How The Pros Do It: 10 Questions With Jordan Gross

The only way to reach your targets in life is to get to work. But it’s easier said than done. Only a fraction of people in life are actively working towards their goals. They know how to create and use the right tools and processes to generate progress for themselves. A lot of these people have a ton of interesting things to say. So I thought I’d interview them.

Most of my weekly guests created their own business, and they got where they are today by successfully implementing self-discipline in their life. To each one of them, I ask questions about their life, their learnings, their tools, and sometimes about which celebrity they would like to have coffee with.

There are no rules for success, only consistency in the work you do. None of the people I interviewed are super-humans. They’re just dedicated, and they have a lot of awesome things to teach us.

Let’s get to it.

My guest this week is Jordan Gross. Jordan left the corporate world to chase his dreams at age 23. He is the founder of The Journey to Cloud 9 where he inspires people to confront their past and redefine their future through coaching, speaking and writing. He wants people to think about their lives and personal development through the lens of creative story telling. His book The Journey to Cloud 9 is a fiction, his coaching has a lot to do with telling stories about life, and his speaking is all about how we as individuals need to take a story-based approach to self-improvement as opposed to taking advice and aimlessly implementing it into our lives. He is also the author of Getting COMFY: Your Morning Guide to Daily Happiness.

Do you have a morning routine?

Yes, and it is super important to me. My first book was all about morning routines, Getting Comfy: Your Morning Guide to Daily Happiness. COMFY is my five-step morning routine. It stands for:

  • Calm
  • Openness
  • Movement
  • Funny
  • You

My morning routine changes a lot, but it always has to hit those 5 buckets.


I wake up and do a little bit of deep breathing. In through the nose, out through the mouth.


Quick gratitude that I say out loud. “I’m grateful for my parents, for my health…”


I’ll head over to the gym and get my workout in for the day.


I’ll watch a funny video, or post something that makes me smile in the morning.


These days, what I do for myself is head over to Linkedin and start commenting on some other people’s posts so that I can add value to their lives right when I wake up. It’s something I want to do rather than have to do.

I wake up anywhere between 4:39am and 5:39am, depending on the day and on when I get to sleep the night before. I don’t eat until later on. I have a weird sensitive stomach, and I know my body very well. If I were to eat first thing in the morning it wouldn’t go too well.

What is the number one habit/routine you attribute the most success to in your life (online and/or offline)?

Doing and trying things every single day that I have no business doing. In other words, it’s doing something that makes others question my sanity, asking “You’re doing that?”, “How do you do that?”, “Why would you do that?”

An example of that could be a big thing like quitting my job to become a writer, speaker and coach at age 23. On a more daily basis, things like:

  • Reaching out to hundreds of people a day asking them questions
  • Going on podcasts, doing interviews
  • Reaching out to industry thought leaders everyday
  • Reaching out to TEDx organisers to get TED talks

Things that nobody else would consider doing. I make sure that I do at least one of those things every single day, truly getting outside of my comfort. I also make sure it’s something that’s going to benefit me in the long term.

What is the number one productivity item you can’t live without?

My planner. I’m pretty old school, I like to handwrite things. I write down everything I need to do today, and I physically cross those things off. There’s something about crossing it off and feeling that I did it that makes me want to be productive and allows me to keep up the momentum throughout the day.

The One Book you recommend for self-improvement and/or productivity?

I love books, right now mostly audiobooks. When I read paperbacks it’s usually fiction. I’ll say that the fiction book that is most advantageous for people’s personal growth is probably The Alchemist.

In terms of non-fiction, my number one favourite book that sparked my desire to get into personal development was How to Win Friends and Influence People by Dave Carnegie.

Can you tell us about your use of journaling and goal tracking?

I’ve actually been off my journaling game recently. I have been doing that gratitude in the morning. I’ve been waking up pretty early so I try to have a quick morning routine and get to the gym as fast as possible. But when I did journal and when I will be journaling again, I do what one of my buddies told me.

