Why “Working Harder” Keeps You Stuck

What I’ve learned about building a life beyond survival and using systems for confident decision-making.

May 11, 2025

[Unobstructed Issue No. 065]

Let’s talk about the bullshit that gets in the way of living your life. The stuff that makes it actually feel like you’re sliding backward throughout each day instead of making progress.

Just about everyone I’ve worked with wants to feel like what they’re doing matters.

They’re chasing whichever version of freedom feels like the key to the rest of their lives… but without ever getting it. Scheduling freedom, financial freedom, creative freedom stay just out of reach, on the other side of the closest hill. While stretching toward it, work keeps them from living fully.

No, I’m not talking about hyper-focused savants knocking down to-do lists like Jenga towers. This is more like working through your list of shit to do and coming to a screeching halt while you try to find the spreadsheet you need. Could be named anything. Who knows which folder it’s in. Or if it’ll show up in search if it isn’t even tagged.

It’s not just a personal productivity problem… it’s an invisible, but firmly imposed, limit.

This frustrating merry-go-round is enforced by the almighty powers above you. What’s worse, they’re not even aware of what they’re really doing or how it actually impacts you. And if they are, they don’t understand the full picture.

Let me show you.

This is like when you try to log into your company’s single sign-on platform but still can’t get to Salesforce. Or, when you try to pull a usage report, but quickly learn that Workday categorizes employees by job title using a different naming convention than the one you use in Sharepoint. Which is normally fine, but is a big problem for this report for some reason.

This is where your original task list, incomplete and growing, mocks you while you bat down pop-up tasks like whack-a-mole at an arcade. And you do all that while the big stuff from today’s list gets pushed to tomorrow’s. And then the next day’s…

Even though you worked late to catch up, like you do all the time.

Over time, I’d watched this happen to coworkers… then managers… and even executives—all without knowing that the their peers were being overrun, too.

This whole discovery started with simplifying the tech that ran my daily work life.

Because I’d tried to dodge this little hot-potato fiasco. Many times, actually. But then I’d inevitably get caught in it, too. So I’d reset and try again only to repeat the whole damned cycle. And, still, I didn’t understand what people meant by, “if you don’t schedule a break, your body will do it for you.”

It doesn’t take a rocket scientist to figure out that I’d crash.

Which, I did. Hard. So I admitted defeat and tried following the “less is more philosophy.” Might as well? I’ll try anything once…

Annnndddd, whaddayaknow: they were right.

Doing less is actually the answer, if it's the right kind of less.

I first learned about the power of “less is more” as a wilderness guide.

And then re-learned it in the 9-5 world climbing corporate instead of mountains (lol).

It came from learning the ins and outs of the software I was using. All of it. Like pulling out the Jenga pieces and putting them back where they were, just to figure out where the weak points were.

Knowing how these things worked, I reasoned, would help me understand what each feature was trying to achieve. That’s how I started stripping away the stuff I didn’t need in the process.

Which then turned into fully reevaluating all of my systems, leading to what is now the foundation of Unobstructed.

This newsletter, Unobstructed, is built on top of a framework that I’ve been designing for years.

I call it the 5 Ps Framework.

Platform
Profile
Publication
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Performance

On one hand, the 5 Ps are a hierarchy for setting up user permissions and software settings. But it’s built to be system agnostic—meaning it’s not tied to a specific piece of your daily tech. It works with… all of it.

But it’s not just a tech manual.

This framework mirrors relational problem solving and workplace autonomy, too. That’s how I came up with it, actually.

Here, see for yourself…

Part 1: Mapping The 5 Ps Framework

You can read a real example of what it’s like to use this framework here, outlined in the order of operations for figuring out your Substack settings.

It’s taken me years to develop this as a solution to the backsliding of day-to-day work.

I’ve worked in restaurants and grown startups.

I’ve driven moving trucks and designed revenue systems for companies, globally. I’ve given mental health keynotes on suicide prevention and run the Boston Marathon after recovering from a traumatic brain injury.

At one point, I built and implemented an enablement program for a billion-dollar company, designing a system that combined SharePoint, Seismic, D365, and Salesforce so thousands of employees could more easily access and send files. I’ve watched teams form, storm, norm, and perform their way to the tallest summits and deepest sink holes.

I’ve even untangled website settings for a client and then given them both a snowboard and a ski lesson—all in the same day. In Jackson Hole’s Corbet’s Couloir, too, no less.

Every role I’ve had taught me something new. All of it’s gone into creating this framework.

Because it isn’t just limited to software. It’s really about getting the fuck out of the quicksand. No more backsliding into a bottlenecked, broken system of can-kicking work. This is about living a life that feels like you’re finally winning instead of always playing catch up.

A full operating system—

That’s what Unobstructed became. It’s a clear path to achievable work and a calmer life.

People are on a sinking ship as tech keeps advancing and they don't know it. Left unchecked, it will have disastrous economic consequences on a global level.

