The Resistance Before the Breakthrough – The Teacher’s Edition

What a difference a week of phone calls can make.

I’ve seen the light.
I’ve come around.
I’ve changed my mind.

And it actually feels good.

First, let me be a sport and give a hat tip to those who done told me so from the start. Gary Chou, the mind behind Orbital, had encouraged me to organize a live gathering of the students in the beta version of the self-study ecourse based on my novel Picture Me Rollin’. The co-facilitators and advisors he brought to boot camp to support us in implementing our projects agreed.

Each and every time, I listened, smiled, nodded and said, “Yeah, but…”

I thought I had good reasons for my resistance to a live component to my ecourse. I mean, it’s an e-course, right? Among the other reasons, I had – all of which I still think are logical – it seemed that extending myself at that level defeated the purpose of using the digital tools available to gather people online.

But logic has its limits, and in those limits are emotional sinkholes. This became evident to me after holding the first round of office hours this week. Having candid conversations with my students revealed how much of my resistance was rooted I concerns that were not logical at all. After reflecting on these conversations, I can now see and admit that my resistance to organizing a gathering of my students was based on an attitude a lot like this.

I’ve known for a long time that the best teachers are willing to learn from their students even if sometimes it’s difficult. Often when it’s difficult because a flaw in your knowledge or pedagogy has been exposed or the power differential has been shifted out of your favor. Essentially, the growing pains comes from having your ego checked.

My students not only reaffirmed what I already knew to be true about the value of a live gathering, they also deconstructed my deepest concerns with clarity, humor and another kind of emotional logic. By the end of the last telephone call, I was actually looking forward to organizing something. Once my resistance crumbled, the floodgates to more creativity – both with respect to this endeavor and a few others on the back burner yet in the same vein – crashed open.

I genuinely believe that the greatest resistance comes right before the breakthrough. I’ve blogged about it before with respect to challenging students, and I often have comforted fellow teachers with this principle when they have lamented about students who dug their heels in when being faced with information that threatens to shatter a way of thinking upon which much of their worldview and sense of self has been built. I totally underestimated that this applies to teachers as well.

TWo office hours, and now I know better.


3 Steps to Getting 50+ Retweets on Twitter – Part I

OrbitalNYC 2014 - Assignment 3 - SQuintero

    1. Identify the latest celebrity to engage in some fuckery.
    2. Snark away using an existing hashtag created with the distinct purpose to clown said celebrity.
    3. Search the hashtag for impressive snark by others and RT those.

If You Spot It, You Got It

As part of the Orbital Boot Camp, we have to complete seven assignments. There are some that I’ve already accomplished before embarking on this experience. For example, being a published author and content producer, I’ve had people write about my work. Experience has shown also that I’m quite capable of composing a tweet that garners double-digit retweets and favorites. If I want to raise the bar higher for myself, my objective before the end of boot camp is to proactively complete these same tasks with the strategic intention of pushing forward my projects. I think I can swing it.

But there’s are two similar assignments, however, that I’ve been dreading. These are leveraging my networks to get an introduction to someone I want to meet (and actually have a conversation with this person) and sending a cold email to someone I want to meet (and, again, actually speak to this person.) These tasks scare the shit out of me.

Please Eat My Homework!

It’ll take a post much longer than I want to write at 11:48PM on a Saturday night to explain this fully so I’ll cut to the conclusion. I hate opportunists, but there’s this saying: if you spot it, you got it. That means if opportunists work my nerves, it just may be because I myself am an opportunist. Or at the very least wish I was more like one.

You spot it

Of course, being a skilled and consistent networker does not an opportunist make. There are plenty of people who are leveraging their networks for introductions and sending out cold emails because they believe deeply that what they’re creating is valuable and are determined to realize their ideas. Having worked in politics and entertainment has left me with some baggage I have to unload, and I’m ready to start unpacking.

So this weekend, I made an attempt to knock out both of these assignments. Results – or lack thereof – are pending. But at least I’m in the game, and I feel already a little lighter.


Fiverr, Freelancers and Interns, Oh My!

