Prison Professors

Annotation

In this MasterClass, you will learn how to apply the Straight-A Guide to real-world success by studying the journey of Sara, an entrepreneur and project manager who built her business in the fashion and entertainment industry. Though Sara never went to prison, she lived by the same principles we teach in this course—principles that helped her build a thriving freelance career by focusing on preparation, relationships, and consistent execution.

By studying Sara's journey, you'll discover how to:

Transfer soft skills from any environment into professional opportunities.
Define your own version of success.
Create structure in your life, even without external supervision.
Build a network of relationships through authenticity and value.
Transition from employment to entrepreneurship with minimal capital.

This lesson is part of our MasterClass series for students who have completed Preparing for Success After Prison and Triumph: Building Bridges to Success.

Objectives

After completing this lesson, you will be able to:

Describe the key decisions that shaped Sara’s entrepreneurial journey.
Connect Sara’s actions with the principles of the Straight-A Guide.
Reflect on ways you can build trust and credibility, starting now.
Identify steps for using your environment to prepare for post-release success.
Apply lessons from Sara’s story to begin developing your own personal brand.

Background

When I first met Sara, I knew immediately that her story was one our students needed to hear. Though she’s never been involved in the criminal justice system, her life exemplifies transformation, hard work, and living with purpose. Her journey aligns perfectly with the principles we teach in the Straight-A Guide.

Sara didn’t become successful through shortcuts or privilege. She applied herself, earning incremental levels of success in the same ways as other leaders we've covered:

By showing up,
By honing her skills,
By refusing to complain,
By coming up with clear plans,
By overdelivering for the clients she served, and
By seizing every opportunity to grow.

Her determination and resilience make her an inspiring role model for anyone striving to rebuild their lives and achieve success after prison.

Sara grew up in the United Kingdom. As a teenager, she didn’t have a detailed roadmap for her future. Like many of us, she wasn’t born with a plan. She followed her interests—especially her love for travel, language, and culture. That’s what led her to study French in college.

Some people might question how a degree in French could lead to a successful career in New York’s fashion and entertainment world. Yet as we’ve seen time and again, success doesn’t always start with a straight line. It starts with learning, with curiosity, with the decision to make the most of your time.

Anyone can do the same, even if they start from inside a prison cell—ask me how I know!

After college, Sara began her career in corporate offices, working in project management roles. She handled logistics and planning for events hosted by banks, law firms, and other large institutions. She wasn’t in charge—at least not at first. She was a W-2 employee.

Despite being part of the paid help, she always considered herself part of the team, and she paid attention. She showed an eagerness to learn how the business worked, which made her invaluable to colleagues. She started to see that the same skill set could be applied across many industries. That realization was the seed that would eventually blossom into her entrepreneurial career.

Then came a major pivot in her life—she moved to the United States. When she arrived in New York, she didn’t have clients lined up or a blueprint for success. But she had a vision. She knew she wanted to work in the world of entertainment and fashion. More importantly, she was willing to start small.

Her first freelance job? It wasn't glamorous, and it wasn't what she expected to do long term. She did whatever had to be done, including carrying boxes from one area of an event to another. Despite years of experience in corporate event planning, Sara took an entry-level gig moving equipment at a fashion show.

Why?

Because she was in a new city, in a new country, and she wanted to break into the industry. Instead of trying to protect or feed an ego, she focused on the tasks at hand to succeed. She had the right attitude, as we cover in our preliminary courses. Sara believed in starting wherever she had to start, and letting her work speak for itself.

That small job opened the door to others. People noticed her work ethic, her attitude, and her ability to manage chaos with calm. Within a short time, Sara started to get bigger jobs, managing high-profile events with budgets ranging from $10,000 to over $1 million. She found herself working with celebrities and global brands—not because she had a marketing agency behind her, but because she earned people’s trust. One successful project led to another. Word spread.

