Thinking Out Loud with Dean Jackson

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**Thinking Out Loud with Dean Jackson**

Dean Jackson thinks out loud about marketing, referrals, positioning, and the small ideas that quietly change how a business grows. Short, unscripted episodes. The raw thinking behind BreakthroughDNA and the 8 Profit Activators.

Latest Episodes:

“Imagine if you applied your SELF…” (Here’s how) Oct 13, 2026

Show notes

Good morning.

I'm reading journal number eight. The end of 1997.

And one of the most common themes I keep seeing is how to get myself to do the things I want to do.

When my mother passed in 2013, I found a red box with every report card from my whole school career.

And there was one comment that summed up all the others.

"Dean is able to achieve excellent results with what seems like little effort. Imagine if he applied himself."

I can still see Mrs. Jefferson writing that on my third-grade report card.

Those words have been sitting in my brain ever since.

I knew stuff. Anything I had to figure out on the fly in class, I was really good at.

But homework... that was a real burden.

And there I was at 31, still struggling with the same thing.

It's only in the last few years that I've really started embracing my ADHD. Not as a character flaw.

Russell Barkley calls it a disability. You can know everything, and you just don't do it.

That's not something you fix with willpower, or thinking differently, or affirmations.

Acknowledging it lets you build scaffolding. Support.

So I started breaking down those words. Because the clues are in the words.

The words are the formula.

Imagine.

As kids, anything's possible. As adults, we temper it. "That's not realistic."

But imagination is a big part of this. What would you really want, if you could count on you to make it real?

If.

If what you imagined were going to be real, what would have to happen?

That's the beginning of Dan Sullivan's Strategy Circle... your brain comes up with the obstacles, and you turn each one into an action.

You.

This is where things get blocked. It's the boundary between the imaginary world and the applied world.

And for me, what's in the way always comes down to one of three problems.

A logic problem. It doesn't make sense.

A logistics problem. You know what to do, you just can't get the action taken.

Or a limbic problem. The internal game. For me that shows up as indecision... way too many options.

As visionaries, we can draw the blueprints. We just can't swing the hammer.

Applied means making something real. In the real world, in real time, with something you can point to.

And here's the part that changed everything for me.

We hear "yourself" as one word, and it feels like a finger pointed at you.

What if you separated your and self?

Your SELF is something you have.

S is your sphere. Someone you know, or a service that's available, that can do the thing.

E is your energy. The things only you can do.

L is leadership. Is there someone you can just tell what you want, and they make it happen? That's the beginning of Who Not How.

F is finances. Can you just buy the outcome?

That's what has changed my productivity. I describe what I want, and my team creates it.

Like I said about Quentin Tarantino yesterday... it's not your job to know how to do all of those things.

So if you've heard "imagine if you applied yourself" and used it to blame yourself, it's probably because you're reading yourself as one word.

Dream it. Imagine it. Think through what would have to take place.

Then decide what to do first... by applying your sphere, your energy, your leadership, or your finances.

Show notes: https://deanjackson.com/podcasts/tol/132-imagine-if-you-applied-your-self-heres-how/

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

“That’s not your job.” Just do this… Oct 12, 2026

Show notes

Good morning.

We've been talking about overcoming obstacles.

And I love Dan Sullivan's first question... "Is there any way I could get this without doing anything?"

It reminded me of an interview I saw with Quentin Tarantino on the Charlie Rose show.

He was describing a lunch with one of his hero directors, Terry Gilliam.

Quentin was a new filmmaker, just getting started. He was at Sundance.

And he asked Terry Gilliam, "How do you get your vision up on the screen?"

He was asking about the technical things. Maybe there was some secret.

And Terry Gilliam said, "First of all, that's not your job."

As soon as I heard that, I thought... that's really interesting.

You can hire the very best cinematographers. Lighting directors who know how to get the lighting just right.

The best sound people. Costume and set decorators to make everything work out for you.

Your number one job, your only job, is to describe your vision.

