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10 Ways Stretch Goals Drive Success for High-Net-Worth Individuals


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For high-net-worth individuals, reaching financial success is just the beginning. The real challenge lies in unlocking your full potential and creating a legacy that goes beyond monetary wealth. One way to push beyond the limits of conventional success is through stretch goals—objectives that are not just ambitious but designed to drive you out of your comfort zone and into extraordinary achievement.


“The way to get started is to quit talking and begin doing”

                                                                — Walt Disney


Stretch goals are not about incremental gains; they are about challenging the boundaries of what you believe is attainable. As Harvard Business Review explains, "The power of a stretch goal lies in its ability to push us beyond incremental improvements and into the realm of innovation and transformation" (Sitkin, 2020). This is especially true in wealth management, where the stakes are high, and the potential for growth is vast.


What Are Stretch Goals?

Stretch goals are ambitious targets that require innovative thinking, risk-taking, and perseverance. They are meant to be difficult, forcing you to think beyond the typical approaches that have brought you success in the past. In contrast to typical, "safe" goals, stretch goals are often big that achieving them seems improbable—but it’s precisely this challenge that leads to exponential growth.

For high-net-worth individuals, the concept of a stretch goal in wealth management could involve making significant philanthropic contributions, investing in innovative industries and at times, even doubling your assets in a set period. The goal is to challenge yourself beyond your usual limits, which can open the door to financial outcomes that might surpass your expectations. Consult with a financial advisor to gain a comprehensive understanding of potential risks and uncover the most effective strategies for managing them.


How to Implement Stretch Goals in Financial Planning

To apply the power of stretch goals to your financial journey, follow these key steps:


1.    Define Your Vision

The first step in setting a stretch goal is defining a bold financial vision that excites and challenges you. Ask yourself: What would your financial future look like if you aimed for something truly ambitious? For example, instead of aiming to increase your portfolio by 10%, consider a goal of doubling your wealth over the next decade. Your vision should be both compelling and motivating.


2.    Take Calculated Risks

Stretch goals require stepping into the unknown, which often involves taking calculated risks. High-net-worth individuals may need to venture into areas that feel unfamiliar or unconventional—such as alternative investments, venture capital, or private equity deals. As Sitkin (2020) notes, "stretch goals are valuable when they push people to innovate and explore new possibilities." Taking strategic risks can open doors to untapped financial opportunities.


3.    Embrace Failure as a Learning Tool

Stretch goals come with inherent uncertainty. There’s a possibility that not every decision you make will lead to immediate success. However, setbacks should be seen as part of the process, not the end. By treating failure as a learning opportunity, you can refine your strategies and continue striving toward your larger goals. As Asana, a work management company that's designed to help teams organize, track, and manage their work, highlights, “stretch goals can help you boost team performance and increase team morale by encouraging innovation, productivity, and commitment” (Asana, 2024). The road to achieving stretch goals may be rocky, but the long-term payoff can be extraordinary.


4.    Create a Measurable Plan

While stretch goals are ambitious, they still need to be measurable. Break down your stretch goal into actionable steps and establish key performance indicators (KPIs) to track your progress. This is particularly important when managing large sums of wealth or complex investment portfolios. Monitoring your progress will help ensure you stay on track and make necessary adjustments along the way.


5.  Leverage Expert Guidance

Pushing beyond the boundaries of conventional wealth management requires the expertise of seasoned advisors. Surround yourself with a team that understands the complexities of managing large assets and can offer innovative financial strategies. A skilled financial advisor can help you assess risks, navigate new markets, and maximize your investments.


6.  Diversify Your Portfolio

Stretch goals often involve venturing beyond familiar investment vehicles. Consider diversifying your portfolio into emerging industries, such as sustainable energy, biotechnology, or fintech. Diversifying in this way not only mitigates risk but also opens up new avenues for substantial returns.


