How To Write an Allegory With Jordan Gross

Jordan Gross - Writing an allegory

Would you like to write an allegory?

An allegory is basically a story that reveals a hidden meaning or moral. One great example is The Alchemist by Paulo Coelho.

An allegory isn’t necessarily as long as a novel, but it should leave the reader with an understanding of a key concept or idea. An allegory is a little like self-help, except in the vein of a story.

Jordan Gross is author of the allegory The Journey to Cloud Nine and a TEDx speaker. He’s also a prolific non-fiction Medium writer. In this interview, Gross explains:

  • The problems with traditional self-help books today
  • Why he veered away from this genre
  • How to write an allegory
  • What it took to land a TEDx speaking gig
  • How he’s selling copies of his new book through public speaking  

And lots more.

I start by asking Jordan why he decided to write the allegory The Journey to Cloud Nine in the first place


Bryan Collins: So if you could start Jordan, by telling me why you decided to write The Journey to Cloud Nine in the first place.

Jordan Gross: Yeah, absolutely Bryan. So I need to backtrack a little bit. So this is my second book, The Journey to Cloud Nine. And my first book was a self published book called Getting Comfy: Your Morning Guide to Daily Happiness. And it was what I did the month after I quit my corporate job. So I was still looking for jobs casually, kind of taking a little bit of a break. And I said I've got all this content based off of personal development, books that I've read, and podcasts that I've listened to and now why don't I put this content into a book format. So that's what I did. And I thought I was this 23 year old kid who quit corporate America.

Jordan Gross: I went to fancy universities. And here I was with this morning routine concept. I thought I was going to be a New York Times bestseller right off the bat. But obviously I learned very quickly that that's very challenging to do. So when I self published the book, something that happened was that my friends weren't reading it. They were just supporting me, but they weren't reading the book because they told me that they didn't want to learn about my morning routine. They didn't want to read self-help because they didn't want to be told what to do. Right? And I think that's why a lot of self-help doesn't necessarily work as effectively as it should because people want their own insights.

Jordan Gross: People want to make their own realizations about their own lives. They want to be their own person. Right. So when I came up with the concept for living life on cloud nine and The Journey to Cloud Nine book, I did a ton of research for about six months to nine months. Interviewing people all over the world about the key ingredients of living life on cloud nine. How you have a cloud nine moment, day, week, life, whatever it is.

Jordan Gross: And I got all these insights and I found some key themes and patterns and I did research about euphoria and ecstasy. And I said, "Okay, I have two potential avenues to go down now." I can either do the same type of self-help book that my friends won't read and just share these insights and create like an acronym like I did with the first book or just share different interviews like I did with the first book. Or I can do something a little bit different, right?

Jordan Gross: And I can basically trick my buddies into reading my book by sharing my findings in this entertaining fictional story. And that's what I did with The Journey to Cloud Nine. I basically created this character who is not living a cloud-nine life. And then I juxtapose all the decisions he's made in his life that were not so cloud-nine with what his life could have looked like had he chosen the cloud-nine lifestyle through everything that I learned, right? So I'm by no means telling the reader, here's what you have to do. I'm showing them by using emotion, by using characters, by using the plot, exactly what your life could or could not look like as you go about the book and go about your own life.

Bryan Collins: What struck me about the book is it reminded me of Paulo Coelho in that it feels like an allegory.

Jordan Gross: Yeah, I'm so glad you said that. It puts a big smile on my face. My favorite review that I've received so far is that it's a millennial version of the Alchemist. So it is... I'm not going to run... I'm 25, so I'm going to write based off of what I know and to my own peers. But yeah, that's one of my favorite books of all time is the Alchemist. And I like to write what I consume. So I was reading a ton of self-help up until about a year ago and I got bored of it. Honestly, I was like there's contradictory advice and all the information's getting overwhelming. So why don't I try to just read a fun story. And I picked up the Alchemist and I said, this is how we sustain our long-term personal development by getting our own insights from these kinds of stories. So I said, "Well, why don't I give myself a try at writing a story just like this?"

