Mistakes I Made at Work

you’ve built a life others admire – degrees earned, barriers broken, respect carved from spaces that once questioned your right to belong. but here’s the quiet truth no one mentions: stability can start to feel like stagnation. those hard-won titles and safe roles? they don’t always leave room for the work that makes your pulse quicken, the kind that feels less like obligation and more like oxygen.

this chapter distills insights from 13 standout stories – drawn from the original collection of 25 – in which women turned career turbulence into breakthroughs. you’ll hear how they navigated doubt, redefined success, and mined clarity from chaos. their journeys span politics, tech, and the arts, offering raw strategies for trusting your instincts when external noise demands conformity. what you take away isn’t a flawless roadmap, but proof that reinvention begins when you stop chasing scripts and start writing your own.

women frequently face unspoken expectations to choose stable career paths – climbing traditional ladders, collecting impressive titles, holding tightly to hard-won security. this proves especially true for those who’ve overcome barriers in male-dominated industries or elite spaces. research indicates women tend to stay in unsatisfying roles longer than men, wary of perceptions that changing course signals unreliability. yet staying put isn’t always the wisest choice. bold moves toward meaningful work often mean leaving comfort zones behind.

consider rachel simmons’ story. simmons, now a best-selling author and leadership development specialist known for her work on girls’ social development, graduated from vassar college, a prestigious liberal arts institution, and thrived in new york’s political scene – city hall roles, senate campaigns, a rhodes scholarship. by outward measures, she’d mastered society’s playbook for success. but in oxford’s storied halls, surrounded by peers strategizing their next career chess moves, she felt hollow. the achievements meant little without personal resonance. though leaving such a prized opportunity meant risking judgment from others – particularly for a woman expected to prove her dedication – she chose departure over dissonance.

returning home brought challenges: confused parents, quiet doubts, the sting of stepping off a prestigious track. yet this space allowed reflection. childhood memories of playground exclusion resurfaced, sparking curiosity about relational aggression among girls. conversations with an editor focused on youth psychology led to unexpected clarity. her resulting book resonated deeply, creating opportunities aligned with purpose rather than external validation.

another example comes from corinna lathan’s pivot. lathan, a trailblazing biomedical engineer and entrepreneur, secured a rare faculty position in engineering before noticing troubling patterns. colleagues faced disproportionate demands – endless committees alongside research quotas – making career shifts feel perilous. but seeing her robotics work confined to labs troubled her. families needing adaptive technologies deserved real-world solutions. when a startup hub opened nearby, she traded academic stability for entrepreneurial unknowns.

early hurdles tested this choice. a promising therapy robot exceeded production budgets despite grant support. instead of retreating, lathan’s team adapted. their revised product succeeded, aiding children globally. she attributes perseverance to stem training – viewing setbacks as data points, not defeats. now her journey inspires others contemplating unconventional paths.

these accounts share a common thread: meaningful impact rarely follows rigid scripts. for women conditioned to avoid missteps, releasing the need for perfect linear progress can spark unexpected growth. security matters, but so does alignment between daily efforts and deeper values. whether through writing, innovation, or other channels, fulfillment often lies beyond the safety of checkboxes and gold stars.

by prioritizing curiosity over convention, both simmons and lathan discovered work that transcended superficial measures of achievement. their paths remind us that growth sometimes demands releasing the rungs we’ve clung to, trusting our capacity to reach for new ones.

the most challenging struggles frequently center on maintaining your identity within systems built on conformity. schools, galleries, and similar spaces often prioritize fitting into predefined roles over honoring individual values. what happens when your core beliefs collide with what’s expected? how do you stay true to yourself when everything around you resists that truth?

ileana jiménez, an educator and advocate for inclusive curricula whose work centers marginalized voices, confronted this reality while teaching at a private school. working in an environment where most students and faculty didn’t share her background, she noticed how classic literature curricula failed to resonate. many young people felt unseen, mirroring her own childhood disconnect before finding authors who spoke to her identity. introducing works by diverse writers became more than a curriculum adjustment – it questioned whose voices deserved space in education. 

resistance arrived quickly. during a tense meeting, her supervisor presented a detailed critique of her methods. surrounded by polished classrooms and sprawling lawns, she struggled to maintain composure while absorbing feedback that felt less about pedagogy and more about preserving tradition.

jiménez didn’t abandon her mission. she started integrating overlooked texts quietly, fostering classrooms where students could explore unfamiliar narratives. collaboration with the theater department opened doors to include playwrights from varied backgrounds. these incremental shifts highlighted a truth: transforming rigid systems demands persistence, creative collaboration, and knowing when to seek environments that better align with your vision.

