Welcome back to The Glass Sessions!

This week, we’re diving into the world of side hustles with Hailey Ben-Izhak, a multi-hyphenate entrepreneur who’s turned her side projects into a full-time career.

Hailey shares what it’s really like to balance multiple ventures - from running a photo booth company to working in healthcare tech - and what she’s learned about time, energy, and focus along the way.

We cover everything from being transparent with your employer to knowing when to scale, pause, or pivot. Whether you’re dreaming about launching a side hustle or already juggling a few, this episode is full of insight on how to grow without burning out.

We discuss:

• How to balance a side hustle with a full-time job

• Being transparent with your employer (what to consider and why it matters)
• Time management and setting boundaries

• The difference between overwhelm and growth discomfort
• How therapy, self-reflection, and community support long-term success
• Using your professional network and personal brand to fuel growth

Timestamps:

00:00 - Side chat and what we've learned recently

9:30 - Discussion on side hustles

57:57 - Is this okay? Making a case to your manager to attend a conference

Links & Resources:

Hailey's LinkedIn: https://www.linkedin.com/in/hailey-ben-izhak/

⁠⁠⁠Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Description:

In this episode of The Glass Sessions, we break down how to evaluate a company before determining if it'd be a place you'd want to join.

We cover:

• What to look for on company websites, job descriptions, and press releases
• How to evaluate benefits, compensation philosophy, and financial health
• Smart ways to read employee and client reviews (with a grain of salt)
• Questions that reveal real growth opportunities during interviews
• The green flags that signal healthy organizations
• The red flags that suggest it’s time to move on

Whether you’re job-hunting, interviewing, or just re-evaluating where you are, this episode will help you build the confidence and clarity to make career decisions that align with your values.

Timestamps:

00:00 - Side chat and what we've learned recently

10:02 - Discussion on how to evaluate a company

44:59 - Is this okay? Handling negative feedback about a colleague

Links & Resources:

⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

In this episode of The Glass Sessions, Courtney and Lauren talk about how to close out the year with clarity, energy, and intention instead of just sprinting to the finish line.

We share practical ways to align with your manager before year-end reviews, build momentum on key goals, and communicate clearly about what’s next. We dive into how to tell the story behind your results, especially if you may not be on the path to hitting all of your goals, and how to reframe those experiences to strengthen trust and growth.

You’ll hear actionable advice on:

• Conducting a personal and professional audit before Q4 ends

• • Using the Why / How / What framework to clarify your next move
• • Making a case for change or promotion
• • Taking advantage of underused employee benefits
• • Strengthening your network before the holidays

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  Timestamps:
  00:00 - Side chat and what we've learned recently

  10:11 - Helpful tips and strategies to set yourself up for success in the last quarter of the year

  45:19 - Is This Okay?: Applying for a new internal role after my manager has been teasing a promotion for years.

  
  

  Links & Resources:

  ⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

  ⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

  Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

  If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

In this episode of The Glass Sessions, hosts Lauren and Courtney sit down with Katelyn Lopez, VP of Customer Success at Comprehensive, to unpack one of the most complex, and often confusing, parts of work: compensation.

Katelyn shares her expertise on:

• How to think about compensation philosophy and why it matters

• The building blocks of total rewards systems-salary, equity, benefits, PTO, and beyond

• What employees should know about pay transparency, equity, and negotiation strategies

• The common challenges managers face during compensation cycles and how to navigate them

Timestamps:

00:00 - Side chat and what we've learned recently
10:10 - Deep dive on compensation with Katelyn Lopez
01:04:22 - Is This Okay?: Two weeks’ notice in 2025

Links & Resources:

Katelyn's LinkedIn: https://www.linkedin.com/in/katelynmdennis

Comprehensive's Free Market Data Tools: https://app.comprehensive.io/benchmarking/s/jobFamily=Software+Engineering&level=IC3

⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

Trust is the quiet superpower that opens doors at work and in life. In this episode, Courtney and Lauren chat about what actually builds trust - from the little habits (showing up on time) to the big practices (admitting mistakes, being transparent, and giving credit). Expect candid stories, generational perspectives, and practical tips you can start using in your next meeting.

What you’ll learn:

• • Why trust is a career multiplier - not a soft skill.
• • Concrete behaviors that build credibility (and the habits that quietly erode it).
• • How storytelling and social proof amplify trust.
• • Practical ways to show respect for others’ time, and why it matters.
• • Tips for handling salary conversations with integrity and confidence.

