68: Hate Your Job? It Might Be Overpaying You - podcast episode cover

68: Hate Your Job? It Might Be Overpaying You

Jan 26, 202630 minEp. 68
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Episode description

Most people believe their worst job was a waste of time. The low pay. The long hours. The frustration. The feeling of being stuck.


But what if the job you hated was actually overpaying you?


In this episode, Keith and Doug take a candid look at the lessons learned from the worst jobs we’ve ever had—from fast food counters to hotel front desks—and why those experiences quietly shaped skills that paid dividends for decades. This is not a motivational speech. It’s a practical reframing of work, training, and long-term value that especially matters if you’ve ever thought, “I hate my job” or “This can’t be it.”


You’ll hear why:

  • A paycheck is often the least valuable part of a job
  • The worst roles frequently deliver the best training
  • Early work experiences build empathy, discipline, and perspective
  • Learning to think long-term matters more than short-term income


This conversation is especially relevant for families, professionals, and parents guiding young adults through early career decisions and for anyone building wealth with intention, not just income.


If you’re thinking beyond today’s job and toward a more intentional financial future, we’d love to help.


→ Work with us: https://www.gimbalfinancial.com

Transcript

Keith

Every single job that I've had, and I have been trained for things that made me better for the next job. And and hopefully, young viewers can appreciate that. No matter what you're navigating through in today's job, you are learning skills that will take you to a places you can't even imagine ten or twenty years from now.

Caleb

Welcome to the Up Your Average podcast, where Keith and Doug give no nonsense advice to level up your life. So buckle up and listen closely to Up Your Average.

Keith

Good morning,

Doug

Doug. Keith, welcome back.

Keith

It's a great day to be alive. It's a great day to be strolling in Carmel, Indiana.

Doug

Have the newsletters gone out?

Keith

No. Well, January, but February has not.

Doug

It'll I think you kicked off January's with something like it's a great day to be alive.

Keith

I like it. I I don't remember that because I write it and move on to the next day, but I like the little Travis Tritt to kind of remind me of that.

Doug

Well, Jeff Shreve would tell me before he'd leave the house, and it seemed like every day, but you know, maybe it wasn't, but he would say, Today could be the best day of your life. And I think that's a pretty good way to start your morning.

Keith

I would I had ambition to be a millionaire as a young man, and Congrats. Yeah. Congrats

Doug

on that

Keith

ambition. And What did you think

Doug

a millionaire looked like when you went to be a millionaire?

Keith

Well, I grew up on Lombard in Evansville, so it was the other side of Washington Avenue. Yeah. Yeah. The I was South side, so it was on the North Side of Washington Avenue. But I don't I don't even know that I knew anything. I just thought I should that's

Doug

some Probably a Lincoln Town Car and a driver.

Keith

That's hilarious. Maybe owning the St. Louis Cardinals would be

Doug

a millionaire. Millionaire.

Keith

Then I read the millionaire next door and found out that I don't even know what it looks like because he it wasn't generally it was Sam Walton drove that old pickup truck. F one fifty. Yeah. Yeah. And and I don't think Warren Buffett really ever I mean, when you get to that level, you don't really need money because everybody wants to buy you stuff.

And so but, yeah, I don't I don't know if I had any ambition, but it it's like what it would look like. I just thought I was just crying for that and see what happens. So pretty funny.

Doug

I wonder what the number for kids today. Like, is a million enough? Or do they what they aspire to Yeah. Do they say I wanna be a billionaire? Billionaire? Yeah. That would probably be the equivalent. I'll have to ask Colton.

Keith

Maybe it's a half billionaire. I don't know. Because that would be like, a billionaire is still a far stretch. I

Doug

don't know. Big time. Yeah. But a million was a pretty far stretch a long time. Oh, yeah.

Keith

Well, that that's a great lead in to today's conversation. The the conversation is my worst job overpaid me, did yours. I

Doug

reckon so. You reckon so.

Keith

I I was just before we signed on looking, I made $2.65 an hour at that job, which would equate to $13.00 9 today with inflation. And I think Indiana is 7 and a quarter or something like that minimum wage. I don't think anybody pays minimum wage, do you?

Doug

No. I mean, maybe.

