Looking Back From Your Deathbed… Be Alive Now!

Looking Back From Your Deathbed… Be Alive Now!

Picture yourself on your deathbed looking back on your life…

A few fun vacations, some great nights out with friends, or maybe some great memories with a loved one or kids. Whatever comes to mind, I’m sure there will be some great memories that’ll make you smile.

But now dig a little and try to think about what you’ve regretted not trying or doing more of in life. Maybe it’s the simpler things like sitting back and watching a couple more movies, reading more books, or walking through the park or along the beach.

Perhaps it’s traveling more – something a lot of folks always dream of doing more of but don’t always seem to make a reality.

Or does looking back make you realize that there were things you’ve always wanted to try but never did? Writing a book, learning a new instrument, trying to become a better public speaker (Toastmasters, anyone?), skydiving, or something else?

Conceivably, looking back at your life might make you realize that you weren’t the person you wanted to be. Is it possible that you weren’t as compassionate as you wished you were? Would friends and family not think of you as the person you felt you should be? Should you have been more charitable or philanthropic in life?

It’s time to make the end the means to fix that. Take some time to look at where you’re at now and where you want to be by the time you die. Realize that your day of death could be decades from now, but it could also be tomorrow – you just don’t know.

Start figuring out how to become the person you want to be today and make your dreams happen now instead of regretting that you didn’t make it happen when you’re looking back. I know this is a cliche, folks, but you really do only live once so don’t let life pass you by.

Looking back on life

As both a blessing and a curse, I tend to routinely reflect on my life and ask the question, “How can I be better?” to myself.

I say it’s a blessing and curse because I probably do this too much. My biggest struggle in life is finding a balance between all the different facets of my life. I want to do it all and it drives me crazy to not be able to make that happen at once. Then when I ask myself how I can be better, I find more things that I feel I should be throwing into the mix as well.

Sometimes it’s good to just stop and breathe and enjoy the here and now. And I do that a lot more than I used to, but probably not enough.

Regardless, an exercise I’ve been finding helpful is doing what I talked about in the intro – looking back at my life as if I was on my deathbed.

What’s nice about this exercise is that it helps you focus on what really matters. All those little things that you think are important now might not be as relevant in the long run.

If you put serious thought into this, what will start to float to the top are the aspects of your life that you find to be valuable. So many things might surface in your mind. Anything from:

  • Doing adventurous things you’ve never done before
    • Skydiving
    • Zip-lining
    • Bungee jumping
    • Learning to surf
    • Swimming with sharks (definitely not on my list!!)
    • Trying new and exotic foods
  • Stopping to smell the roses and enjoy nature
    • Camping
    • Hiking
    • Enjoying time at the beach
    • Just being present in the moment
  • Taking on new hobbies and learning something new:
  • Starting a new business doing something that interests you
  • Relaxing with more reading, movies, video games, or other entertainment (check out my Recommendations page for some great books!)
  • Spending more time with family and friends – but actually spending non-distracted time with them
  • Getting in shape
  • Traveling more
  • Meeting new people and making new friends
  • Giving back to others
    • Working with Habitat for Humanity
    • Volunteering at a homeless shelter
    • Starting your own charity or foundation
    • Donating money to help other charitable organizations

Some of these might seem like “bucket list” items to do before you die, which is just fine. But others can mold you into a better person, which can be great for you and appreciated by others as well.

There are millions of other thoughts out there and what’s truly important to one person might not be to another. The key is to put yourself in a position where doing the things that are meaningful in your mind would make looking back on your life fulfilling to you.

I’ve done some of the things that are important to me that make looking back without regret feasible. But just jotting down some of these random ideas here (these are not all relevant to me) compels me to want to write down a list specific to me… electronically, of course! I do this a lot in my head, but writing it out turns it into something real.

Once you’ve completed this exercise, it’s time to actually do something about it!

Making changes…

All of the above is meaningless unless you actually take it to heart and then make it happen.

