Intro
This is a fictional example of how the first generation of MentorGuilds might operate. You may want to read the book summary first to better understand the context before continuing.
In the early stages, MentorGuilds are likely to focus on simple, high-certainty opportunities — what might be called “low-hanging fruit.” These are individuals who already show promise: They are talented; disciplined; and may have already taken early steps toward a career, but remain blocked due to lack of guidance or difficult life circumstances.
Recruiting
Karla and Jane are senior software developers with decades of experience. Their talks are available online, and their blog posts are widely read. They have heard about the rise of MentorGuilds — an idea gaining traction — but notice that most existing ones are gender-neutral and miss the opportunity to focus on underrepresented groups.
Having long encouraged young women to explore software development, Karla and Jane decide to take that mission a step further by launching their own MentorGuild: "Girls Who Code MentorGuild."
They begin by offering a free coding workshop/recruiting session in a low-income neighborhood, specifically for young women. To qualify, attendees must first watch three of their one-hour online videos covering the basics. This small requirement helps filter for commitment while ensuring that all participants arrive with a shared foundation.
This simple initiative marks the beginning of their MentorGuild journey — targeting a group with untapped potential and high payoffs, both socially and economically.
Many attendees show up for their workshop, but it quickly becomes clear — through their questions and comments — that most have not completed the required pre-course videos. One young woman stands out: Bea. She asks thoughtful, relevant questions that reveal that she did the preparation and is eager to learn, even without prior experience in coding.
Bea is the older of two sisters. Her father left the family when she was young, and her mother has held the family together ever since, running a small food stall in the local market. The family lives in a cramped apartment, surviving on a modest income.
Now that Bea has finished high school, her mother is hoping she will join the food stall business and help it grow. Bea, however, is more interested in technology and software. She understands that the information technology (IT) industry offers higher earning potential and long-term career opportunities, but her family cannot afford university or specialized training.
Karla and Jane offer to take Bea on as their first official mentee. Bea is excited, but hesitant, as MentorGuilds are a new thing. She explains that she needs to talk with her mother before making a decision.
The next day, Bea returns with bad news: Her mother needs her help at the food stall immediately. She cannot afford to spend a long time without contributing income to the family.
Karla and Jane ask if they can speak directly with her mother at their home. A few days later, the four of them sit down together. Karla and Jane explain Bea’s potential. They believe that, with her curiosity, work ethic, and intelligence, she could land an entry-level developer job after as little as one year of focused study. But Bea’s mother insists that they do not have a year — she needs her daughter’s help now.
Karla asks how much income Bea would likely generate at the food stall in the coming year. The amount is modest — far less than a junior developer’s starting salary. Karla and Jane step aside and discuss whether their planned one-year Education program could be compressed. They decide that with an intensive focus, they can give Bea the minimum essentials in three months — just enough to help her secure her first coding job. The rest of her Education can be delivered later.
Bea is thrilled. Her mother remains cautious. She is skeptical of MentorGuilds and unsure that such a short period of Education can lead to real employment.
Jane addresses her concerns directly. Even in the worst-case scenario, she explains, Bea will gain valuable digital skills — skills that can be used in the family business, from creating a website to designing banners or managing inventory software. If Bea doesn’t get a job in the industry, and ends up working at the stall, she will owe nothing to the MentorGuild, as the core skills of working in a food stall do not largely use the skills listed in the MentorGuild contract.
Karla then outlines the proposed the terms: 3% of Bea’s income for 9,200 hours of work — roughly five yearsKarla then outlines the proposed the terms: 3% of Bea’s income for 9,200 hours of work — roughly five years, with an income floor as their given estimated return from working at the food stall, to provide her with some income security.
In return, the MentorGuild will pay for a few online courses covering the essentials of coding and provide daily 30-minute calls with Karla or Jane for the first three months. These sessions will include help with coursework, discussion of concepts, and ongoing mentoring — all the way through to her first job offer.
