I’ll never forget September 9, 2019. That’s the day when I saw two pink lines on a pregnancy test.

I showed the positive test to my shocked husband, and we then promptly went out for burgers to celebrate and ran to our nearest Barnes and Noble to purchase What to Expect When You’re Expecting.

We were absolutely thrilled to know that we were expanding our family, but I’ll be honest: It didn’t take long for the reality to sink in. One of the biggest concerns that loomed in the back of my mind was exactly how I’d handle planning my freelance parental leave.

As a freelancer, I knew I didn’t have any sort of paid maternity leave readily available to me. And, considering I’ve only ever taken a few days off from my business at a time (and admittedly compulsively checked email even when I was supposed to be on “vacation”), the idea of giving myself an extended break seemed daunting.

Would my clients understand? Should I work ahead or subcontract work out? Would my clients replace me while I was away? Would there be any work waiting for me when I returned? Should I just skip leave entirely and work right through for the security of my business?

Yep, they were all questions that kept me up at night. But, considering that this little human was on the way regardless, I decided to tackle them the only way I knew how: with a whole lot of lists.

I’m pleased to report that (so far) it’s all panned out. My husband and I welcomed our son, Adrian Thomas Boogaard, to the world on April 18, 2020. As I write this, I’ve been on my maternity leave for a little over three weeks, and I feel really good about all of the steps I took to prepare for some real time off.

But, since I know firsthand just how stressful it is to plan for parental leave (or really, any type of extended break) when you’re self-employed, I figured there’s never been a better time to provide some insight into the steps I took to make my own leave a reality.

Here’s some of my best, hard-won advice—because producing a tiny human is stressful enough without worrying about your career on top of it.

But first…recognize there’s only so much you can plan for

I’m a Type-A planner to my core, which means I strategized my maternity leave in true Leslie Knope fashion. There were numerous lists. Highlighters. Schedules. You name it, and I probably had it in my arsenal.

Parental leave is a huge deal, and I think it’s smart to plan for it as best as you can. However, there’s one important lesson that this experience has taught me: You can’t plan for everything.

Need some examples? Okay then. Our baby arrived an entire month earlier than he was supposed to. Oh, and he did so in the middle of a major global pandemic.

That means my delivery and even my maternity leave so far have looked a lot different than I intended. My husband is still home with me (but, he’s working full-time from our home office). I can’t have my parents or other loved ones over to watch the baby or provide support.

We’re still doing just fine. But, I think it’s important to start with this point. Babies (and the world, obviously) are unpredictable, and even when you think you’ve accounted and planned for every possible circumstance, I guarantee something will still surprise you. Don’t panic! It’s all part of the fun.

My process: How I planned for my freelance parental leave

As crazy as it sounds, coordinating my time off stressed me out more than the prospect of actually delivering the baby. Considering I’ve never had a baby before, it felt like I was trying to plan something that was full of unknowns.

I didn’t know when the baby would arrive. I didn’t know how delivery would go or how much recovery time I would need. I didn’t know how I’d feel (both mentally and physically) afterward.

I felt like I was operating with zero information, which made maternity leave feel daunting.

Believe me, I allowed myself the occasional freak-out session—but I tried my best not to dwell on those worries. Instead, I focused on what I could control: compulsively organizing and communicating with my clients about my intended plans.

Did everything work out perfectly? Not quite. As I mentioned, our son arrived an entire month early plus there was the whole worldwide pandemic thing going on. However, I do think that I had a solid foundation in place that made it way easier to deal with those unforeseen circumstances and transition into my leave without breaking a sweat.

Enough rambling. Let’s dig into the details of exactly how I made it happen.

1. I shared the news with my clients (before social media)

When my husband and I were finally ready to share our happy news with other people, of course we prioritized our close family members and friends. But, my clients weren’t too far down on the list of people to tell.

It was important to me that I told my clients about my pregnancy before announcing anything on social media. I didn’t want to leave room for them to make assumptions about how I’d handle leave or whether or not I’d return to my work. I thought I should communicate proactively about those things.

So, I sent each of my clients an “announcement” email that accomplished a few things:

• Shared our exciting news and a rough idea of when I was due
  
• Communicated that I still intended to work after the baby’s arrival and my maternity leave
  
• Explained that I’d be in touch as the due date got closer to coordinate the details of my leave

I sent these emails on November 5, 2019, when I was a little over 12 weeks pregnant. Yes, it felt a little awkward (especially since I haven’t met the vast majority of my clients in person). But, I figured if I worked in a traditional office setting, my colleagues would be looped in on the news that early. I wanted to extend that same professional courtesy to my clients.

