It was a series of fitful yet fateful nights of sleep, amidst leading a massive and failing project, when I’d awake in strikes of anxiety, asking myself some version of the question: Why is work the way it is? 

Providers were upset. Patients waited. Employees wanted to quit, and did, or called-in sick, or said things in frustration to each other. My inbox and voicemail were overflowing with colleagues wanting answers. Word was getting out. And to the top. As in all the way to the top. 

We’d been expanding an existing contact center to allow for centralized appointment scheduling for each of the more than 200 primary care providers employed by the organization. Our project team had a plan, a budget, and a deadline. And we’d been making it happen. Quickly. 

That is until I realized the providers weren’t okay with transitioning their schedules to a standardized template. It’s obvious now, but this wasn’t a realization that occurred in the moment. No. It seeped out slowly and the project withered.

We did the only thing we felt like we could do: abandoned the idea of a scheduling template and attempted to find the solution on the operations side.

It was a disaster.

We made some progress; though mostly limping along implementing just a fraction of what the original vision had been. My confidence as “someone who got things done” was significantly shaken. My ego took a hit. I moved on to a different role in the organization. 

The experience started a professional transition for me that’s only recently arrived at a new beginning. Feeling failure, and feeling like a failure, made me want to explore what the heck went wrong and what I needed to do to prevent it from happening again. 

But that’s a realization I wouldn’t come to for a few more years. 

And little did I know that contact center project—what we were attempting to do, the environment we were doing it in, and the people we were doing it to—was emblematic of what’s happening in organizations everywhere.

A Pattern of Struggle

The new role provided a brief reprieve following the contact center debacle. There was some success. We implemented meaningful programs. I added a few bullet points to my resume. 

But I also experienced more of the same big vision, mediocre results loop playing out. A year later I accepted an offer to do something different.

Or so I thought.

Our boutique consulting company worked with healthcare administrators to implement strategy. We had customers around the country and across the healthcare continuum.

And here’s what happened: I. Saw. The. Same. Thing.

Big visions. Mediocre results.

Projects languished. And not for a lack of effort, or a lack of expertise, or a lack of experience. It was because of the milieu. It was systemic. It was a pattern!

I feel bad sharing I was excited but I was excited! Misery was everywhere! The results were routinely mediocre! It wasn’t just me who struggled to make projects happen—many organizations were struggling to make them happen. The bigger the project, the worse it often was. 

But this too wasn’t a realization that arrived overnight. It was slow. And painful. 

Yet it was this opportunity to see many projects, in diverse contexts, across dozens of organizations, and staffed by a variety of competent professionals that provided the knowledge that failing projects weren’t just a me problem. They’re an all of us problem. 

Failing projects touch everything everywhere and the consequences cascade across our work. Here are just three examples from my consulting travels:

  • We’d agree to a $25,000 project with a departmental leader in an organization with multi-billions in annual revenue and wait six weeks for contract approval and vendor set-up. The project should have been finished by the time we even started.
  • On a twelve-week engagement, for a project that required two working sessions each week, the project sponsor would attend the first several working sessions before bowing out to attend to more pressing matters. Once that happened, other project team members also started missing working sessions to attend to more pressing matters. The project schedule would be extended and extended. 
  • We’d spend the first six (unplanned) weeks of a project listening to team members discovering their workflows and business processes that just a few months before they promised they had been experts on.

It’s not to say any of these realities are wrong or right. It’s just to say they exist and, because of their existence, they create additional problems. 

And it’s our ways of doing things, realities we accept with little consideration, that we navigate to make change happen. It means we’re all attempting to solve problems without even considering the actual problems that are causing the problems we’re trying to solve!

This conclusion—that how we work is the real problem worth solving if we desire for ourselves, our teams, and our organizations to fulfill a vision worth fulfilling—is the one I arrived at as a result of the work experiences I’ve had.

Yet it’s eye opening to consider how much reflection was required to get to it. 

