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4 Smart Strategies for Buying Tech for Your Teen

A teenager wearing wireless headphones stares out of a window onto a city street.
How to go about buying expensive technology for your teenager can be confusing and often a challenge. Here’s what I do.

We all know how expensive personal tech can be. The price points don’t change for your kids and teens. Tech is tech.

As a parent of a teenager in high school, it’s already been a couple years since I faced the reality that toys are for kids, and he’s not really a kid anymore. When I shop for our son, he wants (and often needs) the same tech as I do.

That said, the gear we all use is often available at a variety of price points. So, when shopping for our teen, yes, I’m inclined to first look at the lower end, but I’m also mindful to get him something ‘good.’ 

I don’t want to fall for ‘a deal’ on a model that’s subpar. A bargain is not always good value in the name of trying to save a buck. Not for me. Not for my boy.

So, I do find it a complex balancing act as a parent, and I must admit I carry some baggage to this shopping equation.

My Father Got Me Used Tech
I recall the moments my own father gifted me the tech I craved when I was a kid… a stereo system for my room and later a cool Sony Walkman. What I also still remember was the stereo was in an already-opened box, and my Walkman had an annoying dent in its metal frame (but it worked fine).

Not to diss my dad, who passed away in 2022, but the memories of these slightly used gifts still kick around the back of my brain. 

Sure, he was probably going through the same questions as I am now as a father. And he made some choices. And just so you know, it wasn’t an affordability question. There are a few other details, but they don’t change the facts. Nor do they blunt these feelings decades later.

Finding a deal for yourself is one thing. Shopping for a discount for someone else’s gift can be entirely different. As we go through this topic, I just wanted to reveal this story as I share my own gifting strategies as a dad.

Of course, I look for reasonable and smart ways to buy tech more affordably for my son. But I also don’t want to repeat the gifting mistakes my father did.

So, all this said, here are four ways I’ve been trying to navigate this tech terrain as a father…

#1
Start at the Entry Level

As any number of tech product categories mature, less expensive versions eventually show up. They’re usually not as good. But sometimes… they’re almost as good and often in the ways that matter most. And that’s where I look for gifting opportunities.

I like this approach especially with the brands we already know and love. Apple’s iPhone SE is a great example, and yep, my son has one. I actually bought it for myself as a ‘transition phone’ after I drowned my old iPhone. (That’s a whole other story.) Later, the SE went to him.

Not every entry level choice is the right move. You’ve got to do some homework.

#2
Shop for Yesterday’s Best

Sometimes, last year’s model at a discount is still a great choice. How much better is the newest version really going to be?  

And most importantly, last year’s great model can be a much better choice than a cheaper model that’s brand new. Shopping for price is only one piece of the equation.

I recently applied this shopping strategy for a pair of noise-cancelling wireless headphones for our son.

I went with the older Bowers & Wilkins Px7 S2 Over-Ear Headphones. They received amazing reviews. But there’s a newer model: the Px7 Se. Yes, that’s the latest-and-greatest (unless you must have the even more expensive Px8).

But the discontinued Px7 S2 was still for sale and at a nicely discounted price. So, I bought it. 

I think the Px7 S2 was a really solid choice. And most importantly, my son loves his new headphones.

Always remember to take a look at yesterday’s best.

#3
Don’t Skimp on the Guts of a Computer

We’re an Apple family. So, of course my son has a MacBook. I got him the MacBook Air. No… not the more expensive MacBook Pro. But I made that choice also because the MacBook Air is so good. And I bought the current model at the time. 

Sure, I could have saved a couple hundred dollars on last year’s model. But in this circumstance, I didn’t follow my ‘yesterday’s-best’ strategy. I applied a different shopping strategy for computers. 

I always like to buy the current model with the newest chip. That choice can help the laptop last at least an extra year or more at the back end of its life cycle.

Same rule for me and our son.

#4
Brand Often Matters

Not every model that a well-known brand sells is going to be good. Again, you’ve got to do your homework. But if you’ve got to put your trust somewhere, I think it’s smart to stick with the brands you already know. 

This may seem like an obvious point when it comes to big-ticket items, but for any number of accessories, you’re going to come across plenty of manufacturers you don’t recognize.

Be careful. I’d say it’s not worth taking the risk to save a few bucks. Sure, there are exceptions, but there’s already a fair amount of playing the odds when you shop. Why not stack the odds in your favor?

Shop Smart
Buying tech for your teen should follow the same smart shopping strategies for any purchase:

  • Identify a quality product.
  • Only get the features you need.
  • Then find a good price.

