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171: Stop Waiting for Permission—Start Leading with Joy: James Gilchrist on Finding Work That Fits You

In this episode of EdUp L&D, Holly Owens interviews James Gilchrist, an influential figure in the Learning and Development (L&D) space. James shares his unique journey from theater to L&D, emphasizing the importance of storytelling, overcoming imposter syndrome, and the transformative role of AI in creating engaging learning experiences. He offers valuable insights for those transitioning into L&D, highlighting the significance of networking and focusing on what brings joy in one's career. The conversation concludes with thoughts on the future of L&D and the importance of creating connections in the professional landscape.

In this episode of EdUp L&D, Holly Owens interviews James Gilchrist, an influential figure in the Learning and Development (L&D) space. James shares his unique journey from theater to L&D, emphasizing the importance of storytelling, overcoming imposter syndrome, and the transformative role of AI in creating engaging learning experiences. He offers valuable insights for those transitioning into L&D, highlighting the significance of networking and focusing on what brings joy in one's career. The conversation concludes with thoughts on the future of L&D and the importance of creating connections in the professional landscape.

 

Resources mentioned in this episode:

 

Guest Contact Information:

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Episode Sponsor: iSpring Solutions

 

🎙️ Huge thanks to our friends at iSpring Solutions for sponsoring this episode of the EdUp L&D podcast! 🙌

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Thanks for tuning in! 🎧

 

Holly Owens (00:00.802)
Hello everyone and welcome to another fantastic episode of Add Up L &D. I am feeling very excited today to have this guest on this show. James Gilchrist is here and he is gonna talk about all things L &D. He's an influencer, he works with Icepring, he has his own consulting business. He's an all around, just knows a lot of different things and I'm expecting and as you should, a lot of great advice here. So James, welcome to the show.

James Gilchrist (00:30.277)
Thank you, Holly, and no pressure.

Holly Owens (00:33.454)
No pressure, you'll be fine. You'll be fine. So why don't we start out with you telling us your story about how you started and where you're at now, like your path to how you came here. You have your own business, you do a lot of different things. So tell us about your journey.

James Gilchrist (00:50.843)
Well, it's lovely to meet your listeners. And I just want to say, you and I have been talking about doing this show for a while. And there were a few times when, and when it didn't happen. No, no, it's a, it's life. And, but life is allowing us to be here together today. And I just want to say how excited I am to be in the room with you because, I'm a, I'm a huge fan and, I love working with you and we have worked together sort of.

Holly Owens (00:58.983)
I know, it's my fault.

James Gilchrist (01:19.813)
in tandem in a lot of ways, but we haven't had the chance to do this. We've never done a panel. We've never had the face-to-face online. So I'm honored that you've got me on your show. So thanks for that.

Holly Owens (01:28.022)
Yeah. Ditto. I'm honored that you got to be here and that we got to meet in person in Las Vegas last year. Devilern!

James Gilchrist (01:36.725)
Yes. Yes. Yes. Devlearn last year. I think that was the first time we ever got to be in the, in the same breathing, the same air. Yeah. okay. Well, thanks. so first I just want to say, I was hosting a networking event, a few weeks ago and I was inspired to tell the folks in the room.

Holly Owens (01:44.206)
in the actual, yes, for sure, for sure. Well, tell us your story, James. I'm excited to listen to it.

James Gilchrist (02:03.502)
that when they went into their breakout sessions and they began talking to each other for the purposes of getting to know each other and hopefully forging some connections and finding waves forward, ways of working, collaborating, et cetera, that they should be mindful of their past and their story, like you've just asked me to share my story, but more focused on their future. Where are they going? How do they feel about where they are now in

relationship to where they see themselves and take people on that journey where what the future looks like. What is it? You know, what do you have in store for yourself? Because it's that story and that journey that invites others to come on it with you. You can't do anything about anything that's happened before. And none of us really want to repeat what we've done before. We're all looking for the next big thing and discovering what makes us happy and figuring out

Holly Owens (02:56.75)
Absolutely.

James Gilchrist (03:02.884)
you know, how we can get more passionate about the thing that happens today and tomorrow and the day after that. So, so I will, but I, but I understand that context and knowing in some cases, just how you got into the field of L and D can be really interesting to people who may be on at that point in their career themselves. So I will tell a little bit of that story. I think it's.

Good for folks to know that I spent my entire 20s. got an undergraduate degree in music and print journalism, and I immediately started working for a theater company. was touring colleges and universities, doing theater intended to inform and help students get acclimated to the new bigger world of being on their own and living out, you know, often very far from home.

Holly Owens (03:56.12)
Yeah.

James Gilchrist (03:58.261)
and writing music and finding musicians and starting bands and doing all of that. so no, I didn't, I didn't graduate from my university and immediately try to find a job working at some company that needed learning solutions. That was not, that was not my path. No, not at all. And apart from, you know, this strong feeling that I needed to hang on to something that

Holly Owens (04:15.874)
That was not the trajectory. Yeah, yeah.

