Your sixties are the most consequential financial decade of your life. Retirement dates, pension claims, healthcare costs and housing decisions all converge, and many of the choices are difficult or impossible to reverse. Financial planners say five moves, made deliberately rather than by default, can shape how secure and flexible the following thirty years turn out to be. None requires wealth or exotic investments; all reward attention while options are still open.
1. Time your retirement income claims
When you claim Social Security, or your state pension, shapes your income for life. Claiming at the earliest opportunity locks in a permanently reduced benefit, while delaying can raise it substantially, so the right answer depends on health, work plans and how a couple coordinates their claims. One powerful middle path is for one partner to delay while the other claims earlier. Run several scenarios rather than defaulting to the earliest date; the Social Security Administration provides calculators that make these trade-offs concrete, and a single meeting with an adviser can repay itself many times over at this step.
2. Build a tax-aware withdrawal order
Retirement income usually comes from several pots — taxable accounts, tax-deferred pensions and savings, and tax-free accounts where they exist — and the order in which you draw from them affects how much tax you pay every year for decades. Spreading withdrawals deliberately, filling lower tax brackets in early retirement years before required distributions begin, and considering partial conversions in low-income years can all reduce lifetime tax. The Consumer Financial Protection Bureau offers plain-language guides to retirement income decisions that can help households map this sequencing before the first withdrawal is made.
3. Plan for healthcare before it plans for you
Healthcare is the expense retirees most consistently underestimate. Your sixties are the moment to understand exactly when public coverage begins, what it excludes, and what supplementary insurance or savings should bridge — including dental, vision, hearing and the possibility of long-term care, which can dwarf every other retirement cost. If you retire before coverage starts, price the gap explicitly rather than discovering it later. Staying insurable, funding a health savings account while eligible, and keeping an emergency reserve sized for medical shocks all belong in the same conversation as investment returns.
4. Right-size housing and debt
Entering retirement with a large mortgage or high-interest debt constrains every other decision. Your sixties are a natural point to decide whether your home still fits your life: downsizing can release equity, cut maintenance and future-proof mobility, while staying put may argue for paying the mortgage down or adapting the property. Equally, review insurance you may no longer need — and protection you may be missing — with fresh eyes.
Keep some flexibility in reserve
Threaded through all five moves is a sixth, quieter principle: preserve options. The sixties bring surprises in both directions — redundancy or an unexpected inheritance, illness or a new business idea, grandchildren nearby or a long-imagined relocation. Households that keep a cash buffer, avoid locking every asset into irreversible products, and review their plan annually can absorb those turns without dismantling it. Flexibility is also psychological: people who treat their plan as a living document, revisited after each major life event, report more confidence about retirement than those who set a course once and dread checking whether it still points the right way.
5. Put the paperwork in order
Finally, the unglamorous essentials. Update wills and beneficiary designations, remembering that designations on accounts often override wills. Establish powers of attorney and healthcare directives while there is no urgency, consolidate scattered accounts, and make a simple map of assets, policies and advisers for a trusted person. Your sixties reward the organised: five deliberate moves — timing claims, sequencing withdrawals, funding healthcare, right-sizing housing and debt, and ordering your affairs — can protect decades of income, health and independence. More money guidance appears in our finance pages and at Newsletter Issues.
