- And good evening.

You've got More Than Money, you've got Gene Dickison, your host, your personal financial adviser.

And for the next half an hour, I'm at your service completely and willingly.

Happy to be with you again.

If you're a loyal viewer of More Than Money, you know that we often explore the lives of folks who are doing some very interesting things, coming from some very interesting places, and heading to some more even more interesting places.

You'll shortly hear from our guest, Mr. Charlie Gilkey, about his journey.

But before we do, I want to encourage you during these challenging times, be courteous.

I know you have to be courageous.

I know you have to be creative.

I know you have to put the effort out there.

But everyone is challenged, as well.

So, just be a little compassionate about what might be going on in the hearts and souls, and minds of the person next to you.

And if we can just give them a little bit of a break, I think we're all going to be better off.

Folks, welcoming to our More Than Money studio is our honor to have Charlie Gilkey.

Charlie is an Army vet, a philosophy student, an expert in productivity.

Charlie does an awful lot of stuff.

Charlie, welcome.

- Thanks so much for having me, Gene.

I'm delighted to be here.

- Well, your book, Start Finishing, was an inspiration to me personally.

So, for all of our audience listening, I am selfishly using my More Than Money platform to delve a little deeper into the mind of a gentleman that brought me some wonderful ideas.

And in my particular case, we've been talking about having a book published for a number of years.

And it looks like, if I've got my timeline correct, May or June is when our book will be published and Start Finishing is, in many ways, was the impetus for us to get there.

Now, Charlie, you have a fascinating background, not just Army vet and philosophy student - which you put the two of those together, there is a head scratcher.

But to go from Arkansas, where you were born, to Portland, Oregon?

That's quite a journey.

Give us a sense of where does it start in Arkansas for Charlie?

- Where does it start in Arkansas?

So, I was born in Fort Smith, Arkansas, which is a fairly large town.

We had about 100,000 people in Arkansas, and just came from a poor Black neighborhood.

And, you know, as people sometimes ask me what I'm into today and how I got there, I have to say, there's no way that Charlie, who grew up where Charlie grew up, could see where I am now.

And I did well in school.

I was in a lot of leadership positions.

I feel very fortunate that I came from a military background.

And so, that was always being cultivated in me.

I attended the United States Military Academy at West Point for a bit, decided it was not for me, slid into my undergraduate studies and fell in love with philosophy.

And where I grew up, I didn't know that philosophy was a thing.

And I could say, Gene, selfishly or admittedly, when I figured out, it was like, wait a second, there's a field of study where I don't have to choose exactly what I'm studying?

Like, I can study all the things?

That's possible?

And so, it appealed to me because at that point in my life, I didn't have to make a choice about what it was.

But I was also... That's tongue in cheek.

I'd been doing and reading philosophy for a long time.

I started reading Tao Te Ching and, you know, The Zen of the Art of Motorcycle Maintenance, I think that's the name of the book, when I was 13 or 14.

- Yes, good for you.

Now, let's be honest, Arkansas, a poor, Black neighborhood, military background - that doesn't lead directly to an interest in philosophy.

Was there somebody in your growing-up years, your childhood years, that maybe led you in that direction, or maybe inspired you to explore?

How did that happen?

- Yeah, I got my way into philosophy from being a deeply religious person, and from the theological side and some of the things I was doing as a young teenager, and then sort of slid into philosophy.

And a lot of my experience in the Boy Scouts, I just had so many friends that were 3-4 years older than me, and they were reading these cool books and talking about the Republic, and they were talking about these things, like, these are really cool ideas.

And so, I wanted to grow...

I wanted to grow more into that.

You know, I remember I was 14 or 15, and I was sitting at the laundromat with my mom, and I had a copy of Plato's Republic.

And I was sitting there reading as the laundry was going.

And she was like, "What are you reading?"

And like, how...

It wasn't dismissive, but she had never been exposed to it herself.

And so, I was reading and just sort of explaining, as best I could as a 14-15-year-old what it was about.

And I just kept falling in love and kept wanting to read more.

And I thought it was... Like many people think about writing a book, and they see people doing things and they're like, "Oh, well, that's the "thing that people do," but you don't know how you do it.

And again, it wasn't until undergraduate I was like, "Wait a second.

This is an actual profession.

"I can teach doing this."

And that was my goal until 2004, 2005 changed some things for me.

