How You Can Sell Stock and Still Retire Early
How You Can Sell Stock and Still Retire Early
One of the biggest fears people have about investing is the idea that if they ever sell stock, they’ll ruin their retirement.
Clients tell me all the time that they feel like once money goes into the stock market, they’re never supposed to touch it again until they’re 65 or 70.
But the truth is that selling stock can be part of a smart wealth-building strategy when you understand which account to sell from, when it makes sense to sell, and how to do it without creating unnecessary taxes or panic.
Recently, I sold $5,000 of VTI, a low-cost index fund that tracks the stock market, from my taxable brokerage account. This wasn’t a last-minute emotional decision or panic selling. It was a thoughtful choice based on my financial goals, my tax situation, and my need for peace of mind.
That investment had grown by 71% over six years, which is exactly what investing is supposed to do: grow your money so that you eventually have options.
Selling stock didn’t derail my retirement plan. If anything, it reminded me why investing works in the first place.
What You’ll Learn in This Episode
• Why selling stock doesn’t ruin your retirement when you do it intentionally
• The difference between selling from a taxable brokerage account vs retirement accounts
• How to sell investments without panic, guilt, or unnecessary taxes
Why Selling Stock Feels So Scary
A lot of people believe that if they sell stock, it means they’re doing something wrong.
But most of that fear comes from not understanding how different investment accounts work.
For example, I only sell stock from my taxable brokerage account, not my retirement accounts.
That distinction matters because retirement accounts like Roth IRAs and 401(k)s are designed to grow long term without you touching them early. Taxable brokerage accounts, on the other hand, give you more flexibility.
I like to think of my brokerage account as the “side hoe” account in my financial life. My Roth accounts get priority because the growth is tax-free, but the brokerage account grows alongside them and gives me flexibility when I want access to money.
Why I Sold $5,000 of Stock
The stock I sold was VTI, a total stock market index fund.
I had originally bought those shares years ago for much less than what they were worth today. Over time, that investment grew by about 71%, which is exactly why I invest in low-cost index funds that track the market.
I didn’t sell because the market was crashing.
I didn’t sell because I panicked.
I sold because:
• The investment had grown significantly
• I wanted to increase my cash buffer for peace of mind
• I knew the sale would likely fall into the long-term capital gains tax bracket, which for my income level is 0%
This is why understanding your accounts and tax situation is so powerful. Selling stock can actually be tax-efficient when you know what you’re doing.
The Real Goal of Investing
Many people think investing means hoarding money forever.
But the real goal of investing is to build options.
Your investments grow so that eventually you can use that money to support the life you want. Sometimes that means retirement decades from now. Sometimes that means investing in yourself, your business, your health, or your experiences along the way.
Selling stock intentionally is part of that process.
Listen to the Full Episode
If this post resonated with you, listen to the full episode:
“How To Sell Stock and Still Retire Early“
🎧Listen to episode 139 of the Unicorn Millionaire Podcast on Spotify here
🎧 Listen to episode 139 of the Unicorn Millionaire Podcast on Apple Podcasts here
Want Help Understanding Your Investments?
If you log into your investment accounts and don’t fully understand what you’re invested in, you’re not alone.
A lot of people are investing in funds with high fees or confusing portfolios that aren’t actually growing as much as they could be.
That’s something I help my clients fix every day.
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.