Breaking into tech Under 4 months
From teaching to software engineering in four months
A former educator
Starting point. Eight years in education, including classroom teaching and a nonprofit, with no computer science background.
Career changer No CS degree Built a runway first
How she did it
What she did Tested the waters with online tutorials, textbooks, and weekend classes while still employed. Talked with engineer friends and coding school graduates, then made a financial plan. Quit and enrolled in a three-month, full-time bootcamp, paying about $20,000 upfront with private loans and savings. Built a portfolio and rewrote her résumé before applying. What was hard Twelve-hour days, six days a week, left no room for side income. Federal student loans weren't available, and rethinking her professional identity was harder than the coursework.
Where she landed A software engineering offer about three weeks after graduating.
The takeaway Plan your finances for the worst case. The emotional side of a career change is often harder than the practical side.
Read her story in full: The Muse
Go deeper: The Next Role Playbook Future-proofing your career in the age of AI
Breaking into tech About 12 months
From public health to software engineer in her late 30s, with a newborn
A public health analyst in her late 30s
Starting point. A research associate and program analyst in public health, with degrees in biology and nonprofit management.
Career changer Caregiving Over 35
How she did it
What she did Started a six-month, 35-hour-a-week online bootcamp when her daughter was four months old. Kept building small projects and practicing algorithms after graduating. Leaned on a bootcamp mentor who believed in her and paired with her beyond what was required. What was hard Sleep deprivation and constant interruptions during the bootcamp. The job search was the hardest part: rejections after coding tests and onsite interviews shook her confidence.
Where she landed Her first full-time software engineering role about six months after the bootcamp. She later became a senior software engineer at PayPal, according to her profile.
The takeaway A mentor who believes in you can carry you through the hardest stretch. Focus on fundamentals rather than chasing every new framework.
Read her story in full: DEV Community
Go deeper: The Next Role Playbook Future-proofing your career in the age of AI
Breaking into tech About 12 months
From events manager to software engineer while working full time
An events manager in her twenties
Starting point. An events manager with a hospitality degree, around 26, with almost no coding experience.
Career changer No CS degree
How she did it
What she did Researched bootcamps and attended a demo day before committing. Taught herself the basics on weekends for two months to meet the entry bar. Completed a pre-course while still working, then a 12-week bootcamp. Job hunted daily after graduating, sending about ten tailored applications instead of dozens of generic ones. What was hard She underestimated the entry requirements at first, and studying intensively alongside a full-time job was exhausting.
Where she landed A job offer about a month after graduating, into a software engineering pathway role at a large company.
The takeaway Treat the job search like a job, and send fewer, tailored applications.
Read her story in full: SheCanCode
Go deeper: The Next Role Playbook Future-proofing your career in the age of AI
Breaking into tech Part-time study, then 4 months to a full role
From nursing to product design
A nurse of ten years
Starting point. About ten years in nursing. She wanted a more balanced life and more time with her son.
Career changer No CS degree Caregiving
How she did it
What she did Tried free short courses to test whether design suited her. Studied UX design online and part-time, then specialized in visual design. Built a portfolio and applied widely, facing many rejections. Landed a summer internship at Mercedes-Benz.io. What was hard Her own self-doubt, and worrying that changing careers might be a mistake.
Where she landed A junior product designer role about four months after starting the internship, working remotely.
The takeaway The people skills from your previous career are an asset, not a gap. Test a field cheaply before you commit.
Read her story in full: CareerFoundry
Go deeper: The Next Role Playbook Future-proofing your career in the age of AI
Coming back Bootcamp, then 2 months to a job
Back to work after 20 years raising a family, as a software engineer
A mother returning after 20 years at home
Starting point. A sociology graduate who spent about 20 years raising her children with part-time jobs, and was told she lacked recent work experience.
Long career break Caregiving Career changer No CS degree
How she did it
What she did Enrolled in an online university coding bootcamp, using a women-in-tech scholarship that covered over half the tuition. Learned JavaScript, databases, and Git through group projects. Used career services for her résumé, interviews, and LinkedIn profile. What was hard The intensity of the bootcamp, imposter syndrome, and discovering that résumés and personal branding had changed since she last worked.