-Interesting.

Interesting, indeed.

Now, obviously, our viewers can see behind you, you've read a book or two in your time.

Where did the love of reading come for you?

- My mom, actually.

So, I had the fortune of misfortune in that my mom was teaching at a preschool organization, and we couldn't really afford for me to have preschool.

So, I was sitting in the back.

And that school focused a lot on pre-literacy and learning.

So, I learned to read really, really early.

And so, I just fell in love with books.

It was a way of maintaining myself to, like, get into things, read.

Turned out the books were free from the library, and the places, like, people had books everywhere.

And so, it was just this really great thing, especially if you're a kid that doesn't have a lot of money.

It's a great place to go because they're everywhere.

And my dad was a craftsman.

And so, when he would work on houses, people were always getting rid of encyclopedias and things like that.

So, it just became one of those things that was always around me and that go-to place for learning, for a little bit of getting away.

And I never really thought until, honestly, Gene, the last 3-4 years, about how much of those earlier days being around books and those being my go-to would lead me to be an author and how that plays out.

- Fascinating.

Now, Charlie, no disrespect intended.

You came from a tough start financially, for sure.

I can relate to that precisely.

I'm the sixth child of a carpenter and his wife.

There was no money.

So I know what my journey was to get to college.

What was your journey?

What made you think that you, goodness, coming from your neighborhood, should be heading off to college?

And then, how did you make that happen?

- So, my family did value education.

My dad has an associate's degree, even though he was a tradesman, and my mom ended up going back to getting her associate's and being a teacher's aide.

So, I thought that my pathway was going to be a teacher, like, a high school teacher.

And so, that was, I knew I had to get a college degree.

I didn't quite know how at the time.

What happened is I was selected for gifted and talented education as a kid, and I was just sort of pushed in that routine.

And I loved it.

And in, I think, the eighth grade in Arkansas, I took the pre-SAT, and I did really well...on the pre-SAT.

And so, people are like, "Oh!

There's this possibility."

Like, "You can get scholarships and you can, like, "pay to go to college."

Like, wait, that's a thing?

I didn't know that could happen.

And so, I was really fortunate to have so many great teachers that saw that in me, and again, be involved in Boy Scouts with people that were achieving.

There was just a language of possibility.

There was a language of going to college being a default that I was exposed to.

And so, as I started going through high school and beyond, it was kind of like a thing that was possible.

As I said earlier, after I took the PSAT, a bunch of college brochures started coming in, and West Point popped up.

I had never considered that I could go to a military academy.

I was like, "What's that about?"

But, like, "Sure I'll fill it out and see what happens."

You know, Gene, I was talking to someone the other day.

This is a bit of a tangent, but it's not.

And I jumped into something.

I had no idea what was going on.

He had no idea what was going on.

And I looked at him and I said, "You know what?

"A lot of the best things in my life have come from me stepping "into something where I had no idea what was going on, "and then figuring it out from there."

So, I'm really excited to be in this conversation where I have no idea what's going on, because I know great things can happen.

And so, it was really one of those things where it came in.

I was like, "Sure, let's give it a shot."

And, following natural progressions, again, I was in Boy Scouts, I was an Eagle Scout, there's that sort of pathway from Boy Scouts to the military that's quite common.

And along the way applied to other schools, got some great fellowships and scholarships, and things like that.

So, really fortunate because none of this was on the plane.

Like, there wasn't a conversation where my mom and dad were like, "You can get scholarships.

"Here's how you do it."

No, there was just great teachers and guidance counselors and honestly, just feeling like I was in the right place at the right time.

- Well, you say it wasn't the plan, but it was somebody's plan.

- It was somebody's plan.

- Somebody's plan.

Now, the military for you, of course, has been and was part of your life, an important part of your life.

You spent some time in Iraq.

Did that have an influence or an impact on you that you still feel today?

- Absolutely.

Absolutely.

I am more grateful for my military service the further I'm away from it, which sounds like I'm dismissing military service, that's not true.

You just realize how much of a... Character-building crucible that is, and how much of a competency-building crucible that that is, so I'm still unpacking things that I learned as an officer and learned as a logistics officer when I went overseas for Operation Iraqi Freedom.

What it really changed for me, Gene, is I was already in graduate school for philosophy.

So, pursuing my PhD in philosophy, got activated in the National Guard and ended up going and being federalized.

