9 things people buy to look successful—but actually reveal insecurity

Let’s be honest—most of us want to be seen as successful.

There’s nothing wrong with that. Wanting to feel valued, respected, or admired is very human. But the problem starts when we try to signal success through stuff—especially when that stuff is really just covering up a quiet sense of not being enough.

I’ve seen it time and time again, both during my years in finance and now in conversations with friends, clients, and readers: we chase certain purchases hoping they’ll fill a gap. But instead of elevating us, those things often say more about what we’re lacking than what we’ve achieved.

If you’ve ever looked at someone’s flashy lifestyle and thought, “Wow, they’ve made it”—this post might have a few surprises for you.

Here are nine things people often buy to look successful… that might actually be revealing something deeper.

1. Designer logos (plastered everywhere)

Let’s start with the obvious: loud luxury branding.

There’s a reason the most powerful people in the world tend to wear understated clothing. Think about it—when’s the last time you saw Warren Buffett or Oprah in a giant monogrammed outfit? Subtlety signals confidence. Flashiness often doesn’t.

And brands are catching on. As analyst Yanmei Tang put it, “Hugo Boss’s repositioning has left it in a no-man’s land” because trying to appear aspirational through bold rebranding confused both high-end and budget-conscious consumers.

The louder the logo, the more it can scream “I’m trying too hard.” Quiet confidence doesn’t need labels to prove its worth.

2. A luxury car lease (that stretches the budget)

This one’s tricky.

A nice car can absolutely be a practical choice. But when someone’s struggling to cover rent while leasing a new BMW? That’s not power—that’s pressure.

Some of the wealthiest households drive what most would consider “ordinary” brands. According to Experian Automotive, 61% of households earning over $250,000 drive Hondas, Toyotas, and Fords—not luxury vehicles.

I used to work with clients who made seven figures—but you’d never guess it by their cars. One man I worked with drove the same Toyota for ten years. His reasoning? “The less money I put into appearances, the more I have for real freedom.”

That mindset says a lot.

3. “Power watches” or over-the-top accessories

I’ll admit, I used to think a watch said a lot about a person.

Then I started noticing a pattern. The ones who flaunted $10,000 wrist candy were often the same ones stressed about meeting end-of-month expenses. It was as if the watch was supposed to distract from the chaos behind the scenes.

Of course, there are watch lovers who genuinely appreciate craftsmanship. But when an accessory becomes a tool to manufacture identity—or mask insecurity—that’s when it starts speaking louder than intended.

This point reminded me of something I read recently in Laughing in the Face of Chaos by Rudá Iandê. His insights made me reflect on all the ways we perform success rather than live it.

One line especially hit home: “When we let go of the need to be perfect, we free ourselves to live fully—embracing the mess, complexity, and richness of a life that's delightfully real.”

That quote made me rethink how often we trade authenticity for appearance.

4. The “perfect” home decor

Ever walk into a home that looks straight out of a showroom?

No fingerprints on the fridge, no mismatched mugs, no visible signs of actual living? It can feel more like a staged Airbnb than a place someone truly relaxes in.

And while it might photograph beautifully for social media, sometimes that level of perfection tells a different story.

I’ve known people who felt deep pressure to keep their homes looking immaculate—not because it brought them joy, but because they feared being judged. They didn’t feel successful unless their space “proved” it.

But here’s the irony: truly confident people don’t feel the need to prove anything through curated aesthetics. They might have a quirky bookshelf or a wall full of photos that don’t match, and they’re not trying to impress anyone with it.

A clutter-free space can be wonderful, sure. But if your home looks more like a showroom than a sanctuary, it’s worth asking—who am I really decorating for?

5. Trendy rebrands of your identity

From minimalist capsule wardrobes to full-blown “boss babe” aesthetics, we’re living in the age of the personal brand.

And while evolving your style or exploring a new version of yourself is a beautiful thing, there’s a difference between genuine change and a trendy costume worn to gain approval.

