Have you ever looked back at the twists and turns of your career path and wondered how each step led you to where you are today?
Our guest, Ryan Gilbreath, joins us to share his journey to where he is today.
From the childhood dream of becoming an archaeologist to beat-making in college, Ryan’s story is a great reminder of how our early passions often pave the way for future successes.
Interview Highlights
- From Business Graduate to Digital Project Manager [00:45]
- Ryan wanted to be an archaeologist as a kid, inspired by movies like Indiana Jones and The Mummy, and his interest in Egypt.
- Ryan’s fascination with archaeology stemmed from his father’s interest in history, particularly African and Civil War history, and their discussions about Egypt.
- Ryan highlights his curiosity and love for discovering new things, mentioning that this trait has influenced his current job.
- He emphasizes being a curious person who enjoys digging and learning, connecting his childhood interest in archaeology to his present-day approach to his work.
- Transitioning from Archeology and Music to Business [02:31]
- In college, Ryan shifted his interest from archaeology to wanting to be a producer, enjoying making beats with friends and the creativity involved.
- Michael draws parallels between archaeology and project management, highlighting the common theme of digging into details to uncover motivations and goals.
- Ryan explains that the shift happened partly because he didn’t want to endure the extreme heat of archaeological sites.
- Ryan’s interest in music, particularly playing drums and participating in drum circles, sparked his passion for on-the-spot creativity and collaboration.
- He connects the collaboration in drum circles to his current role, emphasizing the importance of everyone playing their part for a cohesive outcome.
- The Shift to Business and Tech [05:12]
- Ryan pursued a business degree in college without a clear career path.
- Dreamed of working in New York studios post-college but questioned the long-term lifestyle.
- Ended up exploring other options and eventually landed in the tech industry.
- Ryan’s Journey into Project Management [06:21]
- Contract jobs with Capital One, including technical rep and project coordinator roles, exposed him to project management.
- The experience at Capital One led Ryan to pursue a career in project management, starting as a project manager at an agency.
- Ryan acknowledges the need to catch up on skills early in his career, especially transitioning from a corporate environment to an agency setting.
- Ryan highlights the evolving nature of project management, with a focus on continuous learning and adapting to different project needs, including the challenges of implementing Agile in certain client scenarios.
- Collaboration and flexibility are essential in project management, and Ryan stresses the importance of meeting people where they are and fostering a collaborative approach.
As Project Managers, we often receive opportunities to practice skills in real-time. Embrace these chances, trust that things will work out, and accept that failure may be part of the process. Learning from failure provides valuable insights and knowledge that you can apply to future projects.
Ryan Gilbreath
- The Importance of Soft Skills in Project Management [12:24]
- Ryan highlights his strength in creating a comfortable environment for people to be at ease and feel vulnerable, fostering open communication.
- Emphasizes the importance of being personable, authentic, and making people feel comfortable, which he considers a significant factor in his success as a project manager.
- Ryan discusses the stereotype of project managers as analytical and details-oriented, but acknowledges his own area for improvement.
- Expresses the desire to excel in resourcing and financial projections, recognizing the need for extra effort in ensuring accuracy.
- Emphasizes the importance of utilizing tools, dedicating sufficient time, and being self-aware to improve in these areas as a project manager.
- Ryan acknowledges that his initial strength lay in soft skills, providing opportunities to learn and adapt quickly.
- Reflects on the importance of having both hard and soft skills, stating a desire to have perfected hard skills earlier, but also grateful for the development of soft skills over time.
Starting out, the soft skills opened doors for me. If I had only relied on hard skills, I wouldn’t have been memorable.
Ryan Gilbreath
- Final Thoughts and Advice for Aspiring Project Managers [16:03]
- Ryan emphasizes the importance of giving oneself grace when entering a Digital Project Management role.
- Acknowledges that DPMs bring various skills and experiences, urging them to be aware of their strengths and areas for improvement.
- Encourages a commitment to the learning process and understanding that skill development takes time.
