Josh Olenslager

Kendell Kelton (00:01):

Hi, I'm Kendell Kelton and I'm your host today on The Rough Draft. Featuring honest conversations with folks from across the creative industry, The Rough Draft explores the creative process, tools and resources used by some of the best in the business. From journalists to content creators and business leaders, we shed light on what it looks like to break into the industry, make mistakes, collaborate with others, and the essential tools that help us all along the way. I'm really excited about this week's guest, Josh Olenslager. As the director of publishing operations at LinkedIn Learning, Josh helps distribute video courses to professionals all over the globe to help them learn new skills at their own pace. With an MFA in poetry and a career that blends creativity with tech, he's written a book of poetry and is currently working on a second musical. We had an inspiring chat about how creativity and professional worlds intersect, and I can't wait to share it with you. Hi, Josh.

Josh Olenslager (01:02):

Hi, Kendell.

Kendell Kelton (01:03):

Hi. Thank you for coming on the show. You work for a company that I would assume almost every professional out there, at least in the US, knows and probably uses weekly, if not daily. LinkedIn. So I want to start things off by talking to you about what you actually do at LinkedIn.

Josh Olenslager (01:27):

Sure. I work in one of our businesses called LinkedIn Learning. And one of our missions at LinkedIn Learning is to help professionals become more successful with their careers. So as part of that we provide educational training in technology, business, and creative topic areas so that people can re-skill. And in this age of AI, where everything is changing, re-skilling is very important. So we take a lot of pride in the work that we do and the content that we publish to help people become more successful in their careers.

Kendell Kelton (02:00):

I want to dig into that, but first, how did you find yourself at LinkedIn?

Josh Olenslager (02:04):

I found myself at LinkedIn through various different acquisitions. I was in grad school in Wyoming working for a stock footage company at the age of the internet, the digital video internet. At the same time YouTube, as an example, was being built as a platform. I worked for a stock footage company, where we had contracts with various producers and content owners such as NBC News, National Geographic, the NCAA, all their sports libraries. And they had warehouses, warehouses, warehouses full of VHS tapes and other analog media from decades of production, and they were trying desperately to figure out how they could get this content digitized, into the cloud. I worked for a company where we were building private clouds, essentially, for these content owners. And then we had figured out a system for digitizing all of the things that they had on VHS tapes and DigiBetas and DVDs.

Kendell Kelton (03:04):

Yeah.

Josh Olenslager (03:05):

And then we were cutting that up and remarketing part of that as stock footage. So that's how I got my technical start. And then I found a little company in southern California called Lynda.com. It was an educational training company, an e-learning company. And they were trying to grow in online video distribution and online video delivery. And so I was able to find a position there that worked well and come in and help this small business build into this enterprise powerhouse that LinkedIn eventually purchased in 2015.

Kendell Kelton (03:34):

So LinkedIn Learning, how have y'all adopted to that pace, especially given the workforce and how much information they're having to absorb and how fast you're expected to train?

Josh Olenslager (03:48):

Yeah. Yeah. I think it's a delicate balance between, one of our brand values is to create really high quality content compared with a Joe Schmo with a camera that's rambling on for a long time. And it's really hard to extract the value out of that content from a learning perspective.

(04:08):

And so part of our value prop at LinkedIn and LinkedIn Learning is we create and curate the highest value content. It's simpler on the discovery side so people can consume it more easily. I think initially, the first thing we had to tackle when I was at Lynda.com is really about, how do we scale that quality of content production in a way that we can maintain that value proposition of having high quality, easily accessible learning while we're continuing to grow that? So that we can build our coverage. So that we can have more people access more quality materials that are going to help them in their career journeys.

(04:45):

And so over the course of the many years that I've worked there and through LinkedIn and everything, we've had to continually figure out, how do we scale this quality component at the same time that we need the content to come out faster? It's literally like every week something will change within the training, and keeping on top of that is a very complex thing that we have to manage. As a result, that ended up having us try to figure out, how do we be more agile than our production methodologies? And how do we be more pointed and intelligent about our curation so we understand, what do we need to update more urgently in order for people to be able to learn, to access that learning, and to stay on top of those things that they need to be successful?

Kendell Kelton (05:29):

I want to talk about, are there any trends that you're seeing in the type of content or learning that people all over the world are trying to consume at the same time? Is it productivity in the workplace? Is it just trying to find a job? Are there certain topics that seem to be very prevalent right now?

