My Philosophy on Work and Problem Solving

I have spent a lot of time inside messy problems: websites that do not convert, CRM systems routing leads to nowhere, reports that technically answer a question but say nothing useful. Most of my career has been that. Not building from scratch. Finding what is not working and improving it.

Over time, a few books, a lot of reps in the gym, and a lot of trial and error have shaped how I actually approach problems. This is my attempt to write it down.

1. Being Stuck Is Part of the Process

I have learned, slowly and usually the annoying way, that being stuck is not the same thing as failing.

That idea hit me hardest when I read Zen and the Art of Motorcycle Maintenance. Pirsig writes:

"Stuckness shouldn’t be avoided. It’s the psychic predecessor of all real understanding."

That sentence landed differently than I expected. Not mystical. Not decorative. Practical. Because I had spent years treating being stuck as a problem to escape rather than information to read.

Something is unclear. Something is not working. Something feels off. The answer is almost never to panic or rush straight into activity. The answer is to slow down enough to see the actual problem. The details of my work change (technology, marketing, design, websites, analytics) but that approach does not.

2. Most Work Is Troubleshooting

Most work is troubleshooting.

That sounds unromantic, but I think it is true. A website that is not converting is a troubleshooting problem. A CRM routing leads badly is a troubleshooting problem. A design that looks fine but feels wrong is a troubleshooting problem. A sentence that says the right thing but has no pulse is a troubleshooting problem.

Even personal discipline is troubleshooting. Why did I not do the thing I said I would do? What broke in the system? What needs to be made easier, clearer, or more honest?

The mistake is assuming every problem needs a different personality. I do not think it does. Most problems need the same basic process: slow down, look closely, test assumptions, remove what is not true, make the next useful correction.

3. Care About the Work

Pirsig’s idea of Quality has probably influenced me more than any business book has. He writes:

"A person who sees Quality and feels it as he works is a person who cares."

Quality is not making something look nice. It is not perfectionism either, which is often just fear wearing a decent jacket.

Quality is attention. It is the willingness to stay with a problem long enough that the cheap answer starts to embarrass you. In design, quality might mean the page finally feels balanced. In writing, it might mean the sentence finally says the thing instead of circling it. In technology, it might mean the system does what people actually need, not what the requirements document claimed six months ago.

Is this useful? Is it clear? Is it honest? Does it work in the real world? That is the standard.

4. Attack the Problem, Not Around It

Ryan Holiday's book The Obstacle Is the Way is built on a line from Marcus Aurelius:

"The impediment to action advances action. What stands in the way becomes the way."

The instinct most people have — myself included — is to find a workaround. Reframe the goal. Wait for more information. Blame the constraints. Redesign around the hard part instead of through it.

But that usually just delays the problem. The hard part is still there when you come back to it, except now you have less time and more sunk cost.

The better move is to go straight at it. Not recklessly, but directly. Figure out exactly what the obstacle is, treat it as the actual work, and move through it. Nine times out of ten, that is faster than whatever the workaround would have been.

5. Small Corrections Compound

The gym taught me this more than any book did. I started training seriously about a decade ago. What it gave me was not a physique. It was a way of thinking about improvement. You cannot fake the reps. You cannot think your way into strength. You show up, you practice, you recover, you adjust, and you repeat.

Benjamin Franklin tracked his own version of this with thirteen virtues (Order, Resolution, Industry, Sincerity, Humility) and graded himself on them weekly. In his autobiography, he writes about the system with a kind of cheerful honesty about how often he failed it. That stuck with me. Not the virtue list. The fact that he kept a system at all, kept showing up to it, and did not pretend improvement happened any other way.

The corrections are small. They compound. That is the whole thing.

6. Reality Has to Be Allowed in the Room

Ray Dalio’s version of this is what he calls radical transparency. In Principles, he puts it simply:

"Pain + Reflection = Progress."

The pain is the dashboard that is broken, the website that is confusing, the lead routing that is bad, the copy that is weak. Good. Now we know where to start.

That does not mean being harsh for sport. It means telling the truth early enough that the truth is still useful. I would rather find the problem when it is fixable than protect everyone’s feelings until the machine is smoking.

7. Keep Going

Start with reality. Do not flinch from being stuck. Find the real problem. Care about quality. Make the next correction.

None of this is original. Pirsig figured it out on a motorcycle trip. Aurelius figured it out running an empire. Franklin figured it out with a notebook. I figured it out on a deadlift platform and inside enough broken websites to fill a graveyard.

The method is not the point. Sticking to it is.