Skip to main content
Exploring what’s next in tech – Insights, information, and ideas for today’s IT and business leaders

How to avoid an IT career dead end

You may love what you do, but change is a fact of life in technology. Here’s how to stay a step ahead.

Every experienced technologist has had that gnawing suspicion: The cool technology you’re working with is in danger of running its course—and your usefulness and marketability is vanishing right along with it. Career dead ends are a pain and unemployment is a drag, so the questions are urgent: How do you know when it’s time to change horses, how do you pick the next ride, and how do you make the transition gracefully?

The problem is hardly a new one—technology has been evolving since it was invented—so I asked a bunch of smart people how they keep their skills fresh and relevant. Their answers were, interestingly, pretty consistent: Keep your ears open, stay curious, and be proactive.

You likely spent years developing expertise in your chosen niche. You’re comfortable with it, you can solve plenty of problems without effort, and you’ve developed a social circle wherein you know who to call upon. But at some point, you need to recognize that it’s time to move on.

It’s worth noting: If you’ve found a niche you like and it looks like it’ll be a good, safe, long-term ride, there’s nothing per se wrong with playing it out. There are still COBOL programmers doing good and important work. And there’s still a demand, I hear, for OS/2 jocks. The march of progress doesn’t necessarily sweep up everything in its path, and plenty of work can be found on the fringes, if that’s where you want to be. If the pond is smaller than it once was, maybe you can be a big fish. You be you.

Where did everybody go?

If you’re less confident about your technology’s (and your job’s) future, however, it pays to be paranoid. Ganes Kesari, a co-founder and head of analytics at data science company Gramener, suggests that your efforts to keep up with your current technology of choice can provide signs that it's time to move on. A drop-off in the number or rigor of conferences in your area of expertise or a lack of online courses or new books may indicate you’re on a sinking ship.

Social interactions may be a tip-off, too. “During business networking events and chats on work technologies,” Kesari says, “if one often gets blank stares with a quick change of topic to alternate skills, that might be a sign of one turning into a tech dinosaur.”

Keep your head in user groups and meetups. Who’s showing up, and why? Are people excited? Are they just getting together to whine about the lack of opportunity, or are recruiters circling? Is attendance getting bigger, or do you see the same (or worse, fewer) regulars?

A radical change in competitive landscape is another sign it’s time to aggressively embrace change. I spoke with one director-level marketer at a software company who said his company was just sold to a private equity firm and his boss left. He says it’s “lighting a fire under me,” which may be an understatement.

“It’s super-helpful to have trusted folks at a variety of different companies to bounce thoughts off and get different perspectives,” says a programmer I’ll call Monty. “Our world is moving much too fast for anyone to keep up on their own.” Like many techies, he has changed focus frequently over the years. “It’s been pretty clear when it’s time for a change,” Monty says. “I think it’s really important to spend a bit of time regularly reading about what’s going on to get a sense of which way the winds are blowing. And being open to change is super-important for everyone.”

“When you're in it on a day-to-day basis, you can lose sight of the fact that you're treading water,” says Dary Merckens, CTO of Gunner Technology. Periodically pull back and take an objective look at things, he advises, and set goals to learn something new. “Try and figure out where the tech landscape seems to be moving. And then just take a risk and dive in and learn something. That's what a job in technology is: constantly learning new stuff.”

And all of this begs the question: How do you know in the first place that you’re stuck someplace you don’t want to be? “There’s a variation of the Stockholm syndrome in the technological field,” says Sophie Miles, CEO of CalculatorBuddy. “And you can suffer it, on another level, when you feel terrible in your work but you are unable to 'abandon' your colleagues to your fate or 'betray' your company looking for another job.” That’s especially so if you’re the only person around who can maintain a piece of software or administer some obscure system.

“But if most of the time you feel bad in your work and that discomfort is affecting your private life, maybe it's time to throw yourself into the professional market,” Miles says. ”Think of yourself; companies have many people who think about them.”

It’s critical to keep your ears open. Talk to friends, read blogs and the trades, and trust your gut.

What’s the buzz?

Then, when you do jump, where do you jump to? You’re going to be a beginner, all over again. If you have to invest in learning something new, you might as well choose a career path that might last—if that is even possible.