I personalized the emails for each point of contact, but here’s a peek at what that initial announcement looked like:

SUBJECT: Some (exciting) personal news!

Hey [Name],

Hope you’re having a great week!

Sharing this sort of news is always kind of awkward—and that’s especially true in a remote and freelance environment. But, I figure if we worked side-by-side in the same office, this is the sort of thing that would come up naturally. So, I didn’t want to skip out on sharing with you.

I’m so excited to let you know that my husband and I are expecting our first baby in the middle of May!

As a freelancer without any sort of maternity leave, I don’t intend to unplug from my work for an extended period of time. However, I will be taking a short break to welcome this nugget into the world.

I’m told that babies (and deliveries!) are notoriously difficult to plan for. So, rest assured that I’ll definitely be in touch as that time gets closer to coordinate any necessary timelines, workload, etc. I fully intend to continue working after the baby arrives, and would love to keep collaborating with you on a regular basis (provided that feeling is mutual, of course!). 

But, for now, I just wanted to loop you in on the happy news with an advanced heads up. Please don’t hesitate to let me know if you have any questions!

Thanks,

Kat 🙂

I’m not too proud to confess that I was super nervous when I sent those emails. I think that’s normal. But, I was thrilled when the response from my clients was overwhelmingly positive. Every single one of them responded with congratulatory messages and reassurance that they were more than willing to be flexible with me.

2. I mapped out my ideal timeline

One of the things I wrestled with most was how much time I’d need to take off. At first, I was overly optimistic (and perhaps a little naive) and assumed I’d only need about two weeks before I’d be ready to buckle down in front of my computer screen. I laugh at that idea now.

After hearing from several people that I was living in a dream world if I thought two weeks was enough to recover and adjust to motherhood, I decided to source some insight and opinions from other self-employed people who had been through a parental leave already. So, I turned to Twitter to ask for advice.

I learned that everbody approached this differently. Some took a few weeks off, while others took half a year off. Despite the fact that there wasn’t a clear answer hidden in those replies, it did make me realize that I’d likely want to take more than just a handful of weeks.

I finally landed on taking two whole months off from client work: all of May and all of June.

My original due date was May 16 (again, Mr. Baby threw a wrench in things by arriving on April 18 instead), and I thought that clearing all of May and all of June would give me enough wiggle room and adjustment time—regardless if the baby arrived a little early or a little late. Sigh. The best-laid plans, right?

3. I strategized how to handle each of my clients individually

Through my crowdsourcing efforts, I also learned that there are tons of different ways people handle their actual workload when they take leave.

Some just take the time off entirely and let their clients fend for themselves. Some send their work to subcontractors or recommend other freelancers who can fill in for them. Others work on assignments ahead of time.

I know plenty of freelancers have done the subcontractor thing really successfully. But, that idea made me nervous. In the nearly six years I’ve been in business, I’ve never subcontracted out any of my client work. Plus, I have really strong relationships with my clients and, as egocentric as it sounds, they pay to work with me specifically. So, that option was off the table for me.

Next, I recognized that each of my client relationships was unique and there might not be a blanket approach that worked for each of them. I split my clients into two groups:

• Those I worked with on a regular, somewhat predictable schedule (about 75% of my client base)
  
• Those who sent me sporadic, unpredictable assignments (about 25% of my client base)

It was easy to decide what to do with the 25% of the clients I worked with sporadically—I was just going to be unavailable to them during May and June.

I had already shared my pregnancy news with them, and since our collaborations were random, I didn’t trouble myself with coordinating details of a formal leave with them. If they emailed me when I was out, they’d get my out-of-office message about my maternity leave, and I could reconnect with them when I returned. I was comfortable with this, especially considering it was a small slice of my client base.

For the larger chunk of my clients who work with me frequently and regularly, I thought a lot about the best way to handle their work. I narrowed it down to the following options:

• We could pause working together for May and June, and hopefully pick back up when I returned at the end of June
  
• We could coordinate assignments early, so I could work ahead and cover my own time off

How did I decide which clients got what option? Well, let’s dig into that in the next section…

4. I involved my clients in the decision-making process

Could I have gone through and just decided which option I’d offer for each of my remaining clients? Absolutely.

