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Modern Wisdom

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

Modern Wisdom

Chris Williamson

Society & Culture, Health & Fitness

4.65.9K Ratings

🗓️ 17 January 2026

⏱️ 72 minutes

🧾️ Download transcript

Summary

Jonathan Swanson is an entrepreneur and co-founder of Thumbtack. What if instead of using extra money to buy things, you used it to buy time? Delegation has never been easier, and with AI, you can 10× your productivity without working more. So what does smart delegation actually look like, and which tools make it possible? Expect to learn why buying hours is more important than buying things, why delegating your tasks is so important and the Cardinal sins of delegation, what Jonathan's top themes of being good at delegation are, what it would take to build your best life using assistants and much more… Timestamps: (0:00) Why is Time So Important? (8:12) How to Make More of Your Time (16:15) The Biggest Mistakes of Delegation (22:08) How to Build Your AI Assistant’s Algorithm (28:40) Ambition vs Leverage: What Drives Success? (36:39) How to Start Delegating to Your Assistant (42:48) Are There Any Downsides to Delegation? (47:03) The Assistants Who Shaped History (52:54) The Neuroscience Behind Delegation (56:41) The Best Ways to Reduce Phone Use (01:04:19) How to Overcome the Fear of Delegation (01:11:18) Where to Find Jonathan Sponsors: See discounts for all the products I use and recommend: ⁠https://chriswillx.com/deals⁠ Get the brand new Whoop 5.0 and your first month for free at https://join.whoop.com/modernwisdom Get 15% off your first order of Intake’s magnetic nasal strips at https://intakebreathing.com/modernwisdom Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom Get 15% off any Saily data plan at https://saily.com/modernwisdom Extra Stuff: Get my free reading list of 100 books to read before you die: ⁠https://chriswillx.com/books⁠ Try my productivity energy drink Neutonic: ⁠https://neutonic.com/modernwisdom⁠ Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: ⁠⁠⁠lnkfi.re/SN-Goggins⁠⁠⁠ #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠⁠⁠lnkfi.re/SN-Peterson⁠⁠⁠ #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠⁠⁠lnkfi.re/SN-Huberman⁠⁠ - Get In Touch: Instagram: ⁠https://www.instagram.com/chriswillx⁠ Twitter: ⁠https://www.twitter.com/chriswillx⁠ YouTube: ⁠https://www.youtube.com/modernwisdompodcast⁠ Email: ⁠https://chriswillx.com/contact⁠ - Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

How did you get started in thinking about time and delegating?

0:06.6

So my first job out of school was working at the White House, and I worked for the president's top economic advisor.

0:13.9

And I got to walk in the West Wing every morning, which was a cool life experience.

0:18.3

And I sat next to the president's executive assistants.

0:22.5

And as you might imagine, the executive assistants to the president are really freaking good.

0:27.1

And it set my bar crazy high for what this client EA partnership could look like.

0:34.4

And so when I left the White House to start my first company, I asked myself the question,

0:39.1

what if I had an assistant or a team of assistance that was as good as the presidents? Obviously,

0:45.0

I'm not going to become president, but what else could I accomplish if I had that sort of support?

0:48.9

And so I hired my first assistant that way and then set out on a journey to build the best team I could

0:55.4

to see how it changed my life. What were the unlocks that you saw inside of the White House?

1:00.9

Like how complex and big is the system of spindly octopuses with their tentacles and everything

1:08.4

trying to help get the machine moving? I mean, it's insane. The president has multiple assistance, as you might imagine.

1:14.8

There's actually an entire department called advance that plans every minute of the president's

1:19.8

life for months in advance. And so if he's going to be in Brazil in three months,

1:25.1

there's people deployed months in advance to go scope, prepare everything. And, you know, I think there's just kind of the level of

1:33.2

optimization, which is one thing. But the thing that really struck me sitting next to the president's

1:38.9

assistance is seeing the relationship they had. It wasn't just saving him time or doing tasks for him. At the end of the

1:47.5

day, he would sit down, lean back in his chair and be like, what happened? And he would talk to his

1:53.9

assistant. And this was one of the people he trusts most in the world. There's all these other people

1:58.6

jockeying for his attention, governor, senators,

2:06.5

and his eight chiefs. But this assistant is the one person who's just got his back fundamentally,

...

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