Is it Time for an Annual Planning Retreat?

Do you ever feel like you never truly get a moment to yourself? Or that when you do, it doesn’t feel as meaningful or productive as it could be?

In today’s always-on culture, the constant pressure to stay busy can paradoxically keep us from making real progress. We hustle through our daily routines, checking off tasks, yet often lose sight of our long-term goals. Without proper time for reflection, we risk drifting rather than intentionally directing our lives.

That’s where a planning retreat comes in.

By taking a step back to reflect on your past year—what worked, what didn’t, and where you’re headed—you can begin making deliberate choices about your future. That includes big-picture decisions, like estate planning, that align with your values not just today but for years to come.

What Is a Planning Retreat?

You’ve probably heard of a wellness retreat, which is a chance to recharge, reflect, and reconnect with yourself. A planning retreat shares that same spirit of stepping away from everyday demands but with a future-focused lens.

While wellness retreats tend to prioritize rest and well-being in the present, planning retreats are designed to help you gain clarity about your personal, professional, and financial goals. Both are rising in popularity as more people seek meaningful ways to escape burnout in a hyperconnected world.

A personal planning retreat can be a game changer. When you step away from your usual routine to think strategically and set clear intentions, you return with renewed purpose and a realistic roadmap to get where you want to go. With a solid plan in place, feelings of stress and uncertainty tend to ease, leaving space for confidence and progress.

How Does a Planning Retreat Work?

There’s no rigid formula to follow. What matters most is carving out intentional time to reflect on the past year and plan ahead. Think of it as your own personal “company retreat.” If you have a romantic partner, you might even turn it into a shared experience to align your goals and priorities.

Here are a few ways to make your planning retreat meaningful and effective.

Reflect on the Past

Spring is a season of renewal, making it the perfect time to review the last 12 months. What were your biggest wins and disappointments? Which goals did you meet, and which fell off the radar? Where did your time go, and was it well spent? Honest reflection helps surface lessons that can guide your decisions for the next 3, 6, or 12 months.

Set Your Sights on the Future

What do you want to accomplish in the year ahead? Begin with your non-negotiables—things that must happen. Then, build in the “wish list” items that would improve your life: perhaps launching a business, building better habits, reviewing your finances, or starting your estate plan. Factor in fixed dates like vacations, major work projects, or school events that will shape and inform your timeline.

Create a Realistic Action Plan

A dream without a plan is just a wish. For each goal, write down specific, actionable steps. Make them measurable and realistic. Think about what resources, especially time, you’ll need and how you’ll handle obstacles or setbacks. Writing things down helps anchor your intentions in reality and increases your chances of follow-through.

Take the Pressure Off

Start off your retreat with a low-pressure mindset. Spend the first day journaling or brainstorming. Handwriting your thoughts, rather than typing them, can even boost clarity and creative thinking. ¹

Choose an Inspiring Environment

You don’t need a remote cabin like Bill Gates’s legendary “think weeks,” ² but you do want to step away from your usual surroundings. A staycation at a local hotel or Airbnb can work wonders if it helps you disconnect from daily distractions.

Build in Downtime

A planning retreat isn’t all about to-do lists. Make time for quiet activities that help you recharge, whether that’s a relaxing walk in nature, meditation, reading, or just soaking in uninterrupted solitude.

Plan Your Next Steps

Before you head out, get clear on your retreat’s purpose. Are you focusing on career planning? Personal growth? Relationship goals? Estate planning? Knowing what matters most will help you structure your time effectively. Whatever your goals, try to tie them to tangible outcomes. Instead of vague tasks like “start estate planning,” define concrete actions, such as:

• Choosing a guardian for your children
• Reviewing your trust
• Updating your estate plan to reflect life changes from the past year

Annual Planning Retreats and Estate Planning

Setting clear, manageable goals helps curb procrastination and increases the likelihood that you’ll follow through, especially with tasks you’ve been avoiding.

Estate planning is a perfect example. In a 2025 survey, fewer than 25% of Americans said they had a will. Nearly half of those without one admitted they simply “haven’t gotten around to it.” ³ Interestingly, 1 in 5 respondents had at least started conversations with loved ones or done online research, and 1 in 10 had begun drafting a basic plan. This suggests that many people want to start estate planning but struggle to take the final, formal steps, like working with a lawyer to create legally valid documents. ⁴

If you know estate planning is important but haven’t made it a priority, your planning retreat is a great place to start. Use this time to think deeply about your wishes, make decisions, and outline the steps you’ll take next.

When you're ready to move from ideas to action, give our office a call to schedule an appointment with an estate planning attorney. We’re here to help you bring your plans to life with clarity, confidence, and peace of mind.

1. Pamela B. Rutledge, Why Writing by Hand Is Better for Your Brain, Psych. Today (Mar. 7, 2024), https://www.psychologytoday.com/us/blog/positively-media/202403/writing-by-hand-can-boost-brain-connectivity.

2.  Catherine Clifford, Bill Gates Took Solo “Think Weeks” in a Cabin in the Woods—Why It’s a Great Strategy, CNBC (Jul. 28, 2019), https://www.cnbc.com/2019/07/26/bill-gates-took-solo-think-weeks-in-a-cabin-in-the-woods.html.

3. Victoria Lurie, 2025 Wills and Estate Planning Study, Caring (Feb. 18, 2025), https://www.caring.com/caregivers/estate-planning/wills-survey.

4. Id.