Jacob and Casey welcome guest Lacy Peterson to share her personal viewpoints and experiences on working as an Executive Assistant within an organization. The discussion has particular insight and anecdotes due to Lacy working specifically as an Executive Assistant within Casey’s workplace, and this allows the discussion to really focus on the details of their personal work relationship. Jacob guides the episode through the ins and outs of what an Executive Assistant role entails, and provides poignant questions that allows the listener to entertain how or why they may consider utilizing an Executive Assistant within their own organization or career. Casey offers plenty of examples of how Lacy has improved his personal workflows, and the ways in which her commitment to improvement within his organization overall has led to an increase in productivity and positive energy within the company.

In Part 2 of a series about AI, Casey and Jacob delve into the current landscape of Artificial Intelligence and how it is being used both in the workplace and personal life. They discuss specific ways that they have integrated AI into their personal workflows for efficiency and organization, and come to the conclusion that currently AI is best used to decrease time spent gathering and organizing information/notes, and to perform work that does not demand active human judgment. While the two agree that any person or employee needs to claim ownership and manipulate AI output for each given usage, they also reach the conclusion that AI can certainly help free up time for humans to focus on tasks and goals that truly require human thought, judgment, and connection. Oh, and it can help you be a better grandparent too!

In Part 1 of a series about AI, Jacob and Casey delve into the current landscape of Artificial Intelligence and how it is being used both in the workplace and personal life. They discuss their perspectives on the overall perception of AI in society and ways in which they personally use AI tools and agents within their own workflows. Though they feel AI has much potential, the leading takeaway is that it is still in its infancy and should be used in specific ways that may offer inspiration, organization, or a more streamlined efficiency for certain work tasks. Both Casey and Jacob share personal stories of circumstances in which they have witnessed the irresponsible use of AI and caution that relying on it may have unintended consequences.

Casey and Jacob have a fun look-back at 5 movies/shows that have shaped their work trajectories and styles of leadership. In part 2 of a 2 part series, they reminisce about titles like Moneyball, A Few Good Men, and Up In The Air – and how various characters, storylines, and management strategies within the movies made real impacts on their personal and work development. The two also discuss how challenging existing protocols and authority can be important in finding new paths to success as leaders by using innovation. One key takeaway is that leaders need to be diligent to avoid prioritizing their own ego, status, or achievements above what is best for their team.

Jacob and Casey have a fun look-back at 5 movies/shows that have shaped their work trajectories and styles of leadership. In part 1 of a 2 part series, they reminisce about titles like Office Space, Star Trek: The Next Generation, and The West Wing – and how various characters, plot developments, and styles of show-writing made real impacts on their personal and work development. The two also react about how they see each selection through their own personal lens, sometimes even having new revelations about the content as they work through the discussion. One key takeaway is that the age or stage in life in which you first experience media content is often so vital to what kind of impact it ultimately ends up having on you.

Casey and Jacob discuss the usage of levity within the work environment and ways in which it can be a positive and a negative. They work through some of their own experiences with using humor and other strategies to better relate to their work colleagues and often reduce tension. In addition to their own stories, the two also offer examples of notable leaders that they feel have best embodied the ability to use levity as a tool to navigate through work matters and also better appeal to the public. A major takeaway is that using levity can certainly be a risky action and needs to be used with awareness to the situation and other people involved.

In this episode, Jacob and Casey discuss their feelings and experiences on how so much of the work and impact that leaders make is unseen or goes without credit. They reflect on specific instances in their careers in which they needed to be patient, defer recognition, and suppress their egos or emotions in order to best serve their teams as leaders. The two also discuss how leadership is commonly misunderstood in terms of visibility and the various ways in which it has both downsides and tremendous value that often leads to some of the most meaningful work.

Casey and Jacob work through all the pros and cons of scheduling true vacations from work throughout the year. The two discuss why leaders need to be open to taking off more time from work, how a vacation can actually improve your ability to maintain present and future work output, and signs that you seriously need to get a vacation (or three) scheduled. Additionally, they lay out smart ways to make the most of a vacation and to feel confident that your team has everything in place for things to run smoothly while you’re away.

In this episode, Jacob and Casey discuss the importance of working on your own work by developing principles and practices that can help you get ahead of potential work obstacles and improve your own output individually and as a team leader. Jacob shares key takeaways and reflections from one of his favorite recent reads – Ray Dalio’s book “Principles”. Jacob discusses how the book has become a great reference and motivated him to formulate many of his own principles based on truths he has discovered over his career and experience.

The two spend time discussing and brainstorming on some of Jacob’s most important principles with themes like:

Mentions in this episode:

Ray Dalio's Book "Principles"

Jacob and Casey discuss crafting an ideal week—-a proactive approach to planning time for what matters most, protecting margin, and sustaining energy both at work and home.

They share how regularly reviewing and updating an ideal week template helps leaders hedge against chaos and interruptions, while staying focused on key priorities. Their discussion covers essential steps such as starting with a blank calendar, blocking out recurring meetings and personal routines, auditing current time use, and ensuring built-in flexibility and white space.

Casey and Jacob stress the importance of critical reflection: questioning the necessity of each meeting, reserving "deep work" periods, and blocking time for daily startup and shutdown routines. Other practical advice includes color-coding calendars, sharing ideal week philosophies with teams for alignment, and tracking "hit rates" against the plan to drive accountability and continuous improvement.

Key Points Discussed:

Actionable Takeaways:

Take charge of your time by designing your ideal week now and commit to revisiting it routinely, empowering yourself and your team to focus on what matters most.