Keith

Yeah, I don't.

Doug

If so, if you're getting minimum wage, call me. Let's get you bumped up and pay.

Keith

Yeah. I don't see any job. Like, where their starting salary is $7.25. They're always in the teens, right? Yeah.

Doug

Yeah. Good help, hard to find.

Keith

So when I I found I think I found 15 jobs that I've had. Okay.

Doug

Yeah, I was You did a deep dive.

Keith

Yeah, I was working on this exercise quite a while. And then I pondered those jobs to try to figure out which was the worst one. And when I was pondering those, I was thinking of some of the antics that happened in some of those jobs. As a paper boy, I couldn't get down the street. I had to come wake dad up because there was a rat the size of a cat blocking the street.

And so, you know, it's 05:30, 06:00 in the morning, and my dad's like, oh. Turns out what was blocking the street was something I'd not ever seen before, but it's called a possum. And so I got down the road, asked the possum. Then my days at Burger King, they had kind of slushy ice back then. Like, it wasn't ice cubes, so we would have ice ball fights in there. The floor would be caked with grease, and we'd have slick bottom shoes, and bodies were flying everywhere there.

Doug

And you washed your hands every time you put your hand in the ice thingy.

Keith

Of my one of my thoughts one of my thoughts from Burger King was the important what they did, I think, the importance of cleanliness because it it could get kind of swirling.

Doug

Makes a difference. Yeah.

Keith

Then I worked for the city of Evansville, and I believe it was called Iceda, c e t a. I don't remember what that stands for, but I was the supervisor of these teenagers, and one of the fellas came in with a putter as his cane, and his leg was spackled, and he got shot with buckshot the night before, and the putter was his way of making it to his first day of work. So that was interesting. Then

Doug

How did you become supervisor?

Keith

I think I must have known somebody. You know, you were talking about that earlier. I don't, like there was a shop teacher, which I don't even know if they do that anymore, that was in charge of me, and then he delegated us to certain Okay. We probably, that was the first time I ever even knew that pot was a thing, and these 15 year olds are up in these old dilapidated houses smoking pot. And I had to say, guessing I burned the freaking house down.

And so then I was a substitute delivery boy of newspapers for the Evansville Printing Corporation, and and that was a that was an early morning thing. And and that, I kinda saw the life of the street. The streets were alive, even whatever time you go there. Then I did some construction work, and I used cigarette loads to get back. They would trash talk me for being trying to get educated and stuff, so I had to get get even with them.

And then I I worked for a computer room when they had to feed big cars, and that was the first time I understood that power corrupts. The guy, the computer operator, was probably not much more than an hourly kind of minimum wage job, but he treated us college students like dirt. And so I started realizing, oh, if you give somebody a title, they can really put it to you. Like supervisor. Oh, yeah.

Oh, yeah. And then I noticed that, and a lot of our young viewers would never know this, but in my days at Tex Instruments, if you were going into a conference room, you better be prepared, because it was going be like walking into a smoke tank. Like, the cigarettes were just yeah. I don't I don't even I don't even I'd probably go a week without even seeing somebody smoke the cigarette right now, but the the conference rooms. I don't know if you

Doug

had No. I didn't have that at all. I mean, I remember the teachers smoking the the teacher's lounge was a smoking nut. Yeah. No. But the And that's all I remember.

Keith

In the eighties, if you went in a conference room, you better beware. So anyway, what was your

Doug

Well, what strikes me of interest that's interesting about all of those jobs is I think all of yours, you had taxes taken out.

Keith

No. That's that's what that's what led me to my worst job is that all my jobs that I had before my worst job were self employed.

Doug

All of those jobs that you just listed? Oh, oh, okay. Yeah. I do. Well, all of all of those jobs.

Keith

No. I was just saying antics in those jobs, but but my worst job was my first one that I had taxes taken out. And I I didn't even realize it until I was looking at it. I'm like, oh, yeah. Is that why it was your worst job?

Doug

Did that tick you off? You're like, what in the world? I'm throwing tea into the river.

Keith

Yeah. No. I I was disturbed by that, but there were many reasons why that was my worst job You

Doug

seem to like, that's what's really got you here.

