College-educated mothers invest more time in children’s learning than non-college-educated mothers, yet they report substantially lower enjoyment of those same activities. Using purpose-built survey data from 1,552 mothers of kindergarteners in Chicago Public Schools — the first dataset to measure parental time investment, enjoyment, stated motivations, and well-being in a single sample — we document this enjoyment paradox and trace its internal structure. The raw enjoyment gap is 28 percentage points on a peak-enjoyment measure (10/10) and 0.87 points (0.62 standard deviations) on a continuous scale; it survives rich controls for demographics and psychological barriers. The gap is concentrated among non-employed, above-median-income college-educated mothers, who report the lowest enjoyment and invest less than their employed college-educated counterparts at the same income level, even though non-employment is associated with more investment among less-educated mothers. Below the income median, the pattern reverses. We interpret these findings through a framework suggesting that the hedonic cost of intensive investment falls most heavily on the group facing maximum norm salience without a competing professional identity.