As entrepreneurs, sometimes the biggest thing that gets in our way is the feeling that we have to do everything.

Back in 1997, when I was writing in my journal, we had email and the telephone. That was really it.

Fast forward to right now, and there's never been a better time to actually do nothing.

If you're a visionary, if you know what you want, your access to people who can do the things you need done is unprecedented.

And with what's coming with AI... any technical thing, any research, anything that requires opposable thumbs is available to us.

So your number one job is being able to describe what it is you want.

That's where the Strategy Circle comes in.

What is it that I want? What would have to happen for those things to take place?

And then... is there any way I could get this part done without doing anything?

Take these videos. Back then there'd be no way to get them out into the world. You'd be duplicating VHS tapes.

Now the only thing I need to do is push play, talk like this, and share the video with my team. They take it the rest of the way.

It's not my job. And it's not your job to do every step in something.

When all you do are the things you love and the things you're really good at, they feel effortless. And your output goes way up.

And if you're not the visionary... if you love the technical things, it's the same.

It's not your job to come up with the vision. Your job is to find people with the vision, make yourself available to them, and collaborate.

It's a great time to be alive.

Do your job, let everybody else do theirs... and anything is possible.

Show notes: https://deanjackson.com/podcasts/tol/131-thats-not-your-job-just-do-this/

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

The life changing magic of having a “reset button” Oct 11, 2026

Show notes

Good morning.

We've officially jumped into journal number eight.

It's November 1997, and I'm living in a condo in Winter Haven, Florida.

A nice life is starting to shape up. But I'm ADD... and I don't do well with things that need constant maintenance.

The journal entry is dated November 16, 1997.

Under a heading called "ideas to make my life better," I'd written "personal manager."

I need someone to make my life easier. Someone in Winter Haven with a car, who can do things on short notice.

Take my car to get serviced. Go to the DMV.

And the words that came out were these: "I'd like a reset button for my life that makes sure I have exactly what I need when I need it."

So I made a list. Wouldn't it be great if I could push a reset button every week?

The condo's cleaned. The laundry's done. The fridge is stocked with the foods I want for the week.

The car's clean and full of gas. The dry cleaning is hanging in the closet.

That's what I want to give you today... the life changing magic of hiring a reset button.

A lot of entrepreneurs are busy, and they're on the cusp of getting an assistant.

But the first place they think about is the business. One full-time assistant for the business side of things.

They completely miss the super value of freeing up your personal time.

I had a lovely lady named Mandy cleaning my apartment. She'd emigrated from the UK and cleaned houses to make a living.

One day I asked her, "Would you be willing to do some other things for me? Spend all of Monday on them?"

She said it would be a nice change from just cleaning apartments. She was more than happy to do it.

So she created a great little system.

She'd come on Monday and drop my laundry at the fluff and fold.

Go to the grocery store with my list. Come back and stock the fridge.

Clean the whole condo. Take my car to the car wash and fill it up.

Then pick up the laundry and hang it in my closet.

At the end of the day on Monday, I had a completely reset environment.

Clean apartment. Dishes done. Fridge stocked. Garbage out. Car full of gas.

It was such a freeing thing.

All the things that were niggling at me, the things an ADHD brain neglects, were just handled.

Because we have a tendency to take things to the last minute.

If the gas light wasn't on, I didn't need gas. Running out of clothes is what got the laundry done.

There's nothing wrong with it, exactly. But it's frustrating... for me, and for anyone you live with.

In a way, this is an offshoot of the Strategy Circle. What do I want? Here's everything I want. How could I get those done?

And your brain finds the answer. In my case, it was Mandy.

Think about how many things you're doing that you could cheerfully give up.

I think there are at least four, five, eight hours a week of things you could hand off right off the bat.

This eventually evolved into a full-time easy button... and we'll get to that in a future journal.

For now, think about how you could put a reset button in your life.

I promise you, it will change your life.

