Do you ever have something just pop into your mind, and suddenly you’re like, “Ahhhh…”?
Like, something that’s been sitting just under the surface finally clicks, and you think, “That makes so much more sense now,” or “That’s the real root of the problem.”
Over the past few years, I’ve been helping teachers gain calm, clarity, and confidence in their digital lives. And there’s one theme I’ve noticed again and again. But it didn’t fully click until just this past week during a mini-consult with a teacher.
That’s what we’re going to talk about in today’s episode—number 167 of The Piano Pantry Podcast. I’m your host, Amy Chaplin, a piano teacher whose goal is to help you find practical and sustainable rhythms for your teacher life.
A quick shout-out to Patreon member Valerie Evenson for cheering on this work over on Patreon. If you’re benefiting from this content and feel inclined to support it, I invite you to join me on Patreon as a silent partner for just $4/month. For a few more dollars, you’ll receive some fun kickbacks as a thank-you from me.
Now, onto today’s episode.
Let’s rewind a little. There are two moments in particular—both with teachers I’ve coached—that brought me to the realization I want to share with you today.
The first moment happened during episode #160 this past summer. I was chatting with teachers who attended the digital organization retreat I hosted in my home in late May.
I asked one attendee to describe what her digital work life looked like before the retreat and whether there was a moment when she thought, “There’s gotta be a better way.”
She shared that she’s a bit technology-averse. She’s not someone who jumps on the latest gadget or downloads the newest app. She’s also not the kind of person who says, “Oh, I’ll just Google it.”
She really just wanted someone to hold her hand and walk her through it.
And I replied—half-joking but also completely serious—“So I Googled stuff for you.”
We all laughed, but it was true. That’s literally what I did. She’d ask a question, and even if I didn’t know the answer off the top of my head, I’d do a quick search and bam—there it was.
Afterward, she’d often say something like, “I can do that… but I just don’t. I’m not wired that way.”
Now, this wasn’t shocking to me—I’ve helped something like 150 teachers rethink their digital lives. I know that for many of us, especially creatives, the tech side of our professional lives can feel unnatural or overwhelming.
But even still, I kept wondering—why is it that something so intuitive for one person can feel like a complete roadblock to someone else?
It was one of those little questions that lingered quietly in the back of my mind—until this past week.
I had a mini-consult with a teacher who had previously attended my retreat. She reached out because she was missing some audio files she knew she had, but couldn’t find on her Mac.
She used to access them through iTunes, but ever since it switched to Apple Music, they seemed to have disappeared.
So we did some digging—searching in her iCloud Drive using keywords—and we found one of the files, buried eight folders deep. Not only that, but it was a WMA file—a Windows Media Audio format.
Here’s the thing: WMA files don’t work with Apple’s QuickTime or Apple Music app. You need a third-party tool to play or convert them.
Now, I have a general understanding of audio file types, but I wasn’t 100% sure about QuickTime compatibility, so during our consult, I started Googling a few questions to help us figure things out.
And that’s when she said something that stopped me in my tracks:
“Sometimes it’s just hard to know what to ask.”
That was it.
Suddenly, that earlier conversation from episode 160 made sense in a new way.
Sometimes it’s not just about being “bad with tech” or being too busy or disorganized. Sometimes the roadblock—which we may not even always realize is a roadblock—is not knowing what question to ask.
My friend Christina Whitlock often says on her podcast:
“Sometimes the thing you think is the thing… isn’t really the thing.”
And in both of these situations, that rang so true.
In the second teacher’s case, the issue seemed to be that the files were missing—but that wasn’t the only issue. The files were there, but they were in a format her system couldn’t read. We couldn’t ask the right question until we’d done some digging.
She was right—in her case especially—it really was hard to even know what question to ask.
Most of the time, though, when you feel stuck, my practical answer on how to ask the right question of Google is to just type out the question exactly as you’d say it to me.
You don’t need techy language or the “right” keywords. I can’t tell you how many times during a retreat someone will ask me a question, and I’ll literally repeat their words out loud as I type them into Google—which always emits a chuckle from the group—because it is kind of funny—and we get an instant answer.
I wish I had kept some kind of record of the kinds of troubleshooting we’ve done in these digital organization sessions, but of course, I don’t because they just happened in the heat of the moment, so I’m going to try to describe a few similar types of questions I’ve heard over the years.
These aren’t all necessarily ones that I had to Google to find answers to, but they are perhaps questions that, if you were wondering, you could type into Google, asking it exactly word for word like this, and you would quickly get an answer.
Simple, conversational questions. But each one could lead you directly to what you need to know.
And in the second teacher’s case, once we understood what we were dealing with, we were able to ask more specific questions like:
So the thing we thought was the issue—missing audio files—was not the thing. It wasn’t the whole story. It was because they were not in a format readable by her audio player.
I’m not saying any of this to make anyone feel bad or to make you feel like you should just be able to figure everything out with Google. I just want to encourage you not to let the roadblock of “not knowing what to ask” stop you. Just use your words—exactly how you’d say them if you were asking me face-to-face.
If you’re like my second teacher friend and have something that really has you stumped, and you could use a little help getting past a roadblock to the point where you can even ask questions, I have three mini-consultation times available this last week of September 2025.
They’re just $35—a special one-time offer I sent to my email subscribers earlier this month. It’s the first and probably only time I’ll offer consults at this price point. So if you want one, grab it now! The link will be in the show notes.
If you missed this offer I sent out earlier this month, because you’re not on my list, be sure to sign up at pianopantry.com/subscribe.
If you could use more calm, clarity, and confidence in your digital work life, join me for the Fall session of my newly rebranded coaching series:
Organize Your Digital Life: A Refresh for Your Digital Workspace
It’s a 2-month series where we meet weekly—Tuesdays, 1:00–2:30 PM Eastern, starting October 21. Each session blends learning with real-time implementation, so you leave feeling more confident and in control.
Register by October 15 at pianopantry.com/digital
Use code DIGITAL20 to get $20 off before October 1.
Spots are limited and we need a minimum number to run the class, so don’t wait!
I normally try to mix up my episode topics a bit more. Last week, I also focused on digital organization—specifically, file naming tips—but this topic had been nagging at me a bit, and I always feel like my best work comes when I incorporate what’s happening in my own life as much as possible. I hope both of these episodes have resonated with you.
Thanks so much for joining me today. If this episode helped you feel a little more equipped or encouraged, would you consider subscribing, rating, or leaving a review?
It really helps others find the podcast—and it means a lot to me.
Until next time, friends.
