From Palm Pilots to AI: How Technology and Time Blocking Drive Productivity for Leaders

In my nearly 30 years of entrepreneurial leadership, one central theme has consistently driven my success: the pursuit of productivity. From my early days as an Executive Pastry Chef to leading a publicly traded cannabis company and now running my own consulting firm, staying organized and efficient has been critical to navigating the challenges of leadership.

It all started with a Palm Pilot.

Early in my career, I worked alongside Chef Thomas, an executive chef from East Berlin. He was a model of precision and organization, always a few steps ahead of deadlines and projects. His secret? It wasn’t just his East Berlin efficiency or an exceptional memory—it was his Palm Pilot. Chef Thomas introduced me to the concept of leveraging technology to stay organized and productive. That day, he shared how he managed his tasks, projects, and deadlines with the help of his trusty device.

His philosophy was simple yet transformative: “Renegotiate a promise before it’s missed.” This idea has stuck with me, shaping the way I lead and manage my time to this day.

Fast forward to today, and the tools have changed, but the principles remain the same. The evolution from Palm Pilots to AI-powered productivity apps like Motion has revolutionized how I approach my day. Here’s how I make it all work.

The Tools That Keep Me on Track

1. Remarkable Paperless Tablet
   My go-to device for outlining ideas and staying focused is my Remarkable tablet. Its simplicity—black and white display, lack of notifications—keeps me engaged without distractions. For someone like me, with an ADHD brain, it’s a game-changer. When I’m brainstorming or outlining a blog post (like this one), it’s the perfect tool to keep me in the zone.

2. Asana for Project Management
   For complex, team-oriented projects, Asana is my go-to. It allows me to create detailed roadmaps, set gates, and track progress from a higher-level perspective. As a leader, it’s invaluable for identifying bottlenecks and ensuring that team members aren’t left waiting on deliverables.

3. Motion for AI-Powered Time Blocking
   Motion has become my secret weapon for managing my personal tasks. It uses AI to analyze my calendar, identify gaps, and reshuffle tasks as needed. This tool has taught me to set realistic deadlines and prioritize effectively. If I have 12 hours of work but only 8 hours to do it, Motion adjusts my schedule to focus on what’s most important.

4. Superhuman for Email
   Email can be a productivity killer, but Superhuman has transformed the way I manage my inbox. Its AI-powered search features, spam filtering, and ability to schedule emails for optimal delivery times have been a lifesaver. I can work on emails late at night without worrying about disrupting my team’s off-hours, respecting boundaries while still getting things done.

5. Pomodoro Technique
   For deep-focus work, I rely on the Pomodoro Technique. I set a timer for 25 minutes, work intensely on a task, and then take a 5-minute break. This method keeps me focused and prevents burnout, especially during long, demanding projects.

Evening Journaling: Closing the Day with Wins

One of the most impactful additions to my routine has been a quick, focused journaling session at the end of the day. It’s simple, takes less than five minutes, and helps me reflect on the day’s accomplishments while setting the stage for tomorrow.

Here’s my evening journaling process:

• Celebrate the Wins: I write down three big wins from the day. This helps me focus on the progress I’ve made, no matter how small, and keeps me from falling into a “gap mentality” where I only see what’s left undone.

• Set Tomorrow’s Priorities: I note what three things would make tomorrow feel accomplished. This allows me to hit the ground running in the morning with clarity and purpose.

• Reflect on the Day: I jot down a couple of sentences about how the day went. For example, “Felt low energy around 3 PM but powered through and cranked out a lot of work. Ended the day with a nice dinner with family.”

This simple practice keeps me grounded, helps me recognize my gains, and ensures that I’m always moving forward. It’s a moment of mindfulness that brings closure to the day and sets a positive tone for the next.

The Philosophy Behind Productivity

At its core, productivity isn’t just about tools—it’s about mindset. Here are a few principles that guide me:

• Leverage AI for Smarter Workflows: Tools like Motion and Superhuman demonstrate how AI can enhance productivity by automating scheduling, prioritization, and task management.

• Lead by Example: As a leader, your team looks to you to set the standard. If you’re organized, proactive, and thoughtful in your work, your team will follow suit.

• Balance is Key: Productivity isn’t about working 24/7. It’s about finding a balance that allows you to excel at work while still being a present parent, spouse, and friend.

• Renegotiate Promises: Life happens, and even the best-laid plans can go awry. When you know you won’t meet a deadline, communicate early and renegotiate. This builds trust and ensures that expectations are managed effectively.

Final Thoughts

Staying productive in a leadership role is no small feat. It requires a mix of the right tools, a disciplined mindset, and a commitment to continuous improvement. It’s not about never missing a deadline or always having a perfect day—it’s about doing your best to stay organized, focused, and thoughtful in your work.

So, how do you make the most of your day? What tools or techniques have transformed the way you work? I’d love to hear your thoughts and tips—because when it comes to productivity, there’s always room to learn and grow.