How Do I Know When to Take Money Out of My Investments?
How Do I Know When to Take Money Out of My Investments?
One of the questions I get all the time is:
“How do I know when it’s okay to take money out of my investments?”
Most financial advice teaches you one thing:
Keep investing.
And honestly? That’s good advice…until it isn’t.
Because nobody teaches you when it’s actually okay to enjoy the wealth you’ve built.
I call these the two phases of building wealth:
- Accumulation
- Extraction
Understanding the difference completely changed how I think about money.
Phase 1: Accumulation
When you’re in accumulation mode, your job is simple:
Keep buying.
Keep investing.
Keep letting compound interest do its thing.
When I first started investing, I wasn’t making six figures.
I wasn’t even making $45,000 a year.
But I kept buying anyway because a financial advisor once showed me a chart of the stock market and said:
“Yes, it’s volatile in the short term. But look at how much growth you’re missing by waiting.”
That conversation changed my life.
I stopped trying to time the market.
I stopped waiting until I “made more.”
I started buying consistently.
That’s how I built my first $250,000 of net worth.
Phase 2: Extraction
Then something interesting happens.
Your investments stop being numbers on a screen.
They become a tool.
A few years ago, I really wanted to see Karol G in concert.
Old Charly would’ve thought:
“I can’t spend that much money.”
Instead, I looked at my brokerage account.
I had investments that had grown.
I sold some stock.
I bought the ticket.
I danced my ass off.
And I have zero regrets.
Because that’s exactly what I built the money for.
I’ve also sold investments during slower seasons in my business—not because I was panicking, but because I’d intentionally built a taxable brokerage account that could support me when cash flow dipped.
Another time, I sold stock to strengthen my emergency fund because sleeping well at night was worth more to me than squeezing out a little more market return.
Those decisions weren’t emotional.
They were strategic.
That’s extraction.
Selling Stock Isn’t Automatically Bad
I think we’ve accidentally created this weird badge of honor in the personal finance world where people brag about never selling.
But never selling isn’t the goal.
The goal is freedom.
If selling stock lets you:
🌈 Take a once-in-a-lifetime trip.
🌈 Cover a slow business season without going into debt.
🌈 Rebuild your emergency fund after an unexpected expense.
🌈 Work less because your investments are supporting your life…
…then your investments are doing exactly what they’re supposed to do.
The key is why you’re selling.
There’s a huge difference between:
🚨 Selling because the market dropped 20% and you’re terrified.
and
✨ Selling because you’ve intentionally decided your money can improve your life today.
One is fear.
The other is a plan.
My Retirement Accounts Are Different
This is also why I almost never touch my Roth IRA or retirement accounts.
Those accounts have one job:
Take care of Future Charly.
My brokerage account has a different job.
It gives Present Charly flexibility.
That’s the account I think about when I want to invest in my life today, whether that’s a concert, a sabbatical, navigating a slow business season, or making sure I have enough cash to sleep peacefully at night.
Every account has a purpose.
When you know what that purpose is, money decisions become a lot less emotional.
Money Is Meant to Be Used
I think so many people become incredible accumulators.
They save.
They invest.
They max out their retirement accounts.
And then…
They forget to live.
They postpone joy until retirement.
They feel guilty every time they spend.
They convince themselves that one more year of saving will finally make them feel safe.
Maybe.
But maybe not.
I’ve coached people with hundreds of thousands of dollars invested who still feel anxious spending $500.
That’s not a math problem.
That’s a mindset problem.
Build Wealth So You Can Use It
I’m not telling you to spend recklessly.
I’m telling you to build wealth intentionally so that one day you can extract it intentionally.
That’s the whole point.
Money isn’t the finish line.
Want to Build Your First $250K?
If you’re still in the accumulation phase and want to know exactly what to do first with your cash, credit, debt, and investments, I’d love to have you at my free live webinar:
Build Your First $250K Without Making More Money
You’ll learn:
🤑 Where your money should actually go first.
🤑 How rich gay aunties and uncles think during market crashes.
🤑 How to build wealth without waiting for a bigger paycheck, zero debt, or a “better” economy.
⚠️ The webinar will not be recorded.
If you can’t attend live, you’ll miss it. REGISTER HERE.
Listen to the Unicorn Millionaire Episode 149: How Do I Know When to Take Money Out of My Investments?
In my latest Unicorn Millionaire Podcast episode, I go deeper into how to build wealth qithout making more money.
“How Do I Know When to Take Money Out of My Investments?” 🦄
🎧Listen to Episode 149 of the Unicorn Millionaire Podcast on Spotify
🎧Listen to Episode 149 of the Unicorn Millionaire Podcast on Apple Podcasts
Ready to optimize your money?
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I’d love to help you make your money work for you.
If you want hands-on support understanding your investments, opening the right accounts, selling out of overpriced or underperforming funds, boosting your credit score, and building toward early retirement, you can learn more about my six-month one-on-one money coaching program.
I help LGBTQ+, BIPOC, and first-gen folks crush confusion around money and start building a six-figure retirement—even without a six-figure salary.
If you’re ready to maximize your savings and invest it, let’s work together.
We’ll get you on track to:
- Crush debt without shame
- Grow your cash in the right places
- Raise your credit score (see how my client raised her by 100 points in less than 6 months)
- Learn to sell stock without guilt
- Start building a six-figure retirement—even without a six-figure salary
Coaching includes bi-weekly calls, daily messaging, and a full curriculum covering savings, credit cards, debt payoff, investing, and money mindset.
Investment: $6,000 or two payments of $3,100.
Six-Month 1:1 Coaching includes:
- Bi-weekly calls
- Daily messaging support
- A full curriculum on savings, debt payoff, credit, investing, and money mindset
- Investment: $6,000 or two payments of $3,100
Or, sign up for my Crush Debt, Retire Early Emails here.
About Charly
I’m Charly Stoever (@travelercharly) — a trans Latinx money coach, speaker, and host of the Unicorn Millionaire Podcast. I help LGBTQ+, BIPOC, and first-gen folks crush debt and build a six-figure retirement—even without a six-figure salary.
As a formerly undocumented Mexican American and ex-stockbroker who’s traveled solo to 39 countries, I now coach full-time while also international pet sitting.
If you’re ready to stop avoiding your finances and start using your money on purpose, work with me.
Get your coaching FAQs answered here, and book a call with Charly to get started with 6 month coaching here.