Career advice from future me to my grown son (yeah, the one who is now an infant)

As part of my charity running campaign, readers who donated $50 or more were able to dictate the contents of one blog post.  Today’s topic comes from long time RCAT reader, Rich. This is Rich:


Rich asked me to write a letter like it’s in the future and I need to provide career advice to my son Owen who would then be a grown up.   Frankly speaking, it’s a terrible idea. But I am not one to renege* on my promises*, so here’s something sort of resembling what he asked for.

*I initially wanted to use the word “welch” here, but I googled it to find out if it’s actually welch or welsh, and instead I found out I was racist.  So I apologize to all the people of Wales for my near derogatory remark.  I trust you all no matter what.
**Except I might not fulfill anyone else’s blog requests.

Career Advice From Future Me to My Grown Son

Dear Owen,

By now you’re old enough to know most of my life story.  I’m not just “dad,” I’m also the guy that people stop on the street and say, “Hey!  Aren’t you that blogger guy with the beautiful wife who became a billionaire in her late 30s?”  And yes, Owen, technically that is a correct way to describe me, but before I became “just” the trophy husband to your lovely mother, I had a career.  Many careers in fact.  You may not know this, but before that first Rob Complains About Things propelled me to profits in the tens of dollars, I had the following jobs:

  • Paperboy
  • Golf Range Ball Picker Upper
  • Camp Counselor
  • Telemarketer
  • Intern
  • High powered attorney
  • SAT tutor

That’s right, my boy, I’ve done it all, and along the way, I’ve learned many lessons – mostly because I fucked so many things up.  Because I don’t want you to be one of those spoiled billionaire brats, here’s some advice that may help you as you advance through your career:

1.  Don’t listen to anyone else.

You will hear a lot of different things about the “right” thing to do.  In fact, that’s precisely what I’m doing now.  Remember that what’s right for one person may not be right for you.  A wise woman once said, “Don’t go chasing waterfalls.”  Well, that’s the best career advice you’ll ever get (if by waterfalls TLC was referring to money, prestige, or someone else’s approval).

Looking back through old pictures, I’m blown away by how clear my career intentions were. At various points in my life, I made it clear that I wanted to be:

A carpenter:

photo 1

A tiger:

photo 2

and a naked cowboy:


censored for gratuitous penis

Yet somewhere along life’s journey, that path got twisted and turned and tied up in knots, and I ended up trying to fulfill some unrealistic vision of the perfect career.  I’m not sure where that vision came from, but it was misaligned with what my gut was saying to me (and at times that gut was a massive force).

So in a quest for a real corporate career, I wound up in some rather odd places.  My first job was to call mutual fund companies pretending to be someone else so that I could pass judgment on their customer service department.  I was essentially a rogue member of the Jerky Boys (or a humorless corporate behemoth version of the Jerky Boys).

Next, I ventured into the high-powered world of technology as a telemarketing sales rep.  I cold called hundreds of people a day, but spent the majority of my time developing my writing skills by drafting uproarious emails to my friends.

Fed up with the nausea that developed when I told people I was a telemarketer, I left this illustrious career to attend law school.  I’d show them, I thought.  Lawyers are prestigious!!!! Who could hate a lawyer?  I’ll go work for a big law firm and lead a life filled happiness and riches.  Instead, I developed mild cases of anxiety, depression, isolation, OCD, and the Sunday mopes.  That’s when I followed in my old man’s footsteps and became the SAT King of the East.

I hope you get the point here.  Listen to your heart and follow your real passions.  If you want to become

a fireman:


A 1920s paper boy:


A British Guardsman:


Or a Run DMC:


Well, I’m not going to stop you.  Go with it!

2.  Do the things that you want to do.

You come from a long line of entrepreneurs and risk takers.  Your grandmother had a business that was built on a foundation of eggshells (literally).  Your aunt is a Millennial Workplace Expert.  (I know, sounds made up, but it really was a thing back in the Early 2010s).  If you want to be the world’s next great egg painter, then you should.  Don’t worry about what other people will think of your career choices.  If you like it, it will work.

