From Midlife to Best Life

This is a podcast dedicated to celebrating one of the most empowered, fun and challenging phases of life - midlife. Podcast hosts Iris and Ana (proud midlifers) invite their audience in on friendly, authentic and important conversations about anything related to midlife: relationships, career, transitions and other rich topics. They share personal stories, research insights, and learnings from their daily lives to inspire folks approaching or living midlife embrace fulfilling and rewarding lives.

Episodes

Aug 28, 2025

28 min

Episode Summary:
In this episode of "From Midlife to Best Life," host Ana welcomes career coach Trudy Hallam from LHH Knightsbridge. Together, they explore the emotional and practical aspects of navigating career transitions, especially during layoffs. Trudy shares insights on how to prepare for unexpected changes, the importance of maintaining a "kudo file," and how to leverage personal branding in job searches. Ana shares her own experience with the recent layoff and how she turned it into an opportunity to re-discover herself. Tune in to discover how career coaching can be a vital support system in uncertain times. 
Takeaways: 
Layoffs are disruptive but normal experiences. They bring shock, sadness, and identity loss, but they can also create opportunities to pause, re-evaluate, and pivot in one’s career. Be vulnerable. Be kind. Be human.
Be proactive before a layoff happens. Keep a “kudos file” with performance reviews, accomplishments, and samples of work stored outside your work computer. This ensures you have evidence of your skills and achievements if access is cut off.
Take advantage of outplacement and career coaching services. Many people don’t use these resources, but they provide resume support, interview preparation, training, and guidance on navigating the job market.
Think beyond traditional full-time roles. Contract, part-time, or portfolio careers can offer flexibility, new experiences, and pathways into unexpected opportunities.
Develop and market your personal brand. Employers look for more than hard skills. Highlight transferable strengths (e.g., leadership, problem-solving, creativity) and communicate what makes you unique.
Host: Ana Yun [Instagram | Website: www.anayun.ca | LinkedIn Profile]
Guest: Trudy Hallam [LinkedIn Link]
Resources:
LinkedIn Learning – free with through your local library.  Over 16,000 courses and instructional courses on interviewing; resumes; marketing plans; LinkedIn and everything in-between.
 
LinkedIn Learning Role Play:  As Career Coaches seek practical tools to boost a candidate’s confidence, LinkedIn Learning’s Role Play offers a game-changing solution. This AI-powered platform simulates real-world interview scenarios, allowing candidates to rehearse responses to common questions in a safe, interactive environment. It provides instant feedback on tone, clarity, and delivery—helping job seekers refine their communication skills and reduce interview anxiety. With customizable scenarios across industries, it’s ideal for candidates at any career stage. Encourage your candidates to use Role Play as part of their interview prep—it’s like having a virtual coach available 24/7 and is a great resource for alumni candidates too. 
 
The Job Bank’s “Get to Know Yourself” resource is a valuable tool for Canadian career coaches to guide candidates through self-reflection as the foundation of career planning. It offers quizzes and exercises to help individuals identify their strengths, skills, values, and preferences, enabling them to make informed career decisions aligned with their authentic selves. Coaches can use this resource to facilitate discussions, encourage honest self-assessment, and connect candidates with labour market information and training options. By integrating these tools, coaches empower candidates to explore suitable career paths confidently and strategically, making the transition smoother and more purposeful.  
 
LinkedIn Career Explorer is a dynamic tool that uncovers hidden career paths by mapping existing skills to thousands of roles.
Why It Matters:
Skill Mapping: Reveals a list of skills for a particular role and unexpected career paths by highlighting transferable skills and probability match.
Upskilling: Identifies missing skills and links to LinkedIn Learning courses, streamlining professional development
Networking & Jobs: Connects candidates to professionals in target roles and local job postings which help to increase a candidates LinkedIn profile and presence.
Strengths Finder:  Candidates often question their strengths – what are they good at or known for?  Have them check out this free survey to discover their character strengths, as a way to discover greater joy in living in alignment with themselves. Strengthen connections by applying what they’ve learned and helping them to answer the interview question – what's your greatest strength?  
 