It was time and space that let it happen. I didn’t have an overflowing plate of responsibilities. I wasn’t asked to drink any information from a firehouse. I was only asked to be effective. I was asked to think and learn.

Thinking about our thinking isn’t something our jobs require, nor is thinking about how we work. Turning our thinking into learning isn’t either. But I’ve come to believe we must do much more of it if we want to break the cycle of big visions and mediocre results.

So why is work the way it is?

In a word: complexity

In a few more words: our system of management isn’t fit for an increasingly complex operating environment. 

We’ve come to believe in an approach to managing the work of organizations that actually solves fewer and fewer problems and—this part is crazy—often creates more and more problems as we use it. That’s right: how we work is making work harder.

That’s what I found in more than five years of study and practice—even though once I’d figured out where to look, every available resource says essentially the same thing.

It’s usually a look around your current work environment that allows this picture to be painted.

Consideration must be given to the needs of patients, providers, employees, and the community (or shareholders if you’re working in a for-profit outfit) in a modern healthcare delivery organization and that consideration must be delivered with a finite set of resources.

This is accomplished through an annual cycle of planning, budgeting, and goal setting; then the delivery and monitoring of services; and then the assessment of performance as it relates to the plan, budget, and goals—whether individual, departmental, or organizational. 

It’s a logical approach. It’s so, so logical. In fact, it’s so logical we have a hard time imagining, let alone believing, there may be any other way.

What happens when we work the way we work, an approach they call command and control, is we often promote the opposite of the behaviors organizations actually need from their employees and teams to excel in a complex environment. 

The 737-Max debacle at Boeing is an extreme example. An administration flubbing a pandemic response is another. That situation at Away Travel is also a representative case. And what was going on in the basement of the Children’s Hospital of Philadelphia is another.

These are all examples of managing in a complex environment as if it weren’t. A problem may be solved in the short term—such as in this situation in a healthcare delivery organization—but what happens after that?




Better thinking and learning

Whether or not we realize it, we already operate in complexity. We just do it very clunkily. 

To reduce the clunk, to break the big visions and mediocre results cycle, we must improve our thinking and learning. 

A prescription like this—think and learn better?—is antithetical to our industrialized model of improving performance.

That’s the point.

The annual goal setting and performance review process is a good example here. It’s had, and continues to have, enormous consequences for organization performance while very few of us ever take the time to consider what those consequences might be. 

This method—setting individual goals and appraising individual performance—is followed year after year in an attempt to ensure “alignment” across the enterprise and distribute annual pay increases despite the knowledge indicating our accepted method of assessing performance can be detrimental to the organization’s creation of value.

Sometimes those consequences are significant, sometimes they are less so; the point is they exist, are often more misaligning than aligning, and very few of us have ever stopped to think about it.

I had a boss, one of the best I’ve worked for, share his thoughts: “Show me someone who leads by their annual goals,” he said, “and I’ll show you a bad leader.”

Yes, exactly! But why do we even set individual performance goals if that’s reality?

I’m not here saying that accepted practice when it comes to performance management is wrong, although it wouldn’t be how I’d do things if asked for my input; I’m saying we should orient ourselves around thinking about the consequences of our practices and improving them as a result of our learning.

How we work creates problems. We attempt to solve those problems through a variety of organizational initiatives. This is much of what work is for many of us. 

But these aren’t real problems. They don’t need to be, anyway. They are problems of our own creation and if we worked differently they wouldn’t exist. 

The reason they do exist is because we rarely think about how we work nor use learned experience as an opportunity to change it. We just work. We just use the tools and methods we’ve picked up along the way and hardly ever give consideration to their consequences. 

That hasn’t always been the case. How we work—an improved implementation of command and control—was a creation of some very smart people based in the context of the industrial revolution. They did an extensive amount of thinking and learning to create it. And it worked. Really well. For a long time.