James Gilchrist (04:24.826)
to someone else would look viable on a resume, like an English degree or my journalism degree. I have always been someone who was looking, looking to the stars as it were, and not, and trying not to get myself too worried about, well, to use my mom's words, how to make a living, you know? That being said, that trajectory took me to...

Holly Owens (04:45.793)
Yeah.

James Gilchrist (04:52.192)
Fast forward 10 years and I'm living in New York City and I am auditioning for things. I've been cast in number of Shakespeare productions because I tacked on a two year certification at a place called the National Shakespeare Conservatory in my late 20s. And I was lucky enough to get some great work and some great parts and that sort of thing. But it's New York City. And if you don't want to live with 10 people in a shoe box,

Holly Owens (05:09.473)
no.

James Gilchrist (05:20.656)
You need a little bit of money coming in. so, uh, it was network time. Uh, I called a friend. I phoned a friend. Can I phone a friend? I phoned a friend who said he had just, um, seen an opportunity to work, uh, basic, how he described it was answering phones at a payroll company. And I was like, well, that sounds straightforward, not very exciting, but you know, I figured it would be flexible and.

Holly Owens (05:23.363)
Yes.

Holly Owens (05:29.457)
Yeah.

Holly Owens (05:43.772)
wow.

Holly Owens (05:49.87)
Pay the bills.

James Gilchrist (05:50.883)
it would pay the bills. So what happened next? Well, they hire me, which in my mind was kind of amazing because what they were hoping was that they would be bringing people who had some business acumen and understood payroll taxes and you know, maybe a little bit of accounting and all and I had none of that. But I but but I got hired and I went through their what I thought of is their two week boot camp. So I'm

Holly Owens (06:11.308)
Right.

James Gilchrist (06:19.364)
being trained by someone on the job whose job is not to train new hires, but is to be a manager in their own area and they have their own team and they are there doing the best that they can to give people what they think they need to know to succeed in the job. That's a nice way of putting it, but it was disjointed. was distracting. were questions that got left unanswered. The training materials were definitely more missed than hit.

Holly Owens (06:37.432)
Yeah.

Holly Owens (06:43.476)
as most onboarding is.

James Gilchrist (06:49.62)
but when, you know, but I've always been a good student. So I applied myself and I felt, okay, if what they've told me is what I need to know, I am reasonably prepared to do this. I couldn't have been more wrong. I got through it is all I can say. I got through my last, you know, the first four months of my time at this company were during the busiest time of year for them, which was the end of the year, because lots more things happen in payroll and business and stuff like that. So.

Holly Owens (07:13.143)
my.

James Gilchrist (07:19.21)
There I am struggling. I'm going into my own manager's office like six times a day. You know, I was the guy who would assure the customer that I would get back to them and let them know the answer to their question because I couldn't give it to them in the moment. And then I would just run off with my notebook and be like, okay, what did this mean? And what happened and how badly did I mess this up and et cetera? All of which brought me all of that finds me at a time a few weeks into the job.

where I'm sitting in the break room and I see they've actually posted something on the cork board saying, they're looking for a training manager. And I thought they're looking for a training manager. I'm glad they're looking for a training manager. It would have been great if they already had a training manager, but, here's an opportunity. and I am fresh from out of the fire. So I made an appointment, walked into the one person HR department sat down.

Holly Owens (08:04.319)
Right?

Holly Owens (08:17.675)
my gosh.

James Gilchrist (08:18.156)
Introduced myself and explained that I was really interested in this posting and I was hoping that they would consider me for it and that I had these ideas and that this and that and the other I you know all of this and the woman sitting across from me name is Patricia amazing person. We got to be great friends in the future She's sitting there in her inimitable way hands folded smiling. She just she's just letting me run down You know everything I have to say and at the end she says James well, I

Holly Owens (08:41.965)
Yeah.

James Gilchrist (08:46.36)
really appreciate you coming in to talk to me about this. We'd kind of like to see how you do at the job we just hired you for before we promote you into this, into this position. But, and I give her credit for this. said, if the efficient, if the position is still open, after the end of the year, come back and see me. And I remembered that and I thanked her and I went back and I lived out my life as a

Holly Owens (08:55.783)
Yeah.

James Gilchrist (09:16.132)
you know, payroll accountant and came back to her office. And at that point, explained how much I'd learned and that I was still very interested in it. And she gave me the job. So that was, that was the, that was the beginning. That was the beginning of my next 23 years doing things related to training people and creating learning solutions and

Holly Owens (09:19.853)
Yeah.

Holly Owens (09:29.954)
Wow, yes, I knew that was gonna happen. I knew that was gonna happen. Yeah.

James Gilchrist (09:43.461)
figuring out what this whole L and D thing is, which at the time, of course, that was not on my radar at all. You know, I, all I knew was I had people in front of me who needed help and there was materials that I knew had been used before that I was expected to use going forward that I had used and they didn't work for me. So I didn't want to use, I didn't, I didn't want to just repeat, you know, wash, rinse, repeat exactly.