OpportuNext uses Canadian Labor Market Information (LMI) to provide data-driven insights into job roles with strong growth prospects and competitive wages. By entering a current job title, users are presented with relevant career options, highlighting roles that match their skills and offer positive employment outlooks.  

Aug 9, 2025

41 min

Summary
 
In this episode, Iris and Jodi discuss the concept of Memento Mori, emphasizing the importance of recognizing our mortality to inspire action and live fully. Jodi shares her journey of creating the Four Thousand Mondays platform, which encourages people to seize the day and pursue their dreams. They also explore the challenges of caring for aging parents, the emotional complexities involved, and the lessons learned about life, death, and the importance of compassion. The conversation highlights the need to confront our fears and regrets, ultimately motivating listeners to live with intention and purpose.
 
Takeaways
Memento Mori encourages us to remember our mortality.
Counting the Mondays we have left can motivate us to take action.
We often delay our dreams, thinking we have more time.
Caring for aging parents can be both challenging and rewarding.
Facing regrets of omission is crucial for a fulfilling life.
Life is about making meaningful connections and experiences.
We should not shy away from discussing death and aging.
Self-compassion is essential when dealing with life's challenges.
Chapters
00:00 Introduction to Memento Mori and Life's Shortness
01:49 The Impact of Memento Mori on Life Choices
04:13 Personal Stories and Motivations Behind Memento Mori
07:07 Operationalizing Carpe Diem: Tips for Living Fully
10:05 Facing Fears and Regrets: The Importance of Action
12:48 Pre-Gret: A New Perspective on Regret
15:17 Living with Intention: Making Dreams a Reality
20:24 Embracing the Topic of Death
24:55 The Impact of Aging Parents
26:56 Navigating the Challenges of Caregiving
33:30 Reflections on Life and Death
38:07 Living Life to the Fullest
 
Resources
Connect with Jodi on Linkedin, Instagram, or her website, https://fourthousandmondays.com/.  
Book by Jodi Wellman: You Only Die Once: How to Make It to the End with No Regrets
Book by Irvin D. Yalom: Staring at the Sun: Overcoming the Terror of Death

Jul 31, 2025

47 min

Summary
In this episode, Iris engage in a deep conversation with Elena, who shares her journey of reinventing herself and starting a coaching business at midlife. They discuss the challenges and realizations that come with this transition, the importance of values in career choices, and practical tips for aspiring entrepreneurs. Elena emphasizes the significance of self-awareness, confidence, and the support of loved ones in navigating career changes and pursuing one's passions.
Takeaways
Elena started her coaching business to make an impact on others' lives.
Getting older brought a mix of confidence and realism for Elena.
Midlife is a time for reflection and potential reinvention.
Values play a crucial role in career decisions and fulfillment.
It's never too late to pursue a new career path.
Self-talk can significantly influence one's motivation and actions.
Building a supportive network is essential for success.
Starting small can lead to significant changes in life and career.
Embracing creativity can lead to unexpected opportunities.
Chapters
00:00 Reconnecting After Years07:18 Navigating Family Responsibilities10:13 Supporting Career Transitions13:56 Lessons from Career Coaching20:38 Letting Go and Rebuilding Identity25:27 Aligning Career with Values32:07 Starting a Business at Midlife41:14 The Journey of Entrepreneurship and Personal Growth
Resources
Book by by Andrea Fruhling and Norman Amundson: Career Wayfinder: Discovering your career through delightfully practical projects.
Podcast by Mjuriel Wilkins: Coaching Real Leaders
Connect with Elena on LinkedIn or through her website, Impact Career Coaching.
 

Jul 8, 2025

37 min

Summary
In this episode, Ana and Iris discuss the complexities of career changes, sharing personal stories and insights on recognizing the need for change, the use of vision boarding, and the role of support systems. They emphasize the significance of asking the right questions, experimenting with new paths, and embracing self-compassion throughout the journey. The conversation also touches on the Ikigai model and the barriers that often hinder career transitions, encouraging listeners to reflect on their own paths and aspirations.
 
