A candid, practical conversation on “future-proofing” creative work across personal practice, small businesses, and communities. The team frames future-proofing as resilience and continuity: shared access and roles, documentation and training, and planned breaks that keep momentum without burnout. They discuss using AI to turn fuzzy ideas into actionable plans, navigating modern IP protection, and designing legacy paths so work can continue beyond a founder. The emphasis shifts from daily volume to building a sustainable flywheel and a community “insurance policy” that outlasts any single person.

Greg
00:00 - 00:13
Hello and welcome back to another episode of the Creative Work Hour podcast. Today is episode 68, not 78 as I falsely reported earlier. I got a little bit ahead of ourselves with that. A little bit too eager and ambitious.

Greg
00:13 - 00:37
But today's topic is how do you future-proof your creative work? When we say your creative work, it could be your own personal creativity and how you do future-proofs, you know, staying creative. Or if you are a small company or business, then to you that might look like how do you future proof your business, whatever your creativity looks like to you. Alessandra, interesting topic.

Alessandra
00:37 - 01:12
This comes up because when I am in a point of struggling to get out my creative work, be it because something has happened that's disruptive or Maybe I'm dealing with just having really low energy or it's fatigue, or it could be like in case of creative work hour, we don't have enough hands on deck to run what we're doing for creative work hour. So I'm not much of a manager. Like I don't have managing skills.

Alessandra
01:12 - 01:25
Like I'm a good robot. I can take orders, but I have a hard time managing a group of people. I always avoided being the boss. So here we are at creative work hour.

Alessandra
01:25 - 01:52
We've done this for more than 3,000 sessions now. And the first couple of thousand, I was okay. This last thousand, I'm not so okay because I'm trying to do my own creative work and I haven't future-proofed creative work hour. That is this group that comes together every day so that we support each other in creative work, getting things out there.

Alessandra
01:52 - 02:15
And a big part of the energy of this is that when one of us gets something out there, we all celebrate. right? And that's the feedback loop of how we keep it going. But I see that I don't have a flywheel, as the founder, I don't have a flywheel for creative work hour.

Alessandra
02:16 - 02:38
So I was sharing with you, Greg, and with Shadows earlier, that I get quite concerned about How will we future proof creative work hour? So this is not a post, this is running a community. That's my number one creative work. How do we future proof it when just one person cannot do this?

Greg
02:38 - 02:40
Right. It's a challenge, isn't it?

Alessandra
02:41 - 03:13
It's a real challenge. And one of the things that's been suggested to me is, do you have where everybody sits down and the only thing that we're doing in that session is discussing together, how do we future-proof Creative Work Hour? So when we choose topics for our podcast, it's because we're really working in real time of how to fix stuff. or getting an awareness of how do things affect our creative work?

Alessandra
03:13 - 03:21
Yeah, so that's what I'm tackling with right now. So I thought, why not have this as the topic of discussion today?

Greg
03:21 - 03:54
Thank you, Alessandra. Yeah, you know, I struggle with the same thing as we talked about earlier with myself. I have support groups that I run for mental health, for brain injury, and chronic pain, then there's my kindness community, which I'm building on GoBranch and asynchronously. And I'm not, because I'm fatigued a lot, which I'm trying to get to the bottom of, but I'm not spending the time nurturing those communities, growing them, promoting them, forming, you know, strategic partnerships and alliances and things of that nature, which, you know, that's kind of my creative

Greg
03:54 - 04:47
endeavor at this time is that community, like yourself. And so for me, that would be what that looks like but you know future proofing could look like any number of things if you're you know a solopreneur you know freelancer that's going to look different than if you're a small business or organization and then there's your personal creativity and then there's the you know creativity and continuation of the business as well and that might mean you know making simple things such as you know making sure that there's key players in responsible positions that have the the keys to the store as it were and things of that nature but it's not to oversimplify anything but Bobby what about yourself when it comes to your creativity or how you envision future proof in your creativity or what that looks like for you or even what that you know might look like for creative work hour what

Greg
04:47 - 04:51
are your thoughts or what comes to mind on that topic Bobby Wasserman?

Bobbie W
04:51 - 05:09
For me, I know that what's been helping me lately because everything is changing so fast is actually using new tools that are coming up, right? And so you take what you know and you incorporate these new tools and it brings you to a whole new level. So that's especially with AI.

Greg
05:09 - 05:16
You're talking about the pre-verbal prompting is something that you were talking about. Yes. Oh my gosh. That gets you excited, right?

Greg
05:16 - 05:16
I was

Bobbie W
05:17 - 05:17
so excited about

Greg
05:17 - 05:17
that.

Bobbie W
05:18 - 05:54
It gave me what I needed. I knew in my head what I wanted to do. Translating it into language that was going to incorporate new tools and new thinking and the new vision of business was where I was having problems stumbling. So that AI bridge that takes you from what's in your head and what you know in the language that you know, right, and in your experience that you know, that new technical bridge can take your same ideas, add the nuances of today and get you where you want

Bobbie W
05:54 - 06:00
to be. So that's, you know, it's especially now, it's just business is changing so fast.

