How's Work?

How we work makes you feel shitty.

Here's what to do about it.

Drew Weilage

A vacation reader for healthcare pros about The Good Work Life

This is for healthcare pros who know something is off at work, because they feel it.

Off like: this isn't what I signed up for. Or: why is it so hard to make anything happen? Or the quiet wish that work was something you don't need a vacation escape from.

Feel familiar?

Most people never name it. They find a reason — a bad boss, shitty colleagues, a toxic culture — and leave it there. Or worse: they start thinking they're the problem.

It's probably not what you think it is.

That's what this is about.

1

Where are you right now? Airplane? A beach? Mountain cabin? Parisian café? Your own backyard with a good book?

However you're spending this time away from work, I'm guessing you didn't completely stumble into it. You planned this. Or at least aspects of it. You thought about what you needed — rest, adventure, time with people you care about … and now you're doing it.

So with a little distance from the day-to-day, a vacation-infused perspective, and a moment to reflect, I'd like to ask you a question.

2

How's work?

It's a question I've been asking healthcare people, in one form or another, for more than a decade.

And the answers are what you might expect, whether I'm talking to people up, down, or all around the hierarchy: work isn't what most healthcare people want work to be.

What frustrates a bedside nurse is different from what frustrates an ops director, and that's different from what frustrates someone working their way to the c-suite. But the underlying sentiment? Remarkably consistent.

It would be inaccurate to say that everyone reports discontent. But not wildly inaccurate.

You too?

3

It was in that first moment back at work, when the vacation glow was still fresh but fading, that the vacation-planning paradox became clear.

I had spent weeks thoughtfully crafting conditions for a perfect escape from work, and the question hit me the way obvious things do: what if we designed our work lives with the same care we design our escapes from it?

By work life, I simply mean: how you feel at work. That's it.

Do you feel good at work?

We devote the majority of our waking hours to professional pursuits, yet typically invest more thought in planning our vacations than in shaping our experience at work over a four-decade career.

This paradox reveals the path: if we can design conditions for feeling good on vacation, we can design conditions for feeling good at work.

4

I know this paradox because I've been there. Frustrated. Stymied. Dissatisfied.

I've also been: Stressed out. Maxed out. Burned out.

And it wasn't until I lucked into a work life that was completely opposite from where I came that I had the space to explore why the experiences at other jobs sometimes felt … not right. This new place supported me, trusted me, valued me. It felt … great. Dare I say, almost what it feels like to be … on vacation.

Work isn't vacation, yes, and this new organization wasn't without its challenges, but after the last two jobs it was as close to vacation-at-work as one might get.

I discovered there are different ways to approach work — that what I'd experienced before didn't have to be because that's just "how work works." And while I could tell you what made it right, here's the thing: what made it right, made it right for me.

What's right for you is available, too.

5

What I've learned from thousands of "How's work?" conversations with healthcare pros just like you is this: "fine" is too often as good as it gets.

In fact, most of the time, for most of us, work feels like the opposite of vacation. It's what we go on vacation to escape from. There's a reason for that.

How we work makes us feel shitty.

That's not anyone's desire, of course. Work hasn't been intentionally designed to make us feel shitty. But it's too often the reality.

"Shitty" is an all-encompassing term to describe the undesired feelings produced by showing up to do the work that needs doing in a system that gets in the way. Irritated. Frustrated. Confused. Angry. Disconnected, disenchanted, drained, depleted. Emotionally exhausted. Defeated. Worn out. Soul-crushed. All the way to complete burnout.

So what's creating these feelings? What's the source of the shitty?

6

It's how we work.

Our work playbook is built on the ideas of Scientific Management, invented by Frederick Taylor, and popularized to very profitable effect by Henry Ford in the early 1900s, among many, many others. Experts call it industrialized management.

Industrialized management = much success.

It created unprecedented efficiency and productivity, and let's be honest, incredible progress, and wealth too, but industrialized management was designed for a world of predictability and standardization.