Bryan Collins: And did it take long to write because that's quite a challenging... Or quite a challenge you set out on to create an allegory.

Jordan Gross: Yeah. Exactly. This is the craziest part of this entire experience. November, 2018, I had the idea to write about cloud nine and I was done with the first draft by January 1st of 2019. So it took about five weeks to put it all together and I kid you not, you know the state of flow, right? Being in flow.

Bryan Collins: Yeah.

Jordan Gross: I didn't think it existed because I'd never been in it, but when I was writing The Journey to Cloud Nine I could sit at my table for 11 hours straight and forget to go to the bathroom. And I drink a lot of water. So I go to the bathroom a lot. And it was just crazy. The words just kind of poured out of me. I would reread the next day, what I wrote the day prior and said, "Who's that guy writing that stuff?" Because it was just such a surreal type of writing experience.

Bryan Collins: And I know you said you were working for 11 hours, but on a typical day, what did it look like? You would get up at what time? And you would write for how long?

Jordan Gross: Yeah, yeah, so a typical day writing for me, for The Journey to Cloud Nine is actually waiting until the end of my day in order to get started with the writing because I liked to take the experiences from my day and see if I could weave any of the stories or the people or the scenes that I saw in my everyday life into the actual allegory. Right. So I would go through a whole day of writing on Medium and LinkedIn and all that and coaching and speaking whatever else I do, and then around 6:00 PM, I would go to the Starbucks near my house. I would sip on a tea and one day I would do a bunch of research based off of the chapter that I wanted to write.

Jordan Gross: And then the day after, I would write a full chapter and then the day after that I would review that chapter and then the next day I would start it again, do research, write, review, research, write, review. And it was from about six till 8:00, 8:30 every evening for about five weeks. And like I said though, there were a couple of those days where I was just in such a groove, had nothing else to do where I just did 11, 12 hours.

Bryan Collins: So you said your first poker Getting Comfy was traditionally published... Oh, sorry, excuse me. Self-published.

Jordan Gross: Self-published.

Bryan Collins: Is The Journey to Cloud Nine self-published or traditionally published?

Jordan Gross: The Journey to Cloud Nine is the middle step. So Boutique Publishing is the firm. And it's been an amazing experience. Basically the difference is that I had all of the team members that a traditional publishing firm would have. They had an editing team and a design team and a marketing team and a distribution team, except I paid them upfront as opposed to the traditional publishing house gets a percentage of your royalties. So I own all the rights and royalties. And I just paid them up front. So that's a big difference. Then also with traditional, obviously they have bigger distribution channels.

Bryan Collins: So the book has some amazing testimonials at the stars.

Jordan Gross: Mm-hmm (affirmative). Yeah.

Bryan Collins: Is that something the Boutique Publisher helps you with? I think I saw was it Daniel Pink?

Jordan Gross: Yeah.

Bryan Collins: Yeah. That's a great testimonial to get.

Jordan Gross: Yeah, no, the publisher doesn't help at all. And I've actually heard from a lot of people who I know in the traditional publishing have been traditionally published that they won't really help you like that. They can make some connections, but at the end of the day, all the marketing and outreach is still on you unless you're like this huge big-time author. So I'm definitely not there yet. But for me, those testimonials came from two years of deliberately growing my network and adding value to people.

Jordan Gross: And the story with Daniel Pink for instance, is that he's a Northwestern alumni and he kind of had a similar trajectory of his career that I want to take where he studied pre-law or he studied history at Northwestern. Then he went into law and then he didn't love law. So he was in politics for a little bit then all of a sudden he start writing books on human performance, right? He made that total switch. So I shared with him that story about how I just want to make a total switch too into the writing world. And we got on the phone and then I just stayed in touch for the last little while and he was willing to read the book and share a testimonial. So with him, [inaudible 00:08:55], Dorie Clark, it's been because I've been following their work for a year or two now and constantly trying to review their pieces or see if I can connect them to somebody. Just add little things to their lives. So that when I finally need to make an ask, they'll be willing to say yes just like they did.