Where she landed An apprentice software engineer role at UCAS, then promotion to a junior role after earning the apprenticeship's top grade. She was also asked to help start a women-in-tech group.
The takeaway An online format let her keep family first. Age and a long gap needn't close the door.
Read her story in full: edX (published by the program provider)
Go deeper: Coming back strong: Returning from leave Coming back after a career gap
Coming back 3-year break, then a returnship
Back to software engineering after a three-year caregiving break
A software engineer returning after three years
Starting point. More than eight years as a software engineer at companies including JPMorgan Chase and American Express, before stepping away to care for her two young children.
Long career break Caregiving
How she did it
What she did Took refresher courses in algorithms, Java, and web services. Read other returners' stories and attended webinars that gave her the confidence to apply. Joined a returnship at VMware, working on open-source cloud tooling in a language that was new to her. Followed a 30-60-90 day ramp-up plan with a technical mentor twice a week. What was hard Starting from scratch in a new technical domain while balancing childcare.
Where she landed A full-time software engineering role at VMware after the returnship.
The takeaway A returnship gives you a structured ramp back. Talking to people who returned before you makes it feel possible.
Read her story in full: Path Forward
Go deeper: Coming back strong: Returning from leave Coming back after a career gap
Coming back 17-year break, then a returnship
Back to engineering after 17 years away
An engineer returning after 17 years
Starting point. An engineer who had been out of the workforce for about 17 years.
Long career break
How she did it
What she did Heard about a returnship program at Synopsys from a friend, which gave her the push to apply. Completed the pilot program while catching up on how much the technology had changed. What was hard Knowing how far the field had moved during her time away.
Where she landed Hired as a software engineer after the pilot.
The takeaway Even a very long gap can be bridged. Sometimes all it takes is one person telling you about the right door.
Read her story in full: Synopsys
Go deeper: Coming back strong: Returning from leave Coming back after a career gap
Moving up A career of steps, not a straight line
From a manager who blamed her to staff engineer
A staff engineer with a non-linear path
Starting point. She struggled in school, switched majors after failing physics, and found her way to computer engineering and then web development.
Non-linear path Leading without authority
How she did it
What she did Was promoted to principal engineer at a multinational, but struggled to get cross-team cooperation, and her manager blamed her instead of helping. Nearly left development; took an architecture course and taught high school computer science instead. Joined a new company as a staff engineer and became the go-to person for technical questions. Built influence by teaching teammates, joining cross-team working groups, and taking communication and negotiation classes. What was hard Earning credibility without formal authority. Her first major staff project took nearly a year to resolve.
Where she landed A staff engineer role where her influence comes from shared success.
The takeaway Teach others and let them own the work: it makes your expertise visible. One bad manager is not a verdict on your ability.
Read her story in full: Girl Geek X (talk transcript)
Go deeper: The Raise and Promotion Playbook From senior contributor to leader You're promoted! Now what?
Moving up Several promotions across companies
Security engineer to staff level, often as the only woman on the team
A cloud security engineer
Starting point. A security engineer who chose smaller companies early on to become well-rounded, then became a cloud security expert at Hulu.
Only woman in the room Leading without authority
How she did it
What she did Led a company-wide secrets management project, coordinating 25 partner teams through full adoption. Built metrics so security could show its impact to senior leaders. Spoke at conferences, gave internal training, wrote documentation, and mentored four colleagues. Her manager and mentor encouraged her toward the staff path. What was hard Being remote and often the only woman on her team, traveling to headquarters regularly, and the weight of high-impact decisions.
Where she landed Security architect, then staff cloud security engineer, then a staff engineering program manager role at Shopify.
The takeaway Scope of impact defines staff-level work. Negotiate hard, and leave managers who aren't kind.
Read her story in full: StaffEng Security stories (tl;dr sec)
Go deeper: The Raise and Promotion Playbook From senior contributor to leader You're promoted! Now what?
Moving up 6 months to the raise
Her first negotiation: a no that became a yes
A first-time negotiator in her twenties
Starting point. A first-time negotiator in her twenties, moving to a new division in her company and wanting a raise for the new role.
Internal move Negotiation
How she did it
What she did Researched salary ranges and rehearsed with a trusted friend. Opened with enthusiasm for the role, then named a number above her target. When the leader said the move was lateral and she was unproven, she agreed to a deal: hit the mark in six months and get the raise. What was hard Nerves, and the dip in confidence when the first answer was no.
