Thinking Out Loud with Dean Jackson

Good morning.

1997, journal number four. By now I'm becoming a professional journaler. I'm really getting into this.

And since I started doing these videos, people keep asking me the same question. What do you actually do in your journal?

Turns out thirty-year-old me already answered it. There's a page in here where I made a list of the things to journal about.

So let's tally them up.

One. Snapshots of life, as it's happening.

That first journal is full of places I'd never been. Palm Springs. I read those descriptions now and I'm immediately back there. You're anchored to the moment.

This journal opens with the drive down to Florida. January. My friend Steve and I left in the most horrible snowstorm, a complete whiteout, 20-car pileups the whole way. We only got as far as Windsor the first night.

I'd forgotten all of it. It's right there on the page.

Not in a dear diary way... well, kind of in a dear diary way. Just the observations you make and the feelings you're feeling.

Thirty years from now, you're going to be thankful you took the time.

Two. Snapshots of the future.

Ultimate scenarios. Writing out a vignette of what it's going to look like when it's done.

My friend Cameron Herold calls it a vivid vision.

What's the picture on the cover of the puzzle box you're trying to put together?

Because the clearer you are on that, the more specific your mind gets about how to make it happen.

Three. Conversations with myself.

Most of the bulk pages in these journals are full dialogues. Me working something out on paper.

And it's the gift you get to enjoy twice. Once while you're doing it. Again thirty years later, when you get to see the way you were thinking.

Four. Mind maps, flowcharts, storyboards.

Visual planning.

I don't want to give it away yet, but there's a very special page coming in this journal. The very beginning of the 8 Profit Activators.

That came out of storyboarding. Flowcharting the process, spotting the benchmarks, then putting some creative thinking against them.

Five. Things that drive me crazy.

I love these one-question pages. Ask the question, then list 5 or 10 or more.

Then pay attention to what keeps recurring. And on your buffer days, come back to the list and ask what you could do to get rid of some of it.

Six. What do I want?

A future shopping list.

A Porsche 911 keeps presencing on mine around this time. Spoiler alert.

And you can point that question anywhere. What do I want in this situation? What do I want for my life? What do I want for my days?

Seven. How can I...

Fill in the blank.

Whenever you pose a question to your mind, you're immediately drawn to fill that vacuum with an answer.

You're querying your brain.

This is 1997, remember. We always referred to our brain as a search engine, and we didn't even know what a search engine was yet.

Eight. The idea machine.

Take one specific segment of the storyboard and get deep. Just ideas around that one piece.

Looking at the home buyer timeline, one of the questions I asked was, how could I create an opportunity for somebody to refer us before the end of the transaction?

Well... think about what's actually going on. Somebody moves into a new house, and for the next 30, 60, 90 days it's the first topic of conversation with everybody they know.

We got a new house. You have to come and see it. We're living over there now. We just moved.

Every conversation they're having is about this new vector in their life.

That's a great time for people to refer.

Nine. Things I've learned.

I read a lot. I've always read a lot. And I'm constantly processing it in the journal so I can distill the best parts of it.

Writing it out by hand reinforces it. And it lets me collide what I'm reading with everything else I'm reading.

The one-to-one future, crossed with the seven things people spend money on, crossed with real estate agents. That combination turned into something really valuable.

People also ask when to journal. It doesn't really matter. It just has to be an integrated habit.

I do it almost every morning. I've got a great environment for it. And I feel lost if I don't have my journal to keep writing things in.

I got a funny email from Rick the other day. Dean, question. Are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?

And I laughed to myself, because... yes. That's exactly what I do.

Here's what I really realized though.

Every idea I've ever had, and every dollar I've made over the last 30 years, went through my brain, through my pen, onto a piece of paper in my journal, before it ever went out into the real world.

So here's your nudge for today.

Pick one of the nine. Put it at the top of a blank page.

And just start.

