Build Your Dream Retirement With These Five Steps

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published 2 February 2025

Retirement is more than just the end of your working years; it’s the beginning of a new chapter filled with potential, purpose and possibility. While financial security is a cornerstone, designing a fulfilling retirement requires a holistic approach that aligns your goals, passions and resources. Here’s how to lay the groundwork for a retirement that reflects your values and dreams:

1. Start with your 'why'

Understanding the core motivation behind your retirement is the first and most critical step. What are you seeking from this phase of life? Is it freedom from work, time to explore hobbies or deeper connections with family?

Client story: Steve and Linda approached retirement with different visions. Steve pictured days on the golf course and evenings playing poker, while Linda dreamt of European adventures and wine tastings. By openly discussing their "why," they uncovered shared goals and crafted a retirement plan that honored both their individual and collective dreams.

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Practical tip: Take time to journal your motivations for retirement. Reflect on questions like:

What excites me most about retiring?
What legacy do I want to create?
How do I want to spend my time?

By anchoring your plans in a clear "why," you’ll make more intentional and satisfying decisions.

2. Define your 'what'

With your "why" established, focus on defining what you want your retirement to look like. A detailed vision can help transform abstract dreams into actionable steps.

Key areas to explore:

Travel: Whether it’s exploring national parks in an RV or cruising the Mediterranean, envision your ideal adventures and set priorities.
Social engagement: Without the natural social structures of work, staying connected is crucial. Consider joining clubs, volunteering or fostering community relationships.
Health and wellness: Retirement is an opportunity to prioritize physical and mental health. Activities like yoga, hiking or swimming can keep you active and engaged.
Hobbies and passions: Dive into creative pursuits such as painting, gardening or woodworking. These outlets can provide joy and fulfillment.

Best practice: Test drive your retirement lifestyle. Before fully retiring, take an extended vacation or reduce work hours to simulate your envisioned routine. This trial run can reveal areas needing adjustment.

3. Map out your 'how'

Once your "why" and "what" are clear, it’s time to develop your roadmap for achieving them. Financial planning is a critical component, but it should align with your personal goals.

Pro tip: Begin by crafting a year-one retirement budget. Include anticipated expenses such as travel, health care and discretionary spending. Be sure to account for inflation and unexpected costs.

Case study: A couple we worked with had a robust plan for their first retirement year, focusing on traveling across the U.S. However, a family emergency required reallocating funds. Because they regularly reviewed their financial plan, they were able to adapt without sacrificing their long-term goals.

4. Stay flexible

Retirement isn’t static. Your needs and desires may evolve as you settle into this new chapter. Flexibility is key to navigating these changes.

Advice: Schedule regular check-ins with a fiduciary adviser to reassess your financial and personal goals. Quarterly or annual reviews can help you:

Adjust your budget based on market performance or unexpected expenses
Refine your goals as new opportunities or challenges arise

Real-life example: Steve and Linda found unexpected joy in RV travel, blending their love for adventure and sports. Their willingness to adapt ensured their retirement was both fulfilling and financially sustainable.

5. Build a legacy

Retirement isn’t just about enjoying life — it’s also an opportunity to leave a lasting impact. Whether through charitable giving, mentoring or supporting family, consider how you want to be remembered.

Best practice: Establish a charitable giving plan that aligns with your values. Tools like donor-advised funds can simplify the process and maximize tax efficiency.

Client insight: One retiree, a former teacher, found purpose in mentoring underprivileged youth. This effort enriched his retirement and made a significant difference in his community.

The bottom line

A fulfilling retirement is built on more than just financial stability. It’s about aligning your resources with your values, staying adaptable, and embracing opportunities for growth and connection. By starting with your "why," defining your "what" and crafting a flexible "how," you’ll create a retirement as unique as you are.

Take the first step today. Reflect on your goals, connect with a fiduciary adviser and start shaping the retirement you’ve always envisioned. The journey is yours to design — make it extraordinary.

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Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

Keith Wiltfong, CFP®, is the Founder of Capstone Investment Management, LLC. A Yale-certified Certified Investment Management Analyst®, he focuses on holistic financial planning, providing clients with a comprehensive, actively managed, results-oriented, progressive and sustainable money management platform. He holds a Series 65 securities license as well as insurance licenses in various states.