Welcome to Secure the Damn Job, a special series on Five with Fry where I break down what actually works when you're applying for jobs. Sponsored by Hyreable (the career development wing of JenFryTalks), this three-part series covers cover letters, resumes, and interviews with real talk, real strategy, and zero fluff. Whether you're making a career move or entering the workforce, I’m here to help you show up strong and get hired.

Let’s talk about cover letters. Everyone loves to hate them, but when done right, they can open serious doors. In this first episode, I’m walking you through five essential strategies to craft a cover letter that actually gets noticed. From formatting musts like 0.4" top margins and no fonts smaller than 11.5, to what actually belongs in each paragraph, I’m giving you everything you need to make your letter clean, clear, and compelling.

We’ll talk about why your cover letter should mirror your resume (yep, I said it), how to highlight your strengths with a sharp four-paragraph structure, and why getting to the point is your new best friend. Whether you're actively job hunting or just refreshing your materials, these tips will change how you approach every application you send.

Need some extra help with your resume, cover letter, or interview prep? Head over to Hyreable to work with me directly—and let’s secure the damn job.

How to Handle the Emotional Side of Entrepreneurship (and Why Community Matters)

Let’s be honest—entrepreneurship is an emotional rollercoaster. In this episode of Five with Fry, I’m back with my mentor Ty Smith for part two of our conversation, and we’re getting into the real stuff: the emotional weight of building something from scratch and how to keep going when things get hard.

We talk about the gut-punch of rejection, the power of hearing “no” as “not yet,” and why learning to take feedback (without taking it personally) is a game-changer. Ty shares stories from the trenches, and we get into how even the most seasoned professionals can find entrepreneurship to be their toughest challenge yet.

Then, we shift gears and talk about something that doesn’t get enough attention: community. Especially for Black and Brown founders, the startup world can feel isolating—but it doesn’t have to be. We break down the dangers of relying only on friends and family for feedback, the trap of scarcity mindset, and the real magic that happens when we choose collaboration over competition.

If you’re building something and feeling the weight of it all, this episode is your reminder that you’re not alone—and that growth comes from both vulnerability and connection. Let’s talk about how to build a business and a community that lasts.

In this bonus episode of Five with Fry, I’m diving into a recent viral moment from the track world that’s got everyone talking—and not for the right reasons. A female athlete was caught on camera deliberately striking another runner during a relay race, then followed it up with a classic “non-apology” that did more harm than good. Sitting next to her parents, she delivered an implausible story about a baton mishap and losing her balance—despite video evidence clearly showing otherwise.

This situation is a textbook case of what happens when we dodge accountability instead of owning our mistakes. As I say in the episode, “Nothing has ever come from someone lying and not apologizing—nothing.” Whether you’re on the track, in a meeting, or navigating personal relationships, authentic apologies matter. They require vulnerability, honesty, and the ability to center the person who was harmed, not our own discomfort.

Tune in for a real talk about accountability, integrity, and why the coverup is almost always worse than the original offense. Let’s break the cycle of fake apologies—and learn how to actually do better.

Follow me on IG, Twitter, and TikTok @JenFryTalks, or connect with me on LinkedIn at Dr. Jen Fry. Stay curious, stay bold, and keep the conversation going.

Avoiding the Traps of Overconfidence: Five Lessons for New Entrepreneurs with Ty Smith

What if the biggest obstacle to your startup’s success is… you? In this episode of Five with Fry, I sit down with veteran lean startup consultant Tyrome "Ty" Smith to unpack the common missteps that trip up new entrepreneurs—like overconfidence, skipping market research, and asking the wrong questions.

Ty shares wisdom from 25+ years of experience, breaking down why customer discovery isn’t just a box to check—it’s the heartbeat of any successful business. You’ll learn how to conduct meaningful customer interviews, avoid the trap of false validation, and embrace the emotional resilience needed to adapt and grow. Inspired by Frank Gehry’s advice not to fall in love with your first idea, this conversation is a must-listen for founders navigating the messy, exciting world of entrepreneurship.

