Career Coaching Tips to Level up Your Career

Rusty Wilson is a Certified Ethical Hacker, and a Hacking Forensic Investigator, among 10 other professional certifications. He's carried the titles CIO, CTO, and VP of Technology.  All the while he pursued his passion for providing strategic career development coaching for IT and engineering professionals. He discusses professional development tools and the importance of soft skills for engineers.

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Rusty Wilson
Cyber Career Coach
Rusty is a 24-year veteran of the Information Technology services and support industry.  He has a Master of Science degree in Information Security and Assurance, from Western Governor's University, and holds certifications from Cisco, GIAC, Elasticsearch, Microsoft, CompTIA, ITIL, EC-Council, CIW, and others. He has worked as a Senior Cybersecurity Incident Response Handler, software engineer, network manager, systems administrator, IT project manager, and held executive positions, such as Chief Information Officer (CIO), Chief Technology Officer (CTO), Vice President of Technology, and served in Director of Operations roles for the Army and Air Force.
 
After serving on active duty in the United States Army and many years of learning, testing, trying, failing and succeeding, Rusty developed techniques that put his career progression into over-drive. He has figured out what works and what doesn’t, and used these techniques to explode his career and life success. His passion is sharing his education and experience with others!
 
Rusty has provided one-on-one career coaching to students, business owners, and employees from small businesses to fortune 500 companies, including military and civilian employees of the United States Armed Services.
David "Ledge" Ledgerwood
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Your host, Ledge, is a many-time founder, with deep experience in growing six-figure startups to 8-figure enterprises. Clients talk to Ledge first when exploring a relationship with Gun.io.

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Transcript

DAVID LEDGERWOOD: Rusty Wilson started his career as a signals intelligence analyst in the U.S. army where while deployed in Korea, he cut his algorithmic teeth on Perl scripts that ended up slicing days of processing time for his intelligence data processing for “big data” was even a catch phrase.
Rusty is a certified ethical hacker and a hacking forensic investigator among ten other professional certifications. He's carried the title CIO, CTO, and VP of technology. All the while, he pursued his passion for providing strategic career development coaching for IT and engineering professionals, wisdom he shares with us in this episode.
Rusty, thanks for joining us. It's really great to have you here.

RUSTY WILSON: Thanks, Ledge. I appreciate you taking the time to have this discussion with me.

LEDGE: Awesome! Just for the audience, can you give a two-minute intro to tell your story and tell people where you're coming from and where you're going.