Keith

No. No. No. But I'll elaborate when we get to that. But the whole point of this is I was overpaid because of the training value that I got in every single job that I've had. And I have been trained for things that made me better for the next job. And hopefully our young viewers can appreciate that. No matter what you're navigating through in today's job, you are learning skills that will take you to places you can't even imagine ten or twenty years from now.

Doug

Yeah, it's very true. Yeah.

Keith

So yeah, I did though, I did when I was thinking about it. I was thinking if you frame your training as an important part of your role, then I think whatever role you're in will have a better perspective for you. But if you think the point of a job is a paycheck, I think if the point of a job is a paycheck, you're going get stressed more often than not. And so being able to figure out what's the point of a job will help you figure out really what is your best and what is your worst job.

Doug

Yeah.

Keith

Who wants to go first? You or me with your worst job? Do you wanna

Doug

Well, think my worst job was probably my senior year in college. I was fresh off a fantastic internship with Merrill Lynch. Merrill Lynch. And I I didn't own fancy clothes. And so one of the guys that I was interning for bought me a suit, and I would wear that suit every day, Monday, Tuesday, Wednesday, Thursday, same suit, Friday. I had a couple ties, I think. But after after that internship ended, I took a job, and I call it a job, I took a job at the Comfort Inn.

Keith

The Comfort Inn. Comfort Inn. Now.

Doug

Comfort Inn in Muncie.

Keith

So if you're shopping for a hotel for the Shreve family, would comfort in and make the cut.

Doug

Man, I wish my dad were sitting right here. So so, no, it it would not make the cut. You know, I I I think and I realize I'm spoiled. Okay? I'm just gonna say that right out loud. I'm kind of a a a Hampton Inn kinda guy. You know? I I think that's good value for the dollar. It's not too like, oh, fancy, but it's always just, you know what you're gonna get. But the Comfort Inn, they hired me, and I'm grateful they hired me.

Keith

Now let me interject. I just I put together a man trip, and and this is and that is a sexist thing. This is just a bunch of dudes going to Alaska.

Doug

I've stayed in Comfort Inn. I would stay in one tonight.

Keith

Well, I don't know that that I would look for an Hampton first. Know that Fairbanks has much more than it can. So if you've ever been to Fairbanks, it's just a different kind of town. So we, I did put that. So in case any of the attendees are viewing, we stayed in a comfort in it.

Doug

Did you really?

Keith

Yeah. That's why I wanted to here too.

Doug

Nice continental breakfast. But

Keith

yeah.

Doug

So I I worked the second shift. There were three shifts, and I was only there a month. One month? Yeah. But you can learn.

Keith

Now do you those of you who are watching, what's your shortest job

Doug

span? That was it for me.

Keith

Yeah. You know, the shortest employee we ever had at Gimbal? Yes. Day and a half.

Doug

Yes. And that guy was my first mutual fund wholesaler. He taught me a lot about the business actually. But yeah, I worked at the Comfort Inn for a month, and it has a lifelong a lot of lifelong benefits for me, which I'm gonna tell you about. But I worked there for a month, I worked the second shift, and that was like I can't remember what time I went in, but I left just after eleven.

It probably like a, you know, one or two to eleven. And it was it was busy, as you can imagine. You know, you're checking people in come three, 04:00, and you're making sure everything's good. You're running towels upstairs, stuff like that. And you're like, Oh no, they forgot the sheets. Okay? I'll put the sheets on the bed for you. That kind of stuff. And then you're in charge come 09:30 or so when things are quieting down. You're in charge of getting the nightly audit prepared and organized.

Keith

So we're auditing dollars? Is that what

Doug

we're talking about? Yeah. Pennies. Remember there were these things called pennies, which kudos to Chick fil A, by the way. They're rounding down on Good the job, Chick fil A. But yeah, so you'd have to count the drawer, get it ready, all this stuff. And I kinda liked that part, but I did not like being alone.

Keith

Okay.

Doug

I was the only guy there.

Keith

You didn't like it for loneliness or fear Yeah.

Doug

No fear, just I like people, I'm a people person. People would check-in. They would leave. And so you you really didn't have a relationship with anybody. Right. And I didn't care for that. But let me tell you the big win of working at the Comfort Inn, only for a month. I have huge empathy for the person behind the hotel desk. And to this day, when I go to a hotel, I make sure I'm spending time with that person. I'm asking them about their day, asking them about the highlights of the year.

