In this week’s episode of the Process Debt Podcast, we dive into a surprisingly profound Instagram clip of Steve Jobs, where he reflects on the transition from building Apple I computers in his garage to managing the scaled chaos of Apple II. The key lesson? When he was small, process enabled him. When Apple grew, process began to control him.

We explore the tension between bureaucratic processes that feel like relics of fear and risk avoidance—and enabling processes that empower people, clarify ownership, and get stuff done. From RACI matrices that look great on a slide but confuse everyone in practice, to home remodel projects that showcase clear accountability and outcome-based thinking, this episode is packed with stories and insights that will resonate with any leader navigating growth.

Other highlights:

• Why enabling processes don’t go viral (hint: there are no memes for smooth operations).
• How process debt shows up when boundaries disappear.
• Why "good fences make good coworkers."
• The coffee-making analogy you didn’t know you needed.
• And what knowledge workers can learn from contractors and construction sites.

Whether you're scaling a startup or trying to untangle legacy spaghetti in a big org, this episode reminds us: the best processes don’t call attention to themselves—they just quietly make life easier.

🎧 Tune in and, if you do find a meme about enabling processes… send it our way.

In this episode of Process Debt, we discuss how process transformation should adopt the mantra of "Buy vs. Try" and explore why so many organizations opt to "buy change" instead of building it from within. From billion-dollar consulting contracts to executives chasing quick wins, we unpack how outsourcing transformation often becomes a way to pass the buck rather than solve the problem.

We contrast this culture of buying with the power of "triers"—curious, connected employees who dig into the white space between processes, experiment, and leave a lasting impact. Along the way, we share stories of over-engineered solutions vs. $19 fixes, short-term career mindsets vs. long-haul investment, and why true change demands rolling up your sleeves, not just hiring the next McKinsey deck.

If you've ever wondered why "transformation" keeps getting sold instead of solved, this episode is for you.

Welcome to Process Ailments – Try vs. Buy, where we explore the aches and pains of business processes through the lens of personal wear and tear. This week, Toby's battle with "old man knee" becomes the perfect metaphor for what happens when organizations ignore their process health.

We kick things off with a laugh — is it a blood clot or just tight quads? — then dive into the deeper lesson: not every pain means disaster. Some are compound fractures (urgent breakdowns), but most are soft tissue injuries — nagging issues that worsen when ignored.

From there, we explore a core tension in modern organizations:

• Buy: The flashy, top-down push for new systems like SAP — expensive, visible, and often effective, but loaded with hidden rehab work that rarely gets addressed.
• Try: The gritty, everyday work of process rehab — subtle, high-value, and cheap, but often invisible and undervalued.

Why do we replace when we could repair? Why do we glorify the new while neglecting the maintenance? This episode is a call to rethink our instincts — in both our bodies and our businesses — and make space for the slower, less glamorous work that leads to long-term strength.

Process Debt: "Emotional Debt & the Cost of Consistent Connection"

This week on The Process Debt Podcast, Chris and Toby are coming to you live from the road, literally. With one host calling in from a pickup truck in southern Idaho and the other tuning in from Boise, the duo gets personal about an often-overlooked kind of process debt: emotional and constant connection debt.

In this unplugged and reflective conversation, they dive into:

• The toll of unmanaged personal processes and habits
• Why “white space” in your life is critical for performance and peace
• How nature, rest, and reflection can recharge your sense of purpose
• The illusion of balance vs. the power of prioritization
• Why doing only interest payments on your emotional debt leaves you empty
• How grinding through tasks without presence creates a false sense of progress

Chris shares his recent experience in the mountains with his daughter — a trip that left him exhausted but deeply alive. Toby opens up about learning to let go of the noise and rediscover the power of being rather than constantly doing.

If you’ve ever felt like you’re reacting more than you’re living, or like you’re paying emotional interest without ever touching the principal, this episode is for you.

Take a beat. Pay down the debt. Reconnect. Because rest isn’t the reward — it’s part of the process.

Discover how silent cultural cracks can bring down the biggest brands – before you see them coming.

In this episode, Chris and Toby dive deep into the concept of cultural debt – an often invisible but powerful form of process debt that can shape, elevate, or destroy an organization over time.

They explore:

• What cultural debt is and how it differs from process debt
• The hidden costs and risks of unchecked cultural norms
• Legendary company cultures: Google’s engineered elegance, Apple’s design obsession, Facebook’s “move fast and break things,” Zappos’ insane customer service, and Amazon’s pragmatic anti-PowerPoint stance
• How culture can degrade, using Enron and Wells Fargo as cautionary tales of moral decline
• The concept of cultural debt leading to black swan events, with Tesla as a live example of potential cultural implosion despite financial momentum
• Why culture is often an invisible ticking time bomb, where good habits and moral integrity matter as much as process efficiency

They argue that cultural debt isn’t inherently bad, just as process debt is, but left unmanaged, it can undermine the very foundations of business. The conversation weaves stories, strategic insights, and moral reflections, ending with the sobering reality that the more cultural debt accumulates, the higher the probability of catastrophic failure.

