Retirement is no longer a far-off dream—it’s on your doorstep. If you’re in your 50s or early 60s, now is the time to get serious about preparing for life after work. Whether you plan to retire early, work part-time, or just want to travel more, your decisions now can make or break the quality of your ‘golden years.’

The pre-retiree years should be like when a submarine’s crew scrambles to seal, or ‘batten down’, the hatches to keep the water out as they submerge. If even one of those hatches isn’t sealed, there is no seal and to the bottom that submarine will go. This can also be true with our retirement plans.

I remember working with a client years ago that came in six months out from retiring and hadn’t done much of anything in retirement planning. They were on the precipice of taking their last paycheck and didn’t really know where they stood. One of the other advisors said after that that wasn’t financial planning as much as it was damage control.

The good news? Whether planning or damage control, it’s not too late. Here’s a comprehensive guide to financial planning for pre-retirees—designed to help you move into retirement with confidence, security, and peace of mind.

1. Clarify Your Retirement Vision

Before diving into the numbers, ask yourself:

• When do I want to retire?
• Where do I want to live?
• What kind of lifestyle do I want?
• Will I work part-time or pursue passion projects?

Your vision will guide your financial decisions—from savings goals to investment strategies.

NOTE: If you take nothing else from this article, remember this. In my experience, some of the worst retirements are the ones where they are just allowed to happen. A question that everyone should answer for themselves is “To what am I retiring?” Too many people simply stop working. That’s it, never asking what comes after. Sometimes a person’s spouse becomes their retirement plan. Sometimes it might be playing golf. Other times it could be traveling. The bottom line is that too often, these things dry up and people can become bored and disillusioned. If you think this is something you might struggle with, plan for it now.

2. Get a Clear Picture of Your Current Finances

Start by assessing your financial health:

• Net worth (assets minus liabilities)
• Retirement accounts (401(k), IRA, pensions)
• Non-retirement assets (savings, home equity, investments)
• Debts (mortgage, credit cards, loans)

Knowing where you stand helps identify any gaps in your plan.

3. Estimate Your Retirement Expenses

Your costs in retirement may shift—no more commuting or work attire, but possibly higher
healthcare expenses or more travel. Remember, just about every time you leave the house in
retirement will cost you money.

Break down your projected expenses into categories:

• Essentials: Housing, food, insurance, healthcare
• Lifestyle: Travel, hobbies, entertainment
• Unexpected: Home repairs, medical emergencies, family support

A good rule of thumb: You’ll need 70–85% of your pre-retirement income annually

4. Maximize Retirement Contributions

This is your final push—supercharge your savings with catch-up contributions:

• 401(k): Up to $31,000 if you’re 50+ (2025 limits)
• IRA/Roth IRA: Up to $8,000 if you’re 50+
• HSAs: Great for healthcare expenses—triple tax benefit. This is one that many use
  incorrectly. Let’s talk if you have this invested in cash-only. You’re missing one of the
  most powerful aspects of this account.

If you’re behind, consider reducing expenses and allocating bonuses or side income to savings.

5. Review Your Investment Strategy

As retirement nears, shift from aggressive growth to a more balanced, risk-aware portfolio:

• Rebalance regularly
• Diversify across stocks, bonds, and cash
• Consider annuities or guaranteed income options
• Align your investments with your retirement timeline and risk tolerance

A financial advisor can help you tailor your strategy for this new stage. We do this on a regular basis with our clients, making sure that their strategy lines up with their values, needs, goals and risk tolerances. Autopilot isn’t really a strategy.

6. Plan for Social Security

Your claiming strategy can significantly impact your lifetime benefits:

• You can claim as early as 62, but benefits increase the longer you wait (up to age 70)
• Delaying can boost your monthly payout by up to 8% per year

Use the SSA’’s’s calculator or consult a planner to time it right for your needs.

7. Create a Withdrawal Strategy

Once you retire, the question becomes: How do I live off what I’ve saved?

• Consider the 4% rule as a general guideline (or 2.4% if you want to be more conservative)
• Plan which accounts to tap into first (e.g., taxable, tax-deferred, Roth)
• Minimize taxes with smart withdrawal sequencing
• Don’t forget Required Minimum Distributions (RMDs) starting at age 73

Having a withdrawal plan can help you stretch your nest egg without fear of running out. Too many people give little thought to how and when they will access the money they have been saving for this time in life doing irreparable harm to their overall chance of success.

8. Protect Yourself and Your Family

• Review insurance needs (long-term care, life, health, home)
• Create or update your will and estate plan
• Assign a power of attorney and healthcare proxy
• Organize important documents and communicate your wishes

Planning ahead protects your loved ones and avoids confusion during difficult times. Estate planning is often the caboose that brings up the rear in financial planning. But it really should be one of those things that people tackle sooner rather than later. We never know what might be around the corner and so having things in place for our loved ones is a very good idea. Too many times I have seen children in crisis mode trying to figure out what to do next when a parent passes away. With some simple planning, you can take this stress off the table for your loved ones during a very emotional time.

9. Test Drive Your Retirement

Take your retirement plan for a spin:

• Try living on your projected retirement budget
• Take a sabbatical or extended break
• Experiment with how you’ll spend your time

This gives you a real sense of whether your plan is realistic—or needs adjustments.

10. Work with a Financial Planner

A professional can help with:

• Optimizing your investments
• Creating a personalized withdrawal plan
• Navigating tax strategies
• Ensuring nothing critical is overlooked – Warren Buffet used to say that we’re never hit by the bus we’re looking at. It’s my job to watch for those buses.

Look for a fiduciary advisor who puts your best interest first.

Conclusion: Step into Retirement with Confidence and Contentment

Retirement isn’t a single moment—it’s a transition that requires thoughtful planning. The steps you take in the next few years can make a big difference in the quality of your post-work life.

So take charge now: visualize your future, fine-tune your savings, and prepare with purpose. Peace of mind in retirement starts with smart planning today