A first-person reflection from a Senior Scrum Master and Release Train Engineer on age, AI, and building something new.
I’m going to be honest with you in a way that most LinkedIn posts won’t be.
Since 1999, I’ve built my career in financial services, insurance, and staffing. I’m a tech enthusiast, family man, and passionate advocate for minimalist gear and Agile methodologies. With over a decade of Agile experience since 2011, I hold SAFe, CSM, and ICAgile Coach certifications. I have facilitated hundreds of standups, planned countless PIs, and coached teams through every imaginable challenge. My focus has always been on helping people collaborate and achieve more together.
And I’m watching AI make parts of that career obsolete in real time.
How I Got Here
I didn’t start in Agile. I was a business analyst first — requirements docs, stakeholder interviews, the whole waterfall playbook. When Agile started gaining traction, I made the jump to Iteration Manager (what most people now call Scrum Master). It felt right. Less documentation theater, more actually helping teams deliver.
Over the years, I moved into larger-scale work. Release Train Engineer. SAFe implementations. Enterprise transformations. The work was complex, political, and deeply human. I loved it.
Then the ground started shifting.
The Wake-Up Call
My former company dropped SAFe. Just like that. Years of building an Agile operating model, training teams, establishing cadences — and leadership decided to move to a hybrid Agile-Project Management model. It was frustrating, but honestly? Given how little leadership actually understood SAFe, it was probably the right call. You can’t run a framework that your executives treat like a checkbox.
But that’s not what kept me up at night. What kept me up was what replaced the conversations about Agile.
AI. Every meeting. Every Slack channel. Every town hall. AI this, AI that. And not in a “this is a cool tool” way — in a “this is how we’ll need fewer people” way.
I started paying attention. Not to the hype. To the pattern.
What AI Can Actually Replace (Let’s Be Real)
I’m not one of those people who thinks AI will replace Scrum Masters entirely. But I’m also not going to pretend nothing’s changing. Here’s what I see:
AI can handle:
- Sprint reporting and metrics dashboards
- Status updates and stakeholder summaries
- Meeting notes and action item tracking
- Backlog grooming suggestions based on historical data
- Risk identification from velocity trends
- Basically, anything that’s admin, documentation, or pattern recognition
AI can’t handle (yet):
- Reading the room when a team is about to blow up
- Navigating the politics of a reorg mid-sprint
- Coaching a new Product Owner who’s terrified of making prioritization decisions
- Building trust with a skeptical engineering team
- Knowing when to push and when to back off
- The messy, human, emotional core of what makes Agile actually work
The problem? Companies pay Scrum Masters and RTEs for the whole package. The admin work justifies the seat at the table. If AI eats the admin work, you better make sure leadership sees the value of everything else you do. And a lot of organizations don’t.
The Age Thing Nobody Wants to Talk About
I hear younger colleagues talk about AI with excitement. They should — they’ve got time to pivot, experiment, fail, and try again. When you’re 55, the math is different. I’m not panicking, but I’m not pretending it’s the same either.
There’s a pressure that comes with age in tech. It’s rarely said out loud, but it’s there. The assumption that you’re less adaptable. That you don’t “get it.” That the future belongs to people who grew up with a phone in their hand.
Here’s what I know: I’ve survived waterfall, survived the Agile transition, survived SAFe, survived the post-COVID remote work revolution. I adapt. That’s literally what Agile practitioners do. But I’m also realistic enough to know that adapting at 55 means I need to be more intentional about it.
So I’m Building Something
A few months ago, I started a side business. Not because I’m leaving Agile — because I refuse to let Agile leaving be something that happens to me.
I’m building a small tech company that sits at the intersection of everything I care about: AI, Agile methodology, and minimalist design. Digital templates for Scrum teams. AI-powered tools for practitioners. Curated tech products for people who like things clean and intentional.
Is it a side hustle? Yes. Is it a safety net? Also yes. But it’s more than that.
It’s a way to learn skills I never had to learn before — web development, e-commerce, digital marketing, content creation. At 55. Using AI as a tool, not fearing it as a replacement. There’s something poetic about using the thing that threatens your career to build your next one.
And honestly? I’m building it for my wife too. I want to create something that’s ours. Something that doesn’t depend on whether a VP somewhere decides to “restructure” my role out of existence.
What I’d Tell Other 50+ Agilists
If you’re in your 50s and working in Agile, here’s my unfiltered take:
1. Stop pretending you’re not worried. Everyone I talk to privately is thinking about this. The people who say “AI won’t replace us” are either selling certifications or haven’t been paying attention. It won’t replace the best of what we do — but it will shrink the market for mediocre facilitation and glorified project management.
2. Double down on the human stuff. Coaching. Conflict resolution. Organizational psychology. The skills that AI makes more valuable, not less. If your primary value is running ceremonies and updating Jira, you’ve got a problem. If your primary value is making dysfunctional teams functional, you’ve got a future.
3. Learn AI. Actually learn it. Not just read articles about it. Use it. Build something with it. I’m 55 and I’m using AI to generate content, create products, and automate parts of my business. It’s not as hard as you think, and the act of learning it kills the fear of it.
4. Build something on the side. I don’t care what it is. A blog. A product. A consulting practice. An Etsy shop. Something that’s yours, that uses your expertise, that doesn’t require someone else deciding you’re worth employing. The best time to build a lifeboat is before the ship starts sinking.
5. Your experience is an asset, not a liability. I’ve seen 14 years of organizational dysfunction. I know what actually works and what’s just Agile theater. No AI model has that context. No 28-year-old fresh out of a CSM course has that pattern recognition. Own it.
The Real Talk
I don’t know exactly what the Agile job market looks like in 5 years. Nobody does. Maybe AI augments our roles and makes us more effective. Maybe companies use it as an excuse to cut headcount and give remaining people AI tools instead of Scrum Masters. Probably both, depending on the company.
What I do know is this: I’m not going to sit around and find out.
I’m 55. I’ve got certifications, experience, and scars from a decade and a half of helping teams figure out how to work. I’ve also got a website, a product catalog, an Instagram account, and an AI assistant that helps me build things I never could have built alone.
The irony isn’t lost on me. I’m using AI to build a business because I’m worried AI might end my career. But maybe that’s not irony. Maybe that’s just adaptation.
And adaptation is what we do.
I’m a Senior Scrum Master and Release Train Engineer with 14 years in Agile. I’m building tools and templates for Agile practitioners at the intersection of AI and methodology. Follow along if you’re in the same boat.