Writing

The problem with inflection points is that you actually need to get to them.

That's why I used to dislike the term. It presumes something happens almost magically—as in, a pivot point appears, momentum shifts, and suddenly, you're moving forward. But getting there involves what many politely call "a hard look in the mirror" and what I'd describe as recognizing that your old ways of thinking, your accumulated expertise, and your strongly held beliefs are part of the problem.

I've watched this play out so many times. Smart, accomplished people—owners who built a business from nothing, executives with impeccable track records—get stuck in what feels like climbing a sand wall. Every step forward slides back—more effort, hours, and intensity. And somehow, things get more complicated rather than easier. I've spent most of my career getting companies and myself through those moments, and I felt I should attempt to jot down a few observations.

The Map I Was Missing

Before Ordiant, I worked with public companies navigating challenging financial situations. They'd struggle to attract capital, be weighed down by broken capital structures, or face potential restructuring. At night and on weekends, I studied for the CFA, and increasingly, I felt disconnected from what I saw. The financial doctrine I was learning ignored what was happening in boardrooms and executive suites. In hindsight, I saw brilliant people making choices that seemed obviously wrong, but at the time felt entirely reasonable to them.

I started reading outside finance: Kahneman and Tversky, Richard Thaler, Nassim Taleb, and many others. That got me into behavioral economics, psychology, and neuroscience. Thinking Fast and Slow, in particular, felt like discovering a map for territory I'd been wandering through blindly.

The core insight—the difference between System I and System II thinking—explained so much of what I was watching. System I thinking is fast, automatic, relying on heuristics and experience to help us navigate daily life. It keeps us alive and saves cognitive energy. System II thinking is slow, deliberate, and analytical. When choosing a college or evaluating a major strategic shift, you want System II. You want System I when deciding what to have for dinner (unless you're trying to ruin date night).

The problem is that you can't get to an actual inflection point using System I thinking, and that becomes a problem because, in the absence of clarity, history and dogma become the guide.

The Sand Wall Pattern

The slog before the turning point looks like this: Trying old tricks, but harder, faster, with even more intensity. Doubling down on what worked before. Then tripling down. Then, quadrupling down on a strategy that's no longer viable rather than questioning the premise in the first place. And wrapped around all of it is ego, which makes sense when I think about it. For highly successful people, building momentum to the inflection point often requires letting go of an era, a way of doing things, a definition of themselves that's been core to their identity and success.

I'll take myself as an example. Ordiant has been a continuous journey of evolution, driven partly by changing markets, partly by clients pulling me into deeper work across more dimensions of their businesses, and partly by my relentless drive to add value. But the moments before each inflection have forced me to reckon with a hard truth: I can no longer lean on things that worked before, that I had success with, that defined my value. And that's not just about business tactics. It's about self-definition, meaning, and my role in the world.

I've seen this same dynamic with others. The founder who built a company through force of will and bias toward action now needs to slow down and create space for System II thinking. The executive who excelled at operational execution now needs to focus on strategy and people development. The owner, who was the company's greatest asset, is now struggling with the reality that their involvement has become a constraint. In each case, getting to the inflection point requires becoming a student again, which involves exploring new skillsets, new roles, new ways of working with teams, and particularly, an evolving sense of what creates value as technology and markets shift.

There's also fear. Google "decision-making under uncertainty," and you'll find pages on how stress degrades judgment and narrows thinking. The grind to the inflection point can take years and a massive toll on those involved. With more lived experience now, I have an easier time understanding what I was watching years ago when executive teams kept spiraling deeper into challenging positions despite working harder than ever to regain control. They were trapped in System I mode when System II thinking was what the moment demanded.

Root Causes

To me, pre-inflection means you're dealing with undiagnosed root cause issues. A CFO I collaborated with last year introduced me to the "five whys" framework he used internally. For such a simple concept (literally asking "why" five times), it's remarkably effective at helping clients (often owners, and yes, I turn it on myself too) see how they're almost always part of the problem.

Really, it's just structured System II thinking. Here's an overly simplified example:

An accounting team is heavily resisting automation and workflow changes.

Why? They believe the current setup is good enough.

Why? They can't see that it's creating issues for other parts of the organization and holding everyone back.