artists face parallel challenges. take kim gordon, whose boundary-breaking work in experimental music and visual arts would cement her legacy as a cultural icon. early in her career, commercial galleries prioritized polished, sellable styles, clashing with her desire for raw, unfiltered expression. a shift occurred when she connected with new york’s experimental music scene. here, dissonance and minimalism replaced commercial appeal, offering freedom from rigid artistic rules. without formal training, she embraced this space, channeling authenticity over technical perfection.

even within alternative music, expectations lingered. female performers often adopted exaggerated personas – mystical, rebellious, or hyper-theatrical. gordon chose stillness instead. her presence onstage felt grounded, rejecting performance tropes to let genuine energy shape each show. years later, this philosophy guided her return to visual art. she avoided developing a trademark “style,” opting instead for pieces that felt spontaneous, even unfinished, resisting easy categorization.

stories like these share a common thread: staying true to yourself often means reshaping systems rather than accepting their limits. for jiménez, it involved gradual shifts through education. for gordon, it meant rejecting commercial art norms entirely. both paths required balancing conviction with adaptability – knowing when to push boundaries from within and when to build something new.

the impact extends beyond personal integrity. by creating spaces where authenticity thrives, others gain permission to do the same. students exposed to inclusive curricula discover new ways to see themselves. audiences encountering unpolished art find beauty in imperfection. lasting change begins when individuals choose to honor their truth, creating ripples that let others do the same.

for women in professional spaces, requesting support or opportunities frequently presents unique challenges. data indicates women tend to negotiate salaries less often, hesitate to seek advancement, or avoid requesting assistance compared to male peers. this pattern connects to workplace perceptions: women who assert themselves risk being labeled negatively, whereas similar behavior from men typically reinforces leadership impressions. overcoming this dynamic requires skill and persistence, creating pathways for personal growth and broader organizational change.

early in her medical training, danielle ofri confronted this reality. as a second-year resident surrounded by male colleagues, she faced her first critical decision with a diabetic patient. a nurse suggested administering long-acting insulin before stopping an iv drip. ofri hesitated. she wasn’t entirely sure of the best course of action but was eager to assert her authority in an environment skeptical of women’s expertise. she dismissed the advice, pushing aside the brief instinct to ask why it was necessary. after all, she had spent an entire day carefully managing the patient’s sugar levels and believed adding long-acting insulin would be unnecessary, even risky. the nurse raised an eyebrow but didn’t press further.

 two hours later, the patient vomited, his speech slurring dangerously. a senior resident intervened, shocked she hadn’t given the insulin. standing in the er, ofri froze –  when she had hesitated, she could have simply asked why the insulin was necessary. her refusal to do so nearly caused disaster.

the patient stabilized, but ofri grappled with guilt for weeks. she recognized her fear of seeming unprepared had clouded her judgment. this shifted her approach to medicine. later, mentoring new residents, she prioritized spaces where questions felt safe, especially for women facing similar pressures.

years earlier, joanna barsh encountered parallel struggles. starting in consulting after studying arts, she was assigned to analyze advertising data manually. alone in a client’s basement, she copied numbers onto massive paper sheets. exhausted and frustrated, she devised a shortcut but lacked confidence in her math. she quietly altered figures to align with expectations. 

when colleagues couldn’t replicate her results, barsh confessed her actions to her recruiter. instead of reprimanding her, he acknowledged the unreasonable workload she’d faced. this taught her that transparency about limitations can drive systemic improvements, particularly for women in male-dominated fields.

these accounts highlight a shared truth: seeking support isn’t weakness. progress often hinges on collaborative effort and admitting uncertainties. for women, developing this skill can reshape career trajectories and workplace norms, proving that growth emerges not from solitary effort but collective courage.

women in professional environments frequently confront dilemmas around refusal. setting limits on excessive demands, rejecting diluted expectations, or pursuing unorthodox career routes involves balancing personal priorities with external pressures. three narratives demonstrate how strategic refusal can redefine trajectories and values.

anna holmes, the visionary founder of jezebel, a platform that revolutionized feminist media, co-founded her pioneering website at a time when women’s perspectives were sidelined in digital spaces. in its formative years, the site’s momentum seemed to hinge on ceaseless output: publishing articles every ten minutes, interacting with readers hourly, and addressing comments well past midnight. the platform’s rapid ascent exceeded projections, but the grind took a toll. holmes developed chronic migraines. friendships withered. sleep became sporadic. years after departing the project, she still wrestled with the urge to check metrics and respond to every online critique.

resisting this cycle proved challenging because the work felt inseparable from her identity. the platform wasn’t just a job – it represented a cultural shift. eventually, holmes grasped that her self-sacrifice perpetuated a toxic standard for peers in the industry. stepping back allowed her to advocate for balance, showing that effective leadership doesn’t require self-destruction.

