The Resignation Draft Loop—And a 30-Day Test to Calm It Down
Finding Clarity in the 8:22 a.m. L Train Scroll
You had a viral week and now your brain is acting like you have 48 hours to decide whether to quit your job—classic career pivot anxiety with extra FOMO.
Jordan showed up to my studio call from the most New York place imaginable: eight minutes early, AirPods in, still in work clothes, the kind of face that says they’ve been awake since before their alarm. They didn’t say “I’m stressed.” They didn’t have to.
They told me about 8:22 a.m. on a Wednesday, packed into the L train—phone screen warm from being held too long, flipping between their bank app, a Stripe dashboard, and a Notes page literally titled Resignation Draft. Fluorescent lights buzzing overhead. Someone’s coffee breath hanging in the air. Their thumb doing that tiny twitch-refresh like it was CPR.
“This week proved it can work,” Jordan said, eyes locked on their own screen. “But what if it was a fluke.”
They paused, then added, like they hated how true it sounded: “I don’t want to be dramatic. I want to be smart.”
What they were really asking wasn’t just go full-time or keep my 9–5? It was: If I choose wrong, am I going to be wrong in public? In a city where rent autopay is punctual and social media feels like a scoreboard, that fear lands in the body fast—like a tight chest that won’t quite open, a jaw that won’t unclench, a wired-but-tired buzz that keeps you staring at numbers at midnight as if the right spreadsheet cell could finally grant permission.
I let a beat of silence hold them, then I said, “Okay. We’re not going to use Tarot to predict the future. We’re going to use it the way I used decision frameworks on Wall Street: to see what your nervous system is doing, what each path really costs, and what a sane next move looks like. Let’s make you a map to clarity—not a verdict.”
Choosing the Compass: The Decision Cross Tarot Spread
I asked Jordan to take one slow breath and put their phone face down for sixty seconds—no drama, just a clean break in the loop. The tiny act looked almost painful, like setting down a weight you didn’t realize you were gripping.
“Today,” I told them, “we’ll use a spread called the Decision Cross.”
For readers who like to know how tarot works in real life: this spread is built for exactly this kind of career crossroads—go full-time on the side hustle vs keep the 9–5. It’s not an outcome-prediction machine. It’s a structure that forces the conversation to stay honest: what’s happening now, what Option A actually offers, what Option B truly provides (and costs), what factor matters most, and finally—how to move forward without forcing certainty.
I also like it because it creates a “third space.” It stops the reading from collapsing into an all-or-nothing fantasy. A Decision Cross can hold both impulses—the Explorer energy that wants freedom and the Builder energy that wants stability—and then translate them into something livable.
“Here’s what we’re doing,” I said, laying out the positions. “Card 1 is the current day-to-day reality—the actual juggle. Card 2 is Path A: going full-time. Card 3 is Path B: staying in the 9–5. Card 4 is the deciding factor—sustainability and timing. Card 5 is integration: the next step that turns paralysis into a plan.”
Reading the Map: Decision Cross Meanings in Context
Position 1: When “Being Responsible” Turns Into Tab-Switching Debt
I turned over the first card. “Now we’re looking at the card that represents your current situation and the concrete way the decision is showing up day-to-day.”
Two of Pentacles, reversed.
“This is the classic juggling card,” I said, “but reversed, it’s not a cute ‘I’m busy’ vibe. It’s overload. It’s dropped balls. It’s the moment your brain starts treating every notification like a fire drill.”
I pointed to the infinity-shaped ribbon looping around the pentacles, the bent knees, the ships getting tossed on choppy waves. “In modern life, this is: it’s 6:05 p.m., you’re still half in employee mode while your side hustle is blowing up in the background—Slack is pinging, your dashboard is open, and you keep switching between them like if you keep all plates spinning, you won’t have to choose. You feel busy every minute, but the day ends with nothing actually resolved—just a tighter chest.”
