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# S4E18: The Reluctant Entrepreneur - Tarot
- URL: https://crossstreetcoaching.com/s4e18-the-reluctant-entrepreneur-tarot/
- Published: 2023-02-06T12:00:00.000Z
- Updated: 2026-03-25T01:50:04.000Z
- Description: How can our Reluctant Entrepreneur keep learning?
- Author: Jacen Spector
- Tags: Podcast, Season 4, #podcast-episode, #imported, Entrepreneurship, Coaching

Season 4 wraps with something none of us expected: a tarot deck. Not the mystical kind. The Reluctant Entrepreneur Tarot is 22 cards built from the major lessons of this entire series, mapped onto the Major Arcana. Each card is a micro-lesson you can pull, reflect on, and revisit without reading anything cover to cover.

Diana explains how the project evolved from a book she couldn't finish into something tactile and nonlinear. Jacen connects it to Annie Murphy Paul's *The Extended Mind* and the idea that learning sticks better when it leaves the screen. They talk about how the cards work for people who are into tarot and people who aren't, why the lessons repeat on purpose, and how a Monopoly piece from a dollar store bag can teach you more about someone than a survey ever will.

This is the last episode of Season 4\. It's a good place to start if you want to understand what this series was about.

#### Listen to this episode

Also available on [Spotify](https://open.spotify.com/show/22cGas040PizW7dHvl69ip?ref=crossstreetcoaching.com) · [Apple Podcasts](https://podcasts.apple.com/us/podcast/cross-street-coaching/id1492768601?ref=crossstreetcoaching.com)

## In This Episode

- Why the Reluctant Entrepreneur became a tarot deck instead of a book
- The Major Arcana as a framework for entrepreneurial lessons
- How Diana uses the cards: one card per month, not a full spread
- Micro-lessons vs. linear learning and why short bursts stick
- The chess metaphor: same archetypes, different interpretations
- Choose-your-own-adventure format for business reflection
- Kinesthetic and visual learning as coaching tools
- Why scarcity as a card pull hit different in December
- The connection between *Listen!* and the tarot deck's design
- Behavioral economics, positive psychology, and why humans don't make rational decisions

## Timestamps

- **00:00** — Intro and the big reveal: it's a tarot deck
- **03:12** — Diana on why a book wasn't working and how the format evolved
- **07:45** — What the Major Arcana is and how 22 cards map to entrepreneur lessons
- **11:30** — Jacen's inner skeptic vs. the value of intentionally broad reflection tools
- **15:20** — How Diana actually uses the cards: quarterly and monthly pulls
- **19:00** — The scarcity card, the moon, and cycles of abundance
- **22:15** — Kinesthetic learning: dollar store objects, coaching games, and the Monopoly metaphor
- **26:40** — *The Extended Mind* and why gestures and physical objects expand intelligence
- **29:30** — Cards that repeat: when you shuffle and pull the same one back out
- **32:45** — The analyst's perspective: rabbit trails that pay off later
- **35:50** — Darkness in the entrepreneurial journey and the ebb-and-flow lesson
- **37:30** — Pre-order announcement and wrap

## Referenced in This Episode

### Books

- [The Extended Mind: The Power of Thinking Outside the Brain](https://amzn.to/3YsS1gx?ref=crossstreetcoaching.com) by Annie Murphy Paul — How the brain uses the body, environment, and other people to think beyond its own limits.

### Concepts

- [The Fool's Journey](https://www.spiritofchange.org/the-fools-journey/?ref=crossstreetcoaching.com) — The first 22 cards in a tarot deck (the Major Arcana). The cards in sequence tell a story of growth and transformational change.
- [Positive Psychology](https://www.psychologytoday.com/us/basics/positive-psychology?ref=crossstreetcoaching.com) — A branch of psychology focused on what's going right, capitalizing on strengths to build a meaningful life.

### Related Work

- [Listen! Mentor Coaching for Coaches](https://hawthorneunion.com/product/listen-mentor-coaching-for-coaches/?ref=crossstreetcoaching.com) — Diana and Jacen's first collaboration. Bite-size coaching lessons in a coffee table book format. The design DNA behind the tarot deck.
**Transcript** 

**Jacen:** Hello, everyone, and welcome back to another episode of Cross Street Coaching. This is a show about personal and professional development, business and leadership, all from a coach's point of view. We've been doing a series for the last year called The Reluctant Entrepreneur, which is our flavor of starting a business. It's not for people who were born into a family business or came upon money, or the people that said "I can never work a day in my life." It's for everyone else in between.

This will be episode 18\. We've done almost 12, 13, 14 hours of content spread over 18 episodes in a year. And Diana, do you want to tell us a little bit about what you have to show for all this hard work?

**Diana:** Well, you know, the other thing we're really good at is making visuals that help inspire people to learn. So with that — drum roll, please.

Interestingly enough, this is something I never thought I would say out loud as a business owner. If you told me a couple years ago that I would be on a podcast and then eventually a YouTube video, not only talking about being an entrepreneur, but also making reference to a tarot deck, I would say, "I'm sorry, crazy person. Please don't come any closer to me."

But as I was having a lot of trouble getting this out — the opportunity to be on the podcast with Jacen was awesome. And I also wanted to make something visual and compelling. Something that's been helpful for me in the past is that sometimes the answers we seek, especially at points of transition and change in our lives and business, aren't always rational or logical. I like kinesthetic learning. I like visual learning. I think it's good to have practice and space for our intuition.

