Why Do Most Programmers Who Start Companies Fail? Healthy Developer podcast

48:33

Ever thought about stepping into product management—just to try something totally different from engineering? Want expert guidance to grow? Apply for 1-on-1 tech career coaching with me . That’s exactly where Monte found himself. After years in dev and even engineering leadership, he made a move he thought would lead to more ownership and product vision. But once he was in the role… something felt off. In this coaching session, we unpack what actually happens when you chase product titles inside companies—and why the version you’re offered often isn’t what you imagined. Monte thought he was stepping forward. Instead, he realized he was just managing user stories and process artifacts. If you’ve ever wondered, “Is this really what the role is supposed to be?”—you’re not alone. You can also watch this episode on YouTube . Visit me at healthydeveloper.com…

Healthy Developer

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You Were Right About Healthy Developer 5:22

22 days ago5:22

5:22

You ever notice how sometimes the people around you see what’s really going on before you do? That’s what happened with this channel. I tried to go broad, help everyone in tech, chase what the “experts” and the algorithm said people wanted—but you knew better. You told me what made this channel special wasn’t the hype or some generic success formula. It was the real talk. The raw stories. The focus on staying healthy, sane, and actually living your life while you write code in an industry that rarely cares about either. In this episode, I’m owning up to where I lost the plot—and why I’m bringing it all back to what *actually* matters. We’re going deep on why “Healthy Developer” is the right home for this community (and for me), what’s staying, what’s changing, and what you can expect from here on out. If you’re here to argue or troll, you won’t like this one. But if you’re tired of the tech grind, and you want real strategies for staying grounded and growing as a developer *without* burning out, you’re in the right place. Thanks for holding me to a higher standard—and for helping me find my way back. Let’s build something better, together. You can also watch this episode on YouTube . Visit me at thrivingtechnologist.com…

Healthy Developer

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Helping a Dev Manager Fix Team Culture 50:34

29 days ago50:34

50:34

In this real coaching session, I talk with John, a developer-turned-manager, who’s navigating the messy middle of leadership. He’s caught between two teams, two continents, and shifting expectations. Sound familiar? We dig into: The difference between managing people and leading culture Why growth-stage teams break without intentional leadership How to lead without authority (especially when others outrank you) The startup → scale-up trap most companies fall into Ways to influence product direction by fixing culture first This is one of the most honest, practical coaching conversations I’ve had on team culture, dev leadership, and transitioning into management. If you're a senior dev or manager trying to scale impact without losing your soul, you’ll get a ton out of this. You can also watch this episode on YouTube . Visit me at thrivingtechnologist.com…

Healthy Developer

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Helping a Dev Double Down on Creativity 57:37

5 weeks ago57:37

57:37

Ever feel like tech work has turned you into a robot? Just crank out code, stay in your lane, and don’t ask too many questions? Yeah—same. → Find Out If You're Ready To Go Solo in Tech In this real, unfiltered coaching session, I work with Charlie—a creative technologist who’s been wrestling with how to bring *real* artistry back into his work. After running his own 3D animation business and helping other creatives thrive, he’s now stuck between paying the bills with soul-draining contracts... and figuring out how to build a career where he actually gets to make things that matter. We talk about time management, identity, and how hard it is to self-promote when your creativity feels personal. If you’re a developer or designer who’s ever wondered “How do I get back to making stuff I care about?”, this one’s for you. You can also watch this episode on YouTube . Visit me at thrivingtechnologist.com…

Healthy Developer

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Helping a Dev Rediscover His Entrepreneurial Drive 1:06:31

7 weeks ago1:06:31

1:06:31

Today, I’m sharing a real conversation I had with Matt—an experienced developer who’s been wrestling with where to take his career next. If you’ve ever felt like you’re stuck doing the same thing over and over, or like your potential is being wasted, this episode is for you. → Find Out If You're Ready To Go Solo in Tech Matt’s been on a journey to figure out what he truly wants, beyond just writing code. We dug into some deep topics—like whether he’s truly competitive, how to test his business idea, and finding clarity between stability and ambition. It’s a powerful session where Matt starts to rediscover his entrepreneurial drive and get real about what he wants to build. I think you’ll find a lot of takeaways you can apply to your own journey. You can also watch this episode on YouTube . Visit me at thrivingtechnologist.com…

Healthy Developer

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5 Signs You Shoulda Quit the Tech Grind YEARS Ago 17:44

