Retirement may still feel comfortably distant when you are six years away, but the decisions you make during these final working years can have a lasting impact on both your financial security and the lifestyle you eventually enjoy. This is a valuable window of time because you may still have steady employment income, time to make adjustments, and enough flexibility to test some of the assumptions you have about retirement before they become permanent decisions.
Here are six areas worth considering as you prepare for the transition.
1 – Test-Drive Your Retirement Destination
It is easy to imagine retiring somewhere warm, scenic, or completely different from where you spent your working years, but vacationing somewhere for a week and actually living there can be very different experiences.
Before buying a home or committing to a permanent move, consider renting in the area for several weeks or even a few months. If Florida is the dream, experience some of the summer heat. If you are considering another state, spend enough time there to understand the community, transportation, healthcare, daily expenses, and whether the lifestyle actually feels right once the novelty wears off.
The same planning mindset applies to travel. Instead of treating the places on your bucket list as vague someday goals, begin identifying where you want to go and what those experiences may cost. Jordan is personally passionate about using credit card rewards and travel points strategically, and viewers interested in his approach can comment “travel” on the YouTube video linked below to request his free travel guide.
2 – Get Ahead of Major Home Repairs
The final working years can also be a useful time to evaluate your home and identify large expenses that may be coming.
A roof, HVAC system, windows, kitchen renovation, or other major project may be easier to handle while employment income is still coming in rather than after you begin relying primarily on retirement income. Waiting until something fails can also reduce your flexibility because an emergency repair gives you less time to compare contractors, pricing, and alternatives.
This does not mean rushing into every renovation on your wish list. Instead, take inventory of the projects that are likely to become necessary, gather multiple estimates, and decide which expenses make sense to address before retirement.
3 – Build a Life Outside of Work
Retirement planning often focuses heavily on money, while overlooking the enormous lifestyle transition that comes from leaving a career.
After working for 20, 30, or 40 years, your job may provide far more than a paycheck. It can provide structure, relationships, a sense of purpose, and something productive to do each day. Removing all of that at once can be a difficult adjustment, even for someone who is financially prepared to retire.
This is why the years before retirement are a great time to explore volunteering, hobbies, mentoring, consulting, part-time work, community involvement, or other activities that provide fulfillment. You do not need your entire retirement calendar figured out six years in advance, but beginning to build a social network and sense of purpose outside of work can make the transition much smoother.
4 – Prepare for Healthcare Costs
Healthcare should be a meaningful part of any retirement budget. Fidelity’s 2026 Retiree Health Care Cost Estimate projects that a 65-year-old retiring in 2026 could spend an average of approximately $185,500 on healthcare and medical expenses throughout retirement, and that estimate does not include potential long-term care expenses (Fidelity).
That makes the years before retirement an important time to understand your future Medicare coverage, expected out-of-pocket costs, and whether an HSA may fit into your strategy. For 2026, eligible individuals can contribute up to $4,400 to an HSA with self-only coverage or $8,750 with family coverage, subject to the applicable eligibility requirements (IRS).
The goal is not to predict every medical bill decades in advance. It is to make sure healthcare is included in your financial plan so that rising expenses do not become a surprise later.
5 – Develop a Social Security Strategy
Choosing when to claim Social Security should be part of the broader retirement income conversation rather than an automatic decision based on a particular birthday.
Retirement benefits can generally begin as early as age 62, although claiming before full retirement age results in a permanently reduced monthly benefit. Delaying beyond full retirement age increases the monthly benefit until age 70, when delayed retirement credits stop accumulating (Social Security Administration).
The highest possible monthly check is not necessarily the right objective for every household. Your health, family longevity, other income sources, taxes, spouse or survivor benefits, and overall financial needs should all be considered when deciding when to claim.
6 – Make Sure Your Financial Plan Looks at the Whole Picture
Investments are important, but retirement involves much more than investment performance.
A comprehensive retirement strategy may include income planning, tax planning, healthcare, Social Security, legacy planning, cash flow, insurance, and the lifestyle decisions that determine how much money you actually need.
As retirement approaches, consider whether the person helping with your finances is looking at those pieces together or simply managing an investment portfolio. The objective should be to create clarity around how your assets support the life you want to live, while helping you prepare for the risks and decisions that may arise along the way.
Six years gives you time. The opportunity is to use that time intentionally.
To hear more on this topic, watch the full video here!