Remember, this isn’t meant to be a “wish list” but rather a legitimate future you. Now it’s up to you to become and do everything you’ve envisioned!

Working your way backward in thinking like this is valuable because it helps you realize what’s truly important to you. From there, you can then determine how to make the changes to get to where you want to be when looking back at your life.

Leave out the unnecessaries of today and focus on the endpoint. This is the way to truly determine what needs to change. Take some time and examine your written list.

With some of the bucket list types of items, start plotting out when you’ll make them a reality. They don’t need to be done all at once (and probably shouldn’t be), but there’s no reason you can’t assign a year to each (and maybe even the month or season). Then you can get more specific on the date with each item as the year approaches.

Those are probably going to be the most straightforward. Other items on your list might be a little more challenging to implement because they’re likely going to involve change. They may require you to change your routine, your schedule, or even the way you think or treat others.

This might be difficult at first to adapt to, but remember, these changes are to become the “you” that you want to be. This is the “you” that will be looking back from your deathbed with a smile of satisfaction on your face.

Becoming healthy, for example, can be difficult until it just becomes routine (my working out since retiring can attest to that!).

New hobbies and learning something new will also require a sacrifice. You’ll need to exchange some of your free time or re-prioritize to make them happen. You’ll also probably struggle at first while you’re learning, which can be frustrating… practice makes perfect, right?

Some things on your list may necessitate that you change how you treat others and your time with them. That’s a hard one, but the payoff can be huge!

You might also have items on your list that require fair amounts of money to make happen (traveling for instance). Don’t just slough those off and put them on the “someday” list that’ll never happen – do something about it. Create a separate bucket in your savings account if your bank allows it (or create a separate savings account if not). Setup a scheduled amount of money to transfer to it with every paycheck (even if it’s only a small amount). Make it happen.

Even though the changes will likely not be easy, they’ll pay off over time. As you continue to adapt and grow, you’re going to feel happier and better about yourself.

Make the changes today that will make you feel alive with no regrets later!


This exercise of looking back to determine the changes to help you become the person you want to become will change over time. It’s something you’ll want to evaluate regularly (perhaps annually) to see if your desires have changed.

Sometimes things you think you want to do or to become aren’t what you expected. Or those things can change over time. You’ll also want to ensure that you’re staying on track with what you’ve sought out to do.

That’s why you’ll want to review this regularly so you can update it as needed. Plus, it’ll get you reflecting more and hopefully get you more motivated to make it happen.

As I’ve been adding down below before my sign-offs, you need to plan and take action to live the life you want to have.

When you’re looking back at your life from your deathbed, what are you seeing?

Plan well, take action, and live your best life!

Thanks for reading!!

— Jim

You know you wanna share this!!

13 thoughts on “Looking Back From Your Deathbed… Be Alive Now!”

    1. As early retirees, I think you and I have more flexibility in making some changes a little more easily. However, the sooner someone figures out what really matters, the better their path in life can truly be. 🙂

      1. So true, as a 2 year retiree, hitting the COVID year was not exactly the best environment to make our best retirement life. I’m recommitting to taking action. Looking forward not back! Positive Movement in the right direction…incremental steps will add up! Starts with confirming what matters most and weeding out anything not aligned with that perspective.

        1. You said it, Lambo! It’s not always as easy to do if we get caught up in the motions, but after doing a little reflection and committing to making some changes, it can make a tremendous impact on our lives.

  1. Before retirement I had to focus on not being afraid to say “no”. This kept me from being overextended, overworked and burned out. Now that I have achieved an early retirement I have switched to learning to say “yes” more: Like going hiking even when it is raining, Trying a new skill, Stretching outside my old routines and hesitations, Meeting and talking to new people (despite my introvert instincts). I now have time to research something new that I have observed or read about. I feel like a river that has overflowed its banks and can spread in new directions.

    Because I am free from the stresses from work, I have the internal reserves to absorb the little stresses of trying new things and growing in new directions.

