Hi Realists! 👋

Welcome to Cup of Ambition, Volume 9!

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

‼️‼️ 9-to-5 Dilemma: Beyond Burnout + Chasing Perfection.

💗 How Does Your Company View Your Family + Friends?

🍨 Branding Matters- The $347MM Halo Top Lesson.

9-to-5 Dilemma.

“I think I have gone past the point of burn out to a place where I don’t even recognize myself. I’m working 8-12 hour days and even when I’m not at work, I’m thinking about work… running through my to-do list, worrying about a presentation, remembering that I didn’t email someone back.

I guess maybe I need better boundaries, but I feel actual guilt when I let someone down. I feel sick if I don’t give 110%, but I still question if I’m even doing good work. I want to be the best at what I do, but the work just keeps piling on and it feels like an impossible task to do anything right.

I can’t sustain another 15-20 years at this pace. Should I look for another job? Will I just fall into the same trap again?”

-Overworked + Over It.

_____________________________________________________

Dear Overworked + Over It,

You’re a high achiever. You’ve always done great work. And you’re the team member that takes it all on while others clock out.

When those things are true, sometimes it means that you’ve learned to connect how you feel about yourself to how you’re performing at work.

Even when you’re trying to relax, you’re filled with the fear of failure because it doesn’t feel “safe” to disconnect, put work aside, and forget about it.

But here’s the truth: Your worth isn’t measured by your to-do list, or by whether you give 110% every single day. Until you discover a new safe space, one where can have some balance WITH your success, you’ll always be ‘on’ even when you’re off.

This is a common challenge among high achievers and is often referred to as performance-based self-esteem. According to psychologist Dr. Heidi Grant, this mindset creates harmful cycle where you feel like you must constantly prove your value through external validation, often at the expense of your mental health and personal well-being.

The difficulty in setting boundaries, feeling guilty for taking breaks, and questioning whether you’re doing “enough” stems from this inner drive to be perfect at work.

I’m trained in Dare to Lead by Brené Brown, a well-known researcher on vulnerability and shame. From the minute I read Dare to Lead, it changed my perspective on my own relationship with external validation, perfectionism, and chasing gold stars. Brene’s work is rooted in the idea that perfectionism is often driven by the fear of not being enough. We tie our achievements to our sense of self-worth, and as a result, we struggle to let go of work—even when we know we need to.

But here’s the truth: your worth isn’t measured by your to-do list, or by whether you give 110% every single day. Success shouldn’t come at the cost of your well-being.

Separate who you are from what you do.

How to Break the Cycle:

1. Redefine Success and Worth
   Start by redefining what success means to you—outside of your job. Success could mean showing up for your family, investing in your personal growth, or simply finding joy in your hobbies. Remember that you are worthy regardless of your professional performance. Positive psychology suggests that those who embrace a more holistic view of success (one that includes personal and relational well-being) tend to experience more fulfillment and balance in life.

2. Set Clear Boundaries with Your Time
   If you find yourself constantly working or thinking about work, it may be time to build more intentional boundaries. High achievers like you can reclaim your time by setting clear boundaries with yourself and others. Start by blocking off “no work” time during your day—whether it's taking a real lunch break or committing to a no-email rule after 6 pm. Protecting your personal time will help train your brain to disconnect from the demands of work.

3. Create a Post-Work Routine
   Cognitive behavioral therapists often recommend creating a transition routine after work that signals the end of the workday to your brain. Whether it’s going for a walk, exercising, or even just changing clothes, creating a mental and physical separation between work and personal time can reduce the habit of constantly checking emails or mentally replaying the day.

4. Challenge the Guilt
   It’s normal to feel guilty when you try to set boundaries—especially if you’re used to always going above and beyond. But ask yourself: Is the guilt coming from a fear of being seen as less capable or less valuable? High performers often feel compelled to meet unattainable standards and fear disappointing others. Try challenging this guilt by recognizing that rest and balance will actually improve your performance over time, not diminish it.

5. Develop a Growth Mindset
   Instead of measuring your worth by what you’ve achieved, focus on adopting a growth mindset. A growth mindset encourages you to see failures and challenges as opportunities for learning rather than signs of inadequacy. Shifting your mindset from “I have to be perfect” to “I’m always learning” can reduce some of the pressure to be “on” all the time.

6. Consider a Role Change with Intentionality
   Before jumping into another role or job, take time to reflect on your work patterns and consider what needs to change to avoid falling into the same trap again. Many people think a new job will solve their burnout, but the root causes—like not setting boundaries or tying self-worth to productivity—tend to follow them unless addressed. Ask yourself what you need from your next role: Is it more flexibility? A team with stronger support systems? Or is it a shift in the kind of work you want to do?

Remember: Success doesn’t mean burning yourself out. You deserve to find balance—both in your career and in your life. Until you create a new space where you can thrive with balance, you’ll always be “on” even when you’re off. Take small steps today to prioritize your well-being, and you’ll see that success doesn’t have to come at the cost of your peace.

Break Up With Brag Shame.