Holly Owens (09:49.89)
yeah.

Holly Owens (10:06.062)
That process, yeah, yeah, you're change it.

James Gilchrist (10:09.912)
So that's, so that's the very beginning. And I think the important thing to take away from that story is recognizing that it's, it was my experience that it wasn't my experience that allowed me to move the ball down the field, to be given an opportunity. All it took was me being passionate enough about the problem and having been being solution oriented that

Holly Owens (10:25.624)
Right.

James Gilchrist (10:36.47)
someone recognized that having me working for them on that project or in that capacity would make their life easier rather than harder.

Holly Owens (10:46.434)
Yeah, yeah, I love that. And that's what L &D is all about. That's what it's all about. I love it that you're a theater person. could see, I can tell just from your voice and stuff that that would be an expectation or an assumption of mine. Because your voice is just, the way you present yourself, you have so much confidence when you're presenting or when you're, you know, you're the person who's moderating stuff in the sessions. I just love that about you. I think you're one of the best people.

that I've ever seen like moderate some of those sessions and just be on a stage. It's really interesting because a lot of us and people in the audience too that are in the L and D space, we kind of fell into these roles. I took the more of the, I would say quote unquote, the traditional path. I was a high school teacher and then I transitioned into e-learning and then went into higher education instructional design. But I love the fact that your story is not the traditional path. Like you got a job because you're trying to make a

trying to make a living, you're trying to pay the bills, and then you kind of just put yourself out there. You're very proactive about, you know, going into the office and explaining why you'd be a great fit or the solutions that you could just from knowing what you were doing. I think that's so cool and to me, like that says a lot to our audience too. Like don't just wait for somebody to come give you the position. I think a lot of us are like, we're stuck maybe in the old archaic days, like,

After 10 years, I'm really gonna get that promotion from Bob and he's gonna see all the hard work I did and then it never comes.

James Gilchrist (12:21.56)
Yeah. Yeah. Well that I love that you mentioned that because, because it is one of the things that I learned by doing by putting myself into the business world and it just, you know, sink or swim, resulted in me picking up some ideas about how it all worked and what I needed to do to succeed and what didn't work, by virtue of experiencing it.

And I want to go back. First of all, thank you very much for what you said about me as a presenter and et cetera, facilitator. I just want to say for the folks listening, cause this is about them. Like this is a conversation we get to have, but in my mind, it's all about whoever decides to tune in and listen to this episode. What, you know, how are we making their day better? That kind of thing. I just want to say that the confidence that is perceived is.

Holly Owens (12:54.734)
You're great. Yeah.

Holly Owens (13:13.571)
Right.

James Gilchrist (13:21.604)
is part construct and part choosing where to put my attention. So if, for example, I were to tell you putting my attention on my audience didn't necessarily help me reach my audience. That might not be the first thing you would expect. mean, you kind of think, well, where you put your attention is where the energy goes and

Holly Owens (13:29.292)
Okay.

Holly Owens (13:43.021)
Right.

James Gilchrist (13:47.385)
And that's what we're, that's what we need to do, right? We've heard focus is important and putting yourself in the shoes of your, of your learner or your listener, or you're in your case, your audience, right? But one of the things that I learned as a performer, a musician playing on stage with a band, doing my own music, acting in plays, auditioning.

Holly Owens (13:51.287)
Right.

Holly Owens (14:10.082)
Yeah. That stuff scares me.

James Gilchrist (14:11.672)
which is a, which is, which is, it's a, that's a whole nother, like there's a wonderful, there's a wonderful story to tie the art of auditioning with succeeding in business, which maybe we can get into. But for now, I just want to say I learned early on that in those moments when I was on stage, that if I detected my focus or my attention moving away from what was happening in the moment, away from my other actors, away from

Holly Owens (14:15.789)
Yeah.

James Gilchrist (14:41.878)
What my thoughts needed to be related to what I was doing. I'm think I'm channeling Yoda here. I'm like never his mind on where he was, what he was doing. Right. Anytime my attention drifted, anytime I started to imagine seeing myself as others were seeing me, the wheels came off crash and burn. So one of the reasons why I get so excited about presenting and facilitating these days.

Holly Owens (14:49.612)
Right?

Yeah, love that.

James Gilchrist (15:10.85)
is because I spend time and I know I'm going to spend time beforehand asking myself the question, why am I doing this? What is it that I care about? What is the best possible outcome? And is this fun? And answering those questions for myself so that I can facilitate a networking event and be passionate and outgoing and hopefully engaging because I truly

care that everyone who's there is going to have a great experience. That's what I care about. So I just lean into that. Like, what do I care about? Why am I here? And pretty soon I'm not thinking about myself. I'm not thinking about how I'm doing. I'm not thinking about what I said two seconds ago. I'm just in the moment and I'm present and everyone, no matter what circumstance you're going into that may feel uncomfortable.

