Work is more like a wilderness

Today I'm dusting off an idea I've been exploring for a while—The Transforming, or what it's like to work in an organization constantly reacting to market forces. The Transforming sits at the core of many the most frustrating workplace experiences, and understanding it might just help us navigate the wilderness a bit better.

Hey! Let me be the first to welcome you to The Transforming—the always-happening, always-unfolding state of change in your job, and the continuing result of market forces far beyond our control.

Partly because of how those forces have changed healthcare and partly because of an outdated approach to working in the world those forces have created—how we work is mismatched with reality.

This mismatch creates frictions you’ve perhaps felt: frustration, depletion, disorientation, confusion, a sense of disconnect …

Plus—

I think these next frictions you should share with your boss

—this mismatched approach is the cause of too-slow change, too-siloed work, too-much bureaucracy, and too-much or too-little of whatever else is getting in the way.

While we’ve spent our careers thinking work takes place in an environment similar to a football field, work is actually happening in something more like the Rocky Mountain wilderness, where there isn’t a scoreboard, or an opponent, or even a rulebook for that matter.

But it's not just us adapting to these changes.

The organizations we work for—built for an operating environment of predictability—are also trying to navigate this unfamiliar landscape. And they're responding with the approach that has served them to great success: football field thinking. We see this playing out in familiar ways. A few examples:

• Reorganizations designed to integrate work across departments while maintaining traditional hierarchical structures and reporting lines

• Org-wide transformation initiatives that introduce additional coordination, paradoxically adding layers of oversight and reporting

• Uniform cost reduction efforts across departments and service lines when each are facing unique challenges and opportunities

• External consultants brought in to address emergent situations, working with limited visibility to the broader organization, bypassing the opportunity to build internal adaptive capacity

• "Future of Work" initiatives that apply standardized competencies, traditional performance management systems, and one-size-fits-all development programs to prepare people for an unpredictable future

These decisions, understandable as they are, reshape the terrain of work. This is The Transforming—the ongoing reality of how an organization reacts to market forces reshapes your day-to-day workplace experience. As well-intentioned as these efforts may be, they translate into realities that challenge us:

• Transformation initiatives arrive simultaneously, creating competition for limited resources and overfilling already full plates

• Goal targets land without proportional resources or clear implementation roadmaps, leaving teams to navigate the how along with the what

• Decision-making happens at a distance from the work itself, creating disconnects between strategic direction and day-to-day implementation

• Programs and projects get eliminated, sometimes mid-implementation, as priorities shift or budgets tighten, leaving teams to reckon with undelivered promises

• Documentation and reporting requirements expand continually, often driven by real needs for accountability or compliance, but consuming time that could be spent on more meaningful work

• Team cohesion becomes harder to maintain as people struggle to make sense of constant change, leaving managers and colleagues caught between explaining decisions they didn't make and acknowledging legitimate frustrations

• The definition of valuable work gets murkier, leading us to spend significant time on activities that please the bureaucracy rather than creating genuine value for patients—prompting questions like "surely someone will figure out how meaningless this work is" and then the anxious follow-up: "what happens when they do?"

• Resource constraints force us into continual advocacy mode—competing alongside equally important initiatives and well-intentioned colleagues for the limited support, technology, staffing, or funding needed to deliver on transformation, execute strategy, or simply meet day-to-day deliverables

Those are eight real examples, and depending on your vantage point, you’re likely able to illustrate at least eight more.

These challenges aren't simply annoying obstacles—they're signals that the nature of work itself has fundamentally changed. They're telling us something important: that the playbooks we've been using don't match the territory we're now working in. And what has emerged isn't just a slightly more difficult version of the same game—it's a different environment altogether.

Sure, work has always produced its challenges, it is work after all—but the result is a mismatch between what we know needs to happen and what we're being asked to do or how we're being asked to do it. We experience change fatigue as we sprint from one initiative to the next without time to integrate. We feel the weight of competing expectations that pull us in opposite directions. And perhaps most tellingly, we find ourselves mounting herculean efforts to ensure meaningful work gets done.

This moment isn’t temporary. Even if we might point to the political climate, or the speedy diffusion of AI tools and the hot takes on where it’s going, or economic pressures reshaping business and operating models as the causes of organizational distress—there is plenty of evidence that how things are is … just normal. The market forces shifting the world have been shifting the world forever. We’ve just grown more aware. And more connected. So how work is now is probably how work is going to be for the remainder of our careers.

The leap we need to make—our organizations too—is to embrace working in a wilderness where complexity and uncertainty aren't just challenges to overcome but realities to be leveraged.

Our organizations will eventually figure out how to operate in a wilderness, and figure out how to support a workforce working in a wilderness, too—because the market will force them to, or force them out of business.

And while awaiting that eventuality, which yes, will come with its inconveniences, frustrations, and difficulties, we can make a shift in our own ways of working by transitioning from a playbook approach to one guided by a set of individual behaviors congruent with what our jobs are asking of us.

I call it a field notes approach. It means relying on practical, evolving observations about what actually works in complex and uncertain situations. Field notes are experience-based guidance for a metaphorical wilderness—they're adaptive, updated based on what's useful for a current context, and combine observation with action.

Because it’s not that work in the wilderness is impossible. It’s just ... different from a football field and requires different behaviors than those we’ve learned to use.

Here’s a first pass at field notes for the now of work—hit reply to share your thoughts …

Preamble - Mind your mindset: Choose to be curious, constructive, and adaptable. Your attitude shapes what's possible.

1 - See systems and patterns: Spot how things actually work, both visible and invisible. Understand the connections, relationships, and unwritten rules that shape how work happens.

2 - Take initiative: If you spot something that needs doing, start working on it. It's an opportunity.

3 - Figure it out: Be resourceful in finding a way forward. There's usually a path when you're determined and apply your creativity.

4 - Speak up (with your POV): Share your unique perspective. You see things others don't, and that insight is valuable. Find the opportunity to share it.

5 - Connect the dots and tell the story: Articulate how the pieces fit together and how they're part of a broader arc. Connect to strategy and goals whenever possible.

6 - Try things (with an informed perspective): Try things out, see what happens, adjust your approach. Real experience beats perfect plans.

7 - Tend your network: Build connections across the organization before you need them. Seek perspectives. Your influence grows through relationships and support of others.

8 - Be a translator: Listen to understand. And help others understand, whether it's complicated to simple, strategic to tactical, complex to analogy, from one part of the business to another ...

9 - Share your work: Surface and spread the solutions and practical approaches that have helped you get things done.

10 - Find better ways: Question established practices and work toward better approaches.

11 - Make progress: Focus on consistent progress over perfect solutions. Tomorrow is another day.

Thanks for reading. Hit reply and let me know your thoughts.

How To Work is healthcare-focused work design inspiration (from the experts!) to nudge your perspectives and practices into better alignment with the world of work as it is, and away from what it was. Here’s my take on what we’re working through.