Where she landed The increase she asked for, six months later.
The takeaway A no can mean not yet. Creative, win-win terms can turn it into a yes.
Read her story in full: Her coaching blog
Go deeper: The Raise and Promotion Playbook From senior contributor to leader You're promoted! Now what?
Moving up 7 weeks, after 3 years of wanting it
From support engineer to product manager in seven weeks
A support engineer at a large tech company
Starting point. A support engineer at Microsoft who had wanted to move into product management for about three years.
Internal move Career changer
How she did it
What she did Set herself a two-month deadline to make the switch. Completed product management coursework and prepared for each interview question type. Contacted hiring managers directly and treated networking calls as practice interviews. Tailored her résumé to show how support work built product skills, then negotiated the offer. What was hard Studying at 5 a.m. around a full schedule, framing her experience for behavioral interviews, and no mentor, so she mentored herself.
Where she landed A product manager role at Microsoft, with an offer in seven weeks.
The takeaway A deadline turns a someday goal into action.
Read her story in full: Medium
Go deeper: The Raise and Promotion Playbook From senior contributor to leader You're promoted! Now what?
Moving up Reflections after year one
Engineer to first-time engineering manager
A software engineer at an education tech company
Starting point. A software engineer who was offered the chance to manage her own team during a period of fast growth.
Internal move First-time manager
How she did it
What she did Accepted, knowing she could return to engineering if it didn't fit. Asked for specific feedback and gave continuous feedback so reviews held no surprises. Set up regular meetings with partner teams and raised timeline risks early. Asked her team for ideas before offering her own, and delegated work as growth opportunities. What was hard Measuring success as a manager, letting go of being the technical expert, and admitting uncertainty.
Where she landed A year into managing, with practices she now relies on.
The takeaway Saying "I don't know" and inviting input leads to better solutions and a stronger team.
Read her story in full: Clever Engineering Blog
Go deeper: The Raise and Promotion Playbook From senior contributor to leader You're promoted! Now what?
Navigating setbacks Months of rejections, then days
Laid off, stuck in automated screens, then a video that broke through
A marketing manager in Madrid
Starting point. A marketing manager at a fintech company in Madrid, laid off in October.
Laid off
How she did it
What she did Applied the standard way for months and rarely got past automated screening. Made a short LinkedIn video showing her skills instead of describing them. When a London employer wanted her to relocate, she declined and they agreed to remote work. What was hard Dozens of automated rejections in a cooling job market.
Where she landed Hundreds of employers reached out after the video spread, including a former coworker who asked to interview her within minutes.
The takeaway Show your work, don't just describe it. And be clear about the terms you want.
Read her story in full: Fortune
Go deeper: Laid off? Your first two weeks Put on a PIP? Your first week
Navigating setbacks More than two years and counting
Laid off from a big tech company, and still finding her way
A site reliability engineer
Starting point. A site reliability engineer whose entire team was laid off in November 2023.
Laid off Still in progress
How she did it
What she did Took time to reassess her goals, then searched for midlevel remote roles. Interviewed several times without an offer, then shifted toward smaller companies. After more than a year, paused the search, started a web development business, and resold antiques for income. What was hard Midlevel roles were scarce, interviews sometimes felt like trivia, and her savings ran down as the search stretched on.
Where she landed Still in progress. She hopes to return to tech, focusing on smaller companies.
The takeaway Build a bigger emergency fund than you think you need, and plan for a longer search. Smaller companies were more responsive.
Read her story in full: Business Insider, via Yahoo
Go deeper: Laid off? Your first two weeks Put on a PIP? Your first week
Going independent Years of side work, then the leap
Corporate to full-time freelancer, with two years of savings
A writer who built a freelance business on the side
Starting point. A full-time employee with a journalism background who freelanced on the side.
Built a runway first Side hustle first
How she did it
What she did Saved all her freelance income, about $1,500 a month at its peak, until she had roughly two years of take-home pay saved. Kept saving for retirement with accounts suited to self-employment. When she went full time, told past clients, former colleagues, and her LinkedIn and email contacts. What was hard Her first three months earned less than her salary, income was inconsistent, and much of the work, like pitching, went unpaid.
