Programming jobs for losers

You’ll need the right attitude and the right hard and soft skills to feel like a winner in your software development career.

Programming jobs for losers
Adam Birkett (CC0)

Computer programming is, you’ve no doubt heard, the ticket to a great career. It’s become a political cliché that workers in dying industries need to “learn to code.” Doing so promises both professional fulfillment and lucrative compensation—or so goes the conventional wisdom. Listen to anyone, and they’ll tell you programmers are the winners in today’s job market.

But the reality is often different. Alex Yelenevych is co-founder and CMO of CodeGym, an online Java course, and many of his students are trying to gain the skills they need to leave their current programming jobs. They’re bogged down in endless unit testing and legacy code support. They feel like a worker on an assembly line. They’re tasked with duties like developing code for SMS spam distribution, a specialty Yelenevych describes as both “not so easy” and “extremely unpleasant.”

In short, they feel like losers. And the nitty-gritty truth is that computer programming is full of jobs that will make you feel that way. We spoke to a number of tech pros and career experts to answer some key questions about jobs for losers: how can you identify them, avoid them, or escape from them?

Learn to spot a loser

Probably the best definition of a job for losers is that it makes the person holding the job feel like a loser. But that’s subjective, and means the same job might be one person’s dream gig and another’s crushing burden.

“Sometimes, people wind up in programming jobs that don’t fit them personally,” says Sanket Shah, CEO of InVideo. “Troubleshooting and reworking poorly written code with bad documentation might be a nightmare for one candidate, but another programmer might love the feeling of solving a puzzle and deciphering hidden secrets. A job with lots of bulk coding—the kind of stuff that’s often referred to as ‘code monkey’ work—might be tedious and boring to one person, but another programmer might love being able to get lost in one specific task for hours at a time.”

Still, there are red flags to look out for. One of the most important signs that a job will make you feel like a loser has to do with the status of tech within a company. “Some tech departments are treated solely as a cost center and not a strategic asset,” says Ryan Maxwell, CTO at FirstRate Data. “In such companies, I would always recommend that the developer should leave, as the quality of the tech is never the focus; this leads to the developer being asked only to keep the system running at a minimum of cost, which is a mind-numbing job.”

In fact, when assessing a job and its fitness for you, you should evaluate the big picture of what you’ll be doing: not just the programming aspects, but what value you’re providing within the company, and what the company itself produces.

“The attitude is to remember that you are creating and upholding a product that positively affects so many lives,” says Tom Winter, lead tech recruitment advisor and co-founder of DevSkiller. “If one should feel stuck in their programming job, one should ask themselves, what do I really want to make? Being interested in the product that you will put together should be the first step to make you feel like you are winning in life.”

But if you do fall into a job you come to dislike, there is some bad news: These jobs can be self-perpetuating, leaving you feeling like Bill Murray in Groundhog Day.

”Programmers often wind up pigeonholed into jobs that are similar to what they’ve done before, so if you hate the work you’ve been doing, you’re probably going to be offered similar work in the future,” says InVideo’s Shah. “But the good news is most of your computer programming skills are transferrable, and you can transition into something that’s better suited for your personality.”

That transition won’t just magically happen, though. You’ve got to take affirmative steps to recognize when you’re in that loser rut and find the job that will make you feel like a winner.

Escape from loserdom

Here’s the good news. Even if you feel stuck in a rut, know that the computer programming industry as a whole is in a constant skills crunch.

“If you are stuck in a job that you dislike and doesn’t seem to be going anywhere, always remember that there is a better job around the corner,” says DevSkiller’s Winter. “Especially in 2021, now that the floodgates for remote hiring have been opened and skilled candidates are available from all over the world.”

But just because a job that’s a better fit for you is out there doesn’t mean that it’ll come your way just because you want it. Many will require skills or experience that aren’t currently on your résumé. For some, that’s a big barrier that may make them discouraged. But you shouldn’t give up hope. The skills piece is in some ways fairly straightforward—if you want to work in an area that uses specific languages or technologies, you need to bone up and learn about that tech. That doesn’t mean you need to become a PhD level expert, but you should take advantage of online documentation or short-term bootcamp-type courses that you can work through in your spare time or at your own pace.

When it comes to experience, though, that can be harder. But here too you shouldn’t give up hope. Eva-Marie Costello is chief of staff at Springboard, which provides online courses in data science, machine learning, design, and analytics—but also helps clients shape their résumés beyond just adding those skills to their toolkit.

“We feel you really can frame any experience—even from a boring job where you may be working on static web pages or mundane code,” Costello says. “How you frame it is something that a lot of our career coaching focuses on: helping the student to set themselves up for success by putting their experience into perspective of why it might be valuable to an employer.”

“Every job is a learning experience,” says Sander Tamm, founder and CEO of E-Student. “You need to look at any opportunity through the prism of ‘What can I learn from this?’ Is it skills, processes, software? Even in a bad situation, consider how much you can learn from watching someone do everything wrong.”

