How-to Plan a Maternity Leave (or Vacation) as an Entrepreneur

Jenna Kutcher 

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September 19, 2018


This Goal Digger Podcast episode is all about planning for a maternity leave as a small business owner. The how-to, what to know and how to plan.

It’s crazy to think that in a few short months, we’ll be welcoming a baby into our home and lives and everything will change. If you’ve followed our journey for a while, you know that our road to baby hasn’t been easy. Before we dive into how I am preparing for a true maternity leave, I want to share a little bit of how my business has transformed in the last 2.5 years while we were waiting and struggling to start our family… AND tell you the five big things I am doing to prepare for maternity leave:


First things first, what does my perfect year look like? I needed to get really honest with myself in what would make me feel free and not tied down to work while also feeling like I had a plan or some sort of structure so that I didn’t feel like I would totally fall behind or my business would implode. As someone who has had workaholic tendencies for years but is pulling herself out of them in this season of pregnancy, I want to make sure to protect my time with our new baby while also knowing that when I’m ready to get back to work, I have a solid plan in place and something that excites me.

My vision: Have the baby early December, plan for 3 full months off, so December, January, and February. We will spend the entire month of February in Hawaii keeping our annual sabbatical going strong, we’re super excited about this part and just getting to explore life as a family of three on the island. During this time I will check in with my team 1x per week and then try to stay out of the inbox. The only “work” we’ll be doing is photographing our little bundle and sharing our lives online. Following maternity leave, I will settle back into business as usual which will look like one big course launch per quarter, 2 podcast episodes per week, a few bigger brand sponsorships and creating new content to be shared. I am saying no to all speaking opportunities for the year to be home more and not on the road as much and then deciding if we will do another mastermind and if so, what that will look like.


Once I knew what the vision of my leave was going to look like, I wanted to give myself flexibility in it. To be honest, I know our minds will be blown and I have no clue if I will be chomping at the bit to get back to work or if I will be yearning for more downtime with the babe. I wanted to give myself the space to have no work obligations for up to 6 months just to give a little more time and mental space in case I am just digging that mom life so much that I want to ease back into work! I let my team know to turn down all speaking requests for next year (I’m talking all of them) and we decided that this will be my last season shooting weddings, so we are closing that chapter and sending recommendations to any photography requests. We also formulated a plan to record over 50 podcast episodes in advance to support the podcast while I am on leave so that our content is still going out each week and then broke down a content calendar for the blog and Pinterest.

My team and I mapped it all out and we split up who was doing what as we prepare for leave. It definitely added more work for my team in terms of preparation but at the same point, we are usually working ahead to an extent so having a plan just meant we needed to supercharge our batch working and divide and conquer plan!


If you’ve ever heard anything of mine, you know how much I love automation. Automation has absolutely changed EVERYTHING for me in my business and so once we knew that I sincerely wanted 3 months where I wasn’t working or actively creating, I knew that I had to get super serious about automation and optimizing the things that would be running while I wasn’t. As it stands, we have 3 courses that are in automation currently and so instead of following the plan I set at the beginning of the year which included creating a brand new course, we pivoted and instead focused on updating and optimizing everything that is in automation: I’m talking course content, webinars, ad copy, and images.

We wanted to get all of our automated offers running great so that they could be served to my audience while on leave and also help us be generating income while signed off. I also had a big goal of expanding my email sequence (which is currently 6 months long for a new subscriber) and making sure that every new person that opted in was being served consistently with a well thought out sequence that would share our different offers based on what people needed the most help with while also putting them into segments that would allow us to serve them better in the future.

When it comes to automation, we wanted to have everything pre-scheduled before baby comes, so that looked like: 2 podcast episodes a week, a Friday blog post each week, one email to my full email list per week, and then corresponding social media posts to push out that content.


One of the biggest lessons I’ve learned in running a team is the power of communication and really working together. In months leading up to this leave we’ve been much more connected, partnering together on plans and then setting expectations for while I am out. I’ve also started communicating with my audience about what they can expect will happen when baby Kutcher happens, (ahem, this episode!) so that everyone is on the same page for what that break will really look like. I want my team to feel empowered to care for my business like it’s their own and to work together to troubleshoot or make decisions.

By the time baby comes, my entire team will all have been working with me for a year or more, which evokes total confidence in their abilities (and let’s be honest, they ran the show when I was laid up in bed with terrible morning sickness!) I wanted to have plans for the inbox, plans for who was posting what, who had ownership on which parts of the business, and how the team would communicate while I was out. We’re a team that respects boundaries so I’m not at all concerned with getting a million texts a day asking questions or being bombarded by my team because they don’t know what to do while I am out.

My team functions incredibly when I am laying low – in fact, I love when I am out of the office because it gives them a chance to create their own routines around their flow states and adjust work to match their life a little better.


This sounds silly, right? Duh, you’re going to prepare, but honestly, mentally preparing to take 3 months off from my business takes a lot of work. I used to believe I was incapable of rest – that my brain just functioned at a higher level than others and that I was wired to work. I believed this for years and years and leaned on it as a crutch and excuse to never take time away. The truth was, I didn’t fully believe that I had built something that wouldn’t crumble or fade if I stepped back for a bit. While we get ready for a maternity leave, I am doing a lot of work mentally preparing myself for taking time off. For letting myself find a new normal, a new routine without focusing on things like how many emails need to be answered or how many Facebook questions need answers.

I have been doing visualization exercises, been stocking up on fun books to read, been dreaming of how we will keep busy in the dead of a Minnesota winter, and just how we will navigate those first few months as a family of 3. I’m also really doing all I can to not set expectations. We have a unique circumstance in that Drew and I both work from home, we work together on projects, and we have ultimate flexibility which means that it might be totally possible to log in for a little bit if it excites me. I feel like in the past I’ve been black or white, I hold myself to these crazy standards so that I can say things like “I didn’t log in for a week straight,” but if this pregnancy and journey has taught me anything, it’s to be open-minded, trust my intuition, and to really believe that when the time comes I will know what is best for me and my baby.

So there you have it, my vision, plan, automation, communication, and preparedness around having a maternity leave. I know my world is about to be rocked, I know everything will change but I am welcoming this new season with open, imperfect arms and I can’t wait to share after maternity leave my big takeaways from stepping into this new season of life and what it’s really like trying to be a good mom and a badass entrepreneur. If you have any tips or ideas for me, I’d love to hear them. Hop onto Instagram @goaldiggerpodcast and let me know, I’m open to all suggestions from those who have walked this road before me! You can’t know what you don’t know, so there’s that! Until next time Goal Diggers, keep on digging your biggest goals!


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  1. […] It was so helpful to hear how other entrepreneur’s were planning their maternity leave, like Jenna Kutcher (Episode 189) & Micala Quinn (Episode 12). So like I said in the intro, I would recommend […]

  2. […] my maternity leave planning after listen to a phenomenal podcast by my girl Jenna Kutcher on How-to Plan a Maternity Leave (or Vacation) as an Entrepreneur. I have a few fellow marketing mavens jumping on board this month to help me maintain our business […]

  3. […] can literally run by itself (with a team firmly in place), if necessary. You all listened to Jenna’s podcast as she went on a long maternity leave, right? This was only possible because her business is optimized. She has the bandwidth to work […]

  4. […] can literally run by itself (with a team firmly in place), if necessary. You all listened to Jenna’s podcast as she went on a long maternity leave, right? This was only possible because her business is optimized. She has the bandwidth to work […]


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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