process—not because you’re being difficult, but because you have your own processes nailed down. There are some things you’ll meet in the middle on, but some things you won’t.

Working relationships may involve conversations where you explain your process to clients. You won’t feel bad about it or worry about “losing” them for being specific. It’s just the way you do business.

This is a natural part of becoming experienced in any industry, except in freelancing there are no promotions or title upgrades to signify that you get to call the shots more often.ย You’re in charge of recognizing your own seniority and adjusting course as you evolve.

I did things in the beginning of my career that I would never do now. It’s called learning from your mistakes! But it’s also called reaching the next level.

I’m more skilled, more experienced, and more responsible than I was when I started—like, big time.

As a result, you begin to teach clients how to treat you with your own actions and boundaries.


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Raising your rates doesn’t feel wrong.


Something people skip over when they talk about freelancing—since so much advice is targeted toward brand new freelancers—is that as you learn through experience, you unconsciously perceive yourself as more valuable.

That’s why having “I’m raising my rates” conversations doesn’t leave you with a pit in your stomach. In fact, it feels empowering. It feels refreshing.

You may even prefer to have those conversations in real time over the phone than to fire off an email and hope for the best.

You know your high-quality clients recognize your work and are going to pay those increased rates. If not, you’ll part with them graciously and no harm will be done. It’s not personal. It’s business (are you noticing a theme?).

You won’t worry about losing work to freelancers with cheaper rates because you know what you bring to the table.

As for bottom of the barrel rates, they won’t be a part of your world. You won’t even register clients who are seeking out the cheapest freelancers. They’re not your target client, after all.


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Communicating with clients isn’t stressful.


Phone anxiety is real in my generation, and I used to feel it hard.

It doesn’t help that I have anxiety disorder, but one of the ways I’ve built up my confidence and reduced my anxiety is through my freelance career.

Each milestone in my career has afforded me more confidence to have all kinds of conversations with clients. Each year I felt more comfortable with clear, effective communication through any channel, even the dreaded phone.

Whether I have to reach out for more information, disagree with feedback, question a part of the process or make a suggestion, I feel calm and collected when doing so.

It’s a far cry from the early days when I used to speak far too loud, pace nervously, and let my insecurities show each time I spoke to someone I was working with. It was as if I felt I was tricking them into paying me and somehow, someway, the jig would be up and they’d find me out.

Yes, good old impostor syndrome!

You can look forward to mostly kissing that goodbye. It still pops up when big opportunities and challenges arise, but it’s more easily managed as you work through these experiences.


Dreading Your Next Client Call? 6 Tips to Feel More Confident on the Phone


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“Feast or famine” exists, but you’re ready for it.


The ebb and flow of freelance income is a legitimate fear that keeps some from freelancing at all.

After you’ve taken the leap and been through a few of those dreaded famine periods, you realize that you’re resourceful enough to make it work.

You also learn (rather quickly) how much you need to have saved for those less-than-abundant seasons, should things take a turn.

Having savings and feeling confident about your problem-solving abilities can also help you make confident decisions during more fruitful periods.

For example, when you decide to raise your rates, you might do so with more confidence knowing you won’t be hung out to dry if that client declines and ends your relationship.

(This usually doesn’t happen by the way—clients like having long-term relationships with freelancers they trust and won’t easily let them go once that bond is formed.)

New work pops up more often, too.ย You begin to have your pick of projects and the universe seems to send relevant “ideal clients” your way.

In reality it’s part quantum manifestation, part intentional setup of your entire career to attract a certain kind of client.

The point, though, is that one of the biggest reasons people are afraid to freelance becomes sort of a non-issue.


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“Interviews” are just conversations.


Forget about being “interviewed” for opportunities, or for prospective clients to quiz you on how much you know.

The traditional model of competing against other freelancers for open positions becomes a thing of the past.

You’re a business owner now, and by the time you get on the phone with someone, they are already excited to work with you—or else they wouldn’t be wasting their time with a phone call.

You’ll find that conversations with prospective clients just feel like conversations between two business owners.

You figure out whether they are a good fit for you (and vice versa).

By the time you decide to work together, it feels like a beneficial situation for both parties, rather than one person trying to gain employment from the other.

This evens the landscape and ensures you only choose professional relationships that are compatible with your values and goals.


Read This Before Your Next Freelance Writing Job Interview


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You’re more valuable than you know.


You will get to a point where some clients know less about the industry than you do, and this is not because they’re lacking.

It’s simply because your job is to work with many different clients, giving you an invaluable bird’s eye view that people don’t get when they stick with one company.

