Do you thrive as the subject matter expert at work, but feel drained by constant interruptions? If this sounds familiar, you might be, or work alongside, an Enneagram Type 5.

In this episode of the Work Happy series, Jen Stanley sits down with Casey Ash, a Type 5, to explore what daily work life looks like through the lens of the Enneagram. They discuss:

• Why autonomy and expertise are the sweet spot for Enneagram 5s

• The temptations for 5s to retreat into “depth over breadth” in their careers

• A powerful mindset shift that can help 5s unlock long-term career development and growth

Want to put this into practice? Don’t miss Jen’s Designed for More class, the final Enneagram class offered this year. Podcast listeners receive an exclusive discount! Register HERE.

LINKS to socials, website, or to book a call with Jen HERE!

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Where are you spending your emotional energy each day?

Enneagram Type 4s are known for their creativity, authenticity, and emotional intelligence. But without balance, that deep well of feeling can leave you drained and burned out, especially in the workplace.

In this episode of Work Happy, Jen Stanley sits down with Sarah McLaughlin, an Enneagram 4, to explore:

• The importance of balance when it comes to your emotional “workload” 

• Why creating an emotional “balance sheet” protects your creativity and energy

• How Type 4s can lean into authenticity without exhausting themselves

  
  

If you’re an Enneagram 4 or you work with one, this episode will give you a practical shift to thrive at work while honoring your unique gifts.

DON’T MISS OUT ON THE LAST ENNEAGRAM CLASS OF 2025! Podcast listeners get a $99 discount on Jen’s Designed for More class (also called Authentically You), so tune in for the code and grab your spot! Register HERE!

LINKS to socials, website, or to book a call with Jen HERE.

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Enneagram 3s, you dream big, achieve big, and dominate in the workplace. But if your worth is tied to your work, you’ll always be left disappointed.

“Work is not a good lover, because it is impossible to work hard enough or long enough hours to make everyone in the world love you.” – Jen Stanley

In this episode of the Work Happy series, Jen interviews Kimberly Majeski, an Enneagram 3 and executive director of a global women’s organization. Together, they unpack what it really looks like to thrive as a Type 3 in the workplace without losing yourself to overachievement.

It’s powerful when you go deeper with the people in your life—friends, spouses, co-workers—and learn to be valued for who you are rather than just what you accomplish.

Don’t miss out! Tune in now and claim your special podcast discount for Jen’s Designed for More class. Register HERE.

Click HERE for links to socials, website, or to book a call with Jen!

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Staci Bemis, an Enneagram Type 2 and HR professional, shared how hard it was to put her phone away at night, afraid she’d let someone down. She admitted that when she wasn’t invited to meetings, she felt offended. Can you relate?

““Having a 2 in the workplace is truly a gift. Not only are they willing to chip in, lend a hand, and help with projects, they are also going to be relationally in tune with everyone around them.” — Jen Stanley

But here’s the challenge for Type 2s at work:

• Pride can masquerade as being the “superhero” who saves the day

• Overextending to appear successful only leads to exhaustion

• Instead of thriving in relationships, 2s end up sacrificing them

  
  

In this Work Happy episode, Jen and Staci talk about how Enneagram 2s can:

• Set healthy boundaries at work

• Embrace work-life balance

• Learn to rest in being loved for who they are, not just what they do

  
  

“Bringing your shadow into the light breaks its power almost immediately.” — Jen Stanley

Want to go deeper? In week 2 of my Designed for More class, we dig into these shadows and learn how to grow through them. Podcast listeners get a $99 discount! Register HERE!
LINKS to socials, website, or to book a call with Jen HERE.

Enneagram 1s bring incredible gifts to the workplace—discipline, organization, follow-through, and a natural ability to spot opportunities for improvement.

Julie Williams, an Enneagram 1 and a school administrator, put it this way, “I love that I can see people’s unique skills and strengths so naturally. For me, it’s like a spotlight. I also love watching people grow and helping people grow, because we love improvement.”

But the Enneagram 1s face a huge challenge. As a part of the doing triad, Enneagram 1s are always giving 100 percent to make their environment better. That effort can lead to exhaustion and burnout. 

In this episode of the Work Happy Series, Jen Stanley explores:

• Why not everything deserves your full 100 percent effort

• How to use questions and mantras to reset and slow down

• The essential role of boundaries in protecting Type 1s’ health and wellbeing

  
  

If you are an Enneagram Type 1, or you work alongside one, this episode will give you practical insight into how 1s can thrive in the workplace while finding balance and fulfillment.

Want more tools? Sign up for Jen’s Designed for More class and get a downloadable PDF of mantras and reflection questions for every Enneagram type. Podcast listeners receive an exclusive class discount! Register HERE!

LINKS to socials, website, or to book a call with Jen HERE.

