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Financial Planning for Pre-Retirees & Gartner Employees

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Questions to Ask If Navigating a Solo Retirement

Embarking on retirement alone, either by choice or due to unforeseen circumstances such as the loss of a partner or divorce, presents a unique set of challenges and considerations. With the rise in divorce rates among those aged 50 and older, and the reality that over a quarter of individuals over 60 live solo – a figure that climbs significantly for women as they age – preparing for a solo retirement is more relevant than ever.

How Will You Remain Socially Connected?

Social connections and a robust support network are crucial for a fulfilling retirement, especially when navigating this journey alone. Loneliness and isolation can have significant impacts on both mental and physical health. Therefore, it’s essential to proactively seek out social engagement and build a community that supports you. Consider the following strategies:

  • Join clubs or groups that align with your interests, such as book clubs, gardening groups, or exercise classes.
  • Volunteer for causes you’re passionate about, offering a sense of purpose and the opportunity to meet like-minded individuals.
  • Stay active in the digital world, using social media and video calls to keep in touch with friends and family, especially those who might not be nearby.

Are You Retiring in the “Right Place?”

The choice of where to retire is pivotal, especially for those living alone. The “right place” is not just about affordability or scenic beauty; it’s also about the support structures available, accessibility to healthcare, and opportunities for social interaction. Consider these factors:

  • Community and services tailored for retirees, including recreational centers, continuing education classes, and easily accessible healthcare facilities.
  • Proximity to family and friends, ensuring you have a support network within reach.
  • Safety and accessibility, including public transportation options, walkable neighborhoods, and communities with other single retirees.

Who Will Care for You?

While it may be uncomfortable to think about, planning for potential health care needs is a critical aspect of preparing for solo retirement. Anticipating who will assist you in case of health issues and understanding the resources available can help you work towards peace of mind.

Strategies include:

  • Long-term care insurance, to cover costs of care that regular health insurance may not. You may consider reaching out to your financial professional to determine if long-term care insurance is right for you.
  • Health directives and living wills, ensuring your wishes are known and respected. Contact a legal advisor to assist you with the process. 
  • Building a trusted networkof friends, family, or professionals who understand your preferences and can advocate on your behalf.

Embracing Solo Retirement

Living solo in retirement is an opportunity to craft a life that truly reflects your interests, values, and desires. It encourages self-reliance and resilience, offering the freedom to pursue passions without compromise. Embracing this stage with preparation and positivity can lead to a richly rewarding experience.

  • Develop new skills or hobbies that you’ve always wanted to explore.
  • Travel solo, experiencing the world on your own terms.
  • Invest in self-care, recognizing that taking care of your mental and physical well-being is paramount.

Solo retirement is not just about facing challenges; it’s about seizing opportunities to live a life filled with joy, purpose, and community. By asking yourself these critical questions and planning accordingly, you can confidently pursue a retirement that is vibrant and fulfilling.

Important Disclosures

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

Strategies include:

  • Long-term care insurance, to cover costs of care that regular health insurance may not. You may consider reaching out to your financial professional to determine if long-term care insurance is right for you.
  • Health directives and living wills, ensuring your wishes are known and respected. Contact a legal advisor to assist you with the process. 
  • Building a trusted networkof friends, family, or professionals who understand your preferences and can advocate on your behalf.

Embracing Solo Retirement

Living solo in retirement is an opportunity to craft a life that truly reflects your interests, values, and desires. It encourages self-reliance and resilience, offering the freedom to pursue passions without compromise. Embracing this stage with preparation and positivity can lead to a richly rewarding experience.

  • Develop new skills or hobbies that you’ve always wanted to explore.
  • Travel solo, experiencing the world on your own terms.
  • Invest in self-care, recognizing that taking care of your mental and physical well-being is paramount.

Solo retirement is not just about facing challenges; it’s about seizing opportunities to live a life filled with joy, purpose, and community. By asking yourself these critical questions and planning accordingly, you can confidently pursue a retirement that is vibrant and fulfilling.

Important Disclosures

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

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Brian P. Skinner

Forbes Best-in-state Wealth Advisors 2025

AdvisorHub Solo Advisors to watch 2025

Brian P. Skinner, CFP®, CRPC®

Financial Planner

Professional Philosophy

Brian is a dedicated financial planner who is passionate about retirement and investment planning. He is internally driven, every day, to make the experience and the firm, the best in the industry. He specializes in tax-sensitive retirement and income distribution planning for individuals and families aged 50+, helping them navigate the transition from saving for retirement to spending in retirement. His approach integrates investment management, risk planning, and tax-efficient strategies into comprehensive financial plans tailored to clients’ unique goals.

He believes deeply in the value that linking investment, tax, and income planning together provides in his pursuit of helping clients attain financial flexibility and retire confidently.