I say this as someone who once spent an uncomfortable amount of money “reinventing” myself during a rough patch in my career. New outfits, new photos, new taglines…same inner confusion. The shift looked good on the outside, but it didn’t feel honest.

When your transformation is driven more by social optics than by self-awareness, it can actually widen the gap between who you are and who you’re pretending to be.

The most magnetic people I know are the ones who are grounded in who they are—even when that doesn’t fit the trend.

6. High-end wellness products

Let’s talk about the $300 face cream. Or the $70 water bottle. Or the supplements marketed like sacred relics.

Wellness has become a luxury industry—and while there’s nothing wrong with wanting to take care of yourself, the way we buy into it sometimes has little to do with actual health and more to do with how we want to be perceived.

I’ve seen people rack up credit card debt in pursuit of “optimized living.” Behind the collagen powders and infrared gadgets? A quiet voice whispering, “Maybe if I fix this part of me, I’ll finally feel good enough.”

But the confidence we crave doesn’t live in a fancy serum or high-tech blender.

Some of the healthiest, most grounded people I know keep their routines incredibly simple. They know that true wellness isn’t about showing off—it’s about how you feel in your own skin when no one’s watching.

7. The latest phone or tech gadget (every year)

There’s always a new model.

Slightly faster. Slightly sleeker. Slightly shinier.

And yet, the minute we unwrap it, the clock starts ticking on its status. What was once the “new thing” becomes old news within months. That’s how the cycle works—it thrives on insecurity.

When someone upgrades their phone the second a new one drops—not because their old one broke, but because they feel behind if they don’t—it’s not about the tech. It’s about the story they’re trying to tell.

A client once told me that every time he got a new device, he felt “relevant again.” That’s a lot of pressure to put on a piece of metal.

If you're buying it to feel current rather than because it solves a problem, that might be worth exploring.

8. Expensive memberships and status-based subscriptions

Whether it’s an elite gym, a private wine club, or a VIP credit card with an eye-watering annual fee—some memberships are more about the bragging rights than the benefits.

Don’t get me wrong. If a service truly adds value to your life, go for it. But if you’re barely using it—or if you’re only keeping it because it sounds impressive to others—it might be worth asking: what am I actually paying for?

I once had a colleague who joined an exclusive co-working club. Beautiful space, yes. But he worked from home most days. When I asked him about it, he admitted, “It just feels good to say I’m a member.”

When your identity leans too heavily on the perception of success, you end up paying for a lifestyle that doesn’t even feel like yours.

9. The curated social media aesthetic

This one doesn’t come with a price tag at checkout, but make no mistake—it costs something.

I’ve watched so many people carefully build an online identity that reflects the life they want others to believe they have. The right filters. The inspirational captions. The staged “candid” shots.

It’s an exhausting performance—and it rarely reflects what’s really going on behind the scenes.

We all know this intellectually, but still, it’s easy to fall into the trap. I’ve done it. I’ve posted the “perfect” moment while feeling anything but grounded in real life.

And you know what? The likes didn’t make me feel any more successful. If anything, they just made me feel like I had something to maintain.

If your “highlight reel” is hiding a lot of heaviness behind the scenes, that’s not success. That’s pressure dressed up in pixels.

Sometimes the most radical thing we can do is show up as we are—with joy, yes, but also with imperfection, nuance, and mess. The real stuff.

Final thoughts

Here’s the hard truth: insecurity sells.

It sells handbags, car upgrades, premium memberships, curated homes, and $150 skincare routines. And often, we don’t even realize we’re buying into it.

But here’s the good news: the moment you stop trying to look successful is usually the moment you start feeling it.

Because real success has very little to do with what you own and everything to do with how at peace you feel when the doors are closed and no one’s watching.

If you’ve recognized yourself in a few of these points, don’t panic. I did too when I first reflected on them. That’s the gift of self-awareness—it shows you what needs attention, not what needs fixing.

You don’t need more polish. You don’t need more stuff. You just need more truth.

And that begins with letting go of the performance.