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What do H&R Block, Delta, and Nike have in common? They’re global leaders in work wellbeing. But according to Indeed’s Global Work Wellbeing Report, only 22% of employees say they’re thriving at work. Stress, burnout, and unhappiness are at an all-time high.

That’s why I’m launching a brand new series: Work Happy. In this series, you’ll discover:

• How your Enneagram number (and the Enneagram number of your coworkers) impacts your work and workplace

• The unique strengths you bring to your team

• Simple strategies to improve your wellbeing and happiness at work

  
  

Whether you’re trying to navigate a difficult workplace, lead a team with more awareness, or simply want to enjoy your job more, this series is for you!

Don’t just survive the 9-to-5. Learn how to work happy.

Want more? Sign up for my Designed for More class and get a downloadable PDF of mantras and reflection questions for every Enneagram type. Register HERE.

LINKS to socials, website, or to book a call with Jen HERE!

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Does the question “What do you want?” stress you out? You might be an Enneagram Type 9, also known as the Peacemaker or the Mediator. 9s are easy-going, conflict-avoiding, and often put others’ needs ahead of their own. But constantly merging with everyone else’s desires can come at a cost.

In this episode of The One Question That Will Change Everything, Jen Stanley shares a transformative question that helps 9s:

• Reconnect with their own wants and needs

• Take small, confident steps toward healthy conflict

• Find their voice and prioritize their desires without guilt

  
  

Did you enjoy this series? Which question has been the most helpful for you? Drop your thoughts in the comments!

Want to go deeper or have more tools to navigate all the craziness of being human? It’s not too late to join Jen’s Enneagram 101 class!  Register HERE.

LINKS to socials, website, or to book a call with Jen: https://linktr.ee/Livingwellbyjenstanley⁠⁠

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Enneagram Type 8s, this one is only for the brave!

Do you feel a current of anger or frustration bubbling just beneath the surface? You might be an Enneagram 8. Known as The Challenger, Type 8s are powerful, passionate, and driven, but often avoid vulnerability at all costs.

In this episode of The One Question That Will Change Everything, Jen Stanley shares a tough but transformative question designed specifically for Enneagram 8s. This question will help you:

• See what’s truly going on beneath anger and frustration

• Pause and choose your response with clarity instead of reactivity

• Step into vulnerability and discover the deeper connections you crave

  
  

“When you can get truly in touch with the softer emotions, it allows you to bond and connect with the people that you care about in a very real and deep way.” – Jen Stanley 

Tune in now to understand strength, vulnerability, and connection in a whole new way.
Ready to go deeper? Join Jen’s Enneagram 101 class to experience more peace of mind, stronger relationships, and a deeper sense of what it means to be fully human. Register HERE!

LINKS to socials, website, or to book a call with Jen: https://linktr.ee/Livingwellbyjenstanley

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“All humans have a wide range of emotions, and not acknowledging that doesn’t allow you to be whole.” – Jen Stanley

Do you feel like no matter how much you chase happiness, unhappiness still finds you? You might be an Enneagram Type 7, the Enthusiast.

Type 7s are known for their optimism, creativity, and love of adventure, but they often struggle with:

• An insatiable need to have something exciting on the horizon 

• Escaping the present moment to avoid pain or discomfort

• Over-focusing on their own experiences instead of building deeper connections

• Difficulty embracing the full range of emotions beyond happiness

  
  

In this episode of The One Question That Will Change Everything, Jen Stanley provides a powerful question that helps Type 7s slow down, stay present, and embrace wholeness. By leaning in, 7s can stop running from discomfort, discover real satisfaction, and experience more authentic relationships. 

Want to go deeper? Join Jen’s Enneagram 101 class and learn how to become better at being human, more at peace in your own mind, and stronger in your relationships. You won’t want to miss it! Register HERE!

LINKS to ⁠socials⁠, ⁠website⁠, or to ⁠book a call ⁠with Jen ⁠HERE⁠.

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Do you struggle with indecision, self-doubt, or overthinking every possible outcome? You might be an Enneagram Type 6 (The Loyalist).

In this episode of The One Question That Will Change Everything, Jen Stanley dives into the unique challenges and strengths of Type 6s, and shares a powerful question that helps 6s:

• Break free from the cycle of doubt and constant second-guessing

• Build courage and practice self-trust in the present moment

• Identify fear as the real enemy holding you back

• Stop over-analyzing every option and start taking action

  
  

Enneagram 6s are incredibly gifted at foresight, preparation, and loyalty, but the pressure to always plan for every scenario can lead to anxiety and hesitation. This episode will help you learn how to trust yourself, step into courage, and find peace beyond fear. 

Ready to go deeper? Join Jen’s Enneagram 101 class and learn how to become better at being human, find more peace of mind, and strengthen your relationships. Register HERE!

LINKS to socials, website, or to book a call with Jen HERE.

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