8 Ways to Create a Realistic Retirement To-Do List

Retirement can be one of the most fulfilling stages of your life, provided you plan ahead to ensure it meets your needs and wants. It forces you to look back and ask yourself, What remains to live or to accomplish? What would I regret NOT doing? Here are some useful tools and strategies.

1. Brainstorm

Start with a good old-fashioned brainstorming session. Make a list of all the things you’ve always dreamed of doing, from skydiving to reconnecting with an old high school friend. Don’t stop until you’ve exhausted all possibilities.

2. Take a break

Now let it sit for a day or two. Putting it out of sight and out of mind will provide a new perspective. Then review your list and resume brainstorming until you run out of ideas again. Keep in mind that there is no magic number to aim for, as long as the elements accurately reflect what you want this stage of your life to look like. Now is the time to evaluate.

3. Evaluate your entries

Starting at the top of your list, rate each item on a scale of 1 to 5, with 1 being the least important and 5 being the most important to you. Then go back and put a line on each item with a rating less than 3. Don’t delete these items yet, because you might want to revisit them later.

4. Ask these questions

For items rated 3 and above, ask yourself the following questions. I suggest you respond in writing.

  • Am I mentally and physically able to do this activity?
  • Can I afford it? Does this fit into my budget or will I have to stretch?
  • Is it something that I really wanna do or is it just something i always have thought I wanted to do?
  • Is there a reasonable plan B? If it’s not possible to do an activity on your to-do list, is there a more doable option that still resonates with you? For example, if you’ve always wanted to travel to Spain, but prefer not to leave the United States, is there another destination you’ve always wanted to visit in the country? Maybe even a place with a similar climate, great Mediterranean restaurants or a museum of Spanish art?

5. Prioritize

For items rated 3 and above, rank them in order of what you want to cover from first to last.

6. Plan

Starting with the first item on your list, start planning. Remember, the best plan on the planet is worth nothing if you don’t implement it. iWish is a great bucket list planning tool (an app available for Apple) that can help you reach your goals, achieve your dreams, plan your trips, and more.

To get the ball rolling, ask yourself, What reasonable step can I take to start planning the first item on my to-do list? The momentum will kick in once you take that first step. If you don’t know where to start, check out this really simple article on how to travel the world after you retire.

7. Troubleshooting

Anticipate the unexpected. While a bucket list may look good on paper, putting it together can be daunting. For each item on your list, try to think of any potential blocks or obstacles that might get in your way. For example, if your regular pet sitter isn’t available when you need them, make sure you have a backup just in case.

If you prefer to do an activity with a buddy, discuss it with him in advance. Don’t assume you’re on the same page without checking it out first. Different people have different interests, so you may need to find more than one mate. Group activities are ideal for impulsive interaction when a friend is unavailable. Local senior centers, community centers and adult education venues are good resources for a variety of activities – and can meet people with whom to tackle your to-do list.

If travel is a key item on your bucket list and you want the freedom without the hassle of planning, group travel may be the way to go. This way most of the details including travel, accommodation and itinerary are taken care of. All you have to do is pay and show up. To verify Travel + LeisurePicks of the best age-friendly travel groups for more inspiration.

8. Face your fears

It’s also important to face your fears and any tendency to procrastinate when building your to-do list. Often the items on your list are things that you’ve always wanted to do, but haven’t been able to do or something has always stood in your way (see blocks and obstacles above). You kept postponing it until it finally ended up on your default retirement bucket list. Which brings us back to number 3: Is it something you really want to do or just something you always have thought you wanted to do?

As you age, you may not be as fearless or your body may not be as cooperative. If an item has been gathering dust on your to-do list for over a decade, you might want to reassess and see if it still makes sense in terms of who you are today. If that scares you, dig deeper. Should we ignore caution or take a more calculated risk?

Do you remember any items on your brainstorming list that were rated less than 3? If they’re still talking to you or you’re not sure, stick them at the end of your to-do list and reevaluate them when you get there. Your bucket list is a living document that morphs and changes as a reflection of who you are at any given moment. As you cross out items, new items may be added or you may decide to remove some for some reason. Your bucket list is a dynamic tool that is under continuous review.

At the end of the line : Will it be now… or never? Imagine being at the end of your life, to-do list in hand. Some of your articles are crossed out, others are not. Looking back at your list, what items do you most regret not accomplishing? That is where you should start. Remember, “You can pray for potatoes, but you better buy a hoe!”

For additional tips, check out all of our bucket list content here and read more at

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