Show notes: https://deanjackson.com/podcasts/tol/057-9-journal-prompts-for-thinking-through-anything/

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Good morning. This is the big day.

January 1997. Winter Haven, Florida. Journal number four, and the page where I move to Florida full time.

And here's something I wish I'd known thirty years ago.

Back then I was a kid in a candy store. So many possible businesses. So many markets. I always loved finding the edges of a thing... where are the boundaries, how big could this get.

I'd already worked out that there are only seven major things people spend money on.

Home. Cars. Food. Kids. Health. Money. Me.

Everything anybody spends money on fits into one of those seven.

So in the journal I gave myself a page per category, and filled it.

Under home alone: buying a home, renting one, the mortgage, the home inspection, furniture and accessories, electronics, painting the house, paint and wallpaper, carpet, carpet cleaning, garage doors...

That's the thing about a constraint. Put one on a brain that generates a lot of ideas, and it goes and finds everything that fills that bucket.

My ADHD brain loved it. Like a puppy in a field of fresh snow. Everywhere you run, it's untouched.

Then overlay all of it with the one-to-one future. Because the centerpiece of all seven of those is one person. One household. One relationship.

Infinite possibilities.

But here's the part I got wrong.

I spent a lot of time thinking about how big something could be... and a lot less time completing one of them.

Because time moves at the speed of reality. 60 minutes per hour.

Every word on that page had to come through my pencil one word at a time. I can't instantly finish anything.

Now think about Wayfair.

Before Wayfair was Wayfair, they didn't build Wayfair.

They built one complete e-commerce brand that sold bar stools. Only bar stools. Site, infrastructure, all of it, up and running.

Then grandfather clocks. Then ottomans. Then speaker racks. Every category with enough in it to be a big thing on its own.

270 individually profitable brands. Then they rolled them all up and... tada. Wayfair, with everything already built out.

That's the advice I'd give thirty-year-old me.

Instead of thinking about the vastness, think about the depth.

Take one. Build it all the way out. Let it run. Then take the next one.

From the base up, not from the top down.

Because I'd been living in the future for so long, imagining the whole finished thing, that working in the present felt slow. Almost like living in the past.

But your brain doesn't really care what it's working on... as long as it's clear on what it's working on. You get to innovate and imagine inside the one thing you're focused on right now.

So picture where I'd be if I'd taken one of them and built it all the way out. Then another one the next quarter. For thirty years.

That's 120 of them. Done.

That's a very different world.

And here's your nudge for today.

Take one of the things you've been imagining in full... and build it all the way to done.

Show notes: https://deanjackson.com/podcasts/tol/056-think-big-start-small-keep-going/

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Good morning.

Forty days and forty nights we've been doing these journals.

And the timing on this one is perfect. We're at the end of December 1996, just about to turn into 1997... and I still can't quite believe we've gotten forty episodes out of a single year.

Doing this has felt like time travel.

I'm reading pages I wrote at thirty. I've just turned sixty. And here's the strange part.

I feel exactly the same.

Same reactions. Same core nature. Nothing about who I am has really moved.

There's no internet in these pages yet. I haven't met most of the key people in my life yet.

But the seeds are all in there.

So before we open journal number four, let me pull out the three things I'd tell you to start today.

Number one. Start the journal.

April of 1996, journal number one. Of everything I've done, that decision has been the greatest gift.

I kept pretty good notes, and that's the whole trick. I read a page and I'm immediately transported back to where I was and what was going on.

Your 2056 self will thank you for starting in 2026.

Number two. Have the dialogue with yourself.

Most of what fills these pages is me talking to me. Thinking about my thinking.

We're pretty smart, you know. Our intuition is right more often than we give it credit for. If we just dig into it and explore it on paper, we come to pretty good conclusions.

I can see hunches brewing in these pages that turned into everything.

There's one coming up in 1997 I can't wait to show you. A question written at the top of the page... what am I going to do about the internet?

