Anonymous Mailbag

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It’s Tuesday, which means it’s time for me to solve all the issues in the Outkick universe. (I know it’s actually Wednesday now, but I got caught up in some things so couldn’t publish yesterday).

As always, send your anonymous mailbag questions, anonymity guaranteed, to I can only respond to the questions that I get so if you’re one of the people complaining about all the covid questions then send a non-covid question!

Okay, here we go:

“I just organized a trip for my buddies to the wine country and fronted the money for the food, transport, lodging, etc. In a way, one person paying is easier since you don’t have to do the “I paid for this, you paid for that” math. After the trip, I tallied the bill and sent out the Venmo requests. Let’s say some are quick to pay and some are slow to pay. Question: what is the standard timeline someone needs to pay by once they get the Venmo request (and backup receipts if requested)?”

Ideally everyone would pay within the week. That should be the standard time response. But I think everyone, in a normal request for payment situation, should get you paid within two weeks. After two weeks, I think you could follow up and check on things if you’d like. A month without payment is stretching it. After a month, it’s been too long and you have the right to follow up and find out what’s been going on.

Big caveat here: this is assuming the money is significant to the people involved. That is, this is assuming you need to be repaid the money because it matters to you in terms of your lifestyle. The more money everyone has, honestly, the less significant it is to any of your lives and the longer these things drag on. Because then people just get busy and neglect to take care of it.

Related: your email actually just reminded me that I haven’t paid any of my dues in fantasy football in either of my leagues and we’re almost finished with the seasons. And I bet almost no one else has paid either. That’s not because anyone is trying to dodge the payments, just because everyone is busy.

So my general answer is one week, definitely by two weeks or a month. Unless everyone has plenty of money and then it might take you a year to get your money repaid, if ever.

Good luck.

“I am old-school and believe in hard work. It was the way I was brought up and I continue on this path today, even though I am in my forties. However, it is quite difficult for me to respect the younger generation, which is for the most, very entitled.

I work in the sports industry for a certain four-letter company (been there for over 20+ years) and see people all the time receiving promotions that they don’t deserve. Lots of these promotions also have to do with race/gender. It bothers me to no end. Seeing people hired for these same reasons is also wrong in so many aspects, but I am forced to live with it.

But given I’ve already worked at this company for over twenty years and have a good pension, the so-called pandemic has been sort of a blessing because I am afraid if I was in an office setting that I would have said something and been fired. If I didn’t have a mortgage and a family to feed, I would gladly walk away from this company. Everyone on the outside seems to think this is the greatest place in the world. However, seeing the inner-dealings, it is a despicable place with despicable people all around. I honestly believe a lot of them don’t believe the crap they spew in public.

If we ever return to a work setting (should already be back), I am afraid that my mouth will get me in trouble. Can you offer any advice on how to maybe deal with this? And I know eventually I will be shown the door. Age/race will be the downfall. I firmly believe that.”

At some point many people, regardless of where they work, become captured by their employer. They’ve put in so many years that if they say what they really believe they know they risk being fired. So what happens is many people just sort of put their heads down and try to protect what they already have, the investment in time they’ve made in a company. Eventually most employees end up with kids in college and mortgages to pay so taking a stand against, for instance, woke policies at work comes with far more danger than the pay off is worth.

And, by the way, I think this is even more true for executives.

If you’re a white guy in a highly paid leadership position in a major company right now the only way you lose your job in a non directly related to work error is by not being woke enough or getting caught sleeping with a subordinate — or a series of subordinates — and having her go public. That’s why you saw so many CEO’s sending out their black lives matter emails. Bending the knee to the woke ascendancy was required to keep your job. (Or at least many people thought it was required when all the public pressure rolled in once one CEO started doing it they all felt compelled to do it).

So what would I tell you to do?

I’d honestly probably tell you to keep your head down and keep your job as long as you can.

I don’t know what your salary is at ESPN, but if you’ve got over twenty years of service in it’s pretty unlikely you’ll be able to replicate that salary somewhere else. Plus, when they inevitably decide to fire you or lay you off, you’ll probably get a decent severance package, which will be better than what you could get at a new job.

I’m going to write on ESPN over the weekend, but I think the long range future of ESPN isn’t very promising, honestly.

My best advice for anyone out there who feels like they may be disposable at work — which, let’s be clear, is just about everyone — is to live one paycheck behind the one you make now. That way you should be able to put some money on the side to help cover you in the event you lose a job in an unexpected manner.

