A lot of people don’t struggle with money because of numbers.
They struggle because of shame.
Shame from:
past debt
impulsive decisions
bad spending habits
missed payments
failed savings attempts
ignoring finances for too long
But here’s the truth most people never hear:
Your past choices do not decide your financial future.
Your next choice does.
Today’s email is all about helping you build confidence — even if you feel behind.
💛 1. Confidence Comes From Action, Not Perfection
People think confidence comes from “getting everything right” with money.
Not true.
Confidence grows when you take small, consistent actions.
Every tiny win builds proof that:
👉 “I’m capable.”
👉 “I’m improving.”
👉 “I can do this.”
You don’t need to be perfect.
You just need to keep moving.
🔁 2. Forgive Your Old Financial Self
This part matters.
You cannot build a strong financial future if you’re still punishing yourself for the past.
Think of your past self with compassion:
They were stressed, uninformed, overwhelmed, or just trying their best.
You’re not that version anymore.
You’re learning, improving, and taking control now.
Forgiveness clears the mental space for growth.
🧩 3. Break Confidence Into Four Small Skills
Financial confidence is not one big thing.
It’s built from small skills:
1. Clarity – knowing where your money goes
2. Control – making intentional decisions
3. Consistency – repeating small habits
4. Knowledge – learning a little more each week
If you focus on these four areas, confidence grows naturally.
📈 4. Track Your Wins (Even the Tiny Ones)
Your brain tends to remember failures more than victories.
So you have to actively remind yourself that you’re improving.
Write down wins like:
“I saved $10.”
“I didn’t impulse-buy today.”
“I checked my accounts.”
“I set up autopay.”
“I paid off a little debt.”
“I learned a new money term.”
These wins stack up and rewrite your identity.
They prove you are capable — not someday… right now.
🛠 5. Do One Thing That Makes You Feel Powerful This Week
Confidence isn’t built from thinking —
it’s built from doing.
Here are examples of powerful moves:
open a savings account
invest $5
set up automatic transfers
cancel a subscription
organize your financial documents
rename your savings account (“Future Me Fund”)
build a tiny $20 emergency cushion
Each of these creates momentum.
🌱 This Week’s Challenge
Choose one small action that makes you feel stronger with money.
Just one.
Then write down how it made you feel afterward.
That’s how confidence grows:
Action → Evidence → Belief → Identity.
Crash Expert: “This Looks Like 1929” → 70,000 Hedging Here
Mark Spitznagel, who made $1B in a single day during the 2015 flash crash, warns markets are mimicking 1929. Yeah, just another oracle spouting gloom and doom, right?
Vanguard and Goldman Sachs forecast just 5% and 3% annual S&P returns respectively for the next decade (2024-2034).
Bonds? Not much better.
Enough warning signals—what’s something investors can actually do to diversify this week?
Almost no one knows this, but postwar and contemporary art appreciated 11.2% annually with near-zero correlation to equities from 1995–2024, according to Masterworks Data.
And sure… billionaires like Bezos and Gates can make headlines at auction, but what about the rest of us?
Masterworks makes it possible to invest in legendary artworks by Banksy, Basquiat, Picasso, and more – without spending millions.
23 exits. Net annualized returns like 17.6%, 17.8%, and 21.5%. $1.2 billion invested.
Shares in new offerings can sell quickly but…
*Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.