The pages are also where I try out my life. The architecture of the days. Lifestyle design, before I had a name for it.

I'd just moved to Florida. Wake up, go for a walk, come home, make some breakfast... and then watch Regis and Kathy Lee.

There was one segment where they followed Regis around for a day. He lived right across the street from the studio. Coffee with Joy, got dressed at home in whatever he was wearing that day, walked over.

Music comes on. And he spends the first ten minutes of the show just recounting everything he'd been doing.

Live on television. The rest of it was just being Regis.

That stuck with me. Because at sixty, what I'm completely bought into is just being Dean Jackson.

Look at my Facebook bio. I'm Dean Jackson. Period. Professionally, period. That's the whole thing.

And that gives me room to do whatever it is I want to do.

There's never been a better moment to just be you. Look at the reach you have now. The community. The options sitting there for the taking. We had none of that in 1996.

Number three. Go a mile deep on one thing.

The biggest impact I've ever had came from marketing and real estate. And these journals are filled with me playing the same game over and over, getting better and better at the micro elements of it.

Then I paired it with Michael Gerber's idea. Build the thing as though you're going to duplicate it five thousand times. Extraordinary results with ordinary people. Systems somebody can plug straight into.

Once I got bit by that bug, that was it. Thirty years of continual practice on the same thing.

That's the whole compounding secret and it isn't complicated. One thing. A long time.

Next up is journal number four. 1997. The transition to Florida.

So let's have a simultaneous sip, to toast the first forty days and forty nights.

And here's your nudge for today.

Get a notebook, and put one page in it... a dialogue with yourself about the thing you can't stop thinking about.

Then keep it for thirty years.

Show notes: https://deanjackson.com/podcasts/tol/055-3-things-your-future-self-will-thank-you-for-starting-today/

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Good morning.

Do free recorded messages still work today?

I keep landing on this as I go back through my journals. Circa 1996, that's what we had. Hardly anybody had a website. The ones that existed were cumbersome to build, and most people weren't in the habit of going to them anyway.

But we all had phones. And back then, phones were phones. No distraction.

That's the part I've been thinking about. A recorded message is an immersive focusing device.

Whatever we were doing to generate leads... ads, postcards, any of it... the one thing that got the most people to respond was call and listen to a free recorded message.

Because we had caller ID. And if the offer was call and talk to somebody, nobody wanted to do that.

Those three words made it safe. Free recorded message. You could get the information without feeling like you were about to be sold something.

Eban and I used to make ridiculous infomercials using all the anti-language. Call now, trained salespeople are standing by 24 hours and will rush your auto-debit commitment contract.

We were joking. But the fear was real. And it's still real. Nobody wants to talk to anybody now. Even a phone call feels like an intrusion... just text me, right?

So let's go into the tickle trunk. 1996. The Julie Matthews box.

We were getting busy. Lots of leads, one realtor, no help.

And you know the Michael Gerber idea... treat your business like something you're going to duplicate 5,000 times. Systemize the routine.

So we built a recorded message system for finding and hiring an assistant.

A little classified in the help wanted section, because the newspaper was still how you reached people. Winter Haven busy realtor needs part-time assistant, flexible hours. Free recorded message. And a phone number.

Here's how the actual message opened.

Thank you for calling. My name is Julie Matthews and I'm a realtor with Brokers Realty in Winter Haven. This message is about 2 to 3 minutes long and I've recorded it to do three things.

First, to tell you what the ideal candidate for this position would be like. Second, to give you an idea of what you'll be doing if we decide to work together. And third, to tell you what to do next if this sounds like a match for you.

Read that again and picture it as a landing page with a video today. Same message. Same three promises, right out of the gate.

Then we described the person. Organized. Pays attention to detail. Likes to implement systems for routine tasks. Able to work unsupervised. A caring person who can treat clients like royalty.

Reading it back now, there are probably a few HR violations in there...

