Anonymous Mailbag

It’s Tuesday, rejoice, the anonymous mailbag is here to solve all your life’s problems.

We’ve also got a great offer for all of you out there. Thursday night the Colts travel to the Titans. Nnew gamblers can bet $5 on the Titans or the Colts, you pick, and if your team wins you get $125. That’s a heck of a deal, and it’s available to all readers in Tennessee, Indiana, Illinois, Pennsylvania, New Jersey, West Virginia, Iowa and Colorado. If your state isn’t listed yet, go sign up today, it will be soon.

As always, send your anonymous mailbag questions to, anonymity guaranteed.

And, by the way, some people have been emailing lately, not with questions, but complaining about all the anonymous mailbag questions dealing with COVID. Guess what, THAT’S WHAT PEOPLE ARE ASKING ABOUT. If you have a good question that isn’t remotely serious, then submit that question instead of complaining about the ones we’re getting.

After all, I can only answer the questions I get.

The audience keeps growing for OutKick, so we’ll keep answering the questions people are asking about.

Okay, here we go:

“My family — a wife and three kids — live on Long Island in a state that is as blue as can be – we are sick of New York State taxes, the cost of living is through the roof, the city we live near is a complete disaster, we’re done with our COVID-insane governor, and most importantly, there doesn’t seem to be any chance of change for the better happening via the ballot box. So like so many before us, we’re looking to relocate to a more sensible state. The question for you then is, what state would you recommend we choose? Two important factors to consider are (1) we want to avoid states that have been attracting people who are trying to escape blue states but who are bringing their liberal voting habits with them (we don’t want to have to consider this question again in ten years), and (2) my wife hates the cold and the snow and won’t consider anywhere in the northern third of the map.

So what say you? No pressure, but you will be deciding where we live for the rest of our lives.”

Given your wife’s criteria, I’d look at Florida, Tennessee and Texas.

All three of these states are without income taxes, so you’ll save north of 10% in taxes just based on that decision alone. In addition to these three states, which have become very popular for relocation, you could also look at South Carolina and Alabama. Both states have tons of great places to live with more moderate-sized cities and the cost of living will blow your mind compared to what you’re used to on Long Island.

Plus, there’s no way Alabama, for instance, is ever going blue for the rest of your life. (Not unless Nick Saban runs as a Democrat, anyway).

Georgia and North Carolina have been very popular with relocating people as well, but I think you’re in danger of those states starting to adopt some of the same policies that upset you in New York. If you doubt me, just look at the election results of late.

What I’m seeing here locally in my area of Nashville is people are flooding into the state since COVID, and they aren’t bringing their politics with them. They are moving here precisely because Tennessee is a reliable red state. In other words, they aren’t trying to change things. They’re just happy to be surrounded by people who believe in limited government and limited taxes and to be in a place where the cost of living is relatively affordable.

But, I’ll be honest with you, I don’t really want people to keep moving where I live.

We’re close to full. So if you want to go elsewhere, those of us who live in the Nashville area — particularly those of us like me who were born and raised here — are happy if you’d choose to go elsewhere. We like it as is.

In fact, my mom just bought a new t-shirt that says, “Don’t California my Tennessee,” and she’s pretty fired up about all these new arrivals trying to change things.

So unless you want to make my momma mad, go somewhere else.

In general, I think COVID is going to lead to a substantial realignment of the country.

And I think that sorting is going to make the blue states bluer and, often, the red states redder.

Many moderate to conservative people on the east and west coasts are going to abandon their cities, which have gone so far left wing it’s driving the moderate and conservative voters insane, and move into the central part of the country. The fear of the people in the central part of the country, like my mom, who are generally happy with where we live and our quality of life here, is those people migrating in from the coasts are going to bring their far-left wing politics with them. But right now, at least based on conversations I’m having with these people, they are moving here because they are fed up with the left wing politics and nanny-state COVID decisions of their home states.

So those would be the five states I’d put on my list if I were you.

Good luck.

“So, late 30’s, happily married for 12 years with 2 kids. Dated for 3 years or so before that. Went out for date night on Saturday, and we had a ton of drinks and a great dinner.