RUSTY: Sure thing! I'll try to keep it to two minutes. It's interesting, to say the least. I grew up in a really small town in rural Louisiana. I remember when we got our first computer at the high school, it was something that I was drawn to. I really enjoyed figuring out how to solve problems and build menus and things like that.
Out of high school, there really weren’t a lot of opportunities besides going to work offshore or going into construction unless you were to go off to college somewhere; and, frankly, I was not interested in the prospect of going to college. I felt like I had done enough learning, so to speak, at that point ─ or, at least, I wanted to take a break.
The opportunity to join the U.S. Army as a signals intelligence analyst afforded itself to me; and so, I took advantage of it and spent the next six years in the United States Army as a signals intelligence analyst. I got to go to a lot of places: Korea; Fort Campbell, Kentucky.
But an interesting thing happened while I was in Korea. I got the opportunity to learn UNIX; specifically, I figured out that I could solve some problems that we were having that took a long time using Perl to write scripts and applets that would turn what would be a one-, two-, or three-day job into a thirty-second task. So that's really where I got the bug.
After that, I started learning more about system administration, about UNIX; of course, that was not long before the transition to Windows for work groups. And then, finally, the network technology domain ─ Windows domains came out and I sort of headed in that direction.
Eventually, I got involved in networking and learning that kind of stuff. I went the CISCO certification route. I was a Brocade/Foundry engineer. At one point, I used to run all the networks at Fort Polk, Louisiana. And then, it was sort of a natural progression of career. You move into management with less hands on which, frankly, I didn't enjoy that much.
During that phase about 2013-2014, frankly, I was really bored. I was doing a lot of reviews of personnel. I was working for the Air Force at the time at the Department of the Air Force Civilian and I had about 70 or so folks working for me and about probably 60% of them were contractors; the rest were military folks. We had to do their performance reports and that was dying a slow death for somebody who likes to solve problems and likes to be hands on keyboard.
During that time, I decided I've got to pull myself into something. And so, I started a blog called “Cyber Career Coach” at cybercareercoach.com. Immediately after starting the blog, I thought, you know, I think I'd want to do a podcast and start interviewing folks and just talking about things that I've struggled with and, sometimes, continue to struggle with and maybe crowdsource it.
That's kind of where it started. And then, probably after my fourth or fifth interview, I interviewed a gentleman named Jason Ingalls who was doing Internet response for major companies all across the United States. It sounded really exciting.
We stayed in contact. He actually invited me to join him on his Internet response engagement so I took some time off of work and did that. I had the most fun I'd ever had with my clothes on.
After that, he offered me a position of chief information officer with his firm which I did for a couple of years. And while I was there, we developed sort of learning about Big Data, ElasticSearch and how to use that effectively for cybersecurity incidence and to really begin to correlate data from very different locations and put that stuff together and put a picture together of through the network and their activity.
And we ended up building a virtual reality application that could visualize net flow. But we needed more data. And so, as a result, we ended up starting a managed detection and response capability.
I built out the underlying data analytics platform for that and we actually made this very short list of Gartner MDR companies two years in a row, 2017 and 2018.
Before that, I transitioned to the chief technology officer for Ingalls; and about September, I got an opportunity to come to work for a company called “B.E.A.T. LLC” as their VP of technology to help on some big data initiatives they were doing.
That's where I've been for the last few months. I really like it. It's a San Antonio company which is where I'm at. There's not that much travel so I'm home with my wife and kids and I can devote more of my spare time back to the podcast because I'm not on the road as much.

LEDGE: That's fantastic! What a great path! You touched a lot of bases there. Off-mic, you and I were talking about how you really have this passion for connecting with people particularly technology professionals and this coaching practice, and that really fits nicely into what we're doing on the sourcing side; it's just helping people to be professional freelancers.
What does that mean and what are soft skills necessary?
I'm sure you're finding ─ and we tend to find ─ that it's just not enough to have excellent technical skills, to know how to pass a code, test, or any of those things. There's this other huge piece of the pie: the professional acumen, the communication, soft skills, and all those things.
What do you touch on when you're dealing with technical professionals that the audience can walk away today with some tips there?
RUSTY: That's a really great question. There used to be a skit on Saturday Night Live where the IT guy would come into the room and everybody would say, “Hey, IT guy, I need your help with X” and he gets over there and says, “Go here” and he just says, “Move” and he shoves them out of the way and jumps on the computer and fixes it. And things like that are funny because they're rooted in truth.
Early on in my career, that was something I struggled with ─ a lack of patience ─ because when you know the answer and you know how to get to the root of the problem, it's very hard to sit and watch somebody go slowly.
And this is why folks who have a background in help desk support and dealing with customers usually have an easier time with things like interviews and sort of winning the job.
I spend a lot of time with the folks I work with helping them to overcome the limiting beliefs that they have within themselves. I don't want to create any generalizations here because there are folks who do this kind of work from every kind of background imaginable. But I find that a lot of folks are gamers and they spend a lot of time in their basement or their bedroom playing World of Warcraft or EverQuest or what have you; and that's kind of what got them excited about doing this kind of stuff.
They often their own servers and they needed to learn how to do those kinds of things. And that's sort of what sparked this interest for them.
I wouldn't say that most folks who do this kind of work can be socially awkward. I think that with technology, with the prevalence of social media, with the fact that we do everything on our phones and we communicate what happens, that personal connection, that one-to-one interpersonal communications, and those interpersonal communication skills that happen face to face are somewhat, I would say, not comfortable. Some folks are not comfortable in that scenario.
You've got to figure out how to be who you are, be yourself, and also be open to others. And I think a lot of folks who do what we do kind of struggle in that area mostly because we are so good at using communications technologies like our phones and the computers and things like that.
Again, I hate to generalize and I don't think it's fair to generalize but for a lot of the people I deal with, I think that's been their number one frustration. It's not that they don't know how to do the job; it's that, often, they have a hard time communicating in an interview-type scenario or face to face with someone.