Greg
06:00 - 06:10
Bobby, could you give an example of what, if you're able to, what might a pre-verbal prompt look like or what does that actually mean?

Bobbie W
06:10 - 06:46
So my understanding, which, you know, up to interpretation, my understanding with these pre-verbal prompts is being pre-verbal, having the idea that hasn't quite crystallized, right? So it's just kind of bubbling under the surface. And using different AI prompts, you can identify that. If you're talking about something that is in the lexicon and people are implementing, the pre-verbal is something that you've got this idea, it's relative, it's new.

Bobbie W
06:46 - 07:05
That's a dangerous word, new. But it's new and then it still needs to be crystallized and formed into something coherent that can be talked about, right? So yeah, so these pre-verbal prompts have been really helpful for me.

Greg
07:05 - 07:26
Right, because language and learning and pre-verbal I think about, you know, child development and language models are a language model, right? Because I mean verbalized if you can get in right before it's verbalized and manipulate in that in some way I can see how that would be incredibly beneficial and creative. But Bobby B, how about yourself? How do you future-proof your creative work?

Greg
07:26 - 07:30
What does that look like for you and what might that look like for creative work, Howard?

Bobby. B
07:30 - 07:58
It's a real interesting question, and I'm not sure I have a good answer. You know, because all creativity comes from influences from everywhere. When I think of future-proofing, I go to protecting the content that I have uniquely constructed and that someone else would take bits and bobs from and construct for their future. So yeah, I just really can't say I'm very good

Greg
07:58 - 08:05
at it. So when you're saying content, you could be referring to intellectual property as content, right? And that's how I'm taking the question.

Bobby. B
08:05 - 08:06
Yeah.

Greg
08:06 - 08:19
So when you were in your management field and your creative side of being in management or the creative side of that business or enterprise, how did your proofing, what did that look like in that wrapper, in that scenario?

Bobby. B
08:19 - 08:40
Well, now that's a great question. I retired from that industry 12 years ago, before AI, before a number of other things. And it was very critical. The core value, the perceived value of what we did was heavily influenced by protecting what we had come up with.

Bobby. B
08:41 - 08:59
But again, the rules have changed, the games have changed, and I think there's a high level of vulnerability to trying to do that well these days. So right now, I'm just trying to learn about what's possible and not. So it's a growth path for me.

Greg
08:59 - 09:17
So if you were to go back to your current position, let's say that you were still doing that, knowing what you know now that 12 years have passed, is there something that you think that maybe has been missed or something based upon what you know now? Hindsight is everything, right? Is there anything you could take away from that?

Bobby. B
09:17 - 09:42
So we definitely exercised due diligence in the high-tech innovation that we were doing. It was first to market, but it was also first to protection. There were definitely cases where we had something that someone else had caught wind of or seen and found the missing link of maturation before we did. And that's just the game.

Bobby. B
09:43 - 10:19
That's how it plays out. But again, with With that information being so readily available now, it's definitely a different playing field, and I can't say that I really know how to run with it well. I have two things with the trademark office that I'm pushing through, and I did all my due diligence searches to make sure no one else had these things. I think there's, as you're pointing out, Greg, you're asking, there's definitely a need to protect, but you have to have enough maturation in your concept, otherwise it'll get kicked back.

Bobby. B
10:19 - 10:31
One other example, we tried to develop a cartoon character. about 10 years ago, and you'll figure, okay, this is such a weird name. No one's ever thought of this one. We were completely wrong.

Bobby. B
10:31 - 10:39
A major company that has animated characters had patented close to 10,000 potential names.

Greg
10:39 - 10:51
Right, and AI, you know, kicking everyone's heels. Everyone has to be concerned about how that takes place. Shadows, how about you? When you think about future-proofing your creativity, your creative work, what comes to mind for you?

Shadows Pub
10:51 - 11:17
Pretty little, actually. I guess if I look at it from the standpoint of if I should get sick or have an accident or whatever and it's a temporary absence, do I keep things afloat enough to return or don't I? you know, if I've got products out there, do they need to be maintained or are they just going to be able to operate on their own? So those all become questions you have to kind of deal with as you, as you go.

Shadows Pub
11:17 - 11:34
And then, you know, we get down if I'm at an age where I have to think about the possibility that, yeah, I might not be around at all. And do I, I really want to position that what I'm doing so that it continues on with somebody else looking after it, like my niece. So, yeah that's all stuff to consider

Greg
11:34 - 11:39
right because if you were planning on handing it down then there'd be a continuity step for that some training and

Shadows Pub
11:40 - 11:44
yeah she'd have to have access to it first of all she'd probably have to be interested in it

Greg
11:45 - 11:46
that would that usually helps right

Jennifer N
11:46 - 11:46
yeah

Greg
11:46 - 11:47
how about you jennifer

Jennifer N
11:47 - 11:59
This question is one that actually kind of has been oddly floating around in my own head. So good topic. So I approach it three different ways. Personal, I continue to follow my own curiosity that has served me well my entire life.

