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☕️Cup of Ambition: The World’s on Fire & You're Still on Zoom.

Hi, I’m Kelly. Former HR leader turned Career Strategist with a love of Diet Coke, Dolly Parton, and iced coffee. I believe that who you are will always be more important than any job title, and a successful career is a strategic marketing campaign that puts you in control of your brand.

In This Edition… 

  • 9 to 5 Dilemma: The World is on Fire, But I’m on Zoom?

  • Over-Accommodation is Learned, Let’s Unlearn It.

  • Upcoming Events & Sessions.

  • Reflections from the Mountains.

  • Dollyism.

9 - 5 Dilemma

The world feels like it’s on fire politically, environmentally, socially. Every time I open the news, I feel a wave of dread or heartbreak. It’s all so much and it feels like every week it somehow gets more intense and uncertain.

And yet somehow, I’m still expected to show up to work like everything’s fine… attend meetings, smile on Zoom, hit deadlines, plan launches. I’m trying to stay focused, but it all feels a little absurd. How do I keep showing up when so much around me feels so heavy?

-Stuck on Zoom While the World Burns

Let’s just say what so many people are quietly feeling right now:

It’s hard to care about your inbox when the world feels like it’s crumbling.
It’s hard to plan a product launch when your chest is tight.
It’s hard to answer, “How are you?” without lying a little.

You are not alone in that, cause SAME.

Lately, I’ve had more than a few clients come into our calls carrying this strange weight. They’ll show up to talk about career strategy or navigating a tough dynamic at work, but first, they exhale. And they say something like:

“Honestly? Everything just feels really heavy right now. I’m trying to stay focused, but what’s the point of all this?”

They’re not being dramatic. They’re being human.

And still, the Slack pings. The meeting invites come in. Deliverables
The Q3 goals get posted. The messaging stays upbeat.

This is what emotional dissonance looks like.

It’s the disconnect between how you actually feel and what the workplace expects you to perform. It’s being in a moment of collective or personal grief, and still being asked to act like your biggest priority is deliverables.

And most of us have been trained to play along.
To show up. Smile. Keep it moving.
To push down what’s real and meet the moment with productivity.

But that’s not resilience. That’s erasure.

Here’s what I want you to know:

You’re not wrong for feeling off. You’re not weak for feeling like your heart is somewhere else. You’re not less committed because you’re carrying more than just your workload.

If anything, your ability to feel this much in a world that’s constantly telling you to numb out? That’s something sacred. Don’t pathologize it.

So instead of pretending nothing’s wrong, try this:

  • Let yourself show up honestly. “I’m here, but my energy’s a little low today.” That’s what real people say when shit gets tough.

  • Take small, intentional steps to protect your bandwidth. A five-minute walk. A Slack snooze. A breath before replying.

  • Find spaces where you can say the thing out loud. “I’m holding a lot, and I don’t want to pretend I’m not.”

And if you need to pull back a little this week, do.
You don’t need to justify being a person with emotions in a world that keeps testing your nervous system.

Here’s what’s true:

You can care deeply about your work and still feel overwhelmed by the world.
You can be grateful for your job and still struggle to focus.
You can be a high performer and still need rest, still need space, still need to not be okay for a minute.

So if you’re wondering how to keep going when it all feels like too much…
Don’t force it. Don’t fake it.
Just take the next honest step. That’s enough.

This week’s reflection:
What would it look like to let yourself be a little more real and a little less “fine”? Sometimes it just takes one person to speak up with realness.

Upcoming Events & Trainings

June 30 at 11:30 am EST
Register Here: lu.ma/event/manage/evt-8rYCz3Uuk4V4C1x 

☕ June AMA: Bring a Beverage & Let’s Chat

It’s time for another Ask Me Anything session—your chance to get real answers to whatever career questions are on your mind.

Thinking about a job change? Struggling with a frustrating boss? Wondering how to position yourself for what's next?

Bring it to the session and let’s unpack it!