Josh Olenslager (05:46):

LinkedIn is very focused on professionals in the workplace, and so we try to figure out, how do we engage people who aren't like you would think of as a traditional professional? How do we engage people that are in the service marketplace, as an example, so that they can find productivity content and maybe grow into a managerial role or something like that? And then we have the opposite side of the spectrum which is, like, "Hey, I've got a CEO who needs to figure out, I don't know how to prepare for a meeting with an unexpected new client or how to think about business as a narrative," as an example. The trends that we're really seeing right now is a high consumption on, what is AI? What is AI content? How is that AI going to impact my business? Or how do I need to think about implementing that AI so it can impact my business? Right?

Kendell Kelton (06:37):

Yeah. It's really interesting because I've heard a few people talking about this recently, it's not that the fear of AI is necessarily gone but it does seem like we're in more of the adoption and, like, "Okay, it's not going to go away. How do we make it work?" And it's kind of like history repeating itself in certain cycles. There was the internet at one point, where everyone was like, "Whoa, what is this?" And then it became a helpful tool and you adopted with it. And so I think we're at that stage. So are there things that your team in particular are doing with AI to help nudge where your audience needs to go at this stage?

Josh Olenslager (07:18):

Speaking on my behalf, not on LinkedIn's behalf, but the environment is incredibly wide open. And I think if you can look at the investments across all of these different tech industries and the way people are thinking about, how does AI... trying to wrestle with that question, how is AI going to impact me personally and also the business that I work for? And how do I prepare for that?

(07:40):

I think over time, just like we saw with everything else, we started in this wild west environment. And so I think over time that's when we start to see the standardization. Obviously governments will start to regulate some of the things AI is able to do. We need to think about trust a lot in the AI world. And how do we make sure that we're building systems that people can trust? That they can understand, they can trust, and they can provide value. So we're in this nebulous territory of being able to try to work through all of these complex questions. Whether they're ethical, whether they're legal, or whether they're just like value propositions. And are they going to be productive?

Kendell Kelton (08:21):

I'd love to actually talk about your team for a second. Your current role involves leading and shaping large teams, so how do you keep things creative and exciting amongst the chaos of the market?

Josh Olenslager (08:37):

Sure. I don't think I actually said this earlier, but I lead all of the publication for LinkedIn Learning. So all of the courses that end up on LinkedIn Learning, my team handles those. And we do the packaging preparation so that we can distribute those. As part of that, it's a very technical function rather than a creative function in that way. But we work for a creative house. We work for a house where we have video directors and we have graphics artists, and we have other people that are applying their creative energies in order to build this great product that we can distribute.

(09:12):

The things that I'm doing to encourage my team on that creative front is actually leaning into the human side of it. Leaning into the community around it so that we don't get caught up in this environment of, the AI is going to take over some of the transactional pieces of my role, which allows me just to put my feet up on the desk. Actually, what that allows me to do is engage more fully with the creative community around me.

Kendell Kelton (09:37):

Yeah.

Josh Olenslager (09:37):

And being able to engage in that creative community at a deeper level can generate new brainstorming, new ideas, new creative energies, and kind of get back to the synergistic ideal that often we think about when we're saying, "As a poet, I want to be part of a writing group," even though some of the other folks in the writing group, we're at different levels and we have different ideas.

Kendell Kelton (10:04):

Well, I actually think that's a great transition for us. A lot of people juggle a corporate job with a personal endeavor, a creative endeavor. And so I'd like to talk a bit more about that, because you have a creative side hustle. So how do you balance the two? And what advice would you give somebody who may have an itch to try something out outside of their corporate job but just hasn't found a way to do so?

Josh Olenslager (10:35):

Sure. That's a really tricky... yeah, yeah, yeah-

Kendell Kelton (10:39):

A loaded question. A loaded question.

Josh Olenslager (10:40):

A really tricky question. I can talk a little bit about what I've done over the years and some of the things that have worked and some of the things that haven't worked. Ultimately, where I'm at today is about discipline and being very regimented with my schedule.

Kendell Kelton (10:58):

Yeah.

