Jan. 13, 2022

📝 Bucket Lists and Living a Life Without Regret

Coming into a new year has always had the feeling of starting fresh. The calendar year starts over and we all have a proverbial blank slate to work with. Some of you may be working on new resolutions and others might still be figuring them out. 

What do you want to achieve this year? What do you want to leave behind? Add on the massive reality slap brought about by the pandemic and we’re all forced to consider, what the hell do we want to be spending our time on?

It’s timely that last week’s podcast with Ben Nemtin happened to touch on bucket lists and how we can achieve our goals even when life is trying its damndest to get in the way. So I thought it would be a great topic to tackle in this newsletter. 

📝 Creating a Bucket List

If you’re not familiar with a Bucket List, it’s a list of things you want to accomplish before you die. Or as Ben said, “it’s a list of all the things that are going to bring you joy and happiness in your life.” If you’ve never had the opportunity to dream big, figuring out what might bring you joy can be hard. Almost like having to re-learn what you like all over again.

For me, it involved talking to a few good friends, daydreaming a bit, and lots of google searches. I now have over 100 things on my list, but here are a few highlights that are done (✅) and still outstanding (☐) :

  • ✅ Come within 100ft of a predator

  • ✅ Shake hands with the President of the United States

  • ✅ Star in a movie, even a short one

  • ✅ Travel around the world

  • ✅ Marry my true love

  • ☐ Do stand up in front of a live audience

  • ☐ Learn to do a standing backflip

  • ☐ Run with the bulls in Pamplona

  • ☐ Set (or break) a Guinness World Record

  • ☐ Go on a police ride-along

And while I was pretty happy with my bucket list, after getting a copy of Ben’s book The Bucket List Journal, I realized I had way over-indexed on experiences. So if you’re looking for some help building out a broader list, I definitely recommend his breakdown of categories:

  1. Travel and Adventure - Cage diving with a great white shark!

  2. Physical goals - Being able to do a handstand. It’s harder than it looks!

  3. Material goals - Getting that beautiful Le Creuset cookware set.

  4. Creative goals - Starting a podcast. 

  5. Professional - Becoming a partner at your law firm.

  6. Financial - Saving $1 million. 

  7. Intellectual - Learning a new language.

  8. Mental Health - Seeking out therapy.

  9. Relationships - Checking in with friends more often.

  10. Giving - Becoming a Big Brother or Big Sister.

And if you’re looking for inspiration, you can certainly find plenty of websites on the topic, but I’d also recommend checking out the epic bucket list Ben created a TV show about and/or one of these books:

While creating your bucket list is a great first step towards living a life of more joy and happiness, it’s certainly not enough. I asked Ben about his inspiration for so much of his work and he shared some really sad and eye-opening research about what people regret at the end of their lives.

😔 Top Regrets of the Dying 

During my conversation with Ben, he referenced a study by Cornell professors Thomas Gilovich and Victoria Medvec, which found that 76% of people had one glaring similarity at the end of their lives:

They regretted living life according to other people and their expectations. 

There have been numerous studies and memoirs that reflect the same sentiment. For example, best-selling author Bronnie Ware explored this topic in her book, The Top Five Regrets of the Dying, based on her work as a palliative caregiver. Her list starts with a very similar regret: “I wish I’d had the courage to live a life true to myself, not the life others expected of me” and continues with:

  • I wish I hadn’t worked so hard.

  • I wish I’d had the courage to express my feelings.

  • I wish I had stayed in touch with my friends.

  • I wish I had let myself be happier.

If these regrets are so common that they appear in multiple studies, interviews, and memoirs, why do so many people still reach the end of their lives with them?

❓ Why Don’t We Live Life on Our Own Terms?

Gilovich and Medvec found three distinct reasons why people had this particular regret:

1. We tend not to set deadlines on personal goals. 

It’s easy enough to say, “I want to save money.” Truthfully, it’s a great goal. Most everyone could do with better saving habits. But just saying you want to save money doesn’t really help you save money. It’s too open. You’re not bound to any sort of plan to make it happen. Because of this, it’s easy to have a want or desire but never work towards attaining it.

Elon Musk explained this well, saying “if you give yourself 30 days to clean your home, it will take you 30 days. But if you give yourself 3 hours, it will take 3 hours. The same applies to your goals, ambitions, and potential." 