One assignment for the Orbital NYC Boot Camp for which I already have previous experience is hiring someone from a labor marketplace such as ODesk and Elance to do $50 worth of work on my project. My go-to source for finding affordable freelancers for simple tasks has been Fiverr. For the most part, my experience with Fiverr has been great.

Although sometimes guilt-inducing.

Unpaid Interns

My ecourse is based on a novel that is presently out-of-print. Now that my rights have reverted back to me, I have to republish it so that it’s readily available. There’s no just removing the binding (i.e. blow drying the spine until the glue melts so that the pages come apart easily and neatly), scanning the pages and compiling a PDF. It’s starting from scratch, including designing a new cover.

That means the novel has to be retyped, and if that has to wait until I can do it myself, it ain’t getting done. My time is better spent doing those things that only I can do and which can generate an income. This includes finishing that second YA novel in my two-book deal.

Instead I found a lovely young women named Madeleine on Fiverr who is retyping the manuscript for me. I send her PDFs of two to three chapters which is about 30-40 pages. I pay her $15-20 per batch, and she usually turns it around in a day or two. She’s been great and so long as she remains available, I plan on hiring her to retype all three of my out-of-print Black Artemis novels. We’ve calculated that would be almost 1,000 pages. At her rate, this means I’ll have three full-length novels retyped for less than $500.

If I had gone to a traditional transcription service, I’d probably pay that much for just one manuscript. I feel like I’m exploiting Madeleine even if she freely sought opportunities to do this work at this rate.

In comparison, when I’ve had the resources, I’ve also used a virtual assistance company where clients pay upfront for a certain number of hours per work like depositing savings in a bank account. The more you pay up front, the less you pay per hour.
(I use them mostly for audio transcriptions for another labor of love called The Feminist Love Project I initially used Fiverr for this, and that experience taught me the fundamental difference between paying a traditional service provider over using freelancers found in a labor marketplace. As you can imagine, the quality of the output could be an issue at times since freelancers often didn’t have the skills or equipment that businesses did, but for me it wasn’t the main issue since I wasn’t demanding complicated tasks.

Reliability was more of the challenge. A place like Fiverr is not the one to go to if you’re in a time crunch. One, you can’t assume the person who has his shingle up will actually respond to your query. I can’t even tell you why that is — there are surely 101 reasons. For the overwhelming majority of these folks, this is a way to make extra money. They have other things on their plate, and given how much work they’re offering for so little – it’s called Fiverr for a reason – they probably burn out often and need to take frequent breaks.

Two, because their prices are so low, freelancers often want to tweak templates and keep it moving. This is particularly true for design work from logos to landing pages. I once reached out to a freelancer on Fiverr asking how much he would charge to create a logo for me that was a parody of another logo. I knew precisely what I wanted, had the other visual elements he would need and requested a quote i.e. I was willing to pay more than his Fiverr rates. If he was as skilled as his copy boasted, he could’ve whipped out what I was asking for and made some easy money. Dude never replied.

Now it could’ve been some thing else entirely, but when I looked back through his samples, I saw how generic they were. I suspected that he had invested in some kind of software and wasn’t interested in (or capable of doing) work that required him to use any elements outside of his current toolbox. In fact, he wanted to design the logo based on a the minimal input from clients. Now maybe it was a matter of creative fulfillment or artistic pride, and I’m not mad at that, but he still could’ve just answered though if like this:

Bye Felicia

Three, when dealing with a freelancer from a labor marketplace, you do run the greater risk of unforeseen obstacles. Folks have computers that die, finals that call, and vacations that beckon. Again, ain’t mad at them ‘cause I’m not in a hurry. If I were, however, I’d take my task to CVA because the higher price I’m paying means that my job is going to be delegated to someone who has the time, equipment and focus to do it well and fast.

But I still use Fiverr for those tasks that can be fulfilled within its various constraints. It sparks an internal struggle though ‘cause, on the one hand, I sure as hell wouldn’t work for these rates (the ads on Odesk seeking writers pisses me off to no end. Go look. I don’t wanna here about it but look.) On the other hand, yo no soy hija de Rockefeller. Not by a long shot, and being a freelancer myself, paying someone pocket money for a simple administrative task isn’t like a major conglomerate seeking an unemployed intern.

