3 Key Strategies for Taking Parental Leave as an EntrepreneurFeatured

If you are a founder, entrepreneur, or otherwise self-employed person whose business building journey has intersected with growing your family, you have probably Googled some version of “how to plan for parental leave as an entrepreneur” only to realize that it’s hard to sort through the useful info and the horror stories.

As the only high-income country without a federal paid leave policy, states and corporations have often tried to fill in the gaps left by lack of national policy – but self-employed folks fall through the cracks all too often. The reality of there being no safety net, much less a road map or commonly discussed best practices for planning parental leave as a business owner makes it hard to know where to start, or what to include in your plan.

In my years as a parental leave consultant, specifically for female founders running service-based businesses, I have seen a handful of strategies that can be implemented across business models. They’ve been implemented by design agency founders, accountants, lawyers, coaches…you name it. Their businesses, as well as their personal needs, varied greatly, but they all wanted a smooth transition to parenthood for themselves and their ventures. Let’s dig in!

Strategy #1 Assessing and revising core business operations

When you are still in the weeds of your day-to-day business operations, pregnancy can be a forcing function to begin to streamline and delegate. Carving out a weekly block of time to work on operations from the moment you find out you are expecting can ensure that you and your team gain clarity on what has to happen to keep the business running smoothly.

How do you use your weekly block of time to work on your operations?

  • Track your time for a two week period, and then sort all processes that are on your plate into categories: pause, batch, automate, delegate
  • Identify any quarterly or infrequent tasks that will occur while you are out and assign a point person to own those
  • Create or update standard operating procedures for any undocumented or out-of-date process
  • Train team members on processes they will be taking over
  • Rightsize projects and team members’ time based on the processes they will own while you are out

A fun way to try out your new operations manual and identify any kinks that need to be worked out before your leave? Book a babymoon where you are offline, and run a debrief with your team when you get back. Doing this before 35 weeks gives you time to work on any issues that arise!

Strategy #2 Figuring out how to fund your leave

For founders and entrepreneurs working in the United States, where there is no federal paid leave policy or infrastructure, the reality is that most business owners fund their own leaves. This often means that taking leave as a small business owner requires having the foresight to plan ahead, even before you are expecting.

Thinking about growing your family down the road? Purchase short term disability insurance

This can be purchased through your insurance broker, similarly to other business insurance policies you may purchase. Pregnancy is one of the “conditions” that is covered, and you should discuss the details with your insurance broker of how many weeks and the amount that will be paid out. Some of the typical amounts of coverage I have seen are 6-8 weeks at 40-60% pay.

Preparing the business for pregnancy in the next year? Build up your reserves

If you do not already have a cash reserves account for the businesses, now is a great time to start one. Open an account or use a digital envelope system to begin to put away a percentage of profits. Aim for 3 months of operating expenses, at minimum, including any salaries or owner draw’s you would expect to take during leave. In addition, you may want to consider a lump sum for any contractors that would be needed during your time out to continue to run the core business operations.

Pregnant? Explore state benefits you may have access to

Some states in the US (Rhode Island, California, New Jersey, Washington, Massachusetts, Connecticut, and Oregon) and the District of Columbia have paid family leave laws that can be used to cover recovery from birth and/or family bonding when a new child is born, adopted, or placed in foster care. It’s important to note that each state has differing qualification requirements, and the weekly maximum benefit varies. If you live in one of those states, you can familiarize yourself with the eligibility requirements here. Those funds are earmarked for folks to use during this important transition, so take advantage of them!

In addition to exploring what funds you have access to through your business reserves, state-level benefits, or private insurance, take the time to review your personal finances. Having clarity on your personal and family financial needs can help inform what needs to happen on the business financial side.

Strategy #3 Building a support network for your leave and return to work

Before I became a mother myself, I learned one of my most important lessons about motherhood in an unlikely place: a museum mural. Painted in the 1920’s by José Clemente Orozco on the interior courtyard wall of the Museo San Ildelfonso in Mexico City is a mural entitled Maternidad (or Motherhood in Spanish). The mural depicted something that age-old wisdom and cultural norms around becoming a parent show to be true: social support matters.

The central figure in the painting is a mother with five people around her. None of them were oohing and aahing over the baby; rather, they were present for the mother. These five people represented her community, the people in her corner. The placard at the museum actually described these bystanders as “five figures displaying a protective attitude.”

Identifying your protective figures is a way to support your transition into parenthood, including navigating parental leave and the return to work.

How might you identify these supportive people in your own life?

During pregnancy

Spend an afternoon mapping out your current support system using a tool called an eco-map. An ecomap is a visual tool that helps us assess our connections with family, community, and social networks, paying special attention to the quality of these relationships. An ecomap can help you identify which of your connections could play a helpful role in helping you transition into parenthood (and which may be stressful and need boundaries) and explore any gaps in support that you may want to work on filling in before you are in the postpartum period.


Attend a new parent group, either virtually or in person, if you are comfortable doing so. You can search to see if birth centers, birth workers, or community-based organizations in your local area host groups. They may be led by a peer leader, birth worker, or mental health professional and can be low to no cost.

I will always remember the first in-person gathering of new parents I attended: my newborn screamed for the entire car ride over, then slept through the next two hours as I cautiously poured my heart out and listened to the other eight people do the same. Postpartum Support International hosts several affinity- and identity-based support groups for new parents who are Spanish-speaking, Black, queer, Desi, military, or have a child in the NICU. You can learn more and enroll here.

Returning to work

​​Connecting with other working parents before you return to work means you will have a cohort of people going through similar experiences. Since founders and entrepreneurs are unlikely to have a built-in Parents/Caregivers Employee Resource Group that are often set up at larger companies, you can informally build your own via an online community or a mastermind. The group can help normalize the hard moments, and individuals can offer support and camaraderie.

You can do this!

While there are many unknowns in becoming a parent, especially for founders, these key strategies can help you build a parental leave plan that considers the health and success of your business and your family during this important life transition.

If it feels daunting to begin to plan, take the time to remember a challenging phase in building your business - you have the tools and tenacity to do this too!

If you have built a parental leave plan yourself, add your favorite strategy in the comments, or share this Spotlight publicly along with your own experience. While we fight for paid leave policies to protect our businesses’ viability to weather the inevitable changes that life brings, we also need to share our creative solutions to parental leave and increase access to information and social support, so all expecting entrepreneurs are aware of the possibilities within reach.


Arianna Taboada, MSW, MSPH (she/her/ella) is the founder of The Expecting Entrepreneur, a consulting firm that helps entrepreneurs design parental leave plans that meet their business model and personal needs. Arianna speaks and writes about parental leave and respectful maternity care as an issue of social justice, human rights, and economic equity. She is the author of The Expecting Entrepreneur: A Guide to Parental Leave Planning for Self Employed Business Owners (2021) and a co-author of the anthology Degrees of Difference: Reflections of Women of Color on Graduate School (2020).

That was wonderful! Thank you so much for sharing your knowledge and resources with the community :D
Glad to hear it @brianarani !
This is fantastic! I love the focus on finding your people who will support you, not just the baby. This is so important as it's not just the physical challenges postpartum but the identity shift women experience.
1000% agree @HeyBloomwellTara !
for more like this. THANK a lot.