Reliving 1st Jobs & the Future of Your Taxes

by Mike Lester

Mar 29, 2021

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Kristen (00:04):

There is a Dwight in every office is my theory in life.

Mike Lester (00:08):

We don’t allow Dwights at Talon Wealth Management.

Kristen (00:10):

Yeah, there’s a Dwight. There’s a Dwight. We’ll talk about it later. There’s a Dwight. Anyway.

Mike Lester (00:14):

There’s a Dwight? Okay. I’m not sure.

Kristen (00:16):

America’s favorite mockumentary is officially The Office. It ran on NBC starting in 2005 for nine seasons. But in 2020, we streamed more than 57 billion minutes of The Office on Netflix. And I will admit it, we were in a plague. I contributed to some of those hours.

Mike Lester (00:33):

Yeah. And if you haven’t, you probably should. It’s a good show.

Kristen (00:36):

Who was your favorite character from The Office?

Mike Lester (00:40):

They were all great. My favorite was Darryl.

Kristen (00:43):

A great character. An underestimated character.

Mike Lester (00:45):

He wasn’t in every episode. You know how they all look into the camera at some moment? When he’d say something and look at the camera, it just cracked me up. And then also-

Kristen (00:52):

He had such a stone-cold face.

Mike Lester (00:53):

… Yeah, a stone-cold stare. And then I ran into him at a… I’d like say it was a restaurant, it was a bar one time. He was out for just kind of a fun evening with Zac Efron.

Kristen (01:05):

Because that’s normal.

Mike Lester (01:06):

Yeah. Well, I just didn’t expect to see the two of them together, you know? And so they were there just having a good time. Both of them were super nice. So not only do I love his character, he’s a really nice guy in person.

Kristen (01:16):

Having a favorite character on The Office is difficult.

Mike Lester (01:18):


Kristen (01:19):

By the way, if you say there’s no Dwight, you may be the Dwight, but we’ll talk about that later. Mike, you’ve been a financial advisor for 20… How many years?

Mike Lester (01:27):

Twenty-something years.

Kristen (01:28):

We’ll go with that. But you weren’t born with a subscription to the Wall Street Journal and a calculator in your hand. I mean, you did other stuff, so I want you to flash back to being a teenager. What was your very first job that you received a paycheck from?

Mike Lester (01:42):

Well, it was cash money, Kristen. I think it’s long enough now that the IRS isn’t going to come after me. There were probably a few checks in there, but it was cash money. We lived in a neighborhood, enough homes to where I could sort of go door to door. I made up these flyers and I put them in mailboxes and mowed yards.

Kristen (02:00):

But you not only mowed yards, you made flyers. You advertised to mow the yards.

Mike Lester (02:04):

I actually did marketing.

Kristen (02:07):


Mike Lester (02:07):

Of course, I couldn’t drive. I was probably 12, 13. I had a skateboard. I could basically get everything on that lawn mower and drag myself on the skateboard to whatever lawn I had to mow.

Kristen (02:17):

That’s awesome. I decided to reach out to a few friends who have very successful careers and find out what their first job was.

Speaker 5 (02:25):

I was 16, I think, and it was waiting tables at a very small restaurant. We had a smoking and non-smoking section.

Speaker 6 (02:34):

Wow, so first paycheck, that’s really pushing it back there. I bounced around a lot of different jobs because I was always looking for, where can I work more or who’s willing to pay me a little bit more?

Speaker 7 (02:45):

My first job was at Chick-fil-A. I was a cashier there. I came home smelling like chicken every night, but I did get free Chick-fil-A and lunch every day so that was pretty cool.

Mike Lester (02:57):

She got fed. There you go.

Kristen (02:57):

That’s right. I like that. And whether you hated or loved that very first job, we all felt that shock when we opened our first paycheck.

Speaker 5 (03:05):

The first time I had an awareness of taxes was when I was working my first job at a restaurant. They asked me to fill out a W2. I was completely lost. I had to call my parents. I think I was paid a dollar per hour and I was paid in tips, but I understood none of that. And so I was so confused why at the end of every night I had to cash in my tips, add all these numbers. And at the end of everything, I never got a paycheck because taxes were taken out of it. So I was very confused and a little heartbroken when I realized all the money I earned I didn’t get to keep. A fun lesson.

Speaker 6 (03:39):

I remember being a little bummed out about what you end up with after everything was taken out.

Speaker 7 (03:44):

I do remember asking questions about what taxes were taken out, what were they going to be used for?

Speaker 8 (03:51):

I remember being a little surprised part of my mind thought that only adults pay taxes, but it only really started to impact me when I got older and got higher paying jobs.