After Bea begins her job search, the MentorGuild will continue to provide support. She will gain access to a curated list of IT courses designed to deepen her technical skills. Karla and Jane will assign her targeted homework to build her skills and ensure that she is learning what the market demands. They will review her homework, give detailed feedback, and help her start a portfolio — an essential asset for job applications.
Bea’s mother is hesitant at first, but agrees to let her try the program for a few months. The risk is low, and the potential gain is high. Bea signs the MentorGuild contract and gets instant access to the first course. She is now officially a mentee — and she is thrilled.
First Mentee and First Job
By the end of her first day, during a scheduled video call with Jane, Bea reports that she spent the entire day immersed in study and has already started coding her own app. Jane congratulates her, probes her understanding of key concepts, corrects a few missteps, and shares additional examples and stories.
Before ending the call, Jane offers a critical reminder: “Do not neglect your health. Passion is powerful, but this is a marathon, not a sprint. Eat well, sleep well, move your body — and your brain will thank you.”
Over the following weeks, Bea works hard on learning programming, but also many other subjects.
She learns how to work with a mentor — how to use their time wisely, how to ask for feedback, when to take initiative, and how to stretch herself between sessions. Karla and Jane introduce her to real-world job positions and walk through their job descriptions line by line, explaining what each requirement means and what level of skill she will need to reach.
A few weeks before the three-month mark, they encourage Bea to start applying for jobs, even if she feels unprepared. It is not just about landing a role — it is about learning important skills such as interviewing, self-presentation, and handling rejection. Bea admits that she feels unqualified. Karla and Jane explain the concept of impostor syndrome, reassuring her that confidence grows through action.
Just before the three-month deadline, Bea receives a job offer from a small startup, with a staff consisting of just the founder and a few employees. The salary matches what she would have made working full-time at her mother’s food stall, but with far more growth potential. The founder even hints at future promotions as the company expands.
During the final interview, the founder asks if Bea is affiliated with a MentorGuild. As coached by her mentors, she says no. While this may seem ethically murky, it is fully supported by MentorGuild law, to protect mentees from employer skepticism regarding unconventional educational paths — a reality Karla and Jane prepared her for.
Bea shares the offer and job contract with her mentors for review. After discussions, they all agree that this is a strong first step. Bea accepts the position.
Bea begins her new job with enthusiasm — and quickly thrives. Both she and her mother are thrilled. Bea is contributing to the family finances while working in a field she is passionate about. She is paid to learn (experiential Education), grow, and explore a career with long-term potential.
She throws herself into the job, practicing technical skills, observing how IT companies function, and absorbing everything from data security to project management. She builds social capital with her colleagues, volunteers for extra tasks, and pays close attention to workflows and team dynamics.
She also works long hours — not out of obligation, but because she is learning and engaged. Most days, she checks in with her mentors to discuss what she is learning, explore new resources, and identify areas for improvement. They assign additional homework to strengthen her foundation and keep pushing her development forward.
Her manager notices her. Impressed with Bea’s initiative and reliability, he assigns her more responsibilities. As her value to the company grows, so does her confidence — and her mother’s. The decision to join a MentorGuild appears to be paying off. The income is steady, her employer is supportive, and her Education (both formal through courses provided by the MentorGuild and experiential from the job) continues.
With guidance from the MentorGuild, Bea regularly updates her online portfolio and public profile. As a result, headhunters begin to take notice. She starts receiving inquiries and job offers. For the first time, her family’s financial future feels not only stable, but hopeful.
After six months, however, a new pattern emerges. Bea is now spending more of her time on repetitive, low-growth tasks, often during unpaid overtime. Her manager assigns her these tasks because he trusts her — and because she delivers. But the learning curve is flattening.
Bea remains upbeat. She tells her mentors that she is still excited about the job. She feels valued, respected, and secure. Financially, she is doing better than she ever imagined at this point in her life.
But Karla and Jane see some early warning signs.