Show notes: https://deanjackson.com/podcasts/tol/130-the-life-changing-magic-of-having-a-reset-button/

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

Transforming obstacles and opposition into action Oct 10, 2026

Show notes

Good morning.

We're wrapping up journal number seven, of hundreds of these journals.

It's late 1997, and we're heading into 1998.

And one thing jumped off the page for me today... maybe the most important thing I learned in my first year at Strategic Coach.

I'd joined Dan Sullivan's Strategic Coach program that year. I'm still in it.

Dan has a prominent position on my Mount Rushmore of influences.

Journaling is really thinking about your thinking. But sometimes the strategy you use makes all the difference.

I noticed that before Strategic Coach, I was asking a lot of questions like "Why don't I?" or "Why can't I?"

That's completely natural.

One of the things Dan taught was something he called the Strategy Circle.

As entrepreneurs, we're constantly imagining a bigger future. Things we want. Things we want to pursue.

And our brain is really good at two things.

The first is this. As soon as you say "I want this," your brain immediately finds all the obstacles standing in the way.

Rather than backing away because of them... embrace it.

Let that part of your brain list every obstacle. Why can't I get this? What would have to be true?

You don't have to solve anything yet. Just itemize them.

When you're done, that's the trigger for the second thing your brain is really good at.

Transforming obstacles into ways to overcome them.

Take them one by one and ask, "How could I handle this? What could transform this into an action?"

Dan calls the core process VOTA. Vision, obstacle, transformation, action.

Follow that sequence and your brain comes up with the ways to do it.

I've used it in all of my journals ever since, to get the things I want done... and especially to get them into action.

Because sometimes the things that stand in our way do just that. They stop us.

Or we spin our wheels in the negativity of "I can't do that because of this."

Here's the parallel I found in my journal.

"Why" questions are built for finding obstacles.

"How can I overcome this?" is a powerful question.

You don't need to know exactly how yet. You just need to understand what would have to take place.

And I love that 30 years later, Dan is still building on it.

Anytime he wants a result, the first question he asks is, "Is there any way I can get this without doing anything?"

If not, what's the least I'd have to do?

And then, is there a who who could do my least?

That's a great little exercise, built on the chassis of the Strategy Circle.

It's a good example of something we've talked about a lot in these videos... turning your ideas into intellectual property. Tools and frameworks you can use yourself and share with others.

Dan has built an amazing organization called Strategic Coach around exactly that.

I'm a big fan, and you couldn't go wrong looking into it yourself.

So the next time you catch yourself asking why you can't... let your brain list the obstacles.

Then ask how.

Show notes: https://deanjackson.com/podcasts/tol/129-transforming-obstacles-and-opposition-into-action/

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

This secret “sock puppet” method changed the way I write my ads Oct 09, 2026

Show notes

Good morning.

We're being driven home from Concord.

And this is going to sound crazy when I say it... but I want to talk about sock puppets.

I was looking through my journals at where the idea of meeting people where they are in headlines came from.

At the same time, I was going really deep into the way Steve Scott approached writing infomercials, in A Millionaire's Notebook.

He talked about making a list of every possible objection somebody could have.

Not buying your product. Not buying anything in the category. Buying from somebody else.

Here's my interpretation of it.

All of those things are going on in the back of their mind while you're talking to them.

So whatever you're saying in your ad, your video, your letter... that conversation on the surface is really secondary to the conversation going on in their mind.

I imagine it like two sock puppets having a conversation, while the real evaluation happens somewhere else.

Steve illustrated it with the script for Lori Davis Hair Care.

Somebody watching might be thinking, "This probably won't work for oily hair." Or, "My hair is really dry. Will this work for me?"

I think the worst way to handle that is a frequently asked questions page.

"Does this work for dry hair?" "Yes, it works for dry hair."

It's too overt. It's a setup.

The valuable way is to know that question is going on in their mind... and answer it without ever bringing it up.

If they can get that concern addressed without having to ask, they value it more.

So Steve wrote a part of the script explaining that the products were formulated to adapt to whatever condition your hair was in.

