Why Every Leader Needs A Side Hustle Mindset
The line between entrepreneurship and traditional leadership is becoming increasingly blurred. A 2024 study by researchers at James Cook University found that both managers and entrepreneurs require similar core abilities—dynamic capabilities, which include self-efficacy, alliance management and marketing capabilities—to excel in post-COVID, VUCA work environments (volatile, uncertain, complex, ambiguous). Increasingly, professionals across sectors are embodying this shift. The percentage of people working both salaried and entrepreneurial jobs (i.e., side hustles) has grown from 13% in 2020 to 38% in 2025, down slightly from 44% in 2022, according to annual LendingTree surveys.
While many professionals pursue side hustles for the extra income, the benefits run far deeper. Side hustles require and foster a particular mindset—and build a skill set—that can add massive value to salaried roles and shore up long-term career security. That is because these high-value dynamic capabilities (a side hustle mindset) are exactly what companies need to stay competitive and relevant in times of rapid change, tech innovation and upheaval.
Why The Side Hustle Mindset Matters More Than Ever
With all the economic uncertainty and instability In this job market, the invitation to all professionals is to be more adaptive, scrappy and inventive. But leaders in particular must deepen their entrepreneurial agility. Delivering excellent results is necessary, but no longer sufficient.
As AI and lean teams shrink org charts, leaders must create their own value-add rooted in their distinctly human gifts and talents. For rising and established leaders alike, career longevity requires building more and more options for one's career trajectory—as opposed to clinging on to the dream of 'climbing the ladder' within the same organization.
We can meet this moment with the side hustle mindset, which encompasses skills like resourcefulness, self-direction, calculated risk-taking, market-driven thinking and digital fluency.
What The Side Hustle And Mindset Can Look Like At Different Career Stages
For early-career professionals, side hustles can serve as self-created, self-driven apprenticeships that solidify fundamental professional skills: communication, organization and time management, client or customer service, analytical thinking and problem-solving.
For those in extended job searches, side hustles can also provide structure, a sense of purpose, fulfillment and momentum. They also offer valuable work experience that can be parlayed into future salaried positions or scalable businesses.
In other words, a side hustle can be the fastest way to build portfolio experience and road-test your career interests—on your own terms.
For mid-career professionals and leaders, entrepreneurial throughlines in your professional branding can set you apart in a crowded and competitive job market. Review your body of work through an entrepreneurial lens and determine how to weave those elements into your career narrative and highlight them across your professional assets (LinkedIn profile, online bio, executive summary on your resume). It could be the differentiator that lands you the coveted leadership role you've been working towards.
If you have a side hustle, leverage it to grow your leadership, innovate solutions and develop your risk management skills—all while building your executive presence and honing your ability to pitch ideas with confidence.
A side hustle (or the mindset alone) will force you to expand your horizons and your network—all of which strengthens your 'career insurance' for when 'stable' jobs suddenly disappear.
For senior leaders, you likely already have a plethora of entrepreneurial leadership examples to draw from—conduct an audit on your own or with an expert to ensure you're positioning yourself strategically and advantageously.
At this stage of your career, side ventures, investment projects or advisory work can keep your entrepreneurial edge sharp. Research, vet and join appropriate peer cohorts or engage in micro-learning to stay relevant without overcommitting yourself given the demands already on your plate.
How To Cultivate A Side Hustle Mindset—Even If You're Not Launching A Business
No matter your career stage or specific circumstance, given how the landscape is trending, it is imperative to think like a founder in your role. Practice this by identifying root problems, creating actionable solutions and carefully studying the market. Invest in your entrepreneurial skill-building through small-scale experiments (entrepreneurial programs, pilot projects, advisory roles, partnerships) that let you fail fast and help you adapt even faster.
This self-directed learning can be one of the highest-ROI investments you make in your career.
Leadership isn't about waiting your turn—it never was. It's about making your own moves and strengthening your dynamic capabilities, entrepreneurial skillset and side hustle mindset.
Whether or not you ever launch a formal side hustle, you will need that mindset and those dynamic capabilities to succeed in the decades ahead.
And the good news is that a side hustle mindset is fully learnable and fully portable. Once you build it, no one, no organization, no downturn can take it away from you.
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