Plan Your Next
Plan Your Next
Have you ever shared your financial situation?

Have you ever shared your financial situation?

Plan Your Next #84

👋 Good morning from Los Angeles! I'm Nate Kadlac, and this is #84 of Plan Your Next. A Sunday newsletter that connects design, creativity, and how you prepare for your next thing.

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📚 Currently reading: Hello, My Name is Awesome. A book about branding, and why some names are forgettable vs those that are memorable. Fun fact: was originally named

A journey about money
Illustration by yours truly

Good morning from Los Angeles!

In the popular Netflix series, Squid Game, 456 players crippled with debt compete against each other by playing children’s games for a shot at over 35 million dollars.

Putting over 450 people into one room, the inevitable conversations about how each of them ended up there would closely match real life. Everyone comes from a different background, with their own set of circumstances. Whether you were graduated with honors from Seoul National University like one of the main characters, or simply a divorced father addicted to gambling like the protagonist, debt knows no boundaries. It takes the best and the worst of us.

We don’t talk about our personal finances enough.

“…doing well with money has a little to do with how smart you are and a lot to do with how you behave. And behavior is hard to teach, even to really smart people.” —Morgan Housel, The Psychology of Money

I once tried to talk to a friend about personal finance, but I immediately sensed their spine lockup like a rusty bear trap. I dropped the subject, because I knew after I asked a couple of questions, they had been caught in this conversation before.

If our lives are the sum of the bets we have placed on ourselves, many of us don’t like rehashing when the bets didn’t work out.

It’s a subject I’ve spent over a decade learning about, trying to understand my own behavior and reasons for spending, investing, and saving.

I didn’t get serious about my own spending habits until after I turned 30, right after I sold my condo. Before I purchased that condo, I had scraped together everything I had at the time just to make a 10% downpayment of about 21k. It wiped out my savings, and to be honest, I thought it was a lot of money.

One of the reasons I thought it was a lot of money was because I had nothing to compare it to. No one talked much about personal finance, and I truly had no idea what I was doing. Making money wasn’t too much of a problem, but as a fresh freelancer, it was tough to be diligent about putting 10-15% of it away when you’re not sure about the next job. Money came in and out without gently brushing up against a brokerage or savings account.

So I did things like buy art, fly my dad to Argentina for a month long trip, and just find ways to live a fun life.

Software is eating our finances

I once asked my dad if he knew where he and my mom stood financially.

“I honestly have no idea.”


He didn’t realize that within an hour, he could be staring at a dashboard with a summary of where they stood. The thought scared him, mainly because of the hard conversations that would follow.

But I feel these conversations are starting to happen, even if it didn’t happen in my own family.

This tweet by Stew Fortier summarizes a feeling I’ve been having. Get an intimate group of people together to talk about their own finances. The trick is to come with an attitude that supports, and not compares.

Then there’s Nathan Barry—founder of ConvertKit which is valued at ~$200 million—who writes a paid newsletter describing his finances in full.

The explosion of web3, publicly shared crypto wallets and NFTs has also fueled a community collaboration of wanting to share and collect more in public. These conversations still act as a status signal in many ways, but it’s a wedge into much deeper conversations about leveraged economics and a bet on our future.

The F.I.R.E. (Financial Independance, Retire Early) movement is alive and kicking. It’s not what I strive for as much anymore, but it’s rooted in the basics of saving more than what you earn.

The first group who showed me ultimate transparency was an oldschool online forum called Bogleheads. It’s named after John Bogle, the founder of Vanguard who also happened to create the very first index fund. The forum doesn’t allow stock tips, but it does stick to the fundamentals of basing your allocations on low-fee based index funds.

This group opened up my eyes to how helpful people could be on the internet, and how much I could learn.

I certainly don’t have all the answers, but there’s no shame in looking for them.

:: Resources to level up your finances ::

Planning your next thing if you’re in debt is not a great place to be making decisions from. It can be debilitating, so I would seek proper financial guidance. I encourage you to be more curious if you are struggling, and don’t be afraid to ask questions.

Here are a few resources that have helped me along the way:

The Four Pillars of Investing

The Psychology of Money

Mr. Money Mustache Blog

The Coffeehouse Investor

Fire subreddit

You Need a Budget - Budgeting software

Monarch Money - Budgeting software

I Will Teach You to be Rich — Ramit Sethi

Money — Tony Robins

⚡️ Two creative hits for next week

✍️ How David Perell writes an essay

This interview with David Perell is a fantastic glimpse into his writing process. What I enjoyed was how he tests his ideas publicly in different settings to see what resonates.

“Sharing my ideas creates a virtuous cycle of new connections and opportunities” —David Perell

🎨 Jim Carrey: I Needed Color

Maybe you have seen this one before, but watching a comedian like Jim Carrey describe why he needed color in his life is heartwarming.

👋 See you next Sunday

If you’ve forgotten who I am, here’s a little bit about me. As always, my calendar is open to chat about your next adventure, crazy idea, or if you’re feeling creatively stuck.

Have a great week,


p.s. If you enjoyed this letter, would you please let me know by tapping on the heart below?

Plan Your Next
Plan Your Next
I'm Nate Kadlac, designer of Plan Your Next. A weekly newsletter that connects design, creativity, and how you prepare for your next thing.