That answers the question. Nobody had to ask it.

When I started thinking about the dialogue going on in people's minds, I realized that if I could get inside what they were thinking and address it in the headline, that was a win.

In the late '90s we were running ads headlined "How to buy lovely homes in Winter Haven with zero down payment."

Zero down mortgages were just becoming a thing.

But people might be reluctant to respond, because responding felt like admitting they didn't have any money.

So I added a little something to the headline for the sock puppet.

"How to buy lovely homes in Winter Haven with zero down payment (even if you can afford to pay cash)."

The response went up.

Now people could feel safe under that protective umbrella. They could be someone with all the money in the world who was just curious how these zero down mortgages worked.

You can see the same thing in the Muskoka home sites.

"I need to sell these six Muskoka home sites in the next 30 days, and I'm willing to sell them 33% below their current appraised value."

Getting the lots appraised answers the silent questions before anybody asks them. Why would they be doing this? And 33% off of what?

It addresses the skepticism in a way that moves them forward.

There are a lot of subtleties in this, and I'm going to do a couple of videos going through the process in more detail.

But for now, whenever you're talking, imagine there are two conversations.

The sock puppet conversation... the words you're saying and the words they're saying back.

And the deeper, silent dialogue going on in their mind.

Use your sock puppet to speak to that silent part of their mind, and you're going to win.

Show notes: https://deanjackson.com/podcasts/tol/128-this-secret-sock-puppet-method-changed-the-way-i-write-my-ads/

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

How I use my journal when “things” are on my mind Oct 08, 2026

Show notes

Good morning.

It's a cloudy morning. Looks like it's been raining.

Somebody asked in the comments... do you ever write negative things in your journal?

Great question. Because I do.

And I've got some very specific ways I use writing when things are on my mind.

Disappointments. Troubles. Negative emotions. Whatever's getting in my head.

Most of the time I use my journal to have conversations with myself.

That's something I was doing a lot back in 1997, figuring out my way and where I was headed.

I'd walk through a decision and play both sides of it. I still do that a lot.

Asking myself questions about a specific situation is a very helpful thing.

But there are some things I don't want in my journal.

A conflict with another person. A situation that's really gotten under my skin.

For those, I do something I call tea therapy.

Here's how it works.

I go to a cafe and get a cup of hot tea. I take some loose sheets of paper... printer paper, or a yellow pad.

Then I write a letter in super small print, and I get everything out of my mind.

If I need to have a difficult conversation with someone, I have it right there on the page. Or I write the letter that unloads what I really want to say.

It's cathartic. There's something about saying the things you'd normally hold back and getting it all out on the page.

I spend 50 minutes, maximum.

At the end of the 50 minutes, I tear the pages into little pieces.

There's usually a little tea left at the bottom of the cup. I put the pieces in, stir them up... and let them go.

When I throw out the cup, it's gone.

That's the symbolic ending to that particular issue. And it's very reliable.

I don't do it that often. I have a pretty happy life, and I stay away from conflict and from people who bring me down.

But there are still times when you're in something that needs thinking through.

And this is a very helpful way to do it.

If you've got something on your mind, give it 50 minutes and a cup of tea.

Then let it go.

Show notes: https://deanjackson.com/podcasts/tol/127-how-i-use-my-journal-when-things-are-on-my-mind/

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

How to write the headlines real prospects can't resist Oct 07, 2026

Show notes

Good morning.

Day 110 without rain, and today it rained. So I'm in the car.

I want to talk about the thing that's been the biggest key to every ad, postcard and letter that's worked for me.

The headline.

I was looking through journal number seven, from 1997, and I found something I learned back then that I still use every day.

It came from a great book called Great Print Advertising, by Tony Antin. He ran creative at Reader's Digest, and they blended an editorial approach into their advertising that made everything crystal clear.

The first thing... the best headlines meet people where they are.

I'm not trying to impose my will on anybody. I'm trying to get the attention of the right person.