Sara didn’t rely on advertising or social media. She doesn’t even have a public-facing website. Her entire business is built on relationships—on the strength of her word and her reputation. When people hire her, they know they’re hiring someone who will deliver.

But her journey wasn’t easy. Sara had to make a lot of sacrifices. As an entrepreneur, she gave up the steady paycheck and benefits of a traditional job. She had to learn new skills—like accounting, invoicing, budgeting, and vendor negotiation. She had to take full responsibility for every decision, every success, and every failure. Some months were lean. Other months were overwhelming with work. But she persisted, stayed organized, and always found ways to adapt.

Sara also learned how to scale her business without building a massive team. She works as a solo operator, hiring contractors on a per-project basis. Her vendors range from caterers and florists to graphic designers, stage builders, and audio engineers. Each project is unique. Each client has different needs. And it’s Sara’s job to bring all the moving pieces together.

She described her job as part logistics expert, part creative director, part negotiator, and part people person. She’s constantly managing personalities, solving last-minute problems, and staying calm under pressure.

From listening to her during our interview, I could tell that she thrives in that space. The stress, the long hours, the tight timelines—they don’t scare her. In fact, they energize her.

Sara’s journey is a testament to how great business leaders build their careers—through meaningful relationships, pivotal opportunities, and unwavering integrity. She didn’t come from wealth. She had no family connections and no formal business education. What she did have was an unrelenting drive, a clear vision, genuine humility, steadfast grit, perseverance, and the determination to put in the hard work.

Sara's story is one that should inspire and motivate members of our community. Anyone can pursue their dreams and goals, no matter the obstacles in their way. Her journey is a reminder that success does not come easily, but it is achievable with hard work, determination, and a clear vision.

Despite not having many connections in the business world, Sara built a career that brings her a high level of satisfaction and fulfillment today. Her story highlights the importance of networking and making genuine connections with other productive people.

Moreover, Sara's unrelenting drive and unwavering integrity are qualities that set her apart from others. These are characteristics that every leader should strive for as they navigate their own career paths.

People in prison can take a lot away from Sara's journey: You can do this too. Whether you're in a cell right now or working toward release, you have the power to start building your future.

Maybe you start by studying a new skill.
Maybe you build your communication abilities or expand your knowledge of industries that excite you.
Maybe you begin, like Sara, by saying yes to something small—something that doesn’t seem glamorous, but gets your foot in the door.

The world doesn’t owe us success. But it will reward those who prepare, who show up, and who serve others with consistency and excellence. Sara became the CEO of her life not because she waited for the perfect job, but because she created value wherever she went.

That’s why we’ve made her part of this MasterClass. She lives the Straight-A Guide:

She defined success for herself.
She set goals and worked relentlessly.
She took action and kept moving.
She aspired to a bigger life.
She acted with integrity.
She held herself accountable.
She stayed aware of opportunities.
She remained authentic in every interaction.
She celebrated every achievement, large and small.
And she lives in gratitude—for every client, every lesson, every new day.

You may be in a dark spot today, but at any time, you can begin sowing seeds for a brighter future. Get to work.

Vocabulary

Start by building your vocabulary. Below I provide 15 key words that relate to this lesson. Learn the definition, and then task yourself with writing a sentence for each one, like the examples I provide in this lesson.