Meet Our Guest
Ryan Gilbreath helps designers, developers, and strategists ideate and execute faster to launch digital solutions that matter. With a passion for mission-focused products and organizations, he brings 8+ years of combined experience in digital media, information technology and marketing working with diverse teams for startups, businesses, and organizations. He has delivered hundreds of projects across various media including websites, applications, and services.

It’s about working together and finding the best solutions collaboratively. It’s a give and take.
Ryan Gilbreath
Resources from this episode:
- Join DPM Membership
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- Connect with Ryan on LinkedIn
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Read The Transcript:
We’re trying out transcribing our podcasts using a software program. Please forgive any typos as the bot isn’t correct 100% of the time.
Michael Mordak: Hey, it's Michael from The Digital Project Manager and welcome to today's Member Spotlight! We've managed to strain together the biggest and baddest collection of project managers who are out there creating change and challenging the paradigms that exist in projects today. This community is full of people who probably wanted to do something totally different with their lives.
But, while we all come from a diverse set of backgrounds, roles, and industries, we found our calling organizing the chaos that is—project. Our unique stories have been shaped by the lessons we've learned, the skills we've developed, and the people we've met along the way. If you want to join, or just learn more about membership, check out our website at thedigitalprojectmanager.com/membership.
Today, we're speaking with esteemed community member and digital project manager Ryan Gilbreath. Ryan, like many of us, did not know what he wanted to do as a career. A business degree got his foot in the door in an entry level customer experience role, and from there, he had an opportunity to switch roles and support the PM team as a coordinator.
After gaining experience, he was able to find a role as a PM within an agency where he has continued to hone his craft. We'll hear about Ryan's journey as a digital project manager, how he draws from his interests to excel in his role, the importance of soft skills, and how they can help you move up the ranks from coordinator to project manager.
Ryan, I just want to start by thanking you for giving me your time today and for being here to answer some questions. But I want to jump right into it and find out from you what were your plans when you were younger? What was kind of your dream job? What did you want to be when you grew up?
Ryan Gilbreath: That's a really good question. I actually have that written down. I did exercise back in my mid 20s about that actually to enhance my self awareness a little bit of where I want to go. But I remember as a kid distinctly wanted to be an archaeologist. I was fascinated by it because of the movies I watched like, you know, Indiana Jones and The Mummy. I was fascinated and also to my interest in Egypt.
So my dad was really big into history, especially African history and Civil War history, which is random, but we also talked about Egypt together. And I was really curious about going and discovering and digging and finding potential artifacts, mummies, of course. So it always fascinated me. I've always been fascinated about Egypt in general.
And it's funny, that skill of just that curiosity and discovering new things. And also I've used that in my job. I'm a very curious person. I like to dig. I like to learn. I've definitely taken a form of that into what I'm doing now. And then as I got into college, I wanted to be a producer. So I remember I loved making beats in my dorm room.
I loved doing it with my friends. And also too, just that curiosity, that way of doing something new, doing something creative, I really enjoyed that. So I would say between the archaeologist at my younger age, I was a kid, and then being a producer when I was in my college years, it's funny how those skills and that what I like doing, I've kind of showed up at the one I'm doing now.
Michael Mordak: Yeah. I mean, it's so funny because they might sound like really different jobs, especially new project management. But as soon as you said archeology and prehistoric, both of them, I was immediately dry comparisons. Like, Oh, wow, that would actually be so fantastic because you do have archeology, like you mentioned, you're digging into things, you're discovering. But getting to the right, like the actual answers, you can't just stop at the surface level when it comes to why someone's doing something or what the real goals really are.
So you can really see those underlying kind of desires and motivations are still able to tie those into the job that you have now. That's really interesting. And so I love that journey. I love how you go from archeology and then to PM, but they're able to dig a little bit more into maybe some of the more granular details of that.
Like when you mentioned like when was that shift from, okay, maybe I won't be an archeologist, but I'll go to college for production?
Ryan Gilbreath: Yeah. I mean, I think it's funny. It's sort of like that shift just happened because the kid has sounded cool. But then it's funny. It was so like, it's such a childhood reason.
