The pros and cons of freelancing while starting a family

The pros and cons of freelancing while starting a family

When I resigned from my stable agency job back in 2019 to give freelancing a crack, I was oblivious to the fact that I was already 5 weeks pregnant. 

Renegging my resignation would’ve been way too embarrassing, so I decided to hell with it – I’ll just freelance AND have a baby. How hard can it be anyway?

Oh Steph, you naive little sweetheart.

Full disclosure: it has been hard.

But even fuller disclosure: I honestly think it would’ve been HARDER to have had a job while having my babies. 

There are pros and cons to both freelancing and PAYG jobs of COURSE. And how you’ll manage with kids and work will obviously come down to your individual circumstances, preferences and personality.

But for anyone considering doing the old freelancing + babies gig, I thought I’d write a bit about my experience to help you weigh up if it’s for you or not! 

Freelancing during your babymaking years: The good bits

Answering to NO ONE

Except the children, of course.

Not having a boss at this stage of life has been sublime. I owe nobody anything! I’ve been completely free to give my family my all, and I’m so grateful for that.

By contrast, I’ve seen friends and colleagues get decimated by the guilt and torture of navigating returning to work after mat leave, extended periods of sickness because DAYCARE, and feeling torn between big stuff happening with their kids and big stuff happening at work. I am relieved I haven’t had to work overtime to ‘make up’ for leave I’ve needed to look after my kids. I haven’t had to incessantly apologise or work overtime to prove that I can still do my job.

I’ve found that my clients have all been so understanding and accommodating when I've had to shift deadlines, or I’ve made silly mistakes. Maybe I’ve just been lucky! Maybe I’ve delivered enough quality work for them to completely trust me. Or maybe the freelance life just slaps.

The flexibility (hell yes!)

And I don’t even just mean in terms of time.

Yes, it has been epic being able to work the days and hours I want. (Just during a nap today? Cool. Only from 8pm–10pm today? Great. On a Saturday? Yasssss. No worries) 

Also, the flexibility of income.

As a freelancer, I can hustle when I want to, to make MORE money. Or scale it back when things are chill in the bank account department. (This is never, but hey the option is always there.)

When you’re an employee it’s near impossible to make extra cash when you need it, but when necessary I’ve been able to take on extra work, increase my rates, or charge through the roof for projects I don’t really want to do (to make it worthwhile). Very cool.

I’d also mention the flexibility of being able to work FROM anywhere (cafes, coworking spaces, my garage usually), but this applies to lots of jobs these days anyway.

No missing out

I LOVE not having that deep, sharp pang of guilt when I have to pass on attending the kinder concert, or conversely take yet another day of unpaid leave to spoil my kid on their birthday just coz I wanna. 

I can do the things I want, without having to ask. 

I can put my kids first without having to justify it to anyone. Without having to negotiate leave just to BE WITH MY ACTUAL CHILD. Bliss.

The self care

As a freelance writer I can (and do) look after myself.

I have to be hyperaware that I am my greatest (and virtually only) asset in my business. When I’m feeling flat, rundown, overtired, unwell or depressed I can’t do great work. So I am forced to take lunchtime walks, schedule personal appointments during the day when the kids are at daycare, eat healthy foods, and have a cheeky nap when I really need it.

And you know what? Mums need these things too. Desperately. But when you’ve got a boss interrogating your timesheet you feel less inclined to actually do the things you need to do to be your best self (and your best work self, AND your best mum self too).

Freelancing during your babymaking years: The tough bits

The insecurity, the lack of security, and the combo of both

Insecurity in myself and my professional abilities has intensified since I’ve had kids. Especially since the second one. I have had serious moments of wondering if I’m any good at my work at all. Especially when I’ve been outrageously sleep deprived, and can barely string a sentence together.

The amount of times I’ve STARED at a quote wondering if I can possibly get away with charging that because I just don’t feel like I’m worth it.

The way I’ve agonised over whether I just need to get an ‘easy job’ during this time so my poor brain can remain mush and I don’t have to force it to think up clever things.

And it’s not just on the work front. I’ve been majorly insecure in my personal life too. 

When I’m not earning much due to kid stuff taking priority I beat myself up, my deeply entrenched Capitalist beliefs compounding the sense that I’m not worthy if I’m not earning money. Even when I’m doing vital unpaid labour, and I know this.

And this is tied into the lack of security you have as a freelancer, because you can’t get past the fact that work is fleeting, and fickle, and variable. Some months I am KILLING it and flush with cash! Others leave me panic-scrolling on SEEK because I believe I will never earn another dime as a freelancer again because there’s just no work in sight.

Hella stressful.

I am insecure in my skills and my worth, and I have no actual job security to back me up and bring home the bacon anyway. So I am left having to motivate myself to keep going even when I feel like I’m a piece of garbage. TRICKY.