Kristen (04:04):

What about when we stop working? Taxes, do they go up, do they go down, do they stay the same? Where do we stand?

Mike Lester (04:11):

Kristen, it’s changing and people are nervous. And probably one of the biggest things that we’re working with people with right now is taxes now, taxes in the future. We’re into tax season, right? Everybody’s going to be getting their tax documents and heading out to go see their accountant or CPA or tax preparer.

Mike Lester (04:27):

Then, Kristen, just look at what’s going on. I mean, first seven days, 40+ executive orders. Biden isn’t instilling a whole lot of confidence in what taxes, much less pipelines, much less whatever else is going to look like here in the future. People are very worried about jobs, because again, look at the pipeline situation. People are worried about taxes.

Mike Lester (04:47):

And gosh, I was just looking… We were talking about the GameStop issue here and we’ve already got Ilhan Omar out there pushing for a new tax on stock trades now that-

Kristen (04:58):

Hmm, yep. Didn’t take long.

Mike Lester (04:59):

…It didn’t take very long. I mean, just give her a week she’s out there. And just look what that means. It’s not taxing you on the profit necessarily. It’s taxing you on the trade. So all these things that are going on, and people are looking at these executive orders and people are looking at the changes and people are looking at the stimulus is going, and going, certainly we’re all in this together. We want the country to do well. But not being fiscally responsible on how we go about doing that just means higher taxes in the future.

Mike Lester (05:27):

And where are they going to get the money from? They’re not going to get it from the people who don’t have the money, right? I mean, you can’t squeeze it if there’s nothing there, right? So they’re going to come after where the money’s at. Well, where is the majority of the money? It’s with individuals that have worked very, very hard. They played by the rules. They set aside money. They didn’t buy the new iPhone every time it came out or the fanciest car or the biggest house. They made sacrifice along the way, built a nest egg, and now they’re transitioning into retirement or they’re currently retired. And they’re looking at this on TV going, “Holy cow, how is this going to affect me?”

Mike Lester (06:01):

We have to answer the questions. Now we don’t know exactly what’s going to happen moving forward with taxes, but we do know how to sit down with clients and show them how to protect their nest egg from future taxes that may or may not be there, right? People ask me what do I think is going to happen? Well, I think taxes will be higher. Who do I think they’re going to affect most? Individuals with the most money. That’s where they’re going to go after.

Mike Lester (06:23):

The question is how do you protect your money if you’re in that situation and you can’t afford to pay higher taxes? We have to have the conversation, so that’s where the tax planning comes in, that’s where Roth conversions come in, that’s where income planning comes in and having an efficient financial plan.

Kristen (06:37):

Mike, considering all of the changes that Joe Biden has made in the first few days of being president, and you mentioned this before, a lot of folks are concerned about the tax implications that could and likely will come about from this administration. You have put together a website,, so that people can get in touch with you and the team and make sure that they are prepared for all of these what ifs.

Mike Lester (07:02):

Yeah, we had this idea back in the election time. Donald Trump and Joe Biden were just polar opposites on so many things and we realized that people really want it to sort of see a side-by-side comparison of what things were likely to look like moving forward, so we were providing that. Well, now we have an answer to the election question, we have an answer to the Senate and the House question, and we realized that change is very, very likely to happen. We just want to help individuals prepare for that.

Mike Lester (07:28):

And so sometimes when you go to the internet and you just ask a question, something very generic like, well, how are all of these executive orders that Joe Biden is signing, how are they going to affect my financial future? How are they going to affect my taxes? How are they going to affect whatever it is you’re concerned about? You’re just going to get tons of information that, frankly, a lot of time isn’t very useful, right? You’re going to point into a hundred or a thousand directions depending on how far you dig.

Mike Lester (07:53):

We wanted to try to summarize it as easy as possible for individuals, and specifically people that are either retired or very close to it. We’re very focused on that. That’s what we do for a living. And we have a pretty good idea from all the phone calls that we get week after week what people are most concerned about and how certainly these changes that are likely to take place could affect your retirement.

Mike Lester (08:13):

What I would say is, if you go to and you want to take just a few minutes to start this financial planning process that will kind of walk you through what can and can’t be done. Take a look at your specific situation and help you prepare for a scenario if taxes are significantly higher in the future, which we believe they probably will be based on everything that’s been signed, based on everything that has to be paid for, how it’s likely to affect your personal economy.

Mike Lester (08:39):

We just wanted to make it as easy as possible, Kristen, I mean, certainly you can call us, we can do that for you, but It’s just It’s pretty easy. We invite you to go there. It’s a brief questionnaire. If you elect to have us reach out to you and do that financial planning, we’re happy to do it complimentary.

Mike Lester

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Reliving 1st Jobs & the Future of Your Taxes