First, Bea’s unpaid overtime is being counted as part of her contractual work hours — without generating any corresponding income. This reduces the MentorGuild’s income and public profile, while offering limited benefits to Bea. Second, her experiential Education has begun to plateau. The daily challenges that once pushed her to grow have faded, replaced by routine and predictability. Her boss says that he is sorry, and promises to give her tasks more aligned with her talent, but nothing changes.
While Bea still feels satisfied and valued, the MentorGuild gently suggests that she consider aiming higher. Her current role may feel safe and familiar, but it no longer stretches her abilities or develops new skills. What was once a perfect fit may now be holding her back.
The MentorGuild’s role is not to pressure, but to guide. Their concern is not just about lost income — it is about potential left untapped. The question now is whether Bea will remain in her job or seek her next stage of growth.
Karla and Jane begin asking pointed, reflective questions during their weekly calls with Bea:
- Has the company shown any signs of growth?
- Has anyone discussed clear standards for promotion for her position?
- Have any of her colleagues been promoted?
- Are the extra hours temporary? Or is the company dependent on her because she tolerates work others avoid?
- How long, on average, do employees stay at the company?
Bea answers each question honestly — and the picture that emerges is not encouraging. The company appears stagnant. No one has mentioned promotions, let alone planned them. The team experiences high turnover, and the leadership often looks more anxious than inspired. Bea is working extra hours with little guidance or advancement.
Seeing the pattern, Karla gently recommends two steps:
- Ask her manager what specific skills and milestones are required for a promotion, so she can begin deliberately preparing — observing senior colleagues, developing targeted abilities, and building toward the next level.
- Cut back on the extra hours. If Bea wants to invest in her future, that time is better spent learning new knowledge and skills suggested by the MentorGuild and building her portfolio — not doing low-value work that others avoid.
Bea is surprised and defensive at first. She feels grateful for her job. It pays well, it came quickly, and it is a better job than anything her high school friends have found. She thinks Karla and Jane should be thrilled.
But as the conversation sinks in, Bea begins to see the underlying truths: No one has mentioned career paths or promotions. The leadership team seems disconnected. Her peers are not growing — they are leaving. And while she is respected, she is also being used.
Taking Karla’s advice, Bea approaches her boss and asks what is expected of her to earn a promotion. The response is vague and noncommittal. He also agrees to reduce her extra hours, but only partially — saying that she is "the best they have" and that the others are not ready to take on more responsibility.
With some free time reclaimed for Bea, the MentorGuild assigns her a new online course and complementary homework. They do not say it outright, but the intent is clear: They are preparing Bea for her next job move.
Over the next month, little changes. There is no upskilling of her coworkers, no shift in management’s attitude, and no clarity regarding career growth. In her weekly mentoring calls, Bea reflects out loud: Maybe this job is not as perfect as I thought. The seed of doubt was successfully planted by the MentorGuild — and it is now germinating.
Jane takes a deep breath during one of their weekly calls and shares her honest assessment: Bea’s current role is likely a dead end. It shows all the classic signs — including stagnation and vague promises. Some small companies grow into great companies. Others stay small forever because their leadership is disorganized, complacent, or simply incompetent. Unfortunately, it looks as if Bea is working for one of the latter.
Bea feels hurt. She had started to identify with the company — viewing her coworkers as a second family, admiring the founder’s scrappy beginnings, and daydreaming about one day becoming a director. Her hopes and identity were wrapped up in the company’s story.
Karla and Jane recognize this for what it is: the standard “company loyalty trap” — a kind of soft brainwashing many workers fall into, often without realizing it.
They gently remind Bea of a healthier mindset: Do not identify with your company. Identify with your career and family. Those are permanent. Your employer is not.
Still, Bea and her mother remain uneasy. Changing jobs so soon feels risky, even disloyal. Karla explains that this hesitancy reflects the swing of a psychological pendulum: Six months ago, they doubted Bea could even land a job in tech. Now, they have placed too much faith in this one job and employer. A strong career is built on a balanced mindset — faith in your future, and a healthy skepticism about your current situation.