Of course, there’s always the hand-me-down strategy (like My iPhone SE). Nothing really wrong with that (although teen Barrett would probably have taken issue with it).

But if you’re making a purchase, yesterday’s best is usually the perfect place to start your search.

How to Update Account Settings on Apple Watch Using your iPhone

Trying to type into Apple Watch keyboard
Stop trying to sign into your Apple ID using your Apple Watch’s micro keyboard. Your finger is probably way too big for this. Here’s the better way to get the job done.

I don’t like messing with my Apple Watch. I’ve set it up to do what I want, and I usually don’t dig in to change the settings. The screen is so tiny. Yes, its interface is clever, but it’s not much bigger than a postage stamp. 

And that’s fine. It’s a watch… not an iPhone. 

Sure, it’s similar to iPhone in certain ways and is best tethered to one. And I can easily interact with it using the Digital Crown and side button.

But please don’t ask me to type anything into my current Apple Watch Series 9. That’s absurd. Yes, you can call up a cute micro keyboard to use. But come on… My index finger takes up 30% of the entire surface of my Apple Watch. 

Update Apple ID Account Settings on your Apple Watch
But that exactly what my Apple Watch sometimes asks me to do after a software update. I’m supposed to log back into my Apple ID account. And then my Apple Watch presents me with its tiny keyboard. Are you kidding?!  

My finger’s surface area can press onto 3 keys easily… so tapping away gives me about a 30% chance of keystroke success. (And the tiny scribble pad? That’s no better.) 

So recently, after failing to sign into my Apple account after multiple miss-tapping sequences, I looked for another way in…

Use your iPhone Instead
If you think your iPhone can help, you’d be correct. Strangely, I couldn’t quickly solve this tech challenge by Googling it, but eventually I found the clue. Here’s how it works:

  • You simply need to activate your sleeping iPhone right after your Apple Watch prompts you to micro-tap your password. 
  • Immediately, your iPhone will come to the rescue and open a thin text-prompt window on its own screen for you type into. 
  • And as you do that, your password will magically mirror onto your Apple Watch’s screen. Done.

So obvious, right? (The solution is already baked into the Apple Watch/iPhone relationship.)

No More Micro Tapping
Perhaps the whole world already knows this trick. And if it’s just you and me who’ve finally caught on, so be it. (I won’t tell anyone.)

But now, my finger will never again attempt the absurd micro-tap dance on my Apple Watch. 

It’s a micro win… but a win, nevertheless.

Here’s a Great Place to Snap a Photo of Manhattan’s Iconic Skyline at Sunset

It’s hard to miss this famous skyline as your Amtrak train nears or leaves the Big Apple. And sunset is a particularly special time. So, it warrants trying to take a photo or two…

The weather conditions have to be right. Plus, there’s only a six-minute stretch when the train is close enough and oriented correctly with its windows directly facing the east side of Manhattan. 

The Best Views of New York City
Then, take out your smartphone. Press it as close to the window as possible to avoid reflections from the inside of the train. (The fact that your phone’s lens effectively lies flat with the phone’s body will protect it from accidental bumps into the glass due to your train’s jerky movements.)

And then start snapping away.

As much as I always want to zoom closer with my iPhone 15 Pro Max’s 2x or 5x lens to better frame the skyscrapers, the wider shots are better. I think you need that foreground in the shot to help tell the visual story. Plus, the train’s motion is less of a problem for your phone’s camera if you’re not zoomed in.

Just Another Bonus for Taking the Train
Yes, it’s an amazing vista to take in, but you should temper your expectations for your photos. Remember, you’re shooting through glass, and the train is moving.

Still, it’s worth a shot.

I go for it whenever I’m on Amtrak’s Northeast Regional or Acela heading back to Connecticut from Washington, D.C. (These photos are from my recent trip.)
In the old days, it would be when I was heading out of New York City back to Boston. (So, I’ve been at this for a while.)

And yes, I do prefer taking the train vs. a plane between these destinations. It’s much more convenient and relaxing. (The door-to-door time comparison is similar after you bake in the extra hours spent at the airport.) But I digress…

Enjoy the Show
Sunset isn’t the only time to try to capture these photos of New York City. (Shooting directly at the sun can really confuse a camera and isn’t especially great for its sensors. But a few brief clicks shouldn’t play too much havoc with the electronics.)

These magic sunset minutes always call out to me as the deep orange light bathes the landscape. 

It’s both unearthly and entirely natural.

And you’ve got one of the best vantage points of this city a photographer could hope for.