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heartless sundays

23 May

“Reality got her. You work your ass off for months; bite your nails, for what? Heinz, baked, beans.”  – Mad Men

Sunday afternoon is one of the most depressing times in my life. Without fail, the looming sunset after a structured workweek and unstructured weekend feels so much heavier than any other.

Something’s going on at a subconcious level. A little nagging pebble is telling me that this upcoming week is not mine. It will be busy, and it will all be on me, but it’s not for me: it’s for my resume, my pockets, my employer, and its mission.

I love work. I whole-heartedly believe that a person at work is embarking on their own holistic fulfillment. My parents taught me that the two things that make up your character are your approach to work and your willingness to eat onions. I hate onions, but they keep pressing the issue.

I love my job. It requires thoughtful effort, the people are smart and kind, and the mission is full of high-meaning purpose. Yet I feel anxiety. This is what psychologists call ‘cognitive dissonance.”’

In The Pleasures and Sorrows of Work, Alain de Botton follows the workday of a career counselor. This is not the same person we all ignored in High School (sorry, Mr. Joyner), but someone who dedicates himself to helping adults re-find their way. The majority of his clients are older, going through a mid-life crisis, and willing to ditch their lucrative career. Maybe ditch it for Broadway, or for an apprenticeship as a woodworker, or to stay home with the kids.

In the end, de Botton is disappointed with what career counseling can offer us. Our species has worked for so long, in such differently skilled yet commonly themed jobs, with such an awesome data set of experience and evidence, yet  all we can tell a High School senior is that he has the organizational skills to succeed in an administrative post in the financial industry.

But de Botton realizes something even more disheartening: as a species, we’ve been fooling ourselves.

“I left Symon’s [career counselor] company aware of the unthinking cruelty discreetly coiled within the magnanimous bourgeois assurance that everyone can discover happiness through work and love. It isn’t that these two entities are invariably incapable of delivering fulfilment, only that they almost never do. And when an exception is misrepresented as a rule, our individual misfortunes, instead of seeming to us quasi-inevitable aspects of life, will weigh down on us life particular curses. In denying the natural place reserved for longing and error in the human lot, the bourgeois ideology denies us the possibility of collective consolation for our fractious marriages and our unexploited ambitions, and condemn us instead to solitary feelings of shame and persecution for having stubbornly failed to become who we are.”

de Botton’s conclusion is a gentler way of repeating the advice I have gotten from people when I tell them my zanier ideas and dreams.

“That’s nice, but just find a good job.”

“First work on getting a steady paycheck, then start thinking about this as a hobby.”

“That’s not how life works, honey.”

These are technically true. Doing something new and boisterous is full of uncertainty, and that uncertainty won’t go away until I succeed (if!).

I’ve listened to this advice my entire life. I went to the college with the best track record I could find. I didn’t change majors because I heard that was frowned upon. I desperately sought a job (any job) after college to showcase how viable of an adult I could be in ‘real-world’ society. I chose safe paths, known paths, for places I had already heard were worthwhile. And everything has turned out fine.

I wish I would’ve chased more rabbit holes–they’re so fun and you always get a good story out of them!

Our generation of parents who bought into the idea that you should center your parenting around boosting your kid’s self-esteem and sense of individual self, certainly didn’t sincerely drink the Kool-Aid. It’s sort of like they gave us standing ovations while we were thespians-in-training, but once the actual play was about to start they told us: “you know what, just read your lines and try not to break the set or bump into other people, ok?”

Now that’s cognitive dissonance. Who and what should I listen to?


The career counselor de Botton followed had in his bathroom (he runs his business inside his home) an Abraham Maslow quote:

“It isn’t normal to know what we want. It is a rare and difficult psychological achievement.”

There’s a question: what do we all want? I thought about this question this past Sunday as the blues dripped down.

Here’s Maslow’s hierarchy of needs. This pyramid encapsulates what we, the human species, need in order to survive. The bottom is pretty self-explanatory, but as you climb the pyramid you start dealing with more nebulous items like “morality” and “achievement.”

What do want? ‘Money’ is certainly not a want; it’s a need, and a pretty boring one at that. Once I make enough money to stop thinking about money I want to stop thinking about money. As long as I have enough to obtain shelter, cloth, and food for myself and my loved ones, I am good. So yes, the bottom two slices are needs.

Do I want my own community: a family, a core group of confidants and friends? No doubt, but this still does not feel like a want. I know I need an authentic social group that gets my jokes and doesn’t mind my accidental farts. Otherwise, I would have to deal with all of that all by myself, and that’s how people go crazy. Yep, definitely a need. That takes care of the middle slice, which=need.

I am starting to realize that the top two triangle slices may be where my anxiety comes from. I’ve been blessed with a lifestyle that has secured most of my needs, physical and social…but what about the soulful? What about my “Esteem” and “Self-Actualization”? I can manage to do without those, but like love, it would be a miserable excuse of a life if I did. I want to achieve Spontaneity on a regular basis, just like I want to eat something delicious right now. But how do I know I’ve obtained that; how can I measure my progress in making those cloudy but important terms come to life?

It’s easy to know what I need to eat and own to survive. I just have to think about it. But everything else can’t be figured with purely mental lifting. It requires heart.

I know what music I love and what morality I raise my arms to, and this sort of gut logic doesn’t come from any mental analysis, but from how my heart beats. Does it beat to a quiet evening listening to Bach, or to an outing with friends in the woods drinking IPAs? Our mind schedules our workweek, our heart schedules our weekend.

No offense, brain, but you get too much floor time.

In things that matter the most to my soul, things that are hard to keep accounting on, the heart needs to be heard much more. Deciding what will make me into a more Confident and Spontaneous being is not something I can find on a grocery list or on my resume. It requires a deeper compass. It requires me to stop thinking in terms of cost/benefit, and just follow the rules of love, which really are the rules of the heart: chase what makes me tingle, gasp, and smirk.

Looking back at every decision I’ve made based on a gut feel, they’ve all felt completely right. Every time I’ve decided to listen to that very hard to articulate but very easy to understand sudden soulful clarity, I’ve moved forward with no regret. It makes sense, because my heart is not separate from my body, and it gets the same information as my brain does, but it follows a different process. It knows and feels, and then decides without hesitation.

My Sunday blues may just be that: my heart trying really hard to be heard, telling me to risk more, experience more, be more, hesitate less. It’s telling me that if I follow what I know is right, I don’t need to think as much. It’s telling me that when I feel anxious, it’s because even though my needs are met, I still haven’t fully chased what I want, and deep down I know that. In order to climb past the base needs and into richer climate–where needs are rooted deeper and need a more principled organ–I need to change the decision-making mix I’ve relied on for everything else. Time to give smirks and gasps a bit more weight. I need to quit being heartless.


the white tuxedo

21 Jun

A small beach town in northern Mexico is a dream vacation for many: sun, tacos, and chill. I was there, but as a native. My first encounters with the much storied young American male were over various Spring Breaks, and many-a beer bottles they hurdled into traffic. It was my life for nearly 18 years. Then, one day, I decided to ditch it for a lovely town 50 miles west of Chicago. Rosarito for Rockford. What a deal.


I got up one morning, surrounded by my family, friends, and authentic food, and woke up a few days later surrounded by a Hilander and a cineplex. In Rosarito life was just today; tomorrow would sorta make sense, maybe, not really. My friends there were great but also a bunch of downers. Their dreams mainly revolved around following their father’s footsteps into butchery, or striving for community college before ever even considering a 4-year just a few miles north. Rosarito was great…for them.


At 17 years old I decided to make it on my own: I got my own place, worked for the man, and paved my way through high school and then college. When people ask me the Whys of that move, I kinda don’t know anymore. All I know is that shying away from this would’ve haunted me forever.


Conan O’Brien may be many things (hilarious/incisive/somewhat obsessed with vulgar animals), but one thing he most definitely is not is a complainer. Not once have I heard him nag or whine over the middle finger NBC gave him. Not once have I heard him nag or whine over the unorthodox and rough path he took to get where he is now.  Some choice quotes:


“You parents must be patient because it is indeed a grim job market out there. And one of the reasons that it’s so tough finding work is that aging baby boomers refuse to leave their jobs…Trust me on this.”


“Nietzsche famously said ‘Whatever doesn’t kill you makes you stronger.”’ But what he failed to stress is that it almost kills you. Disappointment stings and, for driven, successful people like yourselves it is disorienting.”


“[L]ife and the choices I made have changed me in a thousand ways. None of it would have happened if I had rigidly kept my eyes on the prize and decided with great determination to follow my dream, because I didn’t have the slightest idea what my dream was when I was 18. It had to find me.”


My favorite might be his “white tuxedo” metaphor:


“[S]uccess is a lot like a bright, white tuxedo. You feel terrific when you get it, but then you’re desperately afraid of getting it dirty, of spoiling it in any way. I left the cocoon of Harvard, I left the cocoon of Saturday Night Live, I left the cocoon of The Simpsons. And each time it was bruising and tumultuous. And yet, every failure was freeing, and today I’m as nostalgic for the bad as I am for the good.”


(Plenty more of these here.)


My white tuxedo was comfort disguised as success. Staying in Rosarito, sipping margaritas on the beach, and working as the junior manager at the local licoreria could definitely be someone’s version of success. Not mine. I didn’t know what to expect when moving away from things I knew and loved, but I knew what to expect if I stayed. I would’ve had a great tuxedo, but stashed somewhere deep in the closet, away from the real world and its messiness. It would’ve been a waste of damn good cloth. Thankfully, I reminded myself dirt can come off, and tears can be repaired.



make value

26 May

Will it push the ball forward? Are you making work, or making progress? Pick your cliche, but the gist of our professional–and even personal–existence is value. Introducing, creating, and delivering it.


This isn’t a motto just for work. Our lives are all tied up in value production and destruction. Being a good father brings value to your child’s life; plugging away at work, doing the routine minimum, and feeling our soul shrink a little bit each day destroys value.


We are happier when we are creating something enduring, for ourselves or others. We have been built to build: tables, relationships, organizations, ideas.


Create value today and tomorrow. Our value does not go away when we do. It becomes our legacy.



new curiosity

17 May

I’ve used this platform to write about various topics, but mostly politics and the tangled topics therein, for over 2 years now. I am prouder of some posts than others…and quite ashamed of a handful (I wrote that?). But overall, this space has let me write it all out, vent a bit, and think through keyboard taps. To be honest, it’s even been therapeutic.

That’s why I’ll keep writing, on a more consistent basis, and keep this space alive. But…


I’ve come to find a new curiosity/passion/obsession. You know something else is spinning your pistons when your reading selection is to brim about it. Over the last few months, I’ve become engrossed by this question:


How can we like work?


The corollary question would be: why is job satisfaction so important, yet so elusive?


It’s become a sort of unquestioned truth. Because work sucks, that’s why. Not true. Some people have jobs that make them happy. Research shows that most of us are happiest when AT work. Most moments of “bliss” happen during work hours. Our job satisfaction rate is the lowest ever since we began recording these numbers. Technology and innovation have given us a plethora of job/career choices, yet our misery at work continues to rise.




What is this reality leading us to?


What can we do to like our professional lives?


I’ve begun digging into the topic, and have essentially honed in my energy on this crucial, yet often overlooked question mark. This is not just about work, but about our psyches, society, communication, motivation, self-improvement, legacies, families, wealth, happiness, and history.


  • There are 8,700 hours in a year; if fully-employed, we spend at least a fourth of that time at work.
  • The people we spend the most time with a week are our co-workers.
  • Our bliss or lack thereof at work follows us to our families and friends.
  • Growing old also means looking back at our professional legacies.
  • Our dreams and talents grow or fade with the work we dive into.
  • Great work is done by great people, but sometimes great people never know what work will reach greatness.


So from today on, this blog will change focus. I may still write about politics here and there (and believe me, my passion for that will never fade), but this space will be dedicated to starting a discussion on being happy in your professional life.


I hope you will still tag along and contribute. Unless you are Jim Gaffigan or Ricky Gervais, monologues suck, so please stir the pot/add your two cents/any other cliche that’s in style


Here we go…



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