And when I came back, I had this gnawing...

I don't know what it was, this tension, because I was like, you know what?

There are real problems in this world that a lot of my peers in academia are really well-suited to solve and get involved.

But it doesn't seem to be something that's really important.

And as I kept sitting through my graduate courses in philosophy, no disrespect to philosophers and academic philosophers at all, but I realized that for me, it's like I understand everything that's going on.

I can follow this game.

I'm no longer in that in that game, though, right?

There's like stuff that, one, I think we can get into and actually make people's lives better.

And two, there are different ways that I can show up in this world that I don't know that academia is going to be the best pathway for me.

And so, I fell backwards into, you know, starting my company, starting the blog, starting all the writing in the body of work - again, not on the plan, but as a fairly brash, you know, 28-year-old, I was like, you know what, there's more that I can do in this world, there's more to life, and I'm going to go after that and trade up to the best opportunities, as opposed to stay along this arc that I'm in that I could do well in.

But I don't know that it's going to be my best life.

- That's fascinating.

You mentioned very early on in our conversation a fascinating book, Zen and The Art of Motorcycle Maintenance.

And when that first came out, I was in college.

It was all the rage.

We all read it.

We all had no idea what it was talking about, other than the motorcycle part, we got that part, but the philosophical part was lost on us.

I recently literally, I'm amazed that you mention the book because I recently, as of last night, finished it again.

And the opportunity to see somebody who has said, as did the author of Zen and the Art of Motorcycle Maintenance philosophy, in and of itself, has no value.

But bringing a philosophy that has a practical and impactful effect on people's lives has real value.

Start finishing is as much a book of philosophy as it is a handbook on getting off the schneid and getting things done.

And you use the word "project" a lot in that book.

Give us a sense of what's the philosophy of finishing a project?

- Yeah, I'm so glad you saw that link.

Part of Start Finishing is, it's a little bit of a Trojan horse for philosophy because here's what I've learned, Gene, in doing this.

If you tell people you're a philosopher or you're talking about philosophy, they tune out, not interested.

It's weird, it's you know, we're talking about the existence of chairs or not, like, why does that matter?

So, don't have that conversation.

But I get into the grips of what philosophical issues are trying to get us to, which is how do we thrive?

What does it mean to live a life of meaning, especially if you talk about from an ethical perspective, what does it mean to know?

I focus more on the ethical side of things, because I'm a trained ethicist and social philosopher.

And the first thing that I'll say about projects, especially the type of projects that relate to your best work, which, Gene, we might get into here in just a second, is they're both bridges and mirrors.

They're both bridges and mirrors.

The bridges because finished projects create the life in the work you most want to do.

And so, a lot of people get stuck in their life, Gene.

and are like, "I can't do this, I'm stuck here."

And it becomes a different way of approaching the problem.

If you think, "Wait a second, this isn't about me.

"This isn't about me being uniquely defective.

"This isn't about me not being able to get right.

"I just haven't done the projects I need to get to "this next phase of my life."

I can let go of these character identity aspirations, like, aspersions that I have for myself and just think, OK, I'm going to make different choices about the projects that I'm doing.

So, they become that bridge.

But they're a mirror, Gene, because when you really choose a project that matters, it reflects what's happening for you internally.

All your shadows, all your head trash, all your limiting beliefs, all your beliefs about what's possible in the world start coming up.

So, it's an internal matter, but it's also an external mirror because it shows you the constraints and the givens of your world.

Gene, you mentioned you doing a book.

Well, when you actually commit to doing a book, you have to get real about where doing the work of creating a book lives on your schedule.

And if you're like most people, there's no room for a book on your schedule... - Or much of anything.

- That's revealing.

Yeah.

Or anything else.

And so, when you look at projects as a mirror and you start saying, "Wait a second, let's escape "this idea that it's about me and my character.

"Let's make it about what I'm believing "and what's in my world," then you start to get some traction and start to say, "You know what?

OK, I'm going to make different choices "and it's my choices that are governing where I'm going, "what I'm building, not my character."

- You make a very, I think, two incredibly important distinctions in your book, and you've outlined them already.

The first is the issue of what I am versus what I'm doing.

And how many times have we heard someone that we love and you want to shake them where they go, "I'm just a procrastinator.

I just put things off.

"I'm just not the kind of person that gets things done."

