Deep Work Habits and Better Breaks with Jake Kennington of Actively Human

In this episode of Time Billionaires, Rebecca sits down with Jake Kennington, founder of Actively Human, to explore how deep work, intentional breaks, and clearer boundaries can help professionals reclaim their time, and their sense of fulfillment.

Jake, a former licensed structural engineer, husband, father of four, and executive coach, shares how he helps mid-career professionals overcome burnout, break free from society’s default definition of success, and design a life aligned with their values rather than a “full calendar that leads to an empty life.”

Together, Rebecca and Jake unpack:

• Why deep work habits matter more than working longer hours
• How setting clear boundaries between work and personal time improves focus and satisfaction
• The Pomodoro Technique (25 minutes of focused work followed by a 5-minute break) and why it works
• Research shows that breaks are most restorative when they’re different from your main task, including simple resets like standing up, stepping outside, or getting sunlight
  Jake also shares a memorable story involving NBA champion Dwyane Wade to illustrate what it looks like to take proactive ownership of your role—on a team, in your career, and in your life.

Toward the end of the conversation, Jake explains why so many high-achieving professionals feel unfulfilled: they’re chasing someone else’s version of success. Drawing on the idea that “no one ever steps in the same river twice,” he walks through the importance of redefining success, realigning daily routines, and reconnecting with the people and work that matter most as life evolves.

Jake closes by revealing the surprising numbers behind his own journey, 25 homes, 14 cities, and 22 jobs, as a reminder that intentional choices around time, focus, and purpose are the real currency of long-term fulfillment.

Timestamps

1. Setting boundaries and managing your calendar (“full calendar, empty life”) - 00:58
2. Using the Pomodoro technique and micro-breaks for deep focus - 05:07
3. Defining your own success instead of chasing others’ metrics - 08:08
4. Opting into an intentional life versus the unwitting status quo - 11:09
5. The REDAC framework (Redefine, Realign, Reconnect) and why engagement & relationships matter - 14:43

Connect with Jake Kennington!

Website:https://activelyhuman.com/

LinkedIn: https://www.linkedin.com/in/jakekennington/

For simple daily mindset tips, follow Rebecca and the Time Billionaires Podcast on LinkedIn.

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Chapters

• (00:00:00) - How to Make More Money in a Short Time
• (00:00:57) - Time Billionaires: Jake Kennington
• (00:01:58) - Setting Boundaries for Your Calendar
• (00:09:03) - Why So Many People Are Unful
• (00:14:47) - Reclaiming Your Time