#111 - How to Talk About Your Value at Work (Without Sounding Arrogant)

Jul 15, 2025

episode NOTES

Should you shave before a date? Is it okay to show up to a date in work clothes? When will you finally know what you want to do with your life? In this Ask Me Anything episode of Guyset, I pull 10 real listener questions from my Spider-Man bucket hat and deliver honest and real advice for guys navigating their twenties. From dating anxiety to career setbacks, friendship changes to quarter-life crisis fears, these are the questions you've thought about but never knew who to ask.

Timestamps:

03:28: "Should I shave before my date?"

05:41: "Is it all right to show up on a first date in work clothes?"

08:02: "Is it bad if I'm a bad texter for dating?"

12:35: "A lot of my friends are moving and I'm feeling anxious about how far apart we're all going to be. I don't know if there's any advice for this, but I'm wondering if other people are feeling this way too."

19:44: "My girlfriend and I have been together for a year. What should I get her?"

22:07: "Should I keep a condom on me?"

24:18: "My recent review at work wasn't as good as I wanted it to be. What should I do?"

29:00: "When should I feel like I know what I want to do?"

33:44: "Any tips to help me get out of a slump? I'm feeling really lazy recently."

38:05: "When do you think a girl should start paying for dates?"

What You'll Learn:

Dating & Relationships: Pre-date grooming essentials, texting etiquette that actually works for dating, and perfect one-year anniversary ideas

Career Challenges: How to bounce back from bad performance reviews and turn criticism into career growth

Life Transitions: Dealing with friends moving away and the anxiety of post-college life changes

Personal Development: Morning routine hacks to beat laziness and build momentum

Real Talk: When you should actually know what you want to do (spoiler: probably not yet)

Perfect for: Guys in their twenties dealing with dating stress, career confusion, friendship changes, or general life anxiety.

Also great for anyone who wants honest perspectives on modern masculinity and relationships.

Why This Episode Hits Different: It's 10 Questions Every Guy in His 20s Is Asking (But Won't Say Out Loud). This isn't your typical self-help podcast. I'm going through the exact same struggles as my listeners – quarter-life anxiety, career uncertainty, watching friend groups scatter. My advice comes from lived experience, not a textbook.

Subscribe to Guyset for weekly conversations about what should be talked about for guys in their twenties.

New episodes every Tuesday.

Submit your questions for future Dear Guyset episodes:

DM: @theguyset

Email: josh@guyset.com

Website: guyset.com

Connect with me:

Instagram: @guysetpodcast

TikTok: @theguyset Watch the full episode on

YouTube: @guyset

Website: guyset.com

Email: josh@guyset.com

Ask Me Anything: guyset.com

Read my substack: guyset

See you next Tuesday!

MORE ON THIS EPISODE

How to Talk About Your Worth at Work: A Young Professional's Guide to Confidence

From anxiety-inducing boss meetings to confidently presenting your value—here's how to master the soft skills they don't teach in college.

The Skills They Don't Teach You

Four years of work experience teaches you things no classroom ever could. Not Excel formulas or SQL queries, but the soft skills that actually determine your career trajectory: how to talk to people, conduct yourself in new settings, defend your work, and most importantly—how to show your value.

These aren't skills you can learn from a textbook. They come from making mistakes, getting thrown into uncomfortable situations, and figuring it out as you go. But there's a framework you can use to navigate these conversations with confidence instead of fear.

The Conversation That Changed Everything

Picture this: Your boss leaves the company. Suddenly, you're reporting directly to the CEO. There's a meeting on your calendar titled "Check-in," and you have no idea what to expect.

This exact scenario happens to thousands of young professionals every year. The anxiety is real—you don't know their management style, their expectations, or how to prove your worth to someone who barely knows what you do.

But here's what most people don't realize: You probably have more value to present than you think.

The Sunday Night Realization

After spending an entire weekend anxious about an upcoming boss meeting, there's often a moment of clarity. You realize you've actually been doing good work—you just need to organize your thoughts and present them effectively.

The shift happens when you stop waiting for someone to ask you questions and start leading the conversation yourself. Instead of going in defensive, you go in prepared to showcase your contributions.

The Three-Example Framework

Here's the strategy that transforms nerve-wracking boss conversations into opportunities to shine:

Bring three specific examples of projects or initiatives where you made a measurable impact. Not just "I worked on this project and it was successful," but:

  1. The initiative you started or contributed to

  2. The reasoning behind it and how you defended it

  3. The concrete results it delivered to the company

Making It Data-Driven

Numbers make your contributions undeniable. Instead of saying "this was successful," you say "this brought in $X in revenue" or "this generated X leads" or "this improved our conversion rate by X%."

