The Ultimate Strategic Life Decision

The premise behind being strategic is simple - begin with the end in mind. My first encounter with this principle came from Stephen Covey’s classic book, The 7 Habits of Highly Effective People.

When I worked at McKinsey, much of the client work was focused on this principle — begin with the end in mind.

When it comes to your life, the same principle applies — begin with the end in mind.

In life, most people at best think about what they want out of their life and career over the next 1 to 3 years. However, there’s another approach that is even more strategic.

That is to consider what you want your life to represent to you on your death bed.

Yes, the ultimate way to begin with the end in mind is to begin with the end in mind. On your death bed, when you look back, what do you want to be true?

I’ve been thinking about this a lot the last two or three years.

I’ve hit the age where I now get more funeral notices than wedding notices. I’ve had high school classmates die, former McKinsey colleagues die, recent clients die, relatives die, friends whose parents recently died, friends with significant others who died.

Although I logically understand that our time on earth is finite and that we all die at some point, it’s entirely different when the people who die are people you actually know, or when close friends are grieving for their losses.

There have been a few lessons I’ve learned through this process that I’d like to share:

1) If you ever have the chance to visit someone who is dying, but has not yet died, do it. You will never regret it.

I’ve opted both to visit and not to visit people I knew who were dying. What I underestimated at the time was how meaningful saying goodbye to someone while they are still alive would mean to me and to the other people who survive that person. I also underestimated how much I would regret not making the effort to visit someone who is on death’s door.

With death, there is no second chance. There is no "I’ll see them next time." When someone is dying, you don’t know exactly when they will pass. If you have the “fortune” to know in advance that someone is near passing, JUST GO.

You will never regret it. Don't be like me. I live with regret for the people I didn’t go to say goodbye to. I will carry that with me the rest of my life. I hope you don’t ever have to do the same.

2) At the end of one’s life, one of the two big questions dying people seem to ask themselves is this, “Will the people I leave behind be okay?”

As I’m writing this tearfully, I am thinking of two friends who passed — one a man, the other a woman, vastly different in age and family circumstances. Both died with some advance notice, and both through their actions and words were just hoping beyond hope that those they left behind would be okay.

(If my late friends happen to be reading this from a “better place,” the answer is, "Yes. Everyone you were worried about, they are all okay.").

The practical action item here is to take proactive steps around life insurance, estate plans, letters to your survivors and the like.

One of the most sobering things I ever did was when my attorney indicated that it was possible to write letters to various family members and have those documents be stored with my will. I wrote goodbye letters to each of my kids — that was just emotionally brutal and hard to get through it without a great many tears.

What it also did for me was give me great clarity as to what (and who) was important to me.

3) The other big question (more of an observation really) dying people seem to ask (or consider) is an inventory of their relationships.

On your death bed, you truly do not think about your resume. What you do is look at whose lives you touched, who came to say goodbye, and who loves you. That’s it.

I’d argue that if you died with a billion dollar net worth, but died with nobody by your side despite ample time — in so many ways, you died broke.

I watched one family friend slowly pass away over 4 months. What she did during that time was quite remarkable. She called everybody in her life who cared about her and said, “I’m dying. Will you come out here for a week or two and take care of my family because I can’t do it right now? I need your help. It is the last favor I will ever ask of you.”

What happened next really touched me. I saw an endless parade of friends and family, each taking one to two week shifts. Friends from high school, college, one city or another... all flying in to help her out.

I have no idea what her financial situation was when she passed, but it was pretty clear to me that she lived a remarkably rich life.

There’s one exercise that I’ve been trying to do for many years now. I’ve never been able to successfully do it, but here it is.

Write the obituary for yourself that you hope will be true by the time you die.

When I first tried this, mine looked like this:

“Victor Cheng passed away today. He was...”

...and then I would get stuck.

What was I? In 200 words, how do I describe the sum total of my life? Is it my work? Is it my relationships? Is it my resume? My net worth?

Going through the process prompted more questions than answers, but they were the right questions to be asking.