If you ask yourself those questions and you teach yourself to get in touch with that part of you, that is the why, you know, why you're doing it, why you're doing what you do. You will feel more confident. You will seem more confident and you will actually be better at what you're there to do. So that's, that's my, my hope that people sort of take away.

Holly Owens (16:26.35)
Absolutely. Oh my gosh.

I love that and that's what I think about with the podcast. That's what I think about every time I present. Like I want to be so on and prepped for the what I'm sharing with the audience that I want them to feel like, you know, when people say to me at the end of like a presentation or the end of like a conference, you know, interaction or something that they feel more confident and they feel ready to start again or they feel more motivated. That's exactly what I want to happen.

James Gilchrist (17:00.986)
Yeah.

Holly Owens (17:01.09)
That's exactly what I want. I want to give back. I'm just you're at this stage in your career where you're like, I just want to share what like you what I've learned and don't make the same mistakes as me. It's kind of like raising children like we don't want our kids to make the same mistakes that we made as we were growing up or, you know, learning different things. And I think what you're kind of alluding to here is an imposter syndrome that kind of flutters about throughout L and D. And I think people really struggle with that.

James Gilchrist (17:25.626)
Yes. Yes. Yes. And.

Yeah, absolutely. Imposter syndrome is running rampant and it's obviously not limited to our industry. It happens everywhere, but there's an aspect of what we do that involves putting yourself in view. You know, you can, you can have a job where no one ever sees you do what you do. can have it. Yeah, exactly. That's exactly what I was actually thinking of. was picturing.

Holly Owens (17:39.828)
No, yeah.

Holly Owens (17:51.722)
I.T. I call them hermits.

James Gilchrist (17:56.751)
I was like in this, I was in the server room, you know, in my mind, I was like looking at the keyboard sticking out of the wall anyway. But yeah, the point is it is true that there is an aspect of the, the things that get folded up into our larger world, whether it's talent development, human resources, learning and development, you know, creating the solutions, delivering the solutions, presenting the solutions, pitching the solutions. I mean, there's a lot of people. There's it's all, it's all people all the time.

Holly Owens (17:59.362)
Yeah?

James Gilchrist (18:24.048)
You know, when, and many people I speak to who are getting into instructional design, talk about how excited they are to learn the tools and create the stuff and tap into their inner creative artisanal what have you to produce. Right. And that is fun. And I spent 20 years loving that I could do that. Um, but as I came to lean into this chapter of my career slash life experience, I thought,

Holly Owens (18:36.354)
Yeah.

James Gilchrist (18:54.262)
about what mattered to me and where I felt the most at home. And despite being that guy for all those years that, well, we need this built like James, James is up on that. He's up on the latest tech. knew he's the guy who's teaching other people how to use this tool. just bought, you know, I was that guy, believe me. Exactly. But where I really shine and where I personally

Holly Owens (19:15.052)
Right? Like you're the expert. You're definitely

James Gilchrist (19:21.806)
get the most satisfaction and gratification is in the conversations with people that are about to decide what to do next. Those moments where decisions get made, those moments where a direction that you've been going in for a long time suddenly forks and you choose to go off in a new direction. And one of the wonderful things about how learning and development I see is transitioning as a result of the latest influx of technology.

is that we're being given tools that allow us to be more flexible in the moment. We can create the resource. And I just talked, I'm going to drop a name, Jen Kammerdiener. She's one of the lovely people that I have worked with directly as a client of Lighthouse L &D Consulting in the past few years. She has a company called ClearPath Learning Solutions. They're a great firm, a great L &D firm with great leadership. That said,

Holly Owens (20:00.237)
Yeah.

Holly Owens (20:08.195)
Yeah.

James Gilchrist (20:19.772)
one of the things that I posted about, I commented on a post of hers just today on LinkedIn was to say, once upon a time, the problem was that figuring out how to position all the resources needed for a team equidistant from the point of need, meaning it would be just as easy to get this resource when you needed it as it was to get that resource. Think of

The person or a business in the center of a circle and all the resources needed to make everything keep running smoothly in a circle around them, you know, equidistant in every direction. The problem was even if you could set up a system like that, you couldn't scale it because the knowledge that was required of the person or the business or the team in the middle of the circle at any given moment, depending on what was fluctuating in their business world. Wasn't that was the piece that was missing, meaning

Holly Owens (20:55.842)
Right.

James Gilchrist (21:19.492)
They know there's a problem. They know they need to react, but they didn't know what tool to use to react, how to react, when to react, unless they could find that person who had that knowledge strapped in their head, or it was in a learning module or et cetera. So you can't scale because there's always that moment where you sort of jam the gears, know, shift up. trying to, you're trying to upshift and you, yeah, you get this little bottleneck, right? So, but now with AI and the tools that we have.

Holly Owens (21:32.0)
Exactly.

