Modern Wisdom #1047: Jonathan Swanson – The Obvious Strategy to Take Back Your Time

Date: January 17, 2026
Host: Chris Williamson
Guest: Jonathan Swanson (Co-founder, Athena)
Theme: Strategies for regaining time and optimizing life through delegation and leveraging assistants.

Episode Overview

This enlightening conversation explores the transformative impact of delegation, both with human assistants and AI, in winning back our most precious resource—time. Jonathan Swanson discusses his introduction to elite-level assistance at the White House, traces the evolution of his own delegation journey, and offers concrete frameworks for anyone—regardless of means—to start reclaiming lost hours from daily drudgery. Chris and Jonathan tackle the psychology, practical challenges, and philosophical underpinnings of building a leveraged life, offering actionable steps, personal anecdotes, and surprising historical context.

Key Discussion Points & Insights

1. Origins: Lessons from the White House

Elite Standards of Delegation:
Swanson’s White House exposure set his standards for what a powerful partnership with an assistant could look like.

“The assistant is the one person who just got his back, fundamentally, emotionally, psychologically.”
(Jonathan Swanson, 01:32)
The Psychological Layer:
Assistants aren’t just administrative—they’re deep confidantes, privy to every emotional swing.

2. Building Personal Systems of Leverage

From Scarcity to Abundance:
Swanson describes scaling from a single assistant to a chief of staff with a team of six, each specializing (work, finance, kids, home).
Time as True Wealth:

“It’s the most primary asset in the world. It’s the ultimate currency.”
(Jonathan Swanson, 04:24)
Start Small, Scale Up:
Even simple delegation (e.g., hiring a cleaner or swapping babysitting with friends) is on the same continuum as building a ‘personal team.’

3. Accessible Levels of Delegation

(Practical road map for all budgets)

Level 0: Friends/family swaps (babysitting/dinner parties). [08:28]
Level 1: ChatGPT/AI ($20/mo) as digital assistants for habit-tracking, reminders, basic research.
Level 2: Freelancers via Upwork ($5-10/hr).
Level 3: Dedicated professional assistant (eg, Athena, ~$3,000/mo).
Ultimate: In-person executive assistants—a luxury for few.

“You can use ChatGPT to get started…Or you can delegate to your friends.” (Jonathan Swanson, 06:55)

4. Why Buying Time Beats Buying Things

Happiness Buyers:
“They’re not buying cars or clothes, they’re buying time.” (Swanson, 10:10)
Detangling the stigma (“I have a chef” feels elitist, but it’s often a better trade than a new car).

5. The Health-Time Link

Time Scarcity = Poor Health:
Lack of time derails fundamentals: “Why do people not sleep much? It’s... because they don’t have time.” (13:28)
Delegation as a Pillar of Well-being:
Offloading gives space for sleep, exercise, better routines.

6. What and How to Delegate

Start with Low-Energy, Annoying Tasks:
Renewing passports, inbox, calendar, paying bills [14:18]
Cognitive Offloading = Upgrade:

“Just like inflammation damages your body, chronic to-dos impair your mind.” (Jonathan Swanson, 15:11)
Levels of Delegation:
- Task-by-task: Simple requests.
- By process: Sharing how you like it done.
- By goal: Assistant executes based on broad objectives.
- Clairvoyant: Assistant anticipates and solves before you ask (the “nirvana”).

7. Cardinal Sins and Hurdles of Delegation

(And how to overcome them)

Pride: “It’s better/faster to do it myself.”
Guilt: Feeling uncomfortable ‘offloading’ to someone else.
Selfishness: Not giving enough access/context.
Lack of Commitment: Dabbling doesn’t work—“compounding” only happens over time and with trust.

“It’s like getting married, but only going on a couple dates.” (Swanson, 19:01)

8. The Tolerance for Inefficiency

Leverage means some inefficiency is a price for greater output:
“Do you measure life by efficiency, or by the good things you actually get to do?” (31:11)
Ambition Compounds with Leverage:
As you offload and free mental bandwidth, your ambitions—and the space to pursue them—grow.

9. Human + AI: The Next Evolution

Hybrid Model:
Human assistants remain the interface; AI augments (memory, rote stuff, 24/7 support).

“The AI will become an assistant to the human assistant.” (Swanson, 22:33)
Progressive Automation:
Analogous to self-driving cars; assisted first, fully automated later.

10. Feedback & Training for Effective Delegation

Practice specific, timely feedback—constantly.
Export your 'algorithm': share the how, not just the what.
Feedback best given by voice; easier and more nuanced.

“Helpful feedback is very specific and very timely.” (Swanson, 25:45)

11. Obstacles:

Fear of Losing Control/Trust:
Solution: Build trust gradually, widen access over time.
Not Knowing What to Delegate:
Start with low-value tasks, then aspirations.