Jennifer N
11:59 - 12:14
And so that's how I keep my creative juices flowing. As far as the business goes, my sons are now part of my business. And so it's not my business, really, it's our business. and they are in every aspect of it, so they should be able to continue it if they so choose.

Jennifer N
12:15 - 12:37
And then as far as community goes, Alessandra, I'm in the same boat as you are in reference to trying to figure out how to make ensure that the, in my case, Napa Tama, that that community continues on beyond me, because I sure hope it would. Then the last piece is legacy. I have an example of where this is one of the reasons why it's at the forefront. Todd Cochran, the founder of Blueberry, passed away recently.

Jennifer N
12:37 - 13:10
That was a shock and a jolt for all of us because he was just going about his day and all of a sudden he wasn't going about his day. His sons, two sons, he has four or five kids and two of his sons have stepped in to take over his solo podcast. I can't tell you how beautiful and wonderful and lovely it is to be able to listen to his show, even without him, that his two sons are alternating each week being the host of the show. I can hear his voice in them.

Jennifer N
13:10 - 13:30
I hear the mannerisms of him in them. And I don't know I'm such a right now my eyes are getting all teary, because I think it's a lovely thing. If somebody will step into it and that in essence his legacy continues on past him as much as we all miss him. He is not gone, he is not forgotten,

Greg
13:30 - 13:30
you know,

Jennifer N
13:30 - 13:51
the other piece of that is that he had 1800 and something shows that he had done been doing week after week after week his son's. want to get him to at least 2000 and if they like it they'll continue which I hope they do, because that would be the best thing ever. So I think there's those aspects of that of where we all would like us as shadow said if her niece is interested. We would all like for our body of work to continue the reality is it may not.

Jennifer N
13:51 - 14:15
So what have we created that can have long-term visibility. And I think of the beautiful thing about Hive is that it's blockchain and isn't dependent on anything else except itself. So I think that's some of the legacy that we can leave behind, even if no one else within our world wants to continue what we're doing, it still exists to be discovered over and over and over again, because in that way, it's evergreen. And because it's evergreen, it continues beyond us.

Greg
14:15 - 14:25
Thank you, Jonathan. Yeah, what I get from that is ownership and investment, right? If you're invested in being part of the organization, you take ownership of certain things. Alessandra, good conversation.

Alessandra
14:25 - 15:09
It is a really good conversation i think i just had an epiphany while jennifer was talking about the three ways that she was that she was looking at future proofing one's creative work like i think i have been in regards to as a founder of creative work hour and all the sessions that we do more than a hundred a month but What's more important than the number of sessions that we've done or that we continue to do is that it be sustainable. We need an insurance policy of how can this continue to be here for all of us and for people who haven't found us yet? how can we continue to be here?

Alessandra
15:09 - 15:42
Maybe, and this is what was prompted by what Jennifer said, I should stop thinking of this as a, this is what I do every day, this is what has to take place every day before I get to do anything else. Just by it being engineered that way means I don't have the freedom that I need to pursue the things I need to pursue. It's like you can't leave the house. Now, what if in how we run this community, what if I had to take a break?

Alessandra
15:42 - 15:57
Not like a day a week, like what if I had to take a month off? If there's traveling or something like, how do you do that? How do you future-proof a community that comes together? So I'm like, oh, what if there's a break?

Alessandra
15:57 - 16:24
Because as some of you know that have been listening to our podcast, I've sustained a really serious injury. And I was thinking before I could handle my own healing, I was like, I got to get on creative work hour. So I was like, how do we do this? How can we write an insurance policy for creative work, whatever that is, that ensures that when you need a big break, that you can take it?

Alessandra
16:25 - 16:52
How do we write that? And in doing so, that's future-proofing. And I think we'll come back to this future-proofing topic again and again for the podcast, because future-proofing is also, there's preventative work that you do, just like with the body to prevent injuries. Yeah, so I think we haven't really solved anything with looking at this topic.

Alessandra
16:52 - 16:59
What we've done is we've stirred the pot and like, yeah, future-proofing, that's a problem to solve.

Greg
16:59 - 17:14
Sounds like a great project to work on as a group and even do a blog series to accompany it and a podcast series. And in the true spirit of building in public, building public and taking on as a project together, that might be an interesting thing to do. I don't know.

Alessandra
17:15 - 17:23
Yeah. Yeah, well, we'll have to give time to that, but I have to say, it is time to check time. Greg, what time is it?

Greg
17:24 - 17:44
It's that time again. You've wasted some perfectly good time listening to the Creative Workout Podcast when you could have been doing something else, but no. Today's co-hosts on the team were myself, Greg, Alessandra, Bobby W., Bobby B., Jennifer Navarrate, and Shadows Pub. What about you?

Greg
17:44 - 17:55
Let us know. How do you future-proof your creative work? Or what does that look like to you? Visit us on creativeworkhour.com and come back again next week for another lively discussion.