We set deadlines for so many professional goals, but hardly ever for our personal goals. So if you want to save $10,000 to buy a really nice road bike, you don’t wait to be handed $10,000, do you? If you did, you might be waiting a long time. Instead, try making your goal “save $10,000 for a new bike by June 1st.”

If you want to put the odds of hitting those deadlines in your favor, here’s a shocking stat for you. People who have accountability partners tend to increase their chances of success by 95%1

An accountability partner is someone that can check-in and ask about your progress or talk you through any hang-ups. They might be a professional in the area you’re working on or a friend that has a similar goal. This article from Clever Girl Finance makes a great argument for why we should have accountability partners to help us accomplish our goals.

Finally, some goals might not need deadlines. Maybe it’s a habit you want to incorporate more. If you intend to communicate with friends more often make sure you set calendar reminders for their birthdays or for times to check-in. If learning a handstand is a goal, set aside half an hour at same time every day and practice. 

2. We wait to feel inspired before starting to pursue them.

I think this is one we’re all guilty of. Especially at the start of a new year. We have the drive and motivation to start fresh, eat right, go to the gym, quit smoking, etc. Then, we settle back into our post-holiday routines of work, school, and various responsibilities, and suddenly that energy is shifted towards other things. After all, most people start giving up resolutions by the third week of January and nearly 80% of people have fully given up resolutions by February

You can’t just sit around waiting for inspiration, you have to create that inspiration by taking action. That doesn’t mean you need to know the full path to achieving that goal, it just means you need to take step one. Also, taking time to celebrate or reward yourself for accomplishing those steps along way can help rewire your brain to be motivated to reach the next milestone.

You should also focus on goals that truly excite you. If you hate traveling, airplanes, heights, and bugs, would you feel inspired to work towards traveling to Costa Rica to go zip lining? No, you’d look at it more like a chore than something exciting. Your goals and bucket list should reflect the things that bring you joy as you’ll actually want to keep working at them. Fun fact, for the longest time, I thought “spend a night in prison” would be an amazing thing to cross off my bucket list. Somewhere between getting older and having a child, I realized this would definitely not bring me joy and took it off. 

3. Fear of failure and fear of others' perceptions.

In the blog post that was the basis for her book, Bronnie Ware writes, “Many did not realize until the end that happiness is a choice. They had stayed stuck in old patterns and habits. The so-called ‘comfort’ of familiarity overflowed into their emotions, as well as their physical lives. Fear of change had them pretending to others, and to their selves, that they were content. When deep within, they longed to laugh properly and have silliness in their life again.”

While I’m not sure I realized it at the moment, fear is the primary reason it took me so long to start All the Hacks. Many of my closest friends have heard me describe wanting to do something like this for almost a decade, but not thinking anyone would listen or read held me back for so long. It wasn’t until a good friend forced me to overcome my fears by announcing that I was launching a podcast during a conversation we had on his show. I didn’t love it at the time but am now incredibly grateful for the push.

While hard, it’s important not to be afraid to fail or find that achieving your goal didn’t feel as you thought it would. And as the saying goes, “If you aren’t failing, you aren’t trying.” After all, we’d all be living in the dark if Edison hadn’t overcome 1,000+ unsuccessful attempts at the light bulb. Even when others think your goal is too weird or crazy, never forget that they aren’t the ones who have to live with the regret of not at least trying.

If you find out after achieving a goal that it wasn’t really what you wanted, think about how much you learned through the process! Sometimes those learnings can show you other things that might interest and energize you more. 

Finally, if you’re worried about what others might think of you, the truth is that people are probably thinking about you a lot less than you think they are (and probably because they’re too worried about what others are thinking of them).

🎯 The Takeaway

If you want to set yourself up for success in achieving your bucket list or any other big life goals, make sure to do these three things to overcome the top three reasons people end up living life according to others and their expectations.

  1. Set deadlines for your goals and share them with others to create accountability

  2. Create inspiration through action by taking even a small step towards your goal

  3. Overcome fear by understanding it and embracing learning through failure

🤔 What’s on your list?

Hopefully you feel inspired to make (or update) your bucket list and start living life with far fewer regrets. As I mentioned earlier, I really love adding to my own bucket list and collecting amazing experiences, so if there’s anything on your list you think I should consider adding to mine, please reply to this email and share it!