Issa Rae MasterClass Review: Is it Worth It?

Our review scores for the Issa Rae MasterClass:

  • Lessons – 9/10
  • Workbook – 8/10
  • The Community – 5/10
  • Value – 8/10
  • Overall Verdict – Very useful!

Issa Rae MasterClass Pros:

  • Assignments – Most of the lessons end with mini-tasks that encourage involvement, as well as enabling the skills Issa has discussed to be put into practice.
  • Structure – There is a strong structure to the lessons. They start off general but build to in-depth areas of the industry.
  • Engagement is encouraging – Issa doesn’t present writing as impossible. Instead, she addresses each aspect of the industry and embraces the cons that come with the process to turn them into positives.
  • Relatability and accessibility – Issa refers to constant ideas, themes, media platforms and content that most will be aware of. This aids in understanding and expands accessibility.
  • Naturalistic – Sequences that would normally be edited out (such as laughing takes) are left in. This enforces the authenticity that Issa encourages.

Issa Rae MasterClass Cons:

  • Similarity- The lessons are carried out in the same way of Issa talking to the camera. So it can often appear repetitive and tiring if all the lessons are watched sequentially.
  • The case study of her show Insecure slightly limits the lessons. As much as she does explain it, there is a limit if not everyone has watched or is familiar with the series.
  • In terms of the advice, there is occasionally a lack of specificity in terms of actionable practices.

What is MasterClass?

MasterClass provide online classes from a variety of well-known talents, covering a diverse range of topics that give advice, provide lessons to improve, or simply inspire.

The lessons are carried out in multiple short videos all of which are easy to access and resume at any time. You can watch them all in one go or pick them up here and there.

They are engaging and easy to understand, with the website keeping track of your progress to ensure accessibility. As well as providing videos, there are also workbooks that encourage participation and further the lessons taught.

Issa Rae Masterclass

The Issa Rae MasterClass

Issa Rae is a writer, producer, and actress, most notably known for her TV Show, Insecure. She is, as she describes, a multi-hyphenate, someone who has several professions and abilities. She writes, directs, acts and produces.

In her MasterClass, you learn how her career grew from starting out on YouTube to having her own show on HBO. She discusses her experience in getting to where she is now, from the lowest of lows to the highest of highs.

As she goes through her experiences, she teaches how to craft character, build a narrative, how to go from a pilot to a series and even how to sustain longevity in an industry rife with expiry dates.

Issa Rae Teaches Creating Outside the Lines | Official Trailer | MasterClass

Issa Rae MasterClass – The Lessons

Issa’s lessons are carried out in 14 videos ranging from 5-15 minutes. She speaks directly to the camera which engages and builds a personal connection, as though it is two friends interacting. This is also highlighted through the assignments. It’s apparent that Issa wants the lessons to be interactive and productive. 

In her introductory video, she highlights the importance of paving your own path. The industry won’t come to you and she enforces the need to make your career happen for yourself. The message she pushes is “Getting out of your own way.”

Lesson 1: Finding Your Voice and Inspiration

In the first lesson, Issa focuses on authenticity. She believes that the most authentic story is showing the good with the bad. The key ways she suggests for how to find your voice are:

  • Hone in on what you want to say.
  • Find what you like and what/why you like it. Then pick out the pros and cons.
  • Be an active viewer- question how someone tells a story and what you would’ve done differently.
  • She stresses the importance of not diving right in. Instead, educate yourself around it.
  • She also highlights the significance of telling the story that you feel is missing from the cultural landscape.

The use of the first assignment to “Just Get Started” builds on Issa’s message of authenticity, as the assignment is simply to write every day. Her MasterClass encourages writing, not to follow a set structure or genre, but to simply get words onto a page in order to establish your voice. Because the only way to find an authentic voice is to keep on creating.

Lesson 2: Developing Your Story

The second lesson of the Issa Rae MasterClass takes the viewer through how to build on their initial idea. There is a need to tap into reality to know what you’re really writing about. Issa suggests that it is a person’s worldview that makes the story interesting.

Once again, she marks authenticity as pivotal. This way people can feel involved in the story. However, she also makes clear the importance of starting with yourself as a creator instead of what others want.

“I don’t believe in bad ideas. I believe in bad execution.”

To develop a story, Issa says you:

  • Need to be selective. What’s the story you can tell best?
  • Play to your strengths.
  • Try multiple ideas. Don’t attach yourself to one idea, it’s okay and important to move on to another.

