How I Prepared for Maternity Leave As An Entrepreneur

It was so fun to get your emails & messages asking me to write about how I prepared for maternity leave. This is a post that I am SO excited to write — glad to know it will be fun for you all to read, too!

The big reason that I wanted to write this post is because when I was preparing for Alyosha’s birth I felt a bit lost. I searched the archives of blogs that I frequent & wasn’t able to find a post like this (but I reallllly wanted one). I was at a bit of a loss for resources & so I just followed what felt right to me — when in doubt… it’s the best “method” around!

Let me start by saying that what is in this blog post is what worked for me. Every mama is different, every family is different, every baby is different, & we all have a unique set of financial, medical, & emotional conditions that we are operating within. So, take my experience for what it is: my personal experience.

Use what works for you, ditch what doesn’t!

This might be the longest/most detailed blog post I’ve ever written, so grab a cup of coffee & get cozy…

#1 – Before Alyosha arrived:

As soon as I found out that I was pregnant (which was very early on… at 2 weeks!) I had to start making a plan pretty quickly. Why? Because I work with women in a 6 month program, so that meant I had to enroll my clients, at the latest, 6 months before Alyosha’s due date.

I instantly counted backwards 6 months from his due date (September 3, 2016). But, because I do everything solo for my business, I also had to think through things like “what if he comes a few weeks early & I can’t finish my client sessions?” There wouldn’t be anyone there to “fill in” for me. I knew I wanted to take time off after he was born & be totally unplugged from work, but I also knew, because of the nature of the work that I do, that I didn’t want to have to text my clients & say “in labor!! Sorry to have to cancel your last session! We can reschedule in a few months!” So, I added a few weeks buffer before my due date. I did a little math & made sure that I could have my 6 month clients’ programs wrapped up 3 weeks before my due date.

While I typically operate on a rolling enrollment for my program (aka when one client wraps up, I start another one – so I usually have clients at different places in programs at any given time), I did a mass enrollment for the first time. This required me to promote my one-on-one program way more than I typically would have. So, when I was just 1 month pregnant I started by sharing on my mailing list, blog, social media, etc. I prayed about this a lot & asked God to bring me the women who he wanted me to support during this time. I always pray about my current & future clients. This brings me so much peace!

Once I enrolled these pre-maternity leave clients (the most clients I had ever had at once! & such amazing women), it was time to think about the following:

  • How much time did I want to take off after Osh was born?
  • How would I enroll clients at that time?
  • What would my work schedule & child care look like when I went back to work?
  • What other logistics needed handled?

Deciding how much time to take off —

I decided to make my official “back to work” date on October 10, which meant that if Osh came on his due date I would get 5 full weeks off. To some people this might sound like no time at all, to others it might seem like a luxury. I made this decision for two main reasons: (1) Our family depends on two incomes. The money that my business makes is necessary for us! If it was just “extra” income then I would have likely taken way more time off. But the reality of having your own business is that if you’re not working then you’re not making money. &, like I mentioned, I need to be making money. This is NOT me complaining or saying woe is me, it’s just me being honest! I want you to know my real-life considerations so you can understand how I came to the conclusions that I did. Your considerations &/or conclusions might be very different & that is great, too! With the 3 weeks before my due date + the 5 weeks after, money wouldn’t be coming in to my biz for 2 months. I felt totally comfortable with paying myself for 2 months without any new income coming in so that was a big deciding factor; & (2) I love the work that I do &, in a way, my business is one of my babies. I felt it would be really hard to be away for a ton of time. Even before I took time off I could already feel myself being “ready to go back” (remember, this was before I actually had a baby hahah! I wrote all about the conflicting emotions I actually felt going back to work in this blog post here).

Before I move on, I also want to share a fear that came up for me around taking time off for maternity leave: fear of rejection. This is one of my core fears that I have spent a lot of time working through in my own journey so that I can operate in my life from a place of love. But, at times, it still sneaks in there!! In this situation, my fear looked like this: “if I take too much time off, if I am away for too long, I will become obsolete & nobody will want to work with me anymore.” It felt really yucky & made me feel panicky. So, rather than making a decision from that panicky place I worked through this fear FULLY before I officially decided on how much time off I would take. I got calm, centered, & then was able to make a loving choice for myself. I just wanted to share because others may also have similar fears! We all have fears & it isn’t about getting rid of them completely, right? Instead, it is about learning how to identify them, work through them, & get back to a loving place. As always, just being real with you beauties.

Enrolling clients to begin after maternity leave — 

I decided that I wanted to be able to start with clients on October 10 when I got back to work, which meant that I needed to hold consultations before Osh was born. I blocked off time on my calendar during weeks 2-4 before his due date & started building up a wait list right away. So, for about 6 months, everyone who filled out my consultation form got put (chronologically) on a wait list. When it was time to hold consults, I reached out to them to set up their consultations (FYI, many of these women signed up for a consult & some never responded — this is SO NORMAL). After contacting the people on my wait list first, I also sent an email to my mailing list & shared via social media! I held consultations for a few weeks, connecting with some incredible women, & signed up clients to begin in October.