12. Historical Context: Delegation is Ancient

From Cicero to Edison to Catherine the Great, almost all high-achievers had aides, assistants, or fact-gathering teams.

“History awards points for getting it done. And the way you get things done is with a team.” (Swanson, 51:27)

13. Neuroscience of Delegation

The brain itself delegates within—complex tasks to prefrontal cortex, routine to automation.

“It’s not that our brain was merely wired for delegation, but it was wired by delegation.” (Swanson, 53:24)

14. Life Experiments

Swanson’s “no calendar, no meetings” period brought immense freedom post-startup-burnout.
Voice delegation is superior; you speak 3–5x faster than typing, and it lowers the activation energy for both feedback and requests.

15. Reducing Digital Distraction

The “Freedom Phone” experiment: use a minimalist phone with only essentials, kept wife-locked (“my wife has the code”) to reduce temptation. [57:04]
Chris’s approach: multiple “cocaine phones”, one for work apps, one for habit apps, one for daily use—limits distraction by design.

16. Onboarding Your Own Assistant: The Full Stack

Start: Offload pain/painful tasks (calendar, inbox). Be patient—it takes months/years, not weeks.
Mid-level: Teach your processes and routines.
Advanced: Delegate by objective/goal.
Nirvana: Assistant is anticipating your needs.

17. Pitfalls of Over-Delegation

Don’t delegate what’s meaningful—spend your own time on “the good stuff.”
Always treat assistants with respect; Athena declines clients who are disrespectful.

Notable Quotes & Memorable Moments

On the emotional bond with assistants:
“At the end of the day, [the President] would sit down... and he would talk to his assistant. This was one of the people he trusts most in the world.”
(Swanson, 01:19)
On guilt and the dignity of delegation:
“Delegation is your way of gifting to someone else. You're giving them a job, you’re giving them income.”
(Swanson, 12:31)
On historical perspective:
“Catherine the Great... had someone dedicated to first dates and to testing, quote, male capacity… Catherine, you are an OG Delegator.”
(Swanson, 49:27)
On inefficiency as the price for ambition:
“How do you measure your life? ... by efficiency, or... by the good life that you want?”
(Swanson, 31:11)
On the ultimate state of delegation:
“The first time you hear about a task is when it's done... and now you can go on to do something else.”
(Swanson, 40:34)

Timestamps for Essential Segments

[00:07] Swanson’s White House origin story
[03:01] Scaling up to a Chief of Staff & six assistants
[04:24] On time as the ultimate asset
[06:55] Ways to start without much money (peer swaps, AI, Upwork)
[10:35] Why outsourcing triggers guilt or class anxieties
[13:28] Time scarcity’s impact on health
[14:18] What to offload first: “Energy sappers”
[16:20] Sins of delegation: Pride, guilt, selfishness, lack of commitment
[22:33] How AI integrates with human delegation
[25:45] How to give better, more frequent feedback
[29:20] Building a tolerance for inefficiency
[31:58] Leverage vs. ambition: the reinforcing spiral
[37:06] Onboarding and levels of effective delegation
[47:33] Ancient examples: Cicero, Newton, Catherine the Great
[53:24] The brain’s intrinsic delegation structures
[54:24] Swanson’s radical experiments (no-calendar, voice-only delegation)
[56:39] Reducing phone addiction (the “Freedom Phone”)
[66:41] Where to find delegation playbooks and resources (playbooks.athena.com)
[68:50] Can you delegate the act of delegation?
[71:38] Where to learn more & connect with Athena

Tone and Takeaways

Chris brings his hallmark practical skepticism and humor; Jonathan responds with down-to-earth personal anecdotes and a mix of practicality and vision. Rather than advocating elitist, “rich person” hacks, both consistently return to first principles: time is precious, anyone can start, and the happiest people invest in relationships and meaning—not endless drudgery or hollow consumption.

Final Takeaway:

Starting where you are—by offloading a small chore or learning how to delegate to ChatGPT—is the first step in a lifelong journey of building a leveraged, richer life with more time for what actually matters.

Relevant Links:

Athena: Executive Assistants
Chris Williamson’s Book List
Athena’s Playbooks (delegation resources)

End of Summary

Modern Wisdom #1047: Jonathan Swanson – The Obvious Strategy to Take Back Your Time

Episode Overview

Key Discussion Points & Insights

1. Origins: Lessons from the White House

Elite Standards of Delegation:
Swanson’s White House exposure set his standards for what a powerful partnership with an assistant could look like.