Healthcare is not that. Not today. The world isn't either. And yes, while standardization has benefits, doubling down on standardization in situations laden with complexity, uncertainty, and constant change can actually serve to make problems worse.

This creates a fundamental mismatch between what the work requires and how we approach it.

Healthcare changed. The whole world, too. But how we work mostly hasn't.

7

By "how we work," I mean:

The automatic ways we approach work tasks: how we make decisions, how we solve problems, how we communicate updates, and the like; most of which we learned by watching others, accepting the defaults, assuming the way things are done is the way they're supposed to be done.

Nobody taught you these patterns explicitly. You've been absorbing them — from school, where you learned to sit in rows, follow instructions, and wait to be told what's next. From your first job. From your first boss, from how the meetings you attended were managed, from what got rewarded and what got ignored. You saw how decisions got made and you adapted. You learned what was worth pushing back on and what wasn't.

Your boss learned the same way. So did theirs. And theirs, too.

Every organization you've worked in runs on some version of the same playbook. The patterns reproduce themselves across teams, departments, organizations, our entire industry. Over time, "how things work" stopped being something you noticed and became something you just … did. Not because you chose it. Because there was nothing else on offer.

These patterns are born from organizational mechanisms anchored in our outdated work playbook — like annual planning, approval hierarchies, and performance management.

These mechanisms control everything: how you structure your day, prioritize tasks, get approval; how meetings run, decisions get made, information flows; even the work itself — documenting care, completing status reports, creating slide decks. The industrialized management playbook is so deeply embedded it dictates your experience whether you see it or not.

But once you do, you see it everywhere.

8

These inherited patterns aren't neutral — they're the cause of the reasons work isn't what you want work to be.

Twenty-minute patient appointments exist not because that's the time required, but because that's what the budget demands.

You attend status meetings not because they advance the work, but because that's how information flows up the hierarchy.

Change happens to you rather than with you not because your input doesn't matter, but because that's how top-down systems operate.

It's why processes slow you down, systems hold you back, and work of questionable value fills your day.

The result? You work harder and feel less impact. You spend more energy navigating systems than solving problems. You drift further from the reasons that brought you to healthcare. And paradoxically, organizations get worse outcomes too.

But we're not here to talk about the organization you work for. We're here to talk about you. Because once you understand what's happening, you can start to shape your experience — even within the prevailing paradigm of industrialized management.

9

While industrialized management has been remarkably successful from an organizational perspective, it destroys the very conditions needed to do your best work in our modern world of complexity, uncertainty, and constant change.

Industrialized management also makes it harder to do your job.

Most of our work today is about solving problems that have never been solved before. Entering a new market. Deploying a new technology. Creating a new care model. Caring for this patient — right now, in this moment, with this history and these complications and this set of constraints that no one has seen in exactly this combination before.

Even when new problems look similar, they're never the same because the context is almost certainly different. This process improvement project is different from the last. So is the budget shortfall. As are two patients with the same diagnosis.

These aren't assembly line problems with predetermined solutions. They can't be. They require your curiosity, your creativity, and your judgment. They require you to think. To respond. To care.

But industrialized management doesn't trust your wisdom. I mean, it does — and it desperately needs it — but it shrouds that wisdom in layers of process, approval, and oversight that prevent the type of problem-solving new problems require.

Here's some of what it does to you as an individual:

Creates internal tensionYou know what needs to be done, but the system prevents you from doing it.
Wastes your expertiseYou have knowledge, but you're required to follow rigid processes even when the situation calls for judgment.
Drains your energyYou exhaust yourself navigating bureaucracy rather than doing meaningful work.
Treats you like you can't be trustedYou navigate layers of approval that suggest you need oversight to make good decisions.
Forces compromises with your professional valuesYou work within constraints that conflict with what you know is right for patients.

This is the tension you're feeling. You need your curiosity, creativity, and judgment to solve problems — you need them to care, too, but the system requires you to please the bureaucracy, often over doing the valuable work you know needs to be done.

Yet the absolute worst part is this: you're treated as an interchangeable part in a machine. That's not only a metaphor. That's the organizing principle work is built on.

