Writing

Over the last thirteen years, I've helped dozens of companies navigate their most important periods of transformation. Then I had to navigate my own.

In 2023, my biggest client filed for bankruptcy.

It was not a slow decline but a board vote that moved to Chapter 11 reorganization, which dropped me into the unsecured creditors bucket with months of frozen receivables. I'd advised distressed companies, so I understood the mechanics. It still hurt, particularly after years of working seven days a week and often through the night, along with many others involved, to create a better outcome. The relationship was intact, but the impact was meaningful.

That was just the beginning. Within months, other clients began wrestling with liquidity problems. I'd find myself on calls with owners sixty, ninety, sometimes 120 days late on invoices. "I'm good for it." "Stick with us." "It's just timing." And I'd keep us moving forward, working late most days to help solve their challenges while their struggles pulled me away from business development.

I'd built a fortress balance sheet for moments like these. But knowing you can withstand pressure and living through it are different things. The following two years were brutal. However, towards the end of 2025, I'm writing this from the other side, partly to consolidate a few core principles from that phase.

That period led to significant growth and a deeper connection with this type of work. For example, one CEO told me this spring: "I'd never trust someone who has not been through a similar experience to advise us." Earlier at Ordiant and throughout my career, CEOs and CFOs would talk about their frustration with advisors without skin in the game or who have never truly been in their arena. It’s easy to guide from a purely cerebral place. It is another to have earned the stripes to do so.

Learning to Love It

I was a high-level cyclist growing up and in college. The sport combines the subtlety of strategy with extraordinary suffering. Becoming great meant moving past the joy of riding, past wanting to win, and embracing the simple act of pushing your body past its limits. Towards the end of my cycling career, I focused mainly on that because there were too many other non-controllables to get hung up on. My mind would narrow to the next training ride, following the plan my coach and I created, tracking the results, and analyzing my power meter data post-ride. That flow became the sport. Whatever happened from there, I learned to let go of it. It was monastic, and I found a deeper drive by removing the noise.

That mindset translates well to navigating big, tough inflection points.

I often joke with clients when we face a significant challenge or reach for a big goal, and I've been doing this long enough now to mean it: "I love this." For whatever reason, saying you can't get enough of the issues and obstacles triggers a different mode in the mind, not one facing a problem. Still, one must overcome a defining moment with everything in balance.

I'm convinced that inflections are about turning the struggle into fun, even 'play.' Yes, there is the strategy and all the rigor around the minutia. However, developing a mindset interested in the problem and enjoying sparring with it creates a sense of freedom to find the solution.

I started to learn about the power of that a decade ago. In 2015, I led a client engagement when energy prices cratered. We got unstuck when I let go of a sense of control and enjoyed the daily grind.

I never looked forward to lining up at the starting line during my cycling years. I still don't enjoy the beginning of a significant transformation. But channeling your mind into the issue and saying out loud that you can't get enough is a hugely helpful way to begin building momentum.
Like a long race in the rain, big tough inflection points expose weaknesses you didn't think you had.

Where Analysis Stops

In my last piece, I wrote about reaching the inflection point and the "sand wall" where old ways of thinking become the problem. I described the shift from System I to System II, which is required before you can begin.

Yet analysis doesn't save you when you're at the point of inflection.

It doesn't start with more meetings, another consulting engagement, finding the right investor, or the next head of fill-in-the-blank.

It starts with stopping.

Stopping means precisely what it sounds like. You pause execution—the firefighting, the constant motion that creates the illusion of progress. It’s critical to clear the calendar for a few days, and I mean actually clear it, not "move some things around."

Increasingly, I’ve felt that starting begins with asking deep questions.

Not "What should we do?" but "What do we actually believe? What are we trying to preserve here? What would we sacrifice to achieve our big goal?"

It's natural to struggle to pause. Yet the best transformations I've seen all started with leadership finding the courage to look at each other, and tell the truth about where they are, where they're struggling, what they believe and do not, and why.

Over the last few years, I've moved significantly away from left-brain analytical thinking about how to move through big, tough inflections. Not because analysis doesn't matter—it obviously does. But because people involved are under immense pressure and often can't make purely rational decisions.

I couldn't think my way out when I faced my own. The rational moves involved diversifying clients, raising prices, and cutting costs. However, executing those moves while maintaining relationships, preserving quality, and staying true to the work that built the business required a completely different approach.

These days, I evaluate inflections from lenses beyond the typical strategy, finance, operations, organization, and governance toolkit:

Emotion: What do people actually feel versus what they say in meetings?

Incentives and alignment: Both conceptual and economic. Who benefits from the status quo?

Power and hierarchy: What leaders are doing versus what they're saying.

Shared purpose: How do we bring different teams together during these periods?

Mapping these areas out, while time-consuming, creates another sort of financial model by which you can begin running scenarios, albeit with more fundamental drivers in mind.

Organizational Soul

Transformation requires redefining meaning and purpose. The closest word I've found is "soul," another way of saying service.

When you're deep in an inflection, when the old playbook is gone, when everyone's exhausted from climbing the sand wall, and the path forward isn't clear, what actually guides decisions? What holds the team together?

I've found that transformation endures or fails based on whether the strategy is rooted in identity. Not identity as a marketing exercise, but as an honest reckoning with what drives the organization at its core, which is about getting into the essence that made it valuable in the first place. I often talk about the feeling a customer has when interacting with the company, and how employees experience signing in and logging off at the beginning and end of the day. Elements of that most fundamental role often hurt pre-inflection in some way. The job early on involves finding that core value again because it’s easy to breeze past and miss what matters most.

What I’ve Learned

Getting through my own inflection—navigating those years when everything that could go wrong did—made me a far stronger advisor and investor.

I didn't walk away with secret techniques, but I understand viscerally what leadership teams and owners experience when they're in it. The fear. The exhaustion. The moments when they question whether it's worth it.

Companies that make it through aren't necessarily smarter or better capitalized. They maintain shared purpose when everything else fails. They build teams that can withstand extraordinary pressure because they believe the struggle means something.

And I also believe that great teams, like great companies, refuse to quit and will find their way to the inflection point. And with momentum comes new forms of complexity.

Next: M&A Illusions – Why most acquisitions fail and what the ones that work have in common.