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  • Writer's pictureJon D'Alessandro

How to Write a Compelling Bucket List (that Doesn't Sit in a Drawer) — 6 Tips + Prompt!

We're 3 months into the new year, and hopefully you’re taking initiative to make the Roaring Twenty-Twenties your best decade yet.

This time of year, however, our focus starts slipping away from our aspirations and resolutions. The books go unread, the gym visits become less frequent, the sugar sneaks back into our diet. We get swept back into the BAU and the usual BS.

The best way to combat this natural dip in enthusiasm is to not only revisit your annual goals, but take it a step further: create your bucket list.

About the Bucket List

Put simply, a bucket list is a catalog of things you want to accomplish within your lifetime. They can be smaller goals — like visiting a distant relative, learning to cook a specific cuisine, or developing a new skill — or bigger — like starting a nonprofit organization to save the Northern white rhino, or witnessing the decennial Passion Play live in Oberammergau.

The phrase "bucket list" came to use as we know it in the late 90's, and is used interchangeably with less morbid euphemisms like “life goals” or “trophy lists” (1).

You might have some vague list of aspirations in your head, but the less seriously you take the goal-setting process, the harder it will be to accomplish anything truly and personally meaningful.

What we’re creating is a concrete list that's powerful, not perfect. Inspiring, not laborious. Keep this famous Mark Twain quote handy as you go along:

“Twenty years from now, you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” — Mark Twain

Give some thought to your bucket list and what you want to do, have, and be in your lifetime. Use the following 6 tactics to create — and pursue — a list that maximizes your potential, and builds commitment and engagement into the process:

1.) Be ambitious. Use your creativity. Go for what excites you.

This is not the time for SMART goals. Your life goals should be ambitious, imaginative, and exciting.

If an item on your list starts feeling boring, incongruent, or unnecessary, not only are you missing the point, but it'll sap your motivation, making it harder to complete other items.

Each goal should stretch you, or in some cases even scare you. They should be original and align with your true values. And they should always excite and inspire you. These are the keys to an ultra-inspiring bucket list.

2.) Surround yourself with the right people

This one comes from clinical psychologist and writer Alice Boyes Ph.D:

"Social psychologists have identified an effect called social contagion. You can catch extra willpower from your friends, so if you want to achieve your bucket list, make friends with people who are achieving their bucket list." — Alice Boyes, Ph. D

Partner with friends who have a Bias for Action, and not those who — as our cousins across the pond might say — are all talk and no trousers. Use social contagion, peer pressure, and friendly competition to your advantage.

If you can connect with role models who already accomplished something on your bucket list, all the better. You'll have extra inspiration, as well as advice, encouragement, and reassurance that it can be done.

3.) Break your goals down into tiny, impossible-to-screw-up pieces

In the early 1980's, two young brothers, Will and Harry, watched their father tear down the wall in front of his old Philadelphia bakery. Then he handed them shovels and supplies, and gave them the impossible task of building a new wall in its place. Will was 12 years old, his brother even younger.

They worked every day after school, digging a 6-foot hole for the foundation, mixing concrete by hand, laying the bricks. Will remembers staring at the void, resignedly thinking "There's going to be a hole here — forever."

But miraculously, after a year and a half of backbreaking work, they laid their last brick.

The Smith family stood back, admiring their new wall. The father turned to his boys and said:

"Don't you ever tell me you can't do something."

Will Smith remembers it to this day, hundreds of bricks, dozens of records, and a handful of award-winning movies later.

By breaking your goals down into small, simple tasks, making marginal adjustments to your habits and routine, and executing consistently, you can make even your most overwhelming, unattainable dreams a reality.

“You don’t set out to build a wall. You don't say ‘I’m going to build the biggest, baddest, greatest wall that’s ever been built.’ You don’t start there. You say, ‘I’m going to lay this brick as perfectly as a brick can be laid.’ You do that every single day. And soon you have a wall.” — Will Smith

4.) Block recurring time to revisit your bucket list

Right now, block off a recurring time slot in your calendar to revisit your bucket list. Make sure it’s at least annually, but ideally every 6 months or less.

This is your self-coaching progress check-in. Take a few minutes to:

  • Revisit your commitments

  • Break the bigger items down into more manageable chunks

  • Celebrate what you've done so far (don't skip this step!)

  • Reflect on whether your superordinate goals really move the needle or if your strategy should pivot.

This is one way to ensure you don’t pour your time and enthusiasm into a bucket list only to leave it forgotten in a drawer or drive. Another way is...

5.) Practice extreme accountability

Here are some surefire ways to build accountability into your bucket list endeavors:

  • Post your list publicly (some or all of it, depending on your comfort level), declaring that you will achieve these goals, and that you need friends and followers to help hold you accountable. As a bonus, someone might even come out of the woodwork with an offer to help.

  • Ask a friend or loved one to regularly check in on your progress (or join you to check off an item!).

  • Follow bloggers and influencers who are pursuing their own bucket list. It'll keep yours top of mind, and give you an extra dose of inspiration.

  • Write out a big, fat check to an organization or charity, pass it to a friend, and agree that if you don't make a certain amount of progress in a given timeframe, they will mail it out.

Once the initial surge of enthusiasm dies out, it's easy to dismiss your bucket list, remembering it only when you’re riding some caffeine tidal wave, or when you’re listening enviously to someone's epic adventure story. Accountability is crucial.

6.) Need help getting started? Follow this prompt:

Brainstorm and write down at least 2-3 life goals you have in each of the following areas. You can go back and add or edit later. It doesn't matter how big or small, how close or far they seem, or how outlandish or unachievable they feel. Want to take a vacation to Mars? Write it down (and pray for Elon).

Try giving it a shot now — and don’t forget, ambitious, imaginative, and exciting:

  • Family

  • Friends

  • Food

  • Career and business

  • Financial

  • Adventure and travel

  • Skills and hobbies

  • Unique experiences

The clock is ticking

Hopefully now you have a strong, actionable bucket list that you can break down into manageable chunks and start doing. Don't forget to set a reminder to periodically revisit your goals, and to leverage your network for accountability and inspiration. Overcome your initial fears and doubts, and start laying bricks, one by one.


P.S. — If you enjoyed this article, subscribe to my newsletter below for more advice on creating inspiring, actionable goals, and ideas for a more fulfilling, adventurous life!

(1) Google’s Ngram shows the phrase originating in the 1960's, but likely because their algorithm struggles to discern “bucket list” from “bucket lift,” a machine used in construction that was invented around this time. The s/f confusion is a common and frustrating issue with OCR software — why I know this is a story for another day.


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