Holly Owens (21:41.422)
You bottle next things. Yeah

James Gilchrist (21:49.541)
to make it possible for on the fly people to ask the question that they need answered and get the information that tells them exactly what resources to tap into. Now we're flying. Now that's, that's the advantage of this new world we find ourselves in. And it's what we've always wanted. We've always talked about creating learning paths that were flexible and customizable and specific to the learner and the need and that

Holly Owens (22:01.878)
I love it. Yes.

Holly Owens (22:15.086)
but it took so much work in the background. It took so much work to create that. Hours and hours and hours. Yeah.

James Gilchrist (22:17.998)
Yeah. Yeah. my God. Right. And, a week, a month, a year from now, so much has changed that all those mechanisms are like train tracks leading nowhere. Like, so all the work you did to build it in the first place, whoo, you're like, well, it's hard to convince the higher ups to throw that much money at the problem to do it all over again, because you see immediately, well, we're going to be in the same situation. So we have to.

Holly Owens (22:32.493)
Right?

Holly Owens (22:43.319)
Right.

James Gilchrist (22:47.012)
you know, we have to figure out a new way of doing this. now with the where we find ourselves now, and this is what gets me excited when I see people like you and David Kelly and Karen North and Tom McDowell. just read his newsletter this morning. All those people, right?

Holly Owens (23:01.703)
I love Tom. gosh, he's so great.

James Gilchrist (23:05.466)
They're dropping these truth bombs suggesting that, hey, rather than being afraid of what these tools like AI can do, get excited about how you can leverage those tools to do what we've always dreamed of, right? Don't be afraid of the tool. Be excited that now what we've always wanted to create and have told people would be the ideal solution, we actually get to do, yeah.

Holly Owens (23:19.702)
Right. Yeah.

Holly Owens (23:30.23)
It's here. I know it's fantastic. And the thing about it is, like the people that are resisting or creating the stigma around it that is truly unnecessary at 25 years into the 21st century. I, everything that, so I just recently, I use a tool called motion. I'm not getting any things from them. I honestly have been using it for about a year and they just incorporated some

AI, they call them AI employees. So they each do like different things. And one of mine is it responds to email messages, like it drafts it, it just writes a draft to the email that somebody sent me. And I'm like, this is a game changer for me because I spend as a director so much time curating the correct words or what to say or how to respond, you know, like being a perfectionist. And it's just saving me so much time. And I'm like,

James Gilchrist (24:20.068)
Yeah, yeah, yeah

Holly Owens (24:29.15)
One thing I really truly feel is that instructional designers or people in learning and development now get the space to actually be creative. Instead of worrying about the scripting, instead of worrying about the whole outline of the course and trying to figure that out in five to seven days or something like that, it's already done. So you really get to be in that design element, you really get to be in that development piece and be super creative. It's been what I've been...

hoping for and wanting for my entire career as an instructional designer is something to take off that pressure so that can sit in this space and just figure out new ways to kind of tap the psyche, the motivation, all that psychology stuff that goes into instructional design. Yeah, it's amazing. I don't know how people live without AI. How do we do it? It's like before the internet. Yeah.

James Gilchrist (25:15.396)
Yeah, yeah.

James Gilchrist (25:22.512)
Well, well, yeah, yeah. Well, so, so let, I'll add something to that because I agree with that. But again, thinking about, people, people who may, this is, this is the thing about change. The thing about change is it's always uncomfortable, right? The reason change is uncomfortable is because you are not yet lined up with what comes next. Right?

Holly Owens (25:41.272)
Yeah.

James Gilchrist (25:49.295)
Being shown a new way of working or a new circumstance or your, your team is being reorganized or you've got a new manager. Like all of those things feel uncomfortable because we put our focus on what is different, what we don't have anymore that we used to have, or that we knew. We put our focus there and we tell that story over and over again, you know, in the break room to our wives, to, know, we just, we just, we just commit about the fact that, they don't know what they're doing. They're,

Holly Owens (26:13.024)
Yeah

Right, the typewriter is gonna last forever. It's the main, yeah, insert.

James Gilchrist (26:17.818)
They're upsetting the Apple carton.

James Gilchrist (26:22.926)
Yeah, whatever, whatever it is, just recognize that the change that what you don't hear in the, in the complaining conversation is this, that if you are fundamentally someone who appreciates and understands how to get in the minds of someone who needs to learn something, you are going to be that person.

provided you get out of your own way and allow yourself to lean into some of these new resources and tools that business needs to help them create good content. And that piece of it, that's, what you're not hearing. You're only hearing how instead of me, the AI is doing all the work. And the, and the answer is the AI can do the AI gives you that flexibility.

Right. And I had no idea that this is where this conversation was going to go. but, but yeah, but just, but just think about the flexibility we were talking about a minute ago. The AI is giving you the ability to pivot. And one of the biggest problems with old L and D models that I'm sure many of us, anyone who's been in the career for 10 years or more understands you have those projects that got started back in the day and took forever. And when it was done, you realized.

Holly Owens (27:19.7)
Me either, but I'm loving it so much.

Holly Owens (27:44.588)
gosh. Yes.