Think about that.

You're viewed as a part in a machine. But work today needs your humanity.

10

It was Dr. David Rock who finally connected the dots for me.

Because feeling shitty because of work is not a woo-woo, woe-is-me complaint … it's the natural human response to trying to do value-creating work within a system designed for something entirely different. That's what makes you feel shitty.

Not occasionally. Regularly. It's accepted as normal. It shouldn't be.

Dammit.

And here's the thing — (almost) nobody's doing this on purpose. Your boss isn't trying to crush your spirit. Your organization isn't scheming to make you miserable. The system just pushes everyone — your boss, HR, IT, Finance, you — to work in ways that happen to be incongruent with being human. Which makes it harder to see. And harder to address.

You work hard to make something happen. And the next step requires action from another team, another department, someone else's approval. You wait. You follow up. You nudge. Nothing moves.

You make an exceptional effort over the course of the year — real effort, the kind that costs you something, only to receive a "meets expectations" on your annual review. You're told that's fine. Even good. That the middle is where most people land.

You know the right thing to do for a patient. You can see it clearly. But your boss, or the budget, or the status quo won't let you do it. So you do what the system allows and carry the difference home with you.

These are just three examples. You have your own. We all do.

They're everywhere at work. Often in moments that hit just as hard — you're told your idea won't work, someone schedules a meeting over yours without asking, a decision gets made in a conversation you weren't included in, someone claims your work as their own.

So, yes, work makes you feel shitty. And no, you can't do good work, let alone your best work, when you feel shitty.

Dr. Rock's research identified five social needs. When any of them becomes threatened, your brain diverts resources from the prefrontal cortex — the area you count on for good decision making, clear thinking, creativity, and emotional regulation.

The social threats in modern workplaces
StatusBeing diminished, criticized publicly, having ideas dismissed.
CertaintyReorganizations, unclear expectations, last-minute priority changes.
AutonomyMicromanagement, rigid processes, no input on decisions affecting you.
RelatednessCompetitive social environments, exclusion, working in silos.
FairnessArbitrary decisions, inconsistent rules, politics over merit.

And when you're operating in that state — when you're less empathetic, when you have less patience, when you're working from a defensive position — you make more mistakes, respond poorly to change, burn out …

11

But my argument isn't about not feeling shitty, it's about feeling good.

Think about when work has felt good for you. An hour or two or three of flow. When a full day left you tired yet satisfied. When you were part of a team on a shared mission that made hard work easy. A time when the world around you required your best and you showed up and did the work that needed doing.

Go ahead. Close your eyes. Take a minute and think about it.

And while feeling more like you do on vacation has value in its own right, feeling good at work serves a deeper purpose: professional effectiveness. It's an argument backed by extensive research in management, psychology, and neuroscience.

When the social threats from SCARF become social rewards — when you feel valued rather than diminished, when you have clarity instead of uncertainty, when you have autonomy over your decisions, when you feel connected to colleagues, when you experience a sense of fairness — your brain operates in a balanced state allowing you to do your best work.

And the research extends well beyond SCARF: positive emotions expand your thinking, psychological safety improves performance, and positive work experiences make you more effective. Studies across multiple research streams — from neuroscience to positive psychology to organizational behavior — all point to the same conclusion: feeling good at work enables the clear thinking, creativity, and judgment that solving problems and caring for patients demands.

Your judgment is sharper when you feel energized, clear, and purposeful. Your creativity flows, you're more empathetic, you're a better collaborator. You solve problems faster. You make better decisions. You're more confident. You're better at your job.

The research is absolute and abundant: You do your best work when you feel good.

The Feel Good Factor

That's what I call it.

The Feel Good Factor is this simple truth: You gotta feel good to do your best work.

So if feeling good is essential for doing good work, and industrialized management systematically prevents people from feeling good, why don't we … why can't we … what's the …

Well, that's our conundrum.

13

This is where most people get stuck.

