How to build a satisfying, sustainable career as a mid-life generalist

Jonathan is a business leader with 25-30 years of experience in B2B organisations, a career generalist who has navigated multiple industries and global markets, and an active member of Generalist World. Previously, he spent a decade at a security firm working with ex-military professionals on kidnap and ransom advisory services. His work has ranged from building international sales teams in Central America to implementing inventory management software in post-Gaddafi Libya to leading turnaround projects on the Isle of Wight. Jonathan was also a team builder at a startup in Cape Town, establishing operations from scratch after creating the company's first website despite having no prior technical experience.

What you'll learn:

Some takeaways:

Network relationships operate on delayed reciprocity and trust-building. Jonathan's career opportunities consistently came from relationships built years earlier, a school gate conversation led to a Libya project, language skills from university enabled Central American roles, and ex-military connections opened security industry doors. The key principle is "you get what you give," meaning networks only function when members contribute without expecting immediate returns. This creates a trust economy where your reputation and willingness to help others eventually generate opportunities you couldn't have predicted or directly pursued through traditional job applications.,

Recruiters use LinkedIn as a competitor-mining tool, which disadvantages generalists but creates specific opportunities. Executive search firms typically search competitors' employee lists for equivalent roles, making specialist profiles easy to match. Generalists with varied company histories actually appear in more searches across different sectors, though less frequently overall. The strategy is positioning yourself as a "wild card candidate". Someone who brings a cross-industry perspective to sense-check what employers think they need. This requires confidence to say "I don't have five years in this specific industry, but my three years plus adjacent experience offers valuable challenge to your assumptions."

The 50+ workforce faces structural disadvantages from demographic homogeneity in hiring rather than intentional ageism. Talent managers naturally gravitate toward hiring people similar to themselves, and younger demographics dominate HR functions. However, this generation possesses unique adaptability credentials; they've navigated the transition from no computers to supercomputers, no email to AI, and no remote controls to smartphones. Government recognition of longer working lives and pension sustainability is creating policy support for extended careers, while many professionals want to work into their late 60s and 70s because they genuinely enjoy the work and possess deep expertise.

Career progression for generalists follows a counterintuitive pattern where early-career sacrifice leads to senior-level advantage. In your 30s, generalists typically earn less and progress more slowly than specialist peers, creating difficult periods of comparison and self-doubt. However, senior leadership roles inherently require generalist skills—translating between finance, engineering, and marketing specialists; connecting cross-functional teams; and synthesising diverse expertise. The varied experiences accumulated during those difficult years become competitive advantages in executive positions where breadth matters more than depth in any single domain.

Business failure is contextual and environmental rather than purely execution-based, making timing and market positioning crucial. While a perfect strategy matters, environmental factors and macro trends often determine success more than internal execution quality. A rising tide lifts all boats, making it easier to succeed in growing markets regardless of organisational perfection. Conversely, when the tide goes out, you discover which organisations were built well. This means generalists should evaluate market timing and sector trajectories as carefully as their own capabilities when choosing opportunities.

Professional micro-networks are replacing broad platforms as the primary value creation mechanism in career development. LinkedIn functions increasingly as a broadcast platform rather than a genuine network, while curated communities like Generalist World and Brave Starts (focused on 50+ professionals) provide trust-based, actionable support. These niche networks offer a manageable scale where members understand shared purpose, contribute openly in semi-public forums, and build genuine reputational capital without algorithm gaming. People will belong to multiple micro-networks simultaneously based on different aspects of their professional identity, and this portfolio approach represents the future of professional community.

Leading specialist teams requires deliberate humility and role clarity around being the translator rather than the smartest person. The best teams combine generalists and specialists; pure specialist teams struggle with cross-silo communication and politics, while pure generalist teams lack execution depth. Generalist leaders should openly celebrate not being the cleverest person in the room and position themselves as enablers who make specialists better through connection and translation. This creates win-win dynamics where specialists feel valued for their expertise while generalists add value through synthesis rather than competing on technical depth.

Career resilience requires accepting that lows make highs better while maintaining benchmarks for when to pivot. Difficult periods are inevitable in any career, and sometimes the best strategy is simply continuing forward with defined checkpoints, "I'll reassess at Christmas", or "give it six months." However, this persistence must balance with honest self-assessment and willingness to call time on situations that aren't working. Failing and learning are acceptable and valuable; the failure only becomes problematic when no learning occurs. This means starting network outreach early when situations feel challenging rather than waiting for crisis points.

The entrepreneurship explosion driven by AI and shifting employment norms creates new pathways for midlife generalists. Traditional career security (one job, one employer, pension after decades) is dissolving, making self-employment and small business creation increasingly necessary rather than aspirational. AI is reducing barriers to entry for starting businesses, making solo operations or two-to-three-person teams viable at scale. Government procurement is shifting toward smaller organisations that can move quickly and respond to customer needs better than large incumbents. This trend particularly benefits generalists in their 50s who possess deep experience, established networks, and adaptability credentials forged through decades of technological change.

Where to find Jonathan

Where to find Milly

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