Somewhat counterintuitively, a great way to advance your career might be to work for free. You may want to approach a nonprofit or community group that needs technical assistance and offer to help them so you can flex your new skills in the process, says Mark A. Herschberg, an instructor at MIT and author of The Career Toolkit: Essential Skills for Success That No One Taught You.

Telling a nonprofit, ‘Look, I can help build out some of the stuff for you,’ is a great way to build out certain skills,” Herschberg says. “You gain the experience, you’ve done this type of work, and it doesn’t matter really if you were paid or unpaid. If you earned it, you did it, and you’re ready to do it again.”

Skills beyond programming

You’re probably not terribly surprised by some of this job-seeking advice. It’s pretty obvious that if you’re stuck in a job you don’t want, you need to get the technical skills and experience that will get you the one that you do want.

But so-called “soft” skills, often discounted by those in technical fields, can help you shake off your loser job in a couple different ways. For one thing, they’re in demand from potential employers, just like technical skills are—especially for the sorts of dynamic and higher paying jobs those stuck in a rut crave.

“Frankly, to go from one programming language to another is not a huge shift,” says Herschberg. “But do you know how to work with other teams? To budget? To explain engineering challenges to marketing in a language they can understand, and then take marketing’s concerns to turn them back into technical options and opportunities and concerns for the team?”

One surprising opportunity to show off those kinds of skills is in the context of a technical job interview. Fahim ul Haq is CEO and co-founder of, which among other services offers extensive interview prep courses. ul Haq sees these kinds of interviews as leveling the playing field for candidates who may have acquired skills via unusual experience that doesn’t necessarily look as impressive on a résumé. He also thinks they offer a chance to show your interpersonal and other soft skills to the people you’ll be working with.

How so? ul Haq explains by citing examples of the questions interviewers will be asking themselves: “Does the candidate articulate their thought process well? Can they weigh different methods of solving a problem, and think through the trade-offs of each one? Do they communicate clearly? Do they ask the right questions?”

“In an actual job,” ul Haq continues, “you might have to think on your feet to resolve an issue that has caused an outage. It’s very similar to an interview setup. You have the product and code knowledge (background), and there is a new unknown problem (service outage), and time is critical (anxiety). Your performance in the interview is a good proxy for how you would react and how your problem-solving skills would kick in when there’s a critical issue.”

Here we see how soft interpersonal skills are both attractive to employers in and of themselves and important in navigating the social arena in which hiring takes place. After all, interviewers also want to know if your personality will work with your future coworkers. “Increasingly, as companies realize the importance of building strong, unique cultures, behavioral or cultural fit interviews are becoming more critical as well,” says ul Haq. “Is the candidate showing they are a cultural fit? Do they embody the company’s values?”

You’ll also want to flex those interpersonal skills in your everyday life, as you build up a network of professional contacts that will help you find a winning job—something that’s extra important if you feel a little behind the curve on your technical skills.

“Obviously, if you don’t have the hot technologies, you have to be more proactive, and that’s where networking comes in,” says Herschberg. “Understand how to build up a network and use that to find opportunity.”

And that network needs to go beyond just your fellow techies, Herschberg adds. “It’s important to have diversity within our network. Don’t just think about our engineers; think about meeting other people in different fields. If you know a bunch of accountants, they don’t know a lot of engineers. I know so many people have come to me and said, ‘My friend needs a tech guy.’” If you’re genuinely interested in what their company does, that tech guy could be you.

One way to build up your network is through formal mentorship programs. Costello explains that Springboard connects its clients with mentors that not only provide accountability as they improve their skills but will help them navigate potentially unfamiliar niches of the job market.

“A lot of them do guide you,” Costello says. “They’ll say, ‘You’ve never been a software engineer before and you come from a very different background. Is going for this job at Apple realistic? Would you be better looking at different types or building your experience by doing pro bono projects?’ They definitely reality check people.”

Stay a winner

One final note: Just because you’ve left that loser job behind, and you have a new gig that makes you feel like a champ, doesn’t mean you’re set for life. In a few years, you might start feeling pigeonholed and bored again. Or maybe new, less competent management will take over and the job will get less fun. Or what seemed like a steady high-paying gig was undercut by cheaper overseas labor.

The truth is that the techniques we’ve outlined here aren’t one-and-done. You’ll always need to be ready to look for that next winning job. Herschberg works with his MIT students to prepare them for the real world, but he also thinks that preparation and learning can’t stop in college.

“As a society, we need more regular learning,” Herschberg says. “In medicine and law there’s continuing education credits, for instance. We also need to recognize at certain points, you should be able to go back for a little more in-depth training for eight or six months—maybe you take a sabbatical from work when you go back to retrain. Maybe your domain knowledge needs improvement to deal with a newer engineering technology. Maybe you’ve got to learn some more managerial skills before you go out and be a manager.”

“There’s tremendous relief when one of our students gets a job offer,” says Costello. “It’s like, ‘This is the start of my new life! This is the next stage of my career!’ But something we’re big advocates for at our company is that people are going to have five to ten different careers now. Comfort with the learning process is what we really strive to equip our students with.” That comfort will help you stay away from loser jobs as you progress through your professional life.

Copyright © 2021 IDG Communications, Inc.