Bryan Collins: So Jordan, before we started recording, we were talking about the business behind a book and a lot of non-fiction authors I've interviewed don't make an income directly from the book, although they might make some royalties but they generally offer coaching or courses are some our service that helps their readers. But you are taking a different approach. Could you could you describe what you're doing?

Jordan Gross: Yeah, absolutely. So ever since I was young I had this mindset of I'm going to do whatever every... I'm going to do the opposite of whatever everybody else is doing. And when I was like in high school, I was a shot put thrower, the shot put [inaudible 00:09:55]. And I'm 5'9, 180 pounds. And meanwhile the best shot put throwers are like 6'5, 300 pounds. And there I was competing with them because everybody told me you're not going to be a good shot putter. But I found a way to use my speed and agility to be a good shot putter as opposed to everybody using just their brute strength, right? So that's always been my mindset to just kind of... Whatever everybody tells me, prove them wrong and prove myself right. So that's what I want to do with the book. And like you said, so many authors will tell you, right, when they write their book, "I'm not making money off of this book." Or people will say to me, "So what are you doing to make money? You're obviously not selling the book itself."

Jordan Gross: And every time I hear that, it motivates me one step further to just sell 25,000 copies of this book, right? So selling the book is my main strategy. And then all the other tools that most people use for their main monetization strategies, speaking, coaching, courses, I'm just using that to sell the book, right? So if I'm going to go out and do a speaking engagement, I'd much rather have them say, "We're not going to give you a fee, but we'll buy a hundred books," than, "We won't buy any books and we'll give you $1,000 speaking fee." Right. So yeah, that's what I'm doing. And even my coaching clients, I have them pay me in books now.

Jordan Gross: So they just have to buy whatever my fee is in books as opposed to just paying me on PayPal or whatever it is. And then yeah, my outreach strategy is very personal. It's totally human-connection based. So I reach out to a hundred new people a day, 25 people who I've already had conversations with. I offer free chapters of the book so you can get a feel for it at first. And then after that, I hope that you enjoy the free chapters enough to go sign into Amazon and purchase the full thing.

Bryan Collins: So we're recording this interview at the end of February.

Jordan Gross: Mm-hmm (affirmative).

Bryan Collins: And the book is out about a month and you already have nearly 90 reviews, which is very impressive for a newly launched non-fiction book. How long are you going to focus on your strategy of just selling the book?

Jordan Gross: Yeah. So my strategy for this year is until about the middle of July, it's all going to be behind the scenes work. So podcasts, interviews like this, personal outreach, posting content, more medium articles, things like that. Everything I can do from right here where I'm sitting at my table. And then the six months after that, my goal, like I told you before, is to do 50 speaking engagements. So getting out there, really going to networking events, getting to schools, prisons, juvenile detention centers, corporate... Maybe not corporations. I think I have a different message than a traditionally corporate place, but really just getting out there and spreading the word and sharing this message in person.

Jordan Gross: So I'm going to start doing the outreach for that next month. And again, that's behind the scenes work where I can just sit here and email people.

Bryan Collins: So I understand how you could turn a typical non-fiction self-development book into a talk or a speech, but how would you turn an allegory into a speech?

Jordan Gross: Yeah. So my speech is actually going to be totally based on storytelling because that's what I believe is setting this book apart from the rest of the personal development world. So The Journey to Cloud Nine is made up of nine key ingredients for our lives that I've uncovered, right? And what I'm going to do in a talk is provide a story that shows each one of these nine ingredients. So for example, the first component of living a cloud-nine life is playfulness, right? So I'll tell a story about a character in the talk who has an inflection point where he could either make a choice to play or not play, and it's going to be totally based on the audience's engagement. So I'm going to have a tool where they can vote on which way the story goes. And depending on which way the story goes is how the rest of the story will unfold.