We have come to so fully and faithfully accept that the way we work is the only way to work, we assume there's nothing we can do because fixing the situation requires organizational authority we don't have.

And that's partly true.

Industrialized management doesn't just extract value — it also creates learned helplessness that prevents people from recognizing their own agency.

That's the trap we're in.

Once you realize there's a problem, the responses are predictable. Some give up. Others try a new organization. Still others burn out working against the system. But that's no way to spend a career. The new place often has the same problems. And burnout is not an answer.

14

Which means what comes next must come from you.

Since change is unlikely to come from the top of the hierarchy, you can start to improve your work life from where you are right now.

Your work life can be actively shaped rather than passively endured. No, it's not always easy. And, yes, it requires work on your part. But it's possible. I've seen it happen — with operations directors, project managers, case managers, IT professionals, HR leaders, physicians, VPs ...

When you realize that systems around you are influencing your experience, you can make changes within yourself and within your control — how you think about work and how you do the work — to cope, improve your situation, and influence the system back.

You can make the same choice.

The Good Work Life

The Good Work Life is a choice and commitment to shape your work life instead of enduring it — an exercise of agency within a system you can't control.

It's a defiant attitude toward the status quo. Not hoping your organization will fix things. Not waiting to luck into the perfect job. Not resigning yourself to workplace shittiness as just how it is.

That choice has three elements:

  • A philosophy for how you think about your work life and your agency within it.
  • Five dimensions that describe what The Good Work Life feels like when you have it.
  • A method for shaping those dimensions.

Together, these create the conditions for the Feel Good Factor — the experience where your best work becomes possible, even within the paradigm of industrialized management.

The Philosophy

Your work life is yours to shape, even within systems you can't control. Industrialized management is what you're up against — understanding it reveals where you have agency. What you do with that agency is up to you.

The Five Dimensions

These aren't goals to achieve or boxes to check. They're what's present when work feels good — and noticing which ones are missing tells you why it doesn't. You've felt them before. Maybe not all at once, and maybe not recently. But you know what they are.

This is my attempt to put each into words, but know it will fall short. Your version of each is what's important. Because The Good Work Life is personal.

Worthy Work

Worthy Work is work deserving of your care — of your time, energy, and creativity. Feeling connected to why you do your work is one of the strongest predictors of feeling good while doing it.

For some people, this is their purpose — work provides meaning. For some, this might be about being challenged … and succeeding. And for others, it might be about doing work that's valuable.

And yet most people have never asked whether their work even feels worthy of their care. They do what's in front of them because that's what the job is. The tasks show up, the calendar fills, you move through it. Nobody told you to ask whether any of it deserves your energy. So we haven't.

This isn't about eliminating the tedium or the administrivia. Every job has tasks that just need doing. It's about whether, for example, at the end of the week, you feel that your care went somewhere that mattered to you. Not every hour. Not every task. In the aggregate — was the work worth showing up for?

A program manager started noticing which parts of her work gave her that end-of-day feeling of "that was good work" — and started making more room for it. A pharmacist got clearer on what medication safety work felt like when she was deep in it, and started protecting that feeling. A service line director realized that a day full of back-to-back meetings merely looked productive — and carved out space for the work that actually was.

Same job. Different focus. Better experience.

Powered Perspective

An operations manager felt stuck. The system wouldn't budge, her boss was overwhelmed, and nothing she tried seemed to make a dent. She'd present ideas that went nowhere. She'd identify problems that never got addressed. She started thinking of herself as powerless — someone things happened to, not someone who could make things happen.

Maybe it happened because of a happy hour conversation with a mentor. Maybe it was something she read. Or perhaps it was a podcast or coaching or therapy. But there was a shift, not in the system — in how she saw herself in it. She stopped telling herself the story "I'm stuck in a broken system" and started thinking "I have agency within these constraints." She looked for decisions she could make without approval. She found allies. She experimented with different approaches. Some worked, some didn't. But she was acting.

Acting from the power she already had instead of the power she wished she had. The system didn't change. But her experience of it did.

