😅 Boss’s Day: For Every Kind of Workplace Relationship

Hi Mamas - 

If you didn’t know, National Boss’s Day is coming up on October 16 — consider this your friendly reminder (and your chance to find something nicer than a “World’s Best Boss” mug 😅).

Love them, fear them, or are them — we all have some kind of relationship with “the boss.” But for many working moms, that word hits differently. Maybe your boss is a mentor who makes flexibility possible. Maybe you are the boss, juggling PTO requests and preschool pickup. Or maybe this year’s return-to-office mandates have made that relationship… a little complicated.

Wherever you fall, it’s worth pausing to think about what good leadership actually looks like — and feels like — in this season of work and life. There’s still time to celebrate (or survive) Boss’s Day this week — and maybe even reimagine what being a “good boss” really means.

Also, we sure would love if you’d share The CARRY ALL newsletter with another mama who needs it—we are so grateful hearing how much you look forward to getting this in your inbox every Tuesday. Would you share the love and share your referral link to another mama (or two)?

Enjoy!

-CARRY™ Team

 This week in The CARRY™ ALL, we’re talking about:

• 💼 Boss’s Day When You Are the Boss

• 🎉 Ideas to Celebrate Your Boss

• 😅 When Boss’s Day Feels…Complicated

THE BIG 1️⃣ 2️⃣ 3️⃣

1️⃣ 💼 Boss’s Day When You Are the Boss

The unspoken conundrum of Boss’s Day: when you’re the boss, who’s supposed to celebrate you? Do you throw your own party? Wait for someone to notice? Or just quietly pretend it’s not happening?

Absolutely not, ma’am! There’s no sitting around waiting to be celebrated — you’ve got emails to answer, fires to put out, and probably someone’s lunch to sign off on. The “boss” hat rarely comes with a pause button.

Leading a team (and let’s be honest, leading plenty at home, too) often means you’re the one cheering others on, making the tough calls, setting the tone. 

Permission granted: Take a minute to remember you count, too.

You don’t need a plaque or a post to mark it. Maybe it’s stopping for a little “just because treat” today, giving yourself credit for the growth you’ve led this year, or just acknowledging that leadership can be both rewarding and exhausting. 

You don’t have to have it all figured out to be a good leader. Just in case no one’s told you today — we think you’re doing a kick-ass job. 💪✨

2️⃣   🎉 Ideas to Celebrate Your Boss

Boss’s Day is the perfect excuse to show a little appreciation for the person leading your team (or at least signing off on your PTO requests 😉). Whether your boss is the “coffee before conversation” type or the “Slack message at 10 p.m.” type, a thoughtful gesture goes a long way. Think beyond the mug or gift card — write a quick note about a way they’ve made your job better, treat them to their favorite lunch, or rally the team for a short-but-sweet surprise. 

Sweet treats are always a win: consider a box of Baked by Melissa cupcakes (yes, they have gluten-free options!) or a classic Edible Arrangements bouquet. Delicious and thoughtful — it’s hard to go wrong. Sometimes the simplest way to celebrate a boss is just saying, “Thanks for making work a place we actually like showing up to.”

And here’s a twist: despite the usual grumbling about “dreaded managers,” a recent survey shows most employees actually enjoy working with their bosses. So why not lean into that positivity and celebrate the leadership that makes your workday better?

3️⃣  😅 When Boss’s Day Feels…Complicated

Listen, we get it — not everyone is eager to jump and cheer, “hooray for my boss!” This year, especially with return-to-office mandates hitting many workplaces, it can feel tricky. For a lot of working moms, navigating new rules, schedules, and expectations has made leadership feel less “supportive” and more… stressful.

So if Boss’s Day has you rolling your eyes instead of reaching for a card, that’s okay. You can acknowledge the day without pretending everything’s perfect. A small, honest gesture — like a kind note, a coffee, or leaving a thoughtful snack on their desk — can still count.

And if celebrating feels impossible this year, remember: Boss’s Day isn’t a mandate. If you can muster a small act, it would probably go a long way — but we get it if it feels more like a begrudging gesture than a genuine celebration.

📰 IN THE NEWS

Hiring Managers Weigh in on Gen Z Readiness

A new survey of 350 hiring managers is sparking conversation about how prepared Gen Z employees really are for the workplace. Only 8% of managers said they believe Gen Z workers are fully ready to hit the ground running, while most pointed to gaps in professionalism, communication, and in-person work experience. Still, many leaders say these challenges aren’t dealbreakers—they’re opportunities for mentoring and clearer expectations. The takeaway? Every generation needs a little guidance starting out.

Read more here: HERE.

BEEN THERE, DONE THAT 🤎
for the mom who is growing at work and at home

If you’re feeling like your career and motherhood are stretching you at once, that’s totally normal. Growth seasons can be equal parts exciting and exhausting. Here are a few reminders and practical ways to navigate both:

1. Define what growth looks like for you, right now.
It doesn’t always mean climbing higher — sometimes it means finding rhythm, rest, or confidence in your current lane. 

Give yourself permission to measure progress according to your current priorities. Clear expectations are a gift to everyone. You don’t need to do everything — just the right things for right now. 

2. Lean on support — at home and at work.
Whether that’s delegating more, using grocery delivery, or finding a trusted childcare swap, let others help carry the load. You weren’t meant to do this alone! 

3. Resource rec:
Book: “You Don’t Have to Carry It All” by Paula Faris — Ditch mom guilt that comes with trying to do it all.

✨ You can pursue growth and grace. It’s not easy, but it’s possible!

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