📝 Listen in to learn how to recognize, manage, and mitigate cultural debt before it becomes your organization’s undoing.

Get ready for a rewind to our March 21st episode, where we kicked things off with the latest drama between Trump and Musk – two fast friends turned quick enemies, with Musk seemingly taking the bigger hits this time around.

We then dove deep into the world of process debt, asking the hard question: Are the systems we rely on at work fundamentally broken? From ERP nightmares like SAP to hacked-together Atlassian setups, we explored why software becomes bloated, why RACI models often fail, and why adding fields or reports is easy but rarely wise.

If you've ever wondered:

• Why your workflow tools feel like a graveyard of good intentions,
• Why management demands reports no one uses,
• Or why software “vanilla” never tastes as sweet as promised…

…then this rewind is for you.

Tune in to hear Chris and Toby break down how process assumptions, poor system design, and magical thinking create organizational chaos – and why ignoring these debts won’t make the process fairies clean them up for you.

Where does your work live? If the answer is “everywhere and nowhere”—scattered across Slack threads, buried in email chains, lost in forgotten SharePoint folders—then this episode is for you.

In this episode of Process Debt, Chris and Toby unpack the messy reality of modern knowledge work and ask a provocative question: Is your work homeless? Together, they explore what it means for work to lack a consistent, discoverable home and how that contributes to chaos, confusion, and stalled productivity.

From shared drives that feel more like junk drawers to the false promise of “pretty” over “practical,” they dig into why clarity, structure, and ownership matter—and how to begin “cleaning your room” before trying to fix the whole house.

Whether you're a seasoned executive or a new hire still hunting for your team’s silverware drawer, this episode offers a candid, often funny, and ultimately hopeful conversation about how to give your work a proper place to live.

In this episode of Process Debt, Chris and Toby explore one of the most overlooked issues in modern business: the invisible constraints that shape our work as knowledge workers. Unlike physical jobs, where constraints are visible and immediate—think long lines or broken machinery—knowledge work is plagued by hidden bottlenecks, shifting priorities, and the chaos of constant context switching.

Together, they explore:

• Why visibility matters—and how invisibility in knowledge work kills productivity
• How post-COVID workplace structures misread productivity signals
• The cost of endless communication and the myth of “inbox zero”
• Context switching and the surprising stat that it takes 24 minutes to refocus
• What managers and ICs can do to reduce friction: tracking blocks, guarding time, clarifying priorities
• Why “planning at 100%” is a recipe for burnout
• Lessons from Drucker, Cal Newport, and some real-life team fails (and recoveries)

This episode is a conversation about how we work, why we get stuck, and what we can do—individually and as leaders—to make invisible constraints visible and manageable.

We’ve all been there—drawn in by a sleek SaaS website, hypnotized by animated walkthroughs, and convinced this tool will finally solve our team’s biggest pain points. But behind the glossy UI and clever branding? A clunky mess that no one wants to use.

You just got SaaS-fished.

It’s the business version of catfishing:

• The video showed elegant workflows.
• The reps promised seamless integrations.
• Your team expected a miracle.

And what did you get? 💸 A tool that doesn’t fit the use case 🤯 A confused, overburdened team 🚫 Zero adoption and sunk cost

🚩 Common Red Flags You’re Being SaaS-Fished:

• “Low-code / no-code / some-code” buzzwords
• Beautiful mockups that don’t match reality
• It promises to solve everyone’s problem
• Add-ons that double the total cost
• Integrations that should work—but don’t

💡 Prevention Checklist:

• Sandbox it. Never trust the happy-path demo.
• Get real users. Not just execs or IT buyers.
• Proof of concept. Spend some money to test before scaling.
• Process first. Don’t fix a tool problem when you have a workflow problem.
• Watch integration scope. APIs ≠ automation.

Let’s stop believing every tool will magically solve process debt.

The grass isn’t greener—it’s just better marketed. 🌱

We made it to episode 35—halfway to 70, not that it means anything… or maybe it does? In this episode, Chris and Toby take a raw, hilarious, and deeply practical look at what it really means to be “productive” in a modern knowledge economy that thrives on exhaustion and disconnection.

From cobblers and calendars to Cal Newport’s Slow Productivity, we break down:

• Why most productivity systems are lying to us
• The difference between projects and tasks, and why our brains don’t treat them differently
• The social pressure of busyness and how it feeds into the exhaustion Olympics
• The seductive appeal of working at a natural pace
• Why you should give yourself permission to do fewer things with higher quality—and how to actually do that

We also explore how to:

• Set boundaries that prioritize clarity over constant accommodation
• Shift from reactive task-juggling to intentional, project-focused work
• Stop letting other people’s urgency become your problem

This one’s for anyone who’s ever ended the day staring at a task list and wondering: Was I even productive?

Mentioned in This Episode:

• Slow Productivity by Cal Newport
• The “Inbox-first” trap
• The power of time blocking and the myth of urgency