Hi, this is Ray.

I want to tell you about the most expensive persistence mistake of my adult life. I was in my early thirties, trying to learn a specific programming framework because everyone told me it was the future. I spent about three months on it, grinding through tutorials that never quite clicked, building small projects that always felt like fighting against the tool, reading documentation that read like it was written for someone who already knew everything I was trying to learn. Every week, I made incremental progress. Every week, the material felt slightly less foreign. I told myself I just needed to keep pushing. Everyone said the framework was worth learning. Everyone said the initial learning curve was steep. Everyone said if I just persisted, it would click.

Three months in, it hadn't clicked. What I told myself, correctly, was that persistence had gotten me most of my previous learning wins. What I told myself, incorrectly, was that the current struggle was the same kind of productive struggle I'd experienced before. What I couldn't see at the time was that I was grinding on a specific approach that wasn't working for me, when a completely different approach would have gotten me to the same destination in a fraction of the time. I finished the three months feeling exhausted and vaguely defeated, and moved on to other things. When I revisited the topic two years later, I tried a different approach (starting with the underlying concepts before touching the framework) and I got further in two weeks than I had in the entire previous three months.

The lesson from that experience took me longer to fully absorb than it should have. Persistence isn't unconditionally good. Sometimes the persistence itself is the problem. The learner who grinds against an approach that isn't working, when a different approach would work far better, is worse off than the learner who quits the approach and tries something new. And the cultural framing that treats all quitting as failure and all persistence as virtue actively pushes learners toward the wrong behavior in these situations.

I've written about persistence positively in this newsletter series… about plateaus, about pushing through when it feels hard, about the boring compounding of consistent work. All of that is true. What's also true, and what today's newsletter is about, is the flip side. Sometimes persistence is destructive, and knowing when to quit an approach is a genuine learning skill. The research on this is clearer than most learners realize. Let's get into it.

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Let me start with what the science shows, because the popular framing of persistence versus quitting misses the actual distinction that matters.

The relevant framework comes from research on what psychologist Carsten Wrosch calls adaptive goal regulation. According to summaries of this work, Carsten Wrosch's model outlines adaptive persistence as contextually appropriate continuation of viable goals, contrasted with flexible quitting… strategic disengagement from unattainable objectives to redirect resources toward new pursuits, preventing emotional depletion. This approach underscores that effective self-regulation involves discerning when to persist versus disengage, promoting resilience by avoiding prolonged investment in futile endeavors while sustaining motivation for alternative goals. Read that carefully. The research distinguishes not between "persisters" and "quitters" but between people who can accurately assess when persistence is productive and people who can't. The skill isn't persistence itself. It's judgment about when persistence serves you.

This maps to a distinction the research has been developing for years. According to work in the Journal of Applied Social Psychology, strategic goal striving (disengagement from the unattainable goal followed by reengagement with an alternative goal) was facilitated by autonomous goal motives, and culminated in increases in positive affect. Individuals who judge the likelihood of goal attainment to be high should engage in effort coping and persist with striving. Alternatively, those who judge attainment to be unlikely should disengage and seek another way to achieve their goal. The framing that matters. When you judge that continued effort on the current path will get you where you want to go, persist. When you judge that it won't, disengage from this path and find another way. Both are legitimate self-regulatory moves. Which one is correct depends on the situation, not on the general virtue of either behavior.

A recent concept analysis published in Frontiers in Education made the case even more directly for learners. According to the researchers, the outcome-oriented nature of task persistence suggests that sustained effort does not necessarily lead to productive progress. Future research could therefore examine how learners develop the reflective judgment required to balance sustained effort with strategic disengagement, particularly in educational settings where adaptability is essential for learning. Read this carefully. Sustained effort does not necessarily lead to productive progress. This isn't a controversial claim. It's what the research shows. The learner who persists on the wrong approach continues to sustain effort without producing progress. This is a specific failure mode that pure "persist through everything" advice can't address.