Stay curious, stay bold, and—most importantly—keep asking the right questions. Got a topic you want us to cover? Let us know!

More about Ty: Tyrome ‘Ty’ Smith has over 25 years of consulting and leading executives and their teams by helping them understand human and organizational dynamics. As part of his work, He developed an innovative education program for the Department of Defense, including coaching and mentoring product development teams engaged in an internal incubator. In addition, he has provided support to several organizations either as faculty or entrepreneur-in-residence, including Bowie State University, University of Maryland Innovation Extension Program, StreetCode Academy, Digital Undivided, and TechStars. Connect with him on LinkedIn.

The Soft Skill That Will Make or Break Your Career

We hear a lot about hard skills—degrees, certifications, technical know-how. But what about soft skills? You know, the ones that actually determine whether you thrive in your workplace.

In this episode of Five with Fry, we're talking about the soft skill that people love to avoid: conflict management.

Too often, conflict gets labeled as a workplace problem when, in reality, it’s an opportunity for growth, innovation, and stronger team dynamics. The issue? Most of us haven’t been taught how to navigate it. Organizations talk about wanting leaders, but do they prioritize skills like communication, problem-solving, and de-escalation in their hiring processes?

Here’s what we’re digging into:

• Why the soft skills vs. hard skills debate is misleading
• How conflict resolution can transform work culture (and your career)
• Why companies need to rethink job descriptions to highlight what really matters

Conflict isn’t something to avoid. It’s something to get better at. Tune in to this conversation and start seeing soft skills as the real power moves in your career.

If this episode resonates with you, subscribe, share, and leave a review.

When a Fun Volleyball Trend Becomes a Lesson in Consent

What happens when a seemingly harmless sports tradition gets people fired up about consent?

In this episode of Five with Fry, we’re talking about clipping—a popular trend in volleyball where players pin decorated clothespins onto each other. Sounds fun, right? But what happens when a player doesn’t want to be clipped? What happens when a young girl feels uncomfortable but doesn’t know how to say no?

That’s where this conversation takes a turn.

When I brought up concerns about this in a volleyball moms Facebook group, the backlash was real. People argued that clipping was “just for fun” and that “no harm was meant.” But here’s the thing: intent doesn’t override consent.

This episode isn’t just about sports—it’s about the bigger lesson we should be teaching young girls: how to set and enforce their boundaries. If we don’t give them the space to practice saying no in low-stakes situations, how can we expect them to do it when it really matters?

We’re diving into:

• Why traditions like clipping highlight the challenges young girls face in asserting themselves.
• The difference between good intentions and real consent.
• How early consent education builds confidence and autonomy.
• Why empowering girls to say “no” isn’t about taking the fun away—it’s about ensuring their voices are heard.

This isn’t about overreacting. It’s about recognizing how small moments teach big lessons. And if we want to raise a generation of young women who know how to hold their boundaries, we need to start paying attention.

Tune in to this episode of Five with Fry and let’s talk about why consent always matters—even when it’s “just for fun.”

Not Everything is Meant for You—And That’s Okay

Let’s talk about Kendrick Lamar’s Super Bowl halftime show—the performance that had some people on their feet and others scratching their heads. Was it a cultural masterpiece, or did it just not land for you? Either way, that’s completely okay—because not everything is meant for everyone.

On this episode of Five with Fry, we’re diving into the mixed reactions to Kendrick’s performance—what worked, what didn’t, and why some folks just couldn’t connect with it. We’ll unpack:

• Why audience expectations don’t always align with an artist’s vision
• The importance of understanding that not all art is made for you
• How critiques around politics, sound issues, and style reveal deeper biases
• The wisdom of a white mom teaching her kids that stepping outside their comfort zone is a good thing

If you loved it, let’s talk about why. If you didn’t, let’s explore what that means. Because in a world where entertainment is more than just mindless fun—it’s also cultural, political, and personal—it’s worth asking: What happens when we challenge ourselves to engage with art beyond our own experiences?

