Work Should Feel Good with Diana Alt

Diana Alt
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Work Should Feel Good is the no-BS career podcast for people who want more from their work, without selling their soul to get it. Hosted by career strategist and layoff survivor Diana Alt, this show shares real stories, mindset shifts, and practical strategies to help you grow your career on your terms. You'll hear from recruiters, entrepreneurs, leaders, and everyday professionals in episodes that drop most Wednesdays. Let's make work feel good - together.

  1. Sep 29

    Episode 73: Leadership, Change, and Getting Things Done with Jon Umstead

    What can leaders and business owners learn from moonshiners? More than you might think. Jon Umstead has spent more than 30 years leading teams and organizations, from startups to Fortune 500 companies, in roles ranging from COO and CMO to transformation leader. In this episode, Jon and Diana reconnect after working together more than 17 years ago to talk about leadership, navigating change, entrepreneurship, and why getting things done often means keeping things simpler than we make them. Why reaching out and making the ask can create unexpected opportunities Building a career around curiosity, variety, and knowing yourself What leading through organizational change and M&A can teach you Why process for the sake of process creates unnecessary complexity Treating people like people as a foundation for effective leadership Why plans need to change when reality changes Using volunteer and board service to build new skills What moonshiners and bootleggers can teach businesses about distribution and innovation How entrepreneurial thinking can exist inside large organizations Why leadership doesn't require direct reports ⏳ Timestamps 00:00 Meet Jon Umstead and why making the ask matters 06:09 Against the Grain and Jon's new book 07:50 From corporate executive to mobile tap business 10:51 Building a career around variety and curiosity 15:03 Lessons from organizational change and M&A 20:51 Why business problems are more alike than we think 23:08 Where leaders create unnecessary complexity 26:31 Why leadership starts with caring about people 28:59 Growing from leading small teams to large organizations 34:05 Building experience through board service 40:44 Business lessons from moonshiners 43:34 What bootleggers can teach us about distribution 49:13 Entrepreneurial thinking without starting a business 50:46 How to spot a genuinely entrepreneurial workplace 54:05 Bringing real-world leadership experience into teaching 55:24 Rethinking what leadership needs to look like 57:39 Where to find Jon and Against the Grain 💡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 Jon Umstead 🌐 Website → champaignshine.com 🔗 LinkedIn → https://www.linkedin.com/in/jonumstead/ 📲 Follow Jon on Social Media: Facebook → https://www.facebook.com/champaignshine Instagram → https://www.instagram.com/champaignshine X → https://x.com/jonumstead Against the Grain: Business Lessons From the Still by Jon Umstead → https://www.amazon.com/dp/B0H6G8VMCS 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  2. Sep 22

    Episode 72: How to AI-Proof Your Job Search and Career with Jeremy Schifeling

    AI is changing how companies hire, but trying to beat AI with more AI isn't the answer. Diana talks with Jeremy Schifeling, founder of The Job Insiders and author of Unbreakable, about the human skills that matter most, how to build trust in your job search, and how to use AI without losing what makes you valuable. Why human skills matter more in the age of AI How referrals build trust in a job search Creating a high-trust resume What job seekers get wrong about AI How recruiters, sourcers, and hiring managers evaluate candidates Using AI to strengthen your career instead of automating your job search ⏳ Timestamps 00:00 Intro and meet Jeremy Schifeling 07:11 From education to marketing and tech 16:37 The skills becoming more valuable because of AI 22:56 Empathy and human connection as career advantages 27:35 Why referrals and trust matter 33:33 How to AI-proof your job search 36:13 Building a high-trust resume 40:19 What job seekers get wrong about AI 43:31 How hiring actually works behind the scenes 46:49 Why LinkedIn matters in recruiting 55:35 Using AI to explore your career 57:00 Staying relevant as AI changes work 01:02:00 Jeremy's book and closing advice 💡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 Jeremy Schifeling 🌐 The Job Insiders →https://www.thejobinsiders.com/?utm_source=chatgpt.com 🔗 LinkedIn →https://www.linkedin.com/in/schifeling/?utm_source=chatgpt.com Unbreakable: How to AI-Proof Your Job Search, Career, and Future → https://www.thejobinsiders.com/unbreakable?utm_medium=email&utm_campaign=signature&utm_source=chatgpt.com NY Fed employment data→ https://www.newyorkfed.org/research/college-labor-market?utm_source=chatgpt.com#--:explore:outcomes-by-major Free LinkedIn Profile Makeover→ https://www.thejobinsiders.com/profile?utm_source=chatgpt.com AI + LinkedIn Training for Career Leaders → https://www.thejobinsiders.com/linkedin-for-colleges?utm_source=chatgpt.com 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  3. Sep 15

