Timothy R. Jester, CFP

15/09/2026

Legacy.

I was listening to something a couple days ago. I can’t even remember what it was.

But the guy I was listening to said something like this.

He said that some parents hand their kids a legacy like it’s a set of car keys and others hand them an empty ignition and walk away. (candidly it sounds kinda like an AI derived analogy, but it stuck with me anyway)

Now, I’m not here to beat up on my parents. It’s an honor to be on this journey no matter how much or how little parental help I received along the way, and I absolutely have received some parental help.

But hearing him say that got me thinking about the legacy I want to leave and how the struggle to produce a legacy from the dust around my feet is real and tough.

I think I need to spend more time digging into specifically what I want my legacy to look like.

I’m curious, have you thought much about what you want your legacy to look like?

02/09/2026

I’ve been reading the same thing over and over for almost a year.

Have you ever read Og Mandino’s, “The Greatest Salesman?”

It’s a collection of ten scrolls that cover topics like habits, persistence and emotions.

If you read it the way it's intended, you start on scroll one and read it three times a day for thirty consecutive days. Once in the morning, once midday and then once before you go to sleep. Then you move on. So, in a perfect world (I have NOT been perfect…lol) ten scrolls is a ten-month endeavor.

Anyway, I’m on the 9th scroll now and it talks about taking action. So action has been on my mind a lot recently.

The scroll nine quote that has stuck with me the best is, “Never has there been a map, however carefully executed to detail and scale, which has carried its owner over even one inch of ground.”

I read a lot. I spend a fair amount of energy becoming better at understanding. But I have to keep reminding myself that understanding is passive. Change is active.

I can fully understand why I keep telling the same stories about myself over and over in my head or why I keep making the same mistake.

I can articulate exactly why I struggle with delegation or setting limits or having hard conversations. I can have complete clarity on a pattern and still choose it again tomorrow morning.

Because there is a gap between knowing and doing that only action can close.

It doesn’t really matter how deep an insight I might have about myself. What matters is taking the step. Acting. Repeating the action.

31/08/2026

This quote, from the same newsletter that produced the last quote I posted, offered a gut punch over the weekend.

“The world is not designed to give you a good life. It's designed to distract you from building one.” – Matty Fusaro

Ooof…

I’ve been spending a lot of time lately thinking about ways I can maximize my life and how I can optimize myself to be a better husband and father and entrepreneur.

What I’m coming up with is the need to cut out more.

And what I’m becoming keenly aware of is that most of what's in front of me on any given day isn’t there to help me.

Phone notifications. News cycles. Social media algorithms. The endless and brain numbing stream of valueless entertainment, fabricated outrage and highlight reels from people I don’t know and shouldn’t care about. None of it is natural. None of it is neutral. And 100% of it is specifically engineered to kidnap my attention and never return it.

What’s even worse is it feels harmless and even comforting in the moments I’m ingesting the stuff.

But my life is just a long series of moments. And if most of those moments are being quietly absorbed by things designed to steal my moments, it means I’m just giving away the moments that should be used to build the life I actually want to build.

I don’t imagine the 80-year-old version of myself sitting in a rocking chair on the front porch doom scrolling. I want to be reading or holding Marissa’s hand while we watch the sunset.

I don’t imagine growing old with my cell phone. I imagine growing old with my wife and kids and grandkids and I don’t imagine the moments I share with them to be created in the moments when we look up from our screens.

Nobody is coming to fix my attention. That’s on me.

The world isn’t gonna get less distracting and the algorithms aren’t gonna become less effective. I’ll shift my attention.

I’m already working toward this, but here is a public and renewed stand to focus on what I want to build and protecting the time it takes to build it.

26/08/2026

What exactly is AI? What exactly are LLMs?

I answered this question a few days ago, and in doing so, it occurred to me there may be a lot of people out there who are familiar with Artificial Intelligence and Large Language Models but don’t really know what they are.

So I thought I’d share a revised version of my answer.