I was super clear with these clients about my maternity leave during the consultations. It was really important to me to be on the same page, set realistic expectations, & to foster trust right from our first interaction. I set up every client who signed up with Finally Free Program to work on during the time between when they signed up & when we started, too, so they could feel supported during those interim weeks if they were ready to dive into material right away! I also collected a 1 month non-refundable deposit from everyone who signed up to save their spots, which I applied directly to their program cost when we got started in October (so, they didn’t actually pay any more than they would have if we had started right away – they just paid a little differently). I did this because I had never enrolled clients 2 months before a start date before, & my friend + mentor Jamie Mendell recommended this to me! It was a great rec & worked really well.

I gave these clients access to my calendar right when they signed up, too & let these clients schedule their October sessions right away!

Work schedule/daycare —

I have always seen clients 3 days a week & used the other 2 days to do other business things (i.e. writing, accounting, collab meetings, etc). So, I knew I wanted to continue with a similar schedule once Osh arrived.

Tim & I talked & felt that it was best for our family’s personal situation to have someone come to our home part-time to be with Osh on days when I had client sessions. I work mostly from home & so this option would also allow me to breastfeed Osh when possible. I loved the idea of being able to see him sporadically on work days & to know he would be super close if I needed a little snuggle. To make this happen we worked with Kiddo & Co.

Taylor Cobb, the owner of Kiddo & Co., came highly recommended from our friends Allie & Adam of The Wonder Jam. We had met Taylor a few times at events & so reached out to her! She took care of everything (background checks, setting up interviews, contracts, etc) & found us the most incredible nanny for our family. Brigette is a dream & comes to our house Mondays – Wednesdays. If you’re in Columbus & are interested in a part or full-time nanny, I can’t recommend Kiddo & Co. enough (not sponsored, just my honest + personal experience!).

Once we had this set up, I was able to know the hours that I would see clients & open up my October calendar accordingly for clients to start scheduling their post-maternity leave sessions (as I mentioned above).

Outside of these hours, & because of the nature of my work, I decided I would be with Osh when I was not holding client hours (take him to meetings, respond to emails while wearing him, etc). Kimberly Snyder was & continues to be a huge inspiration to me in this area. I watched her post pictures of her writing with her little man & also taking him all over (business meetings, work trips, etc). This let me know it was possible if it was something I desired to make happen. Obviously I am not saying that this is the “right & only way to parent,” but it was something I desired so I sought out women who were doing it. I believe it’s so good to be reminded that what our hearts desire can be our reality & seeing Kimberly Snyder run her business in this way showed me that it was possible.

Logistics —


I set up an out of office months before I went into labor & Tim (my husband) knew that it was his job to activate it when labor started!

I also scheduled a number of emails to go out during my maternity leave for summits that I was a part of during that time + for a program I was affiliating for! If I couldn’t pre-schedule content during that time then I said “no” to opportunities that presented themselves but would have required me to work during my maternity leave. This was a personal preference, but it felt really right for me.

#2 – During maternity leave:

I put up an out of office & I really stuck to it. I didn’t respond to emails the entire 5 weeks that I was off with the exception of my private clients.

The women who signed up to work with me one-on-one knew that they could text me if they really needed pre-program support & could ask me to check my email, which I would have gladly done for them. They also knew that my response time would be wayyyyy slower than when I was back to work. I was super clear about these boundaries so that nobody felt let down or taken advantage of. Of course everyone understood. & if they didn’t, well they wouldn’t have signed up with me, right?? 😉

I stayed active on Instagram during my maternity leave, but just in a way that felt really organic! I was so excited to share Osh that it was fun! I also sent 1 email to my list introducing them to Osh. Otherwise, I didn’t do any social media or writing work! Anything else that went out during my 5 week maternity leave was pre-scheduled.

I spent these 5 weeks soaking up every second of family time & it truly was the most magical time of my life so far. I’m looking forward to sharing more about this, but sweet mother of pearl, this post is already as long as a Lord of The Rings novel so for your sake I will save it for another time (you’re welcome).

#3 – Going back to work

On October 10, I started back to work! I wrote about the conflicting emotions that I felt in this blog post, if you want to read. As I write this to you, it’s been 1.5 weeks of being back to work & all I can say is that it gets easier/more smooth every day. We are finding our groove!

In hindsight, I wouldn’t change a thing about how I prepared for maternity leave. I truly believe the reason it worked so well is simple: I took time to connect with what felt right for me & was able to trust my intuition to help me plan, prepare, & execute it in a realistic way.

***If you’re an entrepreneur & are preparing for maternity leave, the ONLY advice I have to give you is DO WHAT FEELS BEST FOR YOU. You know your business, you know your heart, & you know what you need more than anyone else! Trust in that.***

If you’re still reading (I know… SO LONG RIGHT?!), I hope it was helpful!

xo, Sim

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  1. Gail says

    Love your plan, Simi!
    I saw it through in you & knew it was entirely true to your heart! You’re right on when you say centering & listening brings you to a place of vivid decision making… may you always feel the freedom to work with God on those choices!


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