That's unless you're assailing your own character in a totally inappropriate way.

And the other thing that you point out in your book and in some of your writings, I've been exploring a bit, the word "no" for many people is considered to be almost bad etiquette.

You simply don't say "no", but the ability to say "no" opens up the opportunity to say "yes" to the projects that truly reflect who you are.

Do you want to address this idea of how do we overcome our resistance to simply saying, "no, thank you"?

- Yeah, I so love that, Gene.

And what we forget is that, by not saying "no" to things, we're saying "yes" to a lot of other things.

And so, people think that "no" is the proactive choice, when really all the other ways in which they're doing things are also a choice.

And so, here's that sneaky philosophy bit I told you about, Gene.

It's existentialism, right?

Choosing not to make a choice is a choice.

And we have no exit from this as humans.

That's a Sartre reference, right?

We have no exit from this ability to make a choice.

And so, a lot of times, it's like, "I can't say no".

I'm like, "No, no, no, no.

Hold on.

Hold on.

Pause.

"You've already said 'no' to a lot of other things.

"I'm just asking you, are you saying the right no's?

Are you saying a "no" that, five years from now, you'll look back and say, "You know what?

"I wish I would've said 'yes' to that instead of saying, you know, "'no' to it or 'yes' to all these other things," Gene, because the reality is, and I learned this as a soldier on the battlefield, life is incredibly fleeting.

Millimeters can make a difference between whether you go home or don't, right?

And that was one of those lessons that I learned in that period is like we have this one short life.

And I knew it from different perspectives, but I knew it in a different way when millimeters mattered, right?

And so, every way that you spend your time, this 30 minutes, this great conversation, I hope it's great for you, that we're having, there's a near infinity of things that I could have done in this 30 minutes that I'll no longer be able to do.

Right?

Turns out, this is the 30 minutes that I wanted to be spending my life doing.

And so, I think that's what I would want to invert that question of, I can't say "no" to things?

Actually, you already are.

How do you start saying "yes" to the right things?

How do you start saying "yes" to the things that will give you fulfillment, that will give you meaning, that will make a difference, that will actually help you grow as a person in ways that are important to you, not necessarily to everyone else, but to you.

Those are the yeses I want people to start making.

- Very good.

- Versus the yeses of social defaults.

- Very good, "social default".

What a great phrase, it's the things that we are expected to do, or the expectations of others that have been imprinted on us.

Now, speaking of others, do I understand correctly that you are married?

- I am, indeed.

- And do you want to tell us a little bit about your wife?

- Yes, my wife, Angela Wheeler, brilliant soul.

She has a PhD.

in sociology with a specialization in mental health.

And she does a lot of the work with us at Productive Flourishing.

A lot of people, rightly so, will make her more, or will say she's more of the heart of the community because of the work that she does in really helping people reclaim their inner intuitions, reclaim their inner confidence, and really make space for themselves as much as they make space for everything else that's going on in the world.

- One of the reasons I ask about your wife is because, as has often been said, they say it's trite, but often things that are trite are true, that behind every good man is a woman, sometimes kicking him in the butt.

I understand that.

- Yep.

- But your background is so diverse.

Your interests are so diverse.

I was fascinated to see how your wife might fit into that.

I'm actually rather happy to find that not only does she fit into it, she is a perfect complement to what you're doing now.

You've mentioned the name of your company, and it's a particularly interesting name that you've chosen.

And you're absolutely right.

The word "philosophy," often we get reactions that start with eyes start to close, people start to nod off.

But the idea of being productive is something a lot of folks are interested in.

And the idea of having a life that we could refer to as "flourishing" is a beautiful image.

And yet, you wouldn't normally put those two things together.

So, again, I think you're slipping some philosophy in on us kind of under the radar.

Tell us a little bit about your company.

- Yeah, I really love seeing that.

So, at Productive Flourishing, we help people finish what matters most.

And so, a few things going on there, finishing actually doing the work, what matters most, meaning in prioritization and focus.

Right?

And you're absolutely right, Gene, part of the reason I came up with the name Productive Flourishing, and to be honest, I don't know that I would name it that way again, but it's just where it is.

But I noticed how many people were focused on being productive and getting things done.

And the question I kept having, though, is, to what end?

Are you building the life that you want to?