I write down:

  • Gratitude
  • Strengths
  • Weaknesses
  • Accomplishments
  • Sleep log
  • Food log
  • Goals log
  • Reflection on the day prior
  • Projection for the day ahead

That’s my entire journaling routine.

The second part of the question is about goal tracking. The way that I view goals is by not so much focusing on the goal itself, but rather on me becoming the person who has the best opportunity to achieve that goal. I set these big lofty audacious goals for myself. My goal right now is to become a New York Times bestselling author by age 30. So I create a bunch of micro goals that go with it:

  • I have to write a book
  • I have to sell a certain number of copies
  • I have to reach out to a certain number of people
  • I have to have a certain number of followers and connections
  • I have a certain number of conversations
  • I have to do a certain number of talks

With that in mind, everything I do leads up to this huge goal and everything else is a micro goal on my way to getting there.

Your website is about your project on positivity, happiness, redemption. Can you elaborate on the whole project?

The journey to Cloud 9 is everything that I’m working on right now

  • The book
  • The speaking
  • The coaching

It all started out from an Uber ride I had. We passed a dock with multiple boats, and the name of one boat jumped out at me. The boat was called Cloud Nine. I asked my driver: “What does Cloud 9 mean to you?”

There were 3 things that I noticed from his responses.

1. There are momentous life occasions we have throughout our lives, such as wedding, having children, childhood memory… That allow us to feel that Cloud 9 sense of euphoria.

2. There’s a certain number of principles we need to live our lives according to in order to have and maintain this overall Cloud 9 feeling and lifestyle.

3. When you live on Cloud 9 it’s because you’ve made the decisions that are most in line with your heart and your intuition as opposed to societal expectations, norms, or what your peers are trying to tell you.

Those were the 3 primary components. I started asking people after that: “What does Cloud 9 mean to you?”. The more I got these responses, the more I realised the patterns.

The website is an opportunity to share these interviews, these insights. It’s an opportunity for me to talk about how I coach people to living their Cloud 9 lives, to talk bout the book The Journey to Cloud 9, and to share my own Cloud 9 story, and how I am truly living every single day according to my purpose and what I think is most fulfilling for me.

You’re your own boss on different projects. How do you manage your time between your business and your private life?

This is my daily schedule. Right now I’ve got 16 things that I do every single day.

  • Lift
  • Train
  • 5 Linkedin comments
  • Post Linkedin
  • 1 Medium edit
  • 1 write/review and submit on Medium
  • 100 messages
  • 2 influencers outreach
  • 2 podcast search/outreaches
  • Reach back out to 30 people who have the free chapters
  • 25 new connections
  • Linkedin comments responses
  • Linkedin message responses
  • Phone calls
  • Creative outlet — 500 words per day
  • Fun

I have rather long days, but I have breaks too. For me, work and life are so synonymous, because my life is about growing myself personally and helping others grow personally. In practicing what I preach, everything I do throughout my day is related directly to how I can live my own Cloud 9 life and how others live theirs.

Regarding my free time, it really changes every single week, and it depends if I go out or not. If I don’t go out on a Friday night I’ll probably wake up early on Saturday and get in a couple hours of work before spending some time with friends or family Saturday during the day. My private life is very separate. I know how to separate and to focus my mindset on the task at hand versus being present when I’m out during social activities with friends and family.

Because we’re in the football season right now, Sundays are pretty much reserved for that. But again, it starts at 1pm here in New York. So I’ll wake up around 6–7–8am and put in 2–3–4 hours of work. I try to do a little bit of something that is beneficial for my business everyday.

Before going on your own, you worked in the corporate world. What made you take the step to leave it and start your own thing?

My corporate job was in restaurant management. I was in this leadership rotational program with a big restaurant group. I was on my feet 13 to 14 hours a day, and then a couple extra hours doing the end-of-day paperwork.

