Planning For The Life You Want
Retirement is a major transition. We assist you in more than just your finances. We help you think through the lifestyle, health, and personal changes—so you’re fully prepared for what comes next.
Retirement Prep
Retirement is a major life transition that involves much more than finances. In fact, many soon-to-be retirees feel confident about their savings but still don’t feel emotionally or socially prepared for the changes ahead.
In the years leading up to retirement, it’s crucial to plan for the non-financial aspects—from daily lifestyle changes and identity to relationships, health, and even where you’ll live. Evidence shows that attending to these areas can significantly improve your well-being and satisfaction in retirement.
Why Non-Financial Planning Matters
Focusing only on money isn’t enough for a successful retirement. While financial security is important, studies show that neglecting the emotional and lifestyle aspects of retirement can have harmful consequences for well-being.
The good news is that with proactive planning, you can avoid many of these pitfalls. It's recommended that you envision your retirement in terms of five key dimensions:
In other words, retirement readiness should be holistic, balancing how you’ll spend your time, who you’ll spend it with, how you’ll stay healthy, what will give you purpose, and where you’ll live.
By addressing these non-financial factors over the next few years, you’ll set yourself up for a smoother transition and a more rewarding retirement life.
Timeline For The Coming Years
The transition to retirement can be broken into several years to prepare thoughtfully for both financial and personal changes.
Laying the Foundation
- Envision a typical week in retirement: sketch out a sample schedule.
- Identify hobbies or interests you want to explore.
- Build a bucket list with timing (what must happen while you’re healthiest/mobile vs. later).
- Decide whether you prefer a phased transition (part-time/consulting) or a full stop, and identify what you’d need for either path.
- Complete a full preventive screening plan and establish a “health trajectory” baseline (labs, checkups, specialist needs).
- Build sustainable healthy habits: daily movement + nutrition plan + stress management routine you can keep in retirement.
- Document family medical history and identify likely future needs (mobility, cognitive health, chronic conditions).
- Start Medicare education: understand parts A/B/C/D, and note whether you’ll retire before 65 (coverage gap planning).
- Decide whether you’re likely in a “forever home” and create 2–3 location scenarios (stay, downsize, relocate).
- Assess walkability, amenities, and proximity to specialized healthcare; list must-haves for your retirement lifestyle.
- Start decluttering: identify what possessions no longer serve you and create a staged downsizing plan.
- Have a structured conversation with spouse/partner about retirement vision, time together, and boundaries.
- Identify your top relationships and assess where you want to invest time; start repairing important relationships now.
- Plan for the loss of workplace social life: list the communities you want to join and how you’ll make new friends.
- Clarify expectations around family support (adult children, grandchildren, financial help) early to prevent conflict.
- Inventory key documents and accounts; create a “where everything is” guide and ensure someone else knows.
- Start simplifying financial life: consolidate accounts where appropriate and close unused credit/loose ends.
- Review estate planning status: will/trust, executor/successor trustee, and whether anything is outdated.
- Begin a digital estate plan: password management, online banking, social media, key access instructions.
Testing & Refining
- Convert your vision into a weekly structure (anchors like exercise, volunteering, social activities, learning blocks).
- Schedule 2–3 “trial runs”: take longer time off blocks to experience weekdays without work structure.
- Confirm 1–2 meaningful roles (board/mentoring, coaching, part-time advisory, or volunteer leadership) that replace “work identity.”
- Plan for the “first 6 months” risk: boredom, loss of social environment, and drifting.
- Choose your retiree health insurance path (bridge coverage if under 65; Medicare approach if near 65).
- Evaluate “healthy aging” and mobility risks; decide on home modifications or future housing alternatives (aging in place vs. move).
- Create a medical advocacy plan: who speaks for you if needed + confirm primary care aligned with senior-focused needs.
- Begin Long-Term Care planning: whether you’ll self-fund or insure; outline triggers for care decisions.
- If staying: plan and schedule aging-in-place modifications (stairs, grab bars, layout changes).
- If moving: visit a few potential locations and research property taxes, climate preferences, and community type (55+ vs. mixed, closer to family, etc.).
- Build a trusted list of providers (home maintenance, repairs, help services) so support is ready when needed.
- Consider a “test move” approach: rent for a period before buying in a new location.
- Build/expand a retired-peer network: meetups, clubs, volunteering, faith/community groups, hobby circles.
- Decide how you’ll divide time and space at home (especially if both partners retire).
- Create a plan to stay connected with distant family (standing calls, trips, shared traditions).
- If you anticipate caregiving (parents, spouse, “sandwich generation”), outline resources, support and boundaries.
- Update will/trust and confirm durable power of attorney and healthcare directives (at least drafts).
- Review and update beneficiaries across retirement accounts and life insurance.
- Define legacy intentions: inheritance goals, charitable plans, donor-advised fund/foundation exploration.
- Prepare your executor/successor trustee: share document locations and key contacts.
The Home Stretch
- Finalize a retirement calendar for the first 3–6 months (structure + flexibility) to avoid the “cold turkey” whiplash.
- Lock in recurring commitments (classes, volunteer shifts, travel blocks, fitness schedule) and pre-enroll where possible.
- Set boundaries and expectations with family/friends about availability so retirement doesn’t become “default helper.”
- Identify one “legacy impact” project (mentoring, community, writing, teaching) and outline your first steps.
- Finalize Medicare decisions (timing + whether Medigap is needed) and budget for dental/vision/hearing.
- Complete any elective procedures while still covered by employer insurance.
- Complete advanced healthcare directives and clarify end-of-life preferences (interventions, care wishes).
- Lock in your “retirement wellness schedule” (weekly exercise, cognitive engagement, social connection targets).
- Finalize the move/stay plan and timeline; if moving, align it with retirement date and healthcare coverage.
- If downsizing: complete sorting and sell/donate phases; reduce storage and simplify possessions.
- Lock in your “community plan” (clubs, groups, volunteering) to build a social circle if relocating.
- Align with your partner on shared and individual retirement plans.
- Put weekly social commitments on the calendar (standing lunches, volunteering, clubs, exercise groups).
- Confirm boundaries: how often family visits, how much grandparenting you want, and your “off-limits” time.
- If pets are part of the plan, set routines and future care arrangements.
- Finalize advanced directives and end-of-life wishes; share with key people and physicians.
- Complete the “in case something happens” packet: documents, contacts, account list, instructions.
- Hold a family conversation (as appropriate) to reduce future conflict and clarify intentions.
- Confirm charitable and legacy actions are implementable (beneficiary designations, giving plan, successor roles).
For a more detailed approach, we've created a Retirement Prep Questionnaire to help you review all the things you need to consider before retirement. Access it below!
Be sure to check out our Retirement Activities for books on retirement prep, “bucket list” inspiration, and everyday travel and fun
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