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- ☕ Cup of Ambition: Quitters Can Win.
☕ Cup of Ambition: Quitters Can Win.
Tips, tools, and real advice to help you land and survive your 9-to-5.
Kelly Roehm
March 20, 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 23.
In this edition, you’ll get the scoop on:
‼️‼️ 9-to-5 Dilemma: Wasting Time in Workday.
📌 Quitters Can Win, Too.
😍 The Resume Realist Rebrand is HERE!
🤔 I Have No Thoughts? Tips to Write on LinkedIn Anyways.
🔥 Ambition Accelerator (1 Quick Career Action to Take This Week).
9-to-5 Dilemma.
“As I prepare for a more aggressive job hunt, I have a burning question: How much of an application needs to be completed? I always attach my resume, but many applications pull resume information into the form, often jumbled, requiring me to retype it. If there's an option to skip entering the details, is it acceptable as long as you have a resume to attach? Or is it better to take the time to copy/paste, especially for applications that also ask for a LinkedIn profile? How are recruiters really scanning candidate information, and which source do they prioritize?”
-Wasting Time in Workday.
What’s your current 9-to-5 dilemma? Send your story to: [email protected]
Let’s be honest—online job applications can be ridiculously time-consuming. Some systems make it easy: upload your resume, hit submit, done. But others (looking at you, Workday) demand that you manually enter every job, responsibility, and date like it’s 1999.
So how much of this actually matters? Let’s break it down.
The short answer: If you can attach your resume and submit without retyping everything, that’s usually fine. But it depends on how the company’s system processes applications.
Here’s how to know when to skip the extra work and when to take the time to fill everything out.
How Parsing Works in Applicant Tracking Systems (ATS)
When you upload your resume, many ATS automatically parse (extract) your details into the application form. Some systems do this well, while others distort formatting or leave fields blank.
💡 If the ATS parses your resume correctly and fills in the application, you usually don’t need to retype everything.
But if key details are missing or incorrect—especially job titles, dates, or contact information—it’s worth fixing those fields before submitting.
What Recruiters Actually Use
Most of the time, the form itself doesn’t matter much. As a recruiter, I rarely looked at system-generated application details outside of screener questions like:
✅ Are you legally authorized to work in the U.S.?
✅ Do you require visa sponsorship?
✅ Do you meet the minimum requirements for the role?
Everything else? I went straight to the resume. So did hiring managers.
When You Can Skip Typing Everything Out:
✔ The system correctly pulls your resume info into the form. If everything looks accurate, you don’t need to re-enter details.
✔ The application lets you attach a resume without requiring manual entry. Some systems rely entirely on the uploaded document.
✔ Applying via LinkedIn? If your LinkedIn profile is strong and the application allows submission through LinkedIn, that’s often enough.
✔ Minor formatting issues in autofill? No problem. Slight misalignment won’t hurt your chances, but check for critical errors.
When You Should Take the Time to Fill It Out:
⚡ If the ATS doesn’t parse key areas of your resume well. If dates, job titles, or descriptions are missing or incorrect, fix them before submitting. These areas are high priority for correction, as they may influence weighting or ranking within the system.
How Recruiters Actually Review Applications:
1️⃣ ATS Parsing & Screening – If your resume has the right keywords and structure, it moves forward.
2️⃣ Recruiter Review – Most recruiters look at your resume first, then LinkedIn, then the form if needed.
3️⃣ Hiring Manager Review – At this stage, your resume and LinkedIn presence matter most, not the form.
Bottom Line:
✅ If your resume parses well and autofills the form, submit and move on.
✅ If key info is missing or incorrect, update it before submitting.
✅ If it’s a job you’re highly interested in, take the time to ensure everything aligns.
Your goal? Make it easy for the system and the recruiter to see why you’re a strong fit—without spending unnecessary time on redundant fields.
Sometimes, Quitting Is the Smartest Move
We love a good “never quit” story. The grind, the grit, the late nights chasing a dream. But here’s the thing—sometimes, you gotta quit.
Not because you’re weak. Not because you’re failing. But because you’re making a smart, intentional choice about where to put your energy.
Maybe the job isn’t what you thought it was.
Maybe the industry no longer excites you.
Maybe the goal you set five years ago doesn’t align with who you are today.
That’s not giving up. That’s growth.
The key is knowing the difference between quitting on the thing and quitting on yourself.