For some reason, my wife decides to tell me when she was 19, well before we started dating, she dated a guy that was 12 years older than her and that he was a GM at a male strip club. She shared he had a Ferrari and lived in a high rise and some other stuff along those lines.

I don’t care about that, I thought it was funny/interesting. We’ve talked about each other’s previous relationships before, mainly because we ran in the same circles in college, it was impossible to avoid. In fact, I dated a girl that my wife became very close with after her and I broke up, but before we started dating. I guess what I don’t understand is the timing, why now, 12 years after we’re married bring this up? I asked her and she said she didn’t know why she felt like sharing.”

My bet would be she felt like sharing something new because your date night conversations have probably become routine — and maybe even a bit boring — after 15 years of dating and marriage. That’s easy to do because neither one of you is, probably, working to impress the other person any more.

Think about when you first went out on a date with a good looking girl. You had all your best stories lined up, you were attentive as you could be, paying attention to everything she said, you were working your ass off to try and win her over.

If you’re a girl reading this, you paid attention to what underwear you wore.

But that was over a decade ago.

What do you talk about when you go out to dinner now? Your kids, their teachers, work projects, family issues, I mean, how often does something truly unexpected get said at dinner? That’s why married people gossip so much about our single friends and our married friends who probably shouldn’t still be married to each other, because we have to live vicariously through their lives.

Your wife is probably just trying to spice up the dinner conversation a bit. That was made easier the more alcohol she had. She may even think you now find her a bit boring, and so she decided to drop this nugget into the conversation and see how you reacted.

And it worked!

You’re suddenly intrigued enough about what she said to email the anonymous mailbag about it. And I bet you immediately asked all sorts of questions about this too, didn’t you? Where did she meet this guy? Was she impressed by the Ferrari? How long did they “date”? Did she have to get treated for syphilis after dating him?

I’m filled with questions here, and I don’t even know your wife at all.

Now the issue with stories like these is you might also get jealous of that 31-year-old guy who had a Ferrari and ran a strip club because he got to bang your 19-year-old wife with no strings attached. Most married guys are retroactively jealous of their wife’s wild college and teenage years, before she had kids and got mad because the water bill was too high and the WiFi wasn’t working well enough for her Peloton class.

Back when your wife was 19, she was probably getting banged on the strip club owner’s high rise balcony, maybe blowing him while he drove the Ferrari, and now you’re working your ass off to get her to sleep with you 2.6 times per week and half the time she has sex with you she won’t even take her top off.

But the reason she shared that story, I think, is because she got drunk and wanted to make sure you knew she wasn’t boring. She wanted to surprise you, she wanted to spice up your life a bit.

Have fun with it.

Here’s an idea: married couples, especially those who have been married a decent amount of time, can adopt a new rule: at dinner you have to tell your partner something they didn’t know about you.

Who knows what you might find out?

But I bet the conversation is more interesting.

“My coworker and I have been presented with an opportunity to buy in to the company we currently work at, with the end goal of us eventually taking over the company. This company is very healthy and successful. We will start off with a very small percentage to get things started as we learn more of the business end of things.

Here’s where the question is. Both of us are already working long hours. As of now, we have weekends off. But we feel as though the owner of our company wants us to work more at night during the wee hours and more on the weekend towards this business acquisition. We both have young kids at home, and the idea of coming home and continuing to work isn’t an easy idea to process.

Do we need to embrace the DBAP approach and get to work? I’ve often said we need to decide whether or not this deal is worth it to us. If I decline, I still have a good job with a pretty good salary and normal working hours. If I accept, it’s going to be probably 3-5 years of extra work with a really good payout. But I don’t want to just throw away time with my kids to gain wealth. There has to be a balance there though. What’s your take?”

This is the quintessential question that all parents face: what’s the appropriate amount of work and life balance? The answer is different for everyone.

There is zero doubt that it’s much easier to be the employee than it is to be the business owner. That’s especially the case when it’s a small business, and the owner has to grind alongside the employees on a day to day basis.

It sounds like the current owner of the business is ready to start to dial back the number of hours he works, and he doesn’t want the responsibility of being on call on weekends and late at night. As a result, he’s allowing you guys to see if you can handle the responsibilities of owning his company. If you can, I’m sure he’s thinking he can sell the remainder of the company to you and eventually retire.