One of the most reliable ways I know is a headline that starts with "if you."

We've run this one for over 30 years: "If you plan on selling your house in the next 6 to 12 months, what you do right now can make a difference of thousands of dollars."

A realtor client asked a lady what caught her attention. She didn't even hesitate. "I'm selling my house next year, and I saw there were things I should be doing now."

That's it. It called out exactly the right person.

Same chassis. "If you're looking for an amazing lakefront house in Winter Haven, read this."

There's something about "if" and then "read this" that's magnetic.

And sometimes meeting people where they are means letting them sit in their uncertainty.

When mortgage rates kept dropping, everybody was shouting "refinance now." Even Dave Ramsey went on a rant about it.

But most people didn't know what their rate was, or whether lowering it would make a difference.

So for Churchill Mortgage we wrote "How to know when it makes sense to refinance."

We're not telling you to do it. We're telling you there's a time... and you'll want to know when it is.

The second thing is about the space around the headline.

Tony said to make the headline as big as you think it comfortably should be... and then make it 15% larger.

I tried it, and it pops. It's like your pupils dilate a little.

That's been a signature for us ever since.

The third thing is visual cues that support the benefit.

Think of David Ogilvy's Rolls-Royce ad. Half the page is the car.

If you're selling a lakefront home, don't show a picture of a house on a lake. Show the view from the house to the lake.

That's what they want.

And if you're offering a book, show the book. Our best Facebook ads have been the headline, a picture of the book, and the word download.

Put it all together and you've got a headline people can't resist, because you're speaking to exactly your ideal prospect.

The more specific you get, the more responsive they'll be.

You can't broaden your way into a magnetic headline.

Show notes: https://deanjackson.com/podcasts/tol/126-how-to-write-the-headlines-real-prospects-cant-resist/

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

How to start a journal and watch it change your life Oct 06, 2026

Show notes

Good morning.

We're leaving breakfast, heading to the cafe, and I want to talk about the practicalities of journaling.

I get a lot of questions about it. How do you actually do it? How do you get started?

The number one thing... decide that you're a journaler.

I made that decision in April of 1996.

I'd always written things down. Thinking on paper, notebooks, goals and affirmations going all the way back to tennis.

But I'd never kept any of it.

It was Joe Stumpf who showed me journaling as something worth archiving. So I followed his lead and bought an archival accounting record. Blue lines, one page, no columns.

That was my journal for the first 10 years.

Just deciding it was worth keeping made it feel different.

So that's decision one. Turn pro, and keep it.

Then get a journal you're happy with.

After the accounting books I had a whole Moleskine phase. About 10 years ago I switched to the pocket-size hardcover, and for me that's the perfect balance. I can write in a comfy chair, in the car, anywhere.

Then get into the routine.

I'll often take 20 or 30 minutes before a focused work session to free write in my journal.

Start with lists. Ask yourself questions.

I used to do what I called five by fives. Five questions, five answers each. What are five things that would make my life better right now? What are five things I want to do in the next 90 days?

Sometimes one question is enough. Dan Sullivan kept a daily journal for 25 years, and he'd just ask... what do I want?

When you write it down you see it, and you hear it in your mind as you read it back. It's a reinforcement loop. It tells you this matters.

Looking back through 30 years, the early journals have pages and pages of affirmations.

It's amazing how many came true. I wrote that I drive a Midnight Blue Porsche 911... and I do.

If anything, I undersold myself.

What you write about, you think about. What you think about, you talk about. And what you talk about, you bring about.

Everything happens first in the mind, second on paper, and third in the real world.

Journaling has changed my life, and I'd love to see what it does for you over the next 30 years.

But you can't journal every day for 30 years if you don't journal today.

Show notes: https://deanjackson.com/podcasts/tol/125-how-to-start-a-journal-and-watch-it-change-your-life/

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

How to multiply every sale you make Oct 05, 2026

Show notes

Good morning.