I mean, I really want to make that person know they're great. So that's the major benefit, that they didn't, that was not on the job description that I was going to learn there, nor did I even know that was going to be the takeaway. But that was the number one takeaway for me is, A, there's dignity in work, treat people with respect.

Keith

Somehow, I've read a couple books that led me to that idea, and I've kind of even taught the tiner kids when you go to hotels. Like I'm even thinking about the maids that are cleaning the rooms to like put the, when you get ready to leave, you put all the towels on the toilet. Yeah. That's right. Don't trash sit can on the sinks. They're bending over all day long.

Doug

Yeah. Like if I can Can you strip your beds?

Keith

We don't do that, but that's but if I could Leave a tip.

Doug

I would tell you. Leave a tip. Just a little tip.

Keith

Yeah. It used to be a dollar a day. It might be 2 now. I don't know. But if I could interject about what you just said, crazy story in Anchorage last week. I'm signing in for all the rooms with this young lady, and I looked down at her name tag, and her name was Miracle.

Doug

Okay.

Keith

And I said Cool name? Miracle? Are you a Miracle? Yeah. And she says, I am.

Doug

Heck yeah.

Keith

And I'm like, Really? Tell me about that. She said, I was born dead.

Doug

Okay.

Keith

And I'm like, Really? And she said, My dad wouldn't let him take me away. He said, Give me her. And he held me, and I came to life.

Doug

Dang. Power of a father.

Keith

And I was like, definitely.

Doug

Power of God.

Keith

Yeah. And so Wow. I just kept asking her about it. And Miracle, because I took the time to interview, just gave us free parking while we were there. I thought, How kind of her? But Miracle probably hadn't anybody asked her about her name. So it doesn't take a lot extra, but what you said is a really good point for everybody, is when you're in places like that, you can add value to the situation. Yeah. Sorry to interrupt.

Doug

No, that's okay. Yeah, that's the job that comes to mind. I have some others that were W-two jobs, but prior to that, I was all entrepreneur.

Keith

Really?

Doug

And it was just hustle entrepreneurship. So, you know, when when you're governed by someone else's schedule, time, and expectations, that was kind of a new thing for me. Yeah. And so to be stuck at the box of the Comfort Inn just wasn't my jam. And thankfully, I realized it quickly and got out.

Keith

There is no glory in staying someplace for way too long.

Doug

Yeah, yeah. And I believe in commitments, and if you're going to, you know, say you're going to do something, do it, but there are times when it's time to get out.

Keith

Yeah, I had a couple of those along the way too. So what else did you learn from the Comfort Inn besides the?

Doug

I mean, you know, you had to show up on time, you were counted on, there wasn't anybody else coming in to save your shift, you had to count that drawer down perfectly, And if it wasn't, it came out of your wallet. Oh, really? Yeah. Wow. Yeah. So that was But you were making an hour. Oh, goodness. I don't know. I don't even know.

Keith

Yeah.

Doug

To to me, I loved to work, and I wanted to have some money. So I was ambitious to do it even if it was the Comfort Inn, but I couldn't tell you what

Keith

it was. I couldn't tell you what it made. So so when you step foot in the Comfort Inn and you're only there a month, they there couldn't have been much training for you then.

Doug

I had a lady who was very kind to me and just kinda showed me how she did it. She lead she led the way. Okay. Yeah. But no, there wasn't any formal training, like, watch these videos, study this policy handbook. No. She just kinda told me what she did, and I tried my best to duplicate it.

Keith

One of my kids went to work for one of the national coffee chains, which you would assume had major training. And what she discovered, she had to go on YouTube and watch videos how to make the drinks.

Doug

Yeah. That's good. That's good.

Keith

It's kinda interesting. But, yeah, maybe training training may be a obsolete thing.

Doug

Might be. Yeah. Like, into our industry,

Keith

I had a I bet it was a two year training process where I would go, but I don't think people train financial advisers like that anymore. Yeah.

Doug

Yeah. That's a good point.

