The move you've been planning for two years is not going to plan itself. At some point, thinking about the leap and making the leap have to become two different things.

Three things to take from this issue:

Ambition isn't the sprint. It's the steady, intentional move toward the life you're actually building and the celebration of who you already are. That's just what gumption. is for!

The window did not close, it’s always open and ready for you, but you are shutting the laptop before anything can really happen.

Here's what I want to say to you with peace and love: you do not have a clarity problem, you have an action gap.

You've been marinating on this for two years. You know what you want. Your performance in your role exceeds the level.

You are already doing the same work, just with an invisible title and less money.

I think you have more of a starting gap… you’ve been trying to plan your way into a decision that can only be made by moving.

The Sunday ceiling-staring, the list-making, the job posting spiral isn’t preparation for the next thing, even though it feels like you’re taking your first step, it’s a never ending research loop.

The research loop sucks in many people who, with good intention, continue to “prepare” for the next thing before they actually do the next thing. They spend months and years researching what could be instead of reaching for what is. They discredit themselves and say they might fail if they leap.

It feels like progress because your brain is engaged, but nothing is actually moving. And nothing will move until you do something that counts as a real step, even a small one, even an imperfect one.

I'll tell you where my head goes when I think about this.

Didn’t expect that, did ya? Or, if you know me well, you know it was probably going to come back to one of my favorites.

For those of you who never caught the Ina Garten fever like I did I’ll fill you in.

Ina was a budget analyst at the Office of Management and Budget in Washington when she saw an ad for a specialty food store for sale in the Hamptons. She was so burnt out at work, she knew she could do more, but everywhere she turned she got hit with patriarchal bureaucracy that kept her from moving into the next step.

She had no culinary training, no retail experience, and not even a real plan…more like a “I’ll figure it out, but I know I can’t stay here” vibe. She did the math over a weekend, bought the store, never to return the land of budget analysis.

The rest, as they say, is history…

I joke that Ina is the president of my personal board of directors for gumption. I “appointed” her to my fictitious board because she looked at a life that was fine and decided fine wasn't the point. And then she moved.

And THAT is gumption.

A few things worth knowing:

1. You are not starting over, you’re starting from somewhere.

So often we throw everything out in the pursuit of something new, only to realize the new pursuit wasn’t really that different.

It’s kind of like that moment before you go on vacation and you’re thinking about what to pack and you know that NOTHING you have is worthy enough to make the cut because vacation requires a completely different wardrobe, but in reality the stuff in your closet is just fine for the occasion.

You’re starting with good bones and have experience influencing without authority, aligning work streams, and troubleshooting complex challenges on major company rollouts.

That is an extraordinarily transferable set of skills that you’ll use to solve the next layer of problems you want to solve.

The version of "bigger" that you're picturing is probably closer than you think not through a reinvention, but through intentional repositioning.

2. The plan does not need to be finished before you begin.

You don't need a five-year roadmap, more certifications, "an “ideal job market”, or extra time. And, don’t hate me, but unfortunately, I don’t think there’s another “ideal job market” coming anytime soon.

Nevertheless, we persist. We wade through the bullshit to get to the goal because we know we’re worthy of more.

Maybe it starts with one conversation with someone doing the work you want to do. One LinkedIn message. One coffee. One application. Whatever is within near reach, grab it.

3. "Ready" is not a feeling that arrives, it’s a decision you make.

I have never met a person who made a meaningful career move and felt completely ready before they made it. Readiness is built in motion and you can’t fully think and plan your way into it.

I know, that sounds like leadership coach jargon, but it’s kind of a reality, unfortunately.

Sometimes people call it “fake it til you make it” but that also feels phony to me. We’re not faking anything, but we are practicing and learning to build skill through experience and we’ve never fully arrived at the destination, but that’s the point.

Here's a starting sentence for when someone asks what you're looking for:

Start brainstorming the work you’re already doing that matches where you’re going.

That’s the data that starts to reposition your story for a new audience.

The window is still open, the weather is fine (well, all things considered!), you just have to stop closing the laptop before you even start.

How simple is that? 😉

For a long time, the only way to work with me was all-in with a full engagement, a defined scope, a start and an end date. That model works when people are in career crisis or job search, but it doesn't work for every season.

A different kind of career + work relationship that’s steady and consistent with both 1:1 coaching, group office hours, tools, resources, and guides, community events, and snail mail sent to your door quarterly.

We’ll tackle everything from a job search, to a promotion, to help with writing your annual review, or dealing with your difficult boss. Wherever you are in your experience or work life, there’s room for you here.

No generic advice, templated responses, or endless questions. You’ll get personalized support based on what you need.

The club launches in May, but the waitlist opens today.

Here's what being on the waitlist means:

If you've been reading Cup of Ambition or suffering at work and thinking "I really need to work with Kelly” this is how to get started!

Or if you’re a former client ready to work on a longer term plan, I can’t wait to hear from you!

Neha Ruch, founder of The Power Pause, writer, strategist put something in her feed last week that stopped me mid-scroll.

"Ambition is not the relentless push for more, higher, bigger — especially when it's misaligned with what you actually value right now. Ambition is the constant and deliberate aligning of your actions with the life you want to live."

This is a complete redefinition of a word that corporate culture has owned for too long.

The version of ambition you were sold is the one that says you should want more, move faster, outperform, and prove it constantly… and if you're tired, you're probably just not cut out for this.

🙄🙄🙄🙄🙄🙄🙄

That version is what makes a job search feel like a personal failure instead of a market condition.

That version is what has people convinced they need to sprint harder when what they actually need is to get clearer and move slower.

That version is what keeps you running in circles towards “whatever is next” and frustrated when nothing ever really comes.

The worst part of all of it is that you’re probably putting all of that into something you don’t even care that much or value. You’re just hustling in the name of ambition without a goal, intent, or alignment check.

You may not be able to control layoffs, a toxic boss, or the application to a company that never calls back.

You can control your clarity. Your language. Your strategy. The story you tell about who you are and what you bring.

That's the version of ambition that moves careers forward to reach new goals, not 24/7 hustle culture that we’ve all been told is ambition.

The reframe:

You control where, with what effort, and what desired outcomes.

That's the kind of ambition gumption. is built on.

PS- If you’re struggling with feeling like ambition has just kept you running in circles without a goal, reply to this email for a FREE copy of my Career Direction Workbook! It’s full of prompts and ideas to start to get your ambition back without the hustle culture.

Audit every resume bullet for the word "helped."

"Helped launch the new onboarding program."

"Helped the team hit their Q3 targets."

"Helped drive a 20% improvement in retention."

If you did the work, own the verb.

"Helped launch" becomes "Launched."

"Helped the team hit" becomes "Led the team to."

"Helped drive" becomes "Drove."

Read through your resume this week.

Anywhere you see "helped," decide: did you support this, or did you lead it? Use the verb that's actually true.

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