Hey Reader,

Back in 2021, I spent five days backpacking 44 miles through the Sawtooth Mountains in Idaho.

At one point we were 20 miles from the nearest road, and we went three full days without seeing another person. It was incredible.

Earlier this year, I read about someone who took hiking more seriously than I do: Theodore Roosevelt, the 26th president of the United States, believed physical toughness made him who he was. And he wanted his kids to have it too.

On their hikes, there was just one rule: Walk in a straight line. Whatever you come across, go over it, under it, or through it, but never around.

That’s a pretty extreme way to raise kids, and it came with some side effects.

In 1914, a few years after he left office, Roosevelt spent months on an unexplored river in the Amazon. His 24-year-old son Kermit came along and was the toughest person on the trip. Kermit had so little fear that it made Roosevelt nervous, and he started to wonder if he’d pushed the parenting thing too far (Kermit regularly did extreme things like jumping into rapids to save a fellow adventurer or one of their canoes).

I don’t think you need to go quite to the extent Roosevelt did to get the benefit, but when you choose to push yourself, mentally and physically, you get a lot better at handling change.

The same thing is true with money. I grew up in a family with six kids, and some years we lived on $25,000. We had everything we needed, but I didn’t eat at a restaurant until college.

Ramit Sethi said people who grew up poor and are now wealthy aren’t worried about losing it all. They’ve already lived through the worst case, so they know they’re going to be okay.

Hard things you choose will give you confidence. Each one shows you that you can handle more than you thought.

Making money works in a similar way. It’s a skill you can build on purpose, and that’s the whole idea behind my book, The Ladders of Wealth. You can read the first chapter free at LaddersofWealth.com and also get some bonuses there when you pre-order.

Every time you pick a hard thing, you’re also picking which kind of pain you’d rather have.

So much of life is the balance between short-term pain and long-term pain. If you’re unwilling to endure short-term pain, you’re probably going to have a lot of long-term pain.

Many times at Kit, I’ve chosen the short-term pain to get the long-term benefit. I turned down an acquisition offer, and I went through team members leaving. Both were painful at the time, but both let me build the company on my own terms—with people who are in it for the long haul.

If you always take the easy way out, life gets a lot harder long term.

Of course, doing hard things only helps if you balance them with rest. I don’t think you should grind yourself into the ground.

It’s a lot like going to the gym. When I push hard in a workout, I know I’m going to be done in an hour, and that’s what lets me go all in. Your muscles get stronger while you rest. Pushing yourself too hard every day without any breaks is how you burn out.

Try one hard thing this week that has a finish line.

That could be a tough workout or a long hike. Then, give yourself time to rest. The next time something big changes, you’ll have a lot less reason to panic, because you’ll already know you can handle hard things.

​

PODCAST

The Newsletter Is Dead. Here’s How To Survive AI Agents

AI agents are going to read your newsletter before your subscribers do.

At least, that’s Dan Shipper’s take. He runs Every, a company that writes about AI and builds AI software, and he’s about as close to the cutting edge as anyone I know.

I’ve spent 13 years building my career around email, so this was difficult to hear. As much as I hate to admit it, Dan might be right.

We get into:

• Why Dan barely opens his inbox anymore
• What Every is testing so they don’t depend on the inbox
• What you can start doing now to make sure your emails still get through

​Watch or listen to episode »​

Sidenote: Before we recorded Dan set up Subscriber Signals for the Every newsletter and we reviewed it together. He probably has the highest quality newsletter subscribers I've ever seen.

CASE STUDY

How Colin Rocker Uses His Email List Data to Grow on Purpose

If you’re trying to figure out what to build next, the people on your email list can help you decide.

Colin Rocker runs a monthly gathering in New York for professionals who are the first in their family to hold a corporate job. It’s called For the Firsts.

People in other cities asked for chapters too, but Colin wanted to get the New York event right first. Now he looks at where his subscribers live and what they earn to decide which city comes next.

Here’s how he does it, if you want to try the same with your list.

​Read case study »​

CARD GAME

Archduke

I picked up Archduke randomly at a bookstore when I was on the Harvard campus, and it was an immediate hit with all of my kids.

It’s a memory and strategy card game that’s a lot of fun. It’s quite challenging, but my six-year-old might be the best at it of all of us.

​View game »​

Have a great week!

—Nathan