Jordan gave me that reaction I see all the time with this card: not a nod at first—an almost-laugh. A small, bitter sound that tried to be casual and failed. “That’s… kind of brutal,” they said. “Like, yes. That is literally my week.”
And I leaned into the echo I knew would land: “Tab-switching as coping. Slack/email. Dashboard. Resignation Draft. Refresh, refresh, refresh.” I watched their thumb twitch in midair as if it had muscle memory. “The inner deal your brain is making is: If it stays up, I’m allowed to dream. If it dips, I was irresponsible.”
I let the contrast land. “Motion versus progress. Busy versus chosen.”
The reversed energy here is a blockage: Earth energy (money, time, systems) is scattered instead of grounding. The decision feels impossible because exhaustion is steering. When you’re running on low battery mode all week, every option looks like a threat.
Jordan exhaled—quiet, involuntary. The kind of exhale that says, Oh. This is why I can’t think.
Position 2: The Blank Calendar Fantasy (and the Vertigo Under It)
“Now we’re looking at the card that represents Path A: what going full-time is really offering you psychologically and practically.”
The Fool, upright.
“This is a real beginning,” I told them. “It’s the part of you that wants to trust yourself without having to earn permission.”
I kept it concrete, because Jordan didn’t need a pep talk—they needed a clean translation. “In modern life, this is you picturing quitting and it feels like opening a blank Google Calendar where every hour is yours. It’s thrilling. But there’s vertigo too: there’s no built-in structure, no one assigning priorities, and on quiet-sales days you have to decide what ‘enough’ looks like.”
The Fool’s energy is expansion—but expansion can drift into chaos if it’s not tethered. The dog at the Fool’s heels isn’t a villain; it’s a nervous system. It yelps when you move too fast.
Jordan’s eyes softened for a second. “I want that,” they said, quietly. “Like… I want to wake up and not immediately be in someone else’s priorities.”
Position 3: The Direct Deposit Exhale (and the Fortress It Can Become)
“Now we’re looking at the card that represents Path B: what staying in the 9–5 is really providing—and costing—psychologically and practically.”
The Emperor, upright.
“This is structure,” I said. “Benefits. Predictable pay. A container that keeps the floor from moving under you.”
I tapped the stone throne and the armor. “In modern life: you look at your paycheck, your health insurance, the predictable rhythm of your 9–5—and your body instantly relaxes. Like, okay, I can breathe. That’s real.”
Then I added the part people don’t love hearing: “But it can also become a fortress. Not because the job is bad—because the identity of being ‘reliable’ becomes your armor. And armor keeps you safe, but it also keeps you from feeling your own hunger.”
Jordan swallowed, and I could see the split-screen montage play behind their eyes—the echo I wanted: one side, a blank calendar and a creative sprint; the other, a direct deposit notification and the health insurance portal. The inner line: I want to be brave. I want to be responsible.
“Golden handcuffs,” Jordan said, like they were trying the phrase on and realizing it fit.
“Exactly,” I said. “And there’s no moral high ground here. The question is: is this structure a foundation you’re using strategically, or is it a hiding place when the side hustle feels emotionally risky?”
Position 4: The Four Fridays Lens
“Now we’re looking at the card that represents the deciding factor to weigh: sustainability, timing, and what must be true before you shift.”
Seven of Pentacles, upright.
“This is the pause mid-harvest,” I said. “It’s not stopping. It’s evaluating.”
I watched Jordan’s shoulders rise, waiting for me to say something like quit or don’t quit. Instead I gave them what this card actually gives: a change in pace.
“Right now you’re living in hourly terms—ping, spike, lull, dread,” I said. “This card forces a zoom-out. Think: the next four Fridays. Not today’s dashboard.”
I contrasted it on purpose: “Notification ping versus a quiet spreadsheet review you do once a week with a cup of coffee and your phone across the room.”
Jordan blinked, like they’d been looking at a screen too long and suddenly remembered there was a window. I could almost feel their brain downshift. Their gaze unfocused for a second—the mental scroll-back—then returned steadier.
