Finding Work After 40: Individual Initiative Is Not the Whole Story

I have been reflecting on Nicole Vanderbilt’s career pivot and the lessons we can draw from her experience.  Watch it here:

The infinite career – why we can’t retire | FT Working It

Her approach was entrepreneurial. After being made redundant at Etsy, she recognised an opportunity in an industry she had always wanted to work in. She connected that opportunity to her previous experience and approached the founder and CEO of Bookshop.org directly.

Rather than simply applying for a vacancy, she initiated a conversation about how she could help the business grow.

There is a valuable lesson here: sometimes, we need to look beyond advertised vacancies and recognise where our experience could create value.

But I think we need to be careful about how broadly we apply this lesson to the challenge of finding work after 40.

Nicole’s experience is one example of a successful career pivot. It is not a general strategy that will work for everyone navigating the labour market in midlife.

There are three different dimensions to consider.

1. Creating an opportunity

This involves recognising a business need, connecting it to your experience and capabilities, and being willing to initiate a conversation.

It means looking beyond job descriptions and considering where your knowledge, skills and relationships could create value.

2. Finding employment

This is a different challenge.

It involves navigating recruitment processes, competition, age-related bias, changing skills requirements and the availability of suitable roles.

The ability to recognise an opportunity does not necessarily mean that an employer will recognise your value or that a suitable position will be available.

The OECD’s Employment Outlook 2025 provides an important perspective.

In 2022, the proportion of employees newly hired was:

• 15% among workers aged 35–44.
• 11.8% among workers aged 45–54.
• 9.5% among workers aged 55–64.

The OECD also identifies age discrimination, employer perceptions of adaptability and unequal access to training as barriers facing older workers. It highlights that age discrimination can be particularly significant for older women.

These figures do not explain every individual’s experience, but they illustrate why finding employment later in one’s career deserves a wider discussion.

3. Building a sustainable longer career

Finding the next job is only one part of the equation.

How do we maintain income, professional relevance and financial security across a longer working life that may involve several career transitions?

This could mean moving into consulting, developing a portfolio career, starting a business, taking a sideways move or acquiring new skills for a different industry.

It also means thinking about financial resilience: building assets, managing financial commitments and developing income options that can support us through periods of transition.

What can we do as individuals?

There are practical lessons worth taking from Nicole’s approach:

1. Recognise opportunities beyond advertised vacancies.
2. Identify and communicate your transferable skills.
3. Understand the needs and ambitions of organisations.
4. Build relationships and initiate conversations.
5. Stay open to alternative career paths, including consulting, portfolio careers, entrepreneurship and sideways moves.

But individual initiative is only one side of the equation.

We also need employers, recruitment systems, education providers and policymakers to recognise the value of experienced workers, provide access to lifelong learning and address age-related barriers.

We should not place the entire responsibility for overcoming ageism and labour-market barriers on the individual.

This is particularly important as people live longer and working lives extend.

For me, this is where The Infinite Career becomes a much bigger conversation.

It is not simply about how we find our next job. It is about how we remain economically active, relevant and financially secure through different stages of our working lives.

And there is a question I think we should be asking more often:

If we are expected to work longer, are our labour markets, employers and financial systems evolving to support longer and more varied careers?

An infinite career requires both the ability to create opportunities and the financial capacity to navigate transitions.

That is a conversation worth having.

Source: OECD Employment Outlook 2025, “Navigating the Golden Years: Making the Labour Market Work for Older Workers.”