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.