How to Make More Money (On Your Own Terms)

Good morning from Chiang Mai! 🇹🇭

I recently bought a GoPro Hero Black 13 (sooo exciting lol) and took it for a test drive on my motorbike around the city.

If you’re into that kind of thing, you can check out the video below 👇

The WSJ just reported the highest price ever paid for modern art at auction.

While equities, gold, bitcoin hover near highs, the art market is showing signs of early recovery after one of the longest downturns since the 1990s.

Here’s where it gets interesting→

Each investing environment is unique, but after the dot com crash, contemporary and post-war art grew ~24% a year for a decade, and after 2008, it grew ~11% annually for 12 years.*

Overall, the segment has outpaced the S&P by 15 percent with near-zero correlation from 1995 to 2025.

Now, Masterworks lets you invest in shares of artworks featuring legends like Banksy, Basquiat, and Picasso. Since 2019, investors have deployed $1.25 billion across 500+ artworks.

Masterworks has sold 25 works with net annualized returns like 14.6%, 17.6%, and 17.8%.

Shares can sell quickly, but my subscribers skip the waitlist:

Skip waitlist

_{*Per Masterworks data. Investing involves risk. Past performance not indicative of future returns. Important Reg A disclosures: masterworks.com/cd}

Hi friend,

I pitched a guy last week for $4,000 per month to manage his entire newsletter (setup, strategy, writing, etc)

He said no.

And while it was a little disappointing (the deal seemed promising) I also wasn’t crushed by the rejection either.

I just said “No worries!” and moved on.

Now in all honesty, that rejection would’ve destroyed me two years ago. I might’ve even backtracked:

“Actually, I could do it for $1,500”

…just to get the deal.

I would’ve convinced myself that I need to be flexible… that turning down money is stupid when you're trying to build a business.

But I didn't do any of that.

Because I don't need it anymore.

When I first started living on my own in 2023 (post-high school graduation), I’d just left the U.S. with a few thousand dollars in my bank account and no real plan beyond “figure it out when you get there.”

So when someone would ask about my rates for email work or newsletter management, I'd throw out $300 or $500 per month because I needed ANY client I could get.

I needed to eat.

I needed to prove to myself (and everyone who told me this was a terrible idea) that this whole thing wasn't a massive mistake.

It worked decently.

I was picking up gigs every month.

But I also got spread incredibly thin, burned out within months, and was severely undervaluing my work. If you actually did the math on hours worked versus money earned, I was making less than minimum wage.

But I kept telling myself it was temporary, that I just needed to get stable first, and then I could start being more selective.

Over time, things did stabilize.

I landed a few solid retainer deals with clients I actually liked working with. I’ve even had the opportunity to work with several big-name creators on their email marketing (don’t sleep on outreach, people lol 😉)

And suddenly I wasn't desperate anymore.

I wasn't checking my bank account every other day wondering if I could afford to eat out. Or if I could afford the $30 per night Airbnb.

And that shift changed everything about how I approach client work.

As one of my clients recently shared in a YouTube video

"When you're not desperate, you have the freedom to walk away. And [brands] can smell desperation from a mile away. It kills your leverage."

He was talking about sponsorship deals (i.e. how creators who don't need the money get better deals because they can say no to bad offers). But the same principle applies to literally anything:

The best position to negotiate from is "I'm good either way."

And that's where I was when I pitched that $4K project. When I sent over my rates last week, I genuinely meant it.

I wasn't bluffing or trying to anchor high so I could come down later. I was pricing the work at what it's actually worth to me, and if he said no, I'd just go back to focusing on the clients I already have and enjoy working with.

That's the position I'm in now.

And it's honestly kind of crazy because two years ago I couldn't even imagine getting here. I was so focused on just surviving and getting clients that the idea of pitching $4K per month (let alone being okay with a "no") would've seemed insane.

But you also can't start from that position.

You do have to go through the desperate phase first. You have to take the low-paying clients and say yes to projects you probably shouldn't and hustle like crazy just to get stable enough to breathe.

There's no shortcut around that part.

You can try skipping straight to "charge what you're worth" like the business gurus say, but you'll probably just end up with zero clients and a lot of self-doubt.

I know because I tried it.

Turns out "charge what you're worth" only works when you have credibility, a track record, and leverage. When you're starting out, you have none of those things.

So you hustle.

Undercharge.

Take whatever you can get.

And slowly, over months or years, you build up enough stability to start being selective.

And I think I'm finally at that point now.

As with the $4K rejection, I can honestly say it didn't sting as much as it probably would’ve two years ago.

Life goes on.

Yeah, an extra $4K would've been nice lol… but it's not necessary to my survival the way that first $100 client once was.

That's the real freedom, I think.

Pricing your work at what you think it's worth, and being able to walk away without flinching or second-guessing yourself.

Get stable first.

Then get selective.

Joshua

👨‍💻Beehiiv: The newsletter platform I use to write and send Outside the Lines. Easy-to-use interface, great analytics, and built for creators.

🚑 SafetyWing: Travel medical insurance designed for nomads. Covers you in 185+ countries and lets you pay month-to-month instead of per-trip.

🔐 NordVPN: The VPN I use daily to stay secure on public wifi and access content from anywhere in the world.

💰 Wise: The best way to send and receive money internationally without getting destroyed by bank fees. Essential for digital nomads.​​​​​​​​​​​​​​​​

These resources are affiliate links, which means I earn a small commission if you make a purchase. These are all services I currently use and love, and helps keep Outside the Lines free (at no extra cost to you).