I didn't want to be super hot in the desert. That's about it. Right. It was bad. And I was just like, I don't know, maybe I need to rethink this. And then, as I got to a teen, I was like, I was in the marching band and I was in the program and I really loved playing drums. I was percussionist. And I really love playing the drums.
I love being in, especially, I'll call it a drum circles. It's not the hippie drum circle, but it's like the drum circle where we're all practicing. We're all making a beat from the fly and each person is contributing to that melody to, to that cadence. And just the on the spot creativity was something I really enjoyed doing, it was like that collaboration.
If I actually want to pin that because when you are part of the band, when you're a part of a drum line, there is a sense, there is a big like the collaboration that you're bringing to it. Because everybody has to play the part in order for that song, for that melody, for that cadence to the shot. And I see that today now, like vibration, wanted to be a producer and Archaeology digging deep.
I mean, it's crazy. It's funny talking about this now, but it's crazy just how those things have come into what I'm doing now in my career. So, yeah, I would say that's what draw me to that.
Michael Mordak: So that's what got you into college for production, wanting to pursue that. And then...
Ryan Gilbreath: Well, that's actually funny. I didn't go to school for production. I actually went for business management.
Michael Mordak: Oh.
Ryan Gilbreath: Yeah, yeah. So that's a generic degree. Like, I didn't really know what I wanted to do in college. And so getting a business degree, I was like, all right, well, at least I have my business degree. Then, you know, it's something, it'll translate.
As I got into college, I was really interested in the musical arts, like production, things like that. And then once I got out of college, I definitely pursued some things for a while. So I had dreams of going up to New York, working in the studios up there. But then I had to ask myself, is this the kind of lifestyle I want long term?
So that also pivoted me toward like exploring some other options, which is where I landed in tech. And yeah, I'll stop right there.
Michael Mordak: That's awesome. And honestly, like there are so many comparisons I'm drawing between your story there and what I personally went through as well. Because obviously I think a lot more people are like this too, but you go off to school post secondary and similar to you, like, I had no idea what I wanted to do at all.
And just, I had the same thought process. I was like, Oh, business, I'll just get a bachelor of commerce degree because that I can go into whatever I want, I guess, really, it's just so general. And so, I mean, clearly it worked out because like you said, you're able to find an opportunity. And so what was the first opportunity that came up across your plate that, that really got you leaning towards now?
Ryan Gilbreath: Yeah, so when I graduated college, I landed a couple of contract jobs with the Capital One, working one as a technical rep, basically doing a lot of research and customer service calls for a new bank teller integration software. If I was doing a lot of testing and just research doing that. And it wasn't until I came into my other contract job as a project coordinator at Capital One, where I really got to see like, huh, this looks interesting.
This is a big enterprise project that's been going on for a couple of years now. And the part I get to play in here is supporting the team, supporting the project managers to making sure that they have the data, they have the information, the resources that they need to do their job. And from there, you know, that I took those skills working at Capital One and wasn't until I came into an agency role as a project manager, which later turned into a digital project manager.
I guess Web Project Manager in like the mid 2010s is when I started to see, Oh, this is actually pretty cool. It's actually working on website, web applications here for small businesses. And just the fast pace of it, the three, six month projects, as far as that being that long, really fed into just my, okay, get in, get out.
I want to get this done. I'll move on to the next project while I learn all I can about this project and move on to the next. That really intrigued me.
Michael Mordak: I love how you got a little bit of a taste for it and got to see how the PMs were working and then slowly make your way toward that and you work toward that as a goal. And I think, I mean, one reason why I really liked that story is just because I feel like it really highlights the fact that it's not like one of those stories where you had one goal that you knew as a kid, you were working toward everything you did was built around that.
It was more like playing it by ear almost, and just leaning into the things that you found interesting, which I find it for the uplifting and a little bit different.
Ryan Gilbreath: Yeah, but you know, I mean, I feel like that's a big part of it is one of those things where you come out of college, you have a goal, you have a destination. But sometimes there can be a pivot and you take that pivot, you go to find something else, you find something else that you didn't know about yourself that you actually intrigued by.
So, I mean, it's definitely a journey.