LEDGE: We see that, sometimes, and we often will stand up next to an engineer and help them sort of choose words wisely and things of that nature. I have to say that where I have seen some absolutely brilliant engineers fall over on a project is the communication side. It really is just “Hey, I was out there writing my code and I was doing a great job and I was checking in my code everyday.”
And then it turns out that the client had an expectation that maybe so and so was going to regularly write a physical update or was going to show up for a particular stand-up.
And because that communication wasn’t shared and expectations weren’t set, the engagement didn't work out.
It's not about the code that was written. The code that was written is beautiful but the level of expectation is higher particularly for a senior professional. And that can be a tough pill to swallow and a tough news to deliver for us. We don't like that. We like to see people to be successful.

RUSTY: Absolutely! It's funny that when you get into coaching, you think it's going to be helping people decide which certification to take based on their skillset. You're going to help people figure out how to sort of lay out the groundwork and the roadmap for their career because it's, essentially, career coaching and helping people get the most out of their career.
A lot of folks are just unhappy. They'll get a job. They're unhappy in their job and they think, I need to find a new job. And so, they start searching for ways to improve themselves or get more certifications or things like that.
Often, it's not the job. It's their outlook; it's their attitude; it's their approach to life.
It's important to find balance, and balance is not just about necessarily family and home life. It's your recreational time. It's your spiritual. And it doesn't matter whether you believe in one God or its Buddhism or you believe in the earth of whatever. But there is a spiritual component to the self that needs to be fed, and that's another part of balance.
It's your financial life. I find that, often, for folks who are really miserable in their job and hate their job, it's really not their job so much; it's because their swimming in debt and they see no way out. They're not making enough money to necessarily pay down their debt. And so, that translates to this unease in every aspect of their life and it begins to bleed over.
One of the things that I really try to work towards is finding that balance, ensuring that you're doing things in your off time that feed your passions and that allow you to sort of get these things off of your chest. I think a lot of people just carry this work along with them.
A job is a means to support yourself, right? And you can do the work that you love and still hate the job unless you can get everything into the right perspective. It helps to sort of work on all these other aspects of your life.
That's kind of what the Cyber Career Coach community has sort of turned into. It has turned into more of a mindset overcoming limiting beliefs and breaking through barriers and leveraging the power of the law of attraction and understanding the secret to success. That's sort of the direction everything has gone.
It's been a great learning experience for me. It's helped me to recognize and address some of the shortcomings and the limiting factors of my own success.

LEDGE: That was going to be my next question. What have you been doing differently over the years of learning from others and through the experience of others ─ your “coachees,” if you will? What have you taken back to your work and done differently? What successes have you had from that experience?

RUSTY: One of the things that I think has brought a lot of benefits to me is trying to be helpful. In other words, there's sort of an entrepreneurial aspect to even doing a job, and that is the whole idea of finding a need and filling it.
So just because something is someone else’s responsibility or just because it's not your “job,” it doesn't mean that it's not somewhere you can step in to either assist someone else or help them by just being present and being available.
I'm sure you understand the concept of flow. When you're working on something, especially when you're working on code or scripting or debugging, you have to focus. And focus is such a premium that interruptions can take you off track.
We have this initial gut reaction which is like a lizard brain. Your aggravation for being interrupted is all over your face and you carry it in your body language. And that was something that I dealt with constantly.
And so, this whole process of coaching others sort of helped me to recognize that character flaw within myself and begin to work on not reacting negatively when there's an interruption but to handle that situation more effectively.
I think it makes interpersonal communication better.
And then, you can very politely ask someone, after the fact, “I'm working here. Next time, if you need something, could you just give me a second” or whatever. There are ways to handle that more delicately, and it depends on the situation, obviously, and whether or it's your boss ─ but certainly with peers because your relationship with peers really can impact either negatively or positively your environment at work. And it doesn't matter if you're on a job as a consultant or if you're working as an employee.

