Growing Pains | Where Business Owners Come to Plan Maternity Leave
You’re running a business and dreaming of growing your family, but when you search for how to take maternity leave as a self-employed mom, the answers just don’t exist.
You’ve pieced together advice from HR blogs, asked your friends, downloaded generic templates, and tried to “figure it out later.” Meanwhile, you’re left wondering: Can I really step away from my business without losing momentum...or my mind?
Here’s the truth: You can. And Growing Pains is here to show you how. Hosted by maternity leave strategist and business operations expert Alyson Caffrey, this podcast helps self-employed moms plan for maternity leave during the trying to conceive, pregnancy, and postpartum seasons—without burning out or ghosting their business.
Each week, you’ll hear honest solo episodes, expert interviews, and real-life maternity leave stories from moms who are building legacies and raising babies. No fluff. No one-size-fits-all advice. Just grounded guidance to help you navigate life and business on your terms.
Alyson has helped hundreds of entrepreneurs streamline their operations and take actual time off for maternity leave, while returning to businesses that thrive.
Ready to take maternity leave like a CEO? Follow Growing Pains and let’s build a business that supports your motherhood journey.
Episodes
124 episodes
The Power of Community and Intuition – Maternity Leave Roadmap #23
It’s easy to feel like you should have a village around you during motherhood and business. But what happens when that village doesn’t show up?In this episode of the Maternity Leave Roadmap series, I’m talking about the two forms of supp...
•
Episode 123
•
11:03
The Identity Shift of Motherhood and Business – Maternity Leave Roadmap #22
The biggest shift in your maternity leave plan isn’t logistical. It’s personal.In this episode of the Maternity Leave Roadmap series, I’m sharing what that identity shift looked like for me, how it caught me off guard, and why it ultimat...
•
Episode 122
•
10:43
The Frontload Fallacy – Maternity Leave Roadmap #21
You’ve probably heard it before: just get everything done before baby comes. But what if trying to frontload your entire business is actually setting you up to fail?In this episode of the Maternity Leave Roadmap series, I’m breaking down...
•
Episode 121
•
9:30
Block a Day to Implement – Maternity Leave Roadmap #20
You’ve done the planning. Now it’s time to actually start building.In this episode of the Maternity Leave Roadmap series, we’re entering the implementation phase. I’m sharing one of the most effective tools I’ve used (and that we use ins...
•
Episode 120
•
9:38
The Only 3 Problems in Your Business – Maternity Leave Roadmap #19
By now, you’ve probably uncovered a few areas in your business that need support. But what if diagnosing the real problem was simpler than you think?In this episode of the Maternity Leave Roadmap series, I’m sharing what I’ve learned fro...
•
Episode 119
•
8:52
Audit Your Finances Before Leave – Maternity Leave Roadmap #18
You don’t need to sell more to afford your leave. You need to start with the money you already have.In this episode of the Maternity Leave Roadmap series, I’m walking you through a step-by-step financial audit that helped me return from ...
•
Episode 118
•
10:19
Should I Get Insurance? – Maternity Leave Roadmap #17
Most business owners wait until something goes wrong before they think about insurance. But when you’re planning maternity leave, thinking ahead is a gift to your future self.In this episode of the Maternity Leave Roadmap series, I’m bre...
•
Episode 117
•
7:55
What Does My State Offer? – Maternity Leave Roadmap #16
One of the biggest questions I get from self-employed moms planning their maternity leave is: Does my state offer anything to help?In this episode of the Maternity Leave Roadmap series, we’re breaking down the truth about state ...
•
Episode 116
•
5:57
Schedule a Beat for Yourself – Maternity Leave Roadmap #15
There’s so much talk about prepping your business for leave, but what about you?In this episode of the Maternity Leave Roadmap series, I’m inviting you to schedule something we rarely give ourselves: space to feel. Whether it’s journalin...
•
Episode 115
•
8:38
Create Your One-Page Leave Plan – Maternity Leave Roadmap #14
There’s a moment in your leave planning process where things shift from ideas to action. This is that moment.In this episode of the Maternity Leave Roadmap series, I’m walking you through the exact structure of your one-page maternity le...
•
Episode 114
•
7:41
How to Tell Your Clients You're Pregnant – Maternity Leave Roadmap #13
If just the thought of telling your clients you're pregnant makes your stomach drop, you're not imagining it. This is one of the trickiest parts of maternity leave planning.In this episode of the Maternity Leave Roadmap series, I’m walki...
