4. Useless Midnight Portfolio Checks Have Made Me a Better Investor

My first year of investing: down 10%, checking my portfolio at 2am, and convinced I was doing everything wrong. Turns out, I was doing everything right and simply learning to stay consistent.

My phone screen lit up the dark bedroom. 2:17 AM.

There’s something almost funny about staring at a red number on a screen at midnight, knowing the market is closed, knowing absolutely nothing will change until morning, but still not being able to put the phone down.

Nothing had changed since I checked before dinner, or before bed, or twenty minutes earlier when I told myself that one would really be the last. The numbers would be the exact same shade of red they’d been all day.

Welcome to New Investor Syndrome, a very familiar phenomenon for everyone who’s ever put real money into the market for the first time. The strange magnetic pull toward information you know won’t help you, delivered by apps that definitely shouldn’t be opened at midnight. 

Although I seriously did my due diligence before starting my investing journey, no one could’ve prepared me for the sheer obsession of seeing my own money move in real life. Fortunately, once the obsessive checking phase faded, I realized I came out of it a much better investor than before.

Podcast Preparations

I didn’t start my investment journey the moment I graduated university and received my first salary. Instead, I spent almost a full year listening and learning about investing.

A close friend had recommended a Dutch podcast, Jong Beleggen, and its premise was brilliant: a young entrepreneur had just sold his company and was investing the proceeds in real-time, documenting every decision and every feeling along the way. Each episode covered some of the basics of investing, the state of his portfolio, and most importantly, how the inevitable volatility actually felt from the inside.

I listened religiously while commuting, cooking, and doing laundry. It became the background noise of my daily life and slowly, without realising it, I was getting an honest picture of what investing actually looks and feels like: the anxiety when numbers turn red, the temptation to lock in losses, and the discipline of staying still when every instinct tells you to act.

One episode really stayed with me. The host’s portfolio had dropped several thousand euros in a single week, and his social circle had sent him some pointed messages about the wisdom of his choices. But when he talked about it on the podcast, he just sounded… fine. Not thrilled, obviously, but calm and grounded. “This is what markets do”, he said. “I’m not selling”.

The listening gave me the confidence to make a start with investing. I understood the basics, and if the podcast host could handle thousands disappearing without losing his composure, I could probably see hundreds evaporate without losing mine.

Bearish Beginnings

I finally opened my investment account in April 2022, once I had enough financial breathing room to commit €500 a month without touching my emergency fund. The plan was straightforward: a globally diversified ETF as the core and a couple of thematic ETFs for personal interest, followed by a lot of patience.

The market, however, had other ideas.

My portfolio immediately started swinging in ways I hadn’t expected, even after that year of preparation. Three months in, I was down 10%. Five months in, somehow up 15%. By year’s end, 11% in the red. I’d started my investing journey right at the beginning of a bear market, excellent timing if your goal was to be immediately tested.

It was here where the year of listening earned its keep. Because when the first 10% drop arrived, I could listen in real time how the podcaster reacted to the events. He’d lost thousands and hadn’t sold, whereas I’d only lost hundreds.

It was a welcome perspective on events, because I’d become so obsessed with watching my money move that I probably would’ve made some seriously unwise actions without it.

The Obsessive Checking Phase

My portfolio showed more mood swings than a teenager on Red Bull, and I was watching it like a social media feed. Morning checks, lunchtime checks, before-bed checks, and the occasional midnight checks just to confirm that nothing had changed since the before-bed checks.

The temptation to sell was absolutely there, and I actually came very close on multiple occasions. That voice telling you to sell now, stop the bleeding, wait for things to stabilize, and then get back in at a better price, is a very persuasive one. It sounds so reasonable when your portfolio is down and you’re consistently being confronted with red numbers.

But I also knew, strengthened by continuing to listen to the podcast, that selling locks in losses and that bear markets eventually recover. That financial decisions made after midnight checks with your emotions running the show are seldom the ones you’d make at 10am with a clear head. It was like a friend telling me to 'be better than the Gap' and giving my wardrobe a complete overhaul, but instead of dressing for success I was mentally preparing to handle red numbers without panicking. 

And slowly, over time, something shifted. The red numbers started feeling less like catastrophe and more like information. Uncomfortable information, sure, but information that didn’t require a response because the numbers didn’t matter until years later anyway. The market simply did what it did. My job was to just keep investing and otherwise leave it alone, staying disciplined even when my instincts screamed to tinker. 

I’m happy I stayed the course, but it wasn’t until late 2023 – one and a half years after I started my investing journey – that my portfolio stayed green for good. Looking back, it was exactly the gradual adaptation of seeing red without reacting that had kept me invested long enough to get there.

Becoming a Proper Money Stoic

In hindsight, all the money invested until I left the red numbers for good was learning money. All those days with red numbers weren’t losses, they were lessons I was paying to learn. Lessons about how I actually handled volatility and pressure, when it was my own money on the line and my brain was making very compelling arguments why selling was the best thing to do. They’re the kind of lessons most personal finance content will never be able to prepare you for. Instead, you have to pay for them with your own money, emotions, and sleepless nights.

What those months listening to the podcast and staying the course quietly built, I didn’t realize until much later, was a more stoic relationship with money. The ability to feel the anxiety, observe it clearly, and deliberately choose not to act on it. I could handle volatility with my own hard-earned money, not theoretical calculator money from a practice portfolio. When I got a nice promotion at work, the confidence that came from that eventually allowed me to comfortably double my monthly contributions without thinking twice. Without having paid that learning money upfront, I don’t know if I ever would’ve been able to do that.

And that’s the education no personal finance content mentions when it tells you to start investing early. Your first year isn’t about the returns at all. It’s about finding out who you are when your money is doing things that are completely out of your control.

Turns out, I was someone who obsessively checked his portfolio at midnight and still didn’t sell.

I’ll take that.