Shift Happens: Advice For Navigating Transitions

Throughout our Josie Shift Happens series, we asked leaders to reflect on the transitions that shaped them. They discussed how they navigated career and role transitions, work structure and environmental shifts, family planning and expansion, childcare and school changes, developmental parenting transitions that impacted work, family systems and caregiving complexity, and emotional and psychological career inflection points.  

Before we wrapped, we asked the group of experts and leaders one final question:

What is one piece of advice you’d give a working parent who is going through this kind of transition for the first time?

The responses were practical, honest, hard-earned, and deeply human.

We’re sharing their incredible wisdom and advice here in full.

 

Beth Wanner

Founder + CEO, Mother Cover

Read about matrescence and feel empowered by the transformation you’re going through. 

Transitioning into being a working parent is hard but you’re more powerful now than you were on the way out. Even if it doesn’t feel like that every day. You’ve got this.

 

Lily Walla

Founder + CEO, Auggie

Give yourself permission to be new at this. You do not have to have it all figured out on day one.

 Transitions take time, routines need adjusting, and emotions can be mixed. Ask for help sooner than you think you need it, communicate openly about what’s working and what isn’t, and remember that being stretched in this season does not mean you’re failing.

 

Michelle Keefe

CEO, MomUp

Every transition with kids comes with a fantasy version of how you should be handling it, and measuring yourself against that fantasy is what burns you out, not the actual work of parenting. 

Lower the bar from perfect to present. 

Pay attention to the openings your kids give you, even the small ones, and let yourself off the hook for the ones you miss. The goal isn’t to get it right every time, it’s to keep showing up so you’re there when it counts.

 

Deborah Porter

Workplace Parent Consultant

Lean into this new version of you—ask for help, set your priorities, and let good be good enough (at least in some areas). 

Keep a running list of things you could use help with so when someone asks, “How can I help?” you’re not trying to come up with something in the moment. Remember, you are a limited resource. 

Make note of the shift in your capacity and adjust without apologizing for it. There’s no prize for doing it all.

 

Bosky Mukherjee

Founder, SheTrailblazes

Stop comparing what works for others and why it may not work for you. Every family dynamic is different. So do what feels right for you and your family. 

And always have a circle or a tribe that you can reach out to. If I did not have the moms in my community SheTrailblazes, I have no idea how I would recover from all the crazy situations.

 

Helen Kupp

CEO, Women Defining AI

I always say it’s like airplane safety: put your oxygen mask on first, before you help others. 

You have to prioritize what will keep you sane, grounded, and breathing. Don’t forget that when you’re in the throes of trying to do it all for everyone else BUT yourself.

 

JR Butler

CEO + Founder, Shift Group

Your kids will remember you forever and be the ones that carry on your memory. Your coworkers, customers, partners, investors, bosses… will not. Choose your priorities accordingly.

 

Tina Cartwright

CEO + Founder, Rebranding Motherhood

My biggest advice? Ask for more support than you think you need—and then triple it. 

This transition into working motherhood is one of the most demanding, identity-shifting experiences you’ll ever navigate, and too often the focus is entirely on the baby while mom gets left out of the care plan. You need support around you—how you’re eating, how you’re resting, how you’re physically and emotionally recovering. 

That level of intentionality isn’t a luxury, it’s what allows you to actually heal and show up in both your work and your motherhood in a sustainable way. When you build a system that supports the mom, everything else has a much stronger foundation.

 

Alex Egeler

Career Clarity Coach, Empathic Egg

The best part about our kids being in the local public school is the neighborhood feeling. My advice is to work hard at building the village. There have been days off where parents we know have texted and said, “I have a meeting I can’t be distracted on this day off—can I send our son over to you for the morning?” And we have needed that support sometimes as well. Getting to know the other families, volunteering at the school, and finding people you trust can take a big burden off this issue. 

Raising kids was never meant to be a measure of your independence—it’s a team sport. Build your team as best you can.

 

Nicole Herrera

Keynote Speaker + Career Coach, Founder, Her Era

My one piece of advice to working parents going through big transitions with childcare or back to school is to take care of yourself too. Remember that you’re going through the transition too. 

Back-to-school can be a big emotional shift, especially if drop-offs are hard. Instead of rushing straight into work, take a beat after you leave. Breathe, reset, and give yourself space to process before stepping into your day and jumping into productivity mode.

 

Alexa Starks

Founder, Mothered Media | Editor-in-Chief, Mothered Magazine

Be patient with yourself, and don’t internalize the guilt. That guilt is you trying to live up to societal expectations. You’re a good parent and if it feels hard to balance it all, it’s because it is hard to balance it all. Give yourself time to adjust.

 

Lisa Kaplowitz

Co-Founder + Executive Director, Rutgers Center for Women in Business

Give yourself grace and space. 

Grace to get it wrong and not have all the answers, and space to both enjoy the moments and also remember to make time for yourself.

 

Harris Fanaroff

Founder, Linked Revenue

Take care of your spouse and focus on that relationship first and foremost. That’s the most important relationship to get right.

 

Leanne Wong

Executive Coach + Fractional Talent Management

You can’t eliminate the demanding nature of this position—but you can reduce the pressure by choosing what matters most, and building support around that.

 

Javaree Walker

Founder, Ready To Dad

You aren’t expected to have all the answers right away, and putting too much pressure on yourself will only make things tougher. Focus on what matters most to you right now and let that shape your decisions, rather than trying to meet every expectation at once. 

You don’t have to become your old self to move forward. Be as patient and kind with yourself as you would be with anyone else going through something this big for the first time.

 

Paige Connell

Content Creator + Founder, Turner Collective LLC

Don’t put too much pressure on yourself to make it look seamless right away. It’s going to take some trial and error. Some things will work, some won’t, and that’s part of it. Give yourself time to figure out a rhythm that actually works for your family. 

The goal isn’t perfect, it’s sustainable.

 

DeAnna Taylor

CEO + Executive Rest Coach, Mom-Care Oasis

Don’t get discouraged the first time you speak up for yourself and it doesn’t land the way you hoped. Everybody isn’t going to clap for your boundary at first. You might get side-eyes, sarcasm, or even silence. But that doesn’t mean you were wrong. 

Keep advocating for yourself. Don’t ask for permission to take care of your capacity. 

Stand on what you said you need, and say it again if you have to. Because over time, people adjust. What feels uncomfortable right now becomes the new normal in your home. And more importantly, you start showing up as a version of yourself that isn’t constantly running on empty.

 

 

Give yourself grace. Lower expectations. Accept limits. Ask for support. Stop comparing yourself. Take care of yourself. Remember what matters most.

You got this!

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