Jordan Gross: So if they choose the cloud nine path and the story will go where the character goes the cloud nine path with all the rest of the clouds, and then they'll just be such an active audience component where they'll stay focused throughout the entirety of the talk. And ultimately it will reveal how to live a cloud nine life. And ultimately the message will be that you are the storyteller for your life, which is why they have such an active role in the presentation. So that's [crosstalk 00:14:26].

Bryan Collins: That's a good approach.

Jordan Gross: Yeah.

Bryan Collins: And have you tested that yet?

Jordan Gross: I haven't tested it yet. I'm giving a TED talk in two weeks from now on basically the power of stories. So I'm hoping that that provides some leverage as to how I can get into these places and start giving this presentation. But I'd love to come back and tell you how amazing things are going with the interactive talk that I want to start giving.

Bryan Collins: So before the interview, I was looking at your profile on Medium and it's safe to say you're fairly prolific. I think you publish an article almost every day. So how do you balance writing with promoting your book and your other parts of your business?

Jordan Gross: Yeah, I love routine but I hate monotony. So I've got a really structured day. Every day I literally print something out so I can cross off with a pen, 18 different activities of my day. So I start really early with your typical gym and self-care stuff. And then after that Monday, Wednesday and Friday I write something new on Medium. And for me, I'm like a short, quick story type of hitter on Medium. So I'll write something in an hour. That's a three to four minute read and then on Tuesday I'll proofread or Thursday I'll proofread and then I post on that day. So that's pretty good. And then in the middle of my days I do pretty much all promotional stuff. I do all my outreach messages, I do all of my podcast interviews, I do my LinkedIn content and things like that.

Bryan Collins: What publications do you find are working well for you on Medium at the moment?

Jordan Gross: For Medium, Mind Cafe.

Bryan Collins: Yep.

Jordan Gross: [inaudible 00:16:11] Adrian Drue who just kind of pops those up once you send them in. And the readership there I think is really nice because they're looking for useful ways to think differently and that's what I'm all about, right? Trailblazing a new way of thinking for people. Other than that Publishers is really good. That's a little... I try to put some of my lighter stories onto Publishers, Mind Cafe are like a little bit more of a deep thinker type of story. When I share stories about my process, right? Like how I got a TED talk, I put that on Better Marketing through Nick and the Better Marketing team. And every so often I have an article I think can really pop and that's when I published through Forage, Medium's personal development platform.

Jordan Gross: So those are really the ones I stick to. If I write something that's a little bit more emotional, I'll send it over to Dan at P.S. I love you. But those are the ones I stick to. I don't want to go too much. Right. So I think those five are a good place to be. And post grad survival guide. If I read something about being a 25 year old or something like that.

Bryan Collins: Yeah. Yeah. And would you say Medium is a key part of your writing career at the moment?

Jordan Gross: I really think so. A couple of different reasons. One is just credibility and visibility, right? Just growing a following on there. I also love consuming, right? So LinkedIn is probably my biggest platform, right? I've got over 20,000 followers on there. But the way that I grew was through engaging with other people really. So I love to consume other people's content and share my thoughts on their work. And that's how I started on Medium too was just by reading a lot. So that's why I love Medium so much because I get to read your work, I get to read Mike's work and all these people that we know. But yeah, other than for the visibility side, obviously you get to earn on Medium, which is nice. And then you can put some calls to action to your books on Medium.

Jordan Gross: I haven't tracked conversion for that or anything yet.

Bryan Collins: So what would you say as the difference between putting a post or article on Medium versus LinkedIn?

Jordan Gross: The main thing that comes to mind is I mean first audience. LinkedIn, I pretty much know because I'm so proactively reaching out to people on LinkedIn, I can recognize almost every name of somebody who's engaging with my piece so I can have personal conversations with them. Medium is a little bit more anonymous. I don't really know who's liking my articles or reading them and you don't really get a chance to connect with your audience as much. And then the other thing would just be that on Medium the article has a potential to earn based on it's performance as opposed to LinkedIn where you don't get any money from LinkedIn.