One night at work, something happened. I wall all by myself in the restaurant. I had just gotten out of the meat closet to count meat, with my suit and my rubber gloves on. As I went back to my office to put the numbers in an excel sheet, I realised I had locked myself out. Nobody was there, nobody could help me get in.

I knew the first few people were going to start coming in at 5am anyway, so I only had to wait for an hour. I started to sit on the ground and just think about the situation. I remember thinking to myself:

“What am I doing here? I just counted meat, I’m about to go write down the numbers in a spreadsheet, along with what the guests complaints were about their cocktails tonight.”

And I just had this moment of realisation where I was totally misaligned. I was really trying to convince myself that because I was doing something I thought I was passionate about in the food world, I deviated from doing investment banking or consulting like my friends were doing. I thought that because I was in food and restaurants I was going down my own path.

But in reality it was a corporate position that was more traditional and steadfast in its ways than if I had gone into consulting and investment banking.

So right then and there I said “I’ll quit tomorrow”. I talked to my parents and they tried to talk me out of it a little bit, but ultimately they fully supported the decision. So I went ahead and quit that story because there was a total misalignment between my personality, my views, my culture on one side, and the culture that was at this company on the other side.

On top of that, for a while I had been doing reflections on personal growth podcasts and books, and I churned all those reflections pretty quickly into my first book. I didn’t know what I was going to do next but I knew this:

  • I knew it had to add value to other people’s lives
  • I knew it had to be my own and I needed to create something
  • I knew I had to focus on building relationships, communicating, and soft skills

That’s what really works for me. So with those 3 things in mind I became an author, a coach, and a speaker.

What advice do you have for people who struggle to actually start working on the projects they have?

Take a couple hours to sit down and write out what your Cloud 9 journey would look like for this endeavour that you’re going on.

Actually walk yourself through the steps of success. Ask yourself:

“If I am successful, if I am living my dream life at the end of whatever it is that I’m pursuing, what does that look like at the end, in the middle, and in the beginning?”

Write down all those amazing steps. Write down all the hard work you’d have to put into it, all the behind the scenes work, all the hours. The accomplishments you’re going to have, the people you’re going to have to meet. Create that story of what your life is going to look like once you’ve accomplished all these amazing tasks in getting to where you want your project to go.

This process does 2 things.

1. It provides you with a sense of motivation.

2. It’s going to prove to you whether or not it’s actually worth it. It’s going to show you if you really want to go through that process of every single thing that needs to happen if you ultimately want your opportunity to become a reality.

If you could have a coffee and talk about anything with a personality (dead or alive) you admire, who would it be and why?

Even though I would drink tea with that person, I would say with Mitch Albom. He is my favourite writer, and he writes books in the way that I want to write books for the rest of my life.

They’re all stories, but they’re told through a lens of “how can we live the best lives possible?” In other words, what should we be focusing on in order to add value to others around us and create lives that are meaningful and purposeful for us and others? I’d love to talk to him about how he formulates his narrative, the research that goes into his books.

Aside from the professional talk, I would like to ask him questions about all the things he’s learned through his life. I want to ask him what he focuses on for living the best possible life he can.

How do your formulate and strategically navigate every single day to have the best possible day that you can?

How do you overcome some of the adversities involved with a long life that has so much fulfilment but maybe so much sorrow as well?

How do you keep pushing forward and know that the end result is so worthwhile?

I would talk about those big existential life questions with him. And then he’s a sports writer, so we would also talk about sports, football and things like that.

There you have it. I want to personally thank my guest for taking the time to provide me and my readers with really insightful answers. I am deeply grateful to Jordan Gross. Thanks a lot, all the best in your future projects!

And thanks to you for reading my content!

Subscribe to the newsletter

Every Saturday: 1 quote I believe in, summaries of my latest articles, 1 book/article I enjoy, my life metrics.

* = required field

Download The 168H Spreadsheet

The best time management tool, designed to clearly outline where your time is going and how you can optimise it. Get it for free today.


Share this article

Other posts you might like

Leave a Reply

Your email address will not be published. Required fields are marked *