“Stop treating one good week like a lifetime verdict,” I said, using the simplest language I knew would stick. “Your next move doesn’t have to be dramatic—it has to be repeatable.”
The Seven of Pentacles energy is balance in Earth: grounded measurement. This is where the question becomes: how to know if side hustle income is sustainable—not by vibes, but by a small set of real numbers you can track.
Position 5: When Temperance Spoke—The Measured Mix
I let my hands hover over the last card for half a second longer than usual. The room felt quieter—not mystical, just psychologically different, the way a conference room goes silent right before someone says the thing everyone’s been avoiding.
“Now we’re looking at the card that represents integration and next step: how to move from paralysis into an aligned, actionable plan without forcing certainty.”
Temperance, upright.
The angel stood there, one foot on land, one in water, pouring steadily between two cups like it had all the time in the world. A path stretched toward a bright horizon that wasn’t screaming, just… there.
Setup: Jordan had been trying to make the anxiety disappear with one more data point—dashboard, bank app, Resignation Draft—like if they could just feel calm, then the “right” choice would reveal itself. But their body was already voting with a tight chest and midnight spreadsheets.
Delivery:
Not a frantic juggle or a cliff-jump—choose a measured mix, like Temperance pouring steadily between two cups.
Reinforcement: Jordan’s breath caught first—an actual, tiny freeze like their lungs forgot the next step. Their fingers hovered over their keyboard, then slowly curled into their palm, then opened again. Their eyes went glassy for a second, not from sadness exactly, but from the shock of relief—like someone just told them they could stop sprinting for thirty seconds without being disqualified. Their shoulders dropped, then they laughed once, softer this time. “So… I don’t have to send the resignation email like I’m jumping off a cliff,” they said, and their voice wobbled on the last word—equal parts permission and responsibility.
I nodded. “Set a 10-minute timer. Open a notes app and write two headers: ‘Hype metrics’ and ‘Sustainability metrics.’ Under Hype, list what spiked this week. Under Sustainability, pick just three numbers you can track weekly for 30 days—profit after expenses, repeat buyers/leads, hours worked. If your chest tightens and you start forecasting, stop early. Your only job today is to name what you’ll measure, not to decide your whole life.”
Then I asked, gently, “Now, with this new lens—can you think of one moment last week where a measured mix would’ve changed how you felt? Even by five percent?”
This is the pivot from wired, adrenaline-fueled choice paralysis into grounded, metrics-led confidence. Not certainty. Ownership. Temperance is self-leadership that doesn’t need an audience.
And here’s where my old life flickered in—an inner flashback I didn’t plan. I remembered the trading floor: the illusion that you can control uncertainty if you stare at the screen hard enough. You can’t. What you can do is define risk, set rules, and stop pretending emotion-free decisions exist. Temperance isn’t “calm.” It’s structure for volatility.
“In finance,” I told Jordan, “we don’t bet the firm on a feeling. We run scenarios and we size risk. This card is telling you to treat your career move the same way: not as one irreversible proof of worth, but as a paced experiment you can trust.”
The Temperance Transition Plan: Actionable Advice You Can Start This Week
I leaned back and connected the story the spread had been quietly telling the whole time.
“Here’s the arc,” I said. “The Two of Pentacles reversed is you trying to live with one foot on the office escalator and one foot on a moving sidewalk—working two jobs until everything feels urgent and nothing feels chosen. The Fool is the real desire for freedom and a new identity. The Emperor is the real need for a stable container—rent, benefits, and the pride of being dependable. The Seven of Pentacles is the missing lens: sustainability over hype. And Temperance is the answer you actually needed: you don’t have to choose between a cliff-jump and a cage. You design the blend.”
“Your cognitive blind spot,” I added, “is thinking you’ll trust yourself only after you have perfect data. If you need perfect data to trust yourself, you’ll stay stuck collecting proof forever.”
