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How I Prepped for a 5-Month Maternity Leave as an Entrepreneur

June 14, 2022

One year ago today I was preparing for my first maternity leave as a business owner. As an entrepreneur, I had no idea what to expect from creating my own maternity leave and there really weren’t any resources available for how to prepare for a maternity leave as an entrepreneur. There still isn’t. 

I was recently on a podcast recording with a new friend who was dreaming of one day creating her own maternity leave as a business owner and she asked me for advice, my experience, and a podcast all about it. Honestly I didn’t feel like an expert – nothing went exactly as planned, and even if I share my story my team makeup at the time was different and smaller than a lot of other business owners. I was struggling to see how my story would benefit anyone. 

But, I know one thing. I planned well, and strategically. The practical applications may look different between my business and your business, but the approach to planning can be the same!

So, in today’s episode of the Joy to Lead Podcast I’m pulling back the curtain on my 5-month maternity leave, focusing specifically on how I prepared and structured the maternity leave as an entrepreneur and how you can do the same.

My Priorities in Planning my Maternity Leave as a Business Owner

I’ll say it once and I will absolutely say it again later on in this post. Our primary focus when preparing for parental leaves as business owners is to birth the business first, then the baby.

For me, this looked like making sure: 

  • My departmental operations were detailed, structured, simplified and systematized. If I could automate them, I did. If I couldn’t, I hired. 
  • My team felt entrepreneurial – this is THEIR SHOW and any metrics and growth we see during my time off is DIRECTLY attributable to their work
  • The Leadership Academy experience was elevated exponentially – stellar guest speakers, and making room for leaders to step up within the community
  • My health is a priority – I did less in my business because I needed to spend more time moving, spending quality time with my daughter, and prepping for postpartum. 

Focus Areas of My Maternity Leave Preparation

Like I said before, my ultimate goal was to birth the business first, then the baby. I needed what was living in my head to live in some way, shape, and form outside of my head. Inside my head, I was the only one who could manage it. Outside my head, the business lived as a product, in systems, and in automations that could be managed by others.

I needed to get it out so I could get myself out of the business for a period of time. So, that meant disentangling my brain and my business. 

My main focus areas were team, marketing, and client operations and management. My business model is a community and digital product model, so my goals were to make sure that new members could access content, the community, and events while I was gone. 

Here’s what I did for my business for each of these areas.

Team Preparation

Like I said, I don’t have an agency model or a huge team. In fact, heading into pregnancy I only had one team member, my content manager. Her role was to promote the podcast and manage post-production materials. Heading into maternity leave, I hired a temporary operations and program manager – you can view her job description here

Marketing Preparation

In the Do Less, Play Smarter spirit, here is what I did marketing-wise to prepare for my maternity leave.

  • I repurposed my best email content from 2019-2020 to create high-value emails and scheduled those suckers out from June through December. I even recycled an old launch sequence and gained three new Academy members while on leave.
  • I dove into all of my notes I ever wrote – ever. And, what a treasure trove! I found Google Docs and iPhone notes full of thoughts I then turned into Instagram posts and weekly newsletter emails. 
  • I recycled, recycled, recycled content. If I wrote it, it lived as an Instagram post, email, and podcast. 
  • My content manager maintained the momentum of the podcast and promotional materials. I recorded as many new episodes as I could, but then set up replays of what I considered “hidden gems” – podcasts I knew were golden but didn’t have as many listens.
  • I launched a referral program to my Academy students, which was a success. 

Client Operations Preparation

My goal for client operations was to elevate the experience within my community and finalize product creation. Here’s what I did:

  • Finished creating and recording the actual course. This was a huge endeavor and took up most of my time during pregnancy.
  • Organized guest speakers for inside the community and tasked my operations and program manager with connecting with the speakers and hosting those calls. 
  • Asked for support from my mastermind and community to have support leading co-working calls and book discussions in the community.
  • I sent an email two months out to all clients letting them know of what was happening behind the scenes and detail what they could expect while I was on leave. You can view that email here! (I got several messages from clients about how much they loved this email.)

What I Ditched While Prepping for Maternity Leave

Simple is better, and done is better than perfect. I had to keep telling myself and my team this. I had to learn to show up every day prior to maternity leave asking myself and my team, “what can we ditch today? What am I focusing on that is absolutely distracting me?”

I felt this deep fear like the clock was ticking. I was so consumed with the worry about financials that I let shiny object syndrome derail me several times. For example, I launched a series of workshops I then had to step away from, and I was preparing this huge launch I had to scale back, and I was pushing myself to record a million new podcasts when my content manager simply recommended we promote replays.