You’ll know how competitors work. You’ll have tried different strategies and software to achieve certain results. You may even know terminology that is new to your client.

Your pool of knowledge will become a major selling point and will increase your value exponentially—especially if you begin to offer light consulting as part of your package.

I started doing this after realizing I couldn’t keep my mouth shut if I saw my client doing something counterproductive to their goals.

Offering my input on things outside of copywriting has strengthened my working relationship with many clients over the years—for example, UX-related call outs that impact the effectiveness of my copy, or even logo and design feedback if it feels off brand and I have a potential solution.

The key is not to call things out that are “wrong” but to offer constructive, actionable suggestions.

Of course, there are business owners seeped in their industry for a lifetime who will be true gurus in their field. They become your mentors.ย But others will be branching into new territory and will welcome your feedback in many areas of the operation.

You’ll learn from clients and they’ll learn from you.

As a moving piece in the puzzle, shifting from one business to the next, you’ll start to have a professional advantage in more of your relationships.


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You still get bad reviews. Ouch.


Experience level and skill won’t always equate to clients raving about you with cartoon hearts in their eyes.

In fact, sometimes you’ll be humbled by a client coming back with a “meh” response to something you poured your heart and soul into.

Sometimes you’ll be shocked by your work being completely misunderstood or your strategy disregarded.

You may think you’ve written the most amazing copy of your career only to have someone question your abilities or write you a terrible review.

Case in point? After wrapping up a project with a difficult client, she had her assistant write to me and tell me I had “lower than high school” level writing skills.

I sat in front of my screen, in shock, unsure how I was going to carry on with the rest of my day.

I didn’t feel sad, I felt angry. I couldn’t figure out whether she was trying to insult me or she really thought my writing was bad.

For context, she was asking for extremely flowery language which, in my mind, would have been like “lower than high school” level poetry being scrawled by a love sick tween.

When I wrote copy that was romantic, but restrained and elevated, she wasn’t having any of it.

In the end, I just let it roll off. I even laughed about it with my writing group.

Humble moments are healthy—and they never disappear, no matter how much time you put into becoming a respected freelancer.ย You learn to live with them and learn from them whenever possible.


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Working remotely isn’t novel anymore.


Aah, the work-from-anywhere life.

There’s no doubt that freelancing first appealed to me because I wanted to work from home, and that desire evolved into working from cafes around the world.

There was a time when my driving force to keep freelancing was the ability to travel while working.

I mean, is there anything more instantly envy-inducing than posting a tropical photo in the middle of winter with a laptop in it?!

There’s an entire sub-niche of the stock photo industry dedicated to replicating the digital nomad dream.

Anyway, these days I know that the purpose behind my freelance quest is freedom in general—especially the ability to work from home when I’m having a lot of anxiety.

The shimmering promise of remote work fizzles away to expose the reality pretty quickly.

Working remotely presents its own challenges, from losing track of hours to rampant distractions and spotty Wi-Fi.

You’ll find yourself cringing through client calls while the neighbor’s dog is howling, getting distracted by a pile of dishes, and then sitting down to work just in time for the 3pm bout of existential dread you forgot was coming to call.

And yes, after spending 5-10 hours alone each day at your laptop, you’ll have days where you may crave the camaraderie that 9-5 folks enjoy.

You learn how to work in a way that isn’t detrimental to your well being, but I’d say this is one of the things even veteran freelancers struggle with.

Much of modern life involves the addiction of work and productivity, so the lines get blurred often.

It’s still amazing compared to hours lost to commuting, pointless meetings, and staring at the beige interior of a cubicle (imo), but long-time freelancers will tell you it comes with its own set of very real obstacles.


Our Community’s Top Work From Home Tips for Freelance Writers


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You love connecting with other freelancers.


When remote working gets tough or you just feel burnt out, you learn to reach out for support.

Freelancers have more resources than ever when it comes to community, since the freelance workforce is always growing.

Because freelancers, new and experienced, all face similar obstacles, there is an amazing opportunity for mentorship, communal growth, and bonds to form.

Sometimes that means meeting up with other freelancers in your neighborhood or chatting with them online.ย Sometimes it means hanging out with them in a Facebook group and discussing different challenges you’re facing.

(I can’t stress enough how awesome the Freelance Writing Cafe Facebook group is for this—I’d be lost without it!)

Freelancing is so dynamic in nature that those event moderately experienced can bring a huge variety of solutions and perspectives to the table.

Our unique career paths make it easy to bond, learn about new apps or strategies together, and even just gripe together on occasion.