But when we use the tools and methods of command and control management in a complex environment, without appropriate thinking or necessary learning, we’re using them in a way they weren’t necessarily designed for. We’re using them out of context.

A critical realization

Big visions and mediocre results are exhausting personally and detrimental to the organization. 

When we realize it, we can recognize the cause of it, and everything can change. 

For a long time, the most important pursuit of any healthcare delivery organization has been efficiency. It was an important pursuit. Much good has come of it.

But our context has changed. 

We’re realizing our organizations and the environment they operate in are increasingly more complex. And how we work isn’t fit for such an environment. 

In fact, it’s impossible. A CEO can’t make enough decisions to keep the organization operating in an efficient enough manner. An executive team can’t either. Neither can the project leader of a critical contact center implementation.

(Nor is top-down decision making even a viable management choice, for that matter.)

While most organizations will probably be fine, whatever the pace of transition to a more natural way of working may be, the individuals inside those organizations will run themselves ragged trying to keep up with a long list of demands using the existing way of doing things.

We’ll attempt to do more and more with less and less in the pursuit of ever increasing efficiency and solving problems of our own making. 

That is until you decide to make a different choice. A choice to improve your thinking and learning and realize for yourself what I’ve shared with you here through a professional transition of your own.

It’s then you’ll be able to answer the question: Why is work the way it is?

It’s the only way to figure it out.

I did something for the first time this year that you may want to consider doing yourself: a career reviewing and planning session. For myself.

It was a bit like an annual job review. Only that it was conducted by me. And free of bureaucratic rigmarole. 

Started. Completed. Useful.

Why I did it

While most of us have something of a formal assessment for our individual job performance—an exercise which may or may not include the opportunity to discuss where we’re taking our careers—annual reviews from bosses are something of a low-value exercise.

“Telling people what we think of their performance doesn’t help them thrive and excel, and telling people how we think they should improve actually hinders learning,” write Marcus Buckingham and Ashley Goodall in an all-around excellent Harvard Business Review article detailing (with research) why feedback rarely works as well as we’d think it would. 

You should read why for yourself. My summary amounts to this: no matter how hard we try, our feedback to another person is always shadowed by our own biases, beliefs, desires, experiences, and other judgement-clouding realities. 

That’s not so good. And that argument doesn’t even include the fact that these conversations are guided by the organization’s goals—often not aligned with our own—nor the idea that when compensation is connected to assessment, as it too often is, impartial judgement is next to impossible.

Add it all together and it leaves one person truly capable of assessing our performance: us. 

Which is good. Because it’s also us who can best recognize the career path we’re on. 

This year, rather than achievements or pursuits, my path centered on two questions: 1) Why is work (in healthcare specifically) the way work is? and 2) What can we do about it?

Through the Work emerged as an effort to collect and share the answers. And there’s one lesson—perhaps the most important one—worth highlighting here and now and it’s this: learning is central to performing the day-to-day responsibilities of any job. 

If you want to get better at your job or prepare yourself for the next one or just figure out how to be more successful: it’s learning you’re after. So am I. And in this context, doing career reviewing and planning was a natural outcome of that (very important) lesson.

In the end, it was a useful experience I anticipate will be made even more so as the year unfolds. And of course as next year approaches.




How I did it

I once worked for a boss who told me I didn’t know how to set goals. “How can I measure your performance if you don’t know how to set goals?,” they asked.

They, of course, were talking about SMART goals, a framework we’re all assuredly aware of. 

And frankly, I wish I would have answered their question with one of my own: “How will you judge my job performance against goals sure to become irrelevant to the work I’m doing?”

In my experience, SMART goals can actually be quite dumb in a dynamic environment when what is important now may not be in a year. Twelve months is a long time. A lot can be learned. A lot can change.

So while SMART goals have their place, I knew my reviewing and planning required more of an organic approach. Something more in line with Jason Fried’s philosophy and summarized best by this Jim Coudal quote:

The reason that most of us are unhappy most of the time is that we set our goals not for the person we’re going to be when we reach them, but we set our goals for the person we are when we set them. 

