Entrepreneurship: Can You Afford to Put All Your Eggs in One Basket?

Thomas Jefferson said: “Our greatest happiness does not depend on the condition of life in which chance has placed us, but is always the result of a good conscience, good health, occupation, and freedom in all just pursuits.”

This has been one of my favorite quotes since I was a teenager and to this day. Jefferson believed true happiness is not determined by external circumstances, wealth or social status but by internal factors within our control. I didn’t grow up poor, but my parents were not wealthy, more middle class. They lived a better life than their parents. I owe everything to them for putting my interest in technology and the internet first.

For many adults without savings or financial support from family, a single job or business failure can be disastrous. That’s why we diversify our income streams through part-time jobs, startups or ventures in completely unrelated fields. It’s about survival and reducing one’s exposure to catastrophic risk.

This does not imply that one group works harder than the other—both face different challenges. But the consequences of failure are much worse for those without a financial buffer which often forces them to hold on to their full-time jobs longer.

Let’s dive into why this is the case and why lower income families are more likely to have multiple jobs or ventures while wealthier individuals can afford to have just one regardless of the outcome. And why we shouldn’t automatically downplay or dismiss those who were able to make the most of where “chance has placed” them.

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Financial Safety Nets

Steve Jobs, Bill Gates, Mark Zuckerberg, Jeff Bezos and Elon Musk—icons of innovation and entrepreneurship—each had the financial backing and support to take the big risks in building their empires.

Bill Gates, whose father was a lawyer, had the privilege of attending elite schools and had the resources and conveniences to start Microsoft.

Mark Zuckerberg grew up in an upper middle-class family and his father, a dentist, gave him early access to technology so he could work from his Harvard dorm room without fear of financial disaster.

Jeff Bezos’s family invested heavily in Amazon’s early days with his parents reportedly putting in nearly $250,000 in early Amazon.

Elon Musk came from a very wealthy family in South Africa which gave him the foundation to take big risks.

Steve Jobs was adopted into a financially comfortable family, which gave him the freedom to build Apple without the pressure of financial survival. But there’s a lesson that applies to all of us regardless of our current wealth, which we can learn from his story. We will get to that later.

Each of them had a financial safety net which gave them the freedom to focus on their ventures without the threat of financial collapse that could affect their well-being or their family’s well-being.

Generational wealth provides access to more savings and family support, which fundamentally changes the way risk is perceived. Wealthier individuals can fully commit to one venture because their primary concern isn’t survival—it’s success. They can take bigger risks, invest more time and energy into their ideas and recover more easily if things don’t go as planned.

And they often have access to resources like mentorship, connections and higher education that mitigate these risks—unlike the risk of losing their home, compromising their children’s education or running out of food.

But that doesn’t mean those born into wealth don’t work hard or take risks. The difference is in the level of consequences they face. I find it more disappointing when those with generational wealth don’t take advantage of top-tier education, don’t get involved in family businesses or take a lazy approach to their opportunities. It’s more understandable when those without financial safety nets don’t want to expose themselves and their family to financial disaster. In my circle of friends, I’ve been fortunate to see many hardworking risk takers who make the most of what they have, regardless of their wealth background.

All or Nothing: The Fear of Lower Income Families

For lower income families, the idea of putting everything into one business or job feels like a gamble with extremely high stakes. When you don’t have a financial safety net, failure isn’t just a setback, it can be devastating. Losing a steady income could mean not being able to pay rent, mortgage, utilities, health insurance and of which can affect mental health. That’s why they often take a more cautious approach by diversifying their income streams to reduce the risk of any one job or venture failing.

By having multiple income streams, individuals can withstand a sudden loss of one. For example, if a business startup fails, they still have their main job to fall back on or vice versa. It’s a practical way to avoid total financial collapse. The ability to keep stability and security for their family often trumps the potential rewards of taking more risk by focusing on one thing.

Lower income individuals have to manage their risk more carefully. For them, the phrase “all or nothing” can be a reality and the consequence of “nothing” is more immediate and severe.

