The 4 Ways I'm Preparing for Maternity Leave as an Entrepreneur

Becoming a parent is a major life milestone that leads to big changes. As a soon-to-be mompreneur, the shift from considering my business as my baby to becoming responsible for a living, breathing human being is overwhelming.

In the final weeks of pregnancy, I'm coming to terms with the fact that very soon, I'll no longer be completely in control of my daily schedule. I can't keep putting in long hours to advance business goals whenever necessary.

Even once I (hopefully!) start to get the hang of parenthood and tap into resources like daycare, I won't be quite the same person and business leader I was before becoming a parent. But I'm not willing to give up my entrepreneurial dreams because my personal life is changing.

Here's how I'm proactively planning to take time off for maternity leave without interrupting business operations and the growth goals I set out to achieve this year.

Pregnant employee working in conference room
Pregnant employee working in a conference room. Ramping up hiring, formalizing internal policies, prioritizing transparency and improving project management will help 'mompreneurs' prepare for maternity leave. Ridofranz / Getty Images

1. Ramping Up Hiring

I've previously shared about scaling my freelance business to an agency. Many of the same principles around delegating, creating efficiencies and assembling a support system will also help ease the transition to running my business as a parent.

I've always been the type of person who moves gradually with calculated risks in my business. But I've been quicker to green light and move forward with internal initiatives to get ahead while I still have available energy and attention leading up to my maternity leave.

After my late September due date, I'm not planning on being able to contribute many meaningful inputs or do deep work until the baby goes to daycare at the start of the new year.

As such, I'm working on proactively hiring for any position that I anticipate will need to be filled before the end of the year, even if that means starting them with limited hours and scaling up over time.

I want to make sure that there's a dedicated point person for every need so that existing staff do not feel overburdened by my absence.

Current hiring efforts are also focused on ensuring that there's more than one person trained to do any role so the business can continue to run smoothly in light of any personal emergencies, vacations and other situations that come up.

Creating clear onboarding and training paths reduces some of the burden on current staff to get new hires up to speed.

2. Formalizing Internal Policies

Transitioning from a freelance business model to an agency approach for The Blogsmith meant growing fast and being unable to proactively think through every single detail amid the chaos.

That's why, as we continue to grow and establish ourselves, reducing ambiguity and being upfront about standard operations for the team's reference became increasingly necessary.

As such, and knowing that I wouldn't be able to weigh in on situations that fall outside the norm during my maternity leave, I recognized the need to clarify certain internal policies.

The business needs to be able to move forward even when I'm not available, so setting guidelines other people can follow was an important part of my maternity leave preparation.

Here are the policies I've spent the last several months developing to provide clarity while I'm out of the office:

  • Detailed writer billing policies. Most Blogsmith team members charge by the hour. At this point in time, writers bill us primarily based on a per-word charge. Our writer billing policies clarify what's expected in a deliverable charged per word, when they can charge hourly and when they can charge in excess of what's initially approved and included in their per-word rate.
  • Raise eligibility policies. Creating clear raise eligibility policies sets better expectations for communicating when someone becomes raise eligible. It also clarifies the scale by which we'd potentially increase their pay, laying out how we make raise decisions relative to their performance and meeting other stated milestones.
  • A new independent contractor agreement (ICA). A lot has changed in the content marketing world since I last updated our standard ICA, like the proliferation of AI. In tandem with clarifying internal policies, I worked with a lawyer to add and further clarify contract clauses for Blogsmith team members and had everyone re-sign the document.

3. Prioritizing Transparency

I was initially nervous to announce my pregnancy to my team. Besides the usual concerns surrounding the early stages of pregnancy, I didn't want them to worry that it would threaten the future of the company and their roles within it. After all, I'm not interested in trading entrepreneurship for motherhood!

Regardless, this news represents change, which is uncomfortable. So, when I announced my pregnancy to the team, I wanted them to understand that if they needed anything from me specifically, now was the time to get ahead of the ask.

From there, I've been continuously checking in to move important projects forward and keep everyone thinking about how to capitalize on my last surge of energy before those inevitable sleepless nights on maternity leave with a newborn.

And yeah, I can't plan for all the details around what coming back from maternity leave looks like on this side of pregnancy—there are too many unknowns! But I've started thinking through some specifics for how it might go and the initiatives I want us to make a priority through the end of the year.

4. Improving Project Management Processes

In addition to being transparent with my team, and for me to fully embrace maternity leave, I needed to be sure they would follow systems for sharing transparent updates with me.

Our project management processes continue to improve over time, but I've recently set forth initiatives for additional measures to help me feel confident in taking a bigger step back.

Here are a few project management process improvements we're making in tandem with my maternity leave:

  • Following a robust meeting notetaking process. I firmly believe having a meeting isn't worth it if we don't have a clear accounting for it after it wraps. We use Fireflies.ai to capture a transcript for future reference as an important first step. Additionally, for any internal meeting that takes place, I want accessible notes that detail the agenda, decisions made and any follow-up actions.
  • Using a department-wide project tracker. Our project managers are primarily focused on client projects, but several internal initiatives also need oversight to progress effectively. To help manage this across all departments, we've launched a dashboard that provides transparency around planned projects and progress that project managers can access in one convenient place.
  • Intranet cleanup. We use Notion as a company intranet, and its structure hasn't been meaningfully updated since transitioning the business to an agency model. One of our big projects for this year has been cleaning it up to make it a better resource for each individual and department. Part of this effort has also involved creating a better process for storing notes and reminders that entire departments need access to.

Voyaging Into the Unknown

Building up a great team and setting clear expectations are the best ways I know how to move confidently into the next major era of my life as a mother. While it's impossible to predict how successful I'll be with balancing parenthood and entrepreneurship, I'm not panicking—I'm confident it will all work out the way it's supposed to.


About the Author

Maddy Osman is the author of "Writing for Humans and Robots: The New Rules of Content Style". Maddy's journey from freelance writer to founder and CEO of The Blogsmith yielded numerous insights to share about content creation for enterprise B2B technology brands. Her efforts earned her a spot in BuzzSumo's and Semrush's Top 100 Content Marketers and The Write Life's 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon and Denver Startup Week.

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About the writer


Maddy Osman is the author of "Writing for Humans and Robots: The New Rules of Content Style". ... Read more

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