LEDGE: Absolutely! That's a good point. We do hear about flow and, actually, that comes up a lot with engineers. Good software engineers do not like to work on too many things at the same time. They want to dig in and solve the problem.
We were primarily in remote environments so that we have to remind people often to make sure you have the discipline of checking in because the silence is just deafening when no one can see you working and no one sees an update. And so, you really need to focus in on how to deliver the level of community necessary ─ and really over deliver on that because no one can see you doing the work unless you have that activity stream. And that itself can be distracting if you don't handle it the right way.
What's your feeling on remote work? Are you coaching anybody who deals exclusively on a remote environment? How would you advise people to make changes to achieve that?
Many people love to work from their home office. For the professional freelancers that we deal with, that's the thing.
Do you have people like that or do you think about people working in this new remote economy? What advice would you have for them?

RUSTY: I mostly work from home. And the biggest challenge for me working from home was not what you would think as far as keeping yourself motivated. I tend to work too much, and that's the problem. I had to put boundaries around when I work and where I work within the house to, essentially, keep the peace and to make sure that I was not neglecting my wife and my family but also to ensure that I was taking breaks because we end up sitting for hours.
That was a learning experience for me as well when I transitioned to mostly working from home, and that's where I am now.
I would say the thing that helps folks who are working from home especially if you have multiple clients is staying organized, and there are lots of tools to do that.
Trello is a great tool specially for developers. You have the ability to do collaboration there. If you're working with a company and they're using a tool like Trello or Slack or Asana (Monday.com is a great project management tool), that allows you to create and track milestones.

But any kind of collaboration tool that allows you to provide updates as to what's going on with your project or what have you is something that can be leveraged for positive good things to ensure that you're communicating effectively with the people you're working for so they know that you're engaged and that you're busy.
There's a balance between having tools like that which will give you notifications throughout the day and having uninterrupted time for sprints.
There are a lot of really good techniques. From a development standpoint, if you talk about the Agile framework or Scrum and having sprints where you're working on some section of code or some specific function, you can do that throughout your day. You can establish a one-hour or a thirty-minute sprint to work on some section and then stick to that sprint. Work that sprint during that time. At the end of the time, summarize the work that you've done and put that into Trello or update the person you're working for because you're going to bill those hours.
And so, it's good to have sort of an activity report. It's not only good for the customer to know that you're engaged but it's also good for you because, later on, you're going to go after other engagements, other gigs, and opportunities and it will be good to have that sort of little journal of information.
It doesn't have to be a lot ─ one or two lines ─ to show the kinds of projects that you've done and to demonstrate your effectiveness. It will help you tell that story better.

LEDGE: Fantastic advice ─ couldn't said it better myself. That's great. Rusty, thank you. It's great to get your insights. Where can the audience look up more stuff about you if they're interested in your services?

RUSTY: The website is probably the best starting point, and that is cybercareercoach.com. And then, there's also the podcast which is available on both iTunes and Stitcher. That's the Cyber Career Coach podcast.
Those are the two best places. We also have a Facebook page. You can just search for that on Facebook.
I'm on LinkedIn as well.
I'm in the process of transitioning right now to move more towards a crowdsource initiative because what I'm finding is that there a lot of great stories out there that I don't know about. And the way to find them is to sort of bring this community together.
So I'm going to be creating a Facebook group pretty soon that will allow folks to begin to collaborate more with like-minded individuals. It's kind of like a large mastermind group, if you will, so we can start bouncing ideas off of each other and get advice.
I'm a firm believer that a rising tide lifts all boats and there is so much going on in a rapid change of pace within technology. I've been focused mostly on cyber security but I believe that there is so much opportunity in all the cyber fields and we can all help each other.
This is the enabling industry for all other industries as far as I'm concerned and I would really want to help as many people as possible. And that's the goal of doing all this to begin with.

LEDGE: Awesome! Thank you. It's great having you, Rusty, and we'll look forward to seeing you grow the community.

RUSTY: Thanks, Ledge. I appreciate your time.

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