The short answer is that humans have learned how to program computers to replicate aspects of human thought in a manner that allows computers to do a lot of things that used to require a human brain.

We call it artificial intelligence because, well, it ain’t human.

AI, at a base level, is software programmed to learn from data and make decisions.

LLMs are a specific iteration of AI, and companies like Anthropic (Claude) and OpenAI (ChatGPT) have created some of the most popular large language models currently in use.

LLMs are essentially pattern matching systems. They’ve been trained to see patterns in text by being fed billions of examples of language, and their job is to predict what word is most likely to come next.

Because these companies are training their software on massive amounts of text and data, they’ve created quite a few moral and ethical issues. Unfortunately, the people who created the data being used to train models aren’t necessarily receiving attribution or credit.

Until recently, attribution and credit for work you’ve created was considered a holy grail. It’s how a LOT of people create their living.

You created it? You get credit for it. You get paid for it!

If you take a computer that’s been coded to do this and then give it enough data, it starts to “think” and “act” in ways that resemble a human because much of the data it’s learning from was generated by humans.

Because the coding is human and the information it’s being fed has largely been created by humans (although that’s changing quickly because now most coding and some training data is computer-generated too), the computer’s output approximates human behavior and responses.

The more data it takes in, the better it can predict language patterns so, the “smarter” it gets.

What feels really weird is that now we’re seeing computer generated stuff right next to things created by actual humans and sometimes it’s getting really hard to tell the difference.

Obviously, there are still many things only a human brain can accomplish.

But we’re in a period where we’re actively learning what those things are because AI has evolved enough to approximate things like empathy, which until recently we thought was uniquely human.

Clearly, genuine empathy is still very human, but AI’s approximation is sometimes closer to healthy than, say, the empathy shown by an emotionally immature human.

We’re learning in real time that capabilities we used to assume required human consciousness or emotion don’t actually require those things, and it’s forcing the world to redefine what role computers should play.

And really, it’s making all of us ask ourselves, whether we like it or not, what it actually means to be human at all.

23/08/2026

Here are a few tips and tricks around emotional regulation, friendly observation, interpersonal communication and relational boundaries I’m working hard to master as I get older.

Stay calm when provoked.
Pause 10 seconds to avoid a reaction.
Make real space for peace in your life.

Don’t over explain. Work to explain clearly once.
Learn to say no without having to justify your no.
Don’t argue with someone unwilling to approach logic.
Realize when you’ve won and stop talking.
Stop apologizing when you’ve done nothing wrong.

Pay more attention to patterns and less attention to promises.
Don’t share too much too soon.
Notice when someone else shares too much too soon.

Stop defending your limits. Just consistently and quietly honor them.
Avoid arguing with someone playing the victim.
Replace feeling defensive with asking questions.

21/08/2026

Over-giving of my time and energy.

Not saying, “no” enough.

Over-explaining or apologizing for stuff I shouldn’t.

Tolerating more than I knew my boundaries would healthfully allow.

For a lot of years, I defaulted to these things. I subconsciously thought this was how I was supposed to show kindness and caring and how I was supposed to show empathy.

What I’ve come to understand about a less healthy version of myself is that I was really struggling with a scarcity mindset rooted in fear. Fear of what others thought about be. Fear of what others might think if they knew about my past. Fear of being abandoned. Fear of not being able to provide for my family and fear of not attaining my goals and dreams.

Over the last several years, as I’ve made honest strides toward better and better versions of myself, I’ve learned that healthy love, healthy friendships, healthy leadership can hold boundaries. In fact, holding boundaries is essential to mental health. And, as long as I’m striving to live the best and most moral life I can live, I can’t spend any time concerned about what others think of me.

I don’t have to disappear inside the relationships to make them work. And if a relationship requires that to work, I don’t need it in my life, whether it’s family or friends or colleagues.

20/08/2026

Unfortunately, I think authenticity is quickly becoming a commodity.

