Can I retire now? And what do I need to decide before my deadline?
Your retirement date, benefits, and withdrawals affect one another. Some choices can't be undone.
Get a written plan for these decisions before you commit to any of them.
Talk About Your Retirement DecisionSound familiar?
- You're within a few years of retiring, or you just did
- Your employer is offering a separation package or early retirement offer
- You're selling a business or stepping away from one
- A life change, like a spouse's retirement or an inheritance, has moved up your timeline
The decisions, and what's behind each one
Can I afford to retire now?
Your plan compares retirement dates using your spending, income, and savings, then tests lower returns and higher spending.
Would working one more year make a real difference?
Another year adds savings and reduces withdrawals while potentially increasing benefits. Your plan shows whether the difference is worth your time.
How much can I spend?
Your plan sets a spending level your savings can support in strong and weak markets.
What if the market drops right after I retire?
Early losses hurt more when you're withdrawing money. Your plan tests a major decline and shows how holding cash and bonds for near-term spending reduces the need to sell stocks in a downturn.
Should I accept my company's separation package?
Compare the offer's taxes, health coverage, retirement benefits, and the alternative of continuing to work.
What should I do with my 401(k)?
Compare leaving it in place, an IRA rollover, or a new employer's plan. Consider fees, investments, early-withdrawal access, and company-stock tax options before moving it.
Which accounts should fund my first years of retirement?
Your plan sequences withdrawals from taxable, IRA, and Roth accounts to help reduce lifetime taxes.
Should I make Roth conversions?
Lower-income years before Social Security and required withdrawals may favor conversions. Your plan weighs future tax savings against today's taxes and potential Medicare premium increases.
How will retirement change my taxes?
Your plan projects taxes on withdrawals and benefits year by year. Oklahoma excludes Social Security and some retirement income from state tax.
When should I claim Social Security?
Your plan compares claiming ages from 62 to 70 for both spouses. Delaying the higher earner's benefit can also increase the survivor's income.
How does Medicare affect my timing?
Medicare eligibility starts at 65; earlier retirement requires other coverage. Your plan identifies enrollment dates and whether employer coverage allows a delay without penalties.
What happens financially if one of us dies first?
The survivor generally keeps the larger Social Security check but may face higher taxes. Your plan tests their income alongside pension and beneficiary choices.
What comparing retirement dates looks like
See each date's savings, withdrawals, health coverage costs, and sustainable spending side by side.
The comparison uses your numbers and tests an early market decline.
If you're facing a deadline
Tell Kevin about your deadline before you sign up. Documents are normally due within seven days, but if you send them within five business days of signing, Kevin will address that decision first. He can't guarantee completion before a deadline someone else sets.
He can't guarantee completion before a deadline someone else sets.
How the Financial Planning service works for a retirement decision
Focus on the choices that shape retirement:
- Retirement dates compared: spending and market risks for each
- Withdrawal and Roth conversion choices coordinated with taxes
- Social Security and Medicare timing for both spouses
- 401(k), pension, and separation offers evaluated before you decide
You decide which recommendations to carry out.
Questions about retirement planning
The information on this page is general and isn't advice for your specific situation. Tax and benefit rules change, and your plan reflects the rules in effect when it's written.
Who you'll work with
Kevin Jacobs, CFP®, leads every planning meeting with taxes in view.
Talk About Your Retirement Decision30 minutes, by phone or video. No fee, no obligation, and nothing to prepare.