Join me next month on September 25 at 1 pm EST for a free event, “From 9 to Thrive: Transforming Ambition Into Achievement” hosted by TroopHR. I’ll be sharing research, tools, and tips to boost your skill in self-advocacy and ditch brag shame for good.

How Does Your Company View Your Life and Family: Asset or Liability?

One of my firmest beliefs in life is the importance of making active choices. Whether it’s choosing your partner, friends, or workplace, I believe that you should always try to choose wisely. Why? Because these choices shape so much of who you are and who you become.

In many ways, choosing your employer is very similar to choosing a life partner. You want both to see the best version of yourself—the potential that lies ahead—but also to embrace the current you, with all your complexities, quirks, and, yes, your personal life. The entire complex package of you.

Prior to starting my business, I spent a lot of time reflecting on what kind of employer I could imagine working for. Two things were non-negotiable for me: the opportunity to explore and develop my leadership skills, and the ability to balance my work life with my personal life. In my case, that meant balancing work with traveling, enjoying my evenings and weekends, and having autonomy over my schedule.

When I did find that next role, it scared the hell outta me! But it turned out to be one of the coolest challenges of my career, and for one very big reason—my employer didn’t just tolerate my personal life, they embraced it. Let me give you a few examples of how they supported me.

The Lesson: Employers That See the Whole You.

Your company should offer the flexibility to do a great job while honoring your personal life. They should see you, the full version of you, as a whole person—not just as an employee. They understand that being a mom isn’t a liability, but a strength. They acknowledge that we’re all multitasking partners, friends, families, responsibilities, grief, celebration, and all the other things that come from being human.

And here’s the takeaway: You deserve to find an employer that sees your full potential, while accepting your personal life as part of the deal. An employer that respects the complex, multi-faceted person you are—and realizes that by supporting that person, they’ll get the best work out of you.

So, ask yourself:

• Does your company value your time outside of work?

• Do they see your family and personal commitments as part of the unique strengths you bring?

• Or do they treat your personal life as a liability—something to work around or ignore?

Make Active Choices in Your Career

You always have a choice. Just like you wouldn’t settle for a partner who only sees you for who you might become, you shouldn’t settle for an employer who only values the “work” version of you. Choose a company that appreciates the whole package: your talent, your personal life, your quirks, your strengths, and your future potential.

Cincinnati Realists: Wanna Network?

Looking to enrich your life both personally and professionally? Mark your calendar for Sunday, Oct. 6, when the Empower Herr: Women's Health and Business Expo takes over the 21c Museum Hotel in Cincinnati. From 10 a.m. to 2 p.m., this free event offers a dynamic mix of fun, fashion, and female empowerment, and it's designed to connect and uplift women across the community.

Branding Matters: The Halo Top Story.

We all know that how something is packaged, presented, and marketed can be the difference between being ignored and being a breakout success. Take Halo Top, for example. When the company first launched, they were ignored and dismissed by many in the ice cream industry. It wasn’t because the product wasn’t great—it was. But their branding didn’t resonate, and that made all the difference.

It wasn’t until Halo Top rebranded, focusing on the story they wanted to tell—a low-calorie, high-protein ice cream that was actually delicious—that people started paying attention. By packaging their message more effectively, they tapped into a market that craved indulgence without guilt. That shift in branding wasn’t just a makeover. It completely changed the trajectory of the company, ultimately leading to their valuation at $347 million.

The lesson? Your story and how it’s packaged matters just as much as the product itself. And when it comes to your career, you are the product.

Your Brand is the Thread That Makes Your Story Uniquely Yours

The same principles that applied to Halo Top can be applied to your career. Your brand is the thread that weaves through your entire story, tying together your skills, experience, and unique strengths. It’s the foundation of how others perceive you—whether they’re potential employers, colleagues, or clients. And it’s not just about your LinkedIn profile or resume—it’s about how you show up in the world, both personally and professionally.

If you don’t craft your brand intentionally, you risk being overlooked or misunderstood, just like Halo Top before they found the right story to tell. But when your brand is aligned with who you truly are and the impact you create, you become memorable, valuable, and irresistible to your target audience.

Market Yourself Like a Top-Selling Product

Think of your career as a product that needs to be marketed. The most successful products are clear about:

• What makes them unique

• Who they’re for

• What value they bring to their target audience

Your career should follow the same model. Whether you’re a seasoned professional, a solopreneur, or someone still exploring your next move, branding allows you to package your skills and experience in a way that resonates with the people and opportunities you want to attract.

So, ask yourself:

• What makes you uniquely you? What skills, traits, or experiences set you apart from others in your field?

• What value do you bring? How do you generate impact, solve problems, or contribute to your team or industry?

• Who is your target persona? Whether it’s future employers or clients, what do they care about, and how does your story align with their needs?

Your Brand Drives Your Success

Just like with Halo Top, the key to standing out and thriving in your career is to ensure your story is packaged in a way that captures attention and leaves a lasting impression. Your brand is the bridge between your past achievements and the opportunities waiting for you in the future. It’s what makes you, you.

Take control of your narrative. Craft your brand with intention, clarity, and confidence, and market yourself like the top-selling product you are.

Dollyism.

Don’t Be a Stranger!

Like my content?

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