Another thing is that many side businesses or extra jobs can grow to be more profitable than the person’s main job over time. This gradual transition allows them to keep their financial security intact while slowly shifting more attention to their entrepreneurial ventures if they start to take off. Juggling multiple jobs isn’t about being unfocused or scattered, it’s about mitigating risk and increasing long term financial security.

Cultural and Societal Influences

In many countries including the Caribbean region I was born into the idea of working multiple jobs or juggling different ventures is deeply ingrained in the culture. It’s often seen as being responsible and a sign of personal ambition.

In regions where job security is low and wages are stagnant people may take on multiple jobs out of necessity. It’s become part of the collective mindset that one job is never enough for financial stability. In countries with limited social safety nets families may feel a cultural pressure to hustle and generate income from multiple sources to protect themselves from economic downturns.

The Time Dilemma: Full-Time Job vs. Passionate Venture

For those juggling a full-time job with a passion project or startup, the big challenge is often time. Splitting focus between a steady job and a new venture can significantly reduce the chances of success for the startup. The energy and attention required to build a business is challenging to sustain when the individual has to also perform at their main job. Balancing both can lead to burnout, slow progress and missed opportunities.

A full-time job takes up a person’s most productive hours of the day, leaving their passion project with the leftovers and energy. This limits how much they can put into growing their business, networking or even learning from mistakes. Someone with financial freedom has more time to give their venture full attention.

The pressure of having a full-time job can stifle creativity and innovation. When you’re tied to a paycheck for survival it’s harder to take bold risks or invest in long-term strategies. The startup or venture will remain small or stagnant because the creator can’t afford to fully engage with it. Those with financial backing can take bigger swings because they know they won’t lose their livelihood if things don’t pan out immediately.

This difference in time and focus means that entrepreneurs with financial freedom prove to have a higher chance of success. They can pivot faster and put all their resources into one basket without having to split their focus and time between multiple income streams.

A Key Lesson for Entrepreneurial Success

One key lesson from Steve Job’s story is the importance of seeking investors and partners with access to capital, especially in the early stages of building a business. Jobs, along with Steve Wozniak had a vision for Apple, but it was their ability to secure the backing of Mike Markkula an early investor, that really moved the company forward.

Markkula provided not only financial support, but also business expertise that was crucial to Apple’s growth. Today’s aspiring entrepreneurs can do the same by networking with potential investors who believe in their vision, attending startup events and seeking out complementary business partners.

Building a successful venture often requires finding the right people who can provide financial backing, mentorship and strategic advice to navigate the challenges of scaling a business. By doing so, entrepreneurs can reduce their personal financial risk and bring their ideas to life.

Conclusion

The dynamics of wealth, security and entrepreneurship are very different for those with financial safety nets and those without. For the wealthy, the ability to focus full-time on their ventures knowing they can recover from failure allows them to take risks others can’t. For those from lower income backgrounds, they need to juggle multiple jobs or ventures to create a stable foundation and reduce the risk of catastrophic failure.

This doesn’t mean one group works harder than the other – both have unique challenges. But the consequences of failure are much more severe for those without a financial cushion, which often forces them into more conservative approaches like holding on to their full-time job longer. Some may never have the luxury of dedicating all their time and energy to one passion project.

As someone who has launched several startups while working full-time on the Caribbean island of Antigua, I know this dilemma first hand. In 2007, my online startup was earning more than double my full-time salary for a full year, and I still hesitated to go all in.

It wasn’t until my employer let me go due to a conflict of interest that I was finally forced to embrace the freedom, peace of mind and better quality of life that came with leaving the 9 to 5. This move didn’t make me rich, but being able to focus full-time on my ideas and my businesses allowed me to become more aligned with Thomas Jefferson’s words at the beginning of this article. Within my business, I diversify across three main niches for the reasons mentioned earlier.

By acknowledging the realities of both sides, we can understand why people make the choices they do. And make better choices for our businesses.