Let me name the specific problem that pure persistence advice creates for learners.

Every serious learning project involves multiple approaches. There are usually five or ten reasonable ways to learn any given thing. Some of these approaches will work well for your specific brain, your specific background, your specific goals. Others won't. The learner who grinds against an approach that doesn't fit them (because the approach is popular, or because someone recommended it, or because they've already invested time in it) produces worse results than the learner who tries the approach, notices it's not working, and switches to something else.

The specific failure mode is what behavioral economists call escalation of commitment. According to research on the phenomenon, decision makers have a tendency to become locked into courses of action… to throw good money after bad. Successful goal striving unfolds between tenacious persistence on the one hand and timely disengagement on the other when a goal has become futile and too costly. This isn't a claim about weakness or laziness. It's a claim about a specific cognitive bias that leads people to continue investing resources in efforts that aren't working, specifically because they've already invested resources in those efforts. The sunk cost drives the continued investment, not the actual likelihood of success.

For learners, this pattern is genuinely destructive. I know people who've spent years learning things through approaches that don't work for them, gradually accumulating frustration and doubt about their own ability, when a different approach would have worked in months. The persistence itself was the problem. The learners weren't lacking grit. They were lacking the flexibility to recognize that grit was being applied in the wrong direction.

Here's where the practical work happens. When you're struggling with something, how do you tell whether you're in productive persistence (keep going) or destructive stubbornness (switch approaches)? The research and my own experience point to several diagnostic markers.

Are you making any measurable progress? Productive persistence produces slow but real progress, even during the hard parts. You can point to specific things you couldn't do a month ago that you can do now. Destructive stubbornness produces no measurable progress… you're putting in effort but nothing is actually improving. The distinction is genuinely diagnostic. If you've been at something for two or three months with zero movement, the approach probably isn't the right one for you.

Does the difficulty feel like productive struggle or like flailing? As I covered in the productive discomfort newsletter, productive struggle has a specific quality… it's hard, but the hardness feels like it's producing something. You can identify what specifically you're working on. You can see the edges of your current understanding. Destructive stubbornness feels different… diffuse, overwhelming, without clear edges. Every session feels the same as the last. You can't articulate what specifically is hard. The lack of specificity is a signal that you don't have enough traction for the approach to work.

Have you tried multiple different approaches? If you've only tried one approach, you don't have enough information to know whether the difficulty is in the material or in your approach to the material. The learner who's spent six months on one approach without trying anything else is making an assumption (that this approach is the right one) that they haven't actually tested. Try a different approach for two weeks. If the new approach produces clearly different results, you've learned something important about which approach fits you.

What does successful learning look like for you in other domains? Pay attention to how you learned things that clicked easily. What approach did you use? What conditions did you have? Sometimes the current struggle is a signal that you're operating outside the conditions that produce learning for you. Not everything can be forced to happen in all conditions. Sometimes recognizing that this specific approach doesn't fit your learning style is the correct move.

Are you continuing because the approach seems to be working or because you've already invested? This is the sunk cost question. Honestly ask: if I were starting fresh today with all the information I now have, would I choose this approach? If the answer is no, you're continuing because of sunk cost, not because of productive assessment. This is the moment to disengage.

What would someone else in your situation do? This is a useful thought experiment. If a friend came to you and described the exact same situation (three months on an approach, no clear progress, mounting frustration) what would you advise them? People are often more clear-eyed about others' situations than their own. The advice you'd give a friend is often the advice you should take yourself.

I want to be careful about this because I don't want to accidentally advocate for constant approach-switching, which is its own destructive pattern. Sometimes persistence is genuinely the right move. Let me name when.

When you're in the productive struggle zone. The 20-40% failure rate zone I covered in the productive discomfort newsletter. If you're failing that often but making measurable progress, you're in the right zone. Keep going.

When the difficulty is expected. If the material or skill is genuinely known to be hard for everyone, and you're not further behind than typical learners at your stage, the difficulty isn't diagnostic. Everyone struggles here. Persistence is the correct response.

