Can getting lost lead to creative breakthroughs? In Episode 58, the Creative Work Hour crew shares personal stories about detours, mistakes, and surprises—both in art and life. Hear how embracing the “messy middle” can bring unexpected insights, new skills, and even joy. Listen for practical takeaways and inspiration from Alessandra, Greg, Devin, Shadows Pub, Michael J, Bobby B, Wai Ling, and Hillary.

Greg
00:00 - 00:15
Hello and welcome back to another episode of the Creative WorkHour Podcast. Today is episode 58. It is July the 5th, 2025. We just had the 4th of July or another name for that is Treason Day.

Greg
00:15 - 00:38
In the room today we have myself Greg, we have Alessandra, Devon, Shadows Pub, Michael J, Bobby B and Wai Ling. Today's question is an interesting one and it's can getting lost lead to an unexpected breakthrough? Alessandra when we were talking about this you gave some really good examples just before, can you go over one of those for us?

Alessandra
00:38 - 01:00
Yes, I would love to, Greg. Thank you. In the work that I'm doing in the portion of my life that is about music and music performance, I'm a clarinetist, a classical clarinetist, and my strength is as a soloist. What is not my strength right now is playing with other people in ensemble.

Alessandra
01:00 - 01:41
And there are those of us, like Devin, and you, and Michael, who have done work in ensemble, in music ensembles, and it is not the same as just doing your own solo thing. In fact, there are lots of places along the way when you are performing a work or rehearsing a work where you can just get flat lost. There can be changes in tempo, in time signature, in keys. and interpretation and you're supposed to leave out a section and skip over it and then repeat the one that was before it and there's the Da Capos and the Dal Signos.

Alessandra
01:42 - 02:07
It is wrought with like walking through a forest. You can just get flat lost. And that is what has been happening to me this year as I have been leveling up and as I was describing it to you earlier, Greg, I am so punching above my weight in classical music right now that I keep putting myself in situations where, where are we? Where the F are we?

Alessandra
02:07 - 02:29
Alright, so tomorrow is another performance, and as I've been reviewing the scores, these are the notes to myself that I have found, repeated over and over. And it's these few words. I got lost here. I've got it written right into the scores.

Alessandra
02:30 - 02:42
I got lost here. Now, on one hand, you could say, I screwed up here. But that's not how it feels. And look, I can be as hard on myself as anybody.

Alessandra
02:42 - 03:04
But that's not how it feels when I read those words on the score to do the skull practice for the performance tomorrow. What I read is, I got lost here. Therefore, it's important that I not hold on too tight to what I am doing individually. It's important that I listen to those around me.

Alessandra
03:05 - 03:29
It is important that I keep going. It is important that I don't presume That I know what I know. And there is this uncertainty that if I can just loosen the grip a little bit, I can fly and be part of something that's so much more important than doing it right. Because it's really not about doing it right, is it?

Alessandra
03:29 - 03:37
Creative work is not about doing it right. Creative work is about what does it want to be? What is arising? What wants to be said?

Alessandra
03:38 - 04:08
How does it want to be said? How does it want to be said when it's not just up to you, right? So, from the Practice Not Perfects, which are the twice a day sessions that we have amongst the crew of Creative Work Hour, for people to come and they can practice musically or they can give themselves extra time to work on, hell, a novella or artwork for Daily Echoes like Shadows does.

Alessandra
04:09 - 04:29
The thing is, it's about the experience. And what does a thing want to be? And when we're holding on, white-knuckled, we're choking off the circulation of that thing that is creative, of that thing that wants to be. So what is it about being open and willing to get lost?

Alessandra
04:29 - 04:39
And we'll see what the crew has to say, what they have experienced, or what they might be open to try. in projects that they're working on even right now.

Greg
04:40 - 04:57
Thank you, Alessandra. Yeah, it's about the journey, isn't it? I think if we get wrapped up in the rules of the game, we get to play. Talking about a journey, some of my best destinations I ever went to, some of the most interesting places I ever found myself were as a result of getting lost.

Greg
04:58 - 05:09
But I just kept going on. I'm like, well, let's see where we end up. And, you know, sometimes you're like, wow, you know, you discovered something you never would have a really cool place. But what about the rest of the crew?

Greg
05:09 - 05:14
Devin, can getting lost or off track lead to an unexpected breakthrough?