It feels good to know you’re not in this alone and that there are others who understand.


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You’re responsible for your own success.


Please read that again.

You and you alone are responsible for your success as a freelancer.

It takes some time for that to sink in, but once it does, the woe-is-me conversations you see in freelancing forums online begin to feel …don’t hate me for saying this, but… lazy!

Freelancers are responsible for the rate of their acceleration, the skills they bring to the table, how effectively they communicate, and more.

The good, the bad, the blah… it’s all on you.

Understanding what this means can be the difference between you making it and going back to a 9-5 job, tail between your legs.

Being your own boss is really hard, friends.

Even if you’re a type-A personality who has it all together, learning to have complete accountability, discipline, and motivation without external pressure of any kind is not an easy thing to learn.

No one tells you when to show up, how much effort to put in, or how to do basic things that corporate offices have entire departments for (invoicing, conflict resolution, legal, etc).

You have to put in the work, both to master your own behavior and run a business (maybe for the first time).

Obviously it’s possible! You have limitless potential and the ability to make any outcome happen for yourself. You have the ability to master it all.

But it’s no piece of cake.


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You learn and adapt with impressive speed.


Because there’s so much to learn, you’ll learn an incredible amount as a freelancer in a short time.ย In fact, you’ll probably shock yourself in the beginning.

But with each new skill you learn, each new failure and lesson absorbed, each new strategy you test?ย You’ll build up more confidence.ย You’ll increase your value. You’ll go from newbie to pro.

You’ll find that the challenges are many, but you’re up to them. You’re a problem solver, after all!

We learn a lot faster by doing things, and in freelancing, you have to take action to generate income. It’s all about doing. That means you’ll be racking up knowledge at a rapid speed.

It won’t take you long to learn to set up a website, to write great emails, or to create policies that protect your time and energy.

It won’t take long to learn how you can differentiate yourself within your niche, to schedule your obligations in advance, or leverage apps to work more effectively.

It won’t take long to figure out what your clients want (they’ll tell you the first time when they don’t like something).

You get the idea.

You’ll constantly be tweaking, improving, evolving. It never ends. And that’s a good thing, because you keep growing, both as a person and as a professional.

The learning curve is rapid and sharp. It’s exhilarating and exhausting. But if you dig your nails in and go for the ride, it makes you an incredibly valuable person to work with.


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You’re always changing—and so is your industry.ย 


My freelance process from 2009, when I first got started, looks nothing like it does today. It would be kind of boring if it did!

My website has changed a hundred times. My bio? Ha! I rewrite that almost monthly (always cringing at the last one).

My onboarding process has changed. My rates and policies have changed many times as I’ve learned what works best for me—and how I can best serve my clients.

Those clients expect different things than they did when I was getting started. Their expectations are always evolving.

I take on more demanding work and turn out higher quality results than I did in the beginning.ย The essential services I offer are similar, but even they’ve evolved with the times.

While competition isn’t a bad thing, there’s certainty more of it now. There are more freelancers than ever before, and that number is always growing.

Because of this, my mindset had to change (scarcity doesn’t serve you).

The point?ย While it’s possible to spend a long time employed in one company and see things slowly shift over time, freelance life can change fast.

You’ll gain and lose clients.

Algorithms and best practices change.

Your industry will change with new products and launches, shifts in the business landscape, key players and disruptors.

New systems and processes pop up that you have to learn—or opt out of. You’ll always be sorting through new information and resources, making quick decisions about what’s relevant and what’s not.

As I mentioned above, learning will become a huge theme. Learning new skills and up-leveling your value will be a big part of your focus.

If it sounds overwhelming, it can be! But you’ll get used to being in flux. It’ll become second nature to adapt and flow.

You’ll learn how to make decisions that benefit your business, apart from the emotion and overwhelm. You’ll learn to balance your numbers with your emotions and expectations, and call the shots.

And when you fail, you’ll get back up and try again.

That’s just the nature of the game.


I hope that this post gave you a deeper look into some of the challenges and benefits of being a freelancer for the long term.

This post may not reflect everyone’s experience, but after a decade in my industry, it reflects mine.

Because freelancing is a unique experience for each of us, you may find some of these “truths” become real for you much earlier than you thought they would. Or you may be a veteran freelancer who disagrees!

That’s totally fine. Either way, I feel like the first step to demystifying the freelance experience is to share our own individual points of view.

If you have something to add, drop a comment below or come chat with us in the Freelance Writing Cafe Facebook group. I’ll see you over there!




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