Risk-Taking vs. Playing It Safe: How Coaching Fuels Career Advancement Across Cultures

I had an interesting coaching conversation with a client that inspired this blog and had me do a deep dive on culture and its role on our health, decision making and how that impacts generations to come after us.

My family, like this client, is from Jamaica, West Indies. Growing up in Jamaica, Queens, I grew up around immigrants owning businesses. All of Jamaica, Queens is small businesses run by people of color and mostly immigrants. But through coaching, and specifically this conversation with my client, I decided to scrutinize this a little more.

Risk-taking in Jamaican culture is often influenced by a blend of individual ambition, family responsibilities, and the desire for stability. In contrast to more individualistic Western cultures that prioritize personal career advancement, Jamaicans tend to make career decisions that balance personal aspirations with the needs of their family and community. This emphasis on collective success is shaped by historical, economic, and cultural factors.

On the surface this seems nice but think about the economic disparities in America, which I outline in my blog here. Not taking the risk to go for more income actually hurts the family. I see that it is hurting with so much mental space taken up by making financial decisions over food. If you are above the poverty line, then you need to read my book here.

For many Jamaicans, particularly those in lower-income brackets, career risk-taking might be seen as a luxury. There is a cultural tendency to play it safe by choosing jobs that provide stability, such as government positions or teaching, where job security and benefits are more assured. Risking a steady income to pursue entrepreneurial ventures or career changes may be viewed as jeopardizing family welfare, which is highly valued in Jamaican society. This cautious approach to career moves often limits financial growth and wealth accumulation.

When you limit financial growth, your ability to make healthy choices is restricted. You are also limiting the quality of life by not being able to provide the cleanest and healthiest food and environment for your children or aging parents. I hear too many people trying to fit into the box of having not enough resources, without putting in any effort to work towards building more resources.

The focus on stability can have a long-term impact on generational wealth. By prioritizing secure but often lower-paying jobs, many Jamaican families may experience slower financial growth. This cautious approach can also delay entrepreneurial ventures or innovative career moves that might lead to higher incomes and more significant financial freedom. Over generations, this creates a pattern where financial risk is minimized, but so are opportunities for substantial economic mobility.

My mom has said, “As for me and many others we became successful by leaving Jamaica ???? to come to this country, I know it wouldn’t happen for me staying in Jamaica, Just speaking from personal experiences.” I have seen my grandmother’s children become homeowners and have cars with garages but health issues amongst my cousins in their 40s and 50s are halting that wealth growth with their generation.

It’s surprisingly easy for people to fall out of the middle class, especially in times of economic downturn or major life changes like job loss or a health crisis. Statistics show that the share of Americans in middle-income households has shrunk over time. In 1971, 61% of adults in the U.S. were part of the middle class, but by 2021, that figure had fallen to 50%. Many people who were once middle class have found themselves slipping into the lower-income bracket due to rising costs of living and slower wage growth relative to upper-income households. For example, one study shows that 32% of adults who were in the middle-income tier in 2020 were no longer in that tier by 2021, with 16% moving down into the lower-income tier (Pew Research Center)(World Economic Forum)(Pew Research Center).

This trend disproportionately impacts certain demographics. Black and Hispanic adults, for instance, are more likely to move down from the middle-income tier to lower-income households, with around 22% of Black adults and 20% of Hispanic adults experiencing this setback annually. In contrast, only 15% of white adults and 12% of Asian adults experience the same drop (Pew Research Center). These patterns reflect a broader racial wealth gap, where Black and Hispanic households have less wealth to fall back on during financial hardships (Pew Research Center)(Pew Research Center).

The hollowing out of the middle class can also be attributed to slower income growth in middle-income households compared to upper-income households. Middle-class incomes grew by only 50% from 1970 to 2020, while upper-income household incomes grew by 69% (World Economic Forum). This widening gap makes it harder for middle-class families to maintain their economic standing.

Understanding these trends can help shine a light on why risk-taking in career moves, financial planning, and wealth-building becomes critical, especially for Black women and those nearing retirement or with family obligations.

At the same time, in Jamaican culture, there is a strong entrepreneurial spirit, with people taking calculated risks to start small businesses, particularly in communities with limited formal employment opportunities. Although these businesses can be unstable, they offer a chance to break out of economic stagnation, leading to improved financial outcomes for future generations. My parents' entrepreneurship allowed for me to go to private schooling, get music and dance lessons, and helped pay for college. They even invested in my brick and mortar business.?

The key lies in entrepreneurship and, more importantly, working on mindset with a coach to understand and appreciate your own value and the worth of what you have to offer, thus avoiding undervaluing yourself in the marketplace. Some people leave corporate America only to find themselves struggling financially as business owners, as there is more risk involved.

In Jamaican culture, career decisions often weigh the need for individual success against the responsibilities to family and community. While this can lead to stable, predictable income streams, it can also hinder the kind of bold risk-taking that might yield greater financial rewards over time. Those who successfully navigate this balance—especially entrepreneurs—can create generational wealth and shift the financial trajectory of their families.

Given the rising cost of living and stagnant wages for middle-income earners, what do you think is the best way for people to maintain or improve their financial situation?