Devin
05:14 - 05:23
Hey, thanks, Greg. And absolutely. This conversation had me thinking about a line. You see it on a lot of bumper stickers these days, but it's originally from Lord of the Rings.

Devin
05:24 - 05:58
from a letter from Gandalf to Frodo, in which he says, all that is gold does not glitter, not all who wander are lost. And I have certainly found that to be the case in wandering, you know, can be a good part of the process. And I've really been trying to think of a specific example in my life. And this is not maybe directly on point of the examples that we're given, but I can be a bit of a Luddite and I resist new technology.

Devin
05:58 - 06:29
And one of the technologies that I resisted was anything that looked like a smartphone and apps and touchscreens. I literally, my flip phone had to be pried from my cold dead fingers when it broke and could no longer be used. And at that point I was encouraged by Alessandra to finally embrace the new technology. And that led to a series of discoveries.

Devin
06:29 - 06:45
And now that's my whole livelihood is working for a company that develops apps. And I had never touched an app in my life. And I swear to God, if that flip phone had been a little bit tougher and kept working, I'd still be using it today. But you know what?

Devin
06:45 - 06:59
I had to wander a bit and get lost in the technology of learn how to use something different. And it put me on a very different and very good path. So there's my one example of how wandering a bit could lead you to a better

Greg
06:59 - 07:03
destination. Thanks, Devon. That's a great example. Michael, how about you?

Greg
07:03 - 07:07
Can getting lost or off track lead to an unexpected breakthrough?

Michael
07:07 - 07:28
Sure can. Yeah. A few things come to mind here. I heard some story on YouTube recently about bees and apparently 80% of bees will sort of follow the queen wherever she goes right and then will sort of stay around but there's a sort of a 20% of the bee that are just sort of free electrons and they

Michael
07:28 - 08:06
sort of randomly go around and and it's always a lot those ones that keep the the hive alive because without them they would just be stuck in one place and never go from the predefined track and never find other sources of food maybe that are around. So that's kind of it's fun to explore off the track a little bit get lost, mind wandering. And for me, I guess in my creative journey, We could call it that. Yeah, the randomness has been important, and I've just sort of followed my instincts here and there.

Michael
08:07 - 08:43
Although often it was with a mix of the wandering and the structure, I guess, has been valuable for me, like having a daily habit, a daily expression, but letting yourself explore what that is. But having an expectation that you'll sort of produce something, let's say, whatever it might be. And I guess I spent some time wandering about through different things. It was, oh, I was doing doodles every day and then did that for a while and it led to Oh, me realizing how valuable that was the the artistic part, but wanting it to be more dynamic.

Michael
08:43 - 09:10
So branching into sort of like a streaming where the screen and then bringing in music and then realizing like, it's almost a podcast. So let's make it a podcast and then doing this for a while. And then so there's sort of, you know, the bit of randomness here and there that sort of bifurcates and gets you off of the Off of the beaten track while not beating yourself up about it I mean, it's it's easy and in retrospect to look back and say oh, yeah that doodle thing.

Michael
09:10 - 09:17
That was a failure. That was a disaster Thank goodness. I found this but at the time like the doodle thing was great. It was awesome.

Michael
09:17 - 09:36
It was fun. It was valuable It was dynamic. It was energizing so often it's maybe too easy to beat yourself up for having a Oh, look at all the random paths that I followed, and what have they done for me now? Nothing at all, but really, I mean, they were all valuable for you.

Michael
09:36 - 09:39
They've all brought you to where you are today.

Alessandra
09:40 - 10:02
I've loved your doodles, Michael. In fact, I think right in our Discord server that is the stuff that keeps us together in the asynchronous way that Creative Work Hour works, I think we have images of yours that are from some of those doodles. on on the white cards. Right.

Alessandra
10:02 - 10:17
And I think that that inspired Devin to start his own little white cards practice. And there's like he ordered the special box. He's like, yeah, I really like that thing that Michael was doing with the card. So I've ordered in some cards and here's my special box to put them in.

Greg
10:17 - 10:25
They were pretty cool. Bobby, how about you? Can getting lost or off track lead to an unexpected breakthrough? Oh, it sure can, Greg.