“The assistant is the one person who just got his back, fundamentally, emotionally, psychologically.”
(Jonathan Swanson, 01:32)
The Psychological Layer:
Assistants aren’t just administrative—they’re deep confidantes, privy to every emotional swing.

2. Building Personal Systems of Leverage

From Scarcity to Abundance:
Swanson describes scaling from a single assistant to a chief of staff with a team of six, each specializing (work, finance, kids, home).
Time as True Wealth:

“It’s the most primary asset in the world. It’s the ultimate currency.”
(Jonathan Swanson, 04:24)
Start Small, Scale Up:
Even simple delegation (e.g., hiring a cleaner or swapping babysitting with friends) is on the same continuum as building a ‘personal team.’

3. Accessible Levels of Delegation

(Practical road map for all budgets)

Level 0: Friends/family swaps (babysitting/dinner parties). [08:28]
Level 1: ChatGPT/AI ($20/mo) as digital assistants for habit-tracking, reminders, basic research.
Level 2: Freelancers via Upwork ($5-10/hr).
Level 3: Dedicated professional assistant (eg, Athena, ~$3,000/mo).
Ultimate: In-person executive assistants—a luxury for few.

“You can use ChatGPT to get started…Or you can delegate to your friends.” (Jonathan Swanson, 06:55)

4. Why Buying Time Beats Buying Things

Happiness Buyers:
“They’re not buying cars or clothes, they’re buying time.” (Swanson, 10:10)
Detangling the stigma (“I have a chef” feels elitist, but it’s often a better trade than a new car).

5. The Health-Time Link

Time Scarcity = Poor Health:
Lack of time derails fundamentals: “Why do people not sleep much? It’s... because they don’t have time.” (13:28)
Delegation as a Pillar of Well-being:
Offloading gives space for sleep, exercise, better routines.

6. What and How to Delegate

Start with Low-Energy, Annoying Tasks:
Renewing passports, inbox, calendar, paying bills [14:18]
Cognitive Offloading = Upgrade:

“Just like inflammation damages your body, chronic to-dos impair your mind.” (Jonathan Swanson, 15:11)
Levels of Delegation:
- Task-by-task: Simple requests.
- By process: Sharing how you like it done.
- By goal: Assistant executes based on broad objectives.
- Clairvoyant: Assistant anticipates and solves before you ask (the “nirvana”).

7. Cardinal Sins and Hurdles of Delegation

(And how to overcome them)

Pride: “It’s better/faster to do it myself.”
Guilt: Feeling uncomfortable ‘offloading’ to someone else.
Selfishness: Not giving enough access/context.
Lack of Commitment: Dabbling doesn’t work—“compounding” only happens over time and with trust.

“It’s like getting married, but only going on a couple dates.” (Swanson, 19:01)

8. The Tolerance for Inefficiency

Leverage means some inefficiency is a price for greater output:
“Do you measure life by efficiency, or by the good things you actually get to do?” (31:11)
Ambition Compounds with Leverage:
As you offload and free mental bandwidth, your ambitions—and the space to pursue them—grow.

9. Human + AI: The Next Evolution

Hybrid Model:
Human assistants remain the interface; AI augments (memory, rote stuff, 24/7 support).

“The AI will become an assistant to the human assistant.” (Swanson, 22:33)
Progressive Automation:
Analogous to self-driving cars; assisted first, fully automated later.

10. Feedback & Training for Effective Delegation

Practice specific, timely feedback—constantly.
Export your 'algorithm': share the how, not just the what.
Feedback best given by voice; easier and more nuanced.

“Helpful feedback is very specific and very timely.” (Swanson, 25:45)

11. Obstacles:

Fear of Losing Control/Trust:
Solution: Build trust gradually, widen access over time.
Not Knowing What to Delegate:
Start with low-value tasks, then aspirations.

12. Historical Context: Delegation is Ancient

From Cicero to Edison to Catherine the Great, almost all high-achievers had aides, assistants, or fact-gathering teams.

“History awards points for getting it done. And the way you get things done is with a team.” (Swanson, 51:27)

13. Neuroscience of Delegation

The brain itself delegates within—complex tasks to prefrontal cortex, routine to automation.

“It’s not that our brain was merely wired for delegation, but it was wired by delegation.” (Swanson, 53:24)

14. Life Experiments

Swanson’s “no calendar, no meetings” period brought immense freedom post-startup-burnout.
Voice delegation is superior; you speak 3–5x faster than typing, and it lowers the activation energy for both feedback and requests.

15. Reducing Digital Distraction

The “Freedom Phone” experiment: use a minimalist phone with only essentials, kept wife-locked (“my wife has the code”) to reduce temptation. [57:04]
Chris’s approach: multiple “cocaine phones”, one for work apps, one for habit apps, one for daily use—limits distraction by design.

