
It took me almost three years to find a reason good enough to let go of my most profitable stock.
Three years of watching it fall and rise again. Three years of second-guessing every blip on the chart.
But last week, I finally pulled the trigger.
Not because of market signals or valuation targets. Not because of earnings reports or analyst downgrades.
I sold because I was ready to live a little.
When I started investing back in September 2022, I asked myself the same question every rookie does: when do I sell?
The truth is, there's no one-size-fits-all answer. I even wrote a column outlining five good reasons to sell, and I still missed this one: quality of life.
Sometimes, it’s not about squeezing out every last penny of upside. Sometimes, investing should support the life you’re building.
Exactly one week ago, I sold the final 20 shares of my Amazon stock. It wasn’t an easy decision. That stock had been good to me.
I had held it for 1,032 days — just shy of three years.
When the sale was complete, I locked in a $2,700 profit. That’s about a 155 percent return.
Not bad for someone who started this journey with more curiosity than confidence.
But the profit wasn’t the point. The point was what I did with the money. I almost couldn’t believe it.
I bought new furniture.
A living room sofa that doesn’t sag or squeak, one that finally makes the room feel like ours.
A kitchen table we’d needed for ages. The old one shook, leaned and squealed like it was begging to be retired. This one even has matching chairs. Now, the four of us can sit and eat together like the families you see on TV.
I picked up a few personal items, too — nothing wild, just things I’d been putting off. A plush comforter set for the harsh Chicago winter. Fingerless gloves for my Lil Mama, to help keep her warm.
The biggest purchase? A new laptop. My first personal machine in over a decade. Work has always supplied one, so I never bothered.
But lately, I’ve felt the need to invest in myself in ways that don’t involve the market or the gym. Owning my own education, building my systems, buttoning up the things that deserve attention.
This sale wasn’t about escaping risk or chasing a hotter stock. I’ll reinvest part of the proceeds into something that aligns with my goals. But I didn’t sell to reallocate. I sold to upgrade.
And that matters.
We spend so much time glorifying the grind: delay gratification, hold forever, compound endlessly. Those are powerful principles, but they’re not gospel.
The point of growing your money is to grow your life. To experience the reward, not just see a return.
Letting go of Amazon felt wrong at first. Like walking away from a sure thing. Like giving up my golden goose.
But what’s the point of gains if they never translate into a better life? What good is a portfolio full of wins if you’re still living like you’re broke?
So I chose to treat myself. To upgrade things for my family and our home.
Not extravagantly. Not recklessly. Just intentionally.
I gave myself permission to enjoy what I’d built.
And you know what? That’s the kind of decision I’ll never regret.
Why 'selling out' was a smart money move
Nine months after I said I would get rid of Realty Income, it’s finally done.
This feels illegal
I’ve made more money over the past 26 days from a single stock trade than I’ve generated by amassing shares of the same company for almost two years.
Disclaimer: The information contained on Money Talks is not intended as, and should not be understood or construed as, financial advice. I am not an attorney, accountant or financial advisor. These are my personal experiences, and neither this website, newsletter nor podcast is a substitute for advice from a qualified professional.
Nice work. That's the point of investing, to build and then enjoy. Amazon has had its ups and downs, maybe you will catch it again during another down and ride it back up or find something new. There's a whole world outside the big names to explore.