Yes, that. 

So I started with a blank sheet of paper and spent nearly two hours thinking about last year and this year, the path I’m on, and how I want to steer it.

Here’s the framework I used:

  • Review; which amounted to asking “What happened last year?” in a few different ways
  • To; thoughts on where I’m going
  • From; connected to the above, and an assessment of where I am
  • How; the ideas for how I can move between the two (From to the To)
  • What Now; intentions for the next 30, 90, and 365 days to make things happen

It worked quite well. Though I’m certain I’ll adjust how I do this in the future because that’s what learning does: helps us find better ways to do things as a result of doing them. 

Although the framework is presented linearly, I didn’t hold myself to working through it in a formal step-by-step manner. That’s just not how the thoughts came to me. 

Instead, I used six sheets of paper (one for each of the above and the sixth for the general/random/parking lot thoughts that came as I went…) and jotted notes in the sections where I thought they belonged.

Here’s how I guided my thinking.


I spent the most time here and asked variations on the question: What happened last year?

I started by thinking about bullet point projects. Those accomplishments I added to my resume in 2019. That led to a number of additional thoughts including:

  • Lessons learned relating to the work I’m doing: what didn’t work, ideas for what could work, themes running through the projects I worked on
  • Highlights from the year and accomplishments, those accomplishments that didn’t result in a resume bullet point but were important nonetheless
  • Lowlights from the year (because those happen, too) and learning opportunities, as they seemed to be related
  • General year-end thoughts and conclusions

Then I used questions to get my thinking moving in different directions and for recalling memories. If I had direct answers to a question, I wrote those down, otherwise they were just for rumination. I suspect the list of these questions will grow over time.

  • What did I learn about myself? What surprised me?
  • What made me happy? What excited me? 
  • What am I proud of since the last review?
  • What were the most important events since the last review?


This was a low-pressure question and I intended for the answers to come easily. Over time I’ve found the “Where am I going?” question can be filled with anxiety, and when it is again, I expect it to be useful to explore that. But I also wanted a question that could just as easily be answered “figuring it out as I’m going.”

Before I began reviewing and planning, I knew there were things I wanted to do and wrote those down right away. I’m also in a place professionally where the immediate next step feels known and evident which means To Dos to arrived without much effort.

Even with knowing my direction in the short-term, it was helpful to gather additional thoughts as I made my way through the Review of last year. It became evident that some themes from last year will continue into this year. It’s impossible to keep intentions and goals, as loosely as that can be defined, contained to a calendar year—so why force that?

In this section I collected a list of process goals and intentions, ranging from the general to the specific. I also summarized my direction with a Moving Toward framework of fast, medium, and slow: categories of speed denoting the intensity with which I’m intending to make the outcome occur. Each category had a single outcome as a means of providing focus, though I don’t see any reason not to put more than one if it feels right. 


This step was about identifying starting points by asking “Where am I?” 

It was an honest assessment of where I am as compared to where I’m going (the To section above). 

There were a few readily available thoughts I placed under a header of “Obvious.” Some thoughts are just that. 

It was also useful to ask: What do I like about where I am? And: What do I like about what I’m doing? The opposite of these questions also were useful. I suspect the answers will help express personal values when I’m making important decisions in the coming year.

Yet the best question I’ve discovered, in terms of identifying present state, comes from Aaron Dignan: “What’s stopping me from doing my best work?” 

Is it my organization? My job specifically? My boss? Me? It was important for me to think deeply about the answers and identify barriers in an effort to navigate them.


To close the gap between To and From, I spent time reflecting on the question “How can I help myself get there?” It was brainstorming in a way; although at least for this reviewing and planning session, my target was the practical and pragmatic. 

My professional goals are concrete at the moment. That made it easier to identify next steps. I don’t suspect that to always be the case. More time in this section is likely required when the professional future is foggier. 