Takeaways
Recognizing dissatisfaction is the first step to change.
Vision boarding can provide clarity on what you truly want.
Asking fundamental questions can lead to deeper insights.
Support from friends and coaches is invaluable during transitions.
Experimenting with new paths can uncover hidden passions.
The Ikigai model helps identify fulfilling career intersections.
Self-compassion is crucial when facing career challenges.
Comparison to others can hinder personal growth and happiness.
Reflecting on long-term happiness can guide career decisions.
Embracing the journey of self-discovery is essential for fulfillment.
Chapters
00:00 Navigating Midlife Career Changes06:07 Getting Unstuck: The Vision Board Experience15:56 The Role of Support Systems in Career Transitions20:08 Embracing the Messy Process of Discovery24:24 Design Thinking and Experimentation in Career Paths28:23 Understanding Ikigai: Finding Purpose in Work30:40 Overcoming Challenges in Career Change35:24 Reflection and Moving Forward
Resources
Book by Bill Burnett and Dave Evans: Designing Your Life: How to Build a Well-Lived, Joyful Life; Designing Your Life website
Book by Héctor García and Francesc Miralles: Ikigai: The Japanese Secret to a Long and Happy Life
Book by Timothy Clark, Alexander Osterwalder, Yves Pigneur, Bruce Hazen, and Alan Smith: Business Model You: The One-Page Way to Reinvent Your Work at Any Life Stage; Business Model You website

Episode 7: Divorce

Jun 18, 2025

Jun 18, 2025

29 min

Summary
In this episode, Ana and her guest and family lawyer Jonathan Bellamy, engage in a candid discussion about divorce, particularly in the context of midlife. They share insights on the legal aspects of divorce, the importance of prenuptial agreements, and the emotional challenges that often accompany the dissolution of a marriage. The conversation also touches on the evolving definitions of marriage, the stigma surrounding divorce, and practical advice for those considering separation. Throughout the episode, the importance of open communication and self-kindness is emphasized as essential components of navigating these life transitions.
Takeaways
Divorce can happen at any age, but midlife is common.
Understanding oneself is crucial during midlife and divorce.
Modern marriage has evolved beyond traditional definitions.
Prenuptial agreements are becoming more common and necessary.
Legal definitions of divorce involve separation and intention.
Stigma around divorce is decreasing but still present.
Emotions play a significant role in divorce proceedings.
Having hard conversations is essential for healthy relationships.
Clients often neglect to seek legal protection before marriage.
Self-kindness is vital during the divorce process.
Chapters
00:00 Introduction to Midlife Conversations04:27 Defining Modern Marriage09:46 The Importance of Prenuptial Agreements15:02 Legal Aspects of Divorce21:45 First Steps After Deciding to Divorce
Resources
Bellamy Law - Barrister & Solicitors https://lawyervancouver.net/ 
Legal Aid for people with low income: https://legalaid.bc.ca/ 
Family Law Act: https://www2.gov.bc.ca/gov/content/life-events/divorce/family-justice/the-family-law-act 

Jun 6, 2025

35 min

Summary
 
In this episode, Ana and her guest, Harjeet, discuss the complexities of breakups, exploring the emotional and biological impacts of relationship endings. They delve into the stages of grief associated with breakups, offering practical tips for healing and emphasizing the importance of social support. The conversation highlights the potential for personal growth and self-discovery that can arise from navigating the pain of a breakup, along with resources for further support.
 
Takeaways
Breakups are a form of social grief that can affect us deeply.
Understanding the biological response to breakups can help in healing.
Grief is not a linear process; it can involve moving back and forth between stages.
Having a solid social support system is crucial during a breakup.
It's important to recognize and articulate what support you need from others.
Writing down both the positives and negatives of a relationship can aid in healing.
Healing from a breakup involves addressing both the loss and any trauma from the relationship.
Self-awareness and reflection are key to personal growth after a breakup.
Therapy can provide a safe space to process emotions and experiences.
You will get through the pain and reconnect with yourself.
Chapters
00:00 Introduction to Breakups and Personal Growth07:49 Navigating the Stages of Grief13:33 The Role of Social Support in Healing23:58 Learning and Growth from Breakups29:03 Key Takeaways and Resources for Healing
Resources
Book by John Gottman Ph.D. and Nan Silver: What Makes Love Last?: How to Build Trust and Avoid Betrayal
Book by Sally Winston: Overcoming Anticipatory Anxiety: A CBT Guide for Moving past Chronic Indecisiveness, Avoidance, and Catastrophic Thinking
Book and TED Talk by Dr. Guy Winch: How to Fix a Broken Heart
TED Talk by Antonio Pascual-Leone: How to Get Over The End of a Relationship
Book by John Kim: Break Up On Purpose: A Catalyst for Growth
Book by Amy Chan: Breakup Bootcamp: The Science of Rewiring Your Heart