Michael Mordak: And just curious, would you say that maybe because you were more open to these like pivotal moments where you're transitioning and changing, do you think that like you were maybe always trying to catch up or work up to all the other people were at?
Or do you think that you were able to quickly adapt and didn't really have a big effect in the grand scheme of things?
Ryan Gilbreath: It's a good question. You know, there were definitely times where I did feel like I had to play catch up early on just because when you go from working as a project manager in a corporation, especially a big one, like Capital One, there's a lot of procedures, standards, methodologies that you have to follow very to the T. You know, it's not a lot of flexibility sometimes, especially when I started out 2010, that's when I graduated college.
And during that time, Agile was not, especially Capital One was not really a big thing, mostly Waterfall. And so I remember seeing it as a project coordinator, I didn't manage projects at Waterfall, but I did a lot of projects being managed in a Waterfall way. And so as I started to get more experience, I started working in the agency, I started to learn more about Agile and how to work within a different framework.
And so there was a part of me learning, catching up. I'm pretty sure a lot of project managers, you know, DPMs have YouTube, religiously, they get caught up on their skills, just try to use all their resources just to, and I'm not ashamed to say it, just to act like I know what I'm talking about. A lot of stuff that we get as Project Manager is like, we'd always get those opportunities to practice those in real time.
We have to find an opportunity to do it and just trust that it's going to work out. But at the same time, understand that there's going to be failure attached to it, and that's okay. Like, it's not the wrong with failure as long as you learn from it. You can gain valuable insights and knowledge and you can take that to your next project.
Michael Mordak: I think it's a great point that you bring up and can reinforce that. Because I've had people that reach out to me and say, that a lot of reasons why they either read our publication side of things or join the community and keep up to date with the Slack channel, for example, or read the publication to pull some insights from there and pull resources from there just to be able to bring that back to their coworkers or back into work.
And then just make it sound like they know more about what they're doing and really just real collective knowledge rather than having to try to like figure it all out and trial and error themselves.
Ryan Gilbreath: Yeah, no, and that's a big thing. I hear Galen, I hear a lot of PMs in this space who have been, who have more experience than I, working in this field for a number of years. It's still an evolving practice, project management is. You know, like they're, what I've learned working in agency setting is that Agile sounds great, but most of the time doesn't work for every project because you got clients coming in who do not understand what Scrum even means or what, you know, and they're just like, I just want you all to listen to me, got my requirement, and build my product.
And they don't want to hear like, Oh, well, you're going to be a product owner on your side, owning the product. You're going to be a business stakeholder. They're like, what? What does that mean? And did you have to educate them along the way? And most of the time they're willing to learn, but do they have the intentionality and commitment to actually embrace that?
Not always. And so that's the thing too. It's like, you know, I learned this less than a while back that, you know, I can come in there, I can get Scrum certified, I can bring in these processes, but if I'm going to be rigid and just hold to it and then force people to do it, to me, that's not being agile, especially in an agency setting.
I have to meet people where they're at and it's all about collaboration too. I have to be able to collaborate with people and get the best workout with people that I can. It's a give and a take.
Michael Mordak: Tying that back to your experience as a percussionist like you mentioned, right? Like we need to be able to collaborate and really drive everybody together.
Ryan Gilbreath: Good point.
Michael Mordak: Yeah. That's a good point.
So we've actually talked a little bit about, your experience before and things that kind of experience and things that you brought over from past interests. But are there anything maybe that we missed that you wanted to highlight areas that you were that maybe from like previous job experience or anything like that really gave you advantage when you were transitioning into the PM role?
Ryan Gilbreath: You have a good question and I want to talk about that too. So thanks for bringing that up. I think one of the strengths I have as a project manager for me is just my ability to help people be at ease around them and to feel vulnerable with me. That's something that I've always noticed. I'm already talking about it a lot, too.
Other people talk about it, like, just being personable, giving people space to feel comfortable bringing things up with me or even problems on a project. And I use that and I'm thankful for that because it has helped me in my career. And I've also put effort into honing that as well, too. And knowing when to use that and knowing when to bring that, bring myself to the table, which has also led into nowadays, especially in this day and age, is being more authentic at work as well to be my breaking my authentic self.
