5 strategies to reboot your IT career

Here’s how to step out of the server closet and into a more robust (and possibly more rewarding) tech career

Technology changes faster than many of us can keep up with it. New paradigms like software-defined networks and the cloud emerge, and the old ones continue to hang around.

But while the hotshot programmers and big data geeks get to play with the shiny new toys, you're busy waiting for the robots to come and take away your job.

It doesn't have to be that way. Whether you cut your teeth on Unix and AIX or you tire of doing the necessary but thankless tasks that come with keeping the lights on and the datacenter humming, there's still time to reinvent yourself.

It won't be fast or easy. It will mean investing a lot of time and possibly some money, taking risks, and hacking code. But it can turn into a much greater reward, both financially and psychically.

Here are five ways you can reboot your tech career and take it to another level.

1. Apply your legacy skills to new tech

If you think only 20-somethings are in demand, here's the good news: Age and experience can actually work to your advantage, says PK Agarwal, regional dean of Northeastern University-Silicon Valley, which offers certificate and degree programs in business, management, and technology for busy professionals.

PK Agarwal, regional dean, Northeastern University-Silicon Valley

"With people who cut their teeth in the '70s, '80s, or early '90s, their education is much broader, and mental pickup is not that difficult" when it comes to learning new domains." -- PK Agarwal, regional dean, Northeastern University-Silicon Valley

People with legacy skill sets often have much greater breadth of knowledge than their younger colleagues, he says.

"As every profession evolves, it gets more narrow-banded," Agarwal adds. "With people who cut their teeth in the '70s, '80s, or early '90s, their education is much broader, and mental pickup is not that difficult" when it comes to learning new domains.

Your best strategy is to apply your existing skill set to emerging technologies, says Chris Ciborowski, CEO and co-founder of Nebulaworks, a devops consultancy.

Ciborowski, who calls himself a “recovering Unix engineer,” spent more than a decade building and managing large Solaris deployments, ERP and CRM systems, and web store fronts for a variety of organizations. For the past two years, he's been helping Nebulaworks clients create high-performance devops teams built around technologies such as Docker, GitHub, Jenkins, and Amazon Web Services.

"For me, it was looking at my skill set, at the things I do well, and adapting those skills to the new new," he says. "So as new technologies and processes were emerging, I looked to where I could draw parallels to what I'd done in the past, then take the things I was really good at and leverage them into Web 2.0 or Agile 3.0 or whatever we're calling the new initiative."

For Ciborowski, it meant taking risks, making sacrifices, and devoting nearly all of his spare time to getting up to speed on the "new new."

"It's about diving in," he says. "I spent all my nonworking hours thinking about it and all my working hours trying to build things."

Once you've leveraged the skills you have, you need to update them with newer versions of those skills, agrees James Stanger, senior director of product development for CompTIA, an IT industry trade association.

But you'll also need to update your mindset and geek culture references.

"I was talking with a guy who was a real green-screen Cobol kind of programmer -- he had long white hair and a long white beard, like Gandalf of the Mainframe," says Stanger. "The question is, What are the skills that Gandalf needs to pick up, so he can work with the Hobbits of the world again?"

One of Gandalf's tasks was to modernize his analogies, says Stanger. Instead of mainframes, think of the cloud; instead of terminals, substitute smartphones.

"You don't have to jettison what you know," he says. "But you do need to start analogizing and bridging your experience from the old to the new."

2. Get your code on

As Marc Andreessen famously wrote in 2011, software is eating the world -- which means the demand for developers has never been greater. Today, the hottest tech jobs are software engineers, software architects, and UX/UI designers, says Shu Wu, director of tech recruiting site Indeed Prime. The positions least in demand: network and database admins.

Shu Wu, director, Indeed Prime

"Every company is trying to hire tech talent. If you put effort into learning programming languages ... you have a chance to transition yourself from someone who's less in demand to someone who's more in demand." -- Shu Wu, director, Indeed Prime

"Every company is trying to hire tech talent," says Wu. "If you put effort into learning programming languages like Java, Python, and Ruby on Rails, you have a chance to transition yourself from someone who's less in demand to someone who's more in demand."

That's why many bread-and-butter IT folks are heading off to programming boot camps to get their coding skills up to speed.

Shane Biggs was working as a sys admin for an accounting firm in Washington, D.C., when he saw a Dan Rather news report about a coding academy called DevBootCamp. That was enough to convince him it was time to go back to school and become a developer.

Biggs had a couple of network certifications under his belt and was making decent money running a small IT department. But a future spent hooking up monitors and mice didn't hold much appeal.

"The job felt boring and stale," he says. "I've always had a more creative side, and I felt like coding would bring that aspect into play, almost like an art."

It took him two years, but the former poly sci major finally saved up enough money to quit his IT job and move 3,000 miles to San Francisco, leaving his pregnant wife behind. Tuition for the nine-week course cost $12,500, plus living expenses.

Now he's back home, working as a front-end developer for a marketing agency in Baltimore.

"I didn't really fall in love with coding at first," he admits. "It was really hard, I felt like an idiot. Now I'm addicted to it."

Chris Duflo spent five years consulting on Oracle Finance implementations for Hitachi and later Deloitte. But he got frustrated designing complex solutions, then handing them off for someone else to implement.