Then what they'd actually be doing. Setting up appointments with other offices. Picking up keys, because not everything was on a lockbox yet. Preparing the file, returning the keys, updating the file.

And helping build a practice aimed at a wow experience and lifetime relationships, not just transactions.

Then what to do next. Leave your name, your mailing address, your phone number, and your email address if you have one.

As my friend Terry Hunnefeld would say, that's a sifting and sorting tool. Terry founded the Gold Rush system and took recorded messages to a whole other level in the '90s. I learned a lot from him.

Then the package went out. A photo of Julie. A transcript of the message they'd just heard, so they could read it back and check it still sounded like a match. An application form. A resume request. A stamped return envelope.

And a calendar, with instructions to highlight the hours they'd be available to work... and a highlighter in the envelope to do it with.

Now here's what all of that is really doing.

Half of it conveys the information. The other half sorts for the people who can follow directions.

The ones who sent everything back, complete, got invited to a career night. All of them at the same time.

The message can be a video on a landing page now. That part's easy.

What hasn't changed is the immersive, focused attention. One perfect version of the thing you want to say, cloned, with no distractions, and no saying it one at a time to everybody who calls.

So do recorded messages still work?

They sure do.

So here's your nudge for today.

Take the thing you explain over and over to every new person... and record it once, properly.

Then send people to the recording instead of your calendar.

Show notes: https://deanjackson.com/podcasts/tol/054-do-old-school-free-recorded-messages-still-work-today/

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Good morning.

I brought some props with me today.

I called it my tickle trunk, the way you say something you assume everybody knows... and I was today years old when I found out not everybody grew up with Mr. Dressup. My Canadian friends will know exactly what I mean.

I keep red archival boxes. Dozens of them. Every project I've done over my whole career, sitting in those boxes.

And this morning I've been in journal number three again. We're at the end of 1996, moving into 1997.

I'd talked in an earlier video about recorded messages... those three magic words, free recorded message. And somebody left a comment saying, oh yeah, those were the good old days. They used to send 20,000 postcards a week with nothing but a call to action to hear a 90-second message.

Here's what I thought when I read that.

These are the good old days.

Because looking back at what we had to work with, the thing that made it all so good was the constraint. Constraints force your creativity.

Print or direct mail. That was the entire menu.

I found the original guide to Winter Haven in the box. Same logo as the guide to Halton Hills I'd made a couple of years earlier, the one that became Toronto and Beyond. Eleven by seventeen, folded down to letter size. A little letter inside from a very young Julie Matthews, circa 1996.

We even put a price legend in it so I wouldn't have to reinvent the whole guide every time the market moved. Just shift the categories.

And every bit of it was laid out by hand. Pasted-up photographs. This is right before real desktop publishing. Getting one of those printed and out into the world was an effort.

But every single one of them pointed at the same thing. Call and listen to a free recorded message.

That was the lowest friction way for somebody to get information without feeling like they had to talk to a real person. And it took the burden off you having to be sitting there to answer the phone every time.

Then came the postcards.

Any time Julie got a new listing, that was an opportunity. We'd mail the neighborhood around that home.

And we didn't send a picture of the house. We told the story.

Do you know what your neighbors at 365 East Thelma Street did last night? It may come as a surprise to you, but they've been plotting for a long time.

Then the whole thing unfolds. They've decided to sell. They listed with Julie because they saw how fast she'd been selling homes around there. Three bedrooms, two baths, pool, almost 3,000 square feet, a family room that measures 30 by 30. Sits on a double lot running all the way from Thelma to Echo, deeded separately, you could build another home on it.

If you know anyone thinking of buying in East Lake Alfred, be sure to tell them about this one.

And the PS. If you're going to sell your own home in the next six months, Julie has a special report called How to Sell Your House for Top Dollar Fast. Call 1-800 whatever, 24 hours, for a free recorded message.