16. Onboarding Your Own Assistant: The Full Stack

Start: Offload pain/painful tasks (calendar, inbox). Be patient—it takes months/years, not weeks.
Mid-level: Teach your processes and routines.
Advanced: Delegate by objective/goal.
Nirvana: Assistant is anticipating your needs.

17. Pitfalls of Over-Delegation

Don’t delegate what’s meaningful—spend your own time on “the good stuff.”
Always treat assistants with respect; Athena declines clients who are disrespectful.

Notable Quotes & Memorable Moments

On the emotional bond with assistants:
“At the end of the day, [the President] would sit down... and he would talk to his assistant. This was one of the people he trusts most in the world.”
(Swanson, 01:19)
On guilt and the dignity of delegation:
“Delegation is your way of gifting to someone else. You're giving them a job, you’re giving them income.”
(Swanson, 12:31)
On historical perspective:
“Catherine the Great... had someone dedicated to first dates and to testing, quote, male capacity… Catherine, you are an OG Delegator.”
(Swanson, 49:27)
On inefficiency as the price for ambition:
“How do you measure your life? ... by efficiency, or... by the good life that you want?”
(Swanson, 31:11)
On the ultimate state of delegation:
“The first time you hear about a task is when it's done... and now you can go on to do something else.”
(Swanson, 40:34)

Timestamps for Essential Segments

[00:07] Swanson’s White House origin story
[03:01] Scaling up to a Chief of Staff & six assistants
[04:24] On time as the ultimate asset
[06:55] Ways to start without much money (peer swaps, AI, Upwork)
[10:35] Why outsourcing triggers guilt or class anxieties
[13:28] Time scarcity’s impact on health
[14:18] What to offload first: “Energy sappers”
[16:20] Sins of delegation: Pride, guilt, selfishness, lack of commitment
[22:33] How AI integrates with human delegation
[25:45] How to give better, more frequent feedback
[29:20] Building a tolerance for inefficiency
[31:58] Leverage vs. ambition: the reinforcing spiral
[37:06] Onboarding and levels of effective delegation
[47:33] Ancient examples: Cicero, Newton, Catherine the Great
[53:24] The brain’s intrinsic delegation structures
[54:24] Swanson’s radical experiments (no-calendar, voice-only delegation)
[56:39] Reducing phone addiction (the “Freedom Phone”)
[66:41] Where to find delegation playbooks and resources (playbooks.athena.com)
[68:50] Can you delegate the act of delegation?
[71:38] Where to learn more & connect with Athena

Tone and Takeaways

Final Takeaway:

Relevant Links:

Athena: Executive Assistants
Chris Williamson’s Book List
Athena’s Playbooks (delegation resources)

End of Summary

#1047 - Jonathan Swanson - The Obvious Strategy to Take Back Your Time

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Summary

Modern Wisdom #1047: Jonathan Swanson – The Obvious Strategy to Take Back Your Time

Episode Overview

Key Discussion Points & Insights

1. Origins: Lessons from the White House

2. Building Personal Systems of Leverage

3. Accessible Levels of Delegation

4. Why Buying Time Beats Buying Things

5. The Health-Time Link

6. What and How to Delegate

7. Cardinal Sins and Hurdles of Delegation

8. The Tolerance for Inefficiency

9. Human + AI: The Next Evolution

10. Feedback & Training for Effective Delegation

11. Obstacles:

12. Historical Context: Delegation is Ancient

13. Neuroscience of Delegation

14. Life Experiments

15. Reducing Digital Distraction

16. Onboarding Your Own Assistant: The Full Stack

17. Pitfalls of Over-Delegation

Notable Quotes & Memorable Moments

Timestamps for Essential Segments

Tone and Takeaways

Final Takeaway:

Summary

Modern Wisdom #1047: Jonathan Swanson – The Obvious Strategy to Take Back Your Time

Episode Overview

Key Discussion Points & Insights

1. Origins: Lessons from the White House

2. Building Personal Systems of Leverage

3. Accessible Levels of Delegation

4. Why Buying Time Beats Buying Things

5. The Health-Time Link

6. What and How to Delegate

7. Cardinal Sins and Hurdles of Delegation

8. The Tolerance for Inefficiency

9. Human + AI: The Next Evolution

10. Feedback & Training for Effective Delegation

11. Obstacles:

12. Historical Context: Delegation is Ancient

13. Neuroscience of Delegation

14. Life Experiments

15. Reducing Digital Distraction

16. Onboarding Your Own Assistant: The Full Stack

17. Pitfalls of Over-Delegation

Notable Quotes & Memorable Moments

Timestamps for Essential Segments

Tone and Takeaways

Final Takeaway: