Week 33, 2026
I am starting to question whether some products are monetizing additional value or charging customers to remove frustration from the experience they already had.
I think some companies may have discovered a new product to sell me: relief from the frustration built into the standard experience. That thought arrived while I was trying to select a tolerable airline seat. I had already chosen the flight. I had already accepted the schedule, the fare, and the conditions. All I wanted was a seat that did not make the journey feel like a test of endurance. But almost every option that looked remotely comfortable came with another charge. The upgrade did not feel dramatically better. The alternative simply felt harder to tolerate.
My first reaction was ordinary irritation. I felt nickel-and-dimed, slightly trapped, and worn down by a process that seemed designed to turn a basic decision into a series of small negotiations. I paid and moved on. But the moment stayed with me. Not because airline pricing is new. Not because different seats should cost the same. Greater space, better service, and additional comfort can all represent legitimate premium value and real differences in operating cost.
What stayed with me was the feeling behind my decision. I did not feel excited about getting more. I felt relieved that I could avoid getting less. And as a Product Manager, that distinction made me uncomfortable.
Once I noticed the feeling, I began seeing versions of it elsewhere.
When I searched for products on online marketplaces, I found myself scrolling past two or three screens offering me premium service before reaching what I had actually intended to find. I understand the commercial logic. Advertising can subsidize access. Recommendations can help me discover useful products. Upgrade to premium placements can motivate some customers. But, the experience felt less like discovery and more like navigation through commercial friction.
Then I saw a similar dynamic when ordering food. A delivery option looked convenient, but the most appealing time or reduced fee appeared to be reserved for members. Again, there could be perfectly reasonable explanations. Membership may create genuine savings. Capacity may be limited. Different service levels may reflect real costs. Still, I recognized the same internal reaction. I was not always asking, “What additional value will I receive?”, I was sometimes asking, “How much do I need to pay to make this simple again?”
Ride sharing gave me another version of the pattern. A task that once felt straightforward could now present me with several combinations of priority, comfort, speed, and service level. Some of those options can be useful. Some may help allocate limited capacity. Some customers genuinely value the choice. But upon ordering lowest tier I was not able to find a ride and I could not stop wondering whether every new tier represented a better outcome, or whether some tiers mainly made the standard option feel less attractive.
Individually, none of these experiences proves a deliberate strategy. I cannot see inside the pricing discussion, the operational constraints, or the product roadmap behind each decision. I do not know whether the friction is intentional, incidental, commercially necessary, or simply the accumulated result of many local optimizations. I can only distinguish among three things. I can observe the customer experience. I can infer a possible strategic pattern. I cannot present that inference as confirmed business practice.
Still, when I place the experiences next to one another, the pattern is difficult for me to ignore. First, I adopt a useful and attractive service. Then the service becomes part of my routine. Over time, I build habits, store preferences, accumulate history, learn the interface, receive loyalty benefits, or simply stop considering alternatives. Switching becomes harder, even when it remains technically possible. Then friction appears in the standard experience. Finally, a paid tier offers to remove some of that friction. What began as convenience becomes dependency. What felt standard becomes premium. What once looked like a product problem starts functioning like a revenue feature. I used to think premium meant getting more. Increasingly, it can feel like paying to suffer less.
I do not believe premium tiers are inherently bad. I have spent enough time in product management to understand the pressures behind them. I have worked with the realities of revenue targets, margins, conversion, adoption, retention, differentiation, and sustainable growth. I know that products have to fund themselves. I know that serving every customer in exactly the same way is neither realistic nor always desirable. I have probably contributed to smaller versions of this thinking myself.
I have looked at a funnel and asked what could move more customers toward a paid option. I have considered how packaging, limits, placement, and defaults might influence behavior. I have celebrated when a change produced a measurable commercial result. That is part of the job.
The discomfort begins for me when I examine what created the result. A conversion tells me what I did as a customer. It does not always tell me whether I felt delighted, persuaded, pressured, or defeated. If I pay for an upgrade, the dashboard may record demand for the premium experience. But I may not value the premium experience at all. I may simply be trying to escape the standard one. That means a conversion does not always prove value. Sometimes it proves exhaustion. This distinction matters because product teams are very good at measuring behavior. I can measure which option I selected, how quickly I selected it, whether I subscribed, whether I upgraded, and whether my revenue increased.
I am much less likely to see the resentment behind that action. A dashboard can show successful tier migration without showing that my relationship with the product has changed. I may once have thought, “This company helps me.” After enough friction, I may begin thinking, “This company has learned how much inconvenience I will tolerate before paying more.” The revenue might look the same. The relationship is not.
For me, the line is not between free and paid. It is not between advertising and subscriptions. It is not between standard and premium. The line is between creating premium value and withholding baseline value. A premium airline seat can provide more space, greater comfort, better service, or a meaningfully different experience. That is additional value. A marketplace subscription can offer genuine convenience, stronger services, or benefits that cost more to provide. That is additional value. A food-delivery membership can reduce fees by creating a different economic relationship. A priority ride can help allocate scarce capacity to someone willing to pay for speed. I can understand all of those models.
My concern starts when the standard experience is deliberately or repeatedly weakened so that the paid experience feels necessary. There is a difference between designing a premium experience and degrading the standard one. The traditional model is to make the premium option better. However, the emerging model appears to be to make the standard option worse, then sell me a path back to convenience. That may be commercially effective. It may increase subscription adoption, advertising revenue, average revenue per customer, upgrade conversion, or short-term margins.
But I believe it can also create damage that arrives more slowly. Trust erodes gradually. Goodwill declines quietly. Brand affinity becomes indifference. Loyalty becomes inertia. Advocacy becomes reluctant compliance. If I continue using the product because switching is difficult, my retention may look healthy even while my relationship with the company is deteriorating. Dependency may increase pricing power, but I believe it also increases product responsibility.
When customers have invested time, history, preferences, habits, or social connections into a service, I do not think that dependence should be treated simply as an opportunity for extraction. I think it should be treated as a responsibility to keep the baseline experience useful, respectful, and complete.
This realization changed the questions I want to ask when designing tiers, subscriptions, advertising experiences, priority services, and upgrade paths.
I now use five questions to test whether I am creating real value or monetizing avoidable pain:
- What new value am I creating in the paid tier?
- What part of the standard experience became worse before or after I introduced the paid tier?
- Would my customers still upgrade if the baseline experience remained genuinely good?
- Am I asking customers to pay for a benefit, or to remove avoidable pain?
- Am I strengthening customer trust, or merely exploiting switching costs?
I find the third question particularly revealing.
If a premium product only succeeds when the standard option becomes frustrating, I may not have built a compelling premium product. I may have weakened the comparison. That can still produce conversion. It does not necessarily produce customer value. I also think I need to measure more than the upgrade rate. I want to understand sentiment alongside conversion. I want to examine retention, cancellation reasons, support complaints, and changes in trust. I want to separate willingness to pay from willingness to tolerate. I want to know whether baseline deterioration is intentional, incidental, or operationally necessary. I want customer advocates involved in monetization decisions, especially when the commercially attractive option introduces inconvenience for people who do not pay.
I also want to apply a simple transparency test:
- Could I explain the design choice directly to a customer without hiding behind internal language?
- Could I say, clearly and honestly, what changed, who benefits, and why the new experience is fair?
If I struggle to explain the decision without using terms such as “conversion optimization,” “tier migration,” or “monetization efficiency,” I may need to look more closely at the customer value behind it. My goal is not to protect every feature from monetization. My goal is to build premium tiers around additional outcomes rather than manufactured discomfort. I want the paid experience to create something meaningfully better, not merely remove an unnecessary obstacle. I want to protect a baseline that remains worthy of the customer’s time.
Most importantly, I want to optimize for durable value rather than immediate upgrade rates.
What I want to remember
Ultimately, I am not arguing that every frustrating experience is intentional. Poor design happens. Operational constraints are real. Costs rise. Capacity is limited. Products become more complex. Business models evolve. A change that feels hostile to me may have a legitimate explanation that I cannot see. But uncertainty about intent does not remove my responsibility to examine the outcome.
If we repeatedly create experiences in which customers feel trapped, pressured, or worn down, we should not comfort ourselves simply because the conversion rate improved. Not every profitable product decision creates customer value. The question is not only whether my customers upgraded. The question is why.
I want to build products that customers want to upgrade, not products they need to escape. I want premium to mean more capability, more comfort, better service, less effort through genuine innovation, or a differentiated outcome worth paying for. I do not want premium to mean restoring the dignity, convenience, or quality that customers reasonably believed they had already adopted.
What concerns me is a narrower question. Have companies stopped creating new value, and have focused solely on monetizing the removal of frustration instead? That strategy may work for a quarter. It may even work for several years when habits are strong and alternatives are limited. But I do not believe reluctant compliance is the same as loyalty. If I pay because a company wore me down, I may convert today while quietly becoming available to its next competitor tomorrow. That is what I want to remember when I look at my next monetization dashboard. The metric may show me what the customer did.
My responsibility as a Product Manager is to keep asking how I made the customer feel, what value I truly created, and whether I would be proud to defend that choice three years from now.
This newsletter reflects my personal views and experiences as a product manager. It does not represent the views, strategies, or opinions of my employer or any organization I am affiliated with.