Powered Perspective is a clear-eyed view of workplace realities combined with confidence to shape your experience within them. It isn't positive thinking or pretending constraints don't exist. It's the opposite, in fact — seeing the constraints clearly, then finding room to move anyway.

Powered stands in contrast to empowered. Empowered means someone above you granted authority. A powered perspective doesn't wait for that. The authority was always yours. The clarity is what you develop.

Prudent Congruence

Prudent Congruence is creating thoughtful coherence between your professional aspirations and what matters to you personally, supporting both achievement and contentment.

One nurse manager set boundaries, stopped coming in early and leaving late most days. It was uncomfortable. Initially she felt like she was letting people down. But she showed up more focused and energized. The boundaries made her more effective.

She'd gotten clear on what mattered to her first. The boundaries were an expression of that clarity, not a substitute for it. And Prudent Congruence isn't just boundaries guidance. Boundaries are a tool. One tool. Prudent Congruence is the deeper questions: what do you stand for, what life are you living, and are your professional decisions coherent with that?

A physician prioritizes dinner with friends every other week. A change management consultant completes a self-reflection program and shows up to work feeling more like himself. A new mom, or a new dad, or even a long-time parent sets work aside in the evenings to be present.

When you protect what matters personally, you show up better professionally. When you show up better professionally, you have more energy for what matters personally.

Enabling Conditions

I've seen this play out repeatedly. I've been this person. Someone feels constant low-level anxiety at work. They know the information, but there's always that moment of panic — where is that data? What did we decide? They scramble, deflect, or look unprepared. The feeling is exhausting.

Most people either live with this stress, blame it on "too many meetings," or find another excuse. But some make a different choice: they change the conditions they're working in.

An operations director creates a simple system for tracking notes and action items — nothing fancy, just consistent tracking. The anxiety disappears. A quality manager blocks the first hour of her day for focused work. An IT director stops scheduling important decisions for late afternoon when his brain is fried. One product manager asks the team to shift a meeting by fifteen minutes to make daycare drop off a little less stressful. A strategy analyst starts a conversation with his boss to find a way to reduce urgent last-minute requests.

Enabling Conditions means recognizing your environment profoundly impacts your ability to thrive — some conditions you can influence directly, others require collaboration or advocacy.

Most people adapt themselves to existing conditions. They try to be more resilient, more patient, more flexible. Sometimes that's necessary. (And sometimes those conditions are so bad, you've no choice but to move on.) But if it's not that, it's worth asking: what if you changed the conditions instead?

Social Support

A pharmacy director was struggling — overflowing work, exhausting politics, no one who understood.

So she reached out to a colleague from another hospital. They started having coffee once a month. Those conversations became essential: processing challenges, testing ideas, remembering why this work mattered.

And sometimes the support is already around you. A colleague of mine was navigating the kind of environment that makes most people shut down — no clear direction, constant leadership changes, layoffs, last-minute shifts in priorities. When I asked her how she kept delivering through all of it, her answer was immediate: the people. The dedicated time she'd carved out to connect with the colleagues who made her feel good through the interaction itself.

Social Support is your network of relationships, both professional and personal, that nurtures your resilience and success at work. Sometimes it's professional support that helps you navigate work better. Sometimes it's personal connection that reminds you there's life beyond work.

Worthy Work, Powered Perspective, Prudent Congruence, Enabling Conditions, and Social Support — these are what The Good Work Life feels like.

These dimensions are qualities of your experience that define the work life you're working toward. The dimensions shift, because work and life shift. What needs your attention now won't be what needs attention six months from now. That's the practice.

The Practice

Feelings have a bad reputation at work. Don't talk about them. Don't show them. Don't touch them. But your feelings are information about your work life.

Feeling drained after a meeting tells you something. Being energized by a project? That's a message. When you feel disconnected from your work's purpose — that may be worth paying attention to.

Feelings tell you where friction exists, where energy flows, what matters to you, when things are good. They're the signal that shows you what needs attention.

So the practice is taking a minute to give time and attention to your feelings, as information, about your work life.