Run that card through the seven-step checklist. Single target market? Yes, the neighbors of that listing. Headline that draws you in? You know what it's about from the first line. Conversational language? It reads like news, not like an ad.

The just sold cards worked the same way. Your neighbor Mrs. O'Brien got exactly what she deserved... and it could happen to you next.

Then we tell you what she deserved. A buyer for her beautiful home, less than 90 days after she put it on the market.

Here's the test I'd use on any of it.

Would you hire somebody to stand at that person's doorstep and say out loud what you've put on your postcard?

You'd never. Most realtors are mailing a big photo of the property, the words JUST SOLD, a logo, a name, and call Julie and start packing.

But a story is a very compelling thing to find in your mailbox.

My favorite proof of that. One of the first times we mailed those cards, Julie got a call from the mailman who'd been delivering them. He'd read one, written the number down, and called her because he wanted her to sell his house.

He and his new girlfriend both had homes to sell, and they bought one together. Three transactions. From the guy carrying the mail.

And none of this is nostalgia, that's the part I want you to hear.

These are still the same postcards we use. To this day. The message is still as relevant as it was in 1996.

We did it for the Mosquito Authority. Your neighbors the Valentes got exactly what they deserved... and it could happen to you next. Then the story about the Valentes getting their yard treated and having a mosquito-free backyard. On the back, the offer. Absolutely positively no mosquitoes in your yard, guaranteed. Period.

And people still call the recorded message.

So do recorded messages still work today? Absolutely.

Do postcards still work today? Absolutely.

They're at the core of any message you want to put in front of a very specific group of people.

The only thing that's really changed in 30 years is that now we can put a QR code on the card next to those same words. More ways for somebody to respond. Same message doing the work.

So here's your nudge for today.

Take the last thing you mailed or emailed to your people, and read it out loud at an imaginary doorstep.

If you'd be embarrassed to say it... go and write the story version instead.

Show notes: https://deanjackson.com/podcasts/tol/053-good-marketing-never-gets-old-proof-inside/

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Good morning.

If you're growing your business, you're going to involve other people.

And once other people are involved... things are going to go wrong sometimes.

The real question is whether everybody already knows what to do when they do.

I was looking through journal number three this morning and found a page from Steve Kross.

Steve was a Century 21 broker in New Jersey. Ran a very successful office. He'd come and speak at the big seminars I was doing around the country with Joe Stumpf.

A gentleman in every way. And full of wisdom about how to handle the business.

He used to tell a story about a Kentucky Fried Chicken.

An older gentleman had been coming in every week for a long time. Same order every time.

Then one day the counter is busy, the cashier is brand new, and what this man always got was a little outside the way things are normally done.

So the new employee goes by the book. Says no.

And has no idea he just made a $5,000 mistake. Because alienating your best customer is never a small thing... it just never shows up on the receipt.

That's why Steve had three questions. If everybody in the organization is aligned around them, everybody knows what matters in the moment.

Question one. From the customer's point of view, am I treating this customer with the utmost respect?

Not taking a hard line. Not flexing authority. Not because I said so, or that's not how we do it here.

Question two. Am I exceeding the customer's expectation?

When somebody comes to you with a complaint, they're already carrying an expectation of how this is going to go. Usually not a good one.

And if you lean into it, you're feeding exactly the thing they were braced for. The divide grows... in front of them, and in front of everybody else who's watching.

Question three. Is what I'm doing in the best long-term interest of the customer?

Sometimes that means making a concession you didn't have to make.

And sometimes it means letting a customer go. That can be the long-term interest too.

They say people might not remember what you said, but they remember how you made them feel.

I've passed this page a few times now in journal three. And every time, I remember how it felt to come at things that way. Resolving instead of defending.

The other use for the three questions is afterward.

Somebody on your team has been through a conflict. Sit down together and walk the checklist. Did we treat them with the utmost respect? Did we exceed what they expected? Was it in their long-term best interest?

