Episode 11: Design Thinking for Your Career with Lindsay Oishi
Work Should Feel Good with Diana Alt
Release Date: 05/14/2025
Episode 29: Board, Exec, and Regular Resume Distinctions with Erica Reckamp
Work Should Feel Good with Diana Alt
Ever wonder how helpful generative AI really is for job seekers? In this episode of Work Should Feel Good, Diana Alt sits down with executive resume writer and job search advisor Erica Reckamp to unpack Erica’s brand-new 2025 research on generative AI resume feedback, this time, from the job seeker’s perspective. You’ll hear how Erica’s deep background in ghostwriting, storytelling, and executive branding shaped her view on what AI tools get right (and very wrong) about resumes. They also explore how different types of resumes from entry-level to board-level demand different...
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Episode 28: Marketing in a Trust Recession with Ryan Holck
Work Should Feel Good with Diana Alt
Can people really trust your brand? Here’s why they might not and what to do about it. This episode dives into how to create brand trust in a noisy, skeptical world. Ryan Holck, speaker, author, and founder of Distill Your Story, joins Diana to unpack how storytelling, micro-targeting, and authentic connection are the key to surviving what he calls “The Trust Recession.” Drawing from his two decades in marketing and his experience reviving a local brick-and-mortar business, Ryan shares the real reasons people aren’t buying (hint: it’s not your offer, it’s how you’re talking about...
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Episode 27: Are You Overqualified or Overselling? with Diana Alt
Work Should Feel Good with Diana Alt
Wondering if you're “too experienced” for the jobs you’re targeting? Here's how to reframe your story and get hired anyway. When you're mid-career and applying for roles that seem below your previous titles or scope, you might get hit with the dreaded “overqualified” label. But is it really about being overqualified or are you just overselling the wrong aspects of your experience? In this solo episode, Diana Alt unpacks the nuance between being overqualified and overselling. She shares practical strategies to help you reposition your experience, adjust your resume and language, and...
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Episode 26: Own Your Brand, Own Your Career with Mike Kim
Work Should Feel Good with Diana Alt
Your personal brand isn’t just for influencers, it’s your career superpower. Learn how to stand out with authenticity and strategy. In this insightful conversation, Diana Alt sits down with branding expert and author Mike Kim to explore how owning your personal brand can elevate your career. Mike shares his unconventional path from church music director to Wall Street Journal and USA Today bestselling author and how authenticity, strategy, and storytelling shaped his journey. They dive into the power of having a public-facing identity, why your good work alone won’t get you noticed, and...
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Episode 25: GenAI Resume Feedback for Job Seekers Study Breakdown with Diana Alt
Work Should Feel Good with Diana Alt
Think GenAI is helping your resume? It might actually be hurting it. Let’s talk. What happens when job seekers turn to generative AI to review their resumes? In this solo episode, Diana breaks down a brand new study by elite resume writer Erica Reckamp that analyzed eight top GenAI tools, ChatGPT, Claude, Copilot, Gemini, Perplexity, Meta AI, Grok, and DeepSeek to see how helpful (or harmful) their resume feedback really is. Spoiler alert: it’s not all good news. Diana shares key insights from the study, including which tools gave the best and worst feedback, how AI sometimes hurts strong...
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Episode 24: How to Bring Your Thing to Life with Terry Weaver
Work Should Feel Good with Diana Alt
The world needs your thing and you need the right people to help make it real. What if that dream you've been carrying for years isn't random, but necessary? In this inspiring episode of Work Should Feel Good, I talk with Terry Weaver, speaker, coach, author, and founder of The Thing, an event series for creatives and entrepreneurs who are ready to turn big ideas into reality. Terry shares his powerful journey from teenage preacher to music industry insider to thriving entrepreneur and community builder. We discuss the importance of childlike wonder, side quests, and why intentionally building...