Lesson 3: Insecure Pilot Blueprint & The Why

The case study of Issa’s show Insecure is introduced at this point. She takes us through her style of creating a pilot episode with the hope of it leading to a TV Show.

The main message she stresses is ‘show don’t tell‘ in screenwriting. There is no need to write it all out.
The initial two aspects of a pilot blueprint for Issa are:

  1. Setting up your characters- Introducing the audience to the characters. Why will they want to follow them? Set up backstory and establish the dynamics between the characters.
  2. Establishing your “why today?”- The ‘why today?’ is the “why am i watching this?”. It acts as a premise for the pilot/series, so it needs to be enticing and have a hook. She emphasises that it should set up what is to come.

This is a fundamental part of screenwriting that is clearly and well-described here. The why of your story is possibly the most important element of the script. And Issa makes that clear in an accessible, simple yet poignant way.

Insecure - Trailer - Official HBO UK

Lesson 4: Insecure Pilot Blueprint & Conflict and Series Setup

The fourth Issa Rae MasterClass lesson provides the next two steps to building a pilot blueprint. These are:

  1. What is the conflict and tension? Conflict needs to be worthwhile and progress the story so you don’t write yourself into a corner that you won’t know how to get out of.
  2. Are you setting up the rest of your series? No one cares about the conflict/tension if no one cares for the characters and their journey. There needs to be a sense of what to expect for the rest of the potential series.

Issa imposes the need for tension and stakes. The core of the conflict is who the antagonist is and what the protagonist is up against. Conflict must be built throughout to establish these elements.

Although the topics that Issa discusses are somewhat expected and basic, she deconstructs them throughout the MasterClass to fully delve deep into the steps it takes to build up each element of the story. Furthermore, she always relates these lessons back to her own experience and work, which provides a handy blueprint.

Lesson 5: Creating Characters Grounded in Reality

This is the point when the lessons start to become more focused on particular aspects. In this case, it’s the creation of realistic characters. 

  • Issa suggests the act of constantly mining life for ideas, especially regarding the people around you.
  • She emphasizes a need to research.
  • Speak to people who resemble the character, collaborate and be inspired by real people.
  • In addition, she addresses the importance of natural dialogue. Every word needs to matter and it must be authentic and rooted.  

As much as this lesson of Issa’s MasterClass stresses the importance of characters that are realistic there is the perspective of creativity becoming slightly limited. If, for example, the characters are too similar to real people then their depth is restricted.

Hence, as Issa’s MasterClass goes further into character development, it is important to remember that a character should simultaneously be realistic but able to extend creatively to fit the narrative, themes and overall dramatic purpose.

Lesson 6: Creating Multidimensional Characters

The sixth lesson goes from creating a character to one that is layered and even more realistic.
Issa simply makes apparent that when creating a character, you need to think about both their flaws and redeeming qualities. Ensure they are well-rounded.

Issa addresses the idea of a character being the “hero of their own story”. Although this is a familiar concept in screenwriting, she uses it adversely since and enforces the importance of the “hero” having negatives. The character cannot just be deified.

Her MasterClass carries this idea throughout as Issa constantly highlights the importance of the story over the audience. By prioritising the story, authenticity is ensured.

This is one of the best things about the Issa Rae MasterClass – the extent to which she explores authenticity. It’s a word often spoken out but rarely delved into in terms of how to achieve it. Here, it’s really explored in a tangible and helpful way.

Insecure: Real Talk | HBO

Lesson 7: Interpreting Feedback and Creating Your Story

Issa teaches that a pivotal part of building a series is receiving feedback. She makes it clear that things change as you get notes from different people, and that rewrites are normal.

Simultaneously, whilst responding to feedback there needs to be confidence in the story you want to tell, or it’ll go in multiple directions. She highlights the difference between confidence and being possessive. You can’t feel threatened by criticism or advice but you need to remain assured in your vision whilst being open to improvements. It’s a tricky balance.

Addressing the relationship between confidence and possessiveness provides a fresh view on how to handle criticism. Issa implores that a writer must be willing to accept the critique in order to improve the story, whilst maintaining credence in their writing and story. This amalgamation is present through Issa’s focus on collaboration. She presents the industry as one where collaboration is a necessity.

This is a refreshing take from such a multi-hyphenate. Even someone who seems to do so much on her own admits that collaboration is one of the key factors in success.

Lesson 8: Getting Your Stories Out There

This lesson presents the difficulty of getting work out there. However, it does highlight that there are many ways to do so. Issa tells us to just focus on things one bit at a time. Don’t do it all at once.

