Helping a Dev Rediscover His Entrepreneurial Drive
Thriving Technologist
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. → 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...
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5 Signs You Shoulda Quit the Tech Grind YEARS Ago
Thriving Technologist
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. → 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...
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Helping a Dev Manager Focus on Action—Not Fear
Thriving Technologist
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. → 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...
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Loving Money Makes You a Perfect Programmer Slave
Thriving Technologist
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: Join the Thriving Tech 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...
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Programmer Employees Don't Have a Career Anymore
Thriving Technologist
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: Join the Thriving Tech 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,...
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Stop Solving Problems for Your Development Team!
Thriving Technologist
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: Join the Thriving Tech Community: As a tech lead, manager, or mentor, it’s natural to...
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Can Employees REALLY Set Boundaries With Managers?
Thriving Technologist
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: Join the Thriving Tech 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...
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Does Corporate Culture KILL Creativity in Tech?
Thriving Technologist
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: Join the Thriving Tech Community: I'll delve into how creativity in tech is often threatened by corporate environments that favor predictability over innovation....
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If Your Tech Job is Comfortable, You're in Danger
Thriving Technologist
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: Join the Thriving Tech 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...
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Think Your Corporate Job Is Secure? Think Again
Thriving Technologist
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...
info_outlineToday, 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