    Episode 71: How to Stop Being the Bottleneck at Work with Adrienne Dorison

    Diana talks with Adrienne Dorison about building teams and businesses that don't depend on one person to keep everything moving. They explore better delegation, decision-making, and how leaders can give people the autonomy to do great work. Teaching people how to think, not just what to do Building better judgment and decision-making Using vision and values as decision-making tools Reducing owner and leader dependency Delegating decisions, not just tasks The IPO framework: Information, Permission, and Outcome ⏳ Timestamps 00:00 Meet Adrienne Dorison 02:41 From wildlife ecology to business consulting 14:19 Adrienne's safari guide experience 21:45 Teaching people how to think 29:21 Developing better judgment 32:21 Vision, values, and decision-making 38:22 What executive titles really mean 45:15 Removing owner dependency 50:53 Letting go of client work 01:06:00 Delegating decisions, not just tasks 01:08:27 The IPO framework 01:14:46 When work keeps coming back to you 💡 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 Adrienne Dorison 🌐 Level 11 Leaders → https://level11leaders.com 📲 Follow Adrienne on Social Media: 🔗 LinkedIn → https://www.linkedin.com/in/adriennedorison Facebook → https://www.facebook.com/adrienne.dorison Instagram → https://instagram.com/adriennedorison Threads → https://www.threads.com/@adriennedorison 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  4. Sep 8

    Episode 70: How to Build Genuine Human Connection in the Age of AI with Jim Morris

    As AI becomes part of everyday work, genuine human connection matters more than ever. Diana talks with Jim Morris, author of Connect or Die: How to Survive AI, about building stronger relationships through curiosity, integrity, vulnerability, and a willingness to help without making every interaction transactional. Building relationships without transactional networking Why authenticity matters more in the age of AI Using curiosity and vulnerability to create connection Building relationships across teams and industries Knowing when and how to communicate effectively ⏳ Timestamps 00:00 Why human connection matters in the age of AI 02:09 How relationships led Jim to a Times Square billboard 09:12 Being willing to ask and hear no 13:42 Jim's origin story and the power of relationships 21:11 Networking without being transactional 28:36 Authenticity instead of performance 37:29 Staying human in the age of AI 44:18 Genuine connection vs. performative success 48:49 How you show up when the stakes are high 55:38 Communication, timing, and consideration 01:00:23 Jim's books and final thoughts 💡 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 Jim Morris 🌐 Jim Morris → realjimmmorris.com 🌐 Connect or Die → connectordiebook.com 🌐 Human Touch Publishing → humantouchpublishing.com 🔗 LinkedIn → https://www.linkedin.com/in/realjimmorris/ 📲 Follow Jim on Social Media: YouTube → https://www.youtube.com/@impacteffectpodcast Facebook → https://www.facebook.com/therealjimmorris Instagram → https://www.instagram.com/realjimmorris/ 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  5. Sep 1

    Episode 69: How Great Leaders Build Teams That Don't Need Them with Ian Ng

    What happens when your leadership gets tested and your team suddenly has to function without you? Ian Ng joins Diana to talk about his transition from individual contributor to manager and how unexpected triple bypass surgery put his approach to leadership to the test. They explore delegation, self-sufficient teams, boundaries, and why making yourself indispensable isn't necessarily good leadership. Transitioning from individual contributor to manager Building a team that can function without you Delegating and letting go of work you've always owned Protecting PTO and creating healthier work boundaries What heart surgery taught Ian about leadership, time, and accepting help ⏳ Timestamps 00:00 Intro and meeting Ian Ng 05:15 Ian's path into corporate IT 11:00 Simpler solutions and avoiding overthinking 18:53 Moving from individual contributor to manager 25:42 Trust, accountability, and follow-up 27:04 Six days to prepare for heart surgery 30:09 Documentation, delegation, and preparing the team 40:35 Building a team that can function without you 46:24 Returning to work and leading differently 52:11 Learning to accept help 59:25 The value of time, attention, and life outside work 01:05:24 The worst career advice Ian ever received 💡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 Ian Ng 🌐 Website → iantng.com 🔗 LinkedIn → https://www.linkedin.com/in/ian-ng-4843602/ 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  6. Aug 25

