When the plan breaks: pain, injury, and the numbers that keep you grounded

On Sunday, I did something that was over 10 years coming: I ran a marathon.

In hindsight, I might be using the term “run” loosely, but that wasn’t the plan. I didn’t have the race I wanted.

I went in with a goal of 4 hours and 30 minutes, putting me about a 10-minute/mile pace. I’d done the training and everything pointed to it being possible. The first few miles of the race, it felt… possible. Not easy, but possible. The kind of “I can hold this if I stay disciplined” possible.

Then by mile 8, I knew it wasn’t going to be that day. I started getting lightheaded, and a training injury I had re-aggravated three weeks earlier came roaring back.

By mile 10, my calf on the non-injured leg started cramping. (95% humidity didn’t help.)

And that’s when the race turned into a loop:

Run until I cramp, then walk until it clears.

Run, cramp, walk. Run, cramp, walk.

At first it was every quarter mile. Then it turned into every half mile. Then it got a little better and I thought I was going to be able to run in… and then my quad cramped.

I don’t know that I’ve fully processed the day yet, but I know one thing: I’m proud of myself for persevering. I’m proud I took on something hard and finished it, even when the plan broke early.

As I thought about that day, I thought about many different scenarios I've run into through my work as a fractional CFO.

The business that seemed like all was good, then one day it broke, and chaos ensued.

The business that was doing great, but that great led to things breaking and questions of whether they’d make it through.

Businesses have these stages too. Feeling good at mile 3 or 4. Struggle but hope at mile 8. Then all hell breaks loose at mile 10.

All businesses hit these “hard miles.” You don’t lose because you hit the hard mile. You lose because the hard mile breaks your perspective and your plan.

For some, that breaks their decision-making. Their motivation.

And it breaks the system underneath them, usually right when they need it most.

In business, the “mile 8” moment doesn’t come with cramps. It comes with:

• a customer paying late when payroll is due
• a surprise tax bill
• churn you didn’t expect
• a key employee leaving at the worst time
• a marketing channel drying up
• a margin squeeze you can’t “effort” your way out of

Nothing about that list is rare, but normal operator life. The question isn’t whether you will hit the hard part, but what you do when you hit the hard part.

That’s what I want to unpack in this article: Three mindsets that keep you grounded in the hard part, and the financial tools that support those mindsets so you don’t end up making expensive decisions out of fear or pride.

MINDSET #1: PERSEVERE > PERFORM

When I realized my 4:30 wasn’t happening, I had two options:

• treat the day as a failure, mentally check out, and choose to either quit or limp my way to the end.
• adjust the definition of “winning” and preserve enough to finish

When the plan breaks, you either preserve or you spiral, and business is the same. A lot of owners are still “performing” for the outside world long after their situation has changed.

They keep trying to run the original pace:

• the same overhead
• the same payroll
• the same customer mix
• the same pricing
• the same optimism

…even though the conditions are different now.

Perseverance isn’t pretending the plan is intact. Perseverance is understanding the trouble you’re in and finding a way to stay in the game long enough to make the right adjustment.

Finance translation: perseverance requires preservation.

If you don’t have cash, margin, and working capital flexibility, you don’t get to “persevere.” You get forced into decisions.

This is why, as boring as it sounds, the simplest preservation metrics matter:

• Cash runway: how much time you actually have (not how much you feel like you have)
• Gross margin reality: how much error you can absorb
• AR truth: who is paying and when (not who “should” be paying)
• Cuts: what do we need to cut now to make it to the next day, even if it hurts us long-term?

If you want a clean question to ask in a hard season, ask this: “Do we have enough room to keep moving without doing something desperate?”

If the answer is no, the move is not “try harder.” The move is “preserve” first, by taking the immediate actions needed to give yourself more time to make more long-term adjustments.

MINDSET #2: PAIN VS INJURY (DON’T BE DELUSIONAL)

Sometimes you’re in pain and you should keep moving.

Sometimes you’re injured and you need to stop.

Understanding the difference is hard and often unclear, but ultimately determines success versus failure. Pain is part of growth. Injury is a warning light.

In my race, discomfort was expected. It’s a marathon. But an injury flaring up, plus cramping, plus lightheadedness? That’s not just “this is hard.” That’s “something is off.”

Business has that same distinction, but it hides better.

Pain can look like:

• a tough quarter where demand softens
• slower pipeline because a channel changes
• a temporary cash squeeze when timing gets weird

Injury can look like:

• consistently weak gross margin (you can’t deliver profitably)
• a cash conversion cycle that keeps getting worse (you’re “growing” but cash keeps disappearing)
• AR aging that slowly creeps up month after month
• a business that requires the owner to operate in constant emergency mode

One person’s pain can be another’s injury if other conditions are different, too. That’s what makes all this so hard.

