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- ☕ Cup of Ambition: The Job Market Doesn’t Play by the Rules— How to Win Anyway
☕ Cup of Ambition: The Job Market Doesn’t Play by the Rules— How to Win Anyway
Tips, tools, and real advice to help you land and survive your 9-to-5.
Kelly Roehm
March 06, 2025
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.
Hi, Realists! 👋
Welcome to Cup of Ambition, Volume 21.
In this edition, you’ll get the scoop on:
‼️‼️ 9-to-5 Dilemma: Optimized & Invisible.
📅 Mark Your Calendar: FREE Webinar - Resumes That WORK.
📌 Stop Crowdsourcing Resume Advice & Think Like a Founder.
😍 The Resume Realist Rebrand is COMING!
🔥 Ambition Accelerator (1 Quick Career Action to Take This Week).
9-to-5 Dilemma.
“I’m curious: if everyone subscribes to the ATS myth of crafting an impeccable resume with the “right” format and bullet count, tailoring their resume for every job, applying only to roles where they’re at least 80% qualified, building 500+ LinkedIn connections, and broadcasting their job search to every contact—what then is missing? I’m doing all the right things by the book and still getting nowhere.
With many candidates following these best practices, job postings become inundated with applicants, making it extremely challenging for recruiters to narrow the field. Are there other strategies we should be exploring to gain greater exposure and stand out from the competition?”
-Optimized and Still Ignored.
What’s your current 9-to-5 dilemma? Send your story to: [email protected]
You’re already ahead of the game, but this job market doesn’t play by the rules. Landing a job isn’t just about doing everything right, even though that used to work in a job search. Today’s job search is about being remembered.
When everyone is following the same process, the real differentiator is how you position yourself in the market before you ever hit “apply.”
Here’s what will set you apart:
✅ Engaging with the right content.
Instead of just scrolling, start strategically commenting on posts from industry leaders, hiring managers, and decision-makers at companies you’re interested in. Add value to conversations, share insights, and make yourself known in the right circles.
✅ Sharing your expertise consistently.
You don’t have to be an “influencer,” but sharing your thoughts on industry trends, leadership lessons, or even lessons learned from past roles builds credibility. Thought leadership—even in small doses—creates opportunities where recruiters and hiring managers come to you.
✅ Making small networking deposits—before you need them.
The best time to build relationships isn’t when you need a job—it’s long before that. Engage with past colleagues, send a quick note to someone whose work you admire, or offer a helpful introduction. Those small deposits add up, and when the time comes, you’ll already have a network that’s willing to advocate for you.
✅ Getting hyper-specific about what you want.
It’s hard for people to help if they don’t know exactly what you’re looking for. Be clear about the roles, industries, and types of companies you’re targeting so your network can connect you with the right opportunities.
✅ Being seen as a problem solver, not just an applicant.
Hiring managers don’t just want to know you can do the job—they want to see how you think. Sharing a quick case study, breaking down a challenge in your field, or even posting a thoughtful take on industry trends makes you more than just a resume.
At the end of the day, standing out isn’t just about applying—it’s about positioning. The more you show up in the right places, add value, and build relationships, the less you’ll have to fight through a sea of applicants—because opportunities will start coming to you.
So—what’s one small step you can take this week to get ahead of the competition?
Join Me for a FREE Webinar This Month!
Stop Crowdsourcing Resume Advice—Think Like a Founder With a Pitch Deck Instead
Everyone has an opinion on resumes. You’ve probably heard conflicting advice about formats, bullet points, colors, ATS compatibility, and the “right” way to get noticed. But let’s cut through the noise with one simple truth:
Your resume is a pitch deck.
A pitch deck sells value in exchange for investment. As a professional, you are selling your time, energy, talent, and expertise in exchange for a salary. When you view your resume through this lens, it becomes clear what matters—and what doesn’t.
What’s a Pitch Deck?
A pitch deck is a concise, high-impact presentation used by startups and businesses to secure funding. It doesn’t overload investors with every detail—it focuses on the most persuasive, high-value information that convinces them to invest.
A great pitch deck:
✅ Captures attention immediately
✅ Highlights the biggest wins upfront
✅ Focuses on key metrics and impact
✅ Tells a compelling, cohesive story
✅ Leaves the audience wanting to know more
Now, apply that thinking to your resume.
Your Resume = Your Career Pitch Deck
Your resume’s job isn’t to list everything you’ve done—it’s to sell your value. Here’s how to structure it like a pitch deck:
📌 Start with the hook.
Just like a pitch deck opens with a strong value proposition, your resume should start with a clear, compelling summary that immediately signals why you're the right person for the job. Think of this as your headline statement—the “why you” in one glance.
📌 Lead with impact.
