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Maybe the most frustrating work conversation is the “generational divide.” This is an evergreen topic that I’ve seen addressed mostly unproductively. We lazily group population correlations and apply them individually. Regardless of how “spot on” a label feels, it’s typically an insult.

One of the things humans do to simplify our lives is to stereotype. For the most part, this is just human nature. It isn’t pretty but we do it all over the place. Race, class, gender, careers, ages, orientation, regions, passions, subcultures, etc. We stereotype because we are cognitive misers. We’re lazy. I’d bet some animals do it too.

It is undeniable that where I grew up, how I was raised, who I was raised by, and the world I was raised in influence who I am. It is also undeniable that I have innate characteristics. The same is true for every member of every generation. Collectively, these traits help define a population, and maybe even a generation. But it’s still going to bug me when you define me by my population(s) and I bet it bugs you too.

I’m a millennial. Huffington Post calls me an Xennial. I also like Iliza Schlesinger’s self-identification as an Elder Millenial, per her Netflix Special. Long story short, I was born in the US in 1983 (Virgo). I included my astrological sign because I think it is about as accurate as my generational definition. I enjoy reading my horoscope and while it might not be wrong, you can’t make any scientific case for its accuracy. This isn’t to say that there aren’t statistically significant trends for every generation. There are predominant beliefs, values, experiences, or modalities operating at the population level. But what about the individual level?

According to the Pew Research Center, there are approximately 73 million millennials. 73,000,000.

Generations: Populations vs. Individuals

One of my favorite courses in college was a 400-level class titled Seminar on Evolutionary Biology taught by Tass Kelso (RIP). Skirting a rant about the definition and misuse of the word evolution… I’ll just say that populations evolve and individuals do not. From an evolutionary perspective, we are snapshots. Collections of genetic material (genotype) physically expressed (phenotype). As much as we mature, grow, learn, and adapt there is a degree to which we are what we are.

Systems Thinking & Generations

Jay W. Forrester was an early computer scientist and the founder of system dynamics. His work at the MIT Sloan School of Management introduced system modeling to the business world, creating the foundation for modern system thinking (I highly recommend Donella Meadows Thinking in Systems).

I bring this up for two reasons, first, systems thinking is a hugely valuable skill. Second, Jay Forrester describes humans as innately talented at finding the leverage point in systems and pushing the wrong direction!

I use this mental model a lot. Humans are constantly intervening in systems and often getting either no response or a negative response. The generation conversation, which comes up a lot, seems like a great example of leverage misapplied.

A popular mental model for teams formation is forming, storming, norming, and performing, otherwise known as Tuckman’s Stages of Group Development. It looks like this:

We’ve all experienced this swoop. It can be seen in sports, a group project, a meeting, family, even just casual interactions.

I think we’ve also had plenty of interactions where there is zero chemistry. In rare cases, this is the base state, there is truly no team potential. Far more frequently it is team members withholding or procrastinating.

Back to the Generation Conversation

So here we are. We know that we stereotype. We know that we are both an individual and a member of a number of populations (including our generation!). We also know we’re likely to label our interpersonal relationships, especially while storming. Do you still think that the difference is generational or are you procrastinating?

I stumble here (and probably always will!) which is why I try to approach the generation conversation as a red flag. Per Jay W. Forrester, I’m at the choke point in the system and I’m probably pushing the wrong way. There is a conflict (storming) and I’m jumping to intractable and offensive labels instead of unpacking the very human interactions that are occurring.

Do we have generational differences? Absolutely. But are you sure they aren’t personal differences?

I’ve been very busy this quarter.

Busy is a word and an idea that I have fought for a long time. It is a boring, trite, and sometimes dismissive way to say that life is full. In less honest moments, busy is a dodge.

One of the larger challenges of being present is knowing what you’re present with. This is the power of gratitude lists, correctly booked calendars, meetings with agendas, and tangible steps towards real goals. You’re pulling back the white-wash of busy and examining what busy really is. The brutal truth that the hustle and bustle might not be worth it.

