The offer is signed. Now what?
Career guidance for technologists tends to stop at the offer letter. There is no shortage of interview prep and technical training, but once you're in the role, resources on navigating the industry long-term are scarce. That gap has real consequences: a 2022 study from TalentLMS and Workable found that 72% of IT workers were considering leaving their jobs, with 41% citing limited career progression. Three-quarters said their organizations focus more on recruiting new talent than on developing existing staff.
Still, tech remains a uniquely rewarding field. Many roles offer remote work and flexible schedules, and the opportunity to build tools that reach millions of people is rare in other industries. Structural problems like stagnant career ladders require organizational change, but individual strategies—for growth, mentorship, and preventing burnout—can make the difference between staying and stagnating.
GitHub's ReadME Project senior editor Klint Finley spoke with three technologists about why they've stayed, how they've advanced, and what they'd do differently: Nick DeJesus, CTO of Black Tech Pipeline and maintainer of the use-shopping-cart library; Diana Liang, a technical writer and former software engineer and nurse; and Justin E. Samuels, founder of RenderATL and senior software engineer at Mailchimp.
Why stay?
The reasons for remaining in tech range from mission-driven to practical. DeJesus, who works with Resilient Coders to bring BIPOC individuals into the industry, says community keeps him motivated. "I love being able to take my ideas and turn them into reality," he adds. "I love being able to use my coding skills to provide value to people through my projects."
For Liang, the shift was dramatic and financial. "I made more money as an entry-level software engineer than I did in my previous career as a nurse," she says. "Tech is stressful, but it's not the sort of mental and physical stress I experienced in healthcare." She also values the breadth of roles available. "I made the transition from engineering to technical writing, which is a better fit for me. So if you're feeling like leaving the industry, maybe you just need to change the type of work you do."
Samuels sees each workday as a fresh puzzle. "It's like coming to work every day and there's a Rubik's Cube that you have to solve by the end of the day. Then, when you're done, someone switches up the cube so the solution will be different tomorrow." He cautions against chasing money alone: "If you're only chasing money you won't be happy in this line of work."
Milestones: promotion, pivoting, and side projects
Career advancement rarely follows a single formula, but the panelists' paths share a common thread: they sought opportunities rather than waiting for them. Samuels made senior engineer within his self-imposed three-to-four-year window by identifying organizational gaps and asking leadership to let him work on them. "That showed them that I was interested in more than a paycheck," he says. He also "under-promised and over-delivered," and was not afraid to ask for the next opportunity.
DeJesus built skills outside of work to move from IT support into engineering. He created an app for studying the fighting game Tekken that attracted 30,000 users, a success that helped him land an engineering role. But promotion within that company stalled after an acquisition. "Most of my career advancement—and this is true for many people in tech—came from changing companies rather than moving up within a company," he says. Side projects like use-shopping-cart have been his primary vehicle for learning and showcasing skills beyond his daily work.
Liang's milestone was a strategic pivot. After a year as a developer, she felt stuck: "I wasn't as comfortable coding as I wanted to be, I wasn't advancing my skills fast enough." Research revealed options like project management, business analysis, scrum mastery, and technical writing. She chose the latter, partly because she had always enjoyed the writing components of development more than coding itself. She reached out to several engineers who had made the same transition before committing.
Planning the next stage
None of the three follow strict five-year plans. Liang's horizon is modest and short: "A year ago I couldn't have imagined that I would be a technical writer today. I don't have a plan for the next five years, but I would like to continue as a technical writer."
DeJesus thinks in larger arcs. His goal is to build something self-sustaining, "whether that's by being acquired or by me passing the torch to another maintainer," and beyond that, to focus on problems he cares about without financial worry.
Samuels once swore by specific timelines, but has abandoned them. "Giving yourself arbitrary deadlines is a good way to set yourself up for disappointment and it can stop you from thinking bigger," he says. Now he strives to do work he is passionate about—organizing RenderATL among them—and lets goals clarify themselves.
The role of mentors
Mentorship looks different for each of them. Liang credits a mentor with being essential: "He gave me the push I needed." The encouragement to deepen her technical knowledge broadened her options, and she believes she might not have landed her technical writing job without it, since the interview still required demonstrating technical understanding.
Samuels prefers a network of unofficial mentors over a single formal relationship. "If you are intentional about listening, then you can use the gift of gab to export what you're learning from other people," he says. He approaches people at the career stage he wants to reach, follows them on social media, and looks for answers or pointers.
DeJesus says he has "suffered from a lack of mentors," which was challenging early in his career. He has compensated by cultivating friendships with people whose careers he respects. He interviewed at Netflix years ago and didn't get the job, but he still stays in touch with the hiring manager. His advice is distilled in a blog post titled "Don't seek mentors, seek friends."
Managing screen time
Liang laughs at the question. "I don't manage it," she admits. As an engineer she worried about total screen exposure—work coding, after-hours learning, plus gaming for leisure. The pivot to technical writing changed her relationship with work. "I'm more likely to stop working at 5 o'clock," she says, and remote work allows easy mid-day breaks. There is no pressure to appear busy.
Samuels aims for under six hours of average iPhone screen time daily but avoids much anxiety about it. "I think a lot of the worries about screen time are overblown. Our devices are how we connect with people," he says, noting that being available to answer questions is part of running his own company.
DeJesus, a lifelong gamer, says, "I am one with the screen," though he has built-in respites: months-long stretches away from development work in favor of writing, and deliberate shutdowns when burnout approaches. He identifies warning signs in physical reactions as much as mental ones. "When my heart rate increases thinking about the things that I don't want to do, that's a red flag." His remedy is triage: prioritize must-dos, drop optional commitments.
If not tech, then what?
None of them would leave tech lightly, but all have imagined alternatives. DeJesus would try video production, which he discovered while serving as a stand-in producer on a project. It is "overwhelming and stressful," and full of unpredictable moving parts, but "there's a real sense of accomplishment when you finish a project."
Liang would attempt a 180 that merges her backgrounds: "something to leverage my experience in both nursing and tech," though returning to the hospital floor would be a last resort. Samuels would first take a world tour, then work from McMurdo research station in Antarctica to get closer to a childhood goal of living on every continent. Eventually, he would return to what he considers the highest pursuit: "spending your time empowering people to reach their goals and be the best they can be."