Take a minute. Ask yourself: How's work?

When? Whenever you're willing to answer honestly.

Take a minute in the car before you walk into the building. Take a minute at your desk before the day starts. Take a minute in the middle of the day when you'd otherwise be scrolling.

Some people ask when work makes them feel something. Some ask between meetings. Others ask with their morning coffee. A good time to ask is when something pisses you off. Some people ask multiple times a day.

There's no right time. There's just: How's work? Work with what's there.

Here is what I suspect: you're already spending time on workplace shittiness. The Sunday anxiety. The complaining with colleagues. The mental energy spent navigating frustration.

So yes, The Good Work Life is one more thing. But it's redirecting time you're already spending toward something that can lead somewhere better.

Sometimes a minute is just a moment. Sometimes it becomes ten minutes. Sometimes it's an hour. The practice is taking the time.

And when you take the time, here's what you're doing with it — the method:

Notice

— within yourself, in how your organization operates, in how people work together. What are you feeling? What's causing it? The meeting that drains you. The impacts of annual budgets. The politics.

Explore

— getting curious about what you noticed. Why does that meeting drain you? What about this work feels pointless? What would make it better?

Try a Change

— acting on what you discovered. Small. Specific. Something you can control.

Sometimes you'll move through all three as a cycle. But just as often you'll only notice, or spend the time exploring something from yesterday, or skip straight to trying a change.

Sometimes that change works. Sometimes it doesn't. You might need to try three different things before something shifts. One change might open up possibilities you didn't see before. And sometimes your work life improves just through noticing and exploring — understanding what's happening changes how you experience it, even when the situation itself doesn't change.

Think about how you planned this vacation. You didn't book everything in one marathon session. You thought about destinations over morning coffee. Researched flights during a break. Asked friends for food spots and cool things to do. Small actions accumulated until you had something you were excited about.

That's how The Good Work Life happens, too. Not all at once. Not perfectly. Consistently, over a career, in moments that accumulate.

19

Organizational approval isn't required to begin. You don't need your boss to sign off. HR doesn't need to be involved. You can just start. Right where you are. That's all the permission you need.

Getting started can wait until your return. Because I want you to get back to your vacation … after a few last thoughts …

Here's something I've learned: everyone is making it up as they go. That difficult colleague. Your overwhelmed boss. The executives making puzzling decisions. All of them navigating the current environment with an outdated playbook, sometimes not all that well. It's the reality of working in complexity, uncertainty, and constant change.

Once you internalize this … it's easier to approach workplace challenges with curiosity instead of resignation. You can look for possibilities instead of just problems. You can give yourself permission to try a change.

Yes, it's completely reasonable to be critical of workplace shittiness. And definitely go to happy hour to vent. But when that criticism becomes automatic negativity — when you're closed off to any possibility of improvement — you've already eliminated any chance to make it better.

We're not ignoring reality. We're not pretending individual effort is the solution to systemic problems. But we are taking action on what we can influence.

The Fresh Start

You've got a choice to make.

You can read this, feel that spark of possibility, and then let the swirl of work swallow you again. The system is designed to make that easy.

Or you can make a fresh start and decide to work The Good Work Life.

The Fresh Start gets you going:

Seven practice guides delivered over three weeks. Each one giving you something new to work with — teaching you the method, how to spot systems, how to recover from threats, how to use mission as a lens.

After that: weekly nudges to take a minute. Short prompts to keep you practicing. Reminders that you have a choice. This continues as long as you want it.

When you're back at work, everything you need to begin is there.

21

I started by asking the question I've asked so many healthcare pros like you: "How's work?" Chances are your answer revealed potential for something better.

That answer doesn't have to be permanent.

Not because your organization finally sees the limitations of industrialized management, but because you can actively shape your work experience with The Good Work Life, even within a system you can't control.

And when we meet and have our own "How's work?" conversation — your answer can be different.

That work is now yours.

You gotta feel good to do your best work.

Start here —

www.thegoodworklife.com/fresh-start