Then I shifted into what I do best—turning insight into a decision process you can actually execute. “I want to give you a simple framework I used in M&A,” I said, “but adapted for a human life. I call it my Risk-Reward Matrix meets Strategic Crossroads Analysis: three scenarios, probability-weighted. Not to predict. To stop your brain from treating every dip as doom and every spike as destiny.”
Jordan immediately tensed—an expected objection forming. “But I don’t have time for more analysis,” they said. “That’s… kind of the problem.”
I smiled, because that was the most honest resistance possible. “Exactly. So we’re doing less analysis, on a timer, and more reality-testing. We’re replacing endless forecasting with a repeatable rhythm.”
- The Weekly Reality Review (15 minutes, once)Pick one day/time you can repeat (example: Friday 6:30 p.m.). Set a 15-minute timer. Write down only three numbers from the past week: (1) profit after expenses, (2) hours spent, (3) repeat customers/leads. No forecasting. No “if this continues.” Just what happened.If your brain tries to spin a story, treat it like a Slack ping: notice it, don’t answer it. This is private data for you, not a performance.
- The Hard Stop Alarm (Temperance boundary, 4 nights)Set a “Hard Stop” alarm for side hustle work 4 nights this week (example: 10:30 p.m.). When it goes off, stop mid-task. Open Notes and write one line: “Next step starts here tomorrow.” Then close the laptop.If you panic—“momentum will die”—shorten it to a 2-night version. The point is to prove you can create rhythm, not grind until you break.
- The 30-Day Measured Mix Statement (one paragraph)Write one paragraph that starts with: “For the next 30 days, I am testing full-time viability by…” Include (a) the three metrics you’ll track weekly, (b) one constraint you’ll enforce no matter what (order cap, client response window, or content cap), and (c) a review date on your calendar when you’ll decide your next increment—day 30, not today.Keep it boring on purpose. A phased transition is still a decision. It’s just a decision you can live inside.
Jordan stared at the list, then said the most real thing they’d said all session: “But I can’t just stop at 10:30. My customers message late. And my 9–5 is already draining me. If I don’t answer, I’m scared I’ll lose them.”
That was the moment the “business question” turned back into the actual question: self-worth and control.
“Okay,” I said, keeping it practical. “Then don’t make the Hard Stop a silence. Make it a boundary.” I suggested a client response window they could pin everywhere: “I respond 12–6 p.m. ET, Monday–Friday.” Then I added my trading-floor pre-commitment ritual—the simplest version: “Before you open any dashboard, do one breath in, longer breath out, and ask: Am I refreshing for information, or for reassurance? If it’s reassurance, you stop. That’s not data. That’s cortisol.”
“Temperance isn’t asking you to be chill,” I reminded them. “It’s asking you to be deliberate. Choose metrics that measure sustainability, not adrenaline.”
A Week Later: Ownership, Not Certainty
A week after our session, I got a message from Jordan that was only two sentences long.
“Did the Hard Stop thing twice,” they wrote. “Hated it the first night. Slept six hours anyway.”
Then: “Also did the Weekly Reality Review—15 minutes. I didn’t quit. But I stopped checking Stripe in the deli line like it was a read receipt.”
It wasn’t fireworks. It was the first quiet proof of the real transformation: from adrenaline-fueled choice paralysis and self-worth pressure to grounded, metrics-led confidence in a paced next step. The decision didn’t have to be made in a single dramatic move. It could be made in increments Jordan could actually live inside.
And if I’m honest, that’s what I love most about Tarot when it’s done well: it doesn’t replace your agency—it returns it. It gives language to the pattern, then hands you a small lever you can pull today.
When your side hustle finally pops, it can feel like every hour is a referendum on whether you’re allowed to want more—so you keep juggling until your chest is tight, because choosing one thing feels like risking your whole identity.
If you didn’t have to “prove” your worth with one dramatic move, what would a 30-day, low-drama experiment look like—your own two cups, your own measured pour—that you’d actually trust?