One of the easiest ways to multiply your business is to multiply every transaction.

Every time you make a sale... that is not the end.

Back in 1997 I was writing out the whole sequence. Picking who you want to work with, getting them to raise their hand, educating and motivating them, making an offer, doing business.

Most businesses stop right there. They sold the car, sold the house, cleaned the carpets... on to the next one.

That's a missed opportunity.

Stretch the transaction to include the 30, 60, 90 days after what you'd call the conclusion.

It starts with intention. You're becoming a transaction multiplier, not a get it done and get on to the next one kind of business.

And here's the elegant part. That's naturally when people talk about it most.

Somebody buys a house and for the next 90 days that's all they talk about. "You've got to come see the house."

Same with a new car, a new club, a new restaurant, a new book.

It's like a jet stream. The attention is already moving. You just need to channel it into more business.

We call one version of this the listing next door. A sold sign often begets a for sale sign.

I watched it happen on my own street. One neighbor sold, and a couple of weeks later another one listed.

Maybe they didn't want to step on toes. Maybe the price surprised everybody. Either way, now it's their turn.

Then make a game of it. If you have a game, you need a score. If you have a score, you need a metric.

Not just "will I multiply this transaction?" but "how many times can I multiply it?"

Think about mosquito control.

Before the treatment, nobody can sit by the pool or have dinner on the patio.

After it, they have a mosquito-free backyard. That's remarkable. They'll brag about it to their inner circle.

So hand them a free mosquito treatment to give a friend. That's putting legs on the momentum that was going to happen anyway.

In real estate, as soon as a house goes on the market, we put out an info box flyer so the neighbors can scan a QR code and get every detail. An instant open house.

We send a just listed card to the closest hundred neighbors. "Do you know what your neighbors at 22 Graystone did last night?"

Whatever you do, people are going to talk about it. Let them be the hero who introduces somebody to you.

A restaurant can hand out a $25 gift card. The person who walks out of your treatment room with 85% less foot pain is going to tell everyone who complains about theirs.

So adopt the mindset. I'm going to multiply every transaction I get.

Then ask how you can equip people to make it happen... and watch what happens with your next few transactions.

Show notes: https://deanjackson.com/podcasts/tol/124-how-to-multiply-every-sale-you-make/

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

The mindset behind irresistible offers Oct 04, 2026

Show notes

Good morning.

Something came through my algorithm today. A memory of a talk I gave at Joe Polish's Genius Network annual event in New York, probably 13 years ago.

And the timing is perfect.

A few days ago we were talking about irresistible offers... making your offer so good that people would feel crazy not taking you up on it.

You saw the genesis of it in my reading of My Life in Advertising by Claude Hopkins.

This talk is the perfect summary of all of it. So here it is.

It comes down to one question.

What would you do if you only got paid when your client gets a result?

I call it a clarifying question. The first time you ask it, it's more of a terrifying question.

But here's the good news...

If you only get paid for results, you have to deliver less than you'd have to promise.

Here's how it works with our real estate websites.

We give agents the website. I buy the domain name. I take them through a 90-day training program.

No money out of pocket. No credit card up front.

And if they've done a transaction at the end, they pay $1,500 and then $99 a month.

There's no friction in getting people to say yes to that.

When I have to convince people to pay in advance, I have to parade the results of everyone who came before them.

When I only get paid on results, I just have to help them get one.

I did the math. Delivering the result costs about a quarter of what it costs to acquire a customer.

And people are far less attached to future money than they are to present money.

Imagine a coaching program where on the 1st of the month we deposit $2,000 into your bank account... and on the 2nd we take $1,000 from your card.

Who would ever leave that?

A compelling offer is 10 times more powerful than a convincing argument.

Your prospects are like mice. You don't have to convince a mouse to go get the cheese.

So what would you do if you only got paid when your client gets a result?

Ask it seriously... and see what it changes.

Show notes: https://deanjackson.com/podcasts/tol/123-the-mindset-behind-irresistible-offers/

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

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