Keith

But but that is kind of the point of this conversation is whatever your job is you have, that that there is some training that's going on. It's just not necessarily formal. It's positive and negative. Right? Like, the positive things you maybe figured out, oh, people have cash drawers, and they happen to be pretty correct. And then the negative is like, oh,

Doug

Experience is such a good teacher, and on the job training is the best. Yeah. Just as long as somebody will be patient with you.

Keith

Yeah. Man.

Doug

How about you?

Keith

Well, I thought that getting a job was the thing, and I hadn't had a job, and I'd probably been 14 or 15, but I had a lot of money because I had done the entrepreneurial things. And so my friend got a job at Burger King, and he had an in for me.

Doug

Gotta know people. Like I said earlier, it's all about relationships.

Keith

And so when I got to Burger King, they handed me this kind of shrink-wrap bag with this polyester shirt that I was gonna wear. And then I I now was a man in a uniform. So the Burger King, I think their saying was, Have it your way. Have it your way. And definitely working there was not my way.

But I, remarkably, I don't know how many times they fired me and rehired me, but it was a number because I had a sarcastic kind of bent to myself. And the managers there were they thought they were the president of The United States, right? And so they treated us hourly workers in a kind of a condescending manner, which brought out sarcasm. Right? Right. Yeah. So at And you were how old? 15, probably. Okay. Yeah.

Yeah. And And I usually work with a sarcastic friend, so like the little ebb and flow of that. But when I think of the things that Texas, not Texas Instruments, but Burger King taught me, And this is me just thinking back about it is one of the ideas they taught me was to be a salesperson.

Doug

Okay. To like would you like a large fry?

Keith

Yeah. The add on Mhmm. Which

Doug

The add on clothes?

Keith

Yeah. Wasn't my strong suit because it just seemed hokey to me. But when you compare it now as a kind of a seasoned salesperson, when you hear somebody ask for that, aren't I smile? I do too. Yes. Yeah. They didn't have the jumbo meals back then. They just had a large or something like that. Or if you just ordered a hamburger, would you want fries with that? But really learning sales early is a big deal. Yeah.

Doug

And learning a product. Right.

Keith

Right. And so that I thought was something I learned. I thought it was silly at the time, but it was important to know because as a young stockbroker, I would go for the add on sale because I needed to pay rent back then. Right? Oh, yeah.

Doug

Would you like a bond with that stock, sir?

Keith

Exactly. You know, if you like Walmart, what do you think about dollars in the bank? And there is a country western song, God is great, beer is good, and people are crazy. I discovered that the public is a little peculiar working at Burger King. Yeah.

That helped, because really, really I experienced the public in a broader before I worked there. They just, lot of times, aren't kind. And that didn't, at first it was a little off putting, but it helped me to realize, Oh, I live in a little bubble here, and a lot of people aren't like what I experience. And they may be really mean to you, and probably I reverted back to what I learned on the playground, sticks and stones will break my bones, but words will never hurt me, so that I could kind of take

Doug

it in. Make you go home and thank your parents at the end of the day.

Keith

It would. And also what I learned about that is I personally wouldn't talk trash in a drive thru window to anybody. Yeah. Just figure out why. No. I wouldn't do it. Little bonus for you.

Doug

Yeah. That's the title of this podcast. Don't talk trash in the drive through.

Keith

If you do that, I would stop. Buyer beware. Exactly. I would stop. You have teenagers stuffing a bag full of food. You figure it out. I and this one this one that I learned, really, it's kind of a funny one, it's kind of an ADD or an OCD thing, is I learned to break down cardboard boxes.

Doug

Okay, yeah.

Keith

And I think it really helped me in business, At first, probably as a teenager, I thought it was stupid, but they only have so much room in their dumpster, right? And if you throw a cardboard box in there, it's gonna raise the cost of their trash things. And so the idea of breaking down a cardboard box is thinking longer term about something. And I think that's one of the gifts I have in business is that I can look at the present situation, but I can project it forward. Like I can project it

Doug

That's awesome.

Keith

If you throw big boxes into the dumpster, you're going to have a higher chance And so it's kind of a weird thing that I just learned to break it down. And I recognize a lot of people don't think that way because maybe they never worked at the King, you know? So that just I saw it as a principle of thinking long term about situations. It was good. Yeah, that's good.

