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.