The ideas that were expressed in this section—for the most part—had been rattling around in my head for the past month or so, though concentration on the question did provide additional opportunities not yet considered. It was helpful to put them to paper, especially in consideration of the final step of this process.

What Now

Finally: the actions to make it happen. 

I started by just writing intentions. Most of them are process goals (and those that are outcome goals are within my power to make happen).

Then I used a categorization method of 30/90/365 days for actions to take and projects to deliver in the next month, quarter, and for the year. 

This process gave me the opportunity to make decisions about various possibilities I’d been considering. Projects and ideas always hold the potential to move in different directions and, at times, those options have prevented me from moving in any direction. This exercise naturally forced priority clarification. 

Particularly important to me was identifying professional skills I wanted to improve because of my recent interest in skill development through practice at work. It was easy to identify three.

Everything I had come up with was naturally summarized in five intentions for the year, none of them SMART goals, for which I’ll be able to measure my progress for the year. 

I also wrote a one-sentence theme for the year. That, too, came naturally and was almost the final addition to this section. It was something I built into rather than cascaded down from. 

Finally, finally: Although I didn’t do this, I believe a Stop/Start/Continue exercise could be useful in the future. What are task/behaviors/actions you want to Stop, Start, and Continue?

What comes next

Revisiting the What Now section is important in making this exercise action-oriented as opposed to a useful but ultimately useless exercise.

I created an Evernote note with the information from the What Now section as to make it easy to review. I plan to do that in my weekly reviews (20 minutes every Friday), which I’ve been doing for the last three months, and includes more than just reviewing my thoughts from this exercise. 

As a result of completing this (Personal) Career Reviewing and Planning, I will start monthly and quarterly reviews to revisit my progress toward the intentions and adjust them against my worked experience. Adjustments are inevitable. 

I’m interested in including other people connected to my professional future in this process. I’ll see how that develops. There’s a lot to think about before approaching someone (boss, mentor, confidant, friend, etc.) with an ask related to this process. Too hot to handle this time around.

I anticipate this exercise to get easier and better with additional iterations. Just the act of weekly and quarterly reviews will provide more information for which to review a previous period of time. 

Ultimately, I found the exercise to be helpful and valuable. And its utility will increase with additional reviewing and planning.

Concluding thoughts

I find it unwise to put our career development in the hands of anyone other than ourselves, even those who are obvious supporters. No one has as much interest in our careers than us.

Others can only assist. Our careers are us things. Only we know where we’re going. Or want to go. Or have the ability to figure it out. 

If career development is important to you, then take stock of your situation from time to time and adjust accordingly. 

For most of us most of the time: there’s no greater opportunity to steer your career in your preferred direction than with the responsibilities of the job you’re doing now.

And beginning with a career reviewing and planning session is as good of a start as any.

No one likes networking. Yet we all enjoy the benefit of having a network. And one of the best places to meet new people with similar professional interests outside your usual circle is the networking time during a professional or community event.

The professional or community event (let’s call it PCE from here on out) is a special thing, often for negative reasons, so if you’ve mustered the energy (courage?) to make an appearance, it’s worth attempting to get as much out of it as possible.

I once despised attending PCEs. The thought of attending one made my armpits sweat and a feeling of dread overcame me.

Then I learned to view the PCE for what it is (an event where every attendee expects the relationship building to be transactional and a little awkward) and began attending with a prepared approach to make sure I got out of the event what I wanted to get out of it.

Whether you’re attending a PCE out of obligation, considered choice, or somewhere inbetween, it’s worth optimizing the likely stilted, uncomfortable, and—dare I say it—forced experience of networking for the chance to meet someone you’re glad you met.

There can always be a person-you’re-glad-you-met at a PCE. You just have to find them.

Here’s a thinking guide to assist you in preparing and executing a networking strategy to meet the people you want to meet at professional and community events.

Henry Mintzberg writes that management is “learned primarily through experience and rooted in context.”

