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☕️Cup of Ambition: When “Good at Everything” Feels Like Being Great at Nothing.

☕️Cup of Ambition: When “Good at Everything” Feels Like Being Great at Nothing.

Kelly Roehm
August 07, 2025

In This Edition…

9 to 5 Dilemma: For the Jack and Jills of All Trades.
Upcoming Events.
Why Your LinkedIn Announcement Got Zero Traction.
Dollyism.

9 - 5 Dilemma

”My career is a weird mix of everything… strategy, comms, ops, hiring, project management, leadership, culture-building… I’ve said yes to a lot over the years. When I was younger, all of my bosses told me to just say yes to new assignments and opportunities because it creates future capability. But now I’m 18 years into work and I have absolutely no idea how to talk about what I do.

I feel like if I leave anything out, I’m limiting myself. But if I try to carry all of it forward, I don’t sound like I’m good at any of it. I can talk about a lot of different things, but I’ve never been in any of them long-term.

When I apply for jobs, I notice that I have some of the qualifications, but not all of them, and I don’t have certifications in any of the requirements. I’m starting to think I did myself a disservice by saying yes so much along the way. It’s created this story that makes me feel chaotic and like I don’t even know what I’m good at.

How can I pull it all together and position it to employers without looking like a complete chaotic mess?”

-Jill of all Trades

This message is one of the most common narratives I hear in clients and I see in their resumes. It happens often with high achievers, contributors, and people pleasers… they say yes without strategy and end up feeling like a grab bag of skills with no consistent thread.

You’re a high-functioning overachiever who said yes to everything except editing.

This isn’t a problem of skill, you have plenty of skill and talent. You can do just about anything and be good at it, which is an asset.

But, it can create a problem of narrative clarity.

The Cost of a Lifetime of “Yes”

Saying yes early in your career builds experience.
Saying yes repeatedly, without pause or strategy, builds confusion and overwhelm long-term.

It makes your story wide but blurry.
You feel capable of almost anything, but confident in nothing.

Here’s what’s happening:

You’re carrying 18 years of experience without a filter
You’ve been told to “package it up,” but never taught how
You’re afraid that if you narrow the story, you’ll lose value

When you put all of that on paper, in your LinkedIn profile, and try to sell it all in an interview, you effectively sell nothing.

Your resume becomes under-optimized on skills, keywords, and competencies
Your LinkedIn profile feels like ping-pong with all the unique narratives bouncing around
Your interview sounds like a hodge podge, a journey around the world without detail or description.

It’s time to decide what you’re no longer willing to carry, what deserves space in your story, and where to strategically shine the spotlight.

What Clarity Actually Looks Like

Clarity doesn’t mean picking one skill and throwing everything else away. You worked hard for those achievements and skills, but they all don’t have equal weight and they all can’t be shoved into your brand and story.

Naming your throughline: What’s the pattern in what you’ve always been trusted with?
Choosing what to lead with: Not everything belongs in the headline.
Aligning your story to your goals: If you want a Chief of Staff role, your narrative needs to sound like one, even if your last title didn’t.

Clarity is when someone reads your resume or LinkedIn and thinks,

“Oh. I get what she does. And I know where she fits.”

You Can’t Move Forward Without Editing

We aren’t trying to minimize the scope of all of your accomplishments or box you in, but we do need to gain clarity in choosing what your next chapter is actually about.

Want to sound strategic, not chaotic?

Instead of saying, “I’ve done a little bit of everything. I’m always willing to take on anything new and do whatever it takes.”

Say, “Across all of my roles, I’ve always been the person who [core strength or theme]. Most recently in my role at Acme Corp, I use my strength in X to do Y.”

How to Start Finding Clarity

Here’s a practice I walk clients through all the time:

List five roles or projects you’ve said yes to.
Include the messy ones. The random ones. The ones that “don’t fit.”
Next to each one, write down two things:
→ What were you responsible for?
→ What impact did you have?
Now scan for patterns.
Are you always the person who makes things clearer?
Who gets buy-in across teams?
Who turns chaos into a plan?
Now ask yourself:
What do I want to carry forward?
What am I finally ready to leave behind?

Clarity is built in the edit, not the accumulation.

