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Ash RoyFeb 15, 2014 11:14:58 PM17 min read

The Steve Jobs guide to Using Death as The Ultimate Change Agent


Have you heard the phrase “There are no guarantees in life?”

It’s nonsense!

If you’re a human being (which I assume you are, since you’re reading this) two things are most certainly guaranteed!

1. Change.

2. Death.

Sounds morbid, I know this is simply a fact of life. But there is a point to this morbidity, as you will see later in this post.

Your could reach the epitome of success and still have regrets.

There’s no getting away from change and death.

And yet, we seem to fear those two things more than most.

Isn’t it funny how the mind works?

I remember having this sense of invulnerability as a kid. It stayed with me through my teens and my early twenties.

Death was this distant possibility — way beyond the visible horizon.

But then, as the years rolled on, I noticed folks in my grandparents’ generation leave these earthly shores.

At first, it was a trickle. And it was easy enough to ignore the first few.

But soon enough, when the trickle became a consistent pattern, the message came through loud and clear.

Steve Jobs' death made me realise that the best doctors in the world can't help you if you're lying in a sick bed with incurable cancer. 

Death is inevitable and no one escapes it. 

Seems naïve when I read these words as I write them down, but here‘s this thing:

Most of us don‘t really want to face our own mortality. And we’re not willing to acknowledge it until it’s no longer possible to ignore.

But there’s an important lesson in this (as you’ll see later in this post).

Death can be an extremely powerful motivator when you use it as a device to prompt effective change. Being aware of the fact that you have a limited time on earth can create a strong sense of urgency (and agency).

It also helps you understand the importance of listening to your own inner voice and not being too focused on the results of other people. 

The best thing you can do is not get too caught up with other people's inflated achievements and an unrealistic image of their lives projected on social media. 

The material things of this world and acquiring new things may seem to be really important but these things change as you progress through the stages of life. 

Ultimately what matters is understanding your true calling and not getting too focused on getting the coolest new things or being a winner in others' eyes. 

It can help you realize your dreams and focus on what matters.

Steve Jobs by Walter Isaacson

If you haven't already read it, I highly recommend reading the book Steve Jobs by Walter Isaacson. It gives you a deep insight into how Steve Jobs thought and why he made the choices he did. 

A lot of his choices appeared to be contradictory on the surface, but I found that reading the book gave me a clear understanding of his motivations — particularly in the context of this "life is short so make it count" filter he applied to a lot of his decisions later in his life. 

I recommend grabbing a copy of his book. Click on the link below to grab it now. 

Why Your Own Death is Your Ultimate Change Agent

Once I realized that death was no longer an intellectual concept, but rather an inevitable part of life, I found myself asking a very important question:

What was I going to do between now and that day when I left these earthly shores?

Steve Jobs said it perfectly in his very inspiring speech at Stanford commencement address :

“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to make the big choices in life. Because almost everything, all external expectations, all pride, fear of embarrassment and failure, all these things just fall way in the face of death. Remembering you’re going to die, is the best way I know to avoid the trap of thinking you have something to lose”

(I’ve extracted the key insights from his speech, and tagged them (e.g. 5.22mins) so you can go right to the bits that interest you in the video):


By the way, if you haven’t already read Walter Isaacson’s book titled Steve Jobs then I suggest you do so. Steve’s story is fascinating and inspiring.

Anyway, here are the key Insights from Steve Jobs’ Standford university commencement speech:

  • His first story is about connecting the dots. (0.45 mins)
    • (0.59 mins) Steve tells us the story of his birth and his developing years.
    • (2.27 mins) He talks about how he followed his intuition which later turned out to be one of the best decisions he made.
    • (3.18 mins) An example of following his intuition which turned out to be priceless later on. His point: You can’t connect the dot looking forwards. you have to trust the dots will connect in the future.
    • (5.07 mins) Believing the dots will connect in the future gives you the confidence to follow your dreams.
  • The second story is about love and loss. (5.22 mins)
    • (5.13 mins) He started Apple with Steve Wozniak and then got fired at 30 from the company he founded!
    • (6.51 mins) He realized he still loved what he did and started over.
    • (7.10 mins) The heaviness of being successful was replaced by the feeling of lightness.
    • (7.15 mins) He founded NeXT and Pixar — which became the most successful animation studio in the world
    • (7.36 mins) Remarkably Apple bought NeXT and Steve returned to Apple. Next is at the heart of Apple’s technology. None of this would have happened if he hadn’t been fired from apple.
    • (8.08 mins) You’ve got to find what you love and the only way to do what you consider great work is to find what you love. Keep looking. Don’t settle.
  • The third story is about death. (8.50 mins)
    • (8.59 mins) At age 17 he read a quote that said “If you live each day like it was your last someday you’ll most certainly be right”
    • (9.10 mins) This quote made an impression on him and since then Steve Jobs asked himself every day “If today was the last day of my life would I want to do what I’m about to do today?” When the answer was “no” for too many days in a row he knew he had to change something.
    • (9.24 mins) Steve explains “Remembering I’ll be dead soon is the most important tool I’ve ever encountered to make the big choices in life. Because almost everything, all external expectations, all pride, fear of embarrassment and failure, all these things just fall way in the face of death. Remembering you’re going to die, is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. there is no reason not to follow your heart.”
    • (10.04 mins) He shares his alarming discovery of pancreatic cancer.
    • (11.40 mins) “No one wants to die. Even people who want to go to heaven don’t want to die to get there.”
    • (11.58 mins) “Death is very likely the single best invention of life. It’s life’s change agent.”
    • (12.18 mins) “Your time is limited. Don’t waste it living someone else’s life. Don’t be trapped by dogma.”
    • (12.34 mins) “Have the courage to follow you heart and your intuition. They somehow already know what you truly want to become. Everything else is secondary.”
    • (12.51 mins) Steve talks about “an amazing publication called the whole earth catalogue”.
    • (14.00 mins) When the publication had run its course they published the last issue. On the back cover was a photograph of an early morning country road with the following words beneath it “Stay hungry stay foolish.”
    • (14.12 mins) He ends his speech with those words as his advice to the Stanford graduates. “Stay Hungry. Stay Foolish”