And yet, we all get busy. We might say yes to too much or have someone say yes on our behalf, or it just happens. Life colludes to stack a set of demands, reschedules, or opportunities to fill your days and nights.

I have two lines of defense for busy. The first is that I try really hard not to say that I’m busy. There are all of the reasons I listed before (boring, trite, and dismissive) and more fundamentally, it is me failing to honor the question.

• “How is life?”
• “How are you?”
• “How is work?”
  

Whatever the variation might be of someone checking in on me, even just politely deserves a better answer than “busy.”

Selfishly, thinking or uttering the phrase “busy” is also a sure sign that I need to pull back, that I need to take some time to assess where I’m at and why I’m there.

I think there is a lot of confusion on what pulling back necessitates. It is vitally important (literally) that you have fun, enjoy hobbies, and invest in your social circles. Life is meant to be lived. It’s also essential for you to get your shit done. Life and leadership are full of dichotomies, this is one of them.

My second line of defense is a little less straightforward. It is a disciplined approach to my calendar and my outcomes. My outcomes come from my goals, my job, and my clients. My calendar, like your calendar, is how I measure time. Time is famously nonrenewable. When I start feeling busy, here are my tactics:

• Commit to a daily planner, update it daily
  • This is not your email associated calendar (Outlook, Google Calendar, iCal, etc.)!
  • Low-tech works
  • I like The High Performance Planner
• Outline your obligations and the things you’ve already committed to
  • Include exercise, meals, and travel time
• Reflect on your other priorities and add them to your daily planner
• Add these blocks of time to your email associated calendar

Day-after-day, week-after-week, I have gotten much more realistic about what I can accomplish in a day. I also have a better record of what’s getting done and not getting done. Most importantly, I’m owning my calendar which is a critical habit of success.

I know I make this sound easy and it has been a serious struggle for me. Per Gretchen Rubin’s The Four Tendencies, I’m an Obliger. I’d prefer to put other people’s priorities ahead of my own with predictable outcomes. I accept calendar invites, say yes, and avoid the non-existent conflict of carving out time on my own calendar.

To adapt to this tendency, I started by adding my bus commutes to my calendar. My next step was recurring appointments for exercise. From there, I highly recommend some experimentation. I tried scheduling regular “block” times, you know 60 to 90 minutes, where I’d be highly productive. The trouble with these blocks is that I need a lot of clarity stepping into them. Setting the expectation to produce, regardless of precursors has been a recipe for disappointment and negative self-talk. What has worked a lot better is to maintain two lists. The first is to-dos with estimated times for large tasks, the second is habits I’m building, like writing (45-minutes, three times per week). I can then drop these blocks into my schedule, honoring my available time, priorities, and my level of energy/focus. Try as I might, I’m not a robot:)

Do I still feel busy at times? Absolutely. The good news is that I have habits to fall back on. Programs I can run that help me grind through the high-priority tasks and keep me connected to my humanity;)

The Farmer and his Horse

You have probably heard the Taoist story, often ascribed to Buddhism, about the farmer and his horse. Here is an excerpt from David Allan’s post on Medium, Who Knows What’s Good and Bad?.

The Farmer and his Horse

“One day his horse runs away. And his neighbor comes over and says, to commiserate, “I’m so sorry about your horse.” And the farmer says “Who Knows What’s Good or Bad?” The neighbor is confused because this is terrible. The horse is the most valuable thing he owns.

But the horse comes back the next day, and he brings with him 12 feral horses. The neighbor comes back over to celebrate, “Congratulations on your great fortune!” And the farmer replies again: “Who Knows What’s Good or Bad?”

And the next day the farmer’s son is taming one of the wild horses, and he’s thrown and breaks his leg. The neighbor comes back over, “I’m so sorry about your son.” The farmer repeats: “Who Knows What’s Good or Bad?”

Sure enough, the next day the army comes through their village and is conscripting able-bodied young men to go and fight in [the] war, but the son is spared because of his broken leg.

[And this story can go on and on like that. Good. Bad. Who knows?]”

Good, bad, terrible, wonderful are all subjective. My highs and lows are subject to experience, perspective, mood, etc. As my life and career unspool, there is plenty of room for both better and worse.

Subjectivity aside, I know two things:

1. I have worked with some fucking awful people
2. This is when I have learned an incredible amount about myself

Terrible Bosses: The Dysfunctional Duo

To date, the worst people I have worked for were the Dysfunctional Duo, a direct manager, and their peer/mentor/manager. I could go on at length about their failings (honesty, ethics, transparency, communication, cronyism/nepotism, fear, pettiness, process, empathy/sympathy, maturity, and professionalism). Instead, I’m going to focus on what I learned about myself. We all know it takes two to tango.

Who & What You Can Change

There is only one person you can change, you. From there, you can change your thoughts, your beliefs, your perceptions, and your actions. That’s it. 

This can get confusing because a small part of us wonders how we can change to get the outcomes we want. There is a fine line between growth/self-improvement and an abusive relationship. I will spend a lifetime learning and relearning this lesson.

Using the example of the Dysfunctional Duo, I was almost always in trouble. I don’t know if I could do anything right, even if we explicitly defined success. I don’t like being in trouble, and like a good employee, I was trying to figure out how to stay out of trouble. Work harder? Work less? Show my work? Hide my work? Over-communicate? Under-communicate? I explored all sorts of variations with no apparent wins. My actions assumed rational actors. Unfortunately, human relationships aren’t rational. What the Dysfunctional Duo didn’t like was me, regardless of how I was showing up. As obsessed as I am with self-improvement, I’m still me. 

Finally, this is also the functional definition of Stoicism and one of the core principles of Jocko Willinck (personal page) and Leif Babin’s book/principle Extreme Ownership: How Navy Seals Lead & Win (Jocko’s TedX talk on the subject here). I study and follow both stoicism (highly recommend Ryan Holiday’s The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living) and Extreme Ownership, they’re game-changers.

Human Resources* Can Be Worse than Useless

*Caveat: There are some fantastic human resource (HR) personnel out there. I think we all know how it feels when members of your profession drag you down.

I think there is some confusion as to what HR’s role is in many organizations. My initial assumption was that HR exists to protect, nurture, and develop human capital. That they’d be looking out for the long-term health of the organization through the organization’s number one resource, staff. I don’t think I have experienced this yet… What I see most is that HR exists to protect the organization and comply with regulations. 

In the case of the Dynamic Duo, I was getting into “trouble” a lot. Early in my career, one of the valuable lessons is that if you’re in trouble, you need to create an agreed-upon action plan as fast as possible, regardless of validity. This action plan needs to address the chief complaint in a measurable and verifiable way with an objective third party, and it’s also good to include some extra credit in the action plan. A senior HR representative is often the best objective third party. Unfortunately, HR reported to my manager’s manager. In business school, we called this “competing commitments.” Long story short, I wasn’t going to get the support I needed, much less wanted from HR.

Big picture, I was exploring the functional organizational chart. Org charts represent hierarchy as defined by title, class, and report structure. Org charts rarely represent the day-to-day functional reality of an organization. Trust, communication, and decisions often flow very differently through an organization than the org chart represents.

My Personal Life

Work and career are a part of my identity, for better and worse. The daily abuse, real or imagined, was taking its toll. There are three areas where I know I struggled:

Mindset

I can be very hard on myself. It’s a terrible habit that I’ve been working on for years. I can toil for hours on what I did wrong to create a lousy interaction or outcome. This has held me back in countless ways. Even with years of therapy, over a decade of yoga, and love of stoicism and Buddhism, I’ve got a lot of work to do here.

The underlying problem is that once I get going, I can keep going. Daily reminders of my shortcomings quickly turned into negative momentum and a negative mindset. This is where I made a huge mistake.

My tripod of stability is exercise, nutrition, and sleep. I immediately started to cut back on all three to dedicate more time and energy to address the surface-level feedback. As you can imagine, this is a negative feedback loop. Worse yet, I knew better.

Stress Management

I manage stress the way most successful people do: exercise, nutrition, and sleep. I also fail to manage stress the way most people do: skipping workouts, finding solace in food/booze, and ruining my sleep. As much as I think it can be productive to hit the self-destruct button on occasion, I was mashing that button way too often.

I was sleeping roughly 5-hours a night. I stopped going to CrossFit. I barely rode my bike. I was overeating. I was drinking too much too frequently (alcoholism runs in my family).

The result was that I was a physical and mental wreck. I was failing to take care of the basics, and it showed with the bags under my eyes, the 20lbs of extra weight, and my capacity to show up as my best self every day. I took it out on myself. Predictably, I wasn’t any happier or any closer to my goals.

Personal Relationships

All of this personal mismanagement made me a pretty miserable person to be around. I was grumpy, obsessed with the work problems, and out of shape. I was shitty company.

This phase was hard on my friendships and my family. It was the worst for the people closest to me, namely my wife. My ability to manage my lows was a direct threat to one of the most important relationships for me. Outside of obvious regrets, this created yet another negative feedback loop. Isolation and neutral/negative relationships only added more stress and prevented me from getting the perspective and support I really needed. 

Accepting the Consequences

One of my strengths is tenacity (stubbornness). An element of tenacity/stubbornness is fear. Fear rarely helps perception and decision making:)

A huge challenge in this process was correctly identifying and weighing consequences. On the one hand, I was arbitrarily punished nearly daily. On the other hand, I was sure that the most significant consequence was leaving this “dream job.” (How I deluded myself into thinking this was a “dream job” is a story for another time…) What we’re talking about here is loss aversion. Loss aversion states that humans interpret losses much more intensely than gains. The kicker is that we also get to define what is a loss and what is again.

In this case, I defined loss as losing this job even if it was 100% my choice. I failed to identify the day-to-day abuse, stress, and all of the challenges it created personally as anything more than the status quo. Despite these perspective issues, the number one thing I had to work towards was wrong or right. I had to accept the consequences of leaving.

Tim Ferriss’s Seven Steps for Overcoming Fear is a great exercise and is mostly what I did. I had to sit down and write out what I was losing and what I was gaining. I had to step away from the human dynamics, the personalities, my emotions, and objectively look at the real consequences and accept them. Regardless of how I felt or what excuses I could generate, it was abundantly clear that I had to leave this job.

I drafted my resignation, slept on it, and handed a signed copy to my manager.

Engaging in Rumors

Almost six months after I had left this job, a member of the Dynamic Duo went nuclear on a nonprofit I was running, purely on rumor. As far as rumors go, we’re talking about the definition of defamation as well as ethics violations that should have ended at least one councilmember’s term. This was bad enough that I was talking to multiple attorneys to assess my exposure (none), recourse (limited), and my next steps (expensive). On rumor alone, I was in deep.

So what do you do? The short answer is nothing.

There is an excellent interview with Steve Jurvetson (Tim Ferris Podcast: Steve Jurvetson — The Midas Touch and Mind-Bending Futures #317). Steve was talking about media rumors and managing the blowback and cited that the best practice is not to engage. To paraphrase, the basic premise is that any interaction adds energy and validity to the rumors/crisis. The best practice, as put forth by public relations professionals, is to do nothing.

While I didn’t know it was a best practice going into this mess, this is mostly what I did. After I had verified what I needed to with attorneys here is what I did:

• I included 3rd party individuals in all meetings and communications (I was fortunate they had clout)
• All communication was via email or well-attended meetings
• I operated transparently
• I communicated promptly, professionally, and only on the tangible issues via written communication
• Aside from a close circle of support, I said very little about what was going on and who was involved
• I cut some key people out of my life permanently

I made it through this with most of my reputation intact. It strengthened some key relationships, destroyed some relationships, and I learned a ton. 

Conclusion

As for the Dynamic Duo, there is a part of me that quips “fuck em” and there is a voice, a little deeper down, that is really sad for both of them.

Who knows what’s good and bad?