In a pitch deck, investors see the strongest numbers first—so don’t bury your best results in a wall of text. Your biggest achievements should be front and center in each role. Instead of listing duties, highlight results, revenue impact, cost savings, efficiencies, or team success.
📌 Prioritize clarity over clutter.
Pitch decks don’t have endless slides of text because investors don’t have time for that. Your resume should be skimmable, structured, and easy to read. White space is your friend. So is intentional formatting that guides the reader’s eye to the most important takeaways.
📌 Tell a cohesive story.
A great pitch deck builds a narrative—so should your resume. Instead of listing disjointed tasks, make sure each role builds on the last, showing a clear evolution of skills, leadership, and impact.
📌 Every bullet should pass a test.
Before adding something to your resume, ask:
Does this highlight a key skill or experience relevant to my target role?
Does this add to my overall narrative, persuasion, or sell?
If this were in a pitch deck, would it make the final cut?
If the answer is no, cut it.
What to Cut: The Resume Noise Filter
If it doesn’t strengthen your pitch, remove it.
❌ Long-winded job descriptions that state the obvious
❌ Overcrowded bullet points that don’t highlight results
❌ Every job duty you’ve ever had instead of key impact points
❌ Outdated skills or experiences that aren’t relevant
❌ Sections that don’t add to your story (like that old internship from 10 years ago)
The Bottom Line: Sell, Don’t Just Tell
Your resume isn’t just a career history—it’s a sales document designed to get you to the next step: the interview. Like a great pitch deck, it should hook the reader, highlight your biggest wins, and leave them wanting to know more.
So before you stress over whether your resume “follows the rules,” ask yourself:
Would this convince someone to invest in me?
If not, refine, tighten, and focus on what truly sells you. The rest is just noise.
What’s Next?
Look at your resume through the pitch deck lens. What’s working as part of your sell and what’s just filler? If you’re not sure where to start, I’m here to help.
Let’s make your resume a pitch they can’t ignore.
The Rebrand is Coming at the End of March.
I’ve been working hard to imagine what the next evolution of The Resume Realist looks like. I’ve engaged the wonderful, brilliant, innovative support of Amy Scalia at Local Creator Studio and Kendra Sanchez.
We’ve finalized a new brand name… let’s just say it’s the perfect single word to describe:
Initiative and resourcefulness – The ability to take action, make decisions, and move forward with confidence, even in uncertain or challenging situations.
Courage and determination – A mix of boldness, resilience, and perseverance, often in the face of adversity.
Want a sneak peak into the new brand feel and design? Check out my Pinterest design board!
I can’t wait to share the new vision, direction, and vibe with you later this month. It’s going to be epic.
I’m Launching a New Product—And I Need Your Input!
I’m putting together a LinkedIn Bootcamp designed to help professionals like you break out of lurking mode, build visibility, and attract real opportunities.
But before I finalize everything, I want to make sure this program meets you exactly where you are.
🔍 What’s holding you back on LinkedIn?
💡 What would make it easier to build your personal brand?
🎯 What outcomes matter most to you—job offers, clients, speaking gigs?
I’ve put together a quick survey (seriously, it’s short!) to make sure this bootcamp delivers real impact.
If you’ve ever wanted to grow your LinkedIn presence but weren’t sure where to start, I’d love your insights.
Thank you! Your input means everything.
🔥Ambition Accelerator 🔥
Take Strategic Action in Your Job Search This Week
Job searching can feel overwhelming, but here’s a simple way to cut through the noise and find the right opportunities faster: Boolean search.
What is Boolean Search?
Boolean search helps you refine your job search using specific operators in Google (or job boards like LinkedIn and Indeed). Instead of scrolling endlessly through irrelevant postings, you can target exactly what you’re looking for.
How to Build Your Boolean Search for Google Jobs
Try this structure:
("Job Title 1" OR "Job Title 2") AND ("Industry" OR "Company") AND ("Remote" OR "Location") -Intern -Entry
✅ Use quotation marks (“ ”) to search for exact phrases
✅ Use OR to include multiple options
✅ Use AND to combine necessary terms
✅ Use minus (-) to exclude unwanted results
Example 1: Finding Remote Marketing Roles
("Marketing Manager" OR "Brand Strategist") AND ("Tech" OR "SaaS") AND "Remote" -Intern -Entry
🔍 This tells Google: Find me Marketing Manager or Brand Strategist jobs in Tech or SaaS that are remote. Don’t show internships or entry-level roles.
Where to Use Boolean Searches?
✅ Google Jobs → Just type your string into Google and click the “Jobs” tab
✅ LinkedIn → Use in the job search bar
✅ Indeed & Other Job Boards → Works in most platforms’ advanced search
Your Turn!
Craft your custom Boolean search string and start job hunting smarter, not harder.
Dollyism.
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?
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4) Refer anyone who tells you they hate their job to me! Refer a new client, spin the prize wheel, and we both win!
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