That's how a team ends up with one unified way of handling things, instead of three people handling it three different ways.

So here's your nudge for today.

Take the last time something went wrong with one of your customers... and run it back through the three questions.

You'll know pretty quickly whether you handled it, or just survived it.

Show notes: https://deanjackson.com/podcasts/tol/052-how-to-know-what-to-do-when-something-goes-wrong-with-a-customer/

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Good morning.

Journal number three. And it keeps happening... I'm reading pages from 30 years ago and finding the exact things I still do today.

One pattern shows up more than any other. Storyboards.

I've mentioned them before. But what I'm seeing now is what they really are. A focusing tool.

Here's the whole trick. Put a pen in your hand. Put a piece of paper in front of you. Write one instruction across the top.

And your mind has no choice. The pen forces you to think about only that thing. It gives your thoughts somewhere to go... out of your head and onto the page.

Page 111. The thing I was working out was a storyboard I called the seven-phase buyer wow cycle.

The magic is in breaking the journey into its segments. Where does somebody actually start? Where do they cross into the next stage?

Think about this cafe I'm sitting in. Lay out the whole experience through the eyes of a first-timer. The parking lot. The door. Walking in. Where do their eyes go? What are they looking for?

How do you make it so nobody feels out of place or confused? Because being a regular somewhere is a completely different feeling than your first time.

And that's the hard part. We're too close to our own thing. We know what it's supposed to be, so we can't see it fresh anymore.

Getting into the eyes of a brand-new person takes some creativity. Identifying the segments is what unlocks it.

So phase one of the buyer wow cycle... find someone looking for a home, and be so helpful they want to meet with you. That's the whole Before Unit, really. The eight profit activators are just this same storyboard, laid out as a timeline.

Then the appointment. What has to happen for them to feel secure with you? Then you go out and look at homes. Every one of these phases is full of little places to create a wow.

Take phase four. The conditional period. They found the home, the offer's accepted, and now you're removing conditions. For someone who's never done it, that stretch is nerve-wracking. Precarious.

So how do you create a wow right there? A daily check-in call. Getting the inspection booked. Pushing the mortgage approval along. Once you can see what the moments are, you can turn each one into a process.

That's the thing I keep coming back to. Look at the experience someone goes through with you. Find the benchmarks. Think of them like the locks in a waterway... each one lifts you to the next level.

What triggers the entry into a phase? How do you create a wow while they're in it? What's the exit into the next one?

Every page in the journal is a chance to walk it through. Tell the story to yourself. Imagine the ultimate version. Describe it from the buyer's side. Then isolate the pieces that need to be built or systemized to make it real.

That's a lot of what journal number three was for me. Laying these experiences out, one page at a time.

Because here's the truth underneath all of it. Every idea I've had, every dollar I've made in 30 years, went through my brain, down my pen, onto a page in my journal... before it ever went out into the world.

So here's your nudge for today.

Pick one experience somebody has with you. Walk it, box by box, through the eyes of a first-timer.

And find the one place you could turn into a wow.

Show notes: https://deanjackson.com/podcasts/tol/051-wow-experiences-dont-happen-by-accident/

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Good morning.

We're almost halfway through journal number three.

And I keep noticing the same thing on these pages... my undiagnosed ADHD, rearing its head, trying to work out why I can't seem to be a normal boy.

The question sitting underneath all of it. Why doesn't time management ever actually work?

I found nine reasons. So here they are.

One. We don't know what we want. My decider is broken. Every option feels equally possible, all at once, and I freeze on choosing one. So I run elimination tournaments... eight things in a bracket like the NCAA, played off against each other until one is left standing. Then I can finally focus.

Two. We don't put first things first. I drift to whatever's newest and most interesting, not the thing I already know matters. Nothing moves for me until it becomes a deadline. I love them and hate them at the same time.