  
  

  Timestamps:

  00:00 - Side chat and what we've learned recently

  14:55 - Discussion on value of trust and how to build and keep it

  51:11 - Is this okay? Recruiters have reached out with jobs that pay significantly more than I make. Is it okay to ask my manager for a higher salary based on what I'm seeing in the market?

  
  

  Links & Resources:

  ⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

  ⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

  Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

  
  

  If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

In this episode of The Glass Sessions, Courtney and Lauren unpack the idea of “job hugging” - when employees stay in their current roles not because they love the work, but because the job market feels too uncertain to make a change.

They share personal stories and dig into the hidden costs of job hugging: missed earnings, lack of engagement, and a culture that quietly slips into complacency. Together, they explore how to recognize if you (or your team) might be clinging to a role for the wrong reasons, and what to do about it.

Listeners will walk away with strategies to re-ignite career growth and team energy, including:

• • How to use continuing education benefits wisely
  • Ways to spark engagement through fresh opportunities
  • Aligning personal development goals with company objectives
  • Tips for leaders to balance healthy attrition with a thriving culture

  Whether you’re an employee wondering if you’re stuck, or an employer wanting to keep your team engaged, this episode offers practical advice to navigate uncertainty with clarity and confidence.

  Timestamps:

  00:00 - Side chat and what we've learned recently

  13:13 - Introduction to job hugging

  51:09 - Is this okay? A teammate that reports into me seems very down in the office. Is it okay to talk to them about their demeanor?

  Links & Resources:

  ⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

  ⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

  Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

  
  

  If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

In this episode of The Glass Sessions, Courtney and Lauren sit down with Allie Fisher, a San Francisco-based independent creative director and designer. She describes herself as a curious creative generalist, and partners with clients to craft strategic visual systems and emotive narratives across brand, editorial, and film.

Allie started her career working as a designer and art director at Conde Nast and WIRED, where she brought stories to life across platforms—from magazine covers to live events. She then made the shift to a brand studio called Godfrey Dadich Partners, where she led the creative team as Partner, Head of Creative—working with clients such as Nike, Netflix, Microsoft, and NatGeo. Last year she launched her independent consultancy, Studio Fisher, where she partners closely with organizations who want to forge a deeper connection with their audience.

Together, they explore:

• Why a personal brand is more than just a LinkedIn headline or a polished résumé
• How uncovering your “why” can guide the way you tell your story and show up with confidence
• Practical steps for aligning your values with your professional identity
• Tips for using your personal brand to stand out in job searches, networking, and career growth

Allie shares her approach to translating your internal compass into an external narrative that resonates, plus insights on how to audit and refine your brand over time.

Timestamps:

00:00 - Side Chat and what we've learned recently

• 12:32 - Building a personal brand at work

• 32:41 - The importance of authentic branding

• 37:59 - Identifying and engaging your audience

• 42:59 - Using the Why / How / What framework

• 1:00:59 - Is this okay? Not sending a follow-up email after an interview

  
  

  Links & Resources:

  • Allie Fisher's website: www.allie-fisher.com
  • Allie's Instagram: www.instagram.com/allie_fish
  • ⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast
  • The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com
  • Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

  
  

  If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.

Episode Summary:

Ever felt like you don’t quite belong, even when you’ve earned your seat at the table? You’re not alone, and you don’t have to stay stuck there.

In this episode of The Glass Sessions, Lauren and Courtney discuss their own battles with imposter syndrome and how they’ve worked through those feelings while growing their careers and building The Glass Advisory.

They share practical strategies to help you shift from self-doubt to confidence, including:

• Creating psychological safety at work
• Balancing external validation with your own internal compass
• Turning preparation and practice into confidence-boosting habits
• Recognizing how past experiences and support systems shape the way you show up today

By the end, you’ll walk away with actionable takeaways to help you quiet the voice of “not enough” and step fully into your strengths.

Timestamps:00:00 - Side chat and what we learned recently
22:06 - Spotting limiting beliefs
26:57 - Internal vs. external validation32:15 - Building confidence through practice40:48 - Is this okay? My team is expected to volunteer to host webinars and I don't feel comfortable raising my hand

Links & Resources:

⁠⁠⁠Detailed Show Notes⁠⁠⁠: https://www.theglassadvisory.com/theglasssessionspodcast

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

Have a workplace situation you'd like us to talk through? ⁠⁠Submit it here⁠⁠: ⁠https://www.theglassadvisory.com/contact⁠

If you’re interested in one-on-one career advising or want to partner with The Glass Advisory to support your growing business, visit us at ⁠⁠⁠⁠theglassadvisory.com⁠⁠⁠⁠.