Being your own boss: is it all it’s cracked up to be?

Behind the curtain on what it’s like to be a freelance copywriter


There’s a lot of kickbacks to being your own boss, and it doesn’t matter if you call yourself a sole trader, a freelancer, a guru, coach or entrepreneur – every small business owner will tell you that it’s bloody hard work.

The secret, I’ve found, is in learning how to shape your business to suit your life.

As a copywriter and content creator (yes, there’s a distinction but that’s a topic for another day), I decided to compare my day to day life with a few others from the Clever Copywriting School Community to hear about their experiences as business owners.



No two days are the same

The freedom to design your day is undoubtedly one of the perks of freelancing.

Of course, no two businesses are alike, but in the beginning of my freelance career, I struggled with the idea that I had to follow a cookie-cutter approach, operating in a certain way in order to be successful.

But that’s not the case at all.

Being self-employed suits Darren Baguley, because he juggles a small farm around his work. “It’s why I don’t get to my desk until 9:30am. Livestock are a little like kids in that there are times when they have to come first. If they’ve run out of water you just need to sort that out whether you’re on deadline or not.”

Claudia Bouma says she designed her copywriting business to fit around her family and prioritise time with her four kids. “My typical working day changes all the time depending on how many copywriting projects I’m working on. I love the flexibility that comes with being self-employed because I get to choose what I do, when I do it and how I do it.”

Having transitioned from full-time copywriter to author, mentor and speaker, Kate Toon has learned to go with the diversity in her work. “There’s no typical day for me,” Kate told me. “And that’s what I love best. I might be writing a new course, coaching a group of copywriters, making SEO tutorials or recording a podcast.”




In my world, being my own boss gives me the ability to choose the projects I love, so I can use my skills to make the biggest difference in my client’s businesses. It’s such a great feeling.

On a good day, I walk/run a 3km round trip to take my kids to school and get back to my desk by 9:15am with breakfast in hand. I review my Asana list and start on the most urgent tasks. I work through until school pick up time, and often a couple of hours in the evenings as well.

From the outside, having your own business can look glamorous, but there’s much more to it than flexibility and the thirty-second commute. To be successful you need to…


Define what your business does for your life

We spend most of our adult lives working, so I believe you should love what you do and by extension – what it does for your life. And being a part of an amazing community of writers has taught me that my business needs to work for me, not the other way around.

When I first set up my freelance business, it was because I wanted to prove to myself that my writing could earn me money and I could do it while being closer to my family. I gave myself a six-month deadline to start replacing my wage and I met that target, but I wasn’t prepared for how much work it would be!

Now, I work more hours than I did in my old 9-5 job. I’m getting results, but it’s a long game. I enjoy love what I do, but if you don’t love the whole gig (and you’re not prepared to stick it out) it won’t work for you.

Sydney copywriter, Angela Denley agrees. “It can be a bit of a balancing act, but I like to say I’m ‘juggling not struggling’ as I fit work around family and family around work, with the odd bit of time for me, too!”

Time for me, you say? What’s that? 



Balance is important

So, being your own boss is hard work. How do you avoid burnout? Finding time to schedule work around exercise and help out in her kid’s class, Angela built her business around her life.

She goes to the gym three mornings a week, shifting to earlier sessions if she needs to allow more time to complete client work. “I love that I can adapt week by week for whatever life throws at me. When the deadlines mount, I’ll usually get up early, around 5am, to get a jump on the day rather than working at night.”

On the other end of the spectrum is Darren Baguley. He’s a night owl and knowing this has helped him achieve success. “I tend to do my best work in the afternoon but I do ‘has to happen’ stuff first thing otherwise it may not get done.”

Maybe it’s all the caffeine that I’ve had by mid-afternoon, but like Darren, my optimum time for writing is between 1-4pm and 8-11pm. As a night owl however, I’m conscious of putting in too many hours. I’ve got a tendency to work too late and as I’ve figured out #writinghangovers are a b*tch. Writing is hard work, and you need downtime in order to do your best work.


Work out how you achieve results

In the beginning, to avoid the next day hangovers I tried to shift my sleeping pattern to get more done early in the day.

I failed. Miserably.

So, I’ve had to go with the flow and do my light, admin work before lunch, my deep thinking, and complex writing after lunch until school pick up, and again as soon as the kids are in bed. Recently, I’ve begun setting an alarm to tell me to shut down my laptop.

Sydney tech writer and digital expert, Jasmine Andrews told me it’s taken her 5 years of freelancing to design a structured work week that gives her time for client work, professional development and herself. “I used to work any time I could, squeezing in as much work as I could. But it wasn’t very efficient and I felt like i wasn’t getting enough work time or downtime, and I wasn’t profitable.”

She now has a structured week with time for work and time for herself and for her family. “I work school hours, 4 days a week. The first and last half hour of the day is spent on emails, admin, and social media. I try to spend 100% of the rest of the time on client work. Monday and Thursday I go out to client meetings and workshops and Tuesday and Friday I work from home on the projects from the previous day. Wednesday is reserved for self-care and professional development.”

Rebecca (Beck) Cofrancesco from Marketing Goodness told me a similar story.  “I used to be terrible at the beginning of this freelance, entrepreneurial life. Now I’m more structured.”

Beck now works at a co-work space on Monday’s and Wednesday’s, limiting meeting availability to those days. She works in blocks of 2 hrs on Tuesday’s and Thursday’s and Friday is her day to do what she wants to do.

Not surprisingly with over a decade under her belt as her own boss, Kate Toon knows that she can do some of her best work early in the morning. “I’m attempting 5am wake ups to smash a few hours out before the world wakes up.”

When and how you decide to work in your business is up to you, and for the most part, I’m still refining these processes. It’s easy to fall into bad habits and lose your mojo, so your success depends on how you make the partnership between your business and life work for you.



Being your own boss has side effects

It’s pretty obvious by now that freelance life is a juggle. For me, the juggle is worth it. I’m very self-motivated, and my clients love that about me. I know I can be a bit of a slave driver, so I’m trying to be kinder on myself.

But, I love my clients and my work. It gives me a sense of achievement knowing that the money in my account is because I’ve won the job and I’ve helped my client, in my way.

The effects aren’t always positive though.

“It’s always a struggle to juggle everything and self-employment comes with a big spoonful of mum guilt,” Kate Toon admitted. “But I think my son is lucky to have us at home so much. My boss can be a bit of a bitch, she pushes me hard, but occasionally rewards me with a foot massage.”

(Nice one! I think I need a massage too…)

The flexibility of not having to check-in with anyone is a big bonus if you ask Darren. “If I want to go to a field day or a workshop or something, as long as I’m up to date I go. I love the variety and not being pigeonholed, if I can come up with a pitch and get the client to pay me for it, I get to do it.”

One of the best things to come from my freelance career is the new knowledge and skills I’m constantly developing. If I want to advance my career or pivot the direction of my business I can. I’m not restricted to a predefined development pathway: If I want to explore a new aspect of digital marketing I can do so, and these skills enable me to better help my clients.

No matter the side effects, being your own boss is both rewarding and tiring. But I wouldn’t have it any other way.


Over to you

Are you an entrepreneur? Or are you thinking of switching gears to become your own boss? Is it as hard as you thought it’d be?

Tell me about your experience in the comments.