But instead, I wanted to involve them in choosing which option worked best for them. I recognize that my leave was significantly impacting my clients as well, and I didn’t want them to feel like bystanders—I thought this should be a collaborative planning process.

So, first things first, I got some details in order. Mainly, I wanted to get a timeline mapped out so they’d have some firm dates for the “work ahead” option. I knew that those deadlines would be make-or-break for some of my clients, so I wanted to ensure they had that information in their hands when choosing the best option for them.

Considering I intended to take all of May and June off, I landed on the following schedule for early assignments:

• Friday, March 20: Deadline for receiving early assignments from my clients
  
• Friday, May 1: Deadline for sending finished early assignments back to my clients

With that information figured out, in the middle of February (about a month before advanced articles would need to be assigned) I sent them an email that looked like this:

SUBJECT: Advanced Planning for My Maternity Leave

Hey [NAME],

I hope you’re doing great!

I wanted to pop back into your inbox in the hopes that we can get some more firm plans in place for my upcoming “maternity leave” (as someone who’s self-employed, I feel strange even calling it that).

As a reminder, my official due date is May 16. But, I’m told that babies have a knack for setting their own schedules. So, we’ll see when this little dude (yep, he’s a boy, by the way!) actually ends up making his appearance.

With all of that in mind, I’m planning to take May and June off to welcome him to the world and get adjusted to the daunting role of motherhood. As far as how to handle that brief pause, I want to involve you in that decision-making process. I’ve outlined two different options below for you:

Option A: I’ll take May and June off from writing for [CLIENT] entirely, with the hopes that I could pick back up with our relationship and content efforts on Monday, June 29 (provided you have a need for that, of course).

Option B: If you have topics or an editorial calendar ironed out ahead of time, I’m more than happy to work ahead for the months of May and June. Currently, I’m producing around [NUMBER] posts for [CLIENT] each month. That means, if you wanted to go with this option, I would need [NUMBER] posts to work ahead on (counting for May and June). In order to squeeze these in (without making myself crazy), I would need the topics decided and in my inbox no later than Friday, March 20. I’d then review those and touch base with my planned deadline for each—with an aim of having all content submitted by Friday, May 1.

A couple of other important notes about my leave:

• Of course, if I hit any unexpected setbacks or snags (or decide to return to work early!), I will be sure to keep you informed of that so you can adjust accordingly.
  
• I can never tear myself away from email entirely, and I’ll still have a close eye on my inbox even during my leave. If something comes up, please don’t hesitate to reach out to me. I’d be more than happy to hear from you (because something tells me I’ll welcome the opportunity to use my grown-up voice and vocabulary). 
  

What I need from you: Could you reply to this email and let me know which option works better on your end? 

Regardless of which route you choose, I’m really hopeful that we can continue to collaborate regularly when I’m back into the normal groove on Monday, June 29. I really value our working relationship, and would love to continue writing for [CLIENT]—I just have to have this baby first! 🙂

Thank so much,

Kat 

The one thing I didn’t count on was that nearly all (umm…all but one) of my clients took me up on the “work ahead” option.

This meant that the months leading up to my leave were a bit more jam-packed than I had intended. But, in all honesty, I’m grateful. Front-loading that much work meant those last few months were high-earning, which removed a lot of financial pressure from taking an extended leave.

5. I looped my clients in on his arrival

It was never my intention to get to the first day of my maternity leave and then sign off and ride into the sunset without saying a word.

I’ve worked with many of my clients for years, so I always knew that I’d press pause on my time off for a brief moment to let them know that our bundle of joy had made his arrival and share a photo.

What I didn’t expect was that this announcement would happen an entire month earlier than I thought it would. Yep, our little dude was born on April 18 (so much for that May 16 due date) at exactly 36 weeks.

This meant that looping my clients in on his birth wasn’t negotiable. I wasn’t supposed to be on leave for another few weeks, and I was even still finishing up assignments for some of my clients. I needed to let them know that I was out of commission earlier than intended, and we’d either have to push off those advanced assignments until after my return, or they’d have to give them to another writer.

On April 19 (the day after our little guy made his big debut), I emailed each of my clients personally from the hospital to share the happy news. For clients who still had pending assignments, I also asked them how they’d like to move forward with handling those loose ends.