She makes it clear that to get stories out there often takes time, but that building a routine/schedule is important as the audience will come eventually.

Issa’s lessons at times can be considered to state the obvious. However, she always ensures that she provides anecdotal detail that is not easily available.

This lesson exhibits just that as she highlights the importance of marketing to your intended audience. By being the creator you know what really matters. It’s, therefore, easier to decide what to promote in order to attract an audience.

Lesson 9: Resourcefulness is Everything

Issa discusses how essential it is to use the resources you have access to, to do the tedious work and to do the actual work. Anything can be a resource. She stresses to not be afraid of imperfection as nothing will always be perfect.

The main goal of this lesson is:

  • Do the best you can with what you have.

Whilst addressing how being resourceful is vital, she also acknowledges the difficulty of balancing it with other life commitments. However, if you want it that much you must do what it takes to make it work.

“I’m busy is valid but also an excuse. If you want to do it, do it.”

Issa is not afraid to address the faults that hold many back, as she discusses procrastination, for example. She makes it clear that procrastination is normal, but to get over it a routine needs to be planned.

However, what Issa fails to address is that the method of routine is not a way to recover from procrastination for everyone. For some, a routine can, in fact, encourage procrastination.

Although through her stressing the need to do whatever to make it work, she establishes that an individual needs to do what is best for their creative process. This is helpful advice, if not particularly specific or instructive.

Lesson 10: Collaborating With Like-Minded Creatives

In order to foster “the best product”, coming to the realisation that you can’t do it all yourself is key. As collaboration is needed to be successful, you have to let go of certain aspects to others that can do a better job.

“Be confident in what you know”

Collaboration leads to a diversity of perspective, style and talent. Furthermore, communication is key to collaboration.

Issa makes it clear that good communication encourages transparency. The clarity that comes with transparency is what enables solid collaboration because everyone is in a rapport with one another. This means the story can be its best, reaching higher ground by everyone bringing something to the table.

Insecure: Molly's Andrew Situation (Season 4 Episode 2 Clip) | HBO

Lesson 11: Empowering Yourself and Those Around You

The eleventh lesson of the Issa Rae MasterClass presents the idea of working together to get into the industry, but the importance of self-empowerment. Issa makes clear that by working together and self-inspiring…

  • Longevity is attainable through helping each other.
  • The more you doubt the smaller the chance, so use your voice and don’t let anyone take that away.

Longevity in the entertainment industry is hard to attain. Issa makes this apparent. When Issa makes clear that to achieve longevity by helping one another, she means to invest and become involved in multiple areas of the industry.

Now as useful as the advice is, it is not possible for everyone for a variety of reasons (location, finance, circumstance). So the MasterClass is at times limited regarding specific advice. However, it works as a touch-paper, lighting the fuse for you to go out and find collaborators, if not exactly giving you the tools.

Lesson 12: Diversify Your Skills

Here Issa introduces the idea of a multi-hyphenate, someone who undertakes various roles and tasks. She declares to not try and do it all as “one tool sharpens the other”, but also to take on other roles as it garners experience.

However, she stresses to only attach yourself to a couple of roles. Don’t do many roles just for the sake of it but because it is enjoyable.

Issa is somewhat oxymoronic here as she is critical of being a multi-hyphenate due to it being overwhelming, whilst encouraging the need to gain experience in various areas.

As she herself is a multi-hyphenate, the class may have benefitted from suggesting that when entering the industry you need to gain experience in multiple areas. Then when building a career one can stick with one area and once the career is solidified one can potentially explore becoming a multi-hyphenate.

It can feel a little like the advice zigzags. However, the main takeaway is to be open and focused, advice that is never not worth listening to.

Issa Rae Collaboration

Last Lesson: Pep Talk

“You should always be your biggest hype person”

Issa closes on the importance of being excited for what you’re doing because no one else will be if you won’t be. She also enforces that it is a long journey and that it doesn’t come easy.

She makes it apparent that failure isn’t the end of the road. Issa discusses that there is always another shot as long as you don’t give up.

“You don’t make all the shots that you make”

There’s a realism to the Issa Rae MasterClass overall that is refreshing. Issa never sugarcoats the difficult parts of the industry. In this, she provides both a daunting task and an inspirational one.

Ultimately, she stresses the importance of putting in the work and being resilient in the face of inevitable failures. This might not be the most original advice but it rings true nonetheless. And attached to a relatable approach, it feels much less intimidating.

