Are you ready for Big Sur? Join Apple experts Bradley Chambers and Tom Bridge on Oct. 7th to learn how to prepare for Big Sur and the future of Mac management. Register today

IT Specialization vs. Entrepreneurial Thinking with Van Romine | Where’s the Any Key Podcast Episode 9

The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Ryan Bacon: Welcome to Where’s the Any Key? The podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud® Directory-as-a-Service®.

Introducing Van Romine

Ryan: Our guest today is Van Romine. He is the IT manager at Inland Valleys Association of Realtors. Welcome Van, thanks for coming on.

Van Romine: Well thank you, Ryan. I really appreciate it. 

Ryan: Sure thing. So, why don’t you tell us a little bit about yourself? 

Van: Well, my title probably sounds a little bit strange. What does an IT manager do at a non-profit association of real estate? I’ve been IT… oh my gosh, 1982… so we’re coming up on 40 years in IT, and actually I was a math and physics major in college. So I think I only took about three or four computer classes when I was in college. I do remember taking a binary programming class. All the programming was in ones and zeroes. I took a Fortran class and that’s really the only formal training. So most of my IT experience was all on the job.

Ryan: Experience does count for a lot, and I bet you’ve seen a lot of changes over the course of your career.

Van: You know, I very rarely get asked to show off my binary programming skills anymore.

Ryan: I’d imagine not. 

Van: You have to keep up because the old stuff kinda just disappears.

Ryan: Yeah, even for things like Fortran and Cobol, there’s still a pretty big demand for that out there, with a lot of financial systems and stuff like that are still being run on old school mainframes. There’s still demand. 

Van: Can tell you a quick story about that?

Ryan: Go right ahead.

Van: So we’re here at a Real Estate Association and one of the things that we like to do for our members is crunch data. We love to crunch data and give some sort of intelligent analysis of what that data tells us. So one of the things that we looked at was property tax data to look at valuations and property tax rates, looking at that. We went to our local county and said ‘we would like to get a copy of the property tax database.’ They said, ‘sure, no problem. That’s public records and it’s free to have.’ So we got it on a CD and it was one big file. It was in a Cobol-encoded EBCDIC. 

Well okay, most people haven’t even heard of the word EBCDIC. EBCDIC is the mainframe equivalent of ASCII. So when you have ASCII codes and ASCII characters and ASCII encoding, well there’s a mainframe version of that even beforehand called EBCDIC. Oh my gosh! I had to pull out my EBCDIC notes from 1983 to figure out how to decode all that, but we did. We managed to decode several million records of property tax data, do our number crunching, and produce it. So sometimes, it does pay to be old.

The Debate Begins

Ryan: Well like I said, experience is everything. So, that kind of leads us into what we’re going to talk about today. So, how we’re going to format this episode: Van and I are going to have a discussion about specialization in IT and then entrepreneurial thinking in IT. We’ll discuss what we mean by entrepreneurial thinking. To start with, we’ll say that this is going to be focused towards IT people. Different types of jobs are going to approach entrepreneurial thinking in different ways and everything like that. So we’re going to have a conversation where I’m going to take the side of, I’m going to advocate for IT specialization; Van is going to advocate for entrepreneurial thinking, and then we’ll recap and discuss at the end. Sound good, Van?

Van: It’s perfect.

Ryan: Alright. To start with, why don’t you start off with explaining a bit about entrepreneurial thinking and kick it off with it’s a good idea.

Van: Well, there’s probably two things to say about that. I mean number one, true entrepreneurs are individuals all by themselves. You’ve grown up with people that you know; you got friends and neighbors and family members that you know. Some people just have the knack: they’re so creative and their ideas are popping out of their head like balls in a gumball machine right? You don’t have to be an extreme entrepreneur to have a good appreciation for business and business opportunities. As an IT person, I believe it’s so helpful to be able to appreciate the business parameters, the business challenges, and honestly sometimes and I believed this most of my life, that sometimes there are no good technical solutions to people problems, but there usually are good business solutions to those kinds of issues. 

So when you’ve got that many more tools in your tool kit, and you can expand your range of solutions to not just be technical focused but really look at the bigger, broader landscape and and bring and apply business solutions, entrepreneurial Solutions, Creative Solutions… outside the the standard IT handbook, I think I think your chances of success — both personally and professionally — go way up.

Ryan: Okay, well that’s good and all, but, and I’m going to try not to be too confrontational about this, I want this to stick to… 

Van: Oh go ahead, bring it on!