Josh Olenslager (10:59):

It's the least exciting thing, from a creative perspective, to try to say, "I have a block of time and I'm going to try to force my creativity into that time." But I think what I've done is I've changed my expectation about what I expect to get out of that block of time. Right?

Kendell Kelton (11:17):

Yeah.

Josh Olenslager (11:17):

So my time horizons have expanded, in a way. So if I have a Saturday afternoon and I'm like, "Okay, I've got three hours on Saturday where I can sit down and work on my creative side hustle," I actually don't expect that, at the end of that three hours, I'll have made significant progress. What I will have expected is, at the end of that three hours, I've made some progress, whether that's sparking new ideas, whether that's figuring out a word that's been stopping me, or figuring out just one small moment to move forward and then trusting myself. One of those three hour blocks, or one of those blocks that I've set aside, I'll have a burst. If you're an exerciser you know about high intensity interval training, where you burst and then you rest and then you burst and then you rest.

Kendell Kelton (12:12):

Right.

Josh Olenslager (12:14):

But the thing is, when you're resting you're still working. And I think if you think about creativity or a side hustle, or the way that I've been thinking about it is really borrowing some of these concepts to say, "If I sit down for a bit, I don't expect to have a finished product at the end of that bit but what I expect is to have practiced and, through that practice, over time I'll end up becoming stronger when those bursts happen."

Kendell Kelton (12:38):

That is a great analogy. I find that such a great and helpful way to think about it. And my mind went to, and I don't know if you would say it has or not, but has that mindset influenced how you approach projects in the corporate world?

Josh Olenslager (12:56):

Yeah. It's a very similar... when I described the time horizon that I'm giving myself for a completion, I think at the foundational level there's no difference between a professional project and a creative project in the sense that there has to be a schedule and there has to be a roadmap or a goal at the end of it, and milestones that you reach along the way.

Kendell Kelton (13:22):

Yeah.

Josh Olenslager (13:22):

And so understanding where you're at, whether that's in your career or your creative journey, and being able to say, "What is the goal for this project that I have?" Some of my projects, as an example, are simply practice projects. I'm like, "My goal for this project is to practice. I need to write sentences, and I haven't done that well, so I'm just going to practice writing sentences." Those sentences could be good or bad. That's irrelevant.

(13:46):

But looking at the time horizon for what you have for your work or for your creative and saying, "Do I have a deadline looming? Do I have something else where I need to either increase the amount of time I'm spending in order to meet that deadline or extend that deadline out in order to give myself the practical space I need to accomplish all the goals or meet all the milestones along the way to achieving that project outcome?" So in a lot of ways it isn't the creative way, just to say, "I'm the genius artist that sits down and writes something out on the first draft." Yeah, exactly.

Kendell Kelton (14:24):

Splashing paint on the wall and-

Josh Olenslager (14:26):

Yeah. I'm not Jackson Pollock, right?

Kendell Kelton (14:28):

Yeah.

Josh Olenslager (14:29):

I might have a wild mind like that, but I'm not Jackson Pollock, where I can sit down in an afternoon, smoke half a pack of cigarettes, and then might come out of it with a nice painting. That's not the way that I can produce.

Kendell Kelton (14:40):

Yeah.

Josh Olenslager (14:42):

And I think being aware of that and being accepting of that as a professional or as a creative, that's going to help you go a long way.

Kendell Kelton (14:51):

We've talked to a lot of guests about their creative process, like you just very beautifully articulated to us your own. But we've also talked about the evolution of tools. And so are there any tools that you have adopted recently that you think are very powerful? Are there things that you're just like, "No, I'm going to stick to the bread and butter?"

Josh Olenslager (15:20):

Yeah. I think at the foundational level I'm still the bread and butter kind of guy. I still write in my journal every day. Most of that writing is terrible, but what it does is it allows me to have that consistency over time, where every day I spend some amount of time putting pen to paper, literally, and something comes out. And I'm not concerned about the quality of what's coming out, but I'm concerned about the behavior that I'm building.

(15:47):

And I think over time you find those tools, whether that's pen and paper, whether that's typing up a text note on your computer, or whatever. You find those things where you feel comfortable and confident, and it's natural for you to practice in those environments and build those habits and routines. I do think some of the new tools are exciting, just from a curiosity perspective. I think one of the things about being creative is trying to figure out, how do I continue to be curious and engage with the world? Because it's so easy to get siloed, especially over the last few years. There was a forced siloing, in a lot of ways. And how do you reopen up that world or how do you keep that world open? I think ChatGPT, as an example, is a really fun tool where you can hold conversations. I try to stump it.