The Issa Rae MasterClass: The Lessons and Their Ratings

  1. Finding Your Voice and Inspiration- 8/10
  2. Developing Your Story- 8/10
  3. Insecure Pilot Blueprint: Characters & the Why- 7/10
  4. Insecure Pilot Blueprint: Conflict & Series Setup- 9/10
  5. Creating Characters Grounded in Reality- 6/10
  6. Constructing Multidimensional Characters- 7/10
  7. Interpreting Feedback and Creating Your Story- 8/10
  8. Getting Your Stories Out There- 6/10
  9. Resourcefulness is Everything- 7/10
  10. Collaborating With Like-Minded Creatives- 8/10
  11. Empowering Yourself & Those Around You- 8/10
  12. Diversify Your Skills- 8/10
Issa Rae - The Classes

Issa Rae MasterClass – The Workbook

The Workbook presents itself as being one of the most useful parts of the course. Although it does repeat what was in the lessons, it takes what the lessons provided further. This is evident through the structure, as it represents a ‘how to’ for the reader. It acts to get readers involved whilst telling them what they need to know.

By going into more detail than the lessons did, it allows for more ideas to be presented and discussed, for example, how to pitch a pilot and sell it to a network. It also demonstrates the collaborative work of Issa and Shonda Rimes, as Shonda sets out her story blueprints, whilst Issa lays out her writing blueprint.

It does differ from the videos, with fewer assignments than in the videos. Instead, the workbook acts to motivate through a pep talk segment, which helps to inspire and build community and understanding.

Additionally, it provides in-depth Q&A segments with those who work in different parts of the industry. This proves the idea that Issa discussed in the lessons in terms of having an awareness of all the different roles in the industry. You, therefore, build an understanding of how everything works altogether. This is clear here.

Overall, the workbook is beneficial as it is easier to follow than the lessons due to it being similar to a ‘how to’. This allows the workbook to become educational and encouraging.

Issa Rae MasterClass – The Community

If there was one area that the MasterClass was lacking in it would be the community. As interactive as it is, and Issa builds a mutual understanding through both the lessons and workbook, there is no real place or guide on how to correspond with those in a similar situation. Hence, the community that is crafted is somewhat limited digitally through people carrying out the assignments, and following the instructions in the guidebook.

The main connection is with Issa. This is the most important connection as she is the teacher, and the understanding and relatability she provides is vital and reassuring. However, the overall MasterClass does suffer a little from that lack of a further interaction.

Issa Rae MasterClass – The Value

MasterClass charge $180 annually. It is a substantial amount and although it does upload new classes monthly it is not known what those classes are until close to release. No one wants to pay for something that they may not get use out of or doesn’t relate to their interests.

However, the classes themselves are very useful if it is what you need. The Issa Rae MasterClass is vital to those looking to not only write but also create their own show. Issa teaches the skills and then gets you to put them into practice.

Ultimately, the Issa Rae MasterClass is worth the money as:

  • She gives an insight into the industry in a way that serves to motivate instead of dissuading.
  • Issa teaches skills that in other forms would be expensive or hard to get. And she provides them in an engaging, motivating, but most importantly, educational manner.
  • The lessons and workbook both provide skills that are needed for longevity within the industry. It is information that is essential to becoming a writer.

The membership to MasterClass supplies you with access to all it has to offer, in order to get the highest value for money. If you do subscribe and are unfulfilled by what MasterClass has to offer, a 30-day guarantee of a refund is supplied.


Issa Rae MasterClass – An Overview

Issa’s empowering outlook is truly what carries the lessons. There is no sense of giving up. Instead, she provides the information that is needed to motivate oneself in order to carry on within a tricky industry.

At times it does seem slightly futile with the constant case study of Insecure, as each project is different. However, this does supply a good way to comprehend what she is discussing. The relatability that Issa herself provides, but also in the way she provides the information, is essential to how valuable the lessons are. No stone is left unturned as she addresses each area a new writer would need to know.

Her lessons are targeted at upcoming writers and those who are looking to get their material an audience. She speaks encouragingly to multiple aspects of the industry, inspiring ambition.

As Issa states, the lessons are about “Getting out of your own way”. This is exactly the tone she presents throughout all the videos.

The Issa Rae MasterClass is a great place for those who are looking for motivation to carry on with their career as a writer, for those who are starting, and for those wanting to know where to go next after writing. She is not afraid to address the hard topics, whilst showing the positives. But she also encourages the role of the self to get to where you want to get.

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This article was written by Libby Laycock and edited by IS Staff.

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