May 10, 2025

43 min

Summary
In this episode, Ana and Iris explore the complex theme of identity, particularly in the context of midlife. They discuss how identity evolves over time, the significance of cultural and personal narratives, and the challenges faced in reconciling past identities with present realities. The conversation emphasizes the importance of curiosity and self-acceptance in navigating identity changes, as well as the impact of identity on leadership and decision-making. They also share personal stories and recommend resources for listeners to further explore their own identities.
Takeaways
Identity evolves and changes throughout life.
Cultural identity can significantly impact self-perception.
Naming and acknowledging identity struggles is crucial for healing.
Curiosity about one's identity can lead to personal growth.
Leadership requires a shift from expert identity to facilitative roles.
Ethical decision-making is rooted in one's identity and values.
Understanding different dimensions of identity can enhance self-awareness.
Personal narratives shape how we relate to others and ourselves.
 
Chapters
00:00 Exploring Identity in Midlife10:39 The Dimensions of Identity17:42 Cultural Identity and Personal Narratives23:10 Embracing Our Past Experiences31:43 Ethical Decision Making and Identity36:41 Identity Revision and Personal Growth43:29 Resources for Identity Development
Resources
Book by Susan Cain: Quiet: The Power of Introverts in a World That Can't Stop Talking
Book by Sahaj Kaur Kohli (also founder of Brown Girl Therapy community): But What Will People Say. 
Book by Kenji Yoshino: Covering: The Hidden Assault on Our Civil Rights
Book by Najwa Zebian: Welcome Home: A Guide to Building a Home for Your Soul
 
 

Mar 29, 2025

38 min

Summary
In this episode, Iris and Ana explore the complexities of dating at midlife, sharing personal experiences and insights on growth, challenges, and the importance of mindset. They discuss the significance of approaching dating with intention, resilience, and authenticity, while also addressing common cognitive biases and societal narratives that can impact one's dating journey. The conversation emphasizes the value of self-discovery and compassion in building meaningful relationships.
Takeaways
Dating at midlife can be a journey of growth and self-discovery.
Approach dating with intention and resilience for a meaningful experience.
Mindset plays a crucial role in navigating the dating landscape.
Cognitive biases can distort perceptions of dating opportunities.
Authenticity is key to forming genuine connections.
Self-compassion is essential during the dating process.
Personal boundaries are important in maintaining one's values.
Investing in personal development can enhance dating experiences.
Flexibility in expectations can open up new opportunities.
Trust the process and be open to learning from experiences.
Chapters
00:00 Introduction to Dating at Midlife02:54 Navigating the Challenges of Dating06:03 The Positive Aspects of Midlife Dating11:11 Cognitive Biases and Dating Narratives15:24 Resilience and Personal Growth in Dating20:18 Investing in Yourself and Your Dating Journey22:58 Setting Boundaries and Authenticity26:53 Advice for Younger Selves30:56 Recommended Resources and Books35:50 Key Takeaways and Conclusion
 