If you can’t handle the job, presumably, he can find someone else to buy his company down the line.

So this is effectively an audition to find out if you and the other guy are up to the job.

I can’t speak to your business in particular or what demands it has, but when I started OutKick nine years ago, I expected there would be a ton of employees, often younger than me, who would have my work ethic and drive and that eventually I’d be able to work much less.

It turns out, there aren’t.

The bigger OutKick gets, the more I work, not the less.

That’s because most people, in general, are content to put in mediocre effort and get mediocre results. Most employees don’t think like an owner. Because if they did, they’d be owners too.

So this is really a question for you: do you want to be an employee or do you want to be an owner? If you want to be an employee, you can typically have regular hours and relatively reduced stress. In exchange for those benefits, you’ll make less money and have a much lower upside. But if you want to be an owner, it means you have to bust your ass for the next several years and you won’t have as good of a work-life balance.

Often that will mean your work-life balance will be skewed in favor of work.

Personally, I don’t know anyone who is extremely successful that has an incredible work-life balance. Work is going to be where you spend most of your time if you are going to end up successful.

As an example of this, the other day I was out to a birthday dinner with a friend of mine who owns his own business and has three young kids. He was talking about how tired he was, and I asked him how long it would take him to catch up on sleep if he suddenly stopped work tomorrow.

Without skipping a beat, he said, “One year, I’ve thought about it. I’d need a full year to catch back up for the past decade and feel rested again.”

I think there are a ton of business owners who know that feeling.

Which is why lots of business owners I talk with, if they’re around my own age, plan to dial it back once they hit fifty or so years old.

That’s my plan right now too.

But whenever I say that, my wife just rolls her eyes because she says I’m not wired to suddenly disengage, and she thinks I’d be bored to death without a business to run.

Maybe she’s right. I don’t know.

Regardless, I bring up stories like these because lots of people dream about being the boss, but most people aren’t willing to put in the hours and take on the responsibility to actually be the boss.

There’s nothing wrong with preferring to be an employee, but you need to sit down with your wife and have this conversation about what your expectations are going forward. If you decide to join the ownership ranks, your life will change and you will have to work much harder than you do now.

Maybe that won’t be forever — although I’m skeptical of people who own businesses and think at some point they’re just going to be able to relax — but it will be for a long time.

I think you should go for it, but that’s because I think like an owner. I can’t imagine sitting around for the rest of my life hoping someone else is able to pay me for my work. But, again, I realize that’s a rarity.

Most people don’t think like I do.

And if you’re truly not sure you want to be an owner because you’re not sure if you want to work that hard, you may have your answer already.

Being an employee may suit you better.

Ultimately, if you aren’t sure, you are sure: you should stay an employee.

“I am a 20-year-old from Maryland who goes to a Pac-12 school and is returning home for Thanksgiving next week. My mom and dad have gone full coronabro while riding Joe Biden’s coattails the past few months. My dad who voted republican his entire adult life now voted for Biden because ‘the virus is all Trump’s fault.’

My question to you is how do my brother and I, who is now 29 living on his own deal, with this ludicrous bs over the holiday season?

I completely agree with everything you have said about keeping the elders safe and my parents have lightened up a little bit and have gone out more to eat and to bars, but whether it’s coronavirus or liberal cancel culture I’m not sure the best way to deal with my parents especially after a few drinks. Have any suggestions for me?”

My kids aren’t your age yet, but if my kids came back home from college after spending the entire semester on the other side of the country, the last thing I’d want to do is argue with them about politics.

Especially after the election we’ve just gone through.

I bet almost every parent feels the way I do about this.

The advantage of age is you can still remember being the kid coming home from college, but you can now see things through the eyes of your parents too.

One of the best things about being a parent is seeing your kids develop their own worldviews as they get older. I’ve tried to keep an intellectually open house where my kids are free to come to their own opinions. Hell, it even extends to sports — I even let my middle son turn into an Alabama fan and that damn near killed me.

Allowing my kids to have their own opinions may be more important to me than it is for most parents because my kids have to deal with having a dad with a public profile. I want them to be comfortable in their own skin and not feel like they have to think a certain way — or even root for a certain team — just because I do.