Three. We focus on the wrong time frame. Time moves at the speed of reality... 60 minutes an hour, no matter how fast my head insists it's already done. The only actionable time frame is today. A thousand waking minutes. And really, the next 100. I run the day in ten-minute blocks, and you'd be amazed what fits in one of them.

Four. We don't leverage our time. Jay Conrad Levinson's 90-minute hour. If something takes 30 minutes and you can do something else alongside it, you've stretched the hour. Go for the walk and listen to the podcast. Stack it, batch it, multiply it.

Five. We don't allow ourselves to be supported. Michael Gerber's point. As we grow we cling to the things we think only we can do. The real move is to look at your pile and ask... is there anything here somebody else could do for me?

Six. We don't have systems for the routine. If you keep hitting the same snag again and again, that's time debt piling up. So I put a garbage can right outside the car door in the garage, and the junk on the passenger seat never makes it into the house. A bowl by the front door for the keys I always lost. Little systems, made easy.

Seven. We are in time debt. All the things you've been putting off weigh on you exactly like financial debt. So make the list. What do I owe, and to whom? Then run a time-debt snowball, Dave Ramsey style... knock off the fastest one first, feel the progress, keep going.

Eight. We don't have the energy. Procrastinating is exhausting. A block on the calendar is worthless if you're too drained to use it. That's why I've become what Brian Johnson calls a professional sleeper.

Nine. We are afraid. Afraid to set the big goal. Afraid of what taking action might mean. Afraid of failing. So we quietly shrink the whole thing down.

Here's a side note that surprised me. Almost everything I feel real pressure about involves somebody else. Someone's waiting, someone's expecting it. I never seem to feel that pressure just from myself.

And that's the fun of a journal. Nine reasons, sitting on one page of book number three, still explaining my whole week 30 years later.

I got a funny email from Rick the other day. "Dean, are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?"

I laughed. Because... yes. That's exactly what I do.

Every idea I've had, every dollar I've made in 30 years, went through my brain, down my pen, onto a page in my journal, before it ever went out into the world.

So here's your nudge for today.

Take the thing you keep putting off... and just ask what happens if you don't touch it in the next 100 minutes.

That one question tells you what actually matters.

Show notes: https://deanjackson.com/podcasts/tol/050-9-reasons-time-management-fails-your-entrepreneurial-adhd-brain/

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Good morning.

The last week of November, 1996. My very first Strategic Coach workshop in Toronto.

That's the day Dan Sullivan started me on a 30-year habit he calls thinking about your thinking.

I'm looking back at the notes I took in that first room. An industrial part of the city, beautiful old brick buildings, lofty loft spaces. Everything about it was built to make you think bigger.

And on day one, Dan laid out something I still run my whole life by. He calls it the entrepreneurial time system.

The idea is that an entrepreneur's time works like an athlete's or an entertainer's. You've got game days, practice days and off days.

Dan renames them. Focus days, free days and buffer days.

Focus days are easy to picture. They're the days you do the money-getting thing. Workshops, clients, coaching, whatever you actually get paid for.

Free days are the ones most people get wrong. Dan means a full 24 hours completely disconnected from work. Not slipping out at lunch for a movie and feeling like you got away with something. The day off is the whole point of the day.

Mine evolved into what I call super happy fun days. You orchestrate the whole thing, start to finish, filled with the stuff you love. Breakfast at your favorite place. A round of golf with a good friend. Lunch at the club. A movie. Dinner. A spa. All in one day.

But a day like that doesn't happen by accident. And that's where the underrated one comes in.

The buffer day.

I used to treat buffer days as the junk drawer of the week. The in-between. Catch up, do whatever's left over, whatever needs doing.

I had it backwards. The buffer day is the power move.

A buffer day is where you proactively plan and set up your focus days and your free days so they actually land. It's where the thinking about your thinking happens.

That's why I spend so much time in my journals. I'm sitting on a buffer day, drawing out the things I'll do on my focus days and lining up the things I want on my free days.