8 weeks ago17:44

17:44

Ever feel like you're living in the tech job twilight zone? One minute you’re daydreaming about quitting, selling everything, and disappearing into the mountains. The next? You’re convincing yourself, “Eh… it’s not that bad.” Yeah—I’ve been there. → Find Out If You're Ready To Go Solo in Tech For years. I spent nearly a decade gaslighting myself out of leaving corporate life, ignoring burnout, and pretending I was just “in a rough patch.” But after coaching over 120 devs since going solo, I’ve learned this: most of us know we’re done. We’re just too skilled at lying to ourselves. So in this episode, I’m calling it out: Here are 5 signs you shoulda quit years ago—and 5 actions you can take right now to start your escape plan. No fluff. No "just follow your passion" nonsense. Just hard-earned lessons from someone who's been in your shoes—and walked out the other side. We’ll discuss: Why being too good at your job is actually a trap How apathy about tech might be a deeper signal The sneaky way your side projects are trying to tell you something What your unused vacation days really mean And why your coworkers’ loyalty is starting to feel cult-like You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:41) 1. 5 Signs You Should Have Quit Working in Tech Years Ago (1:53) 1.1 You're Too Good At Your Job (2:49) 1.2 You Stopped Caring About the Tech Stack (3:50) 1.3 Your Side Gigs are Your Real Job (5:01) 1.4 You're Hoarding Vacation Days (6:10) 1.5 You Get Annoyed By Other People's Loyalty (8:00) 2. 5 Immediate Actions to Start Breaking Free (8:25) 2.1 Quit Caring About Your Next Performance Review (9:45) 2.2 Sell Some Old Tech Gear (10:45) 2.3 Reclaim an Hour From Your Job (12:17) 2.4 Pitch a Fake Client Proposal (13:58) 2.5 Burn One Bridge of Responsibility (16:30) Tech Solopreneur Readiness Scorecard Visit me at thrivingtechnologist.com…

Healthy Developer

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Helping a Dev Manager Focus on Action—Not Fear 1:15:56

9 weeks ago1:15:56

1:15:56

Ever feel stuck in analysis paralysis, trying to figure out if you should go solo or stick with a stable tech job? In this live coaching session, I help Ben—a seasoned engineering manager and Agile coach—shift his focus away from fear and toward action. → Find Out If You're Ready To Go Solo in Tech We break down: Why even a stable tech job can still feel uncertain How fear of the unknown keeps devs stuck—and how to move past it The real way to test your next move without risking everything How to balance financial security with the drive for independence If you’re a developer, tech lead, or engineering manager who’s thinking about making a big career move but unsure where to start, this conversation is for you. You can also watch this episode on YouTube . Visit me at thrivingtechnologist.com…

Healthy Developer

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Loving Money Makes You a Perfect Programmer Slave 18:32

12 weeks ago18:32

18:32

Most people get into software development for the money—and hey, I get it. The tech industry can be insanely lucrative. But if your end goal is to break free from the corporate grind and work for yourself, could a high income actually be holding you back? Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community In this episode, I dive into my own career stories—when money was a good motivator, and when it turned me into a "perfect programmer slave." I’ve seen it all—from promotions I didn’t even care about to chasing startup dollars and, finally, finding freedom through coaching and serving others. You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:27) 1. How Loving Money Prevents Self-Employment (1:39) 1.1 Story: Early Raises (4:19) 1.2 Story: Starting Up to Cash Out (7:11) 1.3 Story: Starting Up to Serve (10:43) 2. 3 Ways to Find Freedom from High Income Dependence (11:18) 2.1 Reduce Monthly Expenses (13:10) 2.2 Focus Effort on Your Highest Value (14:44) 2.3 Quit Your Corporate Gig (15:10) Take the DevPathfinder Career Assessment (16:54) Join our Discord Community Visit me at thrivingtechnologist.com…

Healthy Developer

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Programmer Employees Don't Have a Career Anymore 11:15

13 weeks ago11:15

11:15

The days of stable employment in tech jobs as a career is over. I don't say this to scare you, but so you take some action to be less dependent on companies that couldn't care less about you! Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community In this episode, I share some of the latest developments in my time coaching over 120 software professionals. One of the biggest things I've learned, is that practically everyone is miserable. This year I have some exciting new announcements to make though - I'll be helping you escape the corporate grind! You CAN have a career in tech, but you have to step up, take more responsibility, and give up the delusion that corporate employment is a long-term strategy anymore. Those days sadly, are long behind us. You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (2:14) What I Told My Son about The Tech Industry (3:24) The Low-Value Career Death Trap (4:08) Employment is Now Maximum Risk (5:14) AI Has Made it Easier to Start a Business (6:45) Willful Ignorance Has Consequences (8:15) Temporary Employment is Honorable 9:16 Career Stability Is Possible Visit me at thrivingtechnologist.com…