A brief anecdote about your grandfather:  According to legend, Grandpa Buddy finished college and decided to follow in his old man’s footsteps.  Although it seems impossible and contrary to every established fact you’ve learned about the old coot, Big Papa Buddy was at one time going to be a dentist.  That means that he must have taken at least one science class in school.

Well, Big Papa Buddy got so far in his pursuit of a dental degree that he applied, enrolled, and matriculated in Dental College.  Papa Buddy was moving along “the path” until the day the professor introduced them to the drill.  When he started to drill – and take this with a grain of salt because the veracity of Papa Buddy’s stories is always in question – Papa Buddy accidentally drilled right through the tooth he was working on and then through the table in the lab.

Drill Baby Drill

Later that day, Papa Buddy informed your Great Grandpa that the quest for a dental degree was coming to an end.  He became a dental school dropout, spent a brief period of time working in a hippy dippy poster shop in New York City, and then went on to have a legendary teaching career.

The point of this story, Owen, is twofold:  1) Don’t do anything just because I say to or because you think it will make me happy, and 2) Don’t become a dentist or come anywhere near my teeth with a drill.

3)  Embrace the hard parts.

Any time I’ve started a new job, tried to master a new skill, or pursued anything with vigor, there came a time when it got difficult.  Like way more difficult than I had initially thought possible.  When that moment comes, it will seem simpler to take the easy way out.  The “easy way out” can take many forms, but the most common are quitting or stagnating.  If you settle into your comfort zone because it makes your job easier, then I promise you will hit a point where you hate it.  It’s worth fighting through loads of challenges to break through to a level of competency that you could not achieve by staying in your comfort zone.  Another wise woman once said:

Comfort Zone

I stole that from an episode of Girls (who probably stole it from somewhere else).  See, Owen, I’m not afraid to borrow liberally from TV shows with gratuitous nudity and sexually suggestive language.

Anyway, when you hit the point where something gets hard, that’s the point when it’s really important to push yourself to the next level.  If you don’t make the effort at that moment, one of the following things will happen:  You’ll quit; You’ll stagnate; You’ll get bored; Others will pass you by.  All of those are bad options.

Fight the urge to be complacent when you’re “good enough,” and try to be better.  It’s the hardest thing to do because it means stepping out of the comfort zone, but it’s worth it because when you get to that next level, you’ll feel like that effort was worth it.  You will also be really good at whatever you were working on.  I mean, just look at how far my stick figure drawings have come since the beginning of this blog.  Do you think that’s a coincidence?

4.  End on a high note

Sometimes you have to know when to walk away.  Even though I literally just said you have to push through the hard parts, sometimes it’s not worth it.  If you hate something you’re doing, or feel like you’re doing it just to appease the desires of others, or for the money, or for the chicks, then it’s probably a bad idea.  Walk away.  There’s no such thing as career momentum if you’re momentuming towards something you don’t want.

I’m going to take some of my own advice right now, and end this before it gets even longer and shittier than it already is.  So peace out, Owen.  I hope you find a career that allows you to support me and my poker habit when I’m cooped up in that old person’s home eating mashed up peas.

Peace out!

Traveling for Dummies: Anxious, Insane Dummies (part 2)

Yesterday, I started the unofficial Pollak Guide to Air Travel. But then I had to go, so I pretty much stopped mid-sentence. Now, I’m continuing it.

When is it okay to put your seat back?

Travelers everywhere spend countless hours deliberating on the appropriate time to put the seat back while on a plane. Thankfully, I’m here to fill you in on the rules.

Rule Number 1:

If the flight is less than one hour, put the seat back immediately upon take off. The flight’s not long enough to risk not being comfortable. If the flight attendant isn’t watching, you can sometimes get away with putting your seat back before take off. Live on the edge.

Rule Number 2:

If you attempt to push your seat back and the person seated behind you holds the top of your seat to prevent you from doing so, then your sole responsibility for the rest of the flight is to make that asshole as uncomfortable as possible. That means that if he starts eating, you should move your seat back and forth as much as possible. If his knee touches the back of your seat, you should lean a bit forward and then slam your midsection into your seat with as much force as you can muster. If he grabs a magazine from the seat pocket, turn around and glare. If he starts watching Fight Club, tell him that Edward Norton is Tyler Durden. If he gets up to pee, trip him.

He declared war on you. Win it.

Rule Number 3:

During food or beverage service, adjust your seat to maximize your comfort. This is a good time to see if the seat should be up a little more or back a little more. Pay no mind to whether the person seated behind you is balancing a number of fragile items on his tray.

Planes were designed so that trays comfortably hold a 3 oz. cup of soda and two Rolos. The small indent on the tray, which in no way correlates to the size of a real cup, should prevent any spills when you move around. So feel free to make yourself comfortable.

If person behind you eats anything that emits a smell that you don’t like, I recommend the old “pretend you’re looking for something in the overhead compartment and then fall back to your seat with a little extra oomph” gag.

Flying with kids

If you have kids, it’s your job to make them behave while on the plane. It doesn’t matter what it takes: Benadryl, whiskey, poison, whatever. Just don’t let them kick the back of the seat. If they do kick the back of the seat, do something about it.

Here’s what I recommend: After your kid spends five minutes kicking the crap out of the seat in front of him, have the following conversation at a volume loud enough for the kickee to hear:

Parent: Sweetie, did you just kick that man’s chair?
Kid: [no response – either because crying or watching bubble guppies]
Parent: Didn’t I tell you not to kick the seat.
Kid: [no response]
Parent: Don’t bother that nice man sitting in front of you. He’s just trying to watch his marathon of Say Yes to the Dress in peace.
Kid: [no response, kicks seat again]
Parent: What did I just say about bothering the nice man?
Kid: [No response]
Parent: If you don’t behave yourself, then you can’t have any candy.
Kid: But I want candy. CANDY.
Parent: Then you know what to do.
Kid: Fine, I’ll stop.
Parent: Good job. You’re the best behaved child in the entire land. Here’s some candy.


At the end of the flight, the flight attendant will sound a chime indicating that the flight is over. When you hear that chime, immediately jump up from your seat and run to the aisle as fast as you can. If possible, try to squeeze in front of the people one or two rows in front of you. You won’t be able to move anywhere for an hour or two, but standing in the aisle allows you to take up as much space as possible while telephoning your friends to let them know you’ve arrived and that the flight was terrible.

Additionally, your breath is atrocious at this point, so stand awkwardly close to the people who look annoyed that you’re standing in the spot where they would be standing if you followed the internationally accepted etiquette practice of waiting your turn. That’ll show them.

Once you’ve navigated your way through the crowd, remember that you put your bag in the overhead compartment quite a ways from where you are standing. Instead of saying “excuse me, can I sneak by to get my bag,” you should push your way through and then remove your bag with no regard for who it hits on its way out of the bin. If another bag is in your way, do not touch it or help take it down, especially if it belongs to an old person or pregnant woman.


Don’t watch Big Fish while on a plane. I did that once and I started blubbering like a baby.

Safe travels everyone!



Traveling for Dummies: Anxious, Insane Dummies.

Anne and I are going on vacation next week. So I thought today would be a great opportunity to share everything I’ve learned about travel. (Alternate title: Why Anne hates traveling with me.)

Getting to the Airport:

Leave for the airport 7-12 hours before take off. My parents trained me this way so that if you’re involved in a horrific accident along the way, you have time for minor surgery AND can still arrive at the terminal with enough time to navigate a security line slightly longer than those from September 12, 2001.

Cartoon by Rob Pollak get to the airport early


Once you arrive at the airport, stress levels increase. Particularly with the security line. Stare at the other lines to make sure that your line does not result in a security experience thirty seconds longer than someone who checked in after you. As you do that, you should have a running monologue in your head like the one I have:

Did I bring the tickets? Of course, idiot, they just checked them. What if my passport doesn’t get scanned? Will they think I’m a terrorist? What if they put me through that special x-ray machine that broadcasts my penis to the entire airport? Did I remember to put my toothpaste in a clear plastic bag? Shoot, is it 3 oz or 4 oz that’s allowed?

Did I accidentally pack fireworks? Do I still have the tickets in my pocket? I better check again. Maybe I should hold Anne’s ticket too. What if she drops hers? Did my flight board yet? It’s supposed to leave in 5 hours. What if it left by accident? Then what happens?

Am I wearing any metal? Anne, do you have the tickets? Are there going to be enough bins left when I get to the machine? It looks like they’re running a little low. Ugh, the other line is totally faster.

Is that dickwad cutting me? Oh, like just because you have a pilot’s uniform means that you can go in any line you want? Asshole. Where’d the tickets go? Oh, they’re in my hand. Thank god.

Can I bring this coffee with me? Will there be any food on the other side? I can’t see over there. What if there’s not? Will they have the new Golf Digest or the one I already have? Do I need to take my laptop out of its case? I forget. Why is everyone staring at me? Am I sweating? Do I have my wallet? I better pat my pocket to check. The tickets?! Dammit, Anne. What’d you do with the tickets?


Approximately thirty minutes prior to boarding, an airline representative announces that boarding will begin. At most airports, this announcement will be both inaudible and incomprehensible. You will, however, clearly hear the announcements for other flights boarding in nearby airports.

Although boarding proceeds in the same manner for every flight, you should hover right next to the boarding area for the entire boarding period. This allows you to be first through the gate once your designated section boards. Not only will you be closer to the gate, but the people who are actually permitted to board might think that you’re in line and stand behind you. Success! Now you can get through the ticket taker before them and stand in the same exact line on the other side of the gate.

A cartoon by Rob Pollak - Travel guide where to stand when boarding a plane

Overhead Bins:

Once aboard the plane, commandeer an overhead bin wherever you want. It doesn’t matter if it’s close to your seat. Airplanes only have enough overhead bin space for 1/17th of all passengers.

Once you’ve taken up as much bin space as possible, ignore all requests to keep smaller items like backpacks and jackets out of the overhead bin.


As if peeing in a coffin-sized bathroom isn’t bad enough, you have the added stress of navigating the beverage service and other passengers when timing your pee. Once beverage service begins, all bets are off. The flight attendants hog the aisle and never ever leave. So if you kind of have to go, then you should try to go before the drinks come out. The flight attendant may yell at you because you’re never allowed to be when you have to go, as noted by the “fasten your seatbelt” sign. This is just a recommendation – as if seatbelts on flights do anything.

Pay particular attention to the little light that lets you know when the bathroom is empty. Continue to stare at the light until it changes from red to green. In the meantime, identify anyone else playing the same game. You can spot them because they are staring at you while preparing to murder you if you try to get up first. Ignore their threats and hope that there’s an air marshal on board.


Just before take off, the flight attendant will remind you to turn off your cell phone and place your seat in the upright and locked position. You only have to follow this rule if you’re not currently using your cell phone. If you are using your device, it’s just a recommendation.

If your device is off, then you can glare at and judge the E one asshole sitting on the other side of your aisle. You know, the oblivious guy making a tweet before take off. It probably says, “Ugh. STILL on the runway. Jetblue is the WORST” or “JFK —-> LAX.” If you’re not familiar the airport code to airport code update translates roughly to “I’m a douche.”

The garbage collection:

If you’re not 100% focused on the flight attendant, be prepared to sit with your garbage for the rest of the flight. I obtained a copy of the Flight Attendant Training Manual, which reads as follows:

How to PIck Up Garbage from Passengers in Business Class:
Step 1: Remove one garbage bag from the flight attendant staging area.
Step 2: Cover hands with blue latex gloves.
Step 3: Address each passenger by name, make eye contact, and ask if he or she has any trash. Example: Mr. Jones, do you have any trash that I can take for you?
Step 3a: If the passenger hands you garbage, place it into the trash bag and proceed to Step 3c.
Step 3b: If the passenger does not hand you garbage, proceed to step 3C.
Step 3c: Thank passenger by name. For example, say, “Thank you, Mr. Jones.”