luma mufleh, a social entrepreneur whose school for refugee children became a model for trauma-informed education, confronted refusal through a lens of equity. one student, duke, stood out for his soccer talent and harrowing background. having lost his parents in war-torn liberia, he evoked mufleh’s empathy. she made exceptions: waking him for school, overlooking missed practices, supplying meals. but when another student challenged this disparity – asking why duke received leniency – mufleh faced a reckoning. her compassion, while well-intentioned, eroded the program’s foundational fairness.

applying uniform rules led to duke’s departure. the outcome weighed heavily on mufleh, who questioned whether she’d failed him. yet this decision reinforced the school’s ethos. students began trusting that rules applied equally, strengthening the community. upholding standards, even painfully, preserved the institution’s mission.

ruth reichl, whose career as a food critic and writer would redefine culinary storytelling, faced her pivotal refusal early on. colleagues and family framed her corporate banking role as prudent – a chance for stability in an uncertain economy. but the office’s rigid structure clashed with reichl’s creative instincts. walking away from predictability allowed her to explore food writing, a field she’d never considered professionally. this leap led to influential roles at major publications, where she reshaped how audiences engage with culinary culture.

these accounts share a central theme: refusal as preservation. for holmes, it safeguarded health and reshaped leadership norms. for mufleh, it maintained institutional integrity. for reichl, it protected creative potential. each woman’s choice carried risks – alienation, guilt, financial uncertainty – but also clarified what deserved protection.

the act of refusal often forces a confrontation with identity. who are we when we stop accommodating others’ expectations? what survives when we shed roles that no longer fit? these stories suggest that boundaries aren’t barriers – they’re the architecture of purposeful work.

setbacks often feel like final chapters. yet for many, these moments spark new beginnings. let’s look at three stories from women whose lives show how perceived failures can fuel growth when approached with intention.

judith warner, a journalist whose critiques of modern motherhood sparked national dialogue, built a career shaping public conversation through her new york times column. when it ended abruptly, the loss left her unmoored. days blurred into weeks spent glued to screens, tracking discussions she no longer joined. her daughter’s blunt observation – “this has gone on long enough” – became a catalyst. warner reconnected with friends, resumed daily routines, and channeled her energy into a book on children’s mental health. though sales fell short of expectations, the work resonated deeply with parents and professionals. requests for talks poured in. awards followed. what began as professional collapse evolved into work with impact far beyond personal recognition.

another story comes from ruth ozeki, a novelist whose award-winning work bridges fiction and spiritual inquiry. early television work left ethical bruises – particularly a cooking show funded by meat industry groups. years later, these regrets fueled her fiction. instead of burying discomfort, she gave it narrative form. her debut novel reimagined those career compromises through fictional characters, letting her explore roads not taken. the book’s acclaim launched her literary path, proving that past missteps hold creative potential when examined with honesty.

psychologist carol dweck, renowned for her research on growth mindset, uncovered parallel truths. watching children tackle puzzles, she noticed two distinct reactions. some withdrew from challenges, fearing mistakes. others leaned in with visible excitement. this split led dweck to identify two core attitudes toward ability. one views skills as fixed traits needing protection. the other treats them as muscles strengthened through effort. her own journey mirrored this discovery – early perfectionism gave way to embracing challenges, including repeated journal rejections that pushed her research toward greater clarity.

common threads emerge across these experiences. recovery often starts with small, deliberate steps – reengaging with community, examining past choices, reframing challenges as skill-building opportunities. warner’s return to human connection, ozeki’s creative excavation of regrets, and dweck’s shift from avoiding errors to studying them all demonstrate resilience as practice rather than destiny.

the takeaway? what looks like failure often contains unrecognized potential. by approaching setbacks with curiosity rather than judgment, we gain tools to reshape their meaning. whether through creative reinvention, community support, or shifts in perspective, ordinary moments of struggle hold extraordinary possibilities for those willing to look deeper.

in this chapter to mistakes i made at work by jessica bacal, you’ve learned that building a life of purpose rarely follows a straight line – it thrives in the curves.

women across industries, from politics to robotics, prove that meaningful work begins when you listen to the quiet voice urging you toward authenticity. their stories aren’t about grand gestures, but daily acts of trust: leaving roles that drain joy, challenging systems that demand conformity, and embracing uncertainty as creative fuel. the thread tying them together? courage isn’t the absence of fear – it’s refusing to let fear write your story. what you carry forward isn’t a blueprint, but permission to edit the rules until they fit the life you’re here to live.

okay, that’s it for this chapter. we hope you enjoyed it. if you can, please take the time to leave us a rating – we always appreciate your feedback. see you in the next chapter.