Upskilling in the Age of AI: Is the Old Bootcamp Playbook Still Working for Job Seekers?
In the summer of 2019, Bob McDonough enrolled in a full-stack web development coding bootcamp at the University of Pennsylvania. A former English major who switched to telecommunications for his degree, McDonough was working at a local bar at the time, sending out applications for roles he barely wanted. Most openings paid less than $50,000 a year—far too low for a 27-year-old building a life in Philadelphia. His degree, he says, simply “wasn’t cutting it” to open better career doors. “So I figured I’d add a certificate to bulk up my resume,” he explains.
What McDonough was doing is upskilling: the practice of learning new skills or refining existing ones to make yourself as competitive as possible in the job market. While working through the course, McDonough wasn’t convinced his investment of time and tuition would pay off. But by the end of the program, he’d built a polished professional portfolio, populated his GitHub profile, and added his new skills to LinkedIn. Within three months of graduating, he landed a full-time salaried role at a design studio. “Someone saw my profile and gave me a call pretty quickly,” he says.
Yet today, he doubts most job seekers could replicate that same outcome. In-demand skill sets are shifting faster than ever, and job hunters across the board report grim experiences in the current market. Back in the 2010s, “upskilling” often meant nothing more than signing up for a coding academy and crossing your fingers. But rapid, transformative shifts like the explosive rise of artificial intelligence have made the path to long-term career security far less clear.
“Ten years ago, completing a certificate might have been enough to land a role in high-demand fields,” says Nora Gardner, senior partner at McKinsey. The days of taking a short course at General Assembly and walking away with a lucrative coding job may be over.
In this report, we’ll cover:
Firsthand accounts from workers who’ve pursued upskilling, and whether it delivered new job opportunities
Creative, outside-the-box strategies to make yourself attractive to employers beyond just checking “learn Python” off your to-do list
What hiring managers actually prioritize when evaluating candidates, beyond the certifications listed on a LinkedIn profile
Uncertainty around AI’s impact on work is massive, and the job market remains unusually tough: In an August survey from the New York Federal Reserve, respondents reported an all-time low 44.9% chance of finding a new job if they lost their current role. On top of that, research from the McKinsey Global Institute estimates that roughly 10% of American workers will need to switch occupations entirely by 2030. A full 45% of employed workers looking for new roles cite “gaps in work experience, relevant skills, credentials, or education” as the single biggest barrier to landing a new position.
Today, the path to effective upskilling looks nothing like the route McDonough took just five years ago—but that doesn’t mean upskilling courses are completely obsolete. When paired with ongoing on-the-job practice and application, the effort to learn new skills signals to employers the soft skills that drive success in a fast-changing workforce: adaptability, a willingness to grow, and resilience. Multiple sources told Fast Company that employers now prioritize hands-on experience over narrow, pre-learned skill sets. Even so, building knowledge of the latest industry technology still delivers a major competitive edge.
Take Diana Rocha, a 37-year-old product manager based in London at predictive hiring firm Applied. A few months ago, she completed a DeepLearning AI course through Coursera. She then tested her new AI skills on Workera, a platform that lets learners validate their upskilled abilities, and scored in the 75th percentile. She added all of this experience to her LinkedIn in August, typically a slow month for professional outreach in London, and immediately saw her recruiter inquiries jump: from 1-2 per month to 2-3 per week, she says.
Rocha originally landed her current role at Applied through upskilling as well, via a master’s program and Coursera courses focused on behavioral economics. Even so, she’s not convinced the recent spike in recruiter interest came solely from her new AI skills. Her LinkedIn also highlights years of proven product management experience, and Rocha says recruiters who reached out were looking for that track record paired with her new AI abilities. It’s hard to isolate the impact of upskilling alone.
McKinsey’s Gardner, however, notes that it’s exactly this mix of existing professional experience and new upskilled abilities that makes candidates stand out to hiring teams. If you’ve worked in your field for decades, “certifications can signal commitment to learning,” she says. “But the differentiator is how they’re put into practice. Applying AI tools to improve workflow efficiency demonstrates adaptability in a way a credential alone cannot.”
Today, McDonough holds a new role as a web content coordinator at a law firm. But the experience he gained from the design role he landed through upskilling taught him to stay current on emerging technology. He regularly scouts YouTube and Reddit to “see what people are talking about,” he says. “If I click on something that has 300 comments, then I know I’m probably in the right spot.” Continuous, on-the-job learning, he found, is the key to useful upskilling.
Molly Johnson-Jones, CEO and co-founder of job search platform Flexa, says many organizations that sell upskilling courses often “sell a dream” that doesn’t match reality. Even so, she adds that workers looking to switch careers can start making that transition right within their current company. Johnson-Jones advises job changers to identify “what bits of your current role can help you move toward that new role.” For example, if you want to transition from marketing into tech, she suggests looking for opportunities to collaborate more with your company’s tech team, and build relationships with department leads.
That kind of transition relies on core interpersonal skills: empathy, social awareness, and emotional intelligence that make workers effective collaborators and enjoyable colleagues. These are widely cited as skills AI will never be able to replace. But can these skills actually be taught and upskilled?
Lisa Lie, founder of microlearning app Learna, says yes. Her company offers 10-minute-or-less lessons on skills like boosting confidence, creative problem-solving, and collaborating with any work style. Run by experts including psychologists and performance coaches, each short lesson opens with a common workplace problem—for example, diffusing a tense conflict with a coworker—then walks users through the most effective language and approaches to resolve the situation. Lie doesn’t call these “soft skills,” because “they’re not optional or easy,” she says. “If AI is taking care of repeatable tasks, the value of people skills just went up.”
For many working professionals, upskilling can feel like just another stressor added to the already heavy load of modern work. But Gen Z appears ready to adapt to this future. According to Flexa’s Work Index study, which analyzed more than 40,000 job posts and almost 30,000 job seekers, Gen Z workers are 68% more likely than older generations to prioritize personal development when searching for a new job.
Even millennials like McDonough and Rocha have adopted this continuous learning approach. Based on their own experiences landing new jobs directly as a result of upskilling, the strategy does work when done right. And as the youngest generation of workers prioritizes ongoing upskilling, it’s likely to become the new normal for modern careers.
“Tech moves so quickly,” McDonough says. Instead of just taking a one-off course like he did in 2019, he suggests job seekers looking to upskill today “stay up to date, read, [and] listen to podcasts on what people are actually doing.”
“The AI hype is going to calm down at some point,” says Rocha. “And yet? I wouldn’t like to be left out because I didn’t upskill on that front.”
McDonough agrees. AI might be today’s hottest trend, but company leaders are always tracking the latest trends, technologies, and industry shifts that change what skills they need to hire for. “You have to stay on top of it,” he says, “or else you’ll fall behind.”
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