And my final and most important lesson that I learned is a paycheck is limited. And that's what you had, right? A paycheck was not all that in a bag of chips. I just forgot what I knew before I had my first paycheck. It was my first W-two job, Probably was a little angry at, like, all the beneficiaries on that check because I would pay I don't even think before that we knew we were supposed to pay taxes.

Right? Like, I was mowing yards. Right. I don't think I ever did it. In case you're listening, I heard that. So it was a long time ago. Remember it. Yeah. And you've caught up since. I'm sure I've overpaid since. So Yeah. So so when I thought about that

Doug

Yeah. That's a big deal.

Keith

The hours? I mean, my my my pay was limited on when somebody told me I could work. Yeah. Whereas before that, I could work anytime I wanted, I would do all kinds of things, shovel driveways, shovel sidewalks, and and just entrepreneurial about it, and never lacked for cash before that. So I was at the mercy of those managers to get hours, and if I had annoyed them the week before, they'd probably not give me hours.

And so I was limited by what they said I was worth, what they chose to pay me, and it limited my possibilities. I just, I mean, I did elevate in there. I went from feeding hamburgers on the hamburger machine that was a conveyor belt, you put a frozen hamburger on it, and then you'd go down and put it on the bun and put it in the steamer and all that. Then I they let me get to the fryer, and then I got And then when they figured out I could count, they put me on the drive through window. And so we had a lot of things going on.

However, I look back on it and smile at that time, but it it was it was hard work. It it definitely it literally stunk. Like I would go home and I couldn't get the smell off

Doug

Oh, of yeah. Yeah. So

Keith

that was the Burger King. And I just wanted to have kind of this conversation with you because maybe a lot of our young viewers are in their first job, maybe out of college, or maybe they're younger viewers and they're trying to figure out what work is about. But I think what I would encourage you is to realize that there's work is more than just your paycheck. Like even if you're in a job you don't care for right now, there's something going on there that's carving your character to something better for the years ahead.

Doug

Oh, yeah. Even if it doesn't show up on your resume, that would be my message to especially some of you who are seeking the perfect internship. Like, work work has such big time value to your future. It's not what's on your resume. It's who who it's what it builds inside of you. I think all those jobs that I've had

Keith

have influenced me in a way that I could work almost anywhere. Like they have impacted me to realize that a key driver for me is I'm going to work so I can help people. Yeah. And if I can help people, it adds meaning to life. And if I just look at it as a paycheck, even if it's the biggest paycheck I could ever imagine, there's no meaning in that, I don't think.

But when you realize I can take the skills, the God given talents I have, and employ them in a way that help people, that's really a cool thing. So like in my world system, my worldview, I look highly upon my trash man. Like I just think, That man is awesome. And I could do that job if I had to because I could frame that job in that I'm helping people. And if I could frame it that way, then I look at him is that he's helping me. I in would a world of hurt without his participation in my life.

Doug

I could run on that with just a lot of joy because we talked about the garbage truck guy in our neighborhood over dinner the other night, and he is the man. And he's a cool man. And so, yeah, I could talk about that guy for a while.

Keith

Yeah. Our mailman for many years was Ted, and Ted the mailman. I'm sure there's all calibers of mailman, but Ted knew this principle because we had moved out of our former house, I don't know, a decade, and people were still sending things, but that was still in his route. Carrier. And he took care of it.

Whereas maybe subsequent postal carriers didn't view it that way. And so the level of service was completely different from Ted, but they probably didn't frame their world as they were helping people. So

Doug

Ted must have worked at Burger King.

Keith

Maybe he did. Or we could have done the other maybe he was a McDonald's. We aspire to be a McDonald's, Alex. You can get McDonald's, man. You're another dude. We're the second one. It's so cool. Well, I'd love to hear from you guys. What what work has taught you? What your most of you that are watching, I don't I don't have any idea what your worst job was, but I bet you got some funny stories that Yeah.

We would love to hear about. Yeah. Well, until we see you guys again, I hope your weekend's a good one. If you're in Evansville, man, put on those warm clothes and get ready with the snow shovel. And in the meantime, thanks for hanging out with us today.

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