Healthy Developer

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Stop Solving Problems for Your Development Team! 37:17

26 weeks ago37:17

37:17

Are you helping or holding your team back? In this episode, I explore why sharing technical answers with your development team might not be the best way to help them grow. Instead, learn how to use resourceful questions to empower your team members to think critically, solve problems independently, and build long-term confidence. This coaching strategy is rooted in co-active coaching principles and can transform how you mentor junior developers or lead your software team. Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community As a tech lead, manager, or mentor, it’s natural to want to provide answers when your team is stuck. But constantly solving problems for them can create dependency and stifle their growth. By shifting from a directive approach to a coaching mindset, you’ll help your team develop essential skills, foster ownership, and reduce your own workload in the long run. In this video, I’ll share practical examples and techniques you can start using today to guide your team effectively without always giving them the solution. If you’ve ever felt the pressure to be the “go-to expert” on your team, this episode will challenge that belief and show you a better way to lead. Coaching your team to solve their own problems not only benefits them but also makes you a stronger leader. Watch now to learn how to implement these strategies and take your leadership to the next level! You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:14) 1 Bringing Out The Best in Your Software Team (1:31) 1.1 Solving Problems For People Holds Them Back (2:48) 1.2 Let People Struggle (4:36) 1.3 The Role of Resourceful Questions (11:30) 1.3.1 Examples of Resourceful Questions (11:35) 1.3.1.1 "Have You Broken This Up Into Smaller Pieces?" (12:33) 1.3.1.2 "Have You Really Considered ALL Your Options?" (14:07) 1.3.1.3 "What if I Wasn't Available?" (15:09) 1.4 Shifting From Expert to Coach (22:36) 1.5 The Long-Term Benefits of Coaching (26:16) 2 How To Start Leading Like a Coach (26:48) 2.1 Start Small (28:50) 2.2 You Don't Need Formal Training (29:50) 2.3 Where to Start Coaching (30:02) 2.3.1 Code Reviews (31:08) 2.3.2 Design Reviews (32:46) 2.3.3 Project Planning (33:30) 2.3.4 Debugging Sessions (34:30) Get Help with Leadership Visit me at thrivingtechnologist.com…

Healthy Developer

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Can Employees REALLY Set Boundaries With Managers? 13:47

28 weeks ago13:47

13:47

Ever had a manager who expects you to be Superman? No matter what you do, they keep asking for "more, more, more." Earlier in my tech career, I thought it was my manager's fault. But when I learned the art of setting healthy boundaries at work, I realized that the power to push back was in my hands. Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community In this episode, I’ll share insights gained from working with over 20 software companies as a developer, architect, and management consultant on setting effective boundaries with managers. Getting this right can bring immense peace and prevent burnout. Without clear boundaries, it's easy to feel overwhelmed by unreasonable expectations—and the result is often exhaustion or even job burnout. Managers often respect employees who assert boundaries more than those who don’t. It may seem counterintuitive, but consider it: would you respect someone who allows themselves to be treated like a doormat? You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:20) Setting Boundaries with Your Manager (1:40) 1 Agree on Responsibilities for Your Role (3:13) 2 Determine Unacceptable Expectations (4:20) 3 Assign Consequences (6:17) 4 Communicate Your Boundaries (8:55) 5 Have a Backup Plan Visit me at thrivingtechnologist.com…

Healthy Developer

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Does Corporate Culture KILL Creativity in Tech? 17:44

30 weeks ago17:44

17:44

Are you a tech professional who feels your creativity is being stifled by corporate culture? In this episode, I explore the impact of corporate culture on creativity in the tech industry. I share my personal journey—from leaving behind my passion for music to embracing programming as a new creative outlet, only to find that corporate constraints in tech began to suppress my creative spirit. Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community I'll delve into how creativity in tech is often threatened by corporate environments that favor predictability over innovation. Discover why expressing creativity is vital for personal fulfillment and how the suppression of creativity can drain your energy. We'll discuss strategies to navigate tech workplace culture and reclaim your creative energy for your personal pursuits. Join the conversation about creativity suppression in tech. Have you experienced the stifling effects of corporate culture on your creativity? Share your stories and insights in the comments below. Let's work together to keep the flame of innovation alive in tech companies - and our personal lives! You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:11) A Story of Creative Loss and Redemption (3:24) 1 The Unmatched Value of Creativity (3:50) 1.1 Fueling Personal Fulfillment (4:36) 1.2 Enhancing Problem-Solving Skills (5:34) 1.3 Driving Innovation & Growth (6:53) 2 Navigating Corporate Constraints on Creativity (7:21) 2.1 Preference for Predictability (8:31) 2.2 Creatives Seen as Disruptors (9:37) 2.3 Leadership Suppressing Creativity (11:49) 3 Preserving Your Creative Energy (12:14) 3.1 Respect That Creative Energy is Finite (12:38) 3.2 Avoiding Creative Burnout (14:11) 3.3 Allocating Energy to Personal Pursuits Visit me at thrivingtechnologist.com…