It’s truly a cruel irony: the only way to learn how to manage is to manage.

No schooling, no seminars, no conferences can prepare a person to manage. 

Only a real-life management job of actually managing gives you the necessary skills to successfully manage.

That translates into a lot of starts and stops, luck and learning, and successes and mistakes.  

With a bit of failure sprinkled in: missed deadlines, unmet expectations, overwhelming responsibilities, demanding hours, etc., etc., etc.

That’s not even to mention the assholery of bosses, colleagues, and employees.

Sooner or later a certain mix of circumstances will lead to … something: frustration, stress, loss of confidence, anxiety, stress, etc., etc., etc.

I’ve taken to calling these somethings shitty work things. A shitty work thing is just that: a prolonged period of job dissatisfaction stemming from something shitty at work.

Shitty work things are shitty because they get in the way of doing good work—which is the reason we got into healthcare administration to begin with. Being a healthcare administrator is already hard enough. Add a shitty work thing on top and the job can quickly become undoable.

I think shitty work things happen to everyone.

The shitty work things I’m familiar with—friends, employees, me…—were mostly successfully navigated. 

But they were painful. Too painful. Difficult to navigate. Hard to get through.

So I created something to help healthcare administrators experiencing a shitty work thing.

Shitty Work Thing for Healthcare Administrators is like a first-aid kit for healthcare administrators braving a shitty work thing. It’s an email subscription of twenty emails over twenty work days crafted to help healthcare administrators focus on the work, tune out the noise, and find a path out.

I’d like to share it with you. You can learn more here.

Workplace culture is a constant topic in my social circles. 

As more people look for (and find!) meaning and identity in their jobs they are also increasingly holding their workplaces to certain cultural ideals. And it seems the idea of workplace culture being important plays out across generations, not just something important to millennials.

But what I’ve found most interesting is the way workplace culture is commonly framed in these conversations: it’s either good or it’s bad (and often it’s just bad, because that’s what makes it conversation worthy). There’s very little gray.

It’s an analog assessment. Good or bad. It’s that black and white for a lot of people. 

But good or bad as the defacto workplace culture evaluation feels incomplete.

There are logical instances when we can universally apply the bad culture label to the workplace: sexual harassment, bigotry, misogyny/misandry, and generally anything else frowned on by Human Resources or the law more generally.

But outside of that—what’s good? What’s bad? 

Well I think it depends. It’s a matter of personal preference. 

Remember that New York Times exposé on Amazon from 2015?

The article painted the company in a negative light as being a workplace that operates at an unrelenting pace and unsympathetic to those uncomfortable with that reality.

Amazon is an incredibly innovative company. They are arguably executing strategy better than any other American corporation. That type of environment probably provides the right type of person with exactly the opportunity they were looking for. But it’s probably not the place to find happiness at work for those looking for something else culturally. 

So if you were job searching and looking for something other than what Amazon is offering it seems foolish to think you could go to work for them and think it was going to be different for you.

The analog good or bad evaluation of workplace culture is insufficient for the modern workday. 




Perhaps the right way look at workplace culture is through a lens of individual nuance: is the company’s culture right for me?

It reminded me of Austin Kleon’s praise for the “It wasn’t for me” idea when it comes to books (and just about everything else):

I like the phrase because it’s essentially positive: underlying it is the assumption that there is a book, or rather, books, for me, but this one just wasn’t one of them. It also allows me to tell you how I felt about the book without me shutting down the possibility that you might like it, or making you feel stupid if you did like it.

It just wasn’t for me. No big deal.

And “me” changes, so when you say, “It wasn’t for me,” maybe it’s not for the “me” right now—maybe it’s for future Me, or Me lounging in a beach chair in Jamaica, or Me at fourteen.

Workplace culture not as good or bad but as “it wasn’t for me” or “that’s my jam!”

Workplace culture as right for the individual and the individual’s interests, but not for everyone. Think about it.