7.  Aim for Legacy, Not Just Wealth

High-net-worth individuals often reach a point where building more wealth for themselves is no longer the primary goal. Stretch goals can help shift your focus toward creating a legacy. This could mean investing in philanthropic endeavors, creating generational wealth, or funding innovative projects that align with your values. The larger and more impactful the goal, the greater the personal and financial rewards.


8.  Utilize Your Network

One of the greatest advantages of being a high-net-worth individual is access to a powerful network. Use this network to your advantage by partnering with other like-minded individuals on bold investment opportunities, collaborative projects, or philanthropic ventures. Stretch goals are easier to achieve when you leverage the collective expertise and resources of a strong network.


9.    Regularly Reassess Your Goals

Stretch goals are dynamic and achieving one might open up the possibility for even greater aspirations. Regularly reassess your goals and adjust them as needed. This iterative approach keeps you aligned with your evolving financial circumstances and ensures you are always working toward meaningful, ambitious targets.


10.  Celebrate Milestones Along the Way

Achieving a stretch goal is a long-term process, and it's important to recognize and celebrate the milestones you reach along the way. Each step brings you closer to realizing your ultimate vision, and acknowledging these achievements can fuel your motivation to continue striving for more.

 

“Don’t be afraid to give up the good to go for the great.”  

  – John D. Rockefeller


When Stretch Goals Work Best

It's important to understand that stretch goals are not a one-size-fits-all solution. According to change management coach Wendy Hirsch, they work best under specific conditions:  


  • When viewed as a rare opportunity: Stretch goals can be energizing and motivating when seen as a unique chance to achieve something extraordinary.

  • When recent success signals capability: Recent achievements can demonstrate the ability to effectively utilize resources and capabilities.

  • When available resources support learning: Adequate resources can reduce the pressure of trade-offs, supporting openness and learning.

  • When efforts focus on new learning: Stretch goals should emphasize innovative approaches and learning to reach the desired outcomes (Hirsch, 2024) 


These conditions ensure that stretch goals provide the greatest benefit without causing undue stress or unrealistic expectations.

 

The Power of Stretch Goals for High-Net-Worth Individuals

For high-net-worth individuals, stretch goals challenge the status quo and push you to achieve results that may have once seemed impossible. By applying this mindset to your financial strategy, increasing your net worth, diversifying your investments, or leaving a lasting legacy, the stretch goal framework will help you progress toward extraordinary outcomes.

 

The Power of Stretch Goals for Sports and Entertainment Professionals

For sports and entertainment professionals—whether up-and-coming athletes, current stars, or retired players—the stretch goal framework is equally powerful. As you navigate a high-profile career, your financial strategies should match your ambition on and off the field. Up-and-coming players can set stretch goals to build long-term wealth while balancing immediate opportunities. In contrast, current players can aim for diversified investments that secure financial stability beyond their athletic careers. Retired players, too, can use stretch goals to ensure their legacy extends through smart investment strategies and philanthropic efforts. No matter your stage, the principle of aiming for bold, transformative goals can drive financial success and lasting fulfillment.

 

“The difference between ordinary and extraordinary is that little extra.” 

– Jimmy Johnson


As financial advisors, we are here to help guide you through this journey. With expert insights, strategic planning, and a clear vision for your future, stretch goals can become the catalyst for your most significant financial achievements.


For more financial tips and wealth-building insights, subscribe to our newsletter here. To explore how our expertise can benefit you in the sports and entertainment industry, visit our Sports & Entertainment division here.


References

Sitkin, S. B. (2020, December 9). The stretch goal paradox. Harvard Business Review. https://hbr.org/2017/01/the-stretch-goal-paradox

Asana, T. (2024, February 5). How to Set & Track Stretch Goals to Inspire Your Team [2024]. Asana. https://asana.com/resources/stretch-goals

Hirsch, W. (2024, June 5). Which type of goal has the greatest impact on performance? Wendy Hirsch. https://wendyhirsch.com/blog/goal-setting-which-type-works-best

 


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