Ryan: Okay. You bring up looking at the different business side of things, and I mean really, people into IT to work with technology: to tinker with computers, to administer databases, to work on networks all this sort of stuff. When you start implementing and putting in those business aspects, it really does start to muddy the water. It starts pulling you away from the stuff that you’re passionate about.

Van: Absolutely. I’m going to be the first one to admit: you’re right. It makes your life more complicated. It makes… maybe you lose a little more hair, maybe you’ll lose a few more hours of sleep, but it’s rare that you find that many IT jobs, other than academia. In Academia, you’re given that opportunity to be a bit of a purist, and you can really kind of ignore the business aspects because that’s really removed from the needs of your job. But other than an academic environment, there are rarely IT positions where you are impacted, even just simply by budget constraints. So, I would still argue that there’s very few people that can safely ignore, in their IT position, the bigger world outside them from a business point of view.

Ryan: So I would even add to that list: large corporations also tend to be heavily siloed. So, you can get, for example, I did an internship at Google. In that environment, I was on a team doing physical security, so we managed access control, security cameras, radios, guest check-in kiosks, and that was it. If we needed a VM spun up, we contacted the VM team. Heavily siloed. So therefore, you have your opportunities for specialization. In your role on your team, you have a very clearly defined role and very clearly defined responsibilities. When you start adding in those business elements, it’s like ‘do I need to be concerned about this?’ This software that I want or this piece of hardware that I want costs $2000. Do I need to worry about that or do I just tell my manager ‘this is what I want’ and then let them deal with the budget side of things, the business proposal side of things? Then, I can be like ‘okay I told them what I wanted. I can continue on doing my job now.’

Van: I wish I had a job like that. I wish I had a job where I could dump all my requests on this table and say ‘let me know when you get all those things purchased and delivered and I’ll get back to my job.’ You know it’s funny you talk about Google and the silos. It’s a very valid point. I don’t want to dismiss what you’re saying. Now, I will have to say I’ve got gray hair and you don’t, so unfortunately, my examples are not going to be as recent as yours. You talk about Google. Well back in the day, the Google of my generation was IBM. 

We used to brag that IBM wasn’t in the Fortune 500. They weren’t in the Fortune 100. They weren’t even in the Fortune 10. They were in the Fortune 1. We were in the top of the Fortune for years and the magazine ranking of businesses. If you have ever thought about silos: oh my gosh. IBM was famous for having silos. Department boundaries and rules and responsibilities and span of control and all of that. Now I will say the reason that IBM is not so dynamic and so much at the top of the tech industry anymore is for that very reason. Those silos were a real weakness in the long term. The second part I would say though is, and I’m going to push back a little bit to say, even even in an organization like Google where there are those kinds of lines of responsibility and boundaries that you’re not really required but highly recommended that you don’t cross those boundaries. I’m going to throw out the word that — I know it’s a dirty word; I am sorry — politics. So even if you don’t have business responsibilities or business control, there is so much politics everywhere you go. Understanding the politics of your IT career, politics of your IT project, it never goes away. It’s always in the background.

Taking Multiple Paths in Your IT Career

Ryan: Well this brings on another thing. Nowadays, a standard career progression is not necessarily your company and you stick with them for your entire career. You bounce back and forth. So that lends itself to, if you’re at a place and you’ve got your experience but the politics get to the point where they’re not jiving with what you’re looking for… time to take my next career step. So, even if you’re looking at specialization and just looking at sticking with a more technical-focused career, you can still avoid the politics and therefore not have to worry about it too much. If it gets beyond your certain threshold, you can move on and it’s perfectly normal and perfectly acceptable nowadays to do that.

Van: You know, you make a good point. I mean I don’t want to support your argument too much here, but you know back when I was starting out my career, a manager told me one time, he said ‘In your life, you’re going to have more than one career. You’re going to have several jobs and you’re going to work for several different organizations. Even if it’s in a big company, you’ll move around. But you will have at least two or three major career stops along your way.’ Honestly, that was a little bit unusual to hear that 30-40 years ago. Now, like you say, that’s expected: jumping from job to job is almost a way to enhance your career because of the experiences you get. Because of the variety and the exposure to new technologies that you wouldn’t get if you were stuck in one place. So I do get that. I don’t want to support you too much on that, but I will say that no matter where you go, politics goes with you. So that would be my argument.

How Do You Progress Your Career with Entrepreneurial Thinking?

Ryan: Okay, I’m going to return the favor of your support, and I’m going to ask you a question. I’m going to serve one up to you. When we’re talking about career progression and like a career path, when you’re specialized, it’s really easy and it tends to be defined. You want to be a network engineer? Okay, you stay with your Net+ certification and some schooling and then you go on to your Cisco certifications or whatever. There’s a clearly defined progression of how to get to the next step. With entrepreneurial thinking and bringing in the business side of things, how do you progress your career? How do you determine what the next step is?