When you've just started. The first two or three weeks of any new approach usually feel hard because you don't yet have the foundation to make sense of what you're learning. Quitting after three weeks of any approach is usually premature. Give approaches enough time to actually reveal whether they'll work.

When emotional resistance is the main obstacle. Sometimes what feels like "the approach isn't working" is actually "I don't want to do the work this approach requires." These are different problems requiring different responses. If the approach would work but you're avoiding the work, more persistence and less avoidance is the correct move.

When switching would just repeat the pattern. Some learners approach-switch constantly, always finding reasons why the current approach isn't working, spending most of their time in the awkward beginning phase of new approaches. This is its own destructive pattern. If you're switching often, the question isn't whether the current approach is right… it's whether your pattern of switching is preventing you from getting deep enough into anything to actually learn.

Okay, if you've decided the current approach isn't working and you should switch, how do you do it well? This isn't just about giving up… it's about redirecting your effort more effectively.

Extract the learning from what didn't work. Before switching, take specific stock of what you learned from the failed approach. Even wrong approaches teach you things. What did you understand better now than when you started? What specifically about this approach didn't fit? What do you now know about how you learn that you didn't know before? The failed approach isn't wasted if you extract these lessons.

Choose the new approach deliberately. Don't just switch randomly. Think about what specifically didn't work about the previous approach and what a genuinely different approach would offer. If the previous approach was heavy on abstract theory, try a hands-on approach. If it was solo self-study, try finding a teacher. If it was fast-paced, try something slower. The switch should address what specifically wasn't working, not just be a change for its own sake.

Commit to the new approach for a defined period. Give the new approach enough time to actually reveal whether it works. Two or three weeks is usually the minimum. Don't switch again after five days if the new approach isn't immediately magical. Give it real time to prove itself.

Notice patterns across your switches. If you've switched approaches multiple times, look for patterns. Do you always switch when things get hard? Do you always switch when the initial excitement fades? Are there specific triggers for your switches that don't relate to the actual quality of the approaches? The meta-pattern is often more informative than any individual switch.

Distinguish approach-switching from goal-switching. Sometimes the issue isn't that this approach doesn't work… it's that you don't actually care about the destination. If you've switched three approaches to learn the same thing and none are sticking, consider whether the underlying goal is genuinely yours or whether you're pursuing something you think you should want.

Here's what I want you to take from all this. The cultural narrative around persistence has value… consistency beats intensity, plateaus are normal, showing up matters. All of that is true. But it becomes destructive when it's applied without judgment about whether the current effort is actually producing learning. Grinding harder on an approach that doesn't fit you isn't grit. It's stubbornness. And stubbornness is genuinely worse for your learning than switching to something that fits.

If you've been persisting on something without making real progress, please consider that the issue might not be your persistence. It might be your approach. The same effort, applied differently, might produce dramatically different results. This isn't a failure of character. It's a signal that this specific method doesn't work for your specific brain. The learners who become genuinely excellent at things don't just grind… they find the approach that fits them, and then they grind on that approach.

In Chrono Trigger, if the party keeps losing to a boss with their current strategy, the correct move isn't to keep throwing themselves at the boss with the same setup. The correct move is to change their equipment, adjust their team composition, or level up somewhere else and come back with different capabilities. Same for your learning. The boss you can't beat with your current strategy might be trivial once you change approaches. Recognizing this (recognizing when to switch tactics rather than grinding on failing ones) is a genuine skill. Build it. Your learning will get faster.

Persistence when it's productive. Disengagement when it isn't. Both moves are legitimate. Both moves are self-regulatory skills. The learners who develop the judgment to know which is which produce more learning than the learners who commit to either strategy universally. Be strategic about your persistence. It's not a failure of grit. It's the higher-order skill that makes grit actually pay off.

Keep learning (and keep evaluating your approach),

Ray