The traditional corporate ladder is evolving. C-suite tenures are shrinking — down to just under five years at S&P 500 companies – economic volatility is the norm and today’s top executives no longer see themselves as 'lifers' at any single organisation. In this new reality, a growing number of leaders are quietly building parallel ventures between board meetings and earnings calls: appearing on podcasts, advising startups, and testing new concepts.
Read more: Are side hustles a threat to employment?
The trend has reached a tipping point. A Times article highlighted the rise of "fractional twins": C-suite executives pairing full-time roles with shared fractional leadership at startups. For startups, it’s a way to access premium expertise without full-time costs. For executives, it’s an entrepreneurial runway. And for HR? It’s both a retention opportunity and a compliance tightrope walk.
The side hustle surge
Seismic shifts have normalised the C-suite double life:
- The end of a ‘job for life’: Eroded job security means that side ventures have become rational career insurance.
- Broadening demand for non-execs: The historical 'white skin, white hair and accounting qualification' of the average board member is changing. Companies are inviting ever-younger executives to join their board, particularly to buy in more current technology credentials.
- The gig-ification of expertise: Yes, this is happening in the C-suite too. Accessible entrepreneurial tools and platforms like LinkedIn and Substack let executives monetise their knowledge independently in minutes.
- Generational shifts: Millennial leaders are increasingly choosing portfolio careers to hedge against disruption and build their personal brand.
Complement or compete?
Not all side gigs are created equal. Before greenlighting an executive’s side venture, HR leaders should ask:
- Does this complement or compete with their primary role? A CFO advising startups may sharpen strategic skills; a CTO building a competing software as a service (SaaS) tool is a nonstarter. HR should enforce guardrails.
- Can they sustain this without burnout? Juggling dual ventures requires ruthless prioritisation. HR can help assess workload impact.
- Would this pass the disclosure test? Transparency with HR and the board is a litmus test for trust, compliance and risk mitigation.
- Is this about income, passion, or a pivot? The answer determines whether it’s a hobby or an escape hatch – an executive building a sustainable board-shorts brand in Shopify is a different proposition to someone who is plotting a prospective unicorn in stealth mode. HR should align expectations and policies accordingly.
HR’s dilemma: innovation or insurrection?
HR teams face a delicate balancing act. Crack down too hard, and you risk alienating high performers who crave autonomy. Look the other way, and you may inadvertently enable conflicts of interest or divided focus. The solution isn’t rigid policies, but smart guardrails that acknowledge reality while protecting the organisation.
Read more: Employee side hustles: what are the risks for employers?
Forward-thinking companies are replacing paranoid prohibitions with dynamic frameworks, for example:
- The fractional matrix: Green-light unrelated passion projects, require disclosure for adjacent gigs in overlapping industries, and prohibit direct competitor ties.
- Retention bargaining and intrapreneurship: Offer equity stakes or internal ‘side-gig’ projects (e.g., leading an innovation lab as part of research and development) to keep entrepreneurial talent engaged.
- Transparency as culture: Normalise discussions about external work in interviews and reviews – what’s learned externally often benefits the primary employer.
- Keep it captive: Companies can simultaneously help leaders 'scratch the side gig itch' and solve governance problems by allowing senior performers to sit on boards of companies they are investing in via in-house incubator funds.
The key is distinguishing between exploration and exit planning. A CTO writing a tech newsletter may sharpen their industry insights, while a CFO quietly building a fintech startup could signal restlessness. HR must develop the discernment to spot the difference and the flexibility to adapt.
The future of executive loyalty
Side hustles aren’t going away. In an era of economic uncertainty and shorter job cycles, they’ve become a vital career strategy. The question isn’t whether companies should allow them, but how to integrate them in a way that benefits both the organisation and its leaders.
Read more: Employers should support side hustlers
Today’s retention strategy isn’t about demanding undivided loyalty, it’s about proving the company remains the best place for top talent to grow, even as they explore outside ventures. The alternative is watching your next great leader walk away, not because they wanted to leave, but because you gave them no reason to stay.
By Will Lahaise, co-founder of executive search firm pltfrm