But Karla and Jane know the risks of pushing too hard. If they force the issue, Bea may withdraw — not only from this conversation, but from their future guidance altogether. This is a well-known risk.
Pushed out of Her Comfort Zone
Fortunately, MentorGuilds have the tools for dealing with this exact situation. Karla suggests a classic move: Do not ask the mentee to quit. Just ask her to “start interviewing to see what’s out there.” The benefits are numerous:
- practicing interview skills,
- discovering which work skills are truly in demand,
- obtaining honest feedback (something her current company won’t give),
- building a broader professional network and social capital, and
- understanding her market value.
Bea is skeptical at first. Why interview when she has no intention of leaving?
Jane flips the perspective: “Companies do this to candidates all the time. They interview even when they are not hiring, just to see what’s out there and build their database of talent. Why should candidates not do the same?”
The worst-case scenario? She learns, builds confidence, and says “no” to offers. The best case? She finds a much better opportunity.
Encouraged, Bea applies to mid-level developer roles. To her surprise, she performs well in technical tests and interviews. The skills she gained through her job, MentorGuild courses, daily homework, and mentoring sessions have quietly prepared her — far more than she realized.
But she still does not land any job offers. Karla suggests recording her next online interview (with the interviewer's consent), framed as a way to review and improve her interviewing approach. Surprisingly, most interviewers agree, with the condition that the footage remain private and stopped during sensitive discussions, such as those concerning the salary.
With the footage in hand, Karla and Bea review the subtle details. Karla helps her read the body language of the interviewers — where she may have spoken too long or too little, moments when her energy dropped, or where she missed a chance to assert confidence. They work not just on answers, but on presence, branding, and social intelligence, further building Bea’s social capital.
Bea’s next interviews are noticeably better. Soon, offers start rolling in.
Jane recommends she turn down the first ones — not because they are bad, but because Bea is on an upward trajectory, and a few more interviews will sharpen her skills even further.
Weeks later, Bea receives a job offer that amazes her. It features:
- a mid-sized company that is steadily growing;
- a team of experienced developers she can learn from;
- a modern tech stack and a generous training budget;
- participation in industry events;
- a better job title;
- a significantly larger salary; and,
- most importantly, remote work flexibility, allowing her to save time and money, and to reinvest both in further learning.
Bea’s mentors are not surprised. This is what they had been aiming for all along. Sometimes, it takes another company’s professional sales pitch to break the spell of misguided loyalty to one’s current employer.
After reviewing the job contract, Karla and Jane encourage Bea to accept — not just for the money or title, but for the extra time it will give her. Time to learn more, live better, and grow further. They warn Bea that early or frequent job-hopping might spook future employers, but in this case it’s worth it. Bea accepts the new job.
To Bea’s surprise, her mentors recommend that she go into the office every day for the first few months, even though the new job offers full remote working flexibility. They explain that an in-person presence at the beginning of a new job will allow her to build relationships faster, observe processes and office dynamics more closely, and better understand the company’s culture and expectations. Once she is established and confident, she can shift to remote work most of the time.
By now, the MentorGuild has gained enough experience to know that the onboarding phase is critical. When a mentee starts a new job, the MentorGuild temporarily resumes having conversations on a daily basis, to help:
- ensure that the mentee is mastering the key skills needed for the role;
- provide reassurance, especially as the impostor syndrome often resurfaces during transitions;
- identify and troubleshoot early challenges; and
- recommend relevant books, articles, courses, or exercises for rapid growth.
Bea returns to daily mentor check-ins — and thrives. With her strong work ethic and guidance from her mentors, she quickly proves her value in the new job.
Her mother is ecstatic. The salary is far beyond what she expected. The speed of Bea’s career growth feels almost unreal.
Tragedy and Recovery
One year after starting her second job, tragedy strikes: Bea’s mother dies unexpectedly.