Van: Well that’s really hard. I will be the first to admit that the roadmap for an IT career is a lot more defined. I would say that there is the unexpected in the IT world. There’ll be some new innovation and you might even overlook it because you’re so good at one thing and then this new idea comes along. You’re kind of a little skeptical. ‘Well, that’ll go away. I’ll stick with what I already know.’ So there are risks to specialization because of that. But you’re absolutely right. In the business and entrepreneurial space, it really is about managing all of the unknowns. It’s all about taking risks. It’s about, the big word now is disruption. Be a disruptor. That’s where the big money is, that’s where the entrepreneurs like to be. Honestly, there is as much disruption in technology more than almost in any place. So being entrepreneurial and being willing to be adaptable is huge. 

Now, I’ll tell you a quick story. In probably the last say 5 to 10 years, we’ve seen a huge switch over to cloud computing, and I happened to be a big AWS fan, but I’ll be honest. It was hard for me. Are you kidding me? I came from IBM. If I wanted to go look at my computer server, I would go down to the hall, and I’d use a badge at the badge lock. I’ll put in my secret code and I’d go into a raised floor, 5000 square foot facility with air conditioning blasting in your eyeballs, and I would go hug my mainframe computer. I’d watch the tape drives spin and I’d see 10 megabyte disk drives that look like small refrigerators. So, when you compare that kind of history with logging onto a website with your credentials and spinning up new virtual machines on AWS… wow! I mean, it is mental gymnastics to make that switch. 

So being an entrepreneur, you’ve just got to constantly push yourself. I would say this: whether you’re a specialist or maybe a little bit more of a generalist, I would say you cannot afford to be complacent. No matter what path you pick, you’ve got to push yourself. Just when you get to be comfortable and you like what you do and you’re good at it and you’re the top of the heap, that’s when you need to start saying ‘Okay, what’s next. What do I have to unlearn, and what do I have to learn anew, because something is going to come along and I’ve got to be ready.’

How Do You Become an Expert Through Entrepreneurial Thinking?

Ryan: Yeah, you talked about being at the top of the heap… when you get to that point and you become that subject matter expert within an organization. You become that go-to person, a lot of people find that really fulfilling. Specialization makes that really easy. How does entrepreneurial thinking and how does that business element play into that? 

Van: Well, I knew guys throughout my career who have been extremely intelligent, and like you say, at the top of their game and at the top of the heap… and but they’re always looking over their shoulder, too. They know that if the question changes, I’m sorry they’ve only got the same old answer to give. So it’s the disruption that has happened in the last 5 years, in the last 10 years, there’s been more technical disruption then we’ve seen in the last hundred. So I think it’s funny when people say ‘well I would feel so much safer in my job if I could count on the fact that my skills would be so valued that people can live without me.’ I’m sorry, I don’t know any IT person that can say their skills are so good that they are irreplaceable. You can’t think like that. That’s such a recipe for disaster for anybody and I think that entrepreneurs get that. I think a little bit of entrepreneurial business perspective teaches you to be nimble, agile, flexible, learn new things, manage risk, juggle… those are all really basic human skills that I think every  person should develop and should have.

Ryan: This is going to be me supporting your point this time. I’m sure you’ve heard the saying there’s that saying that irreplaceable is unpromotable. That’s something that you have to consider. If you’re going to be the best at something in an organization, you’re going to find other people moving up alongside past you. If that doesn’t bother you, great. If you’re in your happy spot, perfect. It’s something that you have to consider.

Van: I’ll tell you a quick story. I remember, years ago, when I met somebody and I said ‘hey, tell me about yourself. Tell me about your background.’ And I’m sorry, this story is about IBM. I hate to keep bashing on poor old IBM. I said ‘how’d you get started at IBM?” and they said, ‘Oh well I’ve been working here 20-25 years,’ and I said, ‘that’s great! How’d you get started?’ They said, ‘oh, well my dad worked at IBM, and my grandfather worked at IBM and I kind of inherited their job. I kind of took over their position at IBM,’ and I go ‘Are you kidding me? Three generations of people, and one after the other followed in the very footsteps of the generation prior to them. You would never hear that story.

Ryan: That’s unheard of nowadays.