Feb 22, 2025

29 min

In this episode, Ana and guest and Registered Clinical Counsellor, Fernanda Souza, explore family relationships and their impact on personal growth, behavioral patterns, attachment styles, topics important  during midlife and beyond. 
Key Topics:
Family of Origin:
Defined as the family you were born into, including cultural and national identity.
Influences include inherited values, unresolved traumas, and intergenerational wounds.
Midlife Reflections:
Midlife is seen as a prolific time for self-reflection and reevaluating family dynamics.
Revisiting personal identity and addressing unresolved issues with parents is common.
Attachment Styles:
Secure attachment develops through consistent parenting.
Inconsistent parenting or unresolved parental trauma can lead to attachment insecurities.
Adults can work on "naming and taming" their own attachment patterns to improve relationships.
Cutting Off vs. Maintaining Relationships:
Cutting ties with parents is sometimes necessary but does not always leads to healing.
Therapy can help clients explore ways to differentiate themselves from harmful dynamics while maintaining some connection, if feasible.
Healing often involves symbolic reconciliation rather than literal distancing.
Romantic and Parenting Relationships:
Family patterns, including attachment styles, influence adult relationships and parenting approaches.
Therapy helps individuals identify and adjust inherited behaviors that don't serve them well and stop intergenerational trauma.
Chapters
 
00:00 Navigating Adult Relationships with Parents
18:10 Understanding Attachment Styles and Their Impact
25:53 Resources for Healing and Growth
 
Related resources:
Books by Sue Johnson: Hold Me Tight, Love Sense
Esther Perel, Psychotherapist and New York Times bestselling author
Drs. John and Julie Gottman, The Gottman Institute
Connect with us:
Instagram: From Midlife to Best Life
 
Disclaimer: 
This podcast content is presented solely for general informational, educational, and entertainment purposes. It is not intended to substitute the advice of a physician, professional coach, psychotherapist or other qualified professional, diagnosis or treatment. Listeners should not disregard or delay in obtaining medical advice for any medical or health condition they may have and should seek the assistance of their healthcare professionals for any such conditions.

Feb 11, 2025

35 min

In this episode, Ana and Iris discuss the challenges and significance of forming, maintaining, and deepening friendships as adults, reflecting on their personal experiences and sharing practical insights.
Key Topics:
Challenges in Adult Friendships:
Midlife friendship challenges include time constraints, competing priorities, lifestyle differences, and the complexities of maintaining friendships during life transitions (e.g., marriage, parenting, or divorce).
Loneliness is highlighted as a growing epidemic with serious physical and emotional health implications.
Personal Insights:
Ana shares the importance of intentional friendships as an introvert, emphasizing quality over quantity.
Iris highlights the need for social connections as an extrovert, reflecting on how friendship plays a stabilizing role in her life.
The Role of Empathy and Intentionality:
Building meaningful friendships requires effort, including understanding friends' needs and love languages, engaging in difficult conversations, and being present for one another.
The episode emphasizes that friendships should align with personal values and provide mutual fulfillment.
Social and Emotional Value of Friendships:
Friendships are framed as an antidote to loneliness and a source of deep connection.
The hosts discuss how social prescriptions, like shared activities, can enhance well-being.
Practical Advice:
Suggestions include diversifying sources of emotional support, cultivating empathy, learning to have difficult conversations, and being intentional about nurturing friendships.
Reflection Questions:
On a scale from 1-10, 10 being the highest, rate your level of satisfaction on the friendships in your life right now. Are you happy with it? If not and if you would like to make it higher, what would you do? Where would you go about looking for new friends? Share in the comments as we'd love to hear from you.
Chapters:
00:00 Exploring Adult Friendships02:34 The Role of Friendships in Our Lives05:46 Challenges of Making Friends in Midlife08:44 Navigating Life Transitions and Friendships11:40 The Importance of Social Connections14:45 Being a Good Friend17:18 Empathy and Support in Friendships20:30 The Impact of Loneliness23:09 Lessons Learned About Friendships26:00 Final Thoughts and Reflections
Related resources:
The Roots of Loneliness Project
Book by Vivek Murthy, the 19th Surgeon General of the United States: Together: The Healing Power of Human Connection in a Sometimes Lonely World
Psychology Today article: 12 Ways to Make Friends in Mid-Life and Beyond
 
Connect with us:
Instagram: From Midlife to Best Life
 
Disclaimer
This podcast content is presented solely for general informational, educational, and entertainment purposes. It is not intended to substitute the advice of a physician, professional coach, psychotherapist or other qualified professional, diagnosis or treatment. Listeners should not disregard or delay in obtaining medical advice for any medical or health condition they may have and should seek the assistance of their healthcare professionals for any such conditions.

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