The default parenting

At first, this took me by surprise. I was like WHAAAAAT?! WHY MEEEEE?!?!?

But I’ve obviously come to terms with it. It just makes the most sense for us.

My husband has a full-time job. I am choosing to do freelance work. Because of all the pros I mentioned (flexibility, no boss to answer to etc etc) I am the parent that CAN take extra time off when needed. And I should.

The frustrating side of this is that I need time to work to bring in work, do work, and make money. But when I am always being called upon to look after kids (which is often if not always), I can’t make money, do work or bring in more work. It leaves me earning less than my husband, and it makes me feel crap about myself.


I will just note here that my husband is an absolute babe AND a beautiful, progressive man. 

Our landing on me being the ‘default parent’ (i.e. the one who drops work at all cost to look after the kids when they need it) was not done through assumption that I just will because I’m the woman. We’re equals, and our importance and worth is truly not measured by how much money we earn in this house. Thought I should mention this! Not everyone has the same dynamic between partners. I would never agree to be the default parent unless I knew I was completely safe and secure in my finances and relationship.


I’ve had to put a lot of work into reframing this conundrum for myself. 

I accept now that during this phase of life I am the one that needs to down tools and put the kids first. My husband CAN take time off to look after the kids, and he often does, but I need to do it MORE. Why? Because it’s easier for me to. That’s pretty much all. 

We don’t really know if I could earn more money if I wasn’t the default parent and could spend more time working, but it’s not even about who earns more, it’s just what makes sense for us. It’s just what we do.

And yes, sometimes I HATE those days when I had a nice day of work lined up (and some hot coffees) and it all gets ruined when a kid or two wake(s) up with a runny nose. I HATE IT!!! I hate the plan being derailed. And it happens sooooo often. I hate the dreaded call from daycare to come and pick someone up. It sucks. It sucks that it’s always me. 

But it’s okay. 

I may not be earning money that day, but I get the privilege of looking after my child. You know, that cool little person I know and cherish and made myself. Often those days end up snuggly and sweet anyway.

Motivating yourself (it’s hard)

As a freelancer, there’s no manager or colleague in sight to use as a sounding board. But I can, and do, lean into my virtual coworking community and other supports. (A friend has taught me to use ChatGPT as a sounding board in my work and general perplexity, and that’s been cool!)

Freelancing can be lonely. It’s all me!

There’s no end of year Christmas party or bonus, but I sort of make something up in my head in lieu of it (e.g. transfer an extra $1k over for Christmas shopping; pay for a fancy lunch with the business card and that’s my Christmas party).

There’s no WIP meeting or retros, but I develop my own systems of checking in with myself, planning and learning.

There’s no PD budget, but I take myself to conferences and do webinars and spend way too much time on LinkedIn trying to get inspired.

There’s no feedback on how I’m doing!!! (I’m a high validation needs girlie). But I have my income, feedback from my clients, and how I feel inside my soul to go off.

Motivation to keep going isn’t handed out freely when you’re a freelancer. You have to hustle hard to feel good about yourself and keep going. 7 years in, I think I’m somehow managing to do this okay.

No bonus financial perks

And what I mean by that is, I never got any paid parental leave beyond what the Australian Government generously offers to all eligible workers (18 weeks’ minimum wage in my time). 

I don’t get offered pay rises (except for the ones I make up for myself), and I don’t get promotions. I don’t get a company car. I don’t get a company computer. I don’t get access to company software subscriptions or memberships or discounts.

It’s just me, my invoices, and how I choose to allocate the money my business makes.

Okay fine, and a bunch of entirely legitimate tax deductions too, because obviously.

In summary

I have had two kids while freelancing. My second is currently only 20 months old, so he's still quite little and needy. I do seem to remember I found this beautiful sweet spot after having my first child where we’d passed the getting-sick-all-the-time phase and I could work lots. I felt great and was earning more than ever!

It has been a lot more challenging with two, because they alternate getting sick and needing time off so I am with kids and unable to work a lot more often. Also, the second kid is CRAZY and has never slept well and has turned me into a shell of a woman HA!

Now as well we’re about to enter our SCHOOL YEARS which will be a whole other thing because we’ll be inundated with short days and school holidays. At the same time, the kids will be able to entertain themselves a bit better when they’re school aged.

So are we past the hardest bit? I’ll let you know how we go. 

Am I open to getting a PAYG job again some day? Heck yes. I actually hope I have one again some day! But for right now, freelancing is a preeeetty sweet way of making money while spending as much time as I can with my littlies.

And in case you’re wondering, no, we could never afford to live off one wage. Name a millennial who could. I'll wait…

Case Study Time: Writing About Type 1 Diabetes for Stripped Supply

Case Study Time: Writing About Type 1 Diabetes for Stripped Supply