Knowledge work’s accelerating pace means that masses of people will lose their jobs, unable to regain their footing.

It’s a harsh reality I see that we’re nowhere near prepared for. And it’s already happening. As it continues, employer sponsored retirement plans will crumble, among other things.

Annnnd how does this relate to Unobstructed exactly?

Right, ok, so—

Don’t roll your eyes, at least not yet. Read the next three paragraphs and then roll your eyes all you want, deal?

Great—with fewer employees due to layoffs, there will be significantly smaller contributions made to workplace retirement plans, fewer employer matches as a result, and a sea of funds that will suddenly stop returning yields at the rates we’re used to.

It will destabilize the central nervous system of the global economy. Everyone—all of us—should take a moment to really let that sink in.

Here’s why this isn’t just about keeping up with the Joneses.

Our entire society is propped up by the backing of a market made of investment funds… This layoff shift is not about the difference between “being lazy” and hustling your little tushy off. The top percentage of knowledge workers who remain employed will be severely impacted, too. Because everyone’s portfolios will rapidly lose value if the money that would normally go into those funds… stops going into the funds.

While this wave of job loss is happening, the creator economy and solopreneurship space will continue to bloom.

They already are, but this trend will skyrocket further and farther at a very rapid, even disruptive pace. A destabilizing one, driven by desperation. Without solving for the widening gap in work style, this shift will be just as ineffective at helping displaced workers recover their financial footing.

AI and evolving tech are making it easier to complete heavy, arduous work in less time. And it’s great for prioritizing tasks and weighing strategic decisions with data…

But it’s all being built in isolated chunks.

Picture this: an employee loses their job after 8 years at their company. They take their 20 years of industry experience and start their own business.

“First things first”, they say, as they create an account on Squarespace to buy a domain name for their new website. “Oh look! It’s available!”, they exclaim. “I’ll be up and running in no time…”

Well, they actually remembered they’d used Wordpress at their last company. How would they know, the marketing fairy always handled it… Anyway, they’re pretty sure they can figure out how to build a simple website. Transferring their newly purchased Squarespace domain to Wordpress shouldn’t be that hard… They also know growing an email list is important, so they create an account on MailChimp.

Wait—

“How am I going to keep track of what’s connected to what?”, they wonder. That’s when they create an account on Monday dot com, smiling smugly to themselves. “That ought to do it”, they jest triumphantly. The MailChimp templates were a little tricky, but they heard Substack makes things easier, so they quickly sign up for Substack instead. And then Stripe, too, so they can collect payments.

But there’s not really a way to sell products on Substack, so they also create an account on Kit. “IT’S SETTLED”, they finally declare with exasperation. “I’ll write articles on Substack, and then use Kit to share more update-style communications about new offers and things like that”, they reason before concluding, “I can just make an account on Gumroad to sell digital products…”

Which is when their eyes widen… “How the fuck am I supposed to add my new Substack subscribers to my email list on Kit??”, they rage with despair.

Look, maintaining all of that stuff is possible. Many solo creators do it. But figuring it out can be a herculean effort. Many businesses have full teams of people to do different chunks of it.

All I’m saying is that if your coworker, who can’t convert a PDF file, is suddenly faced with trying to do all of this? That person is completely fucked. And they won’t understand why AI can’t do it all for them. Or why it costs alllllll that money to have their neighbor’s daughter-in-law use AI to do it for them instead.

In a lot of ways, that’s where all of us are headed. And it’s becoming more and more true each day.

Part 2: Navigating With The Unobstructed System

I built this dashboard to make my own thinking visible. I’ve always wanted something like Iron Man had—a digital workshop where I could rearrange 3D holographic parts in thin air with Jarvis.

It’s not about KPIs, I swear. This was born because I needed something that didn’t focus only on performance marketing KPIs…

This little baby is really for measuring two main things:

Effectiveness of your effort
Battery life of your people

If the 5 Ps are the map, this thing’s the compass…GPS? Whatever, it’s how I check if I’m going the right way and how much progress I’m making.

It’s a living system. No, I don’t expect you to suddenly do this. Or want to rebuild it your way. I’m showing you how I think because it might help you see your own system differently.

Flipping between trying to get ahead and just trying to survive really, really sucks. And red tape is harder to see when it’s baked into your own system settings.

Which is what I help people navigate.

My whole background has been about helping people figure out challenging situations. In the mountains, in boardrooms, and especially when hunched over my laptop at odd hours, my work has always been about finding the hidden crossover between stuff, under pressure. And then fixing it, also under pressure.

Where I used to exhaust myself in the quicksand, my systems now create space for:

Days that don’t involve red-lining your nervous system.
Sleeping at normal hours, for appropriate lengths of time.
Life outside of work to enjoy with friends & family.

Unobstructed is about blending strategy, storytelling, and systems.

The goal is to uncover the best way to spark progress, without burning out.

I’m building this space to help people challenge how they think, sharpen the skills they use, and uncover the hidden intersections within the problems they solve.

“Wait... a former mountain guide… who now maps tech systems?”
Yep, pretty much.

And yeah, I get it. But it really is the same job… It’s about making sense of risk and finding the best path forward…

Helping folks escape the metaphorical riptide and get back to enjoying the beach—that’s what the Unobstructed ecosystem is about. So work can feel easier, instead of like you're barely keeping up.

Look for what moves you forward, while compounding the effort you put in… without draining your time or energy.

Sustainability is the holy grail.

Don’t you think?

It’s also the puzzle piece that took me longest to find, and even longer to place. I see it as the key to being able to continue doing the shit I care about.

I've long struggled with the idea of work-life balance because I naturally live in pursuit of following my curiosity. At speed. Which is inherently not work-life balance approved.

I'm a very logic-based person (could you tell?). That bothers some people. And it’s off-putting to others. That’s ok. It works for me. And this doesn't feel taxing—I really like doing what I do. So I'm ok with more time spent working, so long as my physical, mental, and relational health don't suffer. Which they have, and which I’ve learned from. Still am, still will, too.

And that’s kind of the point.

I truly believe that my approach—what I'm building here—offers a real alternative to the downward spiral of burnout that's overtaking modern life. Working on solving this problem is what I'm passionate about.

It’s something that impacts people around the world.

I kept seeing other people trapped in the same invisible quicksand time and time again, but no one was naming it or even acknowledging it.

I’ve been working on this whole thing for a long time, knowing that Unobstructed is more than a newsletter and podcast. My mission is to provide a solution: create a bridge for getting across the big, hairy, scary knowledge gap within tech.

Let’s navigate that pile of daily tech tools by mapping out the best strategies for solving huge, unexpected curveballs. I’m even talking about using this modular framework to strengthen skills for personal growth. This is something that’s scalable and adaptable enough to use with big companies and with individuals alike.

I’m truly ecstatic with what it’s become, and where it’s headed next.

Let me put a bow on it.

Unobstructed is a philosophy—a way of making sense of and moving through challenges. To work purposefully and exist calmly. It’s a roadmap for finding leverage to create a life of calm clarity.
No, it’s not a life hack. No magic pills, shiny objects, or any of that low hanging, quick-win fruit everyone seems to put in their smoothies…

This is a complete operating system. And a lens I’ve used to simplify how I prioritize, build, deliver, and reset the burnout bar in every job I’ve ever had.

Anddd… the people who need help with this are the least likely to accept it.

I’d grappled with that for a long time.

It’s how I got here, actually. I recognized those who wouldn’t pay attention to this. Or to me, my ideas, or my services. Because it looks like I’m pointing in the complete opposite direction of where they’re trying to go.

I’m not, but they usually don’t stick around long enough to understand that.

People think they need better software, more productivity books, slicker sales strategies… so that’s what they look for, hustling toward more shiny objects and a heart attack.

That’s where the Unobstructed newsletter came from. Mostly, it was a way to document why I think what I think.

Over time, I figured, people will want an alternative to flexing the hustle muscle. And this way, they’ll find it on their own without any back and forth from me. No salesy, pressurized pitch.

And I started The Unobstructed Podcast because I knew long-form conversations with a cohost like Rachael would pull these types of insights out of both of us. But in more relatable ways than an onslaught of text-based content alone.

This is how I flipped traditional lead generation.

Because most people build an audience and then sell to it, hard. Whereas, I combined demand generation (“I know what that is”) and lead generation (“I know I need it”). So by the time someone’s subscribed to Unobstructed, they’ve already been “convinced”—and they want to be here.

Which makes helping people use this ecosystem much, much easier over time.

This is for helping people work with new and emerging tools, like AI and SaaS products, to empower themselves in a world that’s changing fast.

This impacts career growth, skill development, and financial futures.

Unobstructed is a methodology for enabling individuals to carve out some agency within larger ecosystems. It’s to insulate them from market instability. I truly believe that this thing is a modular approach to onboarding, implementation, and even change management.

No, it isn't a SaaS product, like a Hubspot (at least not yet).

But it IS a methodology like Inbound Marketing.

Which is the foundation beneath Hubspot and the many other tech giants that followed in their footsteps.

Your map to becoming Unobstructed.

If you made it this far, something resonated. So you’re already in this thing with me. And if you want to keep walking the path to achievable work and a calmer life, this is the place to do it. You can learn more about how by reading the Start Here page.

I’ll be sharing more detailed walkthroughs and updates along the way with paid subscribers. Things like progress snapshots, new stuff I’m working on, and resources I’m testing that you can use.

Thanks for being here. Whaddaya say we do something about all that bullshit that’s keeping you from living the rest of your life, huh?

onward.

-dmac

P.S. To get a feel for what it’s like to use this system in action, you can sign up for the Substack, Simplified program to untangle your website and get back to focusing on writing.

Build a life beyond survival mode with simple systems for confident decision-making, from a former wilderness guide navigating AI and tech.

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