Research shows that the leap from employment to running your own business is far from a simple “quit and succeed” path and that those most likely to succeed take a gradual, carefully planned approach.
“This is especially true for high-net-worth individuals (HNWIs) and ultra-high-net-worth individuals (UHNWIs) who transition from a structured, secure corporate career into entrepreneurship or personal ventures. The transition is not just professional but also a multidimensional financial, emotional and strategic shift that requires careful planning, insight and risk management,” says Zanele Zungu, Advisor at Citadel.
WHY CORPORATE LEADERS CHOOSE A NEW START
One comprehensive study found that the entrepreneurship transition follows an “inverted U-shaped” curve with experience: individuals are less likely to make the transition when they are either very early in their career or very far into it. This means that even for someone with strong corporate experience, timing and personal readiness matter deeply. This highlights the need for deliberate planning, not simply confidence alone.
“Many HNWIs reach a point where professional success no longer equates to personal fulfilment. They seek impact, freedom and meaning to align their work with who they’ve become, not just what they do,” says Zungu.
The pursuit of entrepreneurship is often a quest to create value on one’s own terms, she says. “Beyond the pursuit of autonomy and impact, legacy and succession planning are also significant motivators. It’s about creating something enduring that not only reflects their values but also provides a legacy vehicle for future generations.”
BETTER RISK MANAGEMENT FOR GREATER SUCCESS
Zungu advises that new ventures should be calculated strategies, not leaps of faith. “Be careful about overconfidence and under-preparation.”
“It starts with understanding both your financial position and long-term objectives, including detailed cash flow and balance sheet analyses to reveal capacity for volatility and to identify potential funding gaps.”
You should not overlook the structural safety nets that corporate life provides, such as group risk cover, medical aid and retirement benefits, says Zungu. “You must intentionally recreate these safeguards in your personal capacity. While using personal life savings and investment portfolios to fund the new venture demonstrates commitment, it exposes individuals to potential liquidity constraints and capital erosion. Without proper separation between business and personal estates, the ripple effects can threaten your family legacy.”
“Secondly, aspiring entrepreneurs should start with a simple strengths, weaknesses, opportunities and threats (SWOT) analysis to understand industry dynamics, competitive forces and potential threats or opportunities, to enable informed decision-making.
“Lastly, the most successful transitions are phased. Leveraging corporate stability to incubate an entrepreneurial venture allows for growth without financial panic. Once the business achieves sustainable cash flow and structural soundness, full transition becomes viable.”
Her advice is echoed in this Entrepreneur.com article, which highlights that entrepreneurs who first tested a business idea not only mitigated risk, but created breathing room to refine their proposition before taking the leap.
For professionals in South Africa, where economic conditions, access to capital and employment dynamics are often more challenging, this offers an important practical lesson: assemble your parachute carefully while still connected to a safe runway.
SURVIVING EARLY EMOTIONAL ROLLERCOASTERS
“Launching a startup can be summed up in one word: rollercoaster,” says Zungu. “Corporate life often provides structure, identity and external validation. The shift can create a void and trigger imposter syndrome, stress, anxiety, self-doubt and even loneliness. One should feel and acknowledge these emotions but not be driven by them.”
Key to minimising the “rollercoaster effect” is to avoid setting unrealistic deadlines for success. “What matters most is preparation, readiness and proficient execution, not stringent timelines, as that can exacerbate emotional and psychological challenges.”
FINDING NEW PASSION AND PURPOSE
Define the impact you wish to create, then allow your financial strategy to enable that purpose. “As Simon Sinek says, start with your why, because purpose drives endurance. Build a team of experts who both challenge and support you and recognise that success is not defined by speed, but by sustainability.”
“The most successful transitions share a common trait: intentionality. The clients who had the most successful transitions didn’t chase escape, trends or instant gratification; they pursued alignment and patiently built the right ecosystem around them. They understood that wealth creation is also about human and intellectual capital and they invested accordingly.”
While passion may drive the new venture, concentration risk can quietly erode wealth, she cautions. “Maintaining balanced portfolios, establishing liquidity reserves and applying sound capital structuring principles ensure financial agility and long-term value creation. Business assurance, liquidity planning and appropriate risk management are critical components of a sustainable transition strategy.”
CONCLUSION
The key to a safe transition to entrepreneurial freedom is engaging professional advice early on, to achieve “disciplined autonomy”, says Zungu. “Freedom without structure is chaos.”
“You must continuously review the feasibility and viability of the business, regularly testing assumptions, adjusting strategies and ensuring both operational practicality and long-term profitability. Financial advisors act as financial directors of one’s life, to structure liquidity, protect wealth, manage tax implications and ensure the business’s risk exposures don’t compromise family security.”
“It’s about moving from income dependency to capital efficiency, transforming how wealth works for business owners, not just how they work for wealth.”
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