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- ☕ Cup of Ambition: They’re Not Smarter—They’re Just Louder: Speaking Up with Confidence
☕ Cup of Ambition: They’re Not Smarter—They’re Just Louder: Speaking Up with Confidence
Tips, tools, and real advice to help you land and survive your 9-to-5.
Kelly Roehm
February 20, 2025
Hi, Realists! 👋
Welcome to Cup of Ambition, Volume 20.
In this edition, you’ll get the scoop on:
‼️‼️ 9-to-5 Dilemma: They’re Not Smarter, They;re Louder.
📅 Mark Your Calendar: FREE Webinar - Building a UVP Too Good to Ignore!
📌 Mass Produced Resumes Won’t Get You Hired.
😍 Big News Coming… And I Need Your Ideas!
🔥 Ambition Accelerator (1 Quick Career Action to Take This Week).
9-to-5 Dilemma.
“Growing up, I was never the smartest person in the room. I hung out with the smart kids and watched them speak up with confidence, but I always knew I didn’t have enough knowledge to contribute. So, I became the peacemaker—the one who helped bring ideas together, celebrated others, and shared my best thoughts behind closed doors.
As an adult, I find myself stuck in the same pattern at work. I support my boss by sharing strategy, risks, and action plans privately, but in meetings, I hesitate. When I do speak up, I overanalyze it for days, convinced that people are judging me, even when colleagues reassure me that I was great.
How do people build confidence in speaking up when they never believe they have enough experience, knowledge, or expertise to do so?”
-Always on Mute.
What’s your current 9-to-5 dilemma? Send your story to: [email protected]
This dilemma is painfully familiar to so many people, especially those who are deeply thoughtful, analytical, and don’t believe in speaking just to be heard. The problem isn’t a lack of expertise, it’s a misplaced definition of what it means to have “enough” expertise to speak with confidence.
Confidence isn’t about knowing everything. It’s about trusting what you do know.
We all know the people who can walk into a meeting and speak with absolute confidence, whether or not they actually know what they’re talking about. And then there’s the rest of us—the ones who sit on great ideas but hesitate to speak up because we’re not 100% sure we have it all figured out.
If you’ve ever found yourself thinking, "I don’t have enough experience to contribute," or replaying something you said in a meeting for days after, you’re not alone.
And if you keep waiting to feel fully ready, fully qualified, and fully certain before you speak up, you’ll be waiting forever.
Why You’ll Never Feel “Ready”
The bar for "expertise" keeps moving. The more you learn, the more aware you become of what you don’t know. It’s called the Dunning-Kruger effect—people who know very little tend to overestimate their knowledge, while highly competent people underestimate themselves because they’re aware of the complexity of the topic.
In other words:
🔹 The fact that you worry about not knowing enough means you already have more knowledge than you think.
🔹 The people who seem the most confident often aren’t the smartest—they’re just less concerned with getting it exactly right.
If you only allow yourself to speak when you’re 100% sure, you’ll spend your career watching less-qualified people take the credit for ideas you could have shared.
How to Speak Up (Without the Mental Spiral Afterward)
If you struggle with self-doubt when speaking up, try these strategies:
1️⃣ Change the Goal: Aim for Contribution, Not Perfection
Instead of asking yourself, “Is this the smartest, most bulletproof idea?” shift the question to:
✔ “Does this add something useful to the conversation?”
✔ “Would I say this in a 1:1 conversation? If so, why not in a group?”
Your ideas don’t have to be groundbreaking—they just have to move the conversation forward.
2️⃣ Speak Earlier in Meetings
The longer you wait, the harder it becomes. Make a small contribution early—agree with a point, ask a question, add a quick observation. This lowers the mental barrier and keeps you from overthinking later.
3️⃣ Get Comfortable with "I Don’t Know"
You don’t need all the answers. Some of the most respected people in the room confidently say:
✔ “That’s an interesting point—I’d love to explore that further.”
✔ “Here’s what I do know, and I’d be curious to hear your thoughts on it.”
Authority isn’t about having all the answers—it’s about owning what you do know and engaging in the conversation.
4️⃣ Stop Asking for Reassurance After Every Meeting
Texting coworkers with, “Did I sound dumb?” is keeping you stuck. Instead, ask:
✔ “What landed well in what I shared?”
✔ “Anything I could improve next time?”
This shifts your focus from fear of judgment to actual growth.
The Real Confidence Shift
Confidence isn’t something you either have or don’t have—it’s a skill. And the only way to build that skill is to start speaking before you feel fully ready.
The people in the room who sound so self-assured? They’ve just learned to trust that what they know is enough.
And it’s time for you to do the same.
FREE Webinar on February 27 at 12:00 pm EST
Your career is a strategic marketing campaign.
Your resume, your LinkedIn, and your interviews aren’t just check-the-box items—they’re how you sell your unique value to the right audience. And let’s be real, if you’re blending in, you’re losing out.
Join me for a free webinar where I’ll walk you through how to:
✅ Define what makes you uniquely valuable—and how to communicate it
✅ Craft a UVP that goes beyond “I help statements” and makes hiring managers take notice
✅ Position yourself for the roles and spaces that value what you bring
🚩 The Truth About “Top Resume Firms” (And Why Big Names Aren’t Always Better)
You’ve seen the claims: “#1 Resume Writing Company in the U.S.”
“Guaranteed to Land You a Job.”
“Resumes Written by Experts.”
