The Winner’s Curse of Wellbeing: Why Ambitious Plans Fail and the One Question That Makes Them Sustainable
By Louise Dennison O’Shaughnessy
Many personal wellbeing resolutions begin to unravel within the first few weeks. Not because you lack discipline, but because you overcorrect.
There is a concept in economics called the “winner’s curse”. In an auction, the winner is rarely the most accurate bidder, just the most optimistic. They want something so badly that they overpay. Then reality sets in.
Wellbeing can work in much the same way.
You get inspired by a podcast, a book or a colleague who swears by their 5am routine. Suddenly, you are building the perfect plan: cold plunges, perfect nutrition, daily meditation, 10,000 steps, no carbs and no joy.
You win the plan. Then real life shows up.
A late meeting. A sick child. Three days of travel. The plan collapses, and you blame your willpower.
But willpower was never the problem. The plan was built for your best week, not your real one. Perfect conditions are not a wellbeing strategy. They are a motivational poster.
In my work with founders and senior leaders, I see this pattern repeatedly. They do not lack commitment. They are overcommitted to a version of themselves designed for conditions that rarely exist.
So, I ask one question:
During your most average week, could you do 70% of this without heroic effort?
If not, it is not yet a practice. It is an aspiration.
Flourishing is not built through aspiration alone. It is built through repetition.
Start with three anchors that can survive real life:
- Protect one recovery habit.
- Progress one meaningful priority.
- Prioritise one genuine human connection.
The Organisational Winner’s Curse
Organisations experience their own version of the winner’s curse. They introduce ambitious wellbeing calendars, awareness campaigns, apps, webinars and one-off initiatives without first examining workload, management behaviour or whether employees have the time and psychological permission to participate.
A wellbeing initiative cannot compensate for consistently excessive workloads, unclear expectations or a culture in which recovery is treated as a lack of commitment. If the working environment contradicts the wellbeing message, employees will notice the contradiction immediately.
Leaders should ask the same question of their workplace wellbeing strategy:
Could our people realistically engage with 70% of this during an ordinary, high-pressure week?
If participation depends on unusually quiet workloads, exceptional motivation or employees giving up their personal time, the initiative has not been designed for the real organisation.
The aim is not to reduce ambition. It is to create an approach that employees can access, managers can support and the organisation can sustain.
A Practical Leadership Checklist
Before introducing another wellbeing initiative, leaders should take an honest look at the environment in which employees are being asked to participate.
- What wellbeing practice could our people realisticallymaintainduring a demanding week?
Design wellbeing around the working week employees actually experience, not an ideal version of it. A practice that only works when workloads are light is unlikely to become embedded.
Focus on simple, accessible actions that can continue during busy periods without requiring employees to sacrifice their personal time.
- Are managers given the skills and confidence to support employee wellbeing?
Managers play a central role in shaping employees’ everyday experience of work. They need more than a list of wellbeing resources.
Appropriate Mental Health First Aid training can help managers develop the confidence to recognise when someone may be struggling, begin an appropriate conversation and direct employees towards suitable support.
- Do our workloads and deadlines reinforce or undermine our wellbeing message?
A wellbeing programme cannot compensate for consistently excessive workloads, unrealistic deadlines or a culture of constant availability.
Leaders should examine whether working practices support recovery or whether employees are being encouraged to look after themselves while operating in conditions that make this almost impossible.
Where excessive workload, stress or burnout may present an organisational risk, a psychosocial risk assessment can help identify the underlying causes and inform practical action.
- Are leaders modelling the practices they ask employees to adopt?
Employees pay attention to what leaders do, not only what they say.
If senior leaders regularly work through breaks, send emails late at night, remain available while on leave or praise excessive hours, those behaviours become the real cultural message.
Leaders must demonstrate that rest, boundaries and recovery are compatible with strong performance.
- Do employees have the time and psychological permission toparticipate?
Making a wellbeing initiative available does not automatically make it accessible.
Employees must believe they can take part without being judged, falling behind or appearing less committed. This is where line managers play a decisive role.
Too often, people are expected to complete a full day’s work and attend a course on top of it, signalling that wellbeing is an optional extra rather than a genuine priority. Managers need to protect that time, allowing people to participate without leaving the day’s workload waiting for them afterwards.
Participation should be supported during working hours wherever possible and reinforced through managers’ words and actions.
- Are we measuring participation or meaningful impact?
Attendance figures, app registrations and webinar views can show activity, but they do not necessarily demonstrate improvement.
Organisations should also consider whether employees feel better supported, whether managers are more confident, whether unhealthy working patterns are changing and whether the overall experience of work is improving.
- Have employees helped shape the approach?
Wellbeing strategies are more likely to succeed when they reflect the genuine needs of the workforce.
Employee consultation can help organisations understand where pressure is coming from, what support people would value and what may prevent them from engaging. It also helps avoid investing in initiatives that look impressive but solve the wrong problem.
- Is the initiative inclusive and genuinely accessible?
Not every wellbeing activity will suit every employee.
Leaders should consider different working arrangements, locations, schedules, abilities, cultures and personal circumstances. A credible strategy should offer different ways to engage rather than promoting one narrow idea of what wellbeing should look like.
When planning wellbeing initiatives, leaders should ensure they work for introverts and extroverts alike, as well as those working remotely. Participation should never depend on being comfortable in a crowd or physically present in the office.
- What could we stop doing to create space for what matters?
Sometimes the most effective wellbeing intervention is not an additional programme.
It may involve removing an unnecessary meeting, simplifying a process, clarifying responsibilities or reconsidering an unrealistic deadline. Before adding another initiative, identify what can be reduced, redesigned or stopped, and review what the organisation already has in place.
- Can this approach survive beyond its launch?
Wellbeing should not depend on a single awareness day, enthusiastic sponsor or short-term campaign.
Consider who will take responsibility for the initiative, how managers will support it, how progress will be reviewed and how it will remain visible once the initial momentum has passed.
A strong workplace wellbeing strategy is not the one with the busiest calendar or the greatest number of initiatives. It is one that employees can access and genuinely benefit from, leaders consistently support and the organisation can sustain when work becomes demanding.
This is at the heart of our approach at EHS International. We help organisations move beyond wellbeing theatre and create cultures in which healthy practices are realistic, repeatable and genuinely embedded.
The goal is to support leaders and teams in building resilience that holds under pressure, not just on paper.
Flourishing is not built through heroic effort. It is built through practices that survive the messy, ordinary, real week.
Let’s build a culture that lasts.
How EHS International Can Help
EHS International works with organisations to develop practical workplace wellbeing strategies that reflect the genuine needs of their people and business.
Our Workplace Wellbeing Partnerships provide structured, ongoing support for organisations seeking to move beyond isolated initiatives. Support can include strategic planning, leadership guidance, management support, employee engagement, tailored wellbeing programmes and access to specialist expertise.
To learn more about how EHS International can support your organisation, contact our Mental Health and Wellness team.
Thank you for reading about: The Winner’s Curse of Wellbeing: Why Ambitious Plans Fail and the One Question That Makes Them Sustainable.
About the Author: Louise Dennison O’Shaughnessy
Louise Dennison O’Shaughnessy is Director of Mental Health and Wellness at EHS International. She works with leaders and organisations to develop practical, sustainable approaches to workplace wellbeing that move beyond one-off initiatives and become embedded in everyday organisational culture.
Her work focuses on helping organisations strengthen resilience, support employee wellbeing and create healthier working environments that can withstand the realities of pressure, change and competing demands.
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