(I know it’s a bit morbid, but if beginning with the end in mind is strategic, then logically it would seem that before you start the rest of your life, you should define what your death looks like, right?)

To this day, I haven’t been able to finish that 200-word writing exercise, though re-attempting it every two or three years has brought me greater clarity. There have been a few themes that have been popping up fairly consistently over the last few attempts.

As I look at these themes, and then look at my life and career plans, I’ve noticed how they’ve increasingly been in alignment these last few years.

If I ask myself to what extent the time I spent this year is going towards things that make my idealized obituary true, it turns out quite a high percentage of my time has gone to exactly that.

That definitely wasn’t the case for certain time spans of my life and career, but these days I’m very much on strategic focus.

What about you?

How would your obituary read?

How much of your time this year is in alignment with the parts of your idealized obituary that are not yet true?

That is beginning with the end in mind... literally.


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48 comments… add one
  • Ank May 19, 2014, 11:42 am


    Great article. In your earlier posts, you highlighted winner’s attitude of never quitting. In the pursuit of working hard continuously, one may compromise certain things in life to GET them later.. while “later” may not come at all.

    While the answer to my question (how to achieve this balance?) will vary person-to-person, how do see balancing so many things in life – health, relationships, and career? The internal script that runs in most people’s mind is – alright. let me go to this school, let me get this job, and then everything will be okay and I will focus on lets say health/meeting women/taking a vacation etc. I recall another point you made in your earlier post when a person living nearby Hawaii beach wonders why people work for their entire lives to ultimately come there to enjoy their vacation, when he has been doing so daily. Also, job promotion may not actually feel like a promotion on the day of a break-up! Since individual priorities change with time as well, I wish there was something that one can use to determine how to focus one’s time to avoid guilt feelings later on..

    Look forward to hearing your thoughts.

    • Victor Cheng May 19, 2014, 8:40 pm


      I haven’t thought about this topic very deeply yet, but one thought comes to mind.

      1) If you died yesterday, would you have been comfortable with your choices up until then.

      2) If you will live to 100 years old, are you comfortable with your choices today.

      When I use the first test, I tend to think about relationships. Did I tell everyone I love, that love them? Did I end the day angry at someone I cared about and is that their last memory of me? (By the way, a good rule of thumb is to never end the day angry or resentful of people you care about. Try to get all fights resolved so they don’t spill over )

      As I use the latter test, I tend to start thinking about my health. Will my body and organs physically last to 100 years old? Am I in a good spiritual health or will I drive myself crazy by then time I’m 100 years old?

      Another useful distinction that I come back to over and over again also comes from Stephen Covey. He distinguishes between the “Important” vs the “Urgent”.

      Emails are urgent though rarely importantly. Have difficult conversations with people your care about are very important – but often not seemingly urgent.


  • Swati Sinha May 19, 2014, 10:52 am

    Hi Victor,

    Great thought as always, your post has always encouraged me
    Being a young graduate, life is not much figured out yet for me. With unexpecting turn of events it has been difficult to judge everything as well but I use to always do one thing and that was thinking of a better future, I think that has kept me going till now . I always thought that was day dreaming but after reading your post I will definately focus more on thinking to the end point.

    thank you for your always encouraging post.


  • CocoGaugin May 19, 2014, 10:18 am

    I’ve been reading you from the beginning of your journey….though I am poverty ridden, yet educated, life itself makes decisions for you. Yes, one has choices and can do right, you know there are thoughts with other motives. My point, it is in the details….how do I make an estate will? Plana funeral? How much is a casket? A headstone, websites to steer me in those directions and how to’s on that hits home and is where I am at. That is where most fear to tread and ask the really hard questions. When to turn off the machines. We are ready for the hard stuff and want smart serious answer from guys like you who give us great guidance and advice. What say you to that?

  • Thiago May 19, 2014, 9:55 am

    Hi Victor,

    I find remarkable how you go about so many different topics in such an interesting way.
    You are a true mentor and I really wanted to say to you how your words have the power to motivate someone reading it from the other side of the continent down here in Brazil.
    This article, in special, tells a lot more than it seens. Although all your articles about work carrer are very important, this one is what life is all about.