"I thought, If I can design this, I might as well learn how to build it," he says. He enrolled at Origin Code Academy in his hometown of San Diego, in part because it specialized in .Net and JavaScript, skills that were in heavy demand on job sites like Dice and Indeed.

Now he's a front-end developer, working for a firm that creates electronic voting solutions for a handful of U.S. states and the Academy of Motion Picture Arts and Sciences.

The biggest revelation for Duflo, whose prior programming experience consisted mainly of writing SQL queries, was how well his previous work experience translated into his new one.

"I really thought those five years I spent as a consultant were wasted," he says. "I quickly realized in interviews and the workplace that I knew a lot more than I thought I did. I had picked up a lot about general data architecture and terminology. It may not translate to the keyboard, but in meetings and design and conceptualizing it's really valuable."

3. Become a dev advocate

You don't have to be a coder to be a vital part of a dev team. Take Tori Wieldt, who started her career as a sys admin working on legacy Unix systems for SBC Communications in the late 1980s.

"They still had a lot of vintage equipment back then," she says. "Some of the machines were so old we had to flip switches to change their memory settings."

From there Wieldt began working for Sun Microsystems in a variety of jobs: tech support, technical writing, website management, and finally, managing the Java developer community after Sun was acquired by Oracle.

Now she works as a developer evangelist for New Relic, helping to build out the app performance monitoring firm's dev community and to organize its FutureStack conferences. She does it despite having rudimentary coding skills.

"I have learned enough Docker to be dangerous, but do not consider myself a programmer," she says. "But I understand what developers go through and how they interact with the technology, and can communicate that both internally and externally."

The ability to combine good communications skills with a basic foundation in coding can make you highly marketable as a developer advocate, says Whitney O'Banner, campus director and career developer at the Austin Dev Bootcamp.

"Developer advocates are in especially high demand, particularly at technology companies that encourage third-party use of their back end, like Facebook or Pinterest," she says. "Working knowledge of APIs, solid communication skills, and a passion for product and customer service are the perfect recipe for success in this role.”

4. Find your tribe

But it's hard to go it alone, not to mention counterproductive. Today's IT environment is about communication and collaboration. In a recent survey by IT staffing firm Modis, IT managers identified teamwork and interpersonal skills as the ones most difficult to find in job candidates.

James Stanger, senior director of product development, CompTIA

"Certification is a great way to leverage a community. ... You're getting distilled information that tells you, 'Here's what the community is talking about, so join in.'" -- James Stanger, senior director of product development, CompTIA

Developing your soft skills are more important than ever, says Agarwal, as is networking -- the personal kind. The key is finding a community of people who are already familiar with the latest technologies.

"A lot of people in tech just don't have the networks," he says. "We always encourage our students go to meetups and conferences."

If you can afford the time and expense, going back to school is a good way to both develop skills and make contacts, says Paul Smith, VP of business development for Peak Technical Staffing.

"These days most organizations have teams develop their code, and half the job is going to meetings to talk about where the projects are going," he says. "In a classroom environment you have classmates you can bounce ideas off of and work through things. That's something you usually don't get from studying online."

Another option is to enter a certification program in the areas where you want to develop new skills, says Stanger.

"Certification is a great way to leverage a community," he says. "The certs are created by hundreds of people in the CompTIA community, all of them experts. You're getting distilled information that tells you, 'Here's what the community is talking about, so join in.'"

Of course, there are plenty of online resources. Biggs recommends freecodecamp.org, a free online code academy, and Code Newbie, a community of people learning to program that offers internships and holds meetups in cities around the country. Weildt says she gets a wealth of information from Slack channels devoted to dev issues, such as devopschat.slack.com, for devops, and fedsonslack.com, for front-end devs.

5. Know when it's time to leave the nest

Trying to build a new career while maintaining your current one is a bit like trying to change a tire while driving on the freeway. Unless your employer is on board with your reinvention process, you'll likely have to pull over to the side of the road and do it on your own time.

"The best way for an IT veteran to reinvent themselves is to build up a portfolio of side projects," says Max Brown, founder of Silicon Beach Talent, a tech recruiter. "This won’t happen overnight; it takes time to learn new skills, either through self-study and online courses or through a coding boot camp."

Chris Ciborowski, CEO and co-founder, Nebulaworks

"If you don't start now, you're going to be behind the eight ball because there are already a lot of people who are trying to reinvent themselves." -- Chris Ciborowski, CEO and co-founder, Nebulaworks

If your employer isn't supportive, you may be able to find an early-stage founder willing to take a chance on you, says Brown. Or you may have to take a deep breath and strike out on your own.

"I realized that in order to flex my wings I couldn't do it within the confines of an organization that didn't understand personal and professional growth," says Ciborowski. "I certainly didn't have that at the place where I was working. So I needed to find either (a) a company willing to take that risk with me or (b) set out on my own and give it a shot outside the walls of 'corporate America.'"

If you're going to make the leap, it helps to have partners who can complement your skill set with those of their own, he adds.

"If you are thinking of starting a company around any of the new technologies, you need to have a balance," Ciborowski says. "There has to be a yin to your yang, or it's not going to work. You can't all be Unix guys."

There's no need to panic yet, he adds. But the time to get started is now.

"It's not like you're going to wake up tomorrow morning and there's not going to be any VMware or AIX environments left," he says. "But if you don't start now, you're going to be behind the eight ball because there are already a lot of people who are trying to reinvent themselves."

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