Kendell Kelton (16:41):

Have you had any luck?

Josh Olenslager (16:42):

I know there's a lot of hallucinations and...

Kendell Kelton (16:45):

Yeah.

Josh Olenslager (16:45):

Yeah. Actually I've had a few where it's like... I asked it the other day about whether a cruise ship qualified under the definition of an ark, because they're both really large ships, et cetera. And ChatGPT was very adamant that a cruise ship couldn't qualify as an ark. And it had a lot of biblical attribution and references to saying, "Yes, you could fit a bunch of animals on it but it's not so many cubits, and it's not made out of wood," and stuff like this. So using these tools to explore, for me, some of the absurdities of the world and ask in a lot of ways really obscure or obtuse or ridiculous questions, and then see where that goes. Where that path takes it.

(17:33):

And it in some ways can replicate a little bit of that brainstorming feedback that you would get out of a working group or something like that. But it's really figuring out, on that front, how do you engage with those types of tools, whether that's ChatGPT or other types of tools, in a way that's going to drive that curiosity and help split it open so that you can get in there and have a little fun with it?

Kendell Kelton (18:01):

Well, now that we've covered a bit of your creative process, I want to hear more about your personal projects. You are working on a musical and a poetry collection. I would love for you to tell us more about those projects.

Josh Olenslager (18:17):

Yeah, sure. Every year I try to give myself something to work on, just to be able to, as I talked about earlier during the process stage, block out those bits of time and have a project with a goal and some milestones to meet. This year I decided I was going to work on my second musical. The first musical I wrote like 20 years ago, nearly. And so the second musical, it's been an idea that's been rattling around in the back of my head for five or six years. And of course the second I sit down to write it it changes completely, which is I think a pretty common refrain, probably, for people with creative side hustles. But what I ended up doing was breaking it down into the milestones of, what am I really trying to accomplish? What is my goal? What am I trying to meet?

(19:08):

And a lot of it was, I just want to pick back up and play piano again. As part of that, playing piano, writing a musical gave me a format in order for me to think creatively about musical composition.

Kendell Kelton (19:22):

Yeah.

Josh Olenslager (19:23):

And it gave me a framework for being able to write music with a goal in mind. So it gave me a direction, which I think was very important. And I've had a lot of fun doing it, so that's good. And then poetry, I'm always tinkering with poetry. And it's really interesting, over the years, how poetry changes format. Its subject matter and its composition, and its... all the technical pieces about it, for me, are constantly evolving.

Kendell Kelton (19:51):

Poetry is so interesting. Writing it, it's kind of bringing your inner monologue to life. And it can be such a unique and also deeply personal form of writing. How does it challenge you as a writer?

Josh Olenslager (20:10):

Yeah. I think a lot of it is, for me, poetry helps me understand my world. In a lot of ways the world is very large and expansive, and it can be... people talk a lot about, I can see the see the tree but I can't really see the forest and the tree at the same time. And I think even though that's a worn adage and a worn metaphor, it's still true. And I think poetry, for me, helps me give me that perspective, where I really want to see the forest.

Kendell Kelton (20:42):

Yeah.

Josh Olenslager (20:43):

And so poetry gives me that chance to zoom out and look at a world that's very abstract, in a lot of ways, and say, "Wow, this is a varied landscape with a lot of different pieces involved." And I want to understand that better. And so then I can zoom in on the details within the poetry.

Kendell Kelton (20:58):

And how has, and it may or may not, but how has the poetry side of your creative mind influenced the musical side? Or maybe it's vice versa?

Josh Olenslager (21:08):

I think they're related. In poetry, as an example, I think a lot about sound and I think a lot about texture, more so than language even. So word choice for me, and even construction and punctuation, a lot of that for me is about texture and it's about the sound of things. So some of the poems that I've written in the past can be very abstract or nonsensical, and they're less narrative-driven, I would say, and more emotionally or using sensation as a driving force.