Busting out of the Cocoon

Galvanised by Steve Jobs’ moving speech, I resolved to live mindfully and deliberately in each moment.

Over the next few months of practising mindfulness, I gradually realised that most of my present moments were spent doing stuff I wasn’t passionate about.

Though my 15 years in the corporate world had taught me a lot, it had been all about chasing society’s dream — not mine. Working within the confines of a corporate hierarchy was insipid and mostly ineffective.

It was time to use what I’d learnt to make a more direct impact. I wanted to really make a positive impact in the business world — not follow standard operating procedures.

I didn’t want to build complex models in excel spreadsheets that were brandished like weapons in thinly veiled political power plays.

I recognised my time here was limited! I needed to get started … now!

So I started a blog on productivity — something I was truly passionate about.

My readers liked several of the posts and started to see me as a productivity expert. I got approached by friends to learn how to use Siri on the iPhone to save an hour a week.

I discovered that I loved teaching and sharing knowledge. I loved making a difference to their lives. 

This led to my decision to become an entrepreneur. I’ve never been happier.

Looking back, there are several valuable lessons that I learnt when I decided to live my life in the ‘face of death’.  I gained quite a few valuable insights on dealing with change which I apply to my life as often as possible.

My mindfulness practice has helped a lot with this too.

Blindness to Change – Harvard Case Study

We are surprisingly inattentive to change happening around us. Often before our very own eyes.

In 1998 Daniel J Simons et al from Harvard University and Kent State University conducted a study using motion picture cuts as visual disruption. In the experiment an actor came up to a pedestrian and asked for directions.

As the pedestrian provided directions, two people carrying a door passed between the actor and the pedestrian, temporarily blocking their view of each other.

During that time, another actor replaced the actor – a  completely different person. 50% of the pedestrians didn’t notice the substitution.

The experiment was one of the first to illustrate the phenomenon of “change blindness,” which shows just how selective we are about what we take in from any visual scene — and we rely on memory and pattern-recognition significantly more than we might think.

Our memories and expectations have a much higher influence on our perceptions than we realize. We react to our perception of events.

This applies to change too. When it comes to change we are often jumping at shadows. Paying full attention to the present moment goes a long way towards offsetting this tendency.

 22 Actionable Insights to Help You Thrive Through Change


  • Look in the mirror each morning (like Steve Jobs did daily for 33 years) and ask yourself “If today was the last day of my life would I want to do what I’m about to do today?” If the answer is yes too many times in a row, then you know you need to change something in your life. If you want to achieve true happiness, you need to recognise that life is fleeting and that achieving great things often is the result of living fully in each moment.

  • “Remembering you’re going to die, is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. there is no reason not to follow your heart” This quote from Steve Jobs is very useful for two reasons
    • By framing all events in the context of our inevitable death, change is put into a very useful perspective. Change is no longer as intimidating
    • It prioritises what you want to change in your life and what you don’t. This is what led to Steve achieving great things like pioneering an industry where personal computers were normalised.


  • Use mindfulness to become aware of the agent of constant change in your body : Your breath. Your breath is also a  barometer of your mind –  shallower breathing means your mind is disturbed and deep slow breathing means your mind is stable. Make a conscious effort to understand that change within and around you is as natural as your breath. Unless, you’re not a fan of breathing, this should help to create a receptive attitude to change. It's also a great way to build your self confidence.


  • Practice belly breathing. This is probably one of the quickest and most effective ways to ground yourself. When the external environment spirals out of control taking one deep breath that extends the belly is incredibly powerful. Try it now.


  • Understand that it’s your attitude to events that affects you — not the event itself. If you fear change or try and avoid it, you’re much more likely to suffer through the process. Be open to change and recognise it as a necessary part of life. Chasing money isn't the answer. No amount of money is going to help you when it comes to matters of the heart. Money is really a magnifier of what already exists (or doesn't exist) in your life. 