One way to go about it is to choose a specialty that is about a role rather than a technology. If you see yourself as a front-end developer or a data management specialist, the tools you use are just items in a toolbox. They may not be interchangeable, but they’re a means to an end. If you label yourself as a Novell Netware expert or XML guru and you build your career accordingly, your options run out as soon as the keyword-heavy job listings dry up.

By putting your attention on developing expertise in a role too, it’s easier to convince yourself to add to that toolbox. Plus, when it does come time to move to the next shiny thing, neither you nor prospective employers perceive that the earlier knowledge is wasted. Instead, you can confidently explain that you have a balanced toolset and you know when to reach for the right hammer.

“The half-life of any digital technology is 18 months,” opines game industry guy Craig Trader. “This means that half of the details of what you know about technology X will be obsolete in 18 months. So, if you're not learning something new about X continuously, you can be pretty sure that in three years, you'll want to have upgraded your skills or learned something else complementary.”

If you do want to find the next bandwagon—the one where early experts earn the highest salaries—look for “when competing technologies become the darling of media/startup ecosystems,” Gramener's Kesari says. Don’t follow every bright shiny object. But, he says, it may be worrisome if a craze continues well beyond the point where the hype is expected to cool down.

A better option is when you can anticipate media hype instead of following it. “You know the time has come to switch to the newest thing when techies talk commonly about it but the business world is just starting to notice,” says Tim Kulp, director of emerging technology at Mind Over Machines. “That is the best time to be on your way learning the newest thing,” he says. “It is a time free from clear understanding, where you can work with your audience to define what to expect.”

The State of Hiring: Learn how 101 IT execs find staff for critical positions and cajole in-demand tech specialists to accept their job offers

“I watch the consumer space as people bring their tech and expectations from home to the office,” says Kulp. “For the consumer space, I watch the gaming industry, as they are leaders in new practices and tech. Specifically, I knew augmented reality was taking off when Pokemon Go shook up the gaming world.”

“It's never clear what technologies are going to win out,” Merkens says. “But what is clear—just look at history—is that the current winning technology is always going to change. So you can stand your ground and ensure that you're going to lose or you can take a risk and make an educated guess which technology has the potential to win and hope you're right. Even if you're wrong, and I've been wrong innumerable times in the past, at least you gave yourself a shot.”

Sometimes, it might mean taking a flyer on a different industry. Katelyn Coghlan left a job at Nickelodeon to join In-It VR, which does virtual and augmented reality for brand marketing, and now is head of marketing at VR/AR company The Glimpse Group. It’s still storytelling, but different. “TV isn’t dying,” she says, “but it has definitely fallen out of favor with younger generations and been replaced with streaming services. If I wanted to continue to create traditional, linear stories, I could have gotten a job at Netflix or Hulu. But I wanted to tell stories in a different way, a way that has really never been explored.”

Stuck in the middle with who?

“Realistically, with technology, you can never build a career on one technology,” says Merckens. “You might luck out and have a company be stuck on a legacy system and you're the one guy who really knows how it works. But other than that, if you imagine you can pick a technology and only use that one thing for your entire career, you're out of your mind. You can't even make that last a decade at this point.”

And if you’re not up for it? Merckens suggests that maybe you might want to find another line of work entirely.

“You've got to love to learn to be effective in technology,” Merkens says. “If that doesn't get you juiced—constantly shifting gears and learning new stuff—then tech probably isn't the best field to be in for you. Which is fine! There are plenty of jobs out there that stay the same for 30, 40, 50 years. But technology isn't going to stand still. We're not going to blow a whistle and say, ‘Alright guys, no changes for the next 10 years!’ Stuff is changing exponentially faster, and you've got to do your best to keep up.”

Time to move on: Lessons for leaders

  • If you want a career that lasts, adopt a practice of learning a new technology every 18 months.
  • It’s time to move when conferences, books, and meetups about your field all turn stale.
  • Position yourself as a role expert, not a technology expert. Tech changes; roles not so much.

This article/content was written by the individual writer identified and does not necessarily reflect the view of Hewlett Packard Enterprise Company.