James Gilchrist (27:46.819)
my God, if, we were, launching this, but if we had started working on it last month, we wouldn't be launching this. We'd be creating the thing that we actually need, but we have to launch this because this is where we spent all the money. So we have to start tracking how effective it is and did it move the needle and do we get an ROI? Blah, blah. But the joy of thinking smaller and bigger at the same time is that we have the tools that allow us to create the as need solutions.

Holly Owens (28:00.398)
Yep.

James Gilchrist (28:15.982)
when they are needed. And if we can all sit back and recognize that the business world as our lives is moving and changing so quickly that attempting to plant a flag at any point along that journey and say, this is where we're going to stay and we're going to live and we're going to focus on this problem and we're going to solve this problem is an outmoded way of thinking. You have to assume that you are, we are all running. We're all in a race and

The trick is to figure out what are the small things you can fix fast and quickly along the way to enable everyone else to keep running. You know, just keep people from stumbling. Don't worry about bringing them all back into the dugout and, you know, talking to them for 45 minutes about how to play the game. No, the game goes on. You got to fix it on the fly. You know what I mean?

Holly Owens (28:54.936)
Right.

Holly Owens (29:05.006)
100 % and I love the baseball analogy because it's, it's a fantastic one. So as we were coming to wrap, this has been a great conversation. I've loved what you've been saying here, but we have a lot of listeners who want advice, you know, you probably get, I'm just going to assume LinkedIn messages about how you're doing all that you're doing and doing it so well. I get tons of LinkedIn messages, especially from transitioning teachers about like, how did I get into L and D?

James Gilchrist (29:07.6)
Hahaha

Holly Owens (29:34.168)
How do I have this vast network? What did I do? Every time somebody asks me that, like, it's really not just one thing. It's a lot of different little things. kind of bring it all together. But coming from you, I'd love to know any advice you have for people who are looking to transition into learning and development or start their own business like you have. They really want some takeaways. They want to listen up. So they're like, what are the three things we can do today?

James Gilchrist (29:56.324)
Mm-hmm.

James Gilchrist (30:04.066)
Well, it's I appreciate the opportunity to speak to it. And I just want to say upfront that I'm going to quote Tom McDowell. As a matter of fact, I'm going to say, I'm not an expert and the, I don't know is a viable answer. but, but I will say, can, if for me to answer the question, the only way I can answer it is from my own experience. So that comes with that caveat, meaning.

Holly Owens (30:14.178)
Great.

Holly Owens (30:17.774)
Yeah.

Absolutely.

Holly Owens (30:30.87)
Yes, absolutely.

James Gilchrist (30:33.944)
I don't expect everyone who's listening to this to necessarily line up with everything that I think and nor do they find themselves in my circumstance. Everyone has their own and they're all doing the best they can to, to work within what they feel like are the constraints put upon them. So, so if you imagine yourself, if you're not a transitioning teacher and you're listening to this, just put yourself in there.

Holly Owens (30:51.182)
100%.

James Gilchrist (31:01.21)
put yourself in the mindset of someone who is in that situation. You're leaving what feels like a career that you have sunk your heart and soul into and countless hours and a lot of your own money in the hopes of making of helping people and helping people succeed. mean, that is the primary goal of teaching is that you want to lift people up. You want to help people do what they want to be able to do and give them good advice along the way. And now you are trying to find work in

Holly Owens (31:24.61)
Yeah.

James Gilchrist (31:30.37)
an arena where every like the ecosystem of education is nowhere to be found. So all, all the rules have changed. All the requirements have changed. All the expectations have changed. And yet the fundamental thing that you want to continue doing is the same. So there are a lot of what I call artificial constraints. Anyone can stand or sit as I am here and say, well,

Holly Owens (31:38.254)
100 %

James Gilchrist (31:59.629)
If you want to succeed, you're going to need to learn this and apply this and understand this and, and, basically buy into all of the reasons why what you do is different. Right. And the problem in my opinion, with that approach is that you will never get to where you're trying to go. You will be forever trying to learn the thing up skill, acquire the knowledge.

build the reputation, et cetera, et cetera. You will just be on a treadmill that never gets you where you want to go. So I would say this. Don't focus on what is different and don't focus on what other people are saying that you have to do first. Throw that out the window in my opinion and focus and focus instead on the area in which you would truly like to be teaching. Okay. Maybe you were an algebra teacher, maybe math, maybe

Holly Owens (32:44.557)
Love it.

James Gilchrist (32:56.066)
Math has been the thing that made you excited because you love the solving of the problems and you liked seeing the light go on in people's eyes when they realized, I can plug anything in and it works, you know, figure out what area of business is doing things that makes you feel this way. You feel about your primary area of interest, like what it is that you love, why you love teaching what you teach and make your goal.

Holly Owens (33:08.067)
Right.

James Gilchrist (33:25.764)
to be forming connections with that field and those individual companies that are doing that thing. In the day of ATS and resumes being, it's like, it's like processed food, right? The difference between food and processed food is the difference between the resume that in, that once upon a time was sort of telling a story and then became a thing designed for machines to.

