Try nice things

Plan Your Next: Letter No. 9


Happy Sunday! I hope you have had a good week so far!

Does today feel like the start of the week or the end of the week for you?

For as long as I can remember, I’ve always felt that it’s the end of the week; Monday being the start. All of my digital calendars are setup to start the week on a Monday.

There is something about ending the week on a more leisurely note, and beginning the week with some intentional brain power that sits well with me. But shortly after that first cup of coffee, of course.

Why can’t we all have nice things?

One summer when I was about 12 (my childhood all blurs together at this point), my parents sat my 3 siblings and I down at the kitchen table, and asked us to choose between a trip to Disney World or an above ground 4ft swimming pool.

I was shocked; we never splurged on anything. We were an average middle class family, supported by one income.

When it came to having things, it was never brand name items in the house. We bought a lot of knock-offs, like detergent and hand soap called Triple-H, whose concentrate was diluted down to hardly anything effective.

Popular stuffed animals like Sock Monkeys or Pillow People were never bought, but instead sewn by grandma.

We bought hand-me-down items like a snowmobile and mini-scooter for less than $50, only to see them break down after one or two uses.

Back at that kitchen table, the four of us needed only about 3 seconds to decide that we wanted the swimming pool. We would figure out who would clean it out later. Details.

What was special about that moment is that it’s the one time that I can remember when my parents went out and purchased something new, which lasted more than a few days.

Now, pools are fine and fun and cool to chill at, but anytime I see one, I compare it against the one I had growing up. Those memories come rushing back, reminding me of all my birthday’s out on the deck and how any other pool won’t be the same.

I’ve found that basic principle of trying out nice things can help define what we really want in life. The basic principle of asking yourself, “Will this make me happy?” is always a good start, but sometimes you need to give yourself a chance to say no, by saying yes.

The riskiest decision I made was to buy a home. There are many reasons why I shouldn’t have owned, but sometimes no matter who you talk to, you’re going to get recycled advice. Many of the ideas we hear vocalized aren’t our own—rather verbal clickbait— and it’s up to us to decipher between the bullshit and the truth.

A popularized phrase this year by Nassim Taleb, which happens to be the name of his own book, is having skin in the game. One of the hundreds of points he makes is that if we’re seeking out advice, we should only be listening to those who have something to lose themselves. Otherwise, they’re not losing anything by offering up a potentially damaging opinion.

It’s sometimes hard to discern between what you need and what you want without experiencing them for yourself. You don’t always have to own something to do that.

The idea isn’t to go out and buy everything you want, but rather rent or lease first, to scratch that itch you have. Lower the risk you’re taking with big commitments, and make decisions based on if it will make you a happier person.

One example for me: For the past 5 years I’ve wanted to buy a Jeep. It’s not that practical for us, but they are so much damn fun. I’ve argued for it from a lot of angles, but in the end it doesn’t make that much sense. For one, we live in LA, where the Prius reigns supreme. Two, our paid-off car still works. Kind of :) To scratch that itch, I rented a Jeep for a week to drive around, and so far it’s worked.

One counter: I recently purchased a Peloton to give it a shot for 30 days. I haven’t had a gym membership in years, but I love to workout at home. For cardio, I have piss-poor knee/feet issues—which is why I hate running—and want to test to see if the convenience of having it inside motivates me to be healthier. It’s not a cheap purchase so I’m trying to weight that opportunity cost.

Low Risk, High Reward

I love the often told story of how Richard Branson started Virgin Airlines. He negotiated with Boeing to lease his first airplane which allowed him to return it if his company didn’t succeed. While he had a willingness to fail, he didn’t want to put himself at risk by making a bad decision out of the gates.



What are some indulgences that you have tried recently?

I’ve got some website updates in the works, and my next project is to create a page for favorite books that I’ve read. I do plan to start writing there in due time, but plan to continue using this newsletter as a way to lightly explore random ideas.

I really appreciate you continuing to indulge me in this, and if your’e ever feeling stuck, please reach out. And as always, if this isn’t for you, unsubscribing is just a couple clicks away.

Have a great week!

This is Plan Your Next. It’s a conversation about being ready for what’s next. Well, because there is always a next. I’m Nate, designer, and conductor of this group.

If you have something to share or add, please hit reply and expect a response!