selfhelp – Surprised By Joy

“In the middle of every difficulty lies opportunity.” – Albert Einstein

In 2009 when I had to tell my parents that my husband and I had separated, I agonized over having the conversation. It meant that I not only had to manage my emotions about what was going on but also be prepared for theirs. It turned out to be a great conversation because I no longer needed to maintain a veneer that everything was okay.

I’m thinking about this conversation because I was just talking with the thought-provoking and inspiring blogger and retirement coach, Michelle Oram, about how to share life’s challenges on the How To Share podcast. She reminded me that when we share the difficult things we are going through, we open up ourselves to support.

In this podcast episode, Michelle shares her experiences and insights on how to navigate life’s challenges, particularly in sharing difficult news such as a cancer diagnosis. She discusses the importance of prioritizing who to share with, the emotional fatigue that can come from repeated sharing, and the value of support from both close friends and strangers. Our conversation also touches on the nuances of communication in personal versus professional contexts, and how these experiences shape our understanding of support and empathy. I also got to hear about Michelle’s new venture in retirement coaching, emphasizing the emotional aspects of transitioning into retirement.

Takeaways

Navigating life’s challenges requires thoughtful communication.
Prioritizing who to share difficult news with is crucial.
Sharing can open doors to support and help.
It’s okay to use different methods to communicate news.
Listening is more important than talking when supporting others.
People often don’t know what to say, so guidance is helpful.
Empathy grows from personal experiences with challenges.
Support can come from unexpected places.
Retirement can be a significant life change that requires preparation.

Here’s a short clip from our episode to give you a taste of the great conversation. Michelle’s comments about the power of open communication match my experience telling my parents about my breakup and more – when we share life’s challenges, it allows others to be able to support us.

Here are some ways you can listen and watch to the full episode:

The podcast player embedded below
Click this link to watch in a browser: How To Share Life’s Challenges with Michelle Oram
Subscribe to How To Share on Spotify, Amazon Music, or Apple Podcasts
Subscribing to the YouTube channel: https://www.youtube.com/@howtosharepodcast

Please listen, watch, provide feedback and subscribe.

48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive – The Life of Try: Personal growth, one try at a time.

What happens when you say “yes” to an adventure? Host Wynne Leon talks with tech entrepreneur and author Michael Yang about his memoir Coming Alive on the Ride and the way motorcycle travel became both a literal journey and a powerful metaphor for personal growth. Michael shares how stepping outside your familiar environment can help you hear “life’s invitation” to dream, venture, and rediscover what makes you feel fully awake.Together they explore resilience through the Korean concept of han—the accumulated weight of difficult circumstances—and how setbacks can become fuel for perseverance. Michael reflects on immigrating from Korea at 14, building a life through gratitude and hard work, and learning (again and again) that rejection doesn’t have to be the end of the story.From riding thousands of miles with a lifelong friend to a memorable run-in with Steve Jobs at Macy’s in 1982, Michael’s stories remind us that courage grows through companionship and curiosity. They also discuss the Korean guiding philosophy of Hongik—living in a way that benefits all humankind—and how our bravest tries can ripple outward in ways we may not expect.In this episode, we cover:Why “accepting the invitation” is simple—but the road rarely runs straightHow to tell the difference between healthy risk and avoidable dangerHan, perseverance, and turning setbacks into strengthThe immigrant mindset: gratitude, effort, and going for opportunityFriendship as a confidence builder—on the road and in lifeCuriosity, rejection, and holding onto a vision (plus the Steve Jobs story)Hongik: living for the wider benefit and making a positive dent in the worldWhether you’re craving a literal road trip or a fresh start at home, this conversation will nudge you toward your next brave yes.The Life of Try is a personal growth and self‑help podcast about getting unstuck, navigating uncertainty, and choosing to try—even when it’s uncomfortable, inconvenient, or not your idea.Hosted by Wynne Leon, the show explores how real growth, reinvention, and discovery often begin not with confidence or clarity—but with a single attempt. Through thoughtful interviews, reflective conversations, and real‑world case studies, each episode examines what it looks like to keep going when doubt shows up, plans fall apart, or life forces a change you didn’t ask for.This podcast is for anyone who:Feels stuck or uncertain about what’s nextIs navigating change, burnout, or reinventionWants to live more intentionally without pretending growth is easyBelieves progress starts by trying—again and againThe Life of Try isn’t about hustle or perfection. It’s about learning as you go, surfacing what matters, and sharing what you discover along the way.If you’re ready to surf the uncertainty, outlast the doubts, and step into your own try‑cycle, you’re in the right place.Links for this episode:48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive transcriptMichael Yang's websiteComing Alive on the Ride at Barnes & Noble, Amazon

Links for this episode:

Michelle Oram’s blog: Boomer Eco Crusader

12 things you should never say to someone with cancer – Boomer Eco Crusader

Best ways to support someone with cancer – Boomer Eco Crusader

Michelle Oram’s Second Life Vision retirement coaching