Holly Owens (33:41.811)
god, I know. Yes.

James Gilchrist (33:53.827)
allow a hiring person to have less, resumes on their desk, right? That was the goal, right? Let me have to spend less time waiting through my applicants, right? So, so...

Holly Owens (33:54.359)
Right.

Holly Owens (34:04.726)
Right. What's so interesting to me is that we've created these barriers that people have created companies for to overcome these barriers. So there's ATS companies, companies that focus on the fact that you can't get through an ATS system and you pay them to figure out how to, yeah, anyways, that's a conversation for another day, but that bothers me. Yeah.

James Gilchrist (34:12.228)
Yeah! Yeah!

James Gilchrist (34:19.288)
Right. Yeah. It's its own thing. Absolutely. Absolutely. And, the, but the point here is that if you focus on the problem, if you focus on the obstacle, you will forever be focused on, you will forever be dealing with the obstacle and the problem, because there's always another way to try and solve that problem. Right. Because some, you know, you, you, as you said, the companies are lining up people on LinkedIn, people on social media lining up.

To give you the plan that guarantees that you will be able to jump all of the hurdles as the hurdles keep client, keep getting higher and higher and higher. Right. So my feeling has been, I look at my past, I look at my journey and I say, when did my moments of success happen? How did they happen? What, what were they the result of me efforting my way into the room? Or did they happen because suddenly a door opened because I was fully.

Holly Owens (34:50.035)
James Gilchrist (35:16.284)
because I was so focused on the thing that I wanted to do and was excited about that people came in to see what I was doing. The door opened and people came in. People came to me. I'll use another acting analogy. The difference between stage acting and being on camera has to do with whether you are putting yourself out there far enough for the audience to feel like they're inside you in a play and being so at one with who you are.

Holly Owens (35:40.408)
Yep.

James Gilchrist (35:46.533)
that the audience gets pulled into you when you're on camera. Okay. So I'm going to say, think of yourself as a movie star less than a Shakespearean actor. Don't be worried so much about what you're putting out so that people see you the way you think they need to see you based on your ever changing thoughts and what you're being told about what they need to see.

IE putting yourself in the box someone else created when they don't even know themselves what needs to be in it, but they're happy to tell you, you have to align with all those things. And instead focus on what brings you joy. And that's going to be really uncomfortable. It could be very uncomfortable to change your focus that much and to really start spending time with yourself and asking yourself. If I didn't have to worry about what anybody else thought of me, if I didn't have to worry about what anybody else said I should be doing. If I didn't have to worry about falling all of these rules.

Holly Owens (36:16.418)
Hahaha

James Gilchrist (36:41.9)
all of these rules. What would I do? What would I want to be doing?

Holly Owens (36:45.458)
my God, I'm super inspired right now. Need to reflect more. Yeah. Yeah, yeah.

James Gilchrist (36:48.207)
Right?

Yeah. Well, that's, and that's it. That's it, man. Slipping into my, as people say to me often, you said people reach out to you and ask you questions about this stuff all the time. Right. I'm like, people reach out to me and say, you're a little rough around the edges, but I like that about you. You're not quite so polished. Well, but the reflection.

Holly Owens (36:54.412)
Yeah.

Holly Owens (37:07.662)
I don't think of you like that at all. I really don't. I really don't. But that's funny that they say that.

James Gilchrist (37:18.488)
You are absolutely right. And that is really the heart of it. And, and more than any other thing, like, sure. I could say go where, go where there are fewer people. Meaning don't stand in the largest crowd and expect to be spotted. Right. And don't think, don't think of companies as fortresses. Companies are made up of people.

Holly Owens (37:39.074)
Right. Like Wado.

Holly Owens (37:47.992)
your hair.

James Gilchrist (37:48.817)
And they're just like, know now that everything that appears to be solid matter is actually made up of atoms that relatively speaking are miles apart from each other inside this thing. Anything we, you know, the table in front of me, I tap it feels solid, but it's actually empty space. It's mostly empty space made up of individual atoms. Well, companies are made up of a lot of space that exists between the people that run them.

And everybody has a job to do. So when you see a social media post, for example, don't think of it as the voice of the company, even though that's what the company wants you to think. The company doesn't want there to be any personal association with an individual. want to say this, this is our mask. This is our, this is our, our, our map to for success. This is what we do. A large scale structures, et cetera. But the reality is, there, there's somebody who worked till eight o'clock last night to make sure that that.

post went out and looked the way it did and made the last minute correction that their CEO demanded, et cetera, et cetera, et cetera. Talk to the company. Like you were talking to the people in the company. I have had so, so much of my success. have not, I have not like, it's not like I carved it out of the rock with a pickaxe. Like I'm, I'm, I don't, I don't like sweating. You know, I don't, I don't want to work really hard.

Holly Owens (39:13.73)
Yeah.