Or is it?


To Sell What You Wish to Serve

survey says

Before the Orbital Boot Camp, my approach to creating and implementing this ecourse based on my novel Picture Me Rollin’ would most likely have been as follows:

1. Republish the novel as an ebook.
2. Create all the course content.
3. Recruit paying students.

Because of this boot camp, rather than creating then implementing, I’m creating and implementing at the same time. And here are some fascinating things about this radically different approach:

1. It’s still scary but more fulfilling.
2. It’s less overwhelming since we’re being encouraged and supported to move our projects forward with defined tasks than general phases.
3. Both potential issues and better strategies surface more quickly

A fellow boot camper blogged this week, “Where there’s pain, there’s opportunity. Where there’s opportunity, there’s innovation.”

Among other things, this sentiment reminded me of a few things. One, marketing experts often advise entrepreneurs to sell people what they want but give them what they need. So maybe your fitness program promises clients will “shed 10 pounds in 10 days,” but what you actually deliver is a healthier lifestyle that is actually sustainable. Two, on the underside of this marketing adage, entrepreneurs are encouraged to solve a problem. Specifically, we are told that people are most likely to pay to have a problem solved than to prevent it in the first place, and we should get clear on what point of pain we are attempting to resolve. Ideally, our solution should be one people are wiling to buy. Three, when we are marketing our solution, we are at once attempting to convince our prospects that we are selling what they want, but in delivering our product or service, we are resolving their true pain which just might be something far deeper than they even realize.

This made me wonder then if, when we are compelled to innovate in response to pain, we are actually being called to serve.

So where does this leave the creative entrepreneur whose product is something often deemed a luxury? A painting. An album. A novel. Is there a pain we’re attempting to or at least capable of resolving when we create these things?


I tested this assumption recently by following a whim and asking my followers on Twitter to share the titles of works of fiction they found reading to be healing experiences. What I was seeking was an affirmation that reading fiction has the potential to be more powerful than just providing a temporary escape as a form of self-care. I got it. A frequently cited example was Alice Walker’s THE TEMPLE OF MY FAMILIAR for the way it helped readers to better understand and navigate family dynamics even when they are abusive.

While I have professional and financial hopes for creating this ecourse, I also have activist and spiritual intentions for it. I would like the experience of reading the novel, working through the assignments and sharing challenges and discoveries amidst a community to be one that’s healing for all the participants. As a person who believes that books choose their readers rather than vice versa, this is what I want for anyone drawn to this novel and this online class. My instinct says that there exists a real opportunity to create something that can help a reader resolve a point of pain

But what if all they want is a writing workshop? Of course, the unfulfilled yearning to write is extremely painful. If someone is looking to learn how to outline a novel or pitch it to editors, however, I have no desire to teach that no matter how lucrative it might be. It may be the problem that many are willing to pay to have solved, but it doesn’t give me a strong urge to serve.

That’s the question I’m grappling with now. While I certainly want to midwife my students desires to write, I’m uninterested in teaching elements of craft for its own sake. This just ain’t that type of class. Take my priority action step for this week: design that first lesson. In it I use a technique for developing character to prompt my students to examine themselves. For the students who are willing, there’s a great potential to go quite deep out the gate.

I once took an online quiz to determine the limiting belief that was getting in the way of my success. After answering a short series of questions, the results were that I feared that others would not want what I had to give. It immediately rang true, then and now as I brace myself to review the surveys about expectations and experiences that my beta testers so honestly completed, that doubt has certainly been triggered.

This is where Orbital gets real because just like a boot camp, I gotta do it. I gotta read these surveys, offer my lesson, and speak to my participants, all to discover where, if any, the overlap exists between what they want, what they need, and how I want to serve.

With my old approach I may never have reached step three as the drive to create lessons and materials petered out in the vortex that is working without accountability and feedback. If I had finished, I would’ve learned what I needed to, but if history and personality are indicators, much too late and at high cost. That is, to the extent I would’ve ran out of motivation to revise and reboot.

