Resume Now’s 2024 career regrets survey found that over one-third (~33%) of workers wish they had taken more career risks — a category that includes but is not limited to entrepreneurship. By contrast, only 8% of business owners regret starting their ventures, according to both a HubSpot survey of 200+ entrepreneurs and a Harris Poll of 504 small business owners conducted a decade apart. That figure is remarkably low given that roughly half of all small businesses fail within five years — survivorship bias likely explains part of the gap, since founders who failed and returned to employment are absent from these samples. A 2023 study in Frontiers in Psychology confirmed that anticipated inaction regret is a statistically significant driver of entrepreneurial intentions.
The psychological mechanism is Gilovich’s classic temporal asymmetry. Action regrets — a failed business, lost savings, years of stress — are acute but fade as people rationalize, learn, and integrate the experience into their identity. Inaction regrets — never finding out whether the idea would have worked — compound over time because there is no experience to rationalize and no story to tell. The Ownr/Avail 2022 survey of Canadian business owners found that 85.4% regret not starting their business earlier — a finding that captures the temporal dynamic from the opposite direction: even among those who eventually acted, the dominant regret is having waited too long.
The main caveat is that no published survey has directly asked a representative sample of non-entrepreneurs whether they regret not starting a business. The 33% “wish I had taken more risks” figure is a broader career-risk proxy that overstates entrepreneurship-specific inaction regret for some respondents and understates it for others. Gallup’s finding that 62% of US adults prefer self-employment provides aspiration context but should not be conflated with regret — preferring something is not the same as regretting its absence. What the data does establish is the directional asymmetry: among those who start, regret is rare; among those who wish they had taken risks, the sentiment is common and grows with age.