I think that's a big part what has helped me be successful in this role. It's just being authentic, being personable, making people feel that ease around me, but it's helped me a lot in my career. And let me ask another question about, well, I'll be at that question. I know the question that you had on there about what has been the things that you wish you would have learned or like tried to hone better, right?
Michael Mordak: Yeah.
Ryan Gilbreath: Yeah. So around that, I would say one thing I have learned about myself, I think the stereotype with project managers is that they're very analytical, don't say a lot, very shy, or just very like, details, deep policy, which is still a point, yes. But one of the things I wish I was an expert in, just a superstar in, but it takes a little more work to do it is the resourcing piece and also to the financial projections.
That's the part that takes more work on my side to make sure that my number is accurate, which means that it takes more time, it takes more trial and error, and just making sure that my numbers are right. So I think that's one thing that that's not my superstar strength. But it is something that I have learned over time to utilize tools, to utilize time, to give myself enough time to make sure that I'm putting the focus in to make sure that what I'm giving, when I give my projections, that they are right.
It takes planning, it takes making sure that you're aware of that and that when you do deliver that, that you're putting the time and energy into it to make sure that it is a good report that you're sending out. So I think that's one thing I would say for project managers who that's not always necessarily their skill, like utilize tools, utilize the time you have to get that right and figure out what works for you. Be self aware.
Michael Mordak: Yes, I actually, I think that's really interesting because what you're mentioning really is that you kind of had the soft skills that you brought over, right? You'd like that approachability and be able to create safe spaces and having patience for people. Whereas maybe some of the more like technical or hard skills, I guess you'd refer to them where it's actually like scheduling and grading budgets and that kind of stuff are areas where you need to upskill.
But I think that's really, I mean, from what I hear, would you say that's the more ideal path or do you, is there a part of you that kind of wishes you had the hard skills and the soft skills or would it have been more beneficial to you starting out?
Ryan Gilbreath: That's a good question. That's a really good question.
You know, I would say yes and no. I think starting out the soft skill to what got me into opportunity is where I could jump in and learn and adapt and just think on my feet, think smart. If I would've came in there just with the hard skills perspective and I didn't have soft skills, I wouldn't be rememberable.
And so I'll say yes and no. I'm at a point now where over the last, almost 10 years now, I've been able to hone those skills, like scheduling, like I'm, you know, scheduling, resourcing, budgeting, it definitely comes natural to me. But it definitely took time to get there. I would say that I think it's a yes and like, yes, I do wish I would have had those hard skills perfected a little early on. And I'm also grateful that my soft skill came natural. I was able to hone that and spend time on that as well too.
Michael Mordak: No, that's a great point. I love the way you put that. There's so much more I want to dive into. This was a great conversation. Unfortunately, we're out of time. It flew by. It really did.
But I just want to thank you, Ryan, for your time for coming on today and sharing your story, sharing your experience. Because I think that it's maybe I'm being biased and selfish, but really people and I think it'll really help people hear some of the things that they need to hear, like that things take time.
People don't always have it figured out from day one, and it's okay to be adaptable. It's okay to at times feel like you need to catch up because the resources are out there. Whether it's community or whether it's taking a certification or just simply trial and error that, you know, the resources are out there to get caught up.
So it's wonderful. Thanks for sharing all that.
Ryan Gilbreath: And if I can add one more thing about, okay. Yeah. And to your point, give yourself grace as well too. Know that you're coming into the DPM, you are, I'm pretty sure you're coming in with a lot of skill and a lot of different experiences. So, sometimes you don't always have that time to hone those skills, but give you some grace. Know where you're at and know what you need to level up on and just commit to the process.
Michael Mordak: Wonderful advice. Thanks so much for sharing that.
Ryan Gilbreath: Absolutely, Michael. Thank you.
Michael Mordak: Thanks for tuning into our Member Spotlight with Ryan. He has so much more knowledge and insight to share with you. So, come chat with us in the Slack channel, along with our entire community of digital project managers. You can learn more about membership on our website at thedigitalprojectmanager.com/membership.
Until next time, thanks for listening.