What I Wish I Knew When I First Started Copywriting: Lessons After 2 Years of Being a Copywriter

It’s official: It’s been 2 whole years since I became a copywriter and decided to pursue this creative entrepreneurial path. 

In the last two weeks, I’ve had dozens of eye-opening conversations with old friends who are pursuing their own creative journey and want to know how I started. I’ve also met new friends who are ahead of the curve and who are happy to share their wisdom with me. 

Every conversation made me reflect on how far I’ve come, how much I still have to learn, and what I wish I knew when I first started out. 

They say hindsight is 20/20 so in true Ash-style, I’m going to do what I do best: write a letter to my past self sharing what I wish I knew two years ago. 

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Hey you, 

It’s 2018. An email has just dropped in your inbox from someone who wants to pay you cold, hard dollars for your words. Someone who wants to call you their ‘Copywriter’. You have to Google the word because you have no idea what it is. But after you do, you feel a giddy mix of euphoria, elation, and fear. This is it. This is the golden opportunity you’ve been asking for. You couldn’t have picked a more perfect career.

Pause. 

And breathe. 

Yes, being able to call yourself a “paid writer” is utterly surreal. But let’s pump the brakes on our tendency to over-romanticise things. Let’s resist the urge to crush this new role under the weight of our expectations. Because here’s the hard truth: nothing is ever “perfect”.

You know how people say too much of a good thing can be a bad thing? The same can be said about writing. Don’t believe me? Let’s use chocolate cake as an example, our favourite treat. 

When you take the first bite of the chocolate frosted cake, it’s divine. Your eyes roll back in your head. Your tastebuds explode with joy. You can’t stop moaning “oh my god” in-between mouthfuls of frosting and you wonder if it’s possible to be in a monogamous relationship with cake. Once the first slice is demolished, you declare you could happily eat the whole dang cake. 

Oh, look. The Universe has heard you. Someone puts another slice in front of you and you devour it with joy. Then, another slice appears. And another. Hey, you did say you could eat the whole thing, right? Time to make good on your word. 

By the fifth slice, you start to feel ill. Your jeans are unbuttoned and you’re about 4 months pregnant with your food baby. The already-devoured slices feel like a rock in your stomach. It physically hurts to eat another bite. You wonder what sadistic person would willingly put themselves through this torture. 

That’s what writing for a living feels like, sometimes. Now it’s your ‘job,’ you have to create on command. You don’t have the luxury to sit and wait for inspiration to strike. You have to write come rain or shine. The only inspiration is the looming deadline and fear of disappointing your client. Before, when you could only steal slivers of opportunities to write, your creativity was bursting at the seams. Now you’re relying on it to make you money, your muse has packed its bags and fled, leaving you to pay the bills. 

You can’t start off as a copywriter expecting a smooth ride the whole way. Like everything in life, the creative journey will come with its fair share of highs and lows. There’ll be days when you have to pinch yourself because you can’t believe you get paid to write and scroll on Instagram. But there’ll be times when clients nitpick endlessly at your work, people ask if you’re financially stable when you tell them what you do, and you’ll wonder if you’ll ever be good enough. 

When this inevitably happens, remember the big picture. Recognise it’s a privilege to create. Learn to find the joy in your creative process, irrespective of what other people think. Carve out time to create for yourself. Don’t be in such a hurry to monetise every part of your art or to publish it online for the thrill of likes and comments. Some things are meant to be kept sacred. When the days are long and the words don’t want to come out, remember why you started: to serve people with your words and feelings. 

Now, for the practical lessons; the nitty-gritty steps you’ll want to skip over but are crucial for you to survive. 

Boundaries are non-negotiable. Repeat this back to me: Boundaries are non-negotiable. They’re not something to be changed and shifted when a client demands it just this once. You’ll learn this the hard way because you’re a people-pleaser. You’ll re-schedule dates with Ben, holidays with your family, and precious time with yourself to cater to the whim and fancy of clients. You’ll be with people you love but you won’t ever be present because you’re always responding to emails and text messages. Even when you’re “resting,” you’ll stress over whether you’re going to miss a phone call or an urgent email. 

This is a recipe for burnout and resentment.