How to PIck Up Garbage from Passengers in Coach Class:
Step 1: Run down the Coach aisle as fast as possible.
Step 2: Avoid eye contact.
Step 3: Hold the bag open just enough for one crumpled napkin.
Step 4: Do not touch any garbage so each passenger in the aisle has to hand it to some stranger sitting next to him.
Step 5: Proceed to the intercom system and announce, “We will now begin trash collection for this flight.”

Rob Pollak: American Hero

Although I’m not usually one to draw attention to my own accomplishments, last night I had a moment so life-defining and heroic, that I had no choice.  I had to tell you about how I single-handedly saved New York with the help of three others.

It was 9:00 pm and almost a foot of snow had piled up on the roads.  For many people, the conditions were treacherous, but I learned how to drive a storm when I lived in the tundra of Central New York.  In Central, NY, it’s not appropriate to even wipe the snow off the front windshield until it has piled up to at least 14 inches.

But in New York City, which Central New Yorkers refer to as “the South,” things are different.  The mayor holds a full press conference at the sight of a little kid with a sno cone.  And if we get three inches (god forbid), schools shut down for a week and Whole Foods sells out of bread and water.  But not English muffins or fizzy water.  Who can afford such lavishness in the face of our own demise?

Last night the roads were bad.  Not “we need to plow” bad, but bad enough that a number of inexperienced snow drivers spun out like crazy and freaked out when they had to go up a hill.  I had a good laugh at these people.

By Rob Pollak By Rob Pollak

At least until I hit the spot where the Bronx River Parkway merges onto the Cross County Parkway.  Things had been moving steadily at 15 miles below the posted speed limit up to that point.  But as I approached the merge, traffic halted.  A slight incline in the road caused a few drivers to freak the fuck out, stop, and then rev their tires as fast as they could while not moving.  This created a doubly bad result:  They didn’t move and they turned the drivable snow into a slush-ice combination.

At first, cars sputtered and then figured it out.  But one dickwad in a van started spinning like crazy.  And then he spun some more and some more until he was basically stopped.

All the while, I was sitting in my toasty car listening to a book on tape. My current selection is Willful Blindness:  Why We Ignore the Obvious at Our Peril, a book about, well, exactly what the title says it’s about.  Anyway, right before the insane snow drive, I listened to a chapter discussing the ways people conform to expectations when in a group setting and don’t help others out if a lot of people are around.

With that in mind, I’m sitting there watching these cars literally spinning their wheels (I bet that’s where the term comes from!!), and everyone else is sitting in the car thinking “man, I hope a plow comes.”  But, I was not going to sit around and be willfully blind to accepting that my night was ruined.  I flung open the door and started sprinting past all the cars in front of me.  Five cars to be exact.

Note – it’s hard to sprint in a foot of snow while wearing sneakers.  I almost fell and busted my face/ass.  That’s probably why most people sit in the car.

Anyway, I finally get to the van and start pushing.  Less than a minute later, three other good citizens were by my side pushing the car with me.  If I hadn’t run out there and started pushing, science says that no one would have.  Because we conform to the pressures of society that say it’s embarrassing to get out of the car and go out in the snow.  We may even make the problem worse.  Then everyone will be mad at us.

By rob pollak

Then we pushed three or four more cars up the hill.  Per usual, I was very sweaty.  But I got back in my car and climbed up that hill with no problems of my own.  Thank you Hamilton College for actually teaching me one thing:  how to drive in the snow.

And that’s how I saved America.

Epilogue:  Three of the four cars that I pushed up the hill were in accidents or stuck again on the other side of the hill.  But at that point, I was moving.  So fuck ’em.