For years, productivity felt like a superpower.

It helped you earn more, save more, and move faster toward financial independence. It becomes part of your identity. The reason you feel like you’re “on track.”

But what happens when that same skill starts working against you?

As you get closer to FI, it becomes harder to tell the difference between productive effort and unnecessary optimization. And for many people, the habit of doing more doesn’t stop, even when they no longer need it.

In this episode, I talk with Doug Cunnington, host of Mile High FI, about the idea of “anti-productivity” or the intentional practice of doing less, not out of laziness, but out of clarity.

We explore why over-optimization can quietly reduce quality of life, how productivity can become a default identity, and what it actually looks like to step back without losing purpose or direction.

If productivity has been your edge on the way to FI, this conversation will help you rethink what comes next.

Key Takeaways:

• Why productivity can become a limitation after FI
• How over-optimization reduces joy and increases burnout
• The hidden fears that drive constant productivity
• Why many FI achievers struggle to slow down
• How to tell when effort stops producing meaningful returns
• What “anti-productivity” actually looks like in real life
• How to build purpose without constant optimization
• Why doing less is a skill, not laziness

Other Episodes You’ll Love:

Tiny Quits That Build Toward Full FI | E194 Jess, The Fioneers

The Hardest Skill in FI: Knowing When to Stop | E190 Joel Larsgaard

How to Create a 3-Day Workweek (Before You Reach FI) | E187 Andy Hill

Guest Summary:

Doug Cunnington is the host of Mile High FI and a financial independence advocate known for his practical, grounded approach to money and life design. Before reaching FI, Doug built a career centered around productivity, side hustles, and business building — skills that helped him achieve financial independence relatively early. Today, he focuses on helping others think more clearly about money, work, and lifestyle design, while also exploring what it means to step back from constant optimization and live with more intention.

Connect With Justin

Email me at [email protected] or connect with me on LinkedIn.

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