Why? The company hasn't set clear performance metrics that the department feels bought into or understands how they benefit from greater performance.

Why? Because it's accounting. Why would we need metrics beyond accuracy and timeliness?

Why? Ownership hasn't given the accounting department a compelling reason for improvement or created a value-based performance system that rewards innovation and collaboration.

The underlying issue isn't the accounting team's resistance; it's leadership's failure to articulate purpose, rally the team about a deeper "why", and align incentives.

Most five whys exercises look like this. System I thinking dominates the first couple of answers, and leadership often hasn't dug into the deeper dynamics or put themselves under the microscope. That's not a criticism as much as an observation about how business operates. Quick emails, short Zoom triage calls, task lists underlying project trackers—most business life runs at System I reaction speed. System II work gets viewed as less commercially favorable, a luxury for when things are going well. Yet, most issues and arbitrage opportunities reside in calorie-intensive activities the body is built to avoid.

What Works

I don't exempt myself from this dynamic as I fall into the same patterns. The point is that getting to the inflection point requires roughly these steps across all the integrated issues holding back that moment:

• Understand what's happening by pausing and having substantive conversations—not triage calls but deep dialogue that gets past issues into purpose and meaning, "the why." It's usually best to avoid System I by avoiding conclusions. The point is not to know but to develop questions and a series of hypotheses and a framework for answering those questions. I typically say "I don't know" a lot at this stage, much to the disappointment of clients. In fact, one even blurted out, "But I'm paying you to tell me what to do," to which we had a System I and System II conversation.
• Talk with people in the market outside the company who connect to the issues in different ways: customers, former employees, competitors, and suppliers. Some might call this "discovery," but that word feels deflated. This is more about aggressively getting sharp on the issue, not an academic field trip.
• Develop a system architecture view of how value flows and what's blocking that flow. Usually, this needs to be visualized because the complexity exceeds what we can hold in working memory. The issue is that organizations often think about roles, responsibilities, tasks, and projects rather than systems and value, and they need to move from a construction project mindset to one of engineering.
• Create a game plan and governance mechanism to track improvement with accountability. Don't forget governance! We usually do a lot of work, develop a solution, and then face pushback during execution on adhering to ongoing review around value creation. Over time, I've found that technology can help, and I've found that the clients who have dealt with the most pain during transformation eventually buy into steering committee-style governance, but it takes a bit to get there.
• Return to bias for action, but with checkpoints along the way and a willingness to adjust. Knowledge management and orchestration software can help a lot here.

It seems simple. However, I have not seen many middle-market companies execute steps two through four well, and I haven't seen them either when working on my own business. This is where outside advisors can help, not because they're smarter but because they're less invested in defending past decisions and less constrained by internal politics and self-definition.

I usually find that navigating an assessment of my situation is challenging. I'm guarded about aspects that might hold me back, and I'm slower to admit when I'm wrong than I'd like to be. But working through these dynamics with clients—issues that are far more complicated than my simplified accounting example—has been easier because I don't have my ego or identity wrapped up in their past decisions.

The Challenge

I've reviewed thousands of companies at this point. Met with countless leadership teams stuck or working to break through. And I watch a similar dynamic play out. The deeper gravity of getting to the inflection point is that it's not a technical problem. It's a human one, which often comes with significant debate in which power, incentives, identity, and the search for meaning collide. It would be much simpler if navigating inflections came down to who did the best analysis or argued most persuasively. However, transformation is so hard, and fails most of the time, precisely because it requires people to change what they do and who they are in the business context.

That's the sand wall. And you can't climb over it with more effort. You have to stop climbing and build a different path.

But here's what no one tells you about finally reaching the inflection point: You've just asked your entire organization to let go of the heuristics and playbooks that got them here. You've told leaders their expertise might be part of the problem. You've opened up questions about identity and role that most people would rather avoid. You've created a moment where everything feels uncertain and the old answers no longer work. And it's still just the starting point.

So what actually guides decisions now? What holds the team together when the old playbook is gone and everyone's exhausted from climbing that sand wall? What makes people willing to sustain effort through transformation when they're unsure who they should become on the other side?

That's not a strategic question. It concerns the organization's soul now, which I'll discuss next.