🚫 Quitting on yourself sounds like:
“I’ll never be good enough.”
“I should just settle.”
“There’s no point in trying.”
✅ Quitting the thing sounds like:
“This isn’t the right fit for me.”
“I want something different.”
“I’m choosing to put my energy somewhere else.”
You are allowed to pivot. To change your mind. To walk away from what no longer serves you. The only thing that matters is what you do next.
So if you need permission to quit? Here it is.
Just don’t quit on yourself.
Big News: We’ve Got a New Name.
If you’ve been around for a while, you know my work has never been just about resumes. A solid resume is important, but real career success comes from something deeper—clarity, strategy, and the guts to go after what you actually want.
So it’s time for a name that reflects that.
The Resume Realist is now gumption.
Why gumption?
Because it’s what gets you unstuck. It’s the mix of boldness, confidence, and action that moves your career forward. It’s also what I help my clients tap into—whether they’re job searching, stepping into leadership, or navigating big career decisions.
What’s changing?
Not much, except I’m making it clearer that this work goes beyond resumes. I’m here to help people show up with confidence, stand out with purpose, and step into what’s next. Whether that’s through career coaching, leadership development, modern job search strategies, or working with companies that want to do right by their people.
Over the next month, you’ll start to see the new logo, website, and branding rollout!
What’s next for you? Let’s talk. Book a free call.
Join me at the 2025 Power to Pursue Event on May 16 at Music Hall in Cincinnati! I’m hosting a VIP table and would love to hold a seat for you.
I’m giving away TWO seats to the event with an invitation to an after hours happy hour with me and our table attendees!
Interested? Visit this LinkedIn post, like and comment! I’ll be selecting two commenters to join.
Who Should You Be Speaking to on LinkedIn?
Right now, recruiters, hiring managers, and decision-makers aren’t just looking at resumes—they’re looking at LinkedIn.
📌 Active profiles get seen first. The LinkedIn algorithm favors people who engage. More activity = more visibility.
📌 Opportunities come to those who show up. Commenting, posting, and networking puts you on the radar for recruiters and industry leaders.
📌 Hiring has changed. Many roles aren’t posted publicly. Instead, companies are sourcing talent through connections, referrals, and online presence.
If you’re waiting for the perfect moment to start engaging, stop waiting. Start commenting. Start posting. Start showing up. The more visible you are, the more opportunities will come your way.
A lot of people overthink their LinkedIn content and it stops them from even showing uo and engaging. Who am I writing for? What should I say? Will anyone even care?
Here’s the easiest way to answer that: Write to two versions of yourself—the you from 5-10 years ago and the you 5-10 years from now.
The You from 5-10 Years Ago
Think back to the version of you who was figuring things out, hitting roadblocks, or feeling stuck. What advice do you wish you had? What would have made your career path easier?
💡 Post ideas:
The career advice you wish you had
A lesson you learned the hard way
The thing you thought mattered (but didn’t)
How you overcame a challenge that felt impossible at the time
This content helps people who are where you once were—and those are often the people who need to hear your insights the most.
The You 5-10 Years from Now
Now, look ahead. Who do you want to be in 5-10 years? What kind of leader, expert, or creator are you becoming? The content you write today is a direct line to future peers, mentors, and opportunities in that space.
💡 Post ideas:
Topics you want to be known for
The trends or industry shifts you’re watching
The leadership qualities you’re developing
A question that sparks discussion with people ahead of you
By speaking to your past self, you bring value to those who are where you used to be. By speaking to your future self, you set yourself up for the next level of your career.
💬 Try this:
Before you write your next post, ask:
👉 Would this have helped me 5 years ago?
👉 Would this help me connect with the people I want to know in 5 years?
That’s your content strategy. Start posting.
🔥Ambition Accelerator 🔥
Take Strategic Action in Your Job Search This Week
Visibility = Opportunity. The easiest way to get noticed on LinkedIn? Commenting.
🔹 Engage Meaningfully – Skip “Great post!” and add a quick insight or question. Comments with 10+ words have 2X more impact than those with less than 10 words!
🔹 Be Strategic – Comment on posts from industry leaders, hiring managers, and peers.
🔹 Stay Consistent – Aim for 3-5 thoughtful comments this week. Commenting on 10-20 accounts per week leads to a average 50% increase in profile views.
Your Challenge: Find one post today and drop a meaningful comment. Then do it again tomorrow. Small actions → Big results.
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?
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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