AI is the fastest-growing plant of our times—it shoots up quickly and gives lush returns on the surface. But without proper pruning, care, and boundaries, its roots can overrun your garden.
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If you’re new here, welcome! Every week, we unpack leadership, mindset, and personal growth into something real and doable. Expect research-backed insights, a little storytelling, and practical ideas that actually fit into your life (even the messy parts).
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Today at a Glance
Why your top AI users are quietly burning out
What freelancers are doing differently (and better)
A proven fix to future-proof your Human+AI team
Looking for my library of 99 cheat sheets? You’ll find it at the end of the email!
This Week’s Sponsor
Today’s issue is sponsored by Upwork, the world’s work marketplace. Their new 2025 AI Productivity Report is one of the most eye-opening things I’ve read this year. It goes beyond the hype and dives deep into the real human impact of AI at work.
If you’re leading a team, I can’t recommend it enough. It’s sharp, clear, and packed with insights you can act on today.
[3-min read]
What Happens When AI Becomes Your Team’s Favorite Coworker?
AI has officially arrived.
77% of executives say they’re seeing real productivity gains
Employees using AI report being 40% more productive
That’s the good news.
The bad news?
Your best AI users—the top performers—are also the most burned out, disengaged, and twice as likely to quit.
Let that sink in:
88% report burnout
67% trust AI more than their coworkers
64% say they have a better relationship with AI than humans
They’re producing more… but at what cost?
This is the productivity paradox. And it’s happening inside companies of every size, in every industry.
To make this even more practical, I created an infographic in partnership with the Upwork Research Institute.
It breaks down the 6 hidden costs of AI productivity, and what you can do today to avoid them.
👇 Click for the PDF version and share with your team.
What Surprised Me Most as a CIO
As a former CIO, I’ve led tech transformations across global teams. I’ve seen the benefits of automation. But I’ve also seen the human toll when adoption outpaces design.
With AI, that risk is bigger than ever.
Here’s what stood out to me:
Strategy Disconnect
Top AI performers are often the ones most confused about how their work ties into company AI strategy. That’s a big red flag.Manager Pressure
Middle managers are the most productive AI users and the most burned out. They’re being squeezed from every angle—implementing new tools while still expected to lead with clarity and calm.
We’re not just adopting a new tool.
We’re rearchitecting how work gets done. And most companies haven’t caught up.
What Freelancers Are Doing Differently
Freelancers using AI are just as productive as full-time employees. But they’re thriving, not burning out.
Here’s what the research found:
88% say AI has positively impacted their careers
They use AI as a learning partner, not a replacement
They feel in control, not overextended
They’re focused on growth, not just output
In short: freelancers have figured out how to work with AI instead of becoming consumed by it.
It’s a model worth studying, and emulating.
6 Simple Fixes to Avoid the Burnout Spiral
Schedule “AI impact” check-ins
Make it a habit. Ask your team: What’s working? What’s draining you?Protect time for learning
Block out 2 hours/week for AI skill development. No guilt, no meetings.Start with human connection
Begin each week with a quick team huddle—before jumping into tools.Rebuild trust
Face-to-face brainstorms. Side-by-side problem-solving. Connection matters.Listen to your power users
Your best AI performers have insights leadership needs. Use them.Redesign workflows for Human+AI collaboration
Treat AI like a teammate. Define roles, expectations, and boundaries.
Ready to Lead the Human+AI Future?
AI isn’t going to slow down. But that doesn’t mean your people have to burn out.
The smartest leaders I know are designing flexible, high-trust, Human+AI teams that prioritize connection, growth, and performance.
If that’s your goal too, don’t miss Upwork’s full report.
Until next time, stay human, stay curious,
Justin