Because if you're just being a to-do-list ninja and you're just getting down the list and making it from week to week, there's more to life than that.

Right?

Or as Gandhi said, "There's more to life than increasing its speed."

And I didn't want to have any real anything to do with just increasing the speed of life.

I wanted to have more to do with increasing the meaning of life, meaning the priority and the focus of life.

So, that's where the "flourishing" comes in.

And that's, you know, coming from a deep Aristotelian, or neo-Aristotelian synthesis of what it means to thrive as humans.

And the reality is, when we take a step back, we would say logically, or philosophically, we want all of our actions to be guided towards our thriving.

Like, we're not going to do things that we know are going to make us worse off.

We do it, but we wouldn't make that choice from a matter of principle, right?

It's an accident in many ways.

And so, Productive Flourishing, my company, ended up becoming that synthesis of like, look, yes, let's get in the world.

Let's do great things.

But let's keep in mind the purpose of those things.

We're talking about flourishing.

We're talking about thriving.

And Gene, on that one, I don't just mean individual thriving, like you being better or me being better, but how are we building better communities?

How are we building better teams?

How are we building a better world?

So,, yes, I'm sneaking in a lot of philosophy, right, because I can't get away from that, just like I can't get away from my military background.

And to be honest, I don't want to.

But I think that's where I want people to go.

And at Productive Flourishing, you know, we have books, as you mentioned, Start Finishing behind me.

We sell tools that help people focus, Gene, exciting news, we're starting an app this year, and that's going to be a really fun, fun new journey for me.

And to be honest, I have no idea how all that'll work.

I've never run an app business before, so we'll figure it out as we go.

But that's really what we focus on.

We want people to come to Productive Flourishing and have that sense of, like, "OK, I may not have less work ahead of me.

"But I have the right work ahead of me, and I'm willing "to get behind that."

- One of the analogies that was given to me many, many years ago, 1,000 years ago now, it seems, is that it makes no great progress to rapidly climb a ladder that's leaning against the wrong building.

So, that fits perfectly.

I have to comment, as we have a moment or so left in our interview, our discussion today on the cover of your book, you have an endorsement from Seth Godin.

I think Seth Godin is one of the primary thinkers, one of the most advanced thinkers in America today in the fields of, in essence, philosophy for the most part.

Who do you read, or who do you draw inspiration from today?

If you could pick one person outside of your self, maybe someone, an author that you know or don't know, you just read, who would you suggest is the influencer on you?

- Funny enough, it's, well, not funny enough, it's actually Seth, right?

Seth has done so much for me personally, but also in his body of work.

So, he's one of those that I do a lot of grappling with.

So, I've gotten a lot of inspiration from that.

And also, give a newer one Stacey Abrams' book, Leading From The Outside, or Lead From Outside.

I'm not getting the name of the book right.

But it's also been phenomenal.

And so, that's one of my newer go-tos when I'm needing some inspiration, as well.

- Well, I encourage everybody out there, pick up Charlie's book, Start Finishing, if you've got any interest at all in how to craft a life where your projects are really in alignment with who you wish to be, and who you want your future person to be, as well.

Charlie, thank you for spending part of your day with us.

Forgive me now, as I turn to the camera and I say "thank you" to all of you, as well, Charlie Gilkey's ideas are very practical.

I get the word "philosophy" might have you go, "Wait a second."

Give it a go.

Give it a try.

Take a test and see if it fits you.

And, as Charlie has said so very well, it's not just about us.

It's about our community.

It's about our state.

It's about our nation and about the world.

And if we can make ourselves a little bit better, that's really the foundation for everything else to be better, as well.

Thank you for spending part of your day with us.

Now, as we wrap up this edition of More Than Money, lots of things that you need to know.

If you have questions about Charlie Gilkey, his book, its impact on me, or any other philosophical question, or if you've got investment questions, income tax questions, estate planning questions, business questions, it's what I do.

Thousands of years of experience.

At least I'm drawing on thousands of years of all the folks I've read and been mentored by, they're all at your service.

All you need to do is ask.

Send me your emails, Gene@ AskMTM.com.

Gene@ AskMTM.com.

I promise you, even though you may not get your email on air, you will have your email answered directly to you.

Every single e-mail is answered.

Folks, thanks for spending part of your evening with us and sharing that with me.

We hope that you'll rejoin us next week with another edition of More Than Money.

Goodnight.