Bryan Collins: Yeah. It's interesting you bring up the topic of money because I was talking, excuse me, to an editor recently and I was saying that it's easier than ever for artists or creatives to earn a living from their work online. And she was explaining that a lot of people still struggle with that. So I'm curious what your take is for a writer or for an author, do you think there are more opportunities to earn a living these days or what do you think?

Jordan Gross: I'll say absolutely that there are more opportunities, but I will not say by any means that it's easy or even easier than it has been. Maybe it's easier because there are more opportunities and avenues, but you still need the consistency.

Jordan Gross: You still needed the quality of work. You still need the entire body of work to actually start to make a living. Right. And look at our buddy Barry, who's been writing for four years and just now his work is really starting to gain him some income. Right? And for me, I'm making fine money, but I'm by no means wealthy. Right. But it's been a year of consistency like you said. And even I wasn't consistent for a couple of months and that definitely shows I had to rebuild myself after a three-month hiatus. So what I will say all in all to answer your question just with a simple phrase is that you can't just think that because there are more opportunities to earn that you will all of a sudden be an earner. It doesn't work like that. You still have to put in the work.

Bryan Collins: I like that Jordan. So you talk about consistency. So that's something I think is very important for anybody creative because if you turn up every day and produce 100 words or 500 words, they can quickly stack up on top of each other. So you'll have 10,000 or 50,000 more at the end of a few months and that's enough to turn it into into a book. So if you're focused on marketing your book, are you still blocking aside some time for working on the next book?

Jordan Gross: It's so great. It's funny you ask that now. I'm thinking about starting the next book in two weeks after the TED talk. So right now I really just want to make sure that that TED talk is crisp and clear. I probably spend a couple of hours a day on just rehearsing for that. And then once that talk is over, I'm going to start the new book and my goal is 500 words a day because my book The Journey to Cloud Nine is 35,000 words. So it's shorter than most books and that's my sweet spot. I think that's the length I want all my books to be, because Mitch Albom is my favorite writer and his books are nice and concise. 200 pages, probably 45,000 words are his. He's got some longer ones, but The Five People You Meet In Heaven or The Next Person You Meet in Heaven or nice and short and sweet. So yeah, that's my goal. I can get a book done in two months probably if I keep up with that consistency.

Bryan Collins: Yeah. Steven Pressfield's books, which are very popular are also quite short. I remember counting up the words in the chapter and it was about three or four hundred words.

Jordan Gross: Seriously, in a whole chapter?

Bryan Collins: Yeah. Yeah.

Jordan Gross: Yeah.

Bryan Collins: But I didn't feel like I'd been shortchanged. There's a lot of takeaways in the book.

Jordan Gross: Yeah. And that's you know what? I think that's a psychological trick, and I haven't researched this, but for me, why I love a Mitch Albom book is because the chapters are so short. Two things, one, when I finish a chapter, I'm like, "Yes, I got a chapter done." And you get that sense of accomplishment, like a small win. And then also the chapters are so short that you want to keep reading because you're like, "Oh, this chapter is only two pages. I can do that." And then you get to finish that and you look at the next, how long the next chapter is, and you're like, "Oh, it's only four pages. I can do that." So next thing you know, you've finished his book in one sitting, in three hours because you're just like, "Oh, I can push further, I can do this." And you're winning along the way. So that's a big thing I took from his books. And then the other thing I'll mention is like The Five People You Meet In Heaven. This is his another little trick.

Jordan Gross: You want to know who that fifth person is, right? So he starts by showing you who the first person you meet in heaven is. And then once you meet the first person, you're like, who are the other four? Right? So with me, The Journey to Cloud Nine, I start you on cloud one and then you see what happens on cloud one. So my goal for the reader is to say, "Well, I want to see what happens on cloud nine. What is cloud nine?" So I take you to cloud two, three, four, five all the way to cloud nine and I just hope that you want to continue reading to see what that final cloud is all about.

Bryan Collins: In terms of continuing to read, will the next book be an allegory or is it too early to say?