Greg
10:25 - 10:25
And it

Bobby. B
10:26 - 10:52
took me a long time to get to the point where I was willing to risk that, you know, to take that, put that toe on that pond and actually create a ripple, let alone follow it. But I'm so glad I have. I mean, part of that was my issues with memory and related things and not being able to even come back to where I was before I decided to branch out. And I've developed coping mechanisms that can take care of that.

Bobby. B
10:52 - 11:12
So for me, though, it's there's an intentionality that I need. And along with that, I have to have the humble confidence to say, you know, this is OK. Go ahead, try that weird-looking food item. Go to that location that's just, you know, curious enough to see what's there.

Bobby. B
11:13 - 11:37
And some of those jump out from an alleyway as I'm walking down the street. But to have that intentionality and humble confidence is the strength that lets me go there and realize, you know, you're going to be fine. And the other thing to all this is remembering to giggle. You know, when we're childlike and things like this happen, you know, we touch them, we look at them, whatever.

Bobby. B
11:38 - 11:50
And sometimes we release that discomfort as giggles. And that's important to me to this day. Just remember to giggle about it and move along.

Greg
11:50 - 11:54
Yeah, I remember to giggle. Remember to smell the coffee. I like that. Wai Leng, how about you?

Greg
11:54 - 11:58
Can getting lost or off track lead to an unexpected breakthrough?

Wai Ling
11:58 - 12:39
I love this question, and while I personally really believe in the virtue of getting lost, I also feel like I personally struggle with dealing with ambiguity that often comes in the process of getting lost. So when I was writing my dissertation, I have this term, I call it navigating the messy middle. Knowing like there's an end and a research question to tackle, but yet it is sifting through the data that can be really demotivating when you're not sure where you're going to go. But the one thing that I did was really just take one step forward each time.

Wai Ling
12:40 - 13:37
And then at the end of it, when I reflect on the whole experience, I actually come to learn new things that were totally unexpected and those insights were written into my dissertation like things like I would not have expect to find and learn and then they were there and that's when I really think like there is virtue when it comes to getting lost. I am personally in the midst of being lost as well having completed my dissertation and I'm in this job phase stage and really feeling like untethered, like I have nothing to hold on. I think the one way that I can describe is while I have the freedom, it is both Paralyzing and intoxicating at the same time because there's so much possibility, but yet it's also paralyzing.

Wai Ling
13:38 - 13:56
And I've recently started reading Anne-Laure Lecov. I hope I pronounced her name right. She's a neuroscientist. and she wrote this book called Tiny Experiments and she actually talked about why we humans get so uncomfortable in this process of getting lost.

Wai Ling
13:57 - 14:27
It's because we are all conditioned to have a very linear way of looking at goals, like you gotta do this and there's only one way to get there. But she proposed that there is a different way which is you set up what she calls tiny experiments. So instead of having a goal to achieve, your only goal is to show up in that tiny experiment. So it could be like, I want to write a newsletter, and your goal is just to show up to write 500 words a week.

Wai Ling
14:27 - 14:34
And that's it. And then after that, you keep gathering the data. Week 1, what does it tell you? Week 2, what does it tell you?

Wai Ling
14:34 - 15:05
and also have a deadline on when you want to stop these tiny experiments. So in a way she's proposing more holistic method of achieving what we want to achieve without having the linear way of looking at things. So it's constantly exploratory and it's not like directive like you gotta reach this one goal. Yeah so I'm in this phase where I'm trying to deal and manage my ambiguity and Feeling lost.

Wai Ling
15:05 - 15:07
So I really appreciate this conversation.

Greg
15:08 - 15:17
Thanks, Wailing. When you're talking about the tiny parts, I was thinking tiny desk concert. But how about you, Shadows? Can getting lost or off track lead to an unexpected breakthrough?

Shadows Pub
15:18 - 15:30
Since I spend most of my time wandering off whatever path I feel like going, I don't know that I could ever say I've actually got lost. Maybe he's deliberately losing. I don't know. I just take whatever path it seems to fit.

Shadows Pub
15:30 - 15:34
And if I can connect it back to what I'm doing, great. And if not, oh, well, I had a wonder.

Greg
15:35 - 15:49
Oh, Roselyta here. Coming in hot, Hilary joined us halfway through and we're discussing finding joy or pleasure in getting lost. Hilary, can getting lost or off track lead to an unexpected breakthrough? What do you think?