One night, you’ll be crying on the phone with someone and wondering why you’re so exhausted all the damn time. They won’t have the answers for you, but they’ll tell you, “life’s too short for a job to make you feel this way.”

You’ll remember why you chose to be self-employed instead of becoming an employee — because you wanted a life of freedom. A life where you didn’t have to worry about whether you were going to get a client’s “urgent” request at 5 am in the morning. How do you get freedom? Boundaries. Set your working hours and stick to them. 

It’s not enough to tell people what your boundaries are. You have to practice it too. We teach people how we want to be treated. If you tell someone you can’t be contacted before 9 am, then don’t pick up the phone when they inevitably call you before 9 am. If you do, you’re implicitly teaching them it’s ok to violate your boundaries because you won’t ever enforce them. Keep your word to yourself. 

Know your value. Because writing comes naturally to you, you believe everyone is good at writing. You’ll soon realise some people can’t spell, even with auto-correct. Some people believe writing well means using a thesaurus on every word. Some people can write, but hate it with a passion. That’s why the role of copywriter exists. 

Not everyone will understand the value of what you bring to the table. They’ll think it’s “just a blog post” or “just a tagline” and they’ll expect you to whip it up in 10 minutes flat like you’re a microwave. When this happens, you need to fight for your craft. Advocate fiercely for your process. If you can’t see the value in what you bring to the table, no one else will. Words matter and your ability to string the right ones together can be the difference between a client making bank or pulling their hair out because they have zero sales. 

Get a contract. Get a contract. Get a contract. As a former law student, it’s embarrassing you don’t already know this. Right now, you believe the best in people. But sometimes, shi*t happens. People will run out of money and need to cancel projects. They’ll ‘forget’ to pay you even after the fifth reminder. Some will even turn on you and try to coerce you into signing your rights away. You’ll learn there aren’t enough laws or rights to protect freelancers, so it’s up to you to protect yourself. 

Invest in mentors. Always be hungry to learn. Right now, you’re practically a foetus. You know nothing about copy decks, creative briefs, or SEO. Fight uncertainty with knowledge. There are thousands upon thousands of people offering up their knowledge for free or for a price less than your Sunday morning brunch. Invest money in online courses, listen to all the podcasts, and learn from those who have gone before you. People are always willing to help so long as you respect their time and their expertise. And please don’t ever use the phrase “pick your brain” when you approach them. People will do this to you one day and the phrase will make your skin crawl. 

Trust your gut. Your body is an amazing bullshit detector. Even if you can’t pinpoint exactly what’s wrong, your body will tell you. When people ask you to compromise your integrity to help them achieve success, your gut will flare-up. Listen to those signs. Learn to spot the red flags early, then get out. Avoid the temptation to paint the red flags green just because someone is willing to pay you. Sure, you may get to send a big, fat invoice at the end of it. But no amount of money in the world will heal the emotional scars or give you your time back. 

Stop comparing yourself. It’s ok to look to others for inspiration or as a guide to where you want to go. The danger is when you look to others to fuel your feelings of inadequacy. Don’t look at someone five years ahead of you and beat yourself up because you’re not “there” yet. That person spent the last five years collecting failures, honing their craft, and learning from others. Keep your eyes on your own lane. While you’re wishing you could be as good as them, someone else is wishing they could be as brilliant as you. 

I’m not going to sugarcoat it, love. In the next two years, you’ll be filled with self-doubt, fear, and uncertainty. You’ll think everything you write is trash. You’ll keep waiting to feel “legitimate” and you’ll wonder if you’re ever going to “make it”.

But one day, you’ll get to see your words on the website of a national brand. Strangers from the internet will email you to say your stories have been a lifeline in their toughest moments. Clients will find their way to you instead of you hustling your way to them. The first time you try to make a sale, you’ll fail and somehow manage to turn it into a funny story. But the next time you pitch yourself, you’ll close the deal and celebrate by spending half of the invoice on cake and wine. These are the moments that make the whole journey worth it, so hold out for them. I promise they’re coming.

These next two years are going to fly by. Remember to enjoy the journey. Keep track of every single win, no matter how small, and savour every victory. When clients are difficult, give them more grace than you get. But don’t allow yourself to be walked all over. Most importantly, give yourself more grace; you’re doing the best you can. 

Encouraging you now and always,

Ash 

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