Van: I remember that story. It’s absolutely true and it wasn’t the only person I heard that from. We live in a different world. We live in a global world, and I know it was global 50 years ago and a hundred years ago… Man, I keep talking about fifty-year-old topics, I’m sorry about that, but it’s true.The global pace of change is amazing. I’ll tell you a couple of areas that scare me: artificial intelligence and machine learning. You know why that scares me? It just blows my circuit. I have no idea what that’s all about. I get it: I can look up the the dictionary definition, but I could not sit down and say, ‘Yeah, I’ll just work on a little AI today. I’ll just work on a little machine learning problem today.’ I would not even know where to start! 

There are technologies and specializations today that I would not even… if you didn’t start out early in your life, when you’re 20-25 years old and your brain is quick and plastic and moldable, and shapeable… forget it. I am way too old to learn some of these new technologies, can’t do it.

Ryan: I think, based on what we were talking about, I think it’s a good time to kind of merge the thoughts together, because full disclosure, I’m right there with you. I feel that understanding the business side of things is very important. I personally get a lot of satisfaction from that in my job and it could very well be my background talking. I’ve gone through career changes. My education: you know I have a degree in accounting. I did my Master’s in IT but I also did my graduate certificate or you can look at it as my minor to my Master’s was in business intelligence. So I am fascinated by all that stuff. 

On the more practical side of things, that kind of knowledge and the willingness to use it has led me to situations where I can write up a business proposal: ‘I want a new networking stack for a new office, a different one than what we’ve been using. I understand the technical side of things. If you can understand the technical side and the business side, you can put together a proposal that just knocks the socks off of people, where whoever looks at it is like ‘okay, that makes sense.’ When it comes to the budget, understanding business needs and budget, I’ve gotten to the point with our finance team, with the people who approve these purchases that if by the time I bring it to them, I’ve done my homework. They understand I’ve done my homework, and it’s built that level of trust. Is it a guarantee they’re going to sign off on it? No, but they know that I’m not just their choice that you’re wasting their time with with frivolous requests.

Van: Right. I was in the conversation yesterday with a couple of business partners that I work with out of Canada, and at the end of the conversation, I really wanted to reinforce for them my number one goal. I think it’s appropriate for some of my final thoughts with you in this podcast. Every conversation that I have, whether it’s IT or business or whatever it is. Even in personal life, it has to be a win-win. When you’re dealing with other people, it’s got to be a win-win. If you say, ‘well if we do this, I’m going to benefit’ and if you never talk about how the other person is going to benefit, they’ll tune you out. They won’t care! It could be the greatest networking stack on the planet, but if you can’t tell the finance people or if you can’t tell your CEO or your boss how it’s going to improve the business or save money or do something for them, why would… Why should they care?

Turning Decisions into Win-Wins

So I guess maybe the bottom line for me is you, take away the politics. Take away business, take away entrepreneurialism. Take away all those words, and just boil it down to this: whenever you want to accomplish anything in your career, always think in terms of win-win. You can’t just look at it from your point of view and say ‘well this is the best thing for my situation, from my side.’ You’ve got to be able to talk to other perspectives of the other person and when you can lay out your ideas and your concepts and your strategies and your recommendations in language that helps them win in their problems, and win in your problems and everybody wins… wow, that’s pretty compelling.

Ryan: That is, and to add another layer on it, when you look at IT in the vast majority of organizations out there, IT is a cost center. IT does not generate revenue. It’s really, in most cases, you can’t make you know the whole ROI (return-on-investment) arguments for purchases and stuff. So you have to look at those win-wins. How is this decision or purchase going to improve the business functions? When you boil it down to it, that’s IT’s job. It’s our job to make the rest of your organization work better. So if you can tie in what you want, and how the benefits to you are also benefits to them, you’re set. 

Van: Bingo. You got it, you got it. The guy gets promoted first who makes his boss look good. So I think we’re on the same page. I mean, I know we kind of tried to be kind of fun about this and take two different points of view. However you define it, whatever words you want to use, it just gets down to just good common sense. When you talk in terms of ‘we are all going to benefit. We’re all going to win if we do this.’ People pay attention to that. 

Understanding Your Job Market

Ryan: Let’s add another element into here. I was going to bring this up in talking about the pros of specialization but it’s really not, at least not nowadays, and that’s how you fit into your job to job market of your area. You kind of alluded to this: new technologies change and I was originally saying if you’re specialized, you can customize your career path, your specialization to the job market that you want to be. ‘Oh there’s a huge demand for DBAs here, so I’m going to hunker down and learn SQL and all this stuff. I’m going to be a DBA and that’s what I’m going to.’ The fact of the matter is, things are changing. There’s disruptions happening all the time where what works in your job market now may not be as much in demand 5 years from now. Heck, it might not even be much in demand 2 years from now. Having that flexibility, understanding business needs, being able to adapt and fit yourself into what your job market needs is critical. My IT career has been as a generalist for pretty much that very reason. Every role that I have been in, the organization has had different needs. 

