How many times have you looked at your calendar and thought, “Is retirement closer than I think?” It sneaks up. One day you’re helping someone set up a 401(k), and the next you’re wondering if yours is enough. As people live longer and costs keep rising, retiring well takes more than wishful thinking and vague plans.
In this blog, we will share practical, timely moves to make before stepping away from full-time work.
Get Clear About What You’ll Actually Need
It’s easy to throw out round numbers when talking about retirement—$1 million here, a “comfortable cushion” there—but clarity is more useful than guesswork. A sustainable plan starts with understanding your lifestyle goals and then mapping them against real-world costs.
That includes the obvious things like housing, food, and medical expenses, but also the less glamorous parts: car repairs, unexpected dental work, inflation, and rising insurance premiums. Many retirees are finding that what used to feel like extra padding now barely keeps pace with the reality of modern life.
Social Security alone won’t cut it for most. Pensions are less common. Healthcare continues to outpace most cost-of-living adjustments. In this environment, your future income needs to come from well-structured sources—personal savings, investment income, and in many cases, passive earnings or part-time work.
Before you make any moves, it helps to run real projections. Not just an app on your phone, but an in-depth look with a financial planner who can stress test your plan against market swings, tax shifts, and potential life changes.
And if any of your assets are outside the U.S., or if you’ve spent years working abroad, it’s important to know what is FBAR and FATCA compliance because these reporting requirements apply to foreign accounts and financial interests, and ignoring them can lead to steep penalties—even if the oversight was unintentional. Understanding the rules now gives you time to report properly, avoid unnecessary risk, and fold international accounts into your broader retirement plan.
Understanding the reporting rules before you retire helps you avoid costly missteps. With transparency and good records, these requirements are easy to manage, and they can be folded into your broader tax strategy with very little friction. In the long run, proactive compliance supports better planning and avoids the stress of audits or late corrections, especially as you shift into a fixed-income mindset.
Cut Loose the Debt That Doesn’t Serve You
Debt in retirement is like a leaky faucet—silent at first, then suddenly draining everything. Some forms of debt are manageable, like low-interest mortgages on appreciating assets. Others, like high-interest credit cards or personal loans, can chew through your budget fast.
The smartest move before retirement isn’t to wipe out all debt blindly, but to review what you owe and decide what’s worth keeping. Look at interest rates. Look at loan terms. If something’s stretching your monthly obligations without delivering real value, it’s probably better to clear it before stepping away from your primary income stream.
Consider downsizing if housing costs are out of proportion with your post-retirement budget. A smaller home can free up equity, reduce utility bills, and lower your insurance burden. Even if you love where you live, re-evaluating property expenses as you age is just smart math.
Know What You’ll Really Need to Retire Well
Before retirement, vague targets don’t help much. A real plan comes from knowing your costs, your income sources, and how long both can hold up. Start by breaking down what you’ll actually spend—housing, healthcare, taxes, and the routine expenses that never stop. Then compare those numbers against your savings, pensions, and any future income you can count on.
For professionals in the energy sector, this step carries extra weight. Oil and gas retirement plans often combine 401(k)s with high employer matches, deferred compensation, and pension choices that can shift with market conditions. These benefits can build strong financial footing, but only if they’re coordinated the right way. Treat each piece—lump-sum options, stock plans, and annuities—as parts of one system rather than separate accounts.
A smart move before retiring is to test how these benefits perform under different conditions. A pension might look stable now, but interest rate changes or inflation can alter its value over time. Likewise, 401(k) and stock distributions can trigger higher taxes if not timed right. Running projections with a planner who understands energy-sector benefits helps you see what your income will look like in practice, not just on paper.
Another advantage of early planning is flexibility. Many oil and gas plans allow in-service rollovers or after-tax contributions that can turn into tax-free growth later. Taking advantage of those options before you retire can make a long-term difference once your paycheck ends.
Clarity about what you own, what you’ll earn, and how each account fits together turns guesswork into structure. That’s what separates a comfortable retirement from a costly adjustment period.
Also, be realistic about your ability to borrow in the future. Without a steady paycheck, access to credit becomes more limited. Lenders often view retirees through a tighter lens, even if they’re sitting on solid assets. Eliminating unnecessary liabilities now gives you more control later.
Don’t Wait to Tackle Healthcare
The healthcare elephant never leaves the room, and it’s only getting bigger. Even with Medicare, out-of-pocket costs continue to rise, and many pre-retirees underestimate just how much of their budget will go to staying well.
Before retirement, it’s worth pricing out Medicare supplement plans, long-term care insurance, and potential out-of-pocket costs for dental, vision, and hearing. These areas often fall outside traditional Medicare coverage and can add up fast.
If you hold a health savings account, this is an ideal moment to contribute as much as you’re allowed. Unlike flexible spending accounts, the balance carries over from year to year and remains available even after retirement. HSAs also provide a powerful threefold tax advantage: money you put in reduces your taxable income, growth inside the account is untaxed, and withdrawals for eligible medical costs stay tax-free.
Even if you’ve always been healthy, healthcare costs in retirement are one of the top reasons people dip into their principal faster than planned. Planning now gives you more options later, especially if your health shifts unexpectedly.
Review Your Taxes Like a Business Owner Would
When you stop working, you don’t stop paying taxes. But the structure changes. Instead of W-2s and automatic withholding, you’ll likely be drawing from various sources—Social Security, IRAs, brokerage accounts, maybe even rental income. Each of these comes with its own tax treatment, and if you’re not careful, you could end up paying more than necessary.
Now is the time to review your withdrawal strategy. In what order will you pull from your accounts? Do you need to take advantage of Roth conversions while you’re in a lower tax bracket? Would a donor-advised fund or charitable contribution reduce your taxable burden while supporting causes you care about?
These are questions best answered with a CPA or financial advisor—not after you’ve already made withdrawals, but before. Smart retirees don’t just minimize taxes in one year—they create multi-year strategies that help preserve capital and reduce surprises.
Update the Paperwork You Forgot About
Retirement has a way of making things real. That means the paperwork you haven’t looked at in years needs a fresh review. Wills. Powers of attorney. Beneficiary designations. All of these matter more when you’re no longer working full-time.
Check that your estate plan reflects your current wishes. Make sure your healthcare directives are up to date. Verify that all accounts have named beneficiaries and that those names match your current relationships. A mismatch here doesn’t just cause confusion—it can lead to legal problems for your family later.
If your finances are complex, consider working with an estate planning attorney who can tie everything together. Don’t wait until something happens. The most effective plans are the ones nobody has to scramble to find.
Retirement doesn’t begin with a party or a countdown clock—it begins with quiet decisions made in the years leading up to it. The better those decisions are, the less your future self will have to worry about. A smart retirement isn’t about having more—it’s about needing less from the systems around you, because you’ve already thought ahead.