One thing I love to do is make a list of 26 things that bring me joy. There's no magic to 26. It's just the number of lines on a page in my journal.

Put a constraint on it and your brain gets to work. It does what you ask it to do.

Now that list is a menu. On a buffer day you pick from it, put it on the calendar, and enroll the people you want there with you. That gives everybody something to look forward to.

If you want an on-ramp to all this, don't try to build your perfect week this week.

Treat your calendar like the weather forecast.

You're a storm of activity moving through the days. You know exactly what today and tomorrow hold, same as a meteorologist knows the next couple of days cold.

But go out 14 days and it opens up. Pick three Tuesdays from now and it's easy to drop a beacon in there. A super happy fun day. A real buffer day. Once it's on the calendar, everything else works around it.

My friend Taki Moore calls it spanxing your calendar. Squeeze all your focus days into Tuesday, Wednesday and Thursday, and let the rest breathe.

I got a funny email from Rick the other day. "Dean, are you saying you can teach me to make fat stacks by hanging out at a pub drinking coffee like you?"

I laughed, because... yes. That's exactly what I do.

Every idea I've had and every dollar I've made in 30 years went through my brain, down my pen, onto a page in my journal, before it ever went out into the world.

So here's your nudge for today.

Stop treating the buffer day like a throwaway.

Give it a job. Use it to plan the days that actually matter... and watch how much better the rest of your week gets.

Show notes: https://deanjackson.com/podcasts/tol/049-the-most-underrated-day-in-your-week/

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Good morning. Day 33 out here.

I opened the journal this morning to a page titled “Eben’s brilliant idea number 1009.”

That number tells you everything. We weren’t precious about these. We were just riffing.

This was 1996. Eben Pagan and I were flying all over the country doing real estate seminars, and in between we were flexing our creative wings. Book ideas. Business ideas. Just to see what we could come up with.

Almost none of them came into the world. And that was never the point.

The point was the exercise. Letting yourself think about something with no constraint... without censoring the idea before it’s even finished.

Because every so often, one of those throwaway riffs turns out to be a seed.

Here’s one. Popular psychology says you can’t change other people, only yourself. So we took the opposite side. How to Change the One You Love.

I can see now that was the seed of Stop Your Divorce. And a book I did with a hypnotist called Hypnotize Your Husband. Same thread running underneath... we all quietly want to change somebody else’s behavior.

We even mapped out how the book could write itself. Ask a hundred women the one thing they’d change about their husband. Then hand the answers to a panel of professional change agents... a dog trainer, a lawyer, a drill sergeant, a priest, a hypnotist. In your professional opinion, how would you change this behavior?

A cartoon for each one. Graphic, a little satirical. The kind of book people buy as a gift.

Because that’s the real lesson sitting underneath it. It’s not always the best book that wins. Sometimes it’s the most provocative one.

Look at Mark Manson’s The Subtle Art of Not Giving a F***. Almost all of that success is the title. There are twenty books with more useful information inside... presented in a way nobody picks up.

Then there was the Tube of Joy.

We were sitting in an airport and sketched out a kiosk of nice tubes you could give as a gift. A golf tube with balls, tees and a towel. A tennis tube with grips and a magazine. A wedding tube, a baby tube, a birthday tube.

Impulse gifts, right there the moment you need one.

None of it happened. But the engineering drawings are still right here in the journal, and the fun of it was the whole reward.

It’s like a band jamming. You’re not trying to write the hit. You’re just playing... and now and then, out of the noise, comes the seed of something real.

So that’s your nudge for today.

Let your mind go. Ask “what if” with no constraints on yourself.

Some ideas are worth having even if they never happen. And once in a while... one of them turns into something.

Show notes: https://deanjackson.com/podcasts/tol/048-some-ideas-are-worth-having-even-if-they-never-happen/

Join me live on the next free 50-Minute Profit Finder call: 50minuteprofitfinder.com/podcast