Where she landed About three and a half years later, most of her work came from existing clients and referrals.
The takeaway Start on the side, build a big cushion, and tell everyone you know when you make the move.
Read her story in full: Northwestern Mutual
Go deeper: Build your freedom fund The Courage Playbook
Going independent A few months of searching while employed
Signed her first clients before quitting, with no audience
A UK copywriter
Starting point. A full-time employee who couldn't openly advertise her freelance work without risking her job.
No audience Side hustle first
How she did it
What she did Set up a website, a portfolio from her day-job work, and a professional email address first. Landed her first client by answering a request a creator posted on Instagram. Searched LinkedIn every day for freelance copywriter posts from the last 24 hours, which brought two more clients. Subscribed to newsletters that send freelance gigs. What was hard Finding clients while employed and unable to say so publicly.
Where she landed About £800 from her first client and over £6,000 from the next two, then she handed in her notice.
The takeaway Look professional before you look for clients, and make searching a small daily habit.
Read her story in full: Substack
Go deeper: Build your freedom fund The Courage Playbook
Going independent Early days of a new business
Corporate to career coach: how she found her first five clients
A corporate professional turned career coach
Starting point. A corporate professional who became a career coach after scrapping her first business attempt.
No audience
How she did it
What she did One client came from a flyer in a coffee shop she frequented. One came from a helpful comment she left on someone else's blog. One came from an email to her professional network of about 40 women. Two were former colleagues from her corporate job. What was hard Financial strain early on, and the fear of talking to potential clients.
Where she landed Her first five clients, from simple, low-tech outreach.
The takeaway Clients can't find you if you keep your business a secret. Tell people what you do.
Read her story in full: Her blog
Go deeper: Build your freedom fund The Courage Playbook
Going independent Three years of building
From brand director at a global company to a company of one
A former brand director at a global company
Starting point. A brand director at Procter & Gamble who wanted more learning, more variety, and more time with her two children.
Caregiving
How she did it
What she did Started a consulting practice helping consumer brands sell more effectively to women. Joined a coaching program and learned from consultants who had done it before. Invested in content and video, then hired help and subcontracted partners. Set a protected weekly block for business development. What was hard Getting comfortable with discomfort after going from a company of about 100,000 people to one, and doing tasks she didn't enjoy.
Where she landed A practice with partners, repeat clients, and fewer nights and weekends.
The takeaway Delegate what drains you: hiring help buys back time for the work only you can do.
Read her story in full: Consulting Success podcast
Go deeper: Build your freedom fund The Courage Playbook
Going independent About 28 months from first code to $80K a year
From big tech engineer and burnout to a profitable company of one
A software engineer turned founder
Starting point. A software engineer at Twitter who co-founded a startup, burned out, left, and freelanced.
No audience
How she did it
What she did Built a budgeting tool to solve her own problem with multiple currencies. Spent about two months on a first version and six more polishing it with beta users. Launched on Hacker News, which brought about 100 early users. Grew through user interviews, case studies, and search, and hired contractors for support and marketing. What was hard She never had a solid marketing plan and calls her early traction partly luck.
Where she landed About 1,000 paying users and roughly $80,000 in annual recurring revenue, about 20 months after launch.
The takeaway Solve a problem you have yourself, and own a niche.
Read her story in full: Indie Hackers AMA
Go deeper: Build your freedom fund The Courage Playbook
Going independent Just beginning
Left a six-figure role at 39 with no plan B, and is figuring it out
A media and technology executive, 39
Starting point. Eighteen years in media, advertising, and technology, most recently in a senior role that wasn't a fit.
Built a runway first Over 35 Still in progress
How she did it
What she did After a personal loss made her rethink how she spent her time, she resigned without another job lined up. Relied on nearly two decades of disciplined saving and investing as a cushion. Began exploring freelance, consulting, and part-time work, and shared her journey publicly. What was hard Her identity had become tied to her title and salary, and some days she doubts her decision.
Where she landed Still in progress. Her online community grew quickly after she shared her story.
The takeaway A financial runway, ideally about six months of expenses, is what gives you choices.
Read her story in full: Newsweek
Go deeper: Build your freedom fund The Courage Playbook
No stories match every filter yet. Try removing one, or clear all filters .