Final Thought

You are a whole person with a wide foundation built on being good at a lot of things. That’s a great problem to have! You know that regardless of what comes your way, you always figure it out and do it well.

That’s earned you the ability to decide what belongs in your next chapter. You’re in charge of the story you bring forward and what you are known for.

What part of your career are you still saying yes to, even though you’re no longer interested in being known for it? And what would become possible if you finally put that part down?

Got your own 9 to 5 dilemma?
If you’re wrestling with something at work—confusing feedback, job search drama, leadership challenges, or just trying to figure out what’s next—I want to hear it.
Send your dilemma by responding to this email and I might feature it (anonymously) in an upcoming edition.

Because if you’re feeling it, chances are someone else is too.

Upcoming Events & Trainings

August Walk & Talk : What Do You Wanna be Known For?

Thursday, August 21, 11:30 am - 12:00 pm EST

Free for Cup of Ambition readers & gumption. clients!

https://lu.ma/bbjz6sno

Move your body, clear your mind, and set your focus. This 30-minute Walk & Talk is built for clarity, connection, and intentional momentum.

Each session follows a simple structure inspired by James Clear’s 3-2-1 model:
3 prompts to reflect on
2 questions to answer
1 commitment to carry forward

Why do we walk while we talk?
Movement helps unlock new ideas, shake off pressure, and shift into a more creative, grounded mindset. Whether you're pacing your kitchen or walking your neighborhood, the goal is to step away from your desk and into a space where insight can meet action.

We’ll explore how your reputation is shaped and how to take more ownership over the story you're telling, at work and beyond.

No slides, no cameras, just space to think, reflect, and reset.

Join us for a little motion with your mindset.

The Problem with “I’m looking for work, let me know if you hear of anything”…

Your LinkedIn probably has quite a few “Open to Work” announcements these days.

And most of them probably sound pretty similar, maybe something like this:

“As you may have heard, I was part of the reorganization at Acme Corp. last month. I’m currently looking for a new role in Accounting and would appreciate any referrals you may have.”

And then the green banner comes up.

The problem with this strategy is that it’s vague. It puts the burden on the other person to figure out what you do, what you want, and how to help you. It doesn’t make it easy for anyone to help.

✅ What Your Post or Message Should Include

Element	Details + Example
Who you are	Start with clarity: industry, experience level, and your superpower. "I’m a people-first operations leader with 10+ years of experience scaling ERP systems, operations teams, and culture in early-stage start-up environments (Series A-C, 50-500 employees)."
What you’re looking for	Be direct about the type of role + focus area. "I’m exploring opportunities in Program Management, People Ops, or Chief of Staff roles, particularly at SaaS or Tech-Based start-ups navigating rapid growth."
Target industries or types of companies	Be industry- or environment-specific. "Ideally, I’d love to work in the education, healthtech, or social impact space—organizations that need documented operating procedures, scalable systems, and better alignment between people and process.”
Call to action (specific, not needy)	Say exactly what you want—introductions or convos with people in X roles. "If you’re a VP of People, COO, or someone hiring for these roles, or you know someone who is, I’d love to have a quick conversation."
Close with voice + warmth	Stay human. You’re not just making a request—you’re showing up. "Appreciate any connections or insights you’re open to sharing. Thanks for being part of my community."

❌ Don’t Say

Instead of this…	Say this…
“If you hear of anything, let me know”	“I’m specifically looking to connect with [decision-maker titles] at [company types].”
“Open to anything!”	“I’m targeting [job type] roles where I can contribute [your strengths].”
“Just putting it out there”	“If you know someone hiring for [role], I’d value a warm intro or 15-minute chat.”

Once you’ve narrowed down your ask to a clear, specific, and directed message, try formatting it so it stands out.

I like a 1-page format that blends a cover letter, sales sheet, and resume so your connections can get a quick hit view and potentially share it with their contacts.

Align it to your brand, your voice, and your vibe. You may prefer to keep it more streamlined, especially if your next move is in your industry or of a similar title. Just remember to lead with value, be specific, and give your audience a clear call to action.

You are a brand and when a brand relaunches, it needs a strategy. Use this relaunch as your first step in naming what is for you and why you’ll make an impact there once you get the right introduction.

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!

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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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