Van: Well, let me make this even more complicated. I don’t want to take a rabbit trail if we do if we don’t want to do that, but it wasn’t maybe six months ago that I was kind of looking around. I had a little extra spare time. It thought  I’d be interested in contract work. They’ve got these websites like taskrabbit and your various websites, where you can just say, ‘I’ll bid on a  programming job for XYZ and make a little extra cash,’ and I kind of was curious. How would that work for me? Would be something that I could do? Maybe I might do a lot of it, but I’ll at least try one… are you kidding me? I got out on there and I started looking at it and I realized that what I was seeing as competitors was people that were coming out of Pakistan and Asia and all kinds of locations, and the problem with it was I couldn’t compete! They were billing at ridiculously low rates, you know $10, $15 to do work. I would starve to death if I had to compete against these people. I could never do it! When you play on a global stage, the competition is fierce. You think you know something and then you go out you look, ‘well yeah there’s like a billion Chinese people that know how to do it, too. What are you going to do about that? It’s ridiculous; it’s just so hard. If you don’t think big enough, you can get surprised by what’s out there, what the options are, and what people know, who competes, and what they’re willing to work for… it’s amazing to me. 

Ryan: Also, as you get further along in your career, as you get older and that sort of stuff, you may want to to adjust your trajectory. If you’ve kept the business needs, the business side of things in mind over the course of your career, making that adjustment, if you want to go into the management side of things, if you want to go instead of the more business operations side the things, which I found IT tends to lead really well into that, it’ll make that transition a lot easier for you. I recommend it to anyone. I don’t want to knock people who want to specialize, because you never know. It’s one of those things you never know until you try it. I’ve started down many different paths. I think when I got onto IT, I wanted to do networking. You start off as a generalist, and you know what I found that is as a generalist, there’s just so many interesting facets of IT. It’s hard for me to pick just one.

Van: There you go. I agree with you totally. In college, I was a physics major, and as a physics major, you have to take a lot of math classes. What I found out pretty quickly was if I just took a handful of extra math classes, I could also have a math degree. So that’s what I did. It’s kinda like that in the IT world, where if you get good at networking, then you realize that it bleeds over into so many other disciplines: security, systems administration. If you have any kind of curiosity… well, I think I’m a little biased. I think IT people are not only good-looking, but I think they’re also very curious people, and if you’ve got that kind of curiosity, it’s so hard to specialize because you’re always interested in… ‘oh my gosh, look at that! You mean I can go into this area? I can go explore that new topic?’ You’re almost working against your own nature when you specialize, because if you’re curious about IT, everything’s interesting. 

Closing Remarks

Ryan: Truer words! Oh man, this has been great. So we’re reaching towards the end of our time. I think we touched on everything that we wanted to discuss… is there anything else you want to say to close things out? 

Van: I don’t know if I have some huge pearls of wisdom here that I want to part. I think in a lot of ways, the conversation that you and I’ve had is in a microcosm. It’s very typical of what every IT person will discuss with themselves over their lifetime. There will be moments in your conversation like we’ve had where you’re really thinking ‘wow, specialization is exactly what’s going to really fit me right now.’ 

Then you can do a little different stage of your life, like a different stage in our conversation, where you say, ‘Wait, maybe a little bit of business smarts would really help me out in solving this problem.’ It’s just an ebb and flow. I don’t think that there is a single answer, but I do believe, just like this conversation, there is movement back and forth. There’s times where it works, and sometimes it’s better to be the other way. I think that’s where everybody just needs to remember: be open, be willing to to change your mind and change your skills. Add to your skills and don’t be afraid to take those risks. Being flexible is really the answer to most problems. 

Ryan: Couldn’t agree more. Thank you very much for coming on, Van. It was a very enjoyable conversation Again, our guest is Van Romine, the IT manager at Inland Valleys Association of Realtors, and it’s been a pleasure!

Van: You too, Ryan. Good luck, and I hope you enjoy the rest of your career as much as I know it sounds like your career up to this point. I can see the joy in your face, so I hope I hope that smile never goes away.

Ryan: I appreciate it.

About JumpCloud

JumpCloud Directory-as-a-Service is Active Directory and LDAP reimagined. JumpCloud securely manages and connects your users to their systems, applications, files, and networks. Try JumpCloud now, or contact us at 855.212.3122.