I think we’re getting pretty close to a saturation point as AI-generated content floods the internet with unoriginal crap.

It’s become pretty easy to spot in graphics. It’s a little harder but still fairly obvious to pick out in writing.

I think people are already getting tired of it.

What’s ironic though, is how AI proliferation has democratized content creation but it’s done so in a way that is creating an incredible amount more value around authenticity.

I’ve always been a fan of handwritten notes, but I think personal touches that can’t be replicated by AI are going to become even more valuable very quickly.

AI isn’t going away. But I think the people who use it to replace themselves in moments where being real is important will end up getting hurt.

And those who leverage it for infrastructure while keeping human intent and accountability highly visible are going to come out on top.

17/08/2026

A new study from SmartAsset estimates it takes $89,898 for a single person to live comfortably in Tennessee.

A separate study conducted earlier this year by SmartAsset, placed Tennessee's statewide median household income at $71,997.

Send a message to learn more

10/08/2026

I talk about this with clients a LOT. Habits compound.

Someone who starts investing $50 a month at 22 will almost always ends up in a better position than someone who starts at 40 with $500 a month. Not because the math works out differently. It’s BECAUSE habits compound.

I’ve also been thinking about this almost constantly in the context of building ITA Wealth Partners.

I didn't launch with a massive book of business or a big team or a lot of obvious structural advantages. What I have is a pretty clear sense of where I want to go and a very real commitment to getting a little better at this every single day.

I think the rate of improvement is the asset. Not the starting point.

This is true with money. It's true with relationships. It's true with fitness. It's probably true with most things that actually matter over time.

I keep coming back to this because it's a pretty compelling argument against waiting.

Right now, I’m on the 9th scroll of The Greatest Salesman and the scroll is all about action so these thoughts are hitting home.

I can’t just hold off until the circumstances look right. I can’t spend time looking around at where everyone else started from.

Most people wait to start from a better position. But the position improves as we go and I think that’s the point.

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07/08/2026

Through most of my early 20's I was pretty good at not looking too closely at myself. I avoided introspection cause if I had, I'd have been horrified by what I saw.

I wasn’t intentionally trying to be a bad person or make decisions that hurt myself and others. And I’m not dishonest, but I was absolutely being dishonest with myself.

The truth is I had a trauma-informed relationship with the stories I was telling myself about the decisions I was making.

And it was honest self-reflection that finally started cracking things open for me and helped me stop leaving a trail of damage and pain in my wake.

I’ve always had lofty ambitions about who I want to be. But the self-reflection forced me to take appraisal of why I was making poor decisions and then decide if my decisions aligned with the kind of person I wanted to be.

In my 20’s the answer was no and the changes were huge 180-degree type shifts.

In my 30’s, the answers were less dramatic and more heading adjustments.

And in my 40’s, the answers are more nuanced and are usually centered around what I’m optimizing for.

But the process is the same. I still have to take the time and space for intellectually honest self-reflection.

Self-reflection without honesty is just performance. It’s going through the motions, journaling a bit, saying the right things in the right places, but nothing actually changes because you're not really being honest with yourself.

Honest self-reflection is different. It's sitting with the uncomfortable question and not rushing to the comfortable answer.

Candidly, I often don’t feel like I’m very good at it. It’s too easy for me to just pick up my cell phone and start scrolling or have an extra glass of w**e or turn on the TV. And when I am sitting with tough things, it’s pretty easy to rationalize the truth.

But, I have seen enough of what's on the other side of honest self-examination to know it's worth the discomfort.

For me it started with a journal and without an agenda. I picked up a pen, the journal, muted my cell phone, and in a quiet corner of the Yellow Deli in Chattanooga at like 1am, I just started trying to write what was in my head without editing it for anyone else.

It was uncomfortable. Honest journaling often still is uncomfortable for me.

But starting that practice then and continuing the practice now, has allowed me to pinpoint the difference between who I am and who I want to be.

And it’s that space in between where all the real growth lives.

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