But I can tell you it would be awful to have one of my sons come home for Thanksgiving after I hadn’t seen him for months and spend the entire time arguing about politics with me. Seriously, it would just be awful. And I think there are a ton of parents reading this right now nodding along.

And I also think there are also a ton of kids reading this right now and nodding along too. I just don’t see the purpose of Thanksgiving or Christmas being to sit around and argue with your relatives about politics. Don’t you get enough of that already everywhere else in society?

So my advice would be to skip the corona and election discussions and just have a good time visiting your parents. There’s plenty of time to engage in debate in the months and years ahead.

Now that can change if, for instance, you’re a college kid home for the holidays and you want to visit your high school friends and your parents won’t allow it because they are afraid of COVID. That’s a big kick in the balls to come back from a college campus where you are free to make your own choices and then you get home and your parents won’t even let you go out with your friends.

That’s a battle I definitely can understand needing to have. And, frankly, it’s one your older brother doesn’t have to worry about at all because he’s an adult with his own life.

You, unfortunately, don’t really have adult freedoms if you’re a college kid home for the holidays.

But barring that situation arising, I’d just chill.

Regardless of what your politics are, we could all use a little more relaxation and a little less fighting over the holidays.

Thanks for reading OutKick and, as always, feel free to send your anonymous mailbag questions to

Written by Clay Travis

OutKick founder, host and author. He's presently banned from appearing on both CNN and ESPN because he’s too honest for both.


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    • I think those “Don’t California My (fill in the blank) slogans are running rampant everywhere, including here in Texas, where Californians are perhaps relocating to more than any other state in the country.

      • LOL I hear ya, James…and as a life-long Bronx Boy (now miles north of Ground Zero)…I just want you to know that a shit ton of NYers north of NYC feel just like you do!!! And if any of us decide to move South, we won’t be bringing Gov. Mutt Cuomo’s beliefs with us…like people in the Hudson Valley – the area where West Point watches majestically over the lower Hudson Region…and the Adirondacks, the Catskills, Roscoe (Trout Town USA), Hammondsport (Cradle of Aviation – Curtiss Wright Aviation), Sherill (Silver City – Oneida Silver), Cooperstown (MLB Hall of Fame), Granville (Granville: “Colored Slate Capital of the World” – is the only place in the world where naturally-colored slate has been mined for over a century), Troy (“Collar City” – is famed for being the birthplace of Samuel Wilson, the inspiration for America’s “Uncle Sam).
        LOL James…I bet you’re saying “WTF did I do to get this infomercial from this azzhole”…but just want you to know NYC is not NY State. Thanks, brother.

  1. Litmus test for the guys wrestling with working toward self-employment.

    1. At the end of the day do you want work to stop, change directions and worry about it tomorrow?(does not mean you don’t bring work home , but that work is attacked then put aside)
    2. At the end of the day are you still working on the business, embracing new ideas, staying up late or getting up early, totally absorbed in ideas to make the business grow?

    #1 stay employed you may not make as much money but you will be happier in the long run
    #2 go for it. You will be happier, and more satisfied working on your dream and vision.

    • I gotta go with #2. Put the work in for 5 years and then you and your co-worker hire a few good employees like you to do the majority of the work. The way I look at it is, you can work 40 hours a week for the next 20 years as employees, or work 60-80 hours a week for the next 5 years as owners. Maybe even find a way to automate most of the daily tasks you do (see The Four Hour Workweek by Tim Ferris as a starting point). If done correctly and you hire the right employees, come up with systems, automate, etc., you’ll actually work much less in the long run.

  2. 20-Year Old from Maryland: Do your parents also acknowledge that Trump essentially saved the economy by opening everything up sooner? I think that’s the counter-argument to all of this. They can either believe the “virus is all Trump’s fault” or that “Trump ruined the great economy with the shutdown” but not both. That’s the problem I have with the Democrat’s arguments. It’s either one or the other, but it can’t be both. For me, I’d rather have the economy back booming.

  3. As a libertarian who leans conservative who is likely trapped in California for the next 12 years (career, wife’s career, and kids) I can’t figure out why people leave this state only to vote for the same crazy policies that drove them out. You can’t whine about Gavin Newsom and Sacramento, then move to Boise and keep up the same behavior, only to expect a different outcome

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