July 21st, 2026 | 12:00 PM MST Written By: Teresa Milner | Senior Wealth Management Advisor with Pearl Capital Management
A few days after returning home from vacation, I found myself scrolling through the family photos we took on the beach in Oceanside. Twenty smiling faces. Three generations. One unforgettable week together. Looking at the photos reminded me of just how grateful I am that my children made bringing our family together a priority.
As I smiled and looked through the photos, I realized they represented much more than a vacation. They represented months of planning that no one saw.
That experience reminded me of something I see every day as a financial advisor, or as I like to think of my role, a financial thinking partner.
The most fulfilling retirements rarely happen by accident. Just as our vacation required planning before anyone packed a suitcase, retirement requires planning long before you stop working.
Why the Last 5–10 Years Matter Most
Throughout life, there are many seasons when retirement planning is important. While it’s never too early to begin planning, the five to ten years before retirement often become the most important years for making the decisions that shape the decades ahead.
This is the time when many of the biggest financial decisions are made. Those decisions can affect your income, taxes, healthcare, investments, and lifestyle for decades to come.
Many people spend more time planning a two-week family vacation than they spend planning a retirement that could last 30 years.
Just Like Planning a Vacation…
Watching my grandchildren run into the waves, I wasn’t thinking about airline reservations or condo bookings. I was simply present. That’s the gift thoughtful planning gives us. It allows us to be fully present instead of worrying if we forgot something.
Before anyone could enjoy the beach vacation, someone had to answer some important questions. Where are we going? When should we travel? How will everyone get there? Where will we stay? What experiences do we want to have together?
Retirement planning asks similar questions. Where do you want retirement to take you? When is the right time to retire? Will your income support the lifestyle you envision? How will you pay for healthcare? How can you reduce unnecessary taxes? Will your investments continue to support you after your paycheck stops?
The trip reminded me that our family’s greatest priority isn’t the destination itself, but it’s spending meaningful time together. Every planning decision flowed from that shared value.
Whether you are planning a family vacation or planning for retirement, the biggest decisions deserve more than last-minute attention.
Five Things to Focus on During the Last 5–10 Years
If there are only 5-10 years left on the clock until retirement, this is an ideal time to review your retirement plan to make sure you’re on track for the retirement you’ve envisioned. Consider focusing on these key areas:
1. Imagine your ideal Tuesday.
The best retirement plans aren’t built around numbers. They are built around values. The numbers simply support the life you want to live. Imagine waking up on a Tuesday with nowhere you have to be. Where are you? Who are you spending time with? What brings purpose and joy to your day? Travel? Family? Volunteering? A part-time career? Without understanding what matters to you, it’s impossible to build a meaningful roadmap. I find it helpful to start with your ultimate destination, the life you hope to create, and then work backward to determine the decisions that help make that vision possible.
2. Know where your paycheck will come from.
Understanding your income sources helps determine how much you can confidently spend in retirement. Social Security, pensions, retirement accounts, and investments all play a role in creating dependable income.
3. Think about what your tax situation will be in retirement.
Managing your tax liability in retirement could potentially allow you to hold on to more of your hard-earned savings. The way you withdraw retirement assets can significantly affect how much you keep after taxes.
4. Prepare for healthcare costs.
Long-term care costs could quickly eat into your retirement savings, so this could be a good time to assess your personal risk. Healthcare is one of the largest expenses retirees face. Planning ahead can reduce surprises.
5. Review your investment strategy.
As retirement approaches, your investment portfolio should reflect your changing goals and risk tolerance. The strategy that helped you grow your assets during your working years may not be the same strategy that’s best for generating income throughout retirement.
Planning Creates Confidence
Confidence doesn’t come from having the biggest retirement account. It comes from knowing your financial decisions support the life that is most important to you.
One of the things I appreciated most about our family vacation was that I never worried about the logistics.
Someone had already thought through the details.
That is exactly what a well-designed retirement plan should do.
It doesn’t eliminate every surprise. Life will always present unexpected challenges. But thoughtful planning creates confidence. It allows you to spend less time worrying about finances and more time enjoying the retirement you have worked so hard to achieve.
The family photos we took on the beach now remind me of more than a wonderful vacation. They remind me that meaningful experiences don’t simply happen. They are built through thoughtful planning.
Retirement is no different.
The destination certainly matters. But whether you are planning a family vacation or planning for retirement, it’s the thoughtful decisions you make long before you arrive that allow you to be fully present and truly enjoy the journey.
Let’s Talk
If you’re walking through this season, or know it’s on the horizon, it helps to have a thoughtful plan. At Pearl Capital Management , we help families navigate the emotional and financial transitions of retirement, so they can move forward with clarity and peace of mind. We would be honored to walk this journey with you. Please send us an email at email@thepearlcapital.com or give our office a call at (602) 718-1177.