Hillary
15:49 - 16:03
I definitely think it can. Is there joy and pleasure in it? I don't know if I'd describe it as that. Yeah, it's like, you know, being open to getting results.

Hillary
16:03 - 16:42
So, you know, maybe you've got some intended results and you know, maybe like cooking a meal, but maybe you mistake an ingredient. I kind of did that once. Macon was a vegetarian manicotti, and instead I used, it's supposed to be a white sauce manicotti, and I ended up, I forget what I was supposed to use, but I ended up using cream of chicken in it, and it made a white sauce manicotti, and it was phenomenal. So I think that was one of the few times I, you know, was okay.

Hillary
16:43 - 16:57
With that kind of pivot, but often, you know, for me, we'll take this to something more intangible of conception of ideas. You know, I'm trying to produce, you know, like an S. O. P.

Hillary
16:57 - 17:07
for work. I find myself. getting pulled to other outcomes as I do the research. Like, oh, this could be good for that.

Hillary
17:07 - 17:33
This information could be good for that, but it's not the end result I want. And figuring out what to do with this extra bit of information that is valuable, but not to where I intended. That's, I think, one of my bigger struggles because you don't want to lose this little bit of value, but it can derail you from getting where you are trying to go. So hopefully you can be aware that it's not what you're going for.

Hillary
17:34 - 17:56
Capture it somewhere to the side. Recall that it's there later and then maybe do something with it. But usually it's just a big mess and I squirrel and nothing gets accomplished and it's just more mess to go through later as I try to get back on task. So that's, I guess, my opinion on that.

Greg
17:56 - 18:01
Thanks, Hilary. Alessandra, some great nuggets of insights in that.

Alessandra
18:01 - 18:31
I love what Hilary was talking about there, like, let's just be real, loss can be messy, and that can be stressful. And I love how, and I remember very distinctly when Wai Ling was talking about this a lot, the negotiating the messy middle. And what I remember is when she was working through that part of her dissertation, her research, she was just sloughing through this stuff, just day after day after day. You could just see the color draining out of her face.

Alessandra
18:32 - 19:03
But when she got to the point where she put those words together and started to describe it as negotiating the messy middle, the color started returning to her face. And I would hear her say things like, so I just have to keep taking the baby steps. I just have to keep going. So with that, you know, when we record these episodes for the Creative Work Hour podcast, there are more people who contribute to the episode than you actually hear their voices.

Alessandra
19:04 - 19:28
And one of those people is Rochelle. And Rochelle, she sits with us every Friday morning, the day before we do these recordings. And we really craft what topic wants to be discussed in this week's podcast. What wants to be what is arising amongst the group of us and how we create together.

Alessandra
19:28 - 20:14
And from that, We take notes and that the hour before we start to record, I go into a room with Greg and we really hash out and craft a succinct question to allow us to easily explore in a short amount of time. in the podcast, what's up for the week. So how I want to just put a recap on this, the beauty and acceptance of getting lost and the opportunities that it allows for us to have just a little, a little synopsis from Rochelle, which she jotted down so beautifully is she was like, here's the thing. And the beauty of getting lost is that it could totally work for you.

Alessandra
20:15 - 21:03
It can allow you to, as Weiling says, negotiate the messy middle, when you, A, can do your best to stay out of that monkey mind, that self-judgment, when you can keep reaching, keep stretching, and keep going, when you can listen to yourself and to those around you doing the work, recognize that you are doing it, Even if you feel stuck in the middle, you're actually doing the work. And there is this phrase that Devon uses that Rochelle has picked up on, and she loves it very much. And it's something that goes like, so whatever you're doing, even if you feel lost, even if you're stuck in the messy middle, allow for the possibilities.

Alessandra
21:04 - 21:09
See what happens. And most of all, just to keep a go. With that, I wonder, Greg,

Greg
21:10 - 21:20
what time is it? It's that time again. You've wasted some perfectly good time listening to the Creative Work Hour podcast when you could have been doing something else. But what about you?

Greg
21:20 - 21:29
What do you think? Can getting lost or going off track lead to some unexpected breakthroughs? Has that ever happened for you? Visit us at creativeworkhour.com.

Greg
21:29 - 21:35
We'd love to hear from you. In the meantime, come back next week and we'll be here with another discussion point.