Hi, Realists! 👋

Welcome to Cup of Ambition, Volume 15.

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

‼️‼️  9-to-5 Dilemma: So… Tell Me About Yourself!

📖 Now Launching : Winter Realist Book Club

📌  Bad Bosses, Good Friends - Surviving Toxicity at Work.

🦁 Find Fulfillment Through Work Boundaries.

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

9-to-5 Dilemma.

“Generally, I feel prepared for interviews, but I bomb every time I get the ‘so tell me about yourself’ question at the start of an interview. It’s so vague and broad that I often end up rambling. I’m never sure how far back they want me to go, if they want me to talk about things that are already on my resume, or what else I should be telling them, so I just talk.

What is the best approach to this question? Why do interviewers ask it? Is there a secret I’m missing? Help me nail this so I can get past talking in circles.”

-Rambling Rose.

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

Why They Ask:

If you’ve met with me for an introductory call, you know this is the first question I ask new clients. I do this intentionally to get an initial sense of how well someone can clearly and concisely tell me about their wins and areas of power in their story.

I think of this as an icebreaker with a purpose. Interviewers are testing how well you can:

• Identify the most relevant parts of your background.

• Communicate your value clearly and succinctly.

• Set the stage for the rest of the interview.

This isn’t about you, it’s about you in this role.

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The Secret Formula:

When answering this question, stay laser-focused on relevance. Use this framework to craft your response:

1. Who Are You? (Present):
   Share your current role and a top accomplishment related to this job.

   
   Example: “I’m currently a Senior Marketing Manager leading a team of five, where I’ve developed campaigns that increased customer retention by more than 20% year-over-year.”

2. What Have You Done? (Past):
   Highlight key achievements that align with the skills or outcomes needed in this role.

   Example: “Before that, I worked in content strategy for the leading home goods manufacturer in the US, where I led a rebranding initiative that positioned my company as an industry leader.”

3. Why Are You Qualified? (Future):
   Tie your experience to this specific role and express your excitement about the opportunity.

   
   Example: “I’m looking to bring my expertise in strategic marketing to a company that values innovation, which is why I’m so excited about this opportunity.”

Keep it under two minutes, stay relevant, and emphasize the value you bring to this role.

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Pro Tip: Stay Focused.

Before your interview, review the job description and pick 2-3 themes the company values most. These could be leadership, innovation, client success, or technical expertise. Tailor your answer to highlight how your experience directly aligns with those themes.

Remember, the goal is not to share everything about yourself—it’s to give the interviewer a clear, concise picture of why you’re the right fit.

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Your Turn.

Take 10 minutes to craft your answer using the Who-What-Why framework. Practice until it feels polished but natural—because confidence is half the battle.

Feeling stuck? Let’s connect! I’d love to help you craft an answer that’s impossible to ignore.

Rooting for you,
Kelly

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Bad Bosses, Good Friends.

It’s ironic, isn’t it? Some of the strongest, most enduring friendships are born in the least ideal circumstances—like working for a bad boss or surviving a toxic workplace. If you’ve ever bonded with a coworker over whispered “Can you believe this?” conversations or shared sighs during impossible deadlines, you know exactly what I mean.

Workplace friendships formed under these conditions are unique. They’re built on shared resilience, a deep understanding of each other’s struggles, and often a healthy dose of humor to get through the chaos.

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The Impact of Workplace Friends

Some of the most important and painful moments in my life have been marked by the presence of incredible work friends:

• They’ve supported me through the loss of parents, personal struggles, and moments of overwhelming self-doubt.

• They’ve listened to stories I couldn’t share with anyone else at work, knowing the real “under the surface” version of my life.

• They’ve advocated for me when I couldn’t advocate for myself, and commiserated when the situation felt insurmountable.

Work friends often see us at our most vulnerable, exhausted, overwhelmed, and sometimes on the verge of giving up. And yet, those same moments can be the foundation of lifelong relationships.

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Who Has Influenced You?

Think about your own career. Who has been a workplace friend that truly influenced you? Maybe they were the person who always had your back during tough meetings, who encouraged you to pursue a new role, or who made you laugh until you cried on the worst days.

Take a minute this week to thank them. Send a message, schedule a coffee, or simply let them know how much they’ve meant to you. Celebrate your collective strength in surviving a bad boss—or any tough situation—together.

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Collective Strength.

A toxic workplace can take a toll, but the friendships forged in those trenches can last a lifetime. They remind us that even in the hardest times, we’re not alone. And sometimes, the silver lining of a bad boss is discovering that the best colleagues are also the best friends.

This week, take a moment to reflect on those connections. Celebrate the strength and resilience you’ve built together—and know that you’re stronger because of it.

Boundaries Fix Broken Relationships With Work.

Let’s be real: the next raise, promotion, or title won’t fix everything. It won’t magically make you feel more fulfilled or whole. And it certainly won’t define your worth.

You are already enough. You already bring incredible value to the table—right now, as you are.

Fulfillment With Boundaries.

Goals are healthy. Ambition is powerful. But without boundaries, they can also lead to burnout. The corporate world will always ask for more. More time, more effort, more of your energy—often without giving you the space to step back and ask:

• Who am I beyond my job?

• What do I bring that’s uniquely mine?

• What do I need to thrive—on my terms?

If you don’t get clear on those answers, the endless cycle of chasing “more” can leave you feeling like you’re never quite enough.

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The Truth About Success.

True fulfillment doesn’t come from adding another line to your resume. It comes from knowing your value and staying aligned with your own definition of success—not the one society, your boss, or even your LinkedIn feed tries to sell you.

So, take a moment to pause. Ask yourself:

• What do I already bring to the table?

• What are my non-negotiables for the next chapter of my career?

When you’re clear on who you are and what you bring, you set the terms. You decide how much of yourself to give—and where to draw the line.

🔥Ambition Accelerator 🔥

You are already enough. Your worth doesn’t hinge on your job title, productivity, or someone else’s approval. Goals are great—but they’re a tool, not a measure of your value.

Let this be the week you take back your power. Reflect on your strengths. Set boundaries. And decide what “enough” looks like for you.

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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