    I like your suggestion to think backwards from the end. A wider perspective can help identify paths to explore earlier in the flow of retirement.

  2. It surprises me that everyone isn’t already living like this. I mean why in the world wouldn’t you live your best regret free life? I’ve stepped out of my comfort zone to grow my entire life and my life is full now in retirement because of it. I’ve got so many fun hobbies and tons of volunteer work that I’m not really seeking new things very much because I’ve really honed in on the things I love and that give me purpose. Life is so good! This weeks activities include running miles with my friends at 5:30 in the morning, pickleball, tennis, fishing, starting a 6 week 20 hour a week volunteer project, a birthday trip, a meeting to pick who gets $350,000 of our foundation grants this year, a meeting with a financial advisor who’d like to help invest our foundations 8 figure portfolio, a meeting with our states Economic Development Director at the state capital and a meeting with a Fortune 500 hospital chain president about their plans for our local hospital. And maybe a small amount of paid expert witness testimony, not sure if that won’t wait a couple of weeks. I don’t need any paid work but I am helping some friends out so I felt I had to take it. Next week will be much the same, another good week. I’m not planning on having any regrets on my death bed.

    1. Damn, you’re one busy guy, stevark!! 🙂 You’re doing it right for sure, but unfortunately, I think life gets in the way for many folks. Maybe they don’t like change or to step out of their comfort zone and that leads to being stuck in a rut and some unhappiness. Or maybe it’s not that dramatic where someone is content with life but just isn’t seeing the full potential of what they want their life to be like. Taking the time for a little reflection and making the changes to make it happen can be the cure for that.

      Nice job on rocking it! Running at 5:30 in the morning though? Ugh, wake me at 7:30! 😉

  3. That’s the problem with ruts, nobody likes stepping out of their comfort zone. It takes courage to take risk. You realize you are afraid but do it anyway. I know that’s not natural but people who can’t push through fear have very hard lives. I didn’t want to take on this latest volunteer role, its too high profile and if I screw it up I’ll make some very important people unhappy with me. But I know I’m good at getting things done and the odds are high in my favor that all I’ll do is impress them with the job our team does. I’m excited about it now but until I stepped over that discomfort and said “yes” I couldn’t get to the excitement and growth part. And I have gone down in flames a few times, but it is rare. And generally the worst that can happen is not as bad as your fear leads you to believe. And sometimes, like you said, people just settle for what they have because it is the safe path. But life should be extraordinary, who wants mundane? 5:30 is early, dark and cold this time of year. But I’ve got great running buddies and its just when we all can get it done. Some aren’t retired yet so can’t run later in the day, plus we run on the streets so, traffic.

    1. Love it and so true on all counts, steveark! Still too early for me on the running (I’m a late guy), but I think that’s awesome you have non-retired folks joining you before work – that’s dedication! I’m currently walking up and down flights of steps (75 times each) with a backpack of weight almost daily preparing to hike up a volcano in a couple of months just because it sounded like a good challenge. 🙂

  4. I really need to get back into exercising. I just couldn’t get into the routine since the pandemic started. There are too many people at home and it doesn’t work. I might need to join a gym, but then I don’t know if I’ll make it in. Well, next year it’ll be on my goal list.
    As for looking back from my death bed, I don’t think I would regret anything. Not that I’m perfect or anything. It’s just that I rarely look back. I only look at the present and forward. My wife looks back a lot more and wonders what could have been and such. It just isn’t in my DNA. The past is gone.

    1. I’m similar on the gym, Joe. I’m lucky that the one I have right now is less than 1/2 mile away, is never crowded, and I have great weather to walk to it. I’m not sure what I’ll end up doing once we move back. I hope you crush that goal next year like you do most of your others!

      That’s a great quality to be able to only look at now and the future. Sometimes it’s good to reflect to learn from your mistakes, but regretting the past never changes anything.

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