Schleps, Puzzles, and Packages: Solving the Problem Problem

Everyone wants to solve problems. Far fewer people want to think carefully about which problems to solve. This is the problem problem: the meta-challenge of problem selection that sits upstream of everything else. Get it wrong and you can spend years producing brilliant solutions to questions nobody needed answered. Get it right and mediocre execution still generates outsized returns, because the problem itself was doing most of the work.

There are three archetypes of problems worth understanding before you commit your finite time and energy to any of them.

Schleps

Paul Graham coined the term "schlep" in the context of startups, but it applies everywhere. A schlep is a problem that is tedious, unglamorous, and annoying to solve. It involves paperwork, regulations, difficult customers, physical logistics, or some other form of sustained unpleasantness. Nobody fantasizes about solving schleps. Nobody writes breathless blog posts about them.

And that is exactly why they are valuable.

The defining feature of a schlep is that the difficulty is not intellectual. It is emotional and logistical. Most smart people unconsciously filter schleps out of their problem-selection process because the work feels beneath them or simply unappealing. This creates a systematic market failure: problems that would generate enormous value if solved remain unsolved because the people capable of solving them do not want to touch them.

Think about it. How many industries are still running on terrible software, broken processes, or outdated infrastructure - not because better solutions are impossible, but because building them requires wading through regulatory complexity, legacy systems, or customer segments that are not fun to work with? The answer is: most of them.

Schlep blindness - the unconscious tendency to avoid seeing tedious problems - is one of the most important cognitive biases in problem selection. It is not that people evaluate schleps and reject them. They literally do not see them. The filtering happens before conscious evaluation begins.

The best opportunities are often invisible not because they are hidden but because they are boring. The mind slides off them like water off a windshield.

Puzzles

Puzzles are the opposite of schleps on the glamour axis. A puzzle is an intellectually interesting problem with an elegant solution waiting to be discovered. Puzzles attract talent. People want to work on puzzles. Academic careers, research labs, and the more prestigious corners of the technology industry run on puzzle energy.

The appeal is obvious. Puzzles are satisfying. They reward cleverness. Solving one feels like an achievement in a way that slogging through a schlep does not. And puzzles are important - genuine intellectual breakthroughs come from people who are deeply engaged with difficult puzzles.

But there is a trap. Because puzzles attract so many smart people, they are also the most competitive problem space. The ratio of solvers to problems is high, which means the marginal value of one more person working on a popular puzzle is often low. The tenth team working on a trendy machine learning benchmark is adding much less value than they think, because the problem was going to get solved regardless. They are drafting behind others and calling it innovation.

The other puzzle trap is mistaking difficulty for importance. A problem can be fiendishly hard to solve and also not matter very much. Academic incentives often drive people toward technically difficult puzzles whose solutions have no practical significance. This is not a failure of intelligence. It is a failure of problem selection - choosing based on intellectual appeal rather than impact.

Packages

The third archetype is the package: a pre-bundled solution to a problem that someone else has already defined. Packages include franchise models, template businesses, consulting frameworks, best-practice playbooks, and the vast ecosystem of "proven" approaches that promise to reduce the risk of entrepreneurship and decision-making.

Packages are attractive because they lower the cognitive cost of problem selection to near zero. You do not have to figure out which problem to solve or how to solve it. Someone has already done that work. You just execute.

The limitation is equally obvious. Because the problem and solution are pre-defined, the upside is capped. You are, in essence, renting someone else's strategic thinking. This works fine when the package genuinely fits your situation and you are content with package-level returns. It fails when the pre-bundled solution does not match local conditions - when it is too thin, in the language of thick strategy narratives, to handle the specific complexities of your terrain.

The deeper issue with packages is that they train you to stop thinking about problem selection entirely. Once you get comfortable operating within a package, the muscle for independent evaluation atrophies. You lose the situational awareness needed to recognize when the package is no longer working or when a far better opportunity is sitting just outside its boundaries.

The Problem Selection Matrix

These three archetypes suggest a way to evaluate any problem you are considering:

Schlep score: How tedious and unglamorous is this? High schlep score means fewer competitors and potentially greater value, but only if you can sustain motivation through the unpleasant parts.

Puzzle score: How intellectually engaging is this? High puzzle score means it will attract talent and attention, which creates competition but also potential for breakthrough solutions.

Package availability: Has someone already bundled a solution? If yes, you gain speed but lose upside and strategic independence.

The sweet spot - and it is rare - is a problem with high schlep content, moderate puzzle interest, and no available package. These are problems that are valuable enough to solve, interesting enough to sustain engagement, and unattractive enough that you will not face much competition. They exist in every industry. They are just hard to see because schlep blindness keeps filtering them out.

Why Schleps Win

Here is the uncomfortable arithmetic. In a world full of smart, ambitious people - and our world has more of them than any previous era - pure puzzle-solving is increasingly commoditized. If a problem is intellectually interesting, many people are already working on it. The expected marginal value of your contribution is low unless you have a genuinely unique insight or capability.

Schleps, by contrast, remain systematically underserved. The emotional barrier to entry functions as a moat far more durable than any technical barrier. Technical moats erode as knowledge spreads. Emotional moats persist because they are rooted in human psychology that does not change with the technology cycle.

This does not mean you should only work on schleps. A life of pure schlep-solving is grim, and intrinsic motivation matters for sustained performance. The practical advice is simpler: when you catch yourself dismissing a problem because it seems boring or annoying, pause. That dismissal reflex is schlep blindness in action. The problem you just flinched away from might be the most valuable one in your field of view.

The Meta-Skill of Problem Selection

Problem selection is itself a skill, and like all skills, it improves with deliberate practice. Boyd's OODA loop is useful here. The orientation phase - where you synthesize incoming information with your existing mental models - determines which problems you even perceive as problems. If your orientation is narrow (limited experience, limited perspectives, strong schlep blindness), your problem-selection menu is impoverished regardless of how good your execution is.

Broadening orientation means exposing yourself to different industries, different disciplines, different types of work. The person who has done both intellectual and physical labor, both creative and administrative work, both glamorous and tedious projects, has a richer orientation than someone who has optimized for one type of experience. They see more of the problem landscape.

It also means developing the emotional tolerance for problems that do not feel exciting. This is trainable. Like any form of discomfort tolerance, it responds to graduated exposure. Start with a small schlep. Finish it. Notice that the world rewarded you for it. Let that evidence update your intuitions about which problems are worth your tempo.

The problem problem will not solve itself. But if you can see schleps clearly, evaluate puzzles honestly, and use packages without being captured by them, you are already operating with better problem-selection judgment than most of your competitors.

And in a world where execution talent is abundant, problem selection might be the scarcest skill of all.

Related

• Thrust, Drag, and the 10x Effect - why reducing friction matters more than raw effort, and how schleps are drag-removal in disguise
• Towards Thick Strategy Narratives - the contextual richness needed to evaluate problems beyond their surface appeal
• Thinking in a Foreign Language - using cognitive distance to see past the framing biases in problem selection
• Daemons and the Mindful Learning Curve - building the background processes that improve pattern recognition across problem types