Final thought, I think every employee always thinks the younger generation of employees are spoiled. That’s because, in general, living standards and pay have increased over the past several generations.

Over time, at least based on what I’ve seen, the people who work the hardest tend to get rewarded in the long run. Now it may take a long time, I made almost no money in this industry until I was 35 years old, that was a solid decade after I’d started writing online, but eventually your pay tends to follow your work ethic and your talent.

You just have to put your head down and keep grinding.

“I live in a red midwestern state. Our local schools are well regarded but has begun to dip its toes (or at least now they are being caught) in Wokeness. The tenets of CRT are appearing, the superintendent proclaiming the need for “equity” and cop hating, BLM’er teachers being outed on social media. Recently, (2) school board members announced their resignations – one for a legit reason, the other to “focus” on her career. By law they have 30 days to appoint people to the openings.

I have applied for an opening and think I have a decent shot. I have taken precautions such as deactivating my Facebook, making sure my Twitter is not connected to the email address I gave them and made sure to disconnect myself from social media in general since I am guilty of the ultimate sin to the Woke: I’m conservative as hell.

Now, I absolutely plan on being a conservative activist board member if appointed and let’s be honest, once you get dug in to a board spot, you rarely lose unless you do something really stupid. So, if I get appointed, what is my play here? Do I play the shadow game conservative and try to quietly and stealthily fight this nonsense in our schools or do I go scorched earth and try to lay waste to all who get in my way? I would mention that as a Marine, this Woke BS is a fly I’d be happy to smash with a sledgehammer as opposed to a fly swatter but at the end of the day, I want results.”

I think going undercover is the right move for your initial application for the school board. (Most school board members are elected. Are you being chosen to serve out a term pending an election? I think that has to be taken into account here too.)

Because if you have to be elected, I think you need to read your electorate. Right now there is a groundswell of interest in local school boards. And the people who are most interested in voting for school boards are, like me, interested in supporting candidates who are anti-woke.

If you’re trying to get appointed without creating an initial stir, I think going under cover is a good move initially. But once you are running for election, I’d share what you really think.

I may get involved in politics in the years ahead. And if I do, I can guarantee you this, I’m going to say exactly what I think, just like I do now on this website, on the radio, and on TV and video. Because I’ll have the luxury of not needing a political job to make a living as a politician.

One of the things that most disappoints me about the LeBron James’s, Steve Kerr’s and Adam Silver’s of of the world is they’ve all made more money than they can ever spend in a lifetime. At what point do you stop taking profit over principle in your life? For me, it’s shameful that so many athletes continue to bend the knee to China.

“Just got an e-mail that our Christmas luncheon is canceled due to the Omicron variant. When, if ever will this madness stop? We have been working from home for nearly two years (which most everyone likes including myself) but this was a chance to see people from the office for the first time in 2 years.

My question to you  is can we ever expect this sh*t to end, with the first word of a new variant, the usual suspects are in an utter panic. It’s a zero sum game for them. I am double vaccinated, but want life to return to normal as best as possible. And don’t get me started on the masks, which I loathe and the haphazard way the wearing of them are enforced. You can’t be a little bit pregnant, they either work or they don’t. So to wear them walking into the restaurant but can take them off to eat, coaches have to wear em and players don’t. When does this end?”

It ends when the vast majority of our country stops allowing covid to influence our lives.

Covid fear porn has, essentially, ended in red state America. If you live in the South or in any state that voted for Donald Trump you would never know that covid existed at this point unless you’re in an airport.

I spent the entire fall on the road for the Outkick bus tour. The stadiums were packed, the bars were packed, it felt like a 100% normal football season. Other than flying into and out of the airport, there was no sign covid still existed.

My advice to all of you who are fed up with covid regulations is to move to a free state.

If I lived in the northeast, on the west coast or in the Chicago area, I would have left long ago.

The only good thing that may have come from the covid insanity is allowing so many of you to realize you can work from anywhere and be just as efficient.

Finally, if you really want to see some of your co-workers, why don’t you reach out to them individually and set up an event outside of work? Why do you need the company to set it up at all? Take charge of your lives and set up your own event.

Okay, I’m off to pick up my kids at school.

Load me up with questions for the holiday season now by sending your dilemmas to me at

And, as always, thanks for reading Outkick.

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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  1. Amazingly, some suburbs in Covid happy Vermont have rejected mask mandates. And the police chief in one town that did adopt a mandate had said” we have better things to do than enforce this mandate.” The tide is slowly turning against the mania.

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