Industry Awards & Designations

Brian’s expertise and dedication have earned him notable recognition within the financial planning industry. In 2024, he was honored with the Forbes Best-in-State Next Gen award for financial advisors in Connecticut. He holds the prestigious Certified Financial Planner™ (CFP®) certification and the Chartered Retirement Planning Counselor (CRPC®) designation, underscoring his commitment to professional excellence and fiduciary responsibility.

The Forbes ranking of Top Next-Generation Wealth Advisors, developed by SHOOK Research, is based on an algorithm of qualitative and quantitative data, rating thousands of wealth advisors born in or after 1980. Advisors are interviewed by telephone and in person to evaluate service models, investing process, experience levels and integrity. Additional factors considered include compliance record, client retention, revenues produced for their firms and assets managed. Portfolio performance is not a criterion due to varying client objectives and lack of audited data. Neither Forbes nor SHOOK receives a fee in exchange for rankings.

Education & Background

Brian grew up with his family in Orange, CT, moving through the local school system and eventually graduating from the University of Connecticut; he actively expands his industry knowledge through daily continuing education efforts, ensuring he remains at the forefront of financial planning strategies. His passion for educating others extends beyond his practice; he has taught classes on retirement planning, tax strategies, and smart investing across numerous towns in Connecticut.

Personal Passions & Community Engagement

Brian resides in Milford, CT, where he is deeply involved in the community. He is an active member of the Milford Rotary Club and has served as Corporator of Milford Bank and formerly as Corporator of Milford Hospital. Beyond his professional endeavors, Brian enjoys reading, perfecting his golf swing, and spending time with his wife, Kristine, and their son, Graham Skinner. He loves to put Graham in the hiking backpack to get outside to explore and embrace nature. Brian’s commitment to community involvement reflects his belief in fostering meaningful personal and professional connections.

Brian with his wife and their son at 4 month old
Brian hold his son with snow
Brian with his wife and their son as a toddler with Santa
Brian feeding his young son
Brian with his son in a hiking kid backpack on a hiking trail
Brian with his wife at a wedding

Nominees are required to have a minimum of seven years experience, $100m minimum AUM, and a clean regulatory record. Using data on assets, households, and production, advisors are ranked on three categories: scale, growth, and professionalism. The list is broken into several sublists: RIAs (fee-only), Over $1b, Under $1b, Next Gen, Women, Solo, and Fast-Growing. Please note that participation in this ranking is free, and AdvisorHub receives no compensation from the participating advisors.

Jeff Costa

Jeff Costa, CFP®

Financial Planner

At Skinner Wealth Strategies, we understand that navigating the world of finance can be overwhelming. That’s where Jeffrey comes in. As a Certified Financial Planner with a passion for crafting tax-sensitive financial plans and investment strategies, Jeffrey is dedicated to helping you achieve your financial goals.

Jeffrey joined the Skinner Wealth Strategies team in February 2025, bringing with him a wealth of experience from his previous roles. He served as a financial advisor and portfolio manager at Scholtz and Co, enhancing his expertise in managing investments for diverse client needs. Before that, he honed his skills as a Trust & Investment Officer at First County Advisors for four years, and started his career in 2009 at Barnum Financial Group, where he first discovered his passion for guiding clients through their financial journeys.

Holding a B.A. in Economics and Political Science from the University of Connecticut, Jeffrey has been a Certified Financial Planner since 2017. His extensive knowledge and approachable demeanor make him an invaluable resource as you make important decisions about your financial future.

Outside of work, Jeffrey balances his professional drive with family life in Fairfield, CT, where he combines his love for travel, cooking, and water sports. He understands that life is about creating memorable experiences and is committed to helping you fund those dreams.

Jessie Morotto

Jessie Morotto, FPQP®

Operations Manager

Jessie joined the team in 2017 and has had experience in the insurance industry since 2014. As a licensed Operations Manager, her focus is on assisting clients during their financial planning and asset management experience. She is our first point of contact, handles many different service requests and keeps everything running smoothly.

Jessie is an avid traveler, when you meet her ask her about where she’s been and where she plans on going. When she’s not working or on an airplane, you can typically find her doing yoga, reading, or with her friends and family.

Margo Bivins

Margo Bivins

Relationship Manager

Margo joined the team in 2022 and has had 23 years of experience in the insurance industry.

As our relationship manager, her focus is to bring the highest level of service to our clients assisting you however she can. Her goal is to “WOW” you with our service.  Margo looks forward to building meaningful and productive client relationships.

 Margo enjoys traveling. For her, a good day is a beach day, with great friends. She loves spending quality time with family and friends and always enjoys a great Zumba or HITT workout.

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