So from all that, we've actually made a tarot deck. It's just the Major Arcana — 22 cards. And in the process of writing the descriptions, we've matched podcast episodes to continue the learning with what Jacen calls micro-lessons mapped on the Fool's Journey, or the entrepreneur's journey.

**Jacen:** A lot of the concepts we've been talking about are things you have to learn and relearn, especially in the environment of starting a business. As you progress through that journey, your viewpoints change. Your view and tolerance on risk changes as you start accepting it, understanding it, or processing it differently.

I really like the idea of a set of cards as something you can have and touch and mix up and revisit. A linear book doesn't necessarily provide that. I call them micro-lessons because this is very much a way of learning something in a very short period of time. It's akin to doing something analog that we've learned in a digital world.

**Diana:** From an education perspective, there's an advantage to things we can touch. There's an advantage to things we can see. What I like about tarot is that even though it has all this history and research, ultimately it's what the image evokes for you.

As we closed out the year with Hawthorne Union and the holiday, everyone picked a card based on their 2022\. Then everyone picked a card for their 2023\. It's fascinating to see what speaks to people from the imagery, from the words.

I like mapping new concepts on existing systems. The tarot has always been an interest, but I've never really understood it. I use it as a business forecast. What do I need to keep in mind this month? This quarter?

For December, I pulled the card that was scarcity. Scarcity in the tarot deck is matched to the moon — illusion and intuition. What can you see and what might not be what it seems. If you think about scarcity as a business concept and as a fear of an entrepreneur: it's a business tactic, but it can also be pervasive and daunting. If we think about it as a cycle, the moon becomes the sun, scarcity becomes abundance.

**Jacen:** If you're not familiar with tarot cards — what we've created is that rather than a book with chapter after chapter, we took the concepts from this podcast and changed the names of some tarot cards to represent different steps along an entrepreneur's journey. The cards don't have names like the Joker or the Fool. They're represented by events like risk, scarcity, investment.

Each card has visuals that are metaphorical. And we've got a little guidebook that recaps the lessons. It becomes a self-coaching tool for you to reflect and absorb a bit of self-directed learning.

**Diana:** My mom, who is our editor at Hawthorne Union, asked me: "Is this like *Listen!*, where you recommend reading cover to cover?" I said no. This is something where you pick a card and then read about that card. First you have your own reaction. What is it evoking for you? Then if you want to hit the guidebook, there's a paragraph from the reluctant entrepreneur perspective, a quote, a paragraph from the tarot perspective, and coaching questions to consider.

I used to love Choose Your Own Adventure. Really, instead of creating a book you read cover to cover, it's a way to pull a visual and then choose your own adventure with the material.

**Jacen:** I described this project to people who don't know tarot and loved the dual format. We're taking concepts that would normally be in a book but putting them in a nonlinear format. Not everyone's entrepreneur journey is going to be the same, but they have these crossroads.

**Diana:** So this is how I use it. Traditionally tarot has different spreads — past, present, future, mind, body, spirit. I do best when it's just: what's something I need to be aware of now, this week, this month?

For Q4, I pulled Executive Dashboard. Not surprising — looking at where's the money coming in, strategic decisions to close out Q4, what are we looking for in 2023? The November card was Partnership — leaning into partnership with Jacen and others, plus the structural elements. October was Perspective, because we got together as a team for the first time ever in person.

**Jacen:** One of the things I find is that when people engage with services like coaching, they see progress quickly because they've got a new commitment. But after three months, old ways start creeping back in. I enjoy this format because it keeps a bit of levity, a bit of newness, more staying power than just intensity followed by snapping back to old habits.

**Diana:** What's been interesting is that this process showed there was more learning for me to do. Even the description for Innovation — the idea that when we plant seeds in nature, it's not in our control what grows when and how much. There's a partnership where you can plant the seed and cultivate it, but what that's going to look like, especially when our work has creative, intuitive, physical, emotional elements — we have this sense of ourselves as rational, practical beings. But all behavioral economics shows that humans don't make rational decisions. We make emotional decisions.

My hope is that this podcast and the cards can help people look at things from a different perspective.

**Jacen:** I'm hoping that by being transparent about what we were doing and making it accessible, regardless of where you land on the intuitive scale, it's something you can tap into. Whether you use it like Diana does — as a theme to focus on — or as a coaching topic, a journaling prompt, or a bit of reflection.

**Diana:** Even if something here resonates in a negative way — "I would never do that" or "that doesn't appeal to me" — that's data too. Just be curious, have some fun with it. Sometimes we have positive responses, sometimes negative. We can learn from both.

**Jacen:** This is going to bring us to the end of our episode and the end of the season. The entrepreneurial journey can have a lot of darkness in it, and the whole concept of tarot is that the cards aren't just light or dark. There are lessons, ebbs and flows, ups and downs. We want to win all the time and be consistent all the time, but when you look at the archetypes, there are seasons of these things.

**Diana:** I hope something on this journey can be helpful. And I've learned that sometimes the paths that didn't yield what I thought was relevant were actually helpful later. If you go down rabbit trails trying to solve something, the next time you get presented with it, you've already done the work.

**Jacen:** As this podcast goes up, we should have pre-orders up. You can find us on LinkedIn and at [hawthorneunion.com](https://www.hawthorneunion.com/?ref=crossstreetcoaching.com). Thanks, everyone, for tuning in.