My point is – this is not a race and it is not the end. Yes, secure your finances for your team and your business (also, you should really be saving far in advance for this so you don’t feel desperate and scared in advance of maternity leave – which should be joyful!). But, you need to release the guilt and fear and scarcity mindset to adopt an, ‘it will all be okay’ mindset. Because it will. You and your baby will soon meet, and that is all that deeply matters.

What helped me here was becoming okay with worst-case scenarios. If I had to refund all my clients and shut down my business tomorrow, could I do it? I could, and that’s okay. I knew I’d figure it out, I’d find a job, I would get back on my feet somehow. Once I became comfortable with that fear of losing my job and that income, I also became comfortable with any potential situation in between – and I was able to create contingency plans in case anything went awry. (It shouldn’t be this way. Entrepreneurs should have more parental and financial support, but this is the reality. We have to wonder if taking a leave means losing income. It sucks.)

How I Structured the 5 Phases of My Maternity Leave

I broke preparation and leave into 5 phases, each with their own objective that fueled my ultimate goal – taking two entire months completely checked out. Here is my timeline below – my due date was July 26 (and he was born July 8… or was it 9th?).

Preparatory Work in April/May

My goal in my second trimester was to ensure the foundation of my Leadership Academy by finalizing the curriculum as much as I could and automating onboarding completely so that this offering was self-automated, found temporary operations manager and created role and prepped for onboarding. 

Phase 1: June (T-8 Weeks to Due Date)

Goal is to serve and set the team and clients up for success, temporary operations manager. This is when I sent my detailed email to clients, held last client coaching sessions, and had several 1:1 and all-team meetings. 

Phase 2: July (T-4 weeks to Due Date)

This is when I began my leave, but I remained in a supportive role for my team until the baby came. Client facing, I was out. Team facing, I was in. 

At this point I was ready to be completely out when need be, the team had everything handled, but I was available fully for my team as they began leading and managing operations without me. It was a great buffer period. 

Also, I had no Asana tasks in this phase. I had one Asana task called, “Kaylan Goes into Labor.” My only job was to ping her when I went to the hospital, then she activated that task and went into “GO Mode.” The task didn’t have much on it, since I had scheduled so much already, but it did have her send a message to my other team member and my community.

Phase 3: August & September

COMPLETELY OUT. If I wanted to work, I had a list of projects prepared that were pre-approved by me, like working on my website. I knew I had to respect my own boundaries and protect myself from jumping in and confusing my team and community. I made a list of projects, but I never touched them.

Phase 4: October

This was my transition month. To my clients, I was still out. To my team, I was peeking back in. This was my space to discover and settle into a new routine and get back into podcasting and creating curriculum. 

Phase 5: November

Now, I was back and showing up for clients on November 4! I still had support from my operations manager this month, then she offboarded in December.

My Top Tips and Takeaways from My Maternity Leave as a Business Owner

  • Prepare saving now for a leave of absence, no matter if you’re planning a maternity leave this year or five years from now. And, it doesn’t matter if you’re even planning to take a maternity leave ever – this is great for general leaves of absence. I have a mastermind sister who was unexpectedly hospitalized in the ICU earlier this year for 10 days. You don’t expect to have to take long leaves, but is your business okay if you must? Here is her podcast all about her top tips for making sure your team is prepared in case of emergencies. 
  • Utilize and LEAN ON your support systems, there will be blockages and mental blockages, you won’t always see through issues clearly – my mastermind ladies came through here for me
  • Ask for help even if you feel guilty – you’d do the same, wouldn’t you?
  • Hold your plans loosely – they won’t go as planned. My maternity leave went great, but I had planned for 5 months and that was it. I wasn’t expecting the experience I had, so I actually ended up pausing a lot after that 5 months, like the podcast, team ops, and social media. I did only the bare minimum because I was struggling. 
  • Refrain from making any major decisions until you are back from leave – and perhaps until later
  • Get a therapist
  • Practice affirmations now
  • Make your health a priority
  • Get outside
  • Remove input and truly relax
  • Make postpartum prep all about YOU. The baby needs two things – diapers and food. That’s it. YOU need more because you have to give of yourself. So get all the cute postpartum clothes, get all the relaxing bath and body stuff, hire a cleaner, prep freezer meals and stock up on gift cards.

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I'm Kaylan, leadership educator, podcaster & speaker

What are you searching for?

Reading suggestions

Crafting a 90-Day Onboarding Plan

Job Postings that Attract Top Talent

Mapping Your Leadership Style