Resilient – Able to recover quickly from difficulty.
"Despite facing early challenges, Sara remained resilient and built her business."
Transferrable – Capable of being applied in different situations.
"Her project management skills were transferrable across many industries."
Credibility – The quality of being trusted and believed in.
"She built credibility by delivering results time after time."
Consistency – Steadiness in performance or behavior.
"Success came from her consistency in showing up and doing the work."
Execution – The act of carrying something out.
"The client trusted her with the event because of her flawless execution."
Freelance – Working independently rather than being employed by one organization.
"Sara decided to go freelance to gain more control over her career."
Initiative – The ability to assess and begin things independently.
"Taking initiative helped her get ahead of others in the industry."
Bespoke – Custom-made or tailored for a specific client.
"She created a bespoke experience for every event."
Authenticity – The quality of being genuine.
"Her authenticity helped her earn long-term clients."
Scalable – Capable of being expanded or made more profitable.
"Her business model was scalable because it allowed growth without heavy overhead."
Recap – A summary of what has been said or done.
"Sara always provides a recap presentation after an event."
Frequent – Occurring often.
"Her clients became frequent sources of work through referrals."
Meticulous – Showing great attention to detail.
"Her meticulous planning made the events run smoothly."
Adaptability – The ability to change in response to conditions.
"Adaptability helped her succeed in a fast-moving industry."
Viable – Capable of working successfully.
"She turned her freelance side job into a viable business."

Self-Directed Questions

How does Sara’s journey help you think differently about your own path to success?
What skills are you currently developing that could be transferrable to different industries?
Describe a time in your life when you took initiative. What was the outcome?
In what ways can you start small today to build trust and credibility for your future?
How can you use your current environment to build relationships that matter?
What’s one industry that excites you—and how can you begin learning more about it?
How could you apply the Straight-A Guide to launch a career, even without formal education?
What does it mean to be authentic in your actions and communications?
How do you currently define success, and how has that definition changed over time?
What fears or limiting beliefs do you need to overcome in order to move forward?

Reflection Journal

Use this journal prompt to reflect on how the lesson applies to your life:

What can you do today—even from inside prison—to show others that you're serious about success? Write about one action you’ve taken or could take that will show your commitment to change.

Sample Response

Question 4: In what ways can you start small today to build trust and credibility for your future?

While I’m serving time in prison, I may not have access to business meetings or networking events—but that doesn’t stop me from laying a strong foundation. I start small by working through the independent study courses that I receive. Every time I receive one of the lessons that Prison Professors sends, I respond to all questions in the lesson.

Then, I send my responses to the questions home, and my family adds them to my profile on Prison Professors Talent. This self-directed initiative helps me build a transparent record, showing others all the ways that I use my time inside to prepare for success outside.

Besides working through the lessons myself, I use them to teach classes to others who join me in these self-directed study programs. We work together. I show them the value that comes when I document my progress every day in a journal, tracking how I spend my time and what I’m learning.

Trust and credibility start with consistency. Every time I follow through on a promise, show up for my class, or write a thoughtful letter, I’m building my reputation.

I might be in prison, but I am basically following the guidance I learned from Sara. I show up. I get things done. I do the little things so that more opportunities will open when I get out. I anticipate that people will look at the body of work I’ve created. They’ll see the lessons I’ve completed and get a sense of my self-directed work ethics. I'll leverage that body of work to open new relationships. Some of those relationships will grow, and I'll bring mentors into my life, and they'll become my advocates.

Like Sara, I’m willing to start small. She carried boxes to get in the room. I’ll write articles and mentor others to earn my seat at the table.

Project: Building Your Portfolio

Create a one-page professional bio that you would want to appear on your Prison Professors Talent profile. Include:

A definition of what success means to you
What steps you’ve taken to prepare for your release
What industries interest you and why
How your time inside has shaped your values and goals

Ask a peer or facilitator to read it and offer suggestions.

Quote to Remember

“I didn’t have ego going into it. I was carrying boxes, doing whatever was needed.” —Sara

What small task can you commit to this week that will prove your dedication to change?

Knowledge Check (Optional)

What core values helped Sara grow her business without formal business training?
How did Sara build a career without using a website or advertising?
List three Straight-A Guide principles that Sara’s story clearly demonstrates.
What are two examples of how Sara turned a small opportunity into long-term growth?

Final Message

Use this MasterClass to think about your life differently. Apply what you learn. And when you're ready, memorialize your journey by creating a profile on Prison Professors Talent so we can advocate for you.

You have the power to become the CEO of your life—starting now.

Get to work.

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MasterClass with Sara