James Gilchrist (39:16.588)
on things that don't immediately give me a sense of joy as I'm working on them, right? Efforting is not my way. But when I look back at any success that I've had, I recognize it's because I have allowed, I have allowed the connection that led to the opportunity that led to the success. And we all need to be, I think, working harder, not, you know, joke.

Holly Owens (39:40.632)
Yes.

James Gilchrist (39:45.348)
tongue and cheek, we need to be working harder at allowing those connections to happen.

Holly Owens (39:53.89)
Yeah, 100%. James, this has been a great episode. I've really enjoyed this. Tell people where they can connect with you. Where can they find you?

James Gilchrist (40:04.572)
so it's a great example of not doing things the traditional way. I started Lighthouse L and D consulting because someone wanted to work with me and they assumed and they assumed that, they could, because they figured I had to be offering my services out as a consultant. And so I immediately said, yes, that is exactly right.

Holly Owens (40:17.972)
Okay.

James Gilchrist (40:32.33)
And my company is called this and I will be happy to work with you. And then I had to go create my company. had to create, I had to create a presence. had to create a brand. had to think about what I wanted to do. Now that isn't to say that two weeks prior to that, I hadn't stood in my living room and said to my amazing wife, Julie Sherwood, that, all the things that I was not going to do anymore, the things I was not happy about the things, the box I didn't want to put myself into.

and what I did want. just did a tirade to the universe about what I want and what I don't want. And that, in my opinion, is what that was the door. That was the door that opened. I opened it for myself. I said, I'm going to allow myself to believe that I can do what I want and not do the stuff I don't want to do. And two weeks later, somebody is reaching out to me, assuming I have a business and wanting to pay me. So, so I don't.

Holly Owens (41:25.954)
Yeah, that's awesome. I love that.

James Gilchrist (41:28.74)
So I don't have a website. I still don't have a website. I've been doing this for two and a half years. And the only place that I ever, the, I like to focus is LinkedIn. So I put all of my time and energy on LinkedIn. So people can find me at my LinkedIn address, which is basically the LinkedIn URL plus James Gilchrist L okay. Yeah.

Holly Owens (41:46.35)
We're gonna have it all, yeah. Yeah, it's all gonna be there for you. So I'm so glad that you're out of LinkedIn world. It's a great space. Some people kind of bash on it, but I don't know where I'd be without LinkedIn at this point in the community and the support and all the people that are there. I don't think I would truly be motivated to go and do these things you're saying, like find your passions. Don't do the things you don't wanna do, do the things you wanna do.

James Gilchrist (41:52.464)
That's it.

Holly Owens (42:13.962)
It's just, it's so inspirational. So thank you so much for coming on the show and sharing your experiences and talking with all these different things about us. I know the audience is like, probably like, wow, right now, and they want to come out and talk to you and everything will be in the show notes about how to connect with James at on LinkedIn. And of course, if you have questions, reach out to me, reach out to him. We're happy to support you. If you're making this transition into L and D.

So James, thanks so much for coming on the show.

James Gilchrist (42:45.534)
my absolute pleasure. Thank you for the questions. That's why I like to do podcasts because I never know what I'm going to say. And I don't know what I think until I say it. So you've just given me more clarity, which I love. And I just want to double down and repeat what you just said to anyone listening to the show. you. What, if you have a question, if you feel like you should be closer to the answer than you are, and you want to reach out to someone and get help, Holly is an amazing person to talk to.

Holly Owens (42:53.014)
Yeah.

James Gilchrist (43:15.04)
I am happy to talk to you. The field of L &D is full of generous people. And the only thing standing between you and getting those answers is your willingness to ask for the help that you need.

Holly Owens (43:25.76)
Absolutely. Absolutely well said.

James Gilchrist (43:29.531)
Thanks, Holly.

 

James Gilchrist Profile Photo

James Gilchrist

L&D Consultant / Online Community Builder

James Gilchrist is the Director of Lighthouse L&D Consulting, where he shines a light on organizations’ learning and development needs by designing performance-based learning solutions tailored to diverse industries worldwide. With a career spanning over two decades in learning leadership, James brings deep expertise in consultative L&D strategy, instructional design, and human-centered development.

Prior to founding Lighthouse L&D, James served as Director of Client Learning Programs at The Depository Trust & Clearing Corporation (DTCC) in New York City, supporting a wide range of financial services customers for 15 years. Now based in Lakewood, CO, he continues to grow his global network and speak on the value of authenticity in the workplace.

In 2025, James is leaning into connection and creativity: speaking on L&D-themed podcasts, presenting at conferences, supporting fellow professionals across industries, and proudly serving as both a DevLearn Conference Influencer and iSpring Learning Exchange Ambassador.

James is also a lifelong creative—performing original folk/rock music with his wife Julie (a trauma therapist and fellow artist), producing voiceovers and songs, advocating for wildlife, and mentoring aspiring L&D professionals. He’s as passionate about people as he is about learning—and whether it’s sailing the New England coast, composing a new tune, or helping someone land their dream role, he shows up with warmth, generosity, and purpose.