Hi, Realists! 👋

Welcome to Cup of Ambition, Volume 16.

In this edition, you’ll get the scoop on:

‼️‼️  9-to-5 Dilemma: New Year, Same Problems. How to Break the Cycle.

📖 Launch Your Inner Badass: Join the Winter Book Club & Save $25!

📌 2025 Goals: Eat the Frog & Tackle Your Goals.

😭 We Did It— 2024 Bronze Level Career Coach of the Year!

⭐ Audit Your Wins: Build a Stronger Career Story for 2025.

🔥 Ambition Accelerator (1 Quick Career Action to Take This Week).

9-to-5 Dilemma.

“Is it me, or has this year been exceptionally exhausting for other clients you work with too? I started the year with the goal of leaving my current employer because I just couldn’t take it anymore. Now it’s December, and I’m still in the same job, at the same company, making the same money, and I still feel absolutely miserable.

I’m carrying this massive guilt that I’m failing. I never thought I’d let myself settle, but I am stuck. I set a work related goal and it either gets shut down, blocked, or avoided, so I just put off applying to jobs or talking to my boss anymore. I keep my head down and just keep chugging along… still feeling the same way with an extra layer of guilt for now making a change.

All I can think is, “I should’ve done more this year.”

What advice would you give to those of us who feel like they’re never ready to move on, but feel so guilty for not moving on?”

-New Year, Same Problems.

What’s your current 9-to-5 dilemma? Send your story to: [email protected]

Celebrate the Wins—Big and Small

You may not have left your job, received a raise, or landed a promotion this year, but ask yourself:

• Did you maintain stability for yourself or your family?

• Did you keep things afloat at work, even when it felt impossible?

• Did you set boundaries, learn something new, or find small ways to take care of yourself?

• Did you make it to today?

Wins don’t always have to look like big, sweeping changes. Even surviving a tough year is a win worth celebrating. Progress starts with honoring what you did achieve—even if it’s simply enduring the challenges.

It’s easy to be hypercritical of yourself and get stuck in the should’ve and could’ve. Dwelling on the should’ve and could’ve only adds weight to the already heavy load you’re carrying. You’re not failing—you’re human. You’re navigating uncertainty, exhaustion, and the very real fear that change might not work out.

The should’ve and could’ve are just stories. They don’t define who you are or what you’re capable of. Instead of focusing on where you feel you fell short, think about one small, imperfect step you can take toward change. Update your resume. Have one honest conversation. Explore one opportunity.

It doesn’t have to be a sprint. One step at a time will prove to yourself that you can move forward.

If this resonates with you, hit reply and share what’s been on your mind. You don’t have to navigate this alone. Together, we can make next year the year you’ve been waiting for.

Rooting for you,

Kelly

🚨 Ready to Unleash Your Inner Badass? 🚨

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https://getreal.theresumerealist.com/products/likeable-badass-book-club-virtual

2025 is the Year We Eat the Frog.

Ever had a day, week, month, or year when you keep yourself busy, but that one big task looms over you? You find smaller things to do, convincing yourself that you’re “being productive,” but deep down, you know you’re avoiding the most important thing on your list.

It’s time to eat the frog.

What Does It Mean to Eat the Frog?

Your frog is the task you’re dreading—the thing that feels overwhelming, difficult, or even impossible. It’s often the most important task on your list, but also the one you’re most likely to procrastinate on.

By tackling that task first, you:

Free up mental energy instead of carrying dread all day.

Build momentum to take on everything else with confidence.

Make real progress toward your bigger goals.

When it comes to your career, the “frog” might be:

Giving yourself permission to move on.

Having a tough conversation with your boss about your workload.

Finally sitting down to update your resume or applying for a new role.

The longer you wait, the bigger the frog feels. But when you take action—even imperfect action—you break the cycle of avoidance and build momentum.

How to Eat Your Frog:

1. Identify Your Frog: What’s the one thing that would have the biggest impact if you tackled it today? Be honest—what are you avoiding?

2. Break It Into Small Bites: If the frog feels too big, break it down. You don’t have to finish the entire task today—just take the first step.

   • For example: “Update my resume” could become, “Spend 10 minutes listing my recent achievements.”

3. Do It First: Tackle your frog before diving into emails, meetings, or smaller tasks. Once it’s done, the rest of your day will feel lighter.

4. Celebrate After: Reward yourself for taking action—whether it’s a break, a cup of coffee, or a moment to appreciate the win.

What’s the frog you’ve been avoiding? Write it down. Then, schedule time (even 10 minutes) to tackle it first thing tomorrow.

Eating the frog isn’t about perfection—it’s about showing up, starting small, and building momentum toward what really matters.

The hardest part is getting started. But once you eat the frog, you’ll realize it wasn’t as bad as you thought—and you’ll have already won the day.

Over three years ago, I started this business with one simple thought: most career coaching and resume advice is insufferable. I believed there had to be a better way to empower people in their careers—and that belief sparked what has become the most rewarding journey of my life.

Since then, I’ve connected with over 700 people through events and networks, coached 350 incredible clients, and read more resumes than I can even count.

In all of this, I’ve never felt more assured that I’m on the right path.

Thank you for making my first full-time year a success.
Thank you for cheerleading for me when I needed it.
Thank you for reading this newsletter, engaging with my content, and sharing your stories of encouragement and success.

It’s because of you that this business has grown beyond what I could have imagined. Here’s to continuing this journey together—one step, one story, one win at a time.

Year End Wins + Impact Audit.

As you close out 2024, you may also be wrapping up a self-review for your performance management process at work. This is a perfect opportunity to maximize your time and results by capitalizing on the data and stories you’re pulling into your review. Why not repurpose them for resume bullets?

Here’s how to conduct your Year-End Impact Audit:

1. Take Inventory of Your 2024 Wins and Achievements

Reflect on the year and jot down key accomplishments, big or small. Think about how you:

• Solved complex problems or streamlined processes.

• Exceeded targets or metrics.

• Led or contributed to successful projects.

• Received praise or recognition for your work.

2. Document Them

Use tools like OneNote, a simple spreadsheet (Reply to this newsletter if you want a free download of my Wins + Impact Tracker!), or even a designated folder in your email inbox. The goal is to create a running list that’s easy to access and update. For example:

• Achievement: Increased customer retention by 10% through personalized engagement strategies.

• Impact: Generated $500K in additional revenue while improving client satisfaction scores by 15%.

Tip: Attach measurable results to each entry where possible.

3. Keep Supporting Materials

Save copies of performance reviews, positive feedback emails, awards, or recognition. These artifacts not only validate your wins but also serve as concrete evidence for future opportunities.

Why This Matters

All of this serves two critical purposes:

1. Keeps You Focused on Wins
   When you're in the trenches, it’s easy to dwell on setbacks. Taking stock of your achievements reinforces a positive mindset and reminds you of the value you bring to your role.

2. Writes Your Resume for You
   By staying proactive, you’re essentially creating a library of impact-driven bullets that can be seamlessly added to your resume or LinkedIn profile when the time comes.

Start 2025 Strong
Taking the time now to audit your impact will set the foundation for a clear and confident start to the new year. It not only strengthens your personal brand but also equips you to articulate your value—whether for a promotion, new role, or networking opportunity.

So, what are you waiting for? Grab that spreadsheet, start documenting, and step into 2025 ready to share the story of your success!

🔥Ambition Accelerator 🔥

Define Your Bold Move: Set one bold, measurable goal for 2025.

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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