I’m going in…


Start Before You’re Ready

Life of a Project. jpg

The main lesson from boot camp this week was something I have been hearing a great deal for the past two or three years. Marie Forleo impressed it upon us at her last Rich Happy Hot Live event in 2012. Almost all the folks whose newsletter I subscribe to – from online business coaches to “conscious” entrepreneurs – have all written about this at one point or another.

“Start before you’re ready.”

I used to think that starting before I was ready was the precise reason I had difficulty seeing certain projects to fruition. I would have this grand vision in my mind of what I wanted the final product to be. No matter how much I tempered my ambition, what I envisioned always surpassed my resources. Still I’d be so enamored with the idea that I would start anyway. I’d take some pretty bold steps running on little more than passion.

And passion is a master at manipulation. Passion makes you believe, “Whatever I don’t know, I’ll learn. Whatever I don’t have, I’ll get. Whoever I don’t know, I’ll meet.”

How many times I’ve dove in because of passion having forgotten how damn fickle he is. I’ll invest scant time, energy even money into something based on his promises. In fairness to him, he’s pretty reliable in the beginning. I’ll face those first, unforeseen obstacles, and Passion and me, we’ll power through them like the Six Million Dollar Man and the Bionic Woman.

Steve and Jamie

Hurdling past those first few challenges, I’ll gain momentum. Often the vision gets bigger even as the resources are dwindling. No matter. I feel unstoppable.

Then the first major challenge rears its head. It’s not always something insurmountable. It’s just big. And unexpected.

Sometimes the obstacle is not even related to the project. It’s just life happening. I remember being in the middle of producing my web series and online network HomeGirl.TV when I was diagnosed with breast cancer in January 2012. I could say that was the reason I put the project on hiatus, and no one would blame me. The truth, however, is that my diagnosis became a handy excuse for putting HomeGirl.TV on pause because I was already blindsided and disappointed in a certain aspect of the project. (Another thing we learned at boot camp this week is the need to make assumptions and test them. I had made an assumption about HomeGirl.TV that did not pan out, and it was demoralizing. The lesson is one that I’ve taken into another one of my side projects the Feminist Love Project.)

And so often when that first huge challenge shows up – the one that reminds me just how I have even less time, energy and money to address it – where the hell’s Passion at? Over there flirting with the next idea. When he’s really callous, he’s stirring up old feelings with an ex i.e. that side project started and abandoned before the current one.

So what’s going to be different with the Picture Me Rollin’ ecourse? My guess is it’s going to be Orbital’s distinct mixture of accountability, community and actionability (I’m a writer. I make up words. You’ll live.) With any project, there’s a seemingly endless to-do list. The Orbital faculty has charged us to just identify one priority each week and get that task done. If we do more, excellent. If that one task is all that we complete, hey, our project is still moving forward. We share with each other what that priority task is and are holding each other accountable for getting it done. No one wants to keep coming back every week with a status update that starts with, “Well, I was gonna but, you know, because life….”

But it’s not like with past endeavors I didn’t have some form of community, accountability and actionability. I have several ideas as to why boot camp is a different experience, but I’m going to let some time past before I expound on that. I have this suspicion that over the next few weeks, a lot of assumptions I had about how to get things done are about to be blown out of the water.

For now the assumption I’m testing is that there are people who will want to take this ecourse. My task for the week was to reach out to people on my mailing list who said they wanted to be beta participants when I was ready to rock. Starting waaay before I’m ready, I not only sent out an email to this list, I also posted the call for testers on Twitter and Facebook. The call includes a survey/”application” (which you can find here if you’re interested.) I’m seeking a maximum of fifty people, but my goal is to recruit at minimum fifteen by the end of next week.

Progress: I’m halfway towards my goal, and the majority have come through tagging specific people on my Facebook post. Does this surprise me? No, I had many reasons to suspect that relying on my mailing list wasn’t the way to go. More on that once the deadline has passed.