Join me for this deep (and fun!) dive into what it means to appreciate, critique, and expand our understanding of performance, culture, and artistic expression.

What does it really mean to be an ally in 2025? In this episode of Five with Fry, I sit down with Dr. Victoria Farris to unpack how "Good Girl" conditioning holds white women back from stepping fully into anti-racism work.

Dr. Farris, an expert on social conditioning, breaks down how ingrained behaviors—like the fear of making waves or the need for approval—can lead to silence when it matters most. We explore five critical questions that challenge white women to confront their complicity, embrace discomfort, and align their values with action.

From personal accountability to the risks (and rewards) of speaking out, we dive into what it truly takes to shift from performative allyship to transformative leadership. It’s time to break free from social norms that prioritize comfort over justice.

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Dr. Victoria Farris is a transformational leadership facilitator and coach working with executive leaders who want to move beyond surface-level DEI efforts and truly create inclusive, high-performing teams. Her approach combines leadership development, strategic alignment, and trust-building frameworks to equip teams with the tools they need for lasting impact. Her research focuses on understanding, from the perspectives of folks of color, what white people can do to disrupt and dismantle systems of racism, and she has developed a framework for effective allyship that outlines an action-based guide for disrupting racism on individual, group, and organization levels. Victoria is also a mother, activist, hypnotherapist, and avid joy seeker.

Let’s be honest—feedback can be tough. Whether you're receiving it or giving it, it’s not always easy to navigate. But what if we stopped seeing feedback as something to fear and started using it as a tool for growth?

In this episode of Five with Fry, I’m sharing my own journey from hating feedback to embracing it as a catalyst for change. Inspired by Wes Kao’s expertise in communication, I dive into the power of precise, intentional feedback—because “looks good” just doesn’t cut it.

Here’s what we’re tackling:

• Why vague feedback isn’t helpful & how to be more specific
• How to receive feedback with grace (even when it’s uncomfortable)
• The role of feedback in resolving conflicts—at work, in sports, and in families
• Practical strategies to create a feedback-friendly environment

Feedback isn’t about tearing people down—it’s about building them up. But that only happens when we learn how to give it clearly and receive it without shutting down.

Ready to level up your feedback game? 🎧 Tune in now, and let’s break the cycle of defensive reactions and unclear communication.

And as always, let me know—what’s the best (or worst) feedback you’ve ever received? DM me on IG/Twitter/TikTok @JenFryTalks or find me on LinkedIn at Dr. Jen Fry. Let’s keep the conversation going!

We need to talk about boundaries—especially in families. Why is it that when someone sets a boundary with their parents, it’s often seen as disrespectful? In this episode of Five with Fry, I’m diving into the intense online debate sparked by a simple request: a young woman asking her smoking mother to step outside. The backlash? Unreal. But it reveals something deeper—why do so many people believe parents are exempt from respecting boundaries?

Let’s be clear: boundaries aren’t just important; they’re transformative. They protect personal space, emotional well-being, and autonomy. And they aren’t just for adults—kids need to learn to advocate for themselves too. If we want future generations to grow into confident, self-respecting individuals, we have to shift the mindset that setting limits equals defiance.

In this episode, we’re breaking it all down:

• The societal pushback against setting boundaries with family
• Why teaching kids to say "no" is an act of empowerment
• Cultural expectations that blur the lines of parental access
• How boundaries create healthier, more respectful relationships

Remember: if you love what you hear, don’t forget to subscribe, share, and leave a review! Want me to tackle a specific topic? Drop me a message. You can follow me on IG, Twitter, and TikTok @JenFryTalks or find me on LinkedIn at Dr. Jen Fry. Let’s keep the conversation going!