Healthy Developer

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If Your Tech Job is Comfortable, You're in Danger 21:21

31 weeks ago21:21

21:21

Is your tech job feeling a little too comfortable? You might be unknowingly putting your career at risk. In the fast-paced world of technology, complacency can lead to career stagnation, limiting your earning potential and jeopardizing your job security. Grow Faster in Your Tech Career: https://thrivingtechnologist.com/coaching Join the Thriving Tech Community: https://thrivingtechnologist.com/community In this video, we'll uncover The Hidden Dangers of Comfort in Tech Jobs - How staying in your comfort zone can make you obsolete in a rapidly evolving industry. Signs You're Experiencing Career Stagnation - Recognize the red flags that indicate you're not growing professionally. The Importance of Continuous Skill Development - Why updating your skills is crucial for career advancement and remaining competitive. Strategies to Overcome Complacency - Practical steps to reignite your passion and drive in your tech career. Exploring Self-Employment and Tech Consulting - How becoming self-employed or starting a solo venture can enhance your career growth. Don't let the comfort of today become the regret of tomorrow. It's time to take control and ensure you're not left behind in the ever-changing technology industry. You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:29) 1 A Story of Me Getting Trapped (2:59) The Illusion of Security (5:00) 2 Signs Your Tech Job is Too Comfortable (5:26) 2.1 Lack of Learning (6:18) 2.2 Routine Work with Repetition (7:05) 2.3 No Networking (8:44) 2.4 Content with The Status Quo (9:25) 3 The Consequences of Complacency (9:45) 3.1 Career Stagnation (11:31) 3.2 Job Insecurity (12:12) 3.3 Reduced Earning Potential (12:30) 3.4 Missed Opportunities (13:19) 4 Solutions for Growth when You've Become Complacent (14:41) 4.1 Continuous Learning (16:50) 4.2 Skills Diversification (18:29) 4.3 Consider Self-Employment Benefits (19:28) Career Compass Tech Career Coaching Package Visit me at thrivingtechnologist.com…

Healthy Developer

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Think Your Corporate Job Is Secure? Think Again 24:40

33 weeks ago24:40

24:40

What if the real risk isn't leaving your corporate job, but staying in it? If you’re comfortable in your tech job today, layoffs aren’t the only risk you face. The myth of job security is a common cause for staying stuck and growing complacent. 7 years ago my life was turned upside down when I realized for the first time - just how trapped I’d become. I developed chronic insomnia and anxiety, and it eventually emptied my bank account. All because I refused to accept that I’d outgrown working for corporations. I wasn't sure if I wanted to be an entrepreneur or just work solo as a consultant - but I knew I was done with having a boss. In this episode, I’d like to help you get a sober view at what staying in corporate jobs can cost you. Unfortunately, job security is a myth. I hope this content about overcoming fear of self-employment helps you find the courage to explore more empowering ways of work - if you’ve outgrown the corporate tech job grind. Whether you want to become an independent software development consultant or start a SaaS (software as a service) business, tech professionals in IT jobs and at software companies don't have to stay chained to their corporate jobs forever. There is no such thing as a "secure job"! But you'll have to step into the unknown waters of being a solopreneur - if you want to experience self-empowerment. Join my Patreon: https://thrivingtechnologist.com/patreon Learn about one-on-one career coaching with me: https://thrivingtechnologist.com/coaching TechRolepedia, a wiki about the top 25 roles in tech: https://thrivingtechnologist.com/techroles The Thriving Technologist career guide: https://thrivingtechnologist.com/guide You can also watch this episode on YouTube . Chapter markers / timelinks: (0:00) Introduction (1:41) 1 The Lie of Corporate Stability (1:55) 1.1 Cognitive Biases (4:40) 1.2 Hidden Risks (6:38) 1.3 Opportunity Costs (9:19) 2 How Self-Employment Can Reduce Risk (9:31) 2.1 Diversify Income Streams (11:34) 2.2 Growth & Adaptability Mindset (16:42) 3 Overcoming Fear of Self-Employment (16:44) 3.1 Challenge Fear of The Unknown (19:31) 3.2 Embrace Risk as Opportunity Visit me at thrivingtechnologist.com…

Healthy Developer

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The Secret to Finding Profitable Software Ideas 13:55

34 weeks ago13:55