Work Should Feel Good with Diana Alt

About Work Should Feel Good with Diana Alt

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.

Publisher

Diana Alt

Category

business · business

Language

en

Explicit

Yes

First episode

19 Feb 2025

Latest episode

27 Oct 2026

Latest episodes

76 episodes in the feed.

1. 

   27 Oct 2026

   Episode 75: Breaking the Career Rules and Building a Portfolio Career with Brandon Kenig

   What if the traditional career rules aren't actually rules? You don't have to stay in one lane, follow a linear career path, or keep your personal values separate from your professional life. In this episode, Diana Alt sits down with marketing leader and consultant Brandon Kenig to explore building a portfolio career on your own terms. Brandon shares how he's balanced corporate leadership, consulting, and civic involvement while challenging conventional career advice. They discuss creating career security beyond a full-time job, navigating professional reputation and personal values, and using transferable skills to move across industries. ⏳ Timestamps 00:00 Intro and meet Brandon Kenig 01:55 Travel, perspective, and learning from different cultures 09:19 Brandon's unconventional career path into marketing 14:01 Building a consulting business alongside full-time employment 15:54 Career disruptions and the importance of having a backup plan 19:45 Balancing civic engagement, political involvement, and corporate work 24:48 Managing professional identity and political visibility 27:33 Authenticity, personal values, and professional reputation 32:19 Separating political consulting from other business activities 36:31 Changing political affiliations and navigating professional consequences 40:09 Speaking publicly about values without sacrificing relationships 45:56 Breaking traditional career rules and challenging job-tenure expectations 48:11 Transferring skills and experience across industries 💡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 Brandon Kenig 🔗 LinkedIn → https://www.linkedin.com/in/brandonkenig 📲 Follow Brandon on Social Media: YouTube → https://www.youtube.com/@World-Unraveled-with-Brandon Facebook → https://www.facebook.com/brandon.kenig/ Instagram → @brandonkenig 📲 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. 

   13 Oct 2026

   Episode 74: How to Prepare for a Successful 2027 with Diana Alt

   Your 2027 success starts before January 1. Whether you're planning a job search, working toward a promotion, or growing a business, what you do in Q4 can make all the difference. In this solo episode of Work Should Feel Good, Diana Alt shares practical ways to prepare for the year ahead instead of waiting for New Year's resolutions to kick in. She breaks down three steps each for job seekers, professionals looking to grow within their companies, and business owners who want to make meaningful changes in 2027. From getting your resume and LinkedIn ready to building relationships, identifying career development gaps, and deciding what to stop doing in your business, Diana explains how to use the final months of 2026 to set yourself up for a stronger start. Why preparing for 2027 should begin in Q4 of 2026 How job seekers can clarify their targets, update their resumes and LinkedIn profiles, and reconnect with their networks How employees can identify growth opportunities, understand skill gaps, and build support for career advancement Why business owners need to work backward from their long-term goals to identify immediate priorities How eliminating or postponing certain activities in Q4 can create room for bigger opportunities in 2027 ⏳ Timestamps 00:00 Intro: Why your 2027 success starts in Q4 01:14 Job seekers: Build your strategy before launching your search 02:24 Define your target role and ideal work environment 03:43 Prepare your resume and LinkedIn for where you're going 04:46 Start networking and reconnecting with people now 05:44 Career growth: Prepare for promotions and new opportunities 07:00 Identify what you want and assess your development gaps 07:48 Talk to your manager and build internal advocates 09:23 Create a plan to close your skills and experience gaps 10:38 Business owners: Set up Q1 for long-term success 11:48 Diana's plans for business growth in 2027 12:46 Define your business goals and work backward 14:12 Choose Q4 priorities and decide what to stop doing 15:00 Make room for systems, support, and long-term growth 16:22 Why next year's success starts before January 1 💡 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 📲 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. 

   29 Sept 2026

   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 (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

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

2 ratings

Spotify

5.0 / 5

2 ratings

Contact Work Should Feel Good with Diana Alt

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.