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Episode 23: 4 Cornerstones of an Aligned Career with Diana Alt
Work Should Feel Good with Diana Alt
Why not hating Mondays shouldn’t be a fantasy + how to know when your job is the real problem In this first-ever solo episode, Diana peels back the curtain on the story behind the name Work Should Feel Good and explains what it actually means. She shares the core philosophy of her coaching practice and introduces the Aligned Career Cornerstones, a practical, powerful framework to help you determine whether your current job is really working for you. If you’ve ever asked yourself: “Is this job even right for me?” “Do I have to hate work to make a living?” “Am I the...
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Episode 22: Fuel Your Career with Intentional Relationships with Tamara Copple
Work Should Feel Good with Diana Alt
Discover how community and connection can ignite your career path In this inspiring episode of Work Should Feel Good, I sit down with Tamara Copple, keynote speaker, community leader, and Product Owner at Children International to explore how intentional relationships can radically change your professional trajectory. Tamara shares her journey from a dead-end, toxic job to becoming a dynamic force in Kansas City's tech and nonprofit communities. We talk about the moment that sparked her transformation, how she found community through Kansas City Women in Technology, and why showing up, helping...
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Episode 21: Finding Joy After Loss with Rebecca Sabogal
Work Should Feel Good with Diana Alt
Can you rebuild your life and career after unimaginable loss? Rebecca Sabogal says YES and she’s living proof. In this deeply moving episode of Work Should Feel Good, I sit down with Rebecca Sabogal, founder of Performance Improvement Consultants to explore how joy, calling, and career can still thrive after life-altering grief. We talk about operational excellence, multicultural community building, and how her early experiences at Missouri S&T sparked a lifelong journey of strategy, service, and impact. Rebecca shares her story of becoming a young widow and mother while caregiving...
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Episode 20: How to Get Promoted Without Ruining Your Life with Jeff Mockaitis
Work Should Feel Good with Diana Alt
What does it really take to climb the corporate ladder without losing your soul in the process? This episode is packed with insight for thoughtful professionals ready to lead without burning out. In this candid conversation, Diana Alt sits down with Jeff Mockaitis, General Manager at Rahn USA Corporation, to explore how strong leadership is rooted in reflection, strategic risk-taking, and long-term thinking, not just doing more, faster. Jeff opens up about his unexpected path from chemistry lab work to executive leadership, the game-changing power of an MBA, and how embracing his top...
info_outlineFeeling stuck in your career? Learn how to use design thinking to unlock your next move!
Ever wonder how some people seem to navigate career transitions with clarity while others feel lost in a fog of indecision? In this episode, I sit down with Lindsay Oishi, Ph.D., Senior Product Manager at Indeed and design thinking educator, to explore how to apply the principles of design thinking to your own life and work.
We unpack why so many people lack intentionality in their careers, how fear holds us back from making change, and the difference between drifting and making empowered decisions. Lindsay shares stories from her time at Stanford, how her research influenced the best-selling book Designing Your Life, and why reframing your problems can lead to unexpected solutions.
Whether you’re craving more autonomy, looking for clarity in the chaos, or just tired of feeling like your job is happening to you, this conversation is your next right step.
⏳ Timestamps:
01:00 Meet Lindsay Oishi
02:15 Why people aren’t intentional about their careers
06:05 Intentional vs. accidental career moves
13:09 How fear and drifting affect decision-making
16:10 What is design thinking (and why it matters)?
22:12 Applying design thinking to your career
25:50 Lindsay’s research on the “Designing Your Life” course
29:30 Building emotional resilience and career agency
34:00 Toolkit mindset: design thinking and beyond
38:15 How Diana and Lindsay use their strengths in coaching
💡 Take action
🔥 Subscribe for future episodes → https://www.youtube.com/@dianaalt
📖 Grab my Resume Don’ts Guide → https://www.dianaalt.com/resumedonts
❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com
🚪 Wondering if it’s time to walk away? → https://www.isittimetowalk.com
💼 Work with me → https://www.dianaalt.com
📢 Connect with Lindsay Oishi
🌐 Lindsay’s Website → https://www.lindsayoishi.com
🔗 LinkedIn → https://www.linkedin.com/in/lindsayoishi
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