Bring a beverage, bring a question, bring yourself.
No slides. No pressure. Just real talk about work, growth, and making bold moves with gumption.

“What’s Working, What’s Not, What Now?”

Wednesday, July 16 at 1 pm EST

Free to Cup for Ambition Readers & gumption. clients!

A mid-year check-in to get clear, get unstuck, and move forward with purpose.

Half the year is behind us, so let’s pause and take stock.

This 60-minute workshop is designed to help you step out of reactive mode and take an honest look at your work, goals, and mindset. Together, we’ll walk through a simple but powerful framework to figure out:

  • What’s working—and how to build on it

  • What’s not—and what it’s costing you

  • Where you might be playing small or staying stuck

  • What needs to shift in the second half of the year

You’ll leave with a clearer view of where you are, what you actually want next, and what needs to happen to get there.

This is for you if you’ve been feeling scattered, uncertain, or like something needs to change, but you’re not sure where to start.

You’ll also walk away with 3 key personal branding tasks to complete over the next 3 months:

  1. Refresh your LinkedIn headline and About section to reflect where you're going, not just where you’ve been.

  2. Identify one story or result from the last year that you want to start sharing more consistently in interviews, on LinkedIn, or with your manager.

  3. Update your resume using a clear, impact-driven format that actually reflects your strengths and voice (you’ll get my formula for this inside the session).

Over-Accommodation Isn’t a Flaw. It’s a Survival Skill You Don’t Need Anymore.

There’s a phenomenon across women at work, something that’s quietly draining a lot of smart, capable, badass women.


You’re constantly adjusting, anticipating, overdelivering, softening the edges of your words, and making it all look easy.


And you’ve probably been praised for it.

You’re “so adaptable.”
You’re “great under pressure.”
You “always know just what’s needed.”

But behind that praise is a pattern and it has a name: pathological accommodation.

It’s when being agreeable, flexible, and easy to work with becomes the default, even when it costs you time, energy, clarity, or self-respect.


You didn’t choose it.
You learned it.

This is how it works:

Over-accommodation is not about being nice. It’s about avoiding risk.

It’s about staying safe, staying liked, and staying employable in systems where people like you, maybe women, maybe first-gen professionals, maybe folks from marginalized backgrounds, have been taught that the fastest route to success is to take up less space.

So you over-function. You smile. You say yes when you mean maybe.
You answer emails with three paragraphs of context just to justify a boundary.
You write that Slack message six different ways so it doesn’t sound “harsh.”
You carry resentment but bury it under your “grateful to be here” face.

And when you’re honest, you don’t even know what you need anymore because you’ve been so focused on what everyone else needs from you.

This isn’t about weakness.

It’s about conditioning.
And it’s deep.

Many of us were raised to believe our value lies in being helpful, kind, agreeable. And in the workplace? That same behavior is rewarded. Until it isn’t.

Until you burn out.
Until you get passed over.
Until the weight of everyone else’s comfort sits squarely on your shoulders, and you realize—no one asked you to carry it. You just learned how.

So now what?

Reframe:
You’re not “too sensitive.” You’re perceptive. You’re not “too accommodating.” You’ve adapted to survive. That’s not failure, it’s skill. But you get to choose different now.

Rebuild:
Start small. Notice when you feel the urge to jump in and save, soften, or smooth things over.
Practice saying, “Let me think about it and get back to you.”
Let silence hang a second longer in a meeting before you fill it.
Be clear, not cushioned.

Rebound:
You don’t have to earn your place by being invisible.
You don’t have to trade authenticity for approval.
You don’t have to carry other people’s reactions as your responsibility.

A Question for You This Week:

What would it feel like to stop over-accommodating and start self-honoring, just a little more each day?

That’s the work we do at gumption: shedding the strategies that once kept you safe, and building the ones that will actually move you forward.

You don’t have to hustle for your worth. You already have it.

