Session #1: Living in an Easy World
A Coach's perspective on when technology promises freedom but delivers new forms of prison
Note: This article is written in the format of coaching note to reflect on how technology is changing the workplace and society in general. The client "Michael" is a fictional character, any resemblance to real individuals is purely coincidental.
Michael arrived fifteen minutes late, apologising profusely about back-to-back calls.
When I asked him to pause and breathe, he immediately launched into his familiar refrain:
“I wake up most mornings with the same feeling: this wall of tasks already pressing in before the day has started. My calendar is packed, my inbox overflowing, my head already rehearsing conversations I’ll never have time for.”
I let him continue, noting the physical tension in his shoulders as he described feeling “heavy, relentless, endless.” Then I offered a simple reflection:
“You’re describing the hardest life imaginable, yet you work in technology. Help me understand this contradiction.”
His whole posture shifted. A long pause. Then:
“This is actually the easiest world humanity has ever created, isn’t it? I can press a button and have a machine generate ideas, summaries, code, strategies. I can send messages across continents in seconds. Everything is faster, cheaper, smoother.”
Another pause.
“And I still feel crushed.”
Coaching Note
First breakthrough moment: recognising the paradox rather than staying stuck in the complaint.
When I asked what “being busy” meant to him, Michael’s response was immediate:
“It’s my shield. If I’m busy, then I’m important. If I’m busy, nobody can accuse me of wasting time.”
But as we explored this deeper, cracks appeared in his certainty.
“Actually, much of that busyness is theatre. I automate one process only to invent another. AI writes a draft and instead of using the gift of time to think, I decide I should produce more versions.”
He described last Tuesday’s client proposal:
“ChatGPT delivered something better than I could have written in twenty minutes. It should have taken me three hours. I should have felt victorious.”
His voice dropped.
“Instead, I spent the next two hours editing, second-guessing, adding unnecessary sections. By evening, Sarah found me still at my desk, tweaking fonts. When she asked what I was doing, I couldn’t give her an honest answer.”
The silence that followed was heavy with recognition.
Coaching Note
Client becoming aware of self-sabotaging patterns: creating busy work to avoid discomfort of efficiency.
I asked Michael about his relationship with the speed of modern communication. His answer revealed a deeper pattern:
“The faster I reply to emails, the more replies I get. The easier it is to create content, the more content is expected. Progress just sets a new baseline. What was miraculous yesterday is invisible today.”
He shared a story that clearly still bothered him:
“I was at dinner with my brother. He runs a small restaurant, works sixteen-hour days, real staffing problems. While he’s telling me about his struggles, I’m secretly asking my phone to draft responses to three clients. Within minutes, I had professional replies ready. I should have put the phone away and been present with him. Instead, I felt this compulsive need to send them immediately.”
Coaching Note
Technology enabling disconnection from relationships whilst creating illusion of productivity.
The conversation turned to choice paralysis. Michael described spending three hours yesterday watching YouTube videos about prompt engineering:
“I was convinced I was behind, that everyone else had figured out some secret I was missing. I took notes, bookmarked articles, added to my ever-growing learning backlog.”
Then his voice changed completely:
“My daughter knocked on my office door asking if I wanted to see the fort she’d built. I told her ‘just five more minutes.’ She waited. I never came. When I finally emerged two hours later, she was watching TV. The blankets were folded and put away. The fort was gone.”
The pain in his voice was unmistakable.
Coaching Note
The cost of endless optimisation: missing irreplaceable moments with family.
When I asked about his relationship with accomplishment, Michael revealed a fascinating conflict:
“When AI does something impressive, drafts an article, designs a process, I feel this flush of mastery. For a moment my competence has grown. Then the doubt creeps in. Was it me, or the machine? Am I really understanding or just performing understanding?
That gap unsettles me more than ignorance ever did. At least ignorance was honest.”
Coaching Note
Identity crisis around competence and authenticity in an AI-augmented world.
I asked Michael to reflect on what had changed in his life. His response was profound:
“In the past I could blame the system: not enough money, access, connections. Now those excuses are gone. What remains is me. If I don’t act, it’s not because I cannot. It’s because I chose not to.”
He described a recent example:
“Last month, I automated my entire invoice processing system. What used to take half a day now happens in minutes. I should have used those hours to work on the book I’ve been talking about writing for three years.”
His voice got quieter.
“Instead, I found myself refreshing Twitter, reading newsletters, having ‘strategic’ coffee meetings that led nowhere.”
At dinner with Sarah, he admitted:
“She asked about the book. I gave her the same excuse: ‘I’m just so swamped right now.’ The lie sat heavy between us. We both knew I had more time than ever. I just didn’t have the courage to face the blank page.”
Coaching Note
Client recognising how he’s using technology to avoid rather than enable meaningful work.
Near the end of our session, I asked Michael what he’d learnt about himself.
After a long pause, he said:
“I tell myself stories. That the inbox matters. That the meetings matter. That producing more documents proves my value. But what really matters is simpler: the courage to focus, the willingness to decide, the ability to act without waiting for permission.”
Then he surprised me:
“This morning, before our session, I deleted seventeen productivity apps from my phone. I closed twelve browser tabs about AI optimisation. I cancelled two meetings that were really just elaborate ways of avoiding real work.
It felt terrifying and liberating.”
Coaching Note
Spontaneous action before session suggests internal shift already beginning.
Session Summary
Michael is experiencing what I’m seeing with many high-performing professionals: the paradox of living in an “easy world” that somehow feels impossibly hard.
The external barriers to productivity and achievement have largely disappeared, leaving him face-to-face with the internal barriers he could previously avoid confronting.
Key insights that emerged:
Busyness as performance and avoidance rather than productivity
Technology enabling disconnection from relationships and meaningful work
Identity confusion around human versus AI contribution
Choice paralysis disguised as learning and optimisation
Using automation to create more busy work rather than space for important work
Next Session Goals
Explore what “meaningful work” looks like for Michael specifically
Develop practices for distinguishing between productive and performative activity
Create boundaries around family time that honour his values
Address the deeper fear of not being needed or relevant in an AI world
Final Note
Michael has rescheduled our next session twice: avoidance behaviour, but his deletion of apps suggests readiness for change beneath the resistance.