Ever thought about stepping into product management—just to try something totally different from engineering?

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.

Work with me: https://healthydeveloper.com

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.

Work with me: https://healthydeveloper.com

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.

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.

Work with me: https://healthydeveloper.com

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.

Work with me: https://healthydeveloper.com

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.

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.

Work with me: https://healthydeveloper.com

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

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

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

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

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