Just Added to the gumption. Library

I’ve added a fresh round of resources to the client library to support wherever you are in your search or career growth:

Quick-start LinkedIn tools and optimization guides
A Resume Quick Guide that walks you through my proven formula for success
Job search tracking tools to stay organized
Networking scripts and strategy guides to make outreach less awkward

gumption. clients can access the full library anytime:
👉 https://app.practice.do/library

All gumption. clients get free access to live webinars and events, too!

From the Road (and the Mountains)

I just got back from two weeks in upstate New York and Western Massachusetts within the Hudson Valley, Catskills, and the Berkshires, and it was one of the most restorative, awe-filled stretches of time I’ve had in years.

I hiked.
I kayaked.
I had some of the best food I’ve ever eaten (if you’re ever in the Hudson Valley, Mel the Baker in Hudson and Pinkertons in Kingston are a must. Both led by powerful, talented, brilliant James Beard Award winning women).

And somewhere between the trailheads, the laminated pastries, and the quiet, I found something that felt really important: space.

During my time away, I hosted a live Walk & Talk session with Chloe Nassau. It was one of the most grounding moments of the trip.


If you’re new to Walk & Talks, they’re 30-minute, live guided audio sessions designed to help you step away from your desk and back into your body. Each one follows a 3-2-1 rhythm (inspired by James Clear):

  • 3 ideas

  • 2 things to think about

  • 1 quote to carry with you


Chloe’s session wove together grief, transitions, and movement in a way that made the world feel a little more possible. I can’t wait to share future sessions with you.

What I Learned (or Remembered) While Away

Taking real time away isn’t easy when you run a business. Or when you’re the kind of person who holds a lot for other people. But here’s what became clear as the days slowed down:

1. Solo and semi-solo retreat time is deeply restorative.
Being alone (without being lonely) helps me hear myself again.

2. Outside of resume and LinkedIn work, the biggest investment in yourself right now is community and advocacy.
Who you’re surrounded by matters. And so does how you show up for them and let them show up for you. It’s really, really difficult to navigate all the moving pieces alone and not get stuck in your own head. Keep trusted advisors, coaches, peers, and mentors close.

3. You have to find your thing in this world, define it, and run with it.
For most of my life, I told myself I couldn’t be a writer. That writers were a specific type of person, someone with talents I didn’t have. They were “creative.” I was strategic and more literal.

But over the past year, I’ve started to let go of that story. I’ve realized I’m at my best when I’m writing, not just content or client work, but the messy, reflective, trying-to-make-sense-of-it kind of writing. So I gave myself permission to lean in during this trip.

I started framing chapters of the book I’ve wanted to write for years.
It’s nowhere near ready for other people’s eyes, and that’s okay.
The win was allowing myself to begin without needing it to be perfect.

So if you’re waiting for permission to do the thing you secretly want to do—
this is it. Start. Begin badly. Get curious. Get quiet. See what wants to come through.

You don’t need a perfect plan.
You need a little gumption.

And maybe a walk.

P.S. Want to join the next Walk & Talk? I’ll be adding more to the calendar soon!

A peaceful little pond behind my writer’s cottage in Tyringham, MA

My view from last week’s Walk and Talk with Chloe Nassau.

Inside Mel the Baker, which is assuredly the best bakery I’ve experienced… ever.

We fit it in a quick trip to Niagara Falls, which is essentially a shower on a boat with a view.

Don’t Be a Stranger!

Like my content?

Tired of always talking about how much you hate your job anytime you hang out with friends or family?

Think more people need to hear what I say?

5 Ways to Grow Our Networks:

1) Connect with me on LinkedIn!

2) Like, share, and engage with my content across social

3) Refer friends and co-workers to subscribe to Cup of Ambition!

4) Refer anyone who tells you they hate their job to me! Refer a new client, spin the prize wheel, and we both win!

5) Recommend me for speaking opportunities within professional networks, community groups, ERGs, workplace events, or other groups you’re a part of.

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