    Episode 68: Reinventing Your Career Without Starting Over with Karen Spies

    Diana sits down with brand strategist, entrepreneur, and Second Wind Women podcast host Karen Spies for a candid conversation about career reinvention, entrepreneurship, and the messy moments that push us toward change. They explore why your experience comes with you into a new chapter, why entrepreneurship isn't necessarily the easier path, and how sometimes moving forward means moving sideways or even backward. Why career reinvention after 40 isn't starting over Bringing your existing skills into a new career Why the career ladder is more like a rock wall The realities of leaving corporate life for entrepreneurship How messy turning points can lead to meaningful change Building relationships and community through podcasting ⏳ Timestamps 00:00 Meet Karen Spies and Second Wind Women 04:19 Why Karen started her podcast 08:01 Entrepreneurship, loneliness, and connection 19:03 The stories hiding behind people's careers 28:51 Embracing the messiness behind reinvention 38:26 Why changing careers after 45 isn't starting over 39:44 The career ladder is really a rock wall 41:17 Leaving corporate life and the golden handcuffs 46:08 The realities of entrepreneurship 55:20 Finding community after leaving corporate life 01:09:39 Knowing when it may be time to leave 💡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 Karen Spies 🌐 Spiezz Digital → https://spiezz.com/ 🌐 Second Wind Women → https://secondwindwomen.com/ 🔗 LinkedIn → https://www.linkedin.com/in/karenespies/ 📲 Follow Karen on Social Media: YouTube → https://www.youtube.com/@SecondWindWomen Facebook → https://www.facebook.com/karen.spies1 Instagram → https://www.instagram.com/kuniguenda/ 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  7. Aug 18

    Episode 67: Winning Survivor Wasn't The End with Todd Herzog

    Todd joins Diana to talk about the unexpected career path that took him from movie theaters and Disney to working as a flight attendant, winning Survivor: China, rebuilding his life after alcoholism, and eventually discovering an artistic talent he didn't know he had until his 30s. Today, he and his husband create custom artwork through Todd's Pop Shop, a business Todd built around creativity, community, and doing work in a way that actually works for him. Todd also gets candid about what it means to start over when you feel like you've failed, why setbacks don't erase everything that came before them, and how deliberately looking for things worth celebrating helped him change the way he saw himself and his life. Todd's career before and after Survivor What winning Survivor did and didn't change Recovery, resilience, and starting over Discovering art during COVID Turning Todd's Pop Shop into a creative business Why it's never too late to try something new ⏳ Timestamps 00:00 Meet Todd Herzog 03:48 Movies, Disney, and early career 09:48 Becoming a flight attendant and applying for Survivor 12:37 Why Todd knew he could play the game 21:36 What people get wrong about Todd after Survivor 25:40 Life after winning Survivor 29:40 Alcoholism, recovery, and starting over 41:14 Discovering art during COVID 45:20 Building Todd's Pop Shop 56:33 Moving through setbacks and shame 01:03:06 Career advice and why it's never too late 💡 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 Todd Herzog 📘 Facebook → https://www.facebook.com/rockthezog 📸 Instagram → https://www.instagram.com/toddspopshop ❌X/Twitter → https://www.threads.com/@toddherzog 📧Emai  →  toddpopshop@gmail.com 📲 Follow Me On Social Media LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

  8. Aug 11

    Episode 66: The Comeback That Changed Everything with Terry Weaver

    What happens when life completely derails the plan and forces you to rethink how you work, lead, and let other people help? Terry Weaver returns to Work Should Feel Good to share how a sudden case of sepsis landed him in the ICU just as The Thing was beginning. Diana and Terry talk about the community that stepped in to keep the event going, his long recovery, and how the experience changed his thinking about rest, legacy, leadership, and building work that doesn't depend entirely on you. When your plans get derailed by a major life event Building a community that can step up when you can't Making rest part of the work Legacy, leadership, and letting other people help Redesigning work around your strengths and energy Choosing yourself instead of always choosing the safe path ⏳ Timestamps 00:00 Terry returns to Work Should Feel Good 02:28 When life changed in the middle of The Thing 05:47 Sepsis, septic shock, and the ICU 12:21 The community steps in 16:10 Rethinking legacy 20:59 The long road back 32:15 Redesigning work around energy and alignment 40:29 Why rest is part of the work 45:42 Letting other people lead 54:45 What does it take to pick yourself? 01:01:50 Why Terry doesn't want to build alone anymore 💡 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 from your job? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com 📢 Connect with Terry Weaver 🌐 Website → https://terryweaver.com/ 🔗 LinkedIn → https://www.linkedin.com/in/terrytheweaver 📺 YouTube → https://www.youtube.com/terryweaver 📘 Facebook → https://facebook.com/terryweaver 📸 Instagram → https://www.instagram.com/terrytheweaver 📲 Follow Me LinkedIn → https://www.linkedin.com/in/dianakalt YouTube → https://www.youtube.com/@dianaalt Facebook → https://www.facebook.com/dianakalt TikTok → https://www.tiktok.com/@thedianaalt

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5
out of 5
2 Ratings

About

Work Should Feel Good is the no-BS career podcast for people who want more from their work, without selling their soul to get it. Hosted by career strategist and layoff survivor Diana Alt, this show shares real stories, mindset shifts, and practical strategies to help you grow your career on your terms. You'll hear from recruiters, entrepreneurs, leaders, and everyday professionals in episodes that drop most Wednesdays. Let's make work feel good - together.

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