•
Episode 113
•
8:33
Give Your Team the Baton – Maternity Leave Roadmap #12
Delegation isn’t just about handing off a task. It’s about trusting someone to run with it, even if they do it differently than you would.In this episode of the Maternity Leave Roadmap series, we’re shifting from theory to practice. I’m ...
•
Episode 112
•
7:59
Find Your Leading Indicators – Maternity Leave Roadmap #11
When something in your business feels “off,” the answer is usually upstream.In this episode of the Maternity Leave Roadmap series, we’re talking about leading indicators aka the activities that directly impact your results. Whether you’r...
•
Episode 111
•
8:57
Track Your Business Like a Coach – Maternity Leave Roadmap #10
You can’t manage what you don’t measure, and when you’re preparing to step away from your business, your data becomes one of your most powerful tools.In this episode of the Maternity Leave Roadmap series, I’m sharing how to get your data...
•
Episode 110
•
7:14
Design Your Perfect Week – Maternity Leave Roadmap #9
If you’re ending your weeks exhausted and wondering, Why did that feel so hard?—this is your sign to pause and reassess.In this episode of the Maternity Leave Roadmap series, I’m walking you through one of the most helpful tools...
•
Episode 109
•
8:21
Block and Tackle Like a CEO – Maternity Leave Roadmap #8
You soon won’t have the bandwidth you used to. That’s not a weakness—it’s a turning point.In this episode of the Maternity Leave Roadmap series, we’re talking about how to protect your time by learning to block and tackle. I’ll walk you ...
•
Episode 108
•
7:22
The 4 Core Systems Every Business Needs – Maternity Leave Roadmap #7
Most founders are stuck in the weeds not because they’re doing something wrong—but because their business is missing a system.In this episode of the Maternity Leave Roadmap series, I’m sharing the four core systems every business needs t...
•
Episode 107
•
7:27
Build Your Central Source of Truth – Maternity Leave Roadmap #6
Most team breakdowns don’t happen because of bad intentions—they happen because no one knows where to find what they need.In this episode of the Maternity Leave Roadmap series, I’m walking you through one of the most powerful tools you c...
•
Episode 106
•
6:04
How to Delegate with Clarity – Maternity Leave Roadmap #5
Want to delegate with confidence before baby comes? It starts with one simple habit.In this episode #5 of the Maternity Leave Roadmap series, we’re building on your outsource list from last time and getting tactical. I’m walking you thro...
•
Episode 105
•
7:33
What Can You Afford to Outsource? – Maternity Leave Roadmap #4
When it comes to maternity leave planning, one of the biggest mindset blocks I see is this: “I don’t know if I can afford to get help.”In episode #4 of the Maternity Leave Roadmap series, we’re talking about time, money, and the numbers ...
•
Episode 104
•
7:41
Practice Taking Time Off – Maternity Leave Roadmap #3
We don’t build confidence by hoping things will go well—we build it through practice.In this episode #3 of the Maternity Leave Roadmap series, we’re shifting from intention-setting and time-blocking into real-life action. One of the most...
•
Episode 103
•
7:24
How to Make Time to Plan Your Leave – Maternity Leave Roadmap #2
Making time to plan your maternity leave doesn’t require a big life overhaul. You just need one focused habit.Welcome back to the Maternity Leave Roadmap series. If you’ve been wondering how you’re going to squeeze in planning between cl...
•
Episode 102
•
7:45
Welcome to The Maternity Leave Roadmap Series
Welcome to the start of the Maternity Leave Roadmap series. This is the beginning of something big.If you're a self-employed mom who’s thinking about growing your family—or you're already pregnant or postpartum—you’re in the right place....
•
Episode 101
•
7:41
When Grace Becomes an Excuse + Big Changes Coming to the Podcast
“Give yourself grace.” It’s a phrase we hear all the time—especially in motherhood and entrepreneurship. But what happens when that grace quietly turns into an excuse?In this special 100th episode of Growing Pains, I’m reflecting on the ...
•
Episode 100
•
15:31
Creating Connection Through Podcasting with Amanda Bennett
What if podcasting could transform not only your business but also your motherhood journey? In this episode, I chat with Amanda Bennett, a podcast guesting strategist and founder of the Podcasting Moms Club, about how moms can use podcasting to...
•
Episode 99
•
44:05