
Not a Money Person? You Can't Learn and Look Good at the Same Time
October 27, 2026
📝 Show Notes
AI disclosure: This episode is narrated by an AI-generated voice.
Maybe you've said it out loud. "I'm just not a money person." J. has a different explanation. Every person goes through four levels to learn anything, whether it is a stick shift or the numbers on a rental, and the second level is supposed to feel uncomfortable. J. taught it this way in his Cashflow Foundation course. You can't learn and look good at the same time.
What you'll learn:
- Why the person you are today isn't ready for the future you want yet, and why that's good news
- The four levels of learning, in plain English: you don't know what you don't know, you know you don't know, you know but have to concentrate, and the zone
- The three words that stop learning: "I know that"
- Why we stop asking questions somewhere between kindergarten and twelfth grade, and what a toddler learning to talk can teach you about money
- How the four levels show up when you start a rental business
- A 10-minute homework: one money topic you've avoided, your level, and one question to ask this week
Timestamps:
00:00 'I'm not a money person'
00:55 Who you are today vs. what you want
01:45 Level 1: you don't know what you don't know
02:41 Level 2: you can't learn and look good
04:02 Levels 3 and 4: from concentration to the zone
05:02 The four levels in a rental business
06:35 Your 10-minute homework: one question
07:24 Diagnostic call and sign-off
08:09 AI voice note
Want a second set of eyes on your situation and your numbers? Book your complimentary one-on-one diagnostic call: go.cashflowdiary.com/ep702-call
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Sources: J. Massey's own teaching. Cashflow Foundation course ("the four levels of learning," the photography and stick-shift examples, "I know that," the bedtime-story questions, decide means to cut off), a 2020 live training (the toddler learning to talk), a 2023 mastermind session ("an addiction to looking good"), and a 2023 member webinar ("you and I cannot out-earn our personal growth").
If this helped, rate the show on Apple Podcasts or Spotify.
Narrated with J. Massey's licensed AI voice, built from his own recordings.
Educational content, not financial advice. Results not typical; client details changed.
- (00:00) - 'I'm not a money person'
- (00:55) - Who you are today vs. what you want
- (01:45) - Level 1: you don't know what you don't know
- (02:40) - Level 2: you can't learn and look good
- (04:02) - Levels 3 and 4: from concentration to the zone
- (05:02) - The four levels in a rental business
- (06:34) - Your 10-minute homework: one question
- (07:24) - Diagnostic call and sign-off
- (08:09) - AI voice note
📄 Transcript
Full episode transcript available below.Download transcript →
Four. That's how many levels every person goes through to learn anything. Driving a car. Taking a picture.
And yes, money. Welcome back to the Cashflow Diary podcast. I'm J. Massey.
Maybe you've said it out loud. I'm just not a money person. Maybe the banking app sits on your phone with the red badge on it, because you don't want to see the number. Maybe somebody at work talks about their four oh one k match, or a rental they run, and you nod like you follow, and then you change the subject.
If that's you, I want to give you a different explanation. You might be standing on level two of something, and nobody ever told you level two is supposed to feel this way. Today I'll walk you through the four levels of learning, the way I've taught them in my courses for years. Then we'll look at how they show up when you start a rental business.
And I'll give you one small thing to do this week. In our Cashflow Foundation course I told people this. The person who you are today cannot obtain, own, or control the future that you want tomorrow. Who you are today isn't capable of it yet, because if you were, you would already have it.
That sounds harsh the first time you hear it. I meant it as good news. It means you're allowed to change. In fact, you have to.
And to change, you go through four levels of learning. You've been going through them your whole life. The trouble starts when you don't know you're in them, because that's when you quit. Think about a New Year's resolution.
I want to lose weight. I want to make more money. If yours didn't stick, in that course I said you probably quit because you weren't aware you were going through the four levels of learning. The hard part felt like proof you weren't cut out for it.
Level one is unconscious incompetence. That's a mouthful, so here's the plain version. You don't know what you don't know. I used photography as the example.
You see great pictures and you think, photography looks cool, let's do it. You don't know the difference between f-stop and ISO and shutter speed. You don't even know those words exist yet. Money works the same way.
Many of us learned one way to get money. Get a job, get paid, pay the bills. Nobody sat us down and talked about cash flow, or assets, or more than one way to earn a dollar. It's hard to be good at something nobody showed you.
There's a trap at this level too. In that course I called them dangerous words. Three of them. I know that.