The numbers don’t care about your ego, your optimism, or your story. They care about what’s true.

To understand if we’re just in pain (and will get through) or if there is injury (and more drastic changes are needed), here are a few simple things to understand:

• Trend review (3–6 months): Is this a one-off hit, or a consistent direction?
• Unit economics check: Are we pricing and delivering in a way that works?
• Working capital check: Are we funding customers, or are customers funding us?
• Break-even clarity: What revenue do we need right now to cover the floor?

A simple rule: If the model is broken, grit isn’t the answer. The model has to change and change quickly.

MINDSET #3: OPTIMISM + NUMBERS (HOPE WITH GUARDRAILS)

This week, I recorded a podcast with Clifton Sellers, and there was a moment that stuck with me. We talked about losing clients, the “valley of despair,” and the feeling of being counted out. When I asked him what got him through that moment, he said:

“And my wife and children… My wife actually looked at me during that time and she said, why are you still doing this? … I looked at her and I said, I just can’t quit again.”

Then he followed it with this line: “What if we don’t? What if we just win?”

I love that because it’s honest and human, but it also resets the mindset from failure to success.

You need optimism to build anything meaningful. If you don’t believe there’s something on the other side of the hard part, you stop trying. And if you stop trying, you guarantee the outcome.

But optimism without truth is expensive. It turns into denial, and denial delays decisions until you’re forced into them.

This is why I think the best operators carry two things at the same time: hope they can figure this out and the truth of “here’s what is real right now.”

That’s where Clifton did it right. They didn’t just say, “let’s go win.” They took that mentality and turned it into action. They built systems, professionalized their service, and didn’t hesitate to hire coaches where they needed to learn.

They displayed the right mixture of optimism and perseverance, while understanding that what they were going through was just a flesh wound… pain.

But what I actually love about their story even more is that for so many others, a similar scenario has been an injury.

That’s where this gets really messy. There is no one answer for all.

So the only thing we can do is work on our mindset and DO THE WORK.

From a financial perspective, we need to have the tools in place before we need them. That looks like:

• A 13-week cash forecast: this will help you understand money in and money out and see the cash picture with enough time to react (instead of react).
• Simple scenarios: run a base case, downside case, and “walk it in” case to pre-make the decisions that need to be made before the “fog of war” sets in.
• A weekly money meeting (15 minutes): Create reports to go over in a meeting where you talk about cash, AR, upcoming obligations, and top risks. This helps get everyone in the same room and on the same page.
• A disciplined close: closing quickly (and accurately) gives you your numbers quick enough to actually be used to make decisions from. Without a good close, you’re running of your bank and guesses.

Optimism is what keeps you moving. Numbers are what keep you honest while you move.

WHAT TO DO WHEN THE PLAN BREAKS (A PRACTICAL CHECKLIST)

We are all going to go through hard seasons and unexpected hardship. During those times, we don't get better through self-loathing. That is one thing I'm disappointed in myself about during the marathon. I reverted to a self-loathing attitude even though I told myself I was going to stay positive before the race.

So while I made it through, that attitude impacted my ability to persevere.

To avoid the same pitfall in our businesses, try this simple reflection sequence:

1. Name what broke. The plan? The market? The team? The story you had in your head?
2. Redefine “winning” for this season. Is the win survival, preservation, simplification, rebuilding?
3. Separate pain from injury using trends. Don’t build a narrative from one bad week.
4. Check unit economics fast. If margin doesn’t work, nothing else matters.
5. Build or update a 13-week cash forecast. Give yourself visibility so you can make calm decisions.
6. Set “cramp rules.” Pre-decide what you stop doing when cash is tight (hiring, spend, nice-to-haves).
7. Choose one action in the next 24 hours. One real move that creates clarity or preservation.

I’m thankful I ran the marathon. I’m thankful it wasn’t perfect. I’m thankful the hard part showed me where my mindset still needs work.

Because the hard part is where you learn and how you grow. It’s where you see where the plan, or your mindset, wasn’t up to standard.

It's easy to go through life in business always seeking bliss. But our goal isn't to never hurt. Our goal is to grow and get better along the way. It’s only through actually experiencing some difficulties that you can do that adequately.

Our goal should be to expect those hard times and know we've done enough preparation to get through them with the minimum amount of unnecessary pain. When I say unnecessary pain, I mean pain that we inflict on ourselves that was not necessary to learn the lesson that needed to be learned.

And when we've gone through it like this or maybe even when we've gone through more unnecessary pain than is necessary, as long as we keep moving without breaking the business, we've accomplished the ultimate goal of business: don’t die.

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