And talk about accountability. I never would’ve thought never mind dared to attempt to recruit participants until I was much farther along in developing the content for the course. That would have put me at great risk of taking far too long to get it done if at all. Instead I now have this level of buy-in – one of my fellow boot campers described the first page of my survey as “intimidating” so completing it says something about a person’s willingness to commit to the process – that requires me to produce.

Doing this has also reacquainted me with one of the pleasurable byproducts that often emerges when one takes actionable steps towards completing a project. Sometimes you show up, knock out that bite-sized task and realize you’ve got the bandwidth to do a little somethin’, somethin’ more. Before you know it, you’re creating far more than you thought you could.

Working on the survey got me thinking about how I’m going to deliver the novel to my participants since I need to republish it. Next thing I know, I’m messing around with Canva and have the mockup of a new book cover for not only PICTURE ME ROLLIN’ but my two other Black Artemis novels. I only discovered Canva a week ago, and I saw myself being very methodical about learning how to use it – tutorial by tutorial – before attempting to make anything.

Yeah, I’m pretty stoked I didn’t do that.

BAM Book Cover Collage


Hustle and Pivot


It’s hard out here for a novelist.

One of the hardest things is finding the audience for your book. While it’s becoming easier for writers to both publish and promote their works themselves, the majority of strategies touted by experts – especially those exploiting social media and other online technology – are geared toward non-fiction writers. Whether how-to, self-help or even memoir, there are countless ways to use the issues, themes and events your work raises and explores to draw attention to it.

In fact, if you look at the many experts and coaches that rely heavily on their online presence to build their businesses, a book of some kind is often the entry point for prospects. It’s an inexpensive (if not free) resource that enables them to share some of their expertise and cultivate relationships with potential clients.

But what if you’re making the whole shit up? What if your life isn’t the kind that Sony would adapt into a film for Julia Roberts or Sandra Bullock? What if you don’t have an existing platform in a field that lends itself to the online business-to-business or lifestyle coaching model? What if, to paraphrase Albert Camus, you’re writing lies through which to tell truths?

The default for many creative people is to become teaching artists. If it lights you up to share your favorite techniques, inspire others to pursue their creative dreams and godparent the talent of others (and I do), this can be a wonderful thing. Until it isn’t.

Even if you’re a wonderful teacher who finds the work fulfilling, it’s only sustainable for so long. You hustle for the few available gigs with nonprofit organizations or academic institutions. Few of these gigs pay well enough for you not to have to create a patchwork of them to pay your rent. Juggling multiple freelance assignments means less time for your own work. This is especially true if you take nurturing the creative spirits of others as the sacred act that it is (and a Miss Celie curse on you if you don’t.) When you do, you’re investing your creativity into developing lessons and exercises for your students which can leave your well parched when the time comes to focus on your own projects.


There’s got to be other ways for creative to become entrepreneurs who can leverage their existing creations into multiple revenue streams. There’s got to be ways to do this using all the technology available to us from social media platforms to content management systems. There’s got to be ways to do this that enable us to combine our multiple passions and be of service.

I have an idea for one way to pivot some of the online tools and strategies that entrepreneurs use so that they work for fiction authors. I’m creating an 8-week ecourse based on one of my novels. Picture Me Rollin’ to be exact.

And if you’re reading this, you probably already know enough about me to get why this is going to be quite an enterprise (And if on the off-chance this blog post is your first encounter with me, this recent feature in Bitch will suffice as an introduction into what I write and why I write it.)

This is not an academic course in creative writing where we’re using my novel to illustrate points of craft. Yes, to some extent it is a creative writing workshop. But in my vision for this e-course, teaching the elements of writing fiction is the smallest objective. Nor is it just a book club where the participants have weekly access to the author although it’s that, too.

This is “self-study” course.

This is a group coaching program.

This is a consciousness-raising collective.

This is an incubator for social justice projects.

This is, I hope if nothing else, a healing experience.

Over the next 12 weeks, I’m going to develop this e-course through the Orbital Boot Camp and documenting my experiences here. I’ll share what I’ve done and what I’ve learned from it. Please join me on this journey.