If you’re approaching retirement (or already there and still thinking it’s “far enough away”), you’ll want to pause and ask honestly: Are you really ready? I mean more than just hoping your 401(k) will be enough. Retirement-readiness means having a plan that coordinates your investments, taxes, estate, legacy, income strategy – and yes, your “what happens if things don’t go as planned” strategy. You can’t afford to wait.
Here are some key questions you should be able to answer now:
- Do you have a written financial plan that coordinates your investments, taxes, estate, and legacy goals?
- Is your portfolio diversified beyond stocks and bonds, such as alternatives, private markets or real assets?
- Is your portfolio intentionally structured to balance risk, provide access to liquidity, and minimize taxes?
- Do you have an income strategy that intentionally coordinates investment withdrawals, Social Security timing, and tax brackets throughout retirement?
If you hesitated even one time reading any of those – then you’re not just “slightly behind,” you’re probably in a spot that needs immediate attention.
Why you can’t afford to wait
When you delay serious planning you invite risks – some obvious, some hidden. For example: inflation erodes your purchasing power, health‐care costs climb, market swings can derail your investment portfolio, tax changes surprise you, and longevity means you may live far longer than you expect. An appropriate quote from financial planning firm Fragasso Financial Advisors writes that “the longer you live, the more you need to be prepared.” 1
Also: many people keep treating retirement as a single event (“I’ll retire at 65 and I’ll be done”) instead of a multi‐phase financial journey. A measured income strategy, tax management approach, investment plan and estate plan all matter. If you wait until “just before retirement” to pull these together – you’re exposing yourself.
Pre-Retire-Better: Steps to Guide You Toward Retirement Readiness
Here are actionable steps you should implement to move from “hopeful” to “prepared.”
- Create or update your written comprehensive financial plan.
This means you have a document that ties together your goals (when you want to retire, how you want to live, legacy you care about), your investments, your tax strategy, your estate plan, and your withdrawal strategy. If you don’t have it, get one. If yours is more than 2–3 years old, revisit it. Many people rely only on investment plans – not the full coordination of taxes, estate, legacy needs. - Diversify your portfolio beyond just stocks and bonds.
Do you truly understand the makeup of your investment portfolio? The question: Do you have access to alternatives, private markets, real assets? These asset classes may help with inflation, risk diversification, liquidity scheduling, and tax efficiency. If your investments are all traditional equities/bonds you may be missing important levers. - Structure your portfolio intentionally for risk, liquidity and taxes.
In retirement, you may need liquidity for health surprises or living changes. You may face tax-bracket issues when selling real estate, taking Social Security or RMDs (required minimum distributions). Your investment holdings should reflect these realities, not just “buy and hold” stock indices. - Develop a coordinated income-strategy for retirement.
This means: you’ve thought about when and how you’ll start taking Social Security, how you’ll withdraw from accounts (taxable, tax-deferred, tax-free), how you’ll manage tax brackets each year, how you’ll adjust if markets suck or longevity surprises you. Without this you run big risks: paying too much tax, running out of money, making forced poor decisions. It’s important to seek coordinated advice from your tax professional and financial advisor. - Consider your employer‐sponsored retirement plans carefully.
If you have a 401(k), 403(b), pension, cash-balance, or any company plan – this is a major piece of retirement readiness. Decide how much you’re contributing now, whether you’re maximizing the match, whether the plan’s investment lineup and fees make sense, whether you’ll roll it or keep it once you leave. Many people assume “it’s handled” because “I contribute to my 401(k).” But they don’t check fund fees, asset allocation, tax implications, or integration with their other accounts. - Review stated retirement expenses and adjust for reality.
What will your spending be in retirement? Many assume “less” but ignore hidden costs: health care, long‐term care, inflation, travel, taxes. Plan for those. If you don’t, you’ll enter retirement surprised and under-prepared. - Revisit your estate and legacy plan.
Retirement readiness isn’t just about you; often it’s about what you leave behind. Do you have wills, trusts, beneficiary designations, tax-efficient legacy structures? Are you coordinating your charitable intent, family gifting, business succession (if relevant)? Without this coordination you may have more taxes, more legal hassle, or poor outcomes for heirs. - Stress test your plan for “what if” scenarios.
What if markets are flat for 10 years? What if you live to 95? What if you experience a health event and personal care is needed? What if you withdraw more because you retire earlier than planned? A robust retirement readiness plan tests various scenarios, so you’re not caught off guard.
What happens if you get it wrong?
If you skip any of these areas, risks pile up. You might:
- Face higher than expected taxes because you didn’t coordinate withdrawals and Social Security.2
- Run out of money in your 70s or 80s because sequence risk stripped your portfolio early.
- Be forced to sell illiquid assets at bad times or take withdrawals from the wrong accounts leading to tax inefficiency.
- Have to reduce your lifestyle instead of maintaining it, because you didn’t budget for inflation, healthcare, or long retirement.
- Leave your estate exposed to heavy taxation, or cause family friction, because you didn’t plan legacy and exit properly.
In short: waiting or assuming “I’ll do it later” often means you end up doing something but not a coordinated whole. That gap may cost a lot of years of regret.
A real-world check
Remember those questions at the top? If you answered “no” or “not sure” to any of them, set a priority. For example: if you don’t have a written plan coordinating everything – start there. If you don’t have an income strategy – start building that. Educate yourself on your retirement plan (401k/403b) contribution limits as these limits tend to increase the closer you get to retirement age.
The firm Fragasso Financial Advisors created a quick retirement readiness quiz – a short tool that prompts you to think about readiness from multiple angles. This tool incorporates the multi-angle retirement readiness approach discussed in this article.
Final word
Step into your retirement years with intention, structure and contingency. You want to align your investments, taxes, estate and income strategies in one unified plan with the guidance of your financial planner, accountant and estate attorney. You want flexibility, diversity, tax-efficiency and clarity. Your future self and your heirs will thank you.
If you’re asking “am I maximizing my wealth?” and you don’t have confident answers for each of those key questions, take one step today: pick one of the areas above and make it your focus. Because real retirement readiness happens when you stop hoping and start preparing.
- https://www.fragassoadvisors.com/individuals/high-net-worth-business-owners-executives/
- https://www.kiplinger.com/retirement/retirement-planning/true-measure-of-retirement-readiness-isnt-the-size-of-your-nest-egg
Investment advice offered by investment advisor representatives through Fragasso Financial Advisors, a registered investment advisor.
