Is It Time for an Annual Planning Retreat?

Do you ever feel like you never have a moment to yourself? Or that even if you manage to carve out some personal time, you are not spending it as effectively as possible? An annual planning retreat might be the solution you need.

Our always-on culture may counterproductively (and counterintuitively) hold us back from achievement. We can work hard and stay busy without making real progress on our long-term goals. Caught up in our day-to-day lives, we may lose track of the future and what we are working toward.

By reflecting on your successes and failures from the past year and your priorities moving forward, you can bring more intentionality to your life and make conscious choices, including estate planning decisions, that align with what truly matters to you—not just now, but in the long run.

What Is a Planning Retreat?

You might have heard of a wellness retreat—a getaway that offers the chance to focus on self-care, relaxation, and spiritual growth.

A planning retreat is similar to a wellness retreat. Both are intended to promote time away from the stresses and distractions of everyday life. Both have become more popular in response to the burnout that many feel living in a fast-paced, tech-connected society that increasingly blurs the lines between work and personal life. While wellness retreats are more about enhancing present well-being, planning retreats emphasize achieving future goals—both personal and professional.

A personal planning retreat can be a game changer. By removing yourself from your usual routine to self-reflect, set goals, and plan strategically, you can come away with a renewed focus on your future and the steps needed to get there. When you have a plan in place, you feel more in control of your circumstances, which can reduce the anxiety and stress that may hold you back from making real progress.

How Does a Planning Session Work?

A planning retreat does not require specific rules to be effective. You just need to set aside a meaningful amount of time to reflect on the past year and chart your course for the year ahead.

Think of your planning retreat as your personal company retreat. However, if you have a significant other, you might consider making it a joint effort to ensure that you are on the same page concerning planning.

Here are some ideas to help you make the most of a planning retreat:

• Look back. Spring, in particular, is associated with fresh starts and renewal. Take some time to review the past 12 months. What were your wins and losses? Which projects exceeded expectations, and where did you fall short? What could you do differently next time? Were there things you wanted to get done but did not? Conversely, did you spend time on projects that did not move the needle or that could have been better spent elsewhere? An honest assessment can provide valuable insights to inform your plans for the next 3, 6, or 12 months.
• Look ahead. What do you want to achieve in the next 12 months? Start by planning for the things you know you must get done. Then, make plans for things that are not required but would improve your life. These may be bigger-picture considerations such as starting a new business, reviewing your finances, budgeting, and creating an estate plan. As you plan, identify fixed events—such as vacations, work projects, and school activities—that you cannot easily reschedule and will need to work around.
• Develop an action plan. A goal without a plan is just wishful thinking. Creating a roadmap for achieving your goals and writing it down can increase your chances of success. For each goal, outline the steps needed to achieve it. Make the steps specific, measurable, and, perhaps most importantly, realistic. Identify the resources—including the most precious of resources and time—required to bring your vision to fruition, as well as the potential obstacles you might encounter and how you will deal with potential setbacks.

Early in the planning process (say, day one), you can take a more casual approach, such as brainstorming and journaling, to give you time to relax and your thoughts space to breathe. Try writing by hand, which science suggests is better for processing information.^[1]

Choose a location that inspires you and promotes reflection. You do not have to retreat to a secluded mountain cabin like Bill Gates did on his “think weeks,”^[2] but you should pick a place that takes you away from your usual routine and daily distractions. That could mean taking a staycation at a hotel or Airbnb.

Planning retreats should not be all work. Schedule time for activities that help you relax and recharge, such as reading, taking a walk in nature, meditating, or simply enjoying some quiet, uninterrupted time.

The typical planning retreat can last two or three days a week. If your schedule does not allow that, a full day or a series of afternoons can be just as effective. Plan your retreat and block off the time on your calendar.

Before packing your bags, clarify your retreat’s primary purpose. Are you primarily focused on career planning, personal growth, relationship goals, financial planning, or a combination? A clear focus and intention will help you structure your time to address your priorities.

Whatever objectives you set, tie them to tangible outcomes. For example, instead of setting the goal of “review my estate plan” or “start the estate planning process,” a more specific objective might be to choose guardians for your minor children, set up a trust, or identify changes during the past year (e.g., marriage or death in the family) that should be reflected in your estate plan.

Annual Planning Retreats and Estate Planning

Setting clear, achievable goals can help reduce procrastination and increase your likelihood of following through on them.

Procrastination is the top reason people do not have an estate plan. Fewer than one-quarter of Americans reported having a will in a 2025 survey, and nearly half of respondents said their lack of estate planning is because they “just haven’t gotten around to it.”^[3]

However, around 1 in 5 respondents without a will have started to talk to their loved ones about their wishes or to research estate planning online, while about 1 in 10 have started to write down a basic plan.^[4]

These findings suggest that many people want to start estate planning but have not formally begun the process. In many cases, their efforts stop short of consulting a lawyer or creating legally valid documents—concrete actions that turn estate planning from a vague to-do item into an officially documented plan.

If you recognize the importance of estate planning but have not yet prioritized it, put it on your planning retreat agenda. When you are ready to take the next step, Book a FREE Discovery Call.

^[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.