(21:42):

And I think for me on the musical side, actually it's way more narrative, because you have to have an arc and a regular storyline, and you have to have character development and other types of things. But I still start from that, what is the texture and the quality of emotion that I want this particular piece of music or this moment in this story to represent? And how do I evolve that sensation over the course of that project? How does that arc end up encompassing both that grandeur and that intimacy?

Kendell Kelton (22:15):

And would you be willing to share a bit about the musical itself?

Josh Olenslager (22:18):

There is an aging performer, an aging celebrity. And during the course of her career twilight she's feeling that age. She's coming in and saying, "I'm being displaced by younger people. The audience that I used to have and the attention I used to get from them and the accolades that I used to receive, those are no longer consistent." And so that absence is a real thing for this character, to be able to say, "I'm aging. I'm getting older." Obviously I'm in my midlife, so I have midlife crises and other types of things that I'm dealing with. So it's a good feeder material.

Kendell Kelton (22:51):

I was about to say. This is a very human thing for so many people.

Josh Olenslager (22:55):

Yeah, exactly. We all go through these stages, right?

Kendell Kelton (22:57):

Yeah.

Josh Olenslager (22:57):

And the stage that I'm in, this is driving this narrative. So the hero is this woman who's sort of in this crisis of change as she approaches middle age and is moving towards the back half of her career, and all this other stuff. And so all of that is, as you mentioned, a very human thing that all of us go through. All of us go through these transitions. All of us have the need at some point in our lives to stand up for ourselves and say, "This is who I am and this is who I am now, and it's changed." It may be different. And to be able to re-carve out that moment of truth for themselves so that they can find that balance and, hopefully for all of us, that moment of respite and joy so that we can continue to look forward to living rather than running and being afraid of what we no longer have.

Kendell Kelton (23:53):

And that's, I would say, not just what you're creating on a personal front but even professionally, too. Right?

Josh Olenslager (23:59):

Yeah, for sure.

Kendell Kelton (24:00):

There is a lot of synergies, I think, in what you were saying about adapting to not just getting older but just becoming... the further and further you get in your life or your career, and being able to adapt and stay confident and secure in your own right, and being able to speak up to yourself. There just seems to be a lot of synergies in what you're building creatively and then what you are actually trying to achieve with LinkedIn Learning, it feels like from the outside.

Josh Olenslager (24:32):

Yeah, for sure. I think that's one of the realities of the world, is as we live and grow and learn and we get more experiences, life seems to become more complex. And for me at least, the sooner I embrace this idea of pursuing simplicity, it doesn't mean that it is simple. It just means pursuing simplicity. It's really helped me say, "The simplicity helps me clarify my direction and clarify my goals, helps me overcome confusion that I may get lost in, and it helps me build my own self-confidence because I'm clear on what I'm doing." And I think that clarity can really open up the opportunity to pursue in a very passionate way this idea of curiosity and opening and exploring the world.

Kendell Kelton (25:27):

How do you see yourself creatively or professionally evolving?

Josh Olenslager (25:30):

Yeah. I think I've had so many projects that I've started and abandoned over the years. Realistically, the goal I'm stepping toward, both creatively and professionally, is being able to satisfy that itch for creativity in a more regular way or a more patterned way so that it becomes more embedded in my life. As I continue to evolve, instead of starting a project and abandoning it, that's really where my current thing that we talked about earlier of being disciplined and making sure that I'm regimented about my practice... even if progress is small, that becomes so critical for me being able to achieve that goal that's maybe a few years out. My goal isn't, what do I get done this Tuesday? My goal is, what do I get done this Tuesday that helps me be the person I want to be five years from Tuesday? And so I think that's really where my mindset is at.

Kendell Kelton (26:35):

That was a beautiful way to wrap up this episode. I thank you so much for joining us. Before we go, can you let our audience know where they could connect with you?

Josh Olenslager (26:48):

You can always find me on LinkedIn. That's the easiest place to find me.

Kendell Kelton (26:52):

Well, thank you again.

Josh Olenslager (26:53):

Yeah. Thank you for the opportunity, Kendell. I really enjoyed it.

Kendell Kelton (26:56):

Well, that's it for today's episode of The Rough Draft. To learn more about our guest and to find links and resources related to the conversation, check out rev.com/podcast. If you enjoyed today's conversation, be sure to rate and subscribe in order to stay up to date with the latest episodes. Thank you for listening, and we look forward to seeing you again on the next episode of The Rough Draft.