The loss is devastating. Bea is heartbroken and alone — she now has only her younger sister, who is still in school. In the absence of nearby relatives, Karla and Jane step in, not just as mentors, but as steady anchors during the chaos.
They help with practical matters first — shielding Bea from exploitation, especially from the funeral home, which tried to manipulate her into buying an overpriced coffin and funeral ceremony. Karla calmly intervenes, recognizing the situation for what it is: another “near enemy” — emotional manipulation (to get Bea to spend more money) disguised as sympathy.
They attend the funeral in person. They gift a meal delivery service to Bea’s home for a few weeks, so she has one less thing to worry about. And they strongly advise her to take at least two weeks off work, so she has time to grieve, process the shock, manage paperwork, adjust to a new household routine, and figure out schooling and care arrangements for her sister.
Bea initially resists. She wants to return to work immediately — convinced that staying busy will help. But after some insistence from her mentors, she accepts their argument that taking care of herself and her family is the first priority.
A week later, panic sets in. Bea calls her mentors distressed and overwhelmed. She has just discovered that the family apartment carries $50,000 in unpaid property taxes. The government, she learns, will not allow her and her sister to inherit the home until the debt is settled. Until then, they are effectively squatters in their own home, with eviction looming.
Now Bea understands what her mother never told her: This was why she had pushed Bea to start earning money so quickly. Her mother had carried this debt, this burden, in silence — to protect her daughters from the stress.
And now the weight of that burden has landed squarely on Bea’s shoulders.
Bea is panicking about having to pay back her huge debt, and about the possibility of losing her home.
Karla is not personally affected by this problem, so she has the calm and mental space to think clearly and do in-depth research. She finds a government program that renegotiates housing debts, another program that arranges payment in installments, and reports on social media of an obscure program that offers relief from government debts for disadvantaged families.
She informs Bea about these programs and helps her fill out the necessary application forms. It turns out that each one of them worked. Bea reduced her debt from $50,000 to $20,000, and negotiated installments of $400 per month, which is a huge improvement. But even this amount is too much for Bea, given that she is now the household’s sole breadwinner and is responsible for her younger sister.
The MentorGuild then offers her a new contract to replace their current one. It has the same income percentage, but more work hours (around two years more), in exchange for a stipend of $600 per month for the first two years, enough to cover part of her debt repayment and give her some breathing space. After these two years, with the MentorGuild guidance, she will have raised her salary enough to pay the debt by herself.
The reason why the MentorGuild can offer this stipend is that Karla and Jane have been onboarding new mentees. One of them is an older man pursuing a career change. He has a good deal of savings, which he wanted to use to pay tuition in exchange for a reduction in the income percentage, while increasing the number of hours worked so he can have someone watching his back for many years to come.
He ends up signing a contract whose terms include tuition of $1000/month for the first three years and payback factors of 0.8% of the income from 18,400 hours of work (around 10 years). The MentorGuild accepted him partly because his tuition payments could be redirected to other mentees, like Bea. Their community of mentees would also benefit from the presence of a senior worker with extensive work and life experience. At the same time, he could get exposure to enthusiastic young people, learn about upcoming technologies, and exercise a bit of (informal) mentoring — in sum, generating synergy in the MentorGuild, thereby increasing their social capital.
This way, even new MentorGuilds that are not yet receiving a sizable income from long-tenured and high-income mentees can afford to accept talented people who just need a bit of money to stabilize their lives.
Bea feels that the offer is too generous, but the MentorGuild explains to her that it’s just good business, and her future income will compensate them handsomely.
Bea agrees to cancel the current contract and sign a new one — a process known as “rolling” the contract. She gains enough financial security to feel much calmer, and her job performance does not suffer. Her growth at work continues at a fast pace, under the advice of MentorGuild, and she learns more over the next few years, from many sources, including:
- formal Education provided by her mentors;
- experiential Education provided by her job; and
- advice from hanging out with her fellow mentees, in the true spirit of a guild.
