When I worked a typical, corporate 9-5 job, I dreamed of the day I could freelance. I so badly wanted to be my own boss and feel a sense of autonomy and ownership around something I had built from the ground up.
Now that I’m living the freelance life, while I don’t take a second of it for granted, like any job, it’s not perfect. Besides the constant struggle of figuring things out on my own — like the daunting task of taxes, which are much more complex as a freelancer — there’s also the constant mental gymnastics of what time off work really looks like.
And it’s not just vacations or sick days — the idea of family planning is something that’s constantly swimming around in my mind.
I don’t know what family planning looks like for us
This kind of planning is certainly not the kind of advice that shows up in articles about how to be a freelancer, or the 500-word LinkedIn think-pieces about the freedom of self-employment. It does, however, show up for me at 1 am when I’m lying awake, wondering about what the future holds.
Personally, of course, but also professionally.
My husband and I are both at the point in our careers where taking extended time off isn’t something either of us wants for ourselves. He’s a medical resident, so his schedule is its own beast, and certainly not his own. He gets two weeks of parental leave until the pager goes back on and doesn’t stop. And I get exactly as much parental leave as I negotiate with myself. Which, in a perfect world, is as much as I’d need, but in reality, is probably closer to not much at all.
There are a lot of perks to freelancing, but it’s hard to plan for our future
The freelance world offers so much that traditional employment doesn’t: flexibility, autonomy, the ability to work in my pajamas from the couch without anyone judging me. So when I’m up at night stressed about the future, I feel a sense of guilt. I shouldn’t have anything to complain about. I work from home, I can choose my own hours, and the list of perks goes on.
But there’s also no HR department to walk me through a leave policy, there’s no short-term disability coverage that kicks in, and there’s no one to absorb my workload while in the newborn fog.
Not having family nearby complicates things even more
What makes planning for a family even more difficult is that we don’t have any relatives in the same town. There are no grandparents 20 minutes away. No sister who can pop over. The village that everyone says it takes is something we have to build ourselves.
I find myself wondering how other freelancers navigate this. Do they save money aggressively for a year first? Take on more retainer clients to create a steadier income? Just take the leap and figure it out after? None of these options is wrong, none is easier than the others, and I don’t know which is right for my family.
What I’ve come to sit with is something I’ve heard over and over again when it comes to starting a family: there’s no perfect time, and there’s no perfect plan.
As a freelancer without a safety net of parental leave or family proximity, I can only control what I can control, which is being more intentional about clients, savings, community-building, and having honest conversations with myself and my husband about what we can actually sustain.
The freedom of freelancing is real. I do love it. But the complexity is also real. Somewhere in the middle of those two truths, a lot of us are just figuring it out as we go.
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