Welcome to Cup of Ambition! ☕️

9 to 5 Dilemma

“I know I’m not the only one struggling with this, but it feels like I’m a complete leper to companies.

Over the last five or so years, I’ve had multiple starts and stops. I worked in smaller companies and start-ups that hired me, reorganized me, and laid me off within 6 months. I kept taking roles like this because they were the only companies reaching out—and I needed to work.

Now my resume looks like I’m the problem. Companies see me as being a weak performer or as someone who quits, which I’m not. I’ve just had a series of bad luck.

What can I do to convince companies that I’m not the problem so they at least speak to me?”

-Short Stays & Long-term Problems.

Ideas & Best Practices for Short-Term Roles:

1. Use a one-line summary at the top of each short role

   This helps your reader understand why the role was short before they make assumptions.

   Example:

   People Operations Lead | Company ABC (Feb 2023 – June 2023)

   Hired to stabilize culture and internal systems after funding round; role eliminated in organizational restructure.
   

   No drama, no apology—just clarity.

2. Lead with outcomes, not timeframes
   Short tenure ≠ low impact. Show what you did while you were there.

   “Launched onboarding process that reduced new hire ramp-up time by 40% in under 90 days.”

   The goal: shift the focus from how long you were there to what you did while you were there.

3. Use your summary to own the narrative
   Right at the top of your resume, you get a few lines to set the tone. Use it.

   “Known for bringing calm to chaos. Hired by mission-driven startups to build structure, operational clarity, and people-first practices—often amid rapid change or restructuring.”

Why I Rebranded to gumption.
And what it means for you.

You may have known me as The Resume Realist—and if so, thank you. That brand helped me connect with hundreds of people navigating job transitions, self-doubt, career pivots, and moments that required big decisions and even bigger courage.

But as my clients’ needs grew, so did the work.

Clients weren’t just asking for resumes anymore. They were asking:
😕 How do I advocate for myself in this role?
🤔 How do I recover from burnout and get clear again?
🙂 What’s next for me—and how do I go after it?

Resumes weren’t enough.
So, I built something bigger.

🎊 Welcome to gumption. 🎊 

Boldness. Confidence. The courage to take action.

gumption. is a career coaching and transition support company that helps real people move forward with clarity, confidence, and strategy. Whether you're leaving a job, looking for one, or leveling up in the one you have, the tools and support we offer go way beyond documents.

We now support:

• Individuals navigating job searches, career pivots, and self-advocacy

• Organizations facing layoffs that want to protect their brand and take care of people

🤩 Come see what’s new: www.get-gumption.com

I’m so proud of this rebrand—not because it’s slick or shiny, but because it feels true. True to what this work is about. True to what I want to give to you. A huge thank you to the talented and brilliant Kendra Sanchez for bringing my vision to life.

Whether you’ve been following me for years or just stumbled into my inbox, you belong here.

Thanks for being part of the journey.

Now let’s put your gumption to work.

“You Just Don’t Stand Out”
Why working hard isn’t always enough—and what to do about it.

I was talking with a client last week and she said something that hit me in the gut.

We were unpacking a situation at her previous job. She had been working her ass off—cleaning up other people’s messes, saying yes to everything, picking up the slack no one else would. She was doing the work of people one, two, sometimes three levels above her. Not because she was chasing titles, but because she cared, and she’s wired to do great work.

Eventually, she went to her manager to ask about her growth and what her future might look like there, whether she was being considered for a promotion.

The feedback?
“You do great work, but you just don’t stand out.”
“You’re great, and we love having you on the team—but I don’t see you promoting anytime soon.”

She spiraled. And I get it.

“I’ve been working SO HARD for nothing.”
“I’m the glue. The go-to. The one they can count on.”
“How do I not stand out?”

Working hard is not the same as being visible.
And being helpful is not the same as being positioned for growth.

This isn’t about being louder. It’s not about chasing credit or being cutthroat either. It’s about self-advocacy.

When your manager doesn’t see you as ready to grow, it’s often not because you’re missing skill, it’s because you haven’t made the shift from execution to ownership.

🪴1. Self-advocacy is a daily practice, not a one-time ask.

You don’t have to wait for a performance review to start owning your narrative. Self- advocacy sounds like:

“Here’s the impact that project had.”

“I stepped in because I noticed this gap, and here’s how I solved it.”

“I’d love to take on a project that builds on what I’ve done in X area.”

🪴 2. Set the frame early.
The way you show up in onboarding and interviews sets the tone for how others see you. Don’t just talk about what you can do—talk about how you work, what you value, and the kind of impact you aim to have.

Own your strengths and how they connect to the business. Don’t leave it to someone else to figure it out.

🪴3. Being “the one who gets things done” is not the same as being “the one we can’t afford to lose.”
To be seen as a leader, you have to shift from doer to driver. That means sharing not just what you did—but how it moved the needle.

If You’ve Heard Something Like:

“You’re great, but…”
“You’re so reliable, we don’t want to lose you in your current role…”
“Everyone loves working with you, but promotion is competitive…”

That’s your signal.
It’s not that you’re not good enough.
It’s that you need to reclaim your voice—and your value.

You don’t need to become someone else to stand out.

You just need to show up with strategy—and start making your impact visible.

Let’s make that happen.

Upcoming Events & Learning Opportunities:

Join me for a FREE Webinar on April 9 at 11 am EST with Carol Essig.

👉 Learn More & Register Here: https://www.eventbrite.com/e/pivot-and-prosper-own-your-career-tickets-1292814566169?aff=oddtdtcreator

NYC Locals: Join me for an in-person event on April 24 at 9 am EST with Chloe Nassau.

👉 Learn More & Register Here: https://lu.ma/32t4rs1d

Dollyism