Jordan Gross: 100%. Yeah. 100%, I'll share with you this, my idea right now is to do a trilogy for my next three books. Doing allegories on nighttime routines, morning routines and midday routines. So I can kind of do my research and then share stories about how to create those different parts of your day.

Bryan Collins: And do you have... You already talking about your morning routine, but do you have an ideal afternoon or evening routine?

Jordan Gross: I do, yeah. My morning routine is that COMFY: Calm, Openness, Movement, Funny and You. My nighttime routine is called COZY and my midday pump up is called AMPED.

Bryan Collins: Yeah.

Jordan Gross: And yeah, so those are all acronyms that I'm going to start to write a story about moving forward.

Bryan Collins: Yeah. I could see how they could work. Wow. But in a book that's an interesting way to approach this.

Jordan Gross: Yeah. Have you ever read the The 5 AM Club by Robin Sharma?

Bryan Collins: I have. Yeah. Yeah. Yeah. It was an interesting book.

Jordan Gross: Yeah. That's the thought. I used to do something like that.

Bryan Collins: I like the concept behind it.

Jordan Gross: Mm-hmm (affirmative).

Bryan Collins: Just finally your TED talk. How did you go about getting a TED talk for your book? How did that work?

Jordan Gross: Yes, it's always one of my favorite stories to tell because it just proves that you don't really need this tremendous platform to get something that you desire, like a TED talk. Right? Because the story for my first talk was that I had no platform. I got it only a couple of months into self publishing that first book. So I wasn't big on LinkedIn, I wasn't big on Medium yet. I just had an idea for a talk and I think what most people do, 99% of people probably is think that they have to go through the normal avenues to get a TED talk of going in there and seeing the TEDx website and going to the application pool and filling out this application and doing a sample video and then submitting it and hoping for the best. Right.

Jordan Gross: For me. I love people. So I feel that no matter what, people can always help us. So what I did was I found a couple of talks in my area and instead of going to the application pool, I went directly to the organizer of the event and I researched who this person was, and I tried to add value to his or her life. And because I was doing that, we developed a little bit of a relationship and connection. They were more likely to say, "Hey, is there anything I can do for you?" And then a couple messages in, I said, "Well, I happen to be a speaker. I saw that you gave a TED talk, would you be willing to consider having me for your event?"

Jordan Gross: And a couple of them sent me to the application pool, which I filled out and those didn't work out. But one lady in particular, she was a teacher and I told her how this morning routine could help her students when they get into the classroom, and she said, "Yes, we'd love to have you." So that's how I got the first one. And then the second one was very similar. It was about reaching out, adding value and sort of going behind the scenes in order to get the talk. Not having to apply with all the other applicants.

Bryan Collins: And has the TED talk been helpful in terms of building your brand?

Jordan Gross: Absolutely. Yeah. I think for the first talk, I stepped away from the getting comfy stuff so I was just doing it for the experience, but I really think this second one is going to be the spark plug for these allegories that I'm going to write for the rest of my life. Because the talk itself is an allegory. I'm going to tell the talk in the form of a story and share the lessons throughout the story with the ultimate reveal that personal development can be more beneficial for you if you read these allegory type books. So yeah.

Bryan Collins: That's definitely different to the other personal development books I've read, which is a good thing because there's a lot of personal development books that follow the same structure. So if people want to find more information about you or buy The Journey to Cloud Nine, where should they look?

Jordan Gross: Yeah, so buy The Journey to Cloud Nine, it's on Amazon. Just The Journey to Cloud Nine by Jordan Gross on Amazon. More information about me and all that I do is And this is all spelled out journey T-O cloud And then if you want to get in touch with me, I love like I said personal connection. LinkedIn is the best place, so it's just Jordan Gross on LinkedIn and I answer all my messages, I promise I get back to everybody on there.

Bryan Collins: Well best of luck with the promoting the book for the rest of the year and also the TED talk.

Jordan Gross: Yeah. Thank you man. I appreciate it. And this was great. Thank you so much for doing this.


The Alchemist by Paulo Coelho

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