The moment you say, I know that, you stop listening. You've heard of a budget. You've heard of real estate. I know that.
And the door closes on anything new somebody could show you. Level two is conscious incompetence. Now you know that you don't know. That's progress, even though it feels worse.
This is the level where you ask questions. I have three daughters and a son. When they were little and I was reading a bedtime story, they'd stop me at a word. Daddy, what does that word mean?
They knew they didn't know, so they asked. No embarrassment at all. Somewhere between kindergarten and twelfth grade, we lost that. We learned that if you raise your hand, you might look stupid.
So we stopped asking. And as adults we carry that right into our money. We don't ask what a Roth is. We don't ask the friend with the rentals how he got started.
We nod. I've said this in my courses, on live trainings, and in our mastermind. You cannot learn and look good at the same time. Think about a toddler learning to talk.
Do they sound good? Can you understand somebody else's toddler? You look at mom, and she says, oh, he wants cookies. That toddler doesn't care how it sounds.
They keep repeating it until they get what they want. Could you imagine if toddlers understood criticism and judgment? We'd never learn to speak. In one mastermind session I put it this way.
We have an addiction to looking good. That addiction keeps grown adults stuck on level two, too embarrassed to ask the one question that would move them to level three. Level three is conscious competence. You know what to do, but you have to concentrate to do it.
Remember learning to drive? Especially a stick shift. The first time you tried to take off, how smooth was it? Somebody in that car got whiplash.
And while you were learning, there was no music, no coffee, no phone. Windows up. Hands at ten and two. Check the mirrors.
Everybody be quiet. That's level three. You can do it, and it takes all your attention. Level four is unconscious competence.
Some people call it the zone. You get in the car and you don't think about the clutch. You go. It's like when somebody asks your name.
You had to learn your name once. Now you don't think about it. What gets you from three to four is repetition. In that course I said it takes time, and more than time, it takes commitment.
The word decide comes from a root that means to cut off. When you decide, you cut off the other options, and you stop keeping one foot out the door. So what does this look like if you're thinking about rentals? For me, the second stream came from rentals.
Mostly as an operator, through rental arbitrage. That means leasing a property with the owner's permission and renting it out furnished. A rental is a business. It takes work up front, it takes money, and it can lose money.
It's one way to build a stream, and it isn't the only way. This is education, not financial advice. The four levels show up here too. Level one, you see a listing that's booked every weekend and you think, I could do that.
You don't know about cleaning fees, slow months, permits, or the owner's permission yet. Level two, you find out. And it can feel like you're getting worse. This is the level where it's tempting to quit.
Your job here is to ask questions. Ask an operator. Ask the city. Ask the property owner.
Level three, you can run the numbers on a property, but it takes you a while with a calculator and a notepad. Your first call with a property owner is going to be clumsy. You'll forget a question. That's fine.
You can't learn and look good at the same time. Level four, you look at a property and you have a feel for whether the numbers work before you open the spreadsheet. That only comes from doing it over and over. And this applies to me too.
In a webinar a few years ago I told our members, you and I cannot out-earn our personal growth. If I want to earn more money, it requires me to become more than I currently am. I'm okay with that, which means I can't learn and look good at the same time either. Okay, here's your homework.
It takes about ten minutes. First, write down one money topic you've been avoiding because you might look dumb. Maybe it's your credit score. Maybe it's what a retirement account does.
Maybe it's how rentals work. Second, write which level you're on with it. One, two, three, or four. If you wrote two, good.
Two means you know what you don't know. Third, ask one question about it this week. Ask a person who knows. Out loud, or in a message.
Don't polish it. Then do what I told people in that course. Next time a friend asks, hey, how's that thing going, you've got an answer. I'm consciously incompetent, but I'm making progress.
Knowing the four levels helped me be more patient with myself, and it can do the same for you. Four levels. When you say, I'm not a money person, you might be describing level two. And level two is where the learning starts, as long as you keep asking.
If you'd like a second set of eyes on your situation, your numbers, and whether a rental business fits your next step... that's exactly what our complimentary one-on-one diagnostic call is for. com/diagnostic. And we'll look at it together.
Bring your questions, even the ones that feel basic. Okay, that's it for today. Write the topic, write your level, and ask one question. I'll see you on the next one.
I'm J. Massey. And this has been the Cashflow Diary podcast. If this helped, rate the show on Apple Podcasts or Spotify.
That helps another person find it. Quick note... this episode was voiced with my licensed AI voice, built from my own recordings.
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