Specialization
With about one year left in her contract (estimated, of course, as the only thing that matters is the worked hours), there is a second conflict of interest between the mentee and MentorGuild: While working as a software developer, Bea has fallen in love with data analysis, one of the sub specializations of her profession, but she wants to take it further and become a data scientist, a profession that is somewhat related to her own, as it combines software development and statistics. Her company has even offered her a position as a junior data scientist — with a lower initial salary, but higher salary in the long term. The “Girls Who Code MentorGuild” doesn’t have expertise in this area, but Bea has become friends with her mentors and loves the idea of having a MentorGuild to guide and protect her.
At this point, Bea sees a few options:
- She could wait for the current contract to end, then find another MentorGuild specializing in data science.
- She could start learning data science now, though this would detract from the time spent learning from her current position. When the contract ends, she would switch to the new field.
- Accept the new position now, and either:
- risk upsetting the MentorGuild because she has accepted a lower salary when it was supposed to be at its highest level (at the end of the contract); or
- claim that she doesn’t have to pay a percentage of her income to the MentorGuild anymore, given that her job is very different from the one she was trained for (arguable, and likely to involve lawyers).
Bea brings up her interest in changing careers with her mentors. Karla listens and suggests a solution that could work for everyone: Bea could partner with a new MentorGuild that specializes in data science, while still keeping her current MentorGuild for software development support.
Bea is excited. She would maintain her relationship with her current mentors, who already understand her strengths and weaknesses. They trust each other and work well together.
Bea names one MentorGuild that she has been considering. Karla and Jane express some concerns, but promise to investigate it. A few days later, they return with bad news. Despite strong marketing, the data tells a different story — this MentorGuild performs below average, with mentees earning less than expected for the time spent under their guidance, something clearly visible in the open data they must release as per the relevant MentorGuild laws.
Karla and Jane teach Bea how to evaluate MentorGuilds based on real data — not just flashy marketing. With this new skill, Bea spends a week researching. She returns with two solid data science–focused MentorGuilds.
Jane agrees that both are good options, but recommends the second one. Its mentors are introverts, like Bea. They are more likely to understand her personality, work style, and challenges. The other MentorGuild leans toward a more extroverted approach, which could lead to mismatched advice.
This is something that Bea had never considered, but she instantly sees Jane’s point. She reaches out to the recommended MentorGuild and asks for quotes.
The three parties enter negotiations. The Data Science MentorGuild sends an initial offer, but the terms seem standard — fit for someone just entering the workforce, not for someone like Bea who is switching careers, and already possesses strong relevant skills.
Jane steps in to explain. Bea is already trained and earning well in software development. On top of that, many common risks — like poor work habits, low emotional intelligence, or lack of workplace experience — do not apply. She understands how offices function and what is expected of her. What she needs now is to build knowledge in statistics and other data science fundamentals.
Karla and Jane add that they will continue to support Bea in such areas as software development and general career guidance — whether it is navigating office politics, asking for a raise, or handling workplace challenges.
The Data Science MentorGuild responds with a much stronger offer. Bea accepts. She signs a new contract for 11,040 hours — about six years — because she values having trusted mentors by her side. This new contract replaces her old one, as only one can be active at a time.
The split ends up being:
- 0.5% income for the previous MentorGuild, with Karla and Jane, down from 3% in the contract that was about the end; and
- 1.5% income for the new Data Science MentorGuild.
Bea is now set to pursue a prosperous career beyond anything she once imagined — supported by mentors who know her, believe in her, and are motivated to help her succeed. That is the core purpose of MentorGuilds.
Conclusion
This story was built around an ideal case: someone easy to guide, a low-hanging fruit. Bea has no major trauma, no mental health issues, no confusion about her goals. She was already studying on her own and eager to learn.
Even so, her path was not without challenges. Life is unpredictable. And Bea’s story shows how MentorGuilds can make a real difference — not just in solving work problems, but also helping manage personal life difficulties, and in spotting and seizing the kinds of opportunities that might otherwise be lost.