Sounds great until you get the final product.
The reality? Big resume firms often overpromise and underdeliver, relying on generic templates, surface-level edits, and zero strategy. If you’re serious about your next career move, a mass-produced resume won’t get you there.
This isn’t a self-promoting piece, it’s information to help you shape the best decision and investment. I believe everyone should invest in their career strategy at least once in their journey, and when you do make that investment, it should provide a significant return on your investment.
🚨 The Problem With Large Resume Firms
1️⃣ Generic Templates That Strip Away Your Unique Value
I recently reviewed a resume from the“#1 Resume Writing Company in the U.S.” It was… underwhelming.
🚫 Overused buzzwords like “dynamic” and “proven track record.”
🚫 No storytelling or leadership impact.
🚫 A format crammed with text, forcing hiring managers to hunt for the important details. Seriously, SO MUCH text! Paragraphs of text!
🔹 Instead of highlighting measurable results, they used vague HR jargon.
🔹 Instead of showcasing leadership, they listed job duties anyone in that role could claim.
🔹 Instead of personalizing it, they delivered the same cookie-cutter format they use for every client in this industry.
💡 What’s Missing? A great resume should demonstrate leadership, strategic contributions, and quantifiable achievements that show why you’re the right fit for the next role. There’s no clear, unique value proposition here.
2️⃣ No Personalization or Strategy
Large firms focus on volume over quality. That means:
🚫 They don’t take time to understand your career trajectory.
🚫 They use AI-generated templates that fail to showcase your unique strengths.
🚫 They don’t align your resume with your target roles.
A resume isn’t just a recap—it’s a marketing document that should position you for where you want to go.
✅ A real resume strategist will ask in-depth questions, uncover your key wins, and build a career narrative that makes hiring managers see you as the right candidate—not just another applicant.
3️⃣ No Ongoing Career Support
A resume alone doesn’t land you the job.
But big firms send you a PDF and disappear—leaving you without support when you:
❌ Need to tweak your resume for a specific role.
❌ Are getting interviews but not offers.
❌ Realize your LinkedIn profile doesn’t match your resume strategy.
A strong career move requires more than a resume. It should be part of a full career strategy that includes:
✔ Resume optimization tailored to your next role.
✔ LinkedIn branding & networking strategies.
✔ Interview prep & salary negotiation coaching.
Without this full-picture approach, you’re left with a resume that looks “fine” but doesn’t actually help you get hired.
🔍 What to Look for in a Resume Writer or Career Strategist
So if big firms aren’t the answer—what is? Find someone who takes a strategic, high-touch approach to your career.
✅ They ask the right questions. A great resume writer digs deep into your accomplishments, leadership impact, and future goals. If they don’t ask detailed questions, they can’t create a compelling resume.
✅ They understand your industry. Different industries require different resume strategies—a strong HR resume doesn’t look the same as one for fintech, tech sales, or consulting.
✅ They offer coaching, not just a document. Your career is more than a piece of paper—you need someone who can guide your job search, strengthen your LinkedIn presence, and prepare you for interviews.
✅ They focus on quality, not volume. If a company is churning out 50+ resumes a week, they’re not giving you the strategy and attention you need. Boutique firms that prioritize individualized strategy will always deliver better results.
💡 The Bottom Line: Invest in Strategy, Not Just a Resume
A resume is only as valuable as the strategy behind it. If it doesn’t clearly showcase your leadership, impact, and key results, it won’t stand out—no matter how well-formatted it is.
Instead of wasting money on a high-volume resume factory, invest in:
✔ A customized, strategy-first resume.
✔ LinkedIn & networking guidance.
✔ Interview prep & career positioning.
Big Changes Coming… And I Want Your Input!
I’ve been thinking a lot about what job searching, career strategy, and self-advocacy actually mean, and how my business should reflect that.
The truth is, I’ve outgrown my brand name that focuses on the resume. What I do goes beyond documents. It’s about strategy, positioning, confidence-building, and helping ambitious professionals step into the roles they actually want.
That’s why I’m working on a brand refresh—one that better represents what we do here. And I’d love your thoughts!
What do you think this space should be called? If you have an idea, a gut instinct, or even just a word that comes to mind when you think of my work—hit reply!
And as a thank you… FREE SWAG!
In the meantime, I need to clear the brand shelf to make way for the next chapter—so if you send me your idea, I’ll send you some Resume Realist swag straight to your door. Think T-shirts, coasters, stickers—because who doesn’t love free stuff?
Can’t wait to share more soon. Stay tuned.
🔥Ambition Accelerator 🔥
Take Strategic Action in Your Job Search This Week
Hiring managers and recruiters see tons of resumes daily. If yours is named “Resumev87_FINAL_FINAL.pdf,” you’re already making their job harder.
Your resume file name is part of your brand. It’s a small but powerful way to signal professionalism, organization, and attention to detail.
🔹 DO: FirstName_LastName_Resume.pdf
🔹 DON’T: Updated_Resume_(UseThisOne).pdf
Why does it matter?
✅ It looks polished when uploaded to an ATS or emailed to a hiring manager.
✅ It’s easy to find if a recruiter downloads multiple resumes.
✅ It reinforces your name in case they need to search for it later.
💡 Pro Tip: If you’re applying for multiple types of roles, tweak your file name slightly:
✔ FirstName_LastName_MarketingResume.pdf
✔ FirstName_LastName_ProjectManager.pdf
Dollyism.
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