  • Anil May 19, 2014, 9:32 am

    Hi Victor,

    A very touching article; personally I try to read all of your letters whenever time permits. I must admit, I started giving respect to you because of your expertise in management consulting but over a period of time I respect you more because of your life touching thoughts. Some of your thoughts on realistic philosophy are good enough to convert into a few essays which can be collectively part of a book on realistic philosophy.

    Coming back to the main topic of death bed and how we want to be remembered; I would say, personally, I want to be remembered as a real life philosopher, who inspired people, who asked people to take control of their lives, who asked people to be more real and less artificial, who asked people to give more and love more, lifelong student, and a strong supporter of equality.


    • Victor Cheng May 19, 2014, 8:33 pm


      What a wonderful vision you’ve painted. The hard part is taking some action, no matter how small, each day to make progress in one or more of those areas.

      Best wishes,

  • Alex May 19, 2014, 9:25 am

    That is where I think of eternity of my spirit
    That is where one can read the Book – Purpose Driven Life
    That is where the end is – heaven

  • Emerson May 19, 2014, 9:20 am

    Hi Victor,

    Thank you so much for this post. I usually take a couple of minutes to read your posts and those are very helpful. However this post is one of your best, it belongs not only to a case interview website but to an life-inspirational website.
    Thank you again, I will share your thoughts with my family and circle of friends.
    Please keep posting.
    A big hug from Germany.


    • Victor Cheng May 19, 2014, 8:32 pm


      Thanks so much. I will keep posting. And a hug back.


  • jian May 19, 2014, 9:17 am

    “live each day as if it was your last,” this quote we hear so often nowadays, but I still don’t have a clear idea what it really means. Victors has pointed out some pragmatic way to live with this mindset. Thanks!

  • Joel D May 19, 2014, 9:01 am

    Hi Victor,

    I just came across this HBR article recently entitled ‘To create a real-connection, be vulnerable’. I’ve noticed that in all of your articles you show a lot of your human side, emotion and have been candid about your feelings while going through both good as well as embarrassing situations. I don’t know if other consultants or left-brained people are comfortable doing this.

    I believe this is why you’ve struck a Chord with many of your readers…other than the Case Interview related products and articles that you’ve been selling and sharing.

    Kudos! :)

    • Victor Cheng May 19, 2014, 8:31 pm


      I read that article too and if I remember correctly, agree with it. Being vulnerable shows your humanity and allows others to relate to you as a human being.

      Many very successful people are perfectionists (I’m a recovering perfectionist) and have a strong desire to be seen in as good a light as possible. This is basically the present yourself in the best possible light.

      This is a great strategy in a job interview. However, if you want to build an emotional connection with someone (no merely an intellectual one) it requires showing your full range of humanity.

      I’ve seen this done in small group settings where total strangers can be bonded to each other emotionally in a matter of minutes through shared vulnerability, that is much more deeply connected than people who have had purely intellectual relationships with each other in some cases for years or decades.

      For more on this topic, see Brene Browns two wonderful TED talk videos. Excellent stuff.


  • Winston May 19, 2014, 8:58 am

    Thanks for writing this post Victor. Very good reminder of what’s important and how to live the ultimate strategic life. I’ve read and love the 7 Habits of Highly Effective People too, and your article inspires/reminds me to complete my personal mission statement and obituary.

    On another note, I’ve been considering subscribing to the strategic outlier, but I have a few questions/things that are unclear to me:
    (1) what will be covered in the content?
    (2) I really prefer not to have a physical piece of paper; Is it possible to recieve a PDF?
    (3) Do we get access to past letters when we subscribe?

    Thanks again for writing a great post!


    • Victor Cheng May 19, 2014, 8:24 pm


      He Strategic Outlier covers a wide range of topics – pretty much the full breadth of everything I know – analysis, relationships, life goals, conflict resolution, sales, executive presence, presenting skills, personal competitor advantage, entrepreneurship. Back issues are available for purchase for active members. The newsletter is currently print only.


      • rajan t mehta May 20, 2014, 3:45 am



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