Again, these emails were personalized depending on where things stood with each client, but here’s a peek at what the message looked like in its basic form:

SUBJECT: Some exciting (and unexpected) news!

Hey [NAME],

I hope you’re doing well! 

I’m stopping by with some (very) unexpected news. I’m so thrilled to share that my husband and I welcomed our son, Adrian Thomas Boogaard, into the world at 5:42AM on Saturday morning. 

[PHOTO OF PRECIOUS NEW ARRIVAL]

He definitely took us by surprise with a speedy delivery and an early arrival (he’s a month early!), but he was ready to come join the party at 5 pounds, 9 ounces and 19 inches long. So far, all of his test results have looked great.

He must’ve known how hard I worked to meticulously plan my maternity leave, and wanted to kick things off by throwing a wrench in all of those plans.

So, with that in mind, I know we still had this/these article(s) that we were trying to wrap up: 

• [TITLE OF ARTICLE]

Obviously, I’m going to be signed out for a bit, so I wanted to check in and see how you’d like to handle that/those article(s) now. I totally understand if you’d rather hand pending assignments to a different writer. 

Otherwise, if you have flexibility, we can talk about having me tackle that/those piece(s) in June…I’ll likely return from my maternity leave a little earlier than originally planned, now that he arrived a month early. 

Let me know what you think!

Either way, I just wanted to share the happy news.
Kat 🙂

Personally, I felt a little guilty that I wasn’t able to wrap up all of the advanced assignments I had committed to. But, all of my clients were super understanding about our kiddo’s early arrival.

The vast majority told me not to worry about the items left on my plate and that they’d take care of those. Others told me to let them know when I was back in the swing of things, and they’d push my remaining projects off until then.

6. I set an out-of-office message

I’ll readily admit that I’m compulsive about checking my inbox. I feel an enormous amount of self-imposed pressure to respond to messages promptly, and I’m a little neurotic about keeping all of my email folders clean and organized.

That’s why I knew going into my maternity leave that I’d need to set an out-of-office autoresponder that let everybody know I was on leave. Not only does this automated message help proactively manage expectations with the people who are emailing me, but it also gives me an incredible amount of peace of mind. I don’t feel as stressed about staying on top of my emails, because everybody is immediately looped in on the fact that I’m away for the timebeing.

With that being said, I also know myself well enough to know that I can’t make a clean break from my inbox. So, I made sure to communicate that in my out-of-office message too. I made it clear that I was still checking emails, but that my response time would likely be delayed. Again, it takes the pressure off me to reply immediately, but also reassures me that I’m not totally off the grid.

Finally, I’m a big fan of incorporating some fun and personality into automated messages. So, here’s a peek at what my own out-of-office message looks like:

SUBJECT: Oh, baby! I’m on maternity leave…

Hey there,

Thanks so much for your email! But, if that not-so-clever subject line didn’t do enough to clue you in, I’m currently out of the office.

While it was a little earlier than expected, my husband and I are thrilled to have brought our first child (a baby boy!) into the world. I’m taking some time off to squish his little cheeks and adjust to the daunting new role of “mom.”

Have no fear! I’ll be back to my desk and normal work responsibilities on Monday, June 29.

Please be aware that I am still checking in on email during this time (hey, I can’t tear myself away from the “real world” entirely!), so your message won’t be floating in cyberspace until the end of June.

However, with a new little one at home, my response times will inevitably be a bit delayed. If you need to get in touch with me ASAP, please respond to your original message with “URGENT” in the subject line.

Thanks so much for your patience during this exciting (and admittedly somewhat terrifying) time!

All the best,
Kat 🙂

Spoiler Alert: You Won’t Plan the “Perfect” Freelance Parental Leave

Figuring out how I’d handle my maternity leave was one of the major stressors I dealt with during my pregnancy (you know, aside from the whole “growing a human” thing).

Since I pride myself on my level of organization, I had high expectations that I’d plan for some totally seamless time off…

…and then the world was struck with a major pandemic and my baby arrived a month early.

That’s the thing about planning for parental leave: You’re dealing with a whole lot of unknowns.

So, ultimately, all you can do is organize as well as you can and proactively communicate with your clients (especially when the unexpected happens).

The way I went about things certainly isn’t the only way to plan your own leave. But, I hope it gives you some insight into how the process worked for me and helps you start thinking about what might work best for you. Much like babies, no two parental leaves are exactly the same. 🙂