When you back your claims with data, the conversation shifts from opinion to fact. They can't argue with results.

The Before and After: A Confidence Case Study

A Year Ago:

  • Boss: "How are things going?"

  • You: "Things are good! Things are moving! I'm working on this and that, super energized, met great people..."

  • Boss: "What are you working on specifically?"

  • You: "You know, the things we talked about... I'm working on this and this... making progress..."

  • Boss: "I want to see results. I want to see your impact. I want numbers and data."

  • You: "Yeah, I can do numbers! I love numbers!"

After Learning This Framework:

  • You: "I want to show you three initiatives I've been working on and their impact on our goals."

  • You: "First, I proposed [specific project], defended it with [reasoning], and when we executed it, it brought in [specific results/revenue]."

  • You: "The data shows [concrete numbers] that directly contributed to our [relevant company metric]."

The difference is night and day.

The Sandwich Strategy

For promotion or raise conversations, use this structure:

  1. What you've already accomplished (your three examples with data)

  2. What you're asking for (the promotion, raise, or responsibility)

  3. What you'll continue to deliver (future projects and commitments)

This approach shows you're not just asking for something—you're demonstrating past value and promising future contributions.

Why This Matters Beyond One Conversation

Learning to present your value effectively is how you become irreplaceable. It's the difference between being seen as someone who "does their job" versus someone who "drives results."

This skill compounds over time. The person who can confidently discuss their contributions with one boss can do it with the next boss too. The confidence you build presenting your work translates to every professional interaction.

The Soft Skills That Actually Matter

When you feel like you're not learning or growing at work anymore, consider focusing on these soft skills:

  • How to talk to people in professional settings

  • How to conduct yourself in new environments

  • How to defend yourself and your work

  • How to stand up for yourself professionally

  • How to present your work compellingly

  • How to communicate your value clearly

These skills are constantly evolving because every boss, coworker, and company culture is different. There's always more to learn about reading the room and adapting your communication style.

Learning from Rejection: The Barbara Corcoran Method

Sometimes the most powerful way to show your value is when facing rejection. Barbara Corcoran's letter to get on Shark Tank after being initially rejected demonstrates bold value presentation:

  • She acknowledged the rejection directly

  • She listed specific reasons why she deserved consideration

  • She backed her claims with concrete examples from her past

  • She positioned her unique value proposition

  • She ended with confidence, not desperation

While this approach might be too bold for most workplace situations, the principle remains: Know your value, articulate it clearly, and don't be afraid to advocate for yourself.

The Confidence That Comes from Preparation

The transformation from anxiety to confidence happens when you shift from hoping you can wing it to knowing you have concrete examples to share. When you walk into a room with data-backed accomplishments, you're not making things up on the fly—you're sharing factual evidence of your contributions.

This isn't about bragging. It's about professional communication and ensuring your contributions are visible and recognized.

Your Action Plan

  1. Audit your recent work. Identify 2-3 projects where you made a measurable impact

  2. Gather the data. Find the numbers that show your contributions (revenue, leads, efficiency gains, etc.)

  3. Practice your presentation. Be ready to explain not just what you did, but why it mattered and what results it achieved

  4. Update your resume regularly to keep track of your accomplishments as they happen

  5. Look for the next opportunity to practice presenting your value—don't wait for annual reviews

The Long Game

Mastering this skill early in your career pays dividends forever. Every job change, every promotion conversation, every networking opportunity becomes easier when you can confidently articulate what you bring to the table.

Remember: You probably have more value than you realize. The key is organizing your thoughts, backing them with data, and presenting them with confidence.

The workplace doesn't come with an instruction manual for these conversations. But now you have a framework to navigate them successfully.

Listen to the Full Episode

This insight comes from Guyset: A Guy's Guide to What Should Be Talked About, hosted by Josh Felgoise. For more honest conversations about navigating workplace challenges and building confidence, find the full episode on:

  • YouTube: Search for "Guyset" or visit the Guyset channel

  • Instagram & TikTok: @theguyset

  • Website: guyset.com

  • Email: josh@guyset.com

New episodes drop every Tuesday with real advice for real workplace situations.

What's one accomplishment from your current role that you could better articulate with specific data and results? Start there.