  • Revisit your ‘why’ each day. Understanding your purpose (your why) is essential to coping with change for two reasons.
    1. It helps you to decide on what changes to prioritise in your life. For Steve Jobs he learned the importance of understanding his why when he was lying in the operating room waiting for surgery.
    2. It helps to accept the changes in the context of the big picture. Understanding the context of change can work wonders in reframing experience and our relationship to events.


  • Be Prepared for change. By revisiting your ‘why’ regularly you’ve taken an important step towards preparing for change. Understanding your why should give you some insight into the roadblocks ahead. That helps with the predictable changes.


  • Recognize the signs preceding unexpected changes. You’ll be surprised what mindfulness can do to make you aware of things you would have otherwise ignored or missed completely. For instance, a heightened awareness that comes from a regular mindfulness practice can make you sensitive to changes in relationships long before things spiral out of control. This is one of the ways to achieve true inner happiness and is the source of so much wisdom. 


  • Ask yourself: “Will this matter in 5 years?” or “What’s the worst that could happen?”. I can’t tell you how many times I’ve saved myself several seconds of angst when I asked myself this question after missing a bus or train. Remember that true happiness lies in gaining perspective on your situation rather than constantly seeking to reach the pinnacle of success. You could be the richest man on earth, but even that is fleeting and no amount of money is going to create a great relationship with close family members. Not a meaningful one anyway. 


  • Approach life with an entrepreneurial mindset. This means you see opportunity where most people don’t. Facing a problem is often an opportunity to create a product that solves other people’s problems too. Many incredible products were born out of this mindset. The smartphone already existed before Apple entered the iPhone market. But it was their approach to the iPhone that redefined the smartphone industry. It probably led to the iPad — which redefined the tablet industry.


  • Recognize that every situation is because of a confluence of events and you control only a tiny part — yourself. I’m not trying to sound fatalistic but once you understand that you can only control a small part of reality (yourself) then you are less likely to take so much personal responsibility for bad outcomes. You still strive for goals … you just don’t attach yourself to the result.


  • See change as an opportunity. Steve Jobs embraced some very painful events with an attitude of openness. Like the entrepreneur he was he saw each event as an opportunity. This is critical to using change as fuel for your purpose.


  • Recognize that change is not linear. Expect to take two steps forward and one step back. Don’t expect ‘the dots’ to line up for you to connect them. If you feel you’re going in circles remind yourself that you’re going in spirals. You may revisit the same point in a process several times but YOU that revisits that point is changing each moment.


  • Become very aware of the language in your mental chatter. Listening carefully to the messages you’re giving yourself through your mental chatter is critical. Mindfulness is such a powerful practice because (amongst several other benefits) it makes you aware of your own thought patterns. It’s amazing how often you realize the messages you’re giving yourself originate in your childhood and are not true reflections of your abilities.


  • Realize that each moment presents you with a choice. While it’s true you are a product of your experiences, it is also true that you have a clear choice in each present moment. Use the present moment wisely. The present is your point of power. You can make a choice not to be influenced by your history.


  • Understand and internalize this fact: The past is not a predictor of your future. Just because that’s how you’ve always been doesn’t mean you can’t be something different at this moment. With conscious effort, you can make a choice to think completely differently.


  • Robin Sharma suggests that you try to do one scary thing each week. This is very useful for developing a sense of confidence. It also sets the tone for a more proactive attitude to change. By taking change (in the form of new situations) head on you are much less likely to feel intimidated by it.


  • Keep a diary or a journal and write in it every day. Something cathartic happens when you write. It takes you out of your head and slows down your thinking. It’s very therapeutic to see your thoughts down on paper or on a computer screen. This also allows you to look back through your history and see how you dealt with past changes.


  • Actively ‘mine’ for valuable insights. Deliberately trying to write down your insights from each day means you get the most learning out of each day. It grounds you and connects you to your why. I can’t recommend this practice highly enough.


  • Expect change to be gradual. In our consumerist society, we are very impatient with most things. We expect to see change happen overnight. Changing habits and mindsets is a process that requires repetition. A lot of it. Having unrealistic expectations will only frustrate you and slow you down.


  • Realize that fear of change is usually fear of the unknown. Recognize the fear. Feel it as sensations in your body. Then take action anyway.


  • Deal with change one moment at a time. Accepting change is a lot easier one moment at a time. Projecting too far into the future when it comes to accepting change is difficult and usually self-defeating.

“Life is a series of natural and spontaneous changes. Don’t resist them; that only creates sorrow. Let reality be reality. Let things flow naturally forward in whatever way they like.” — Lao Tzu

Change is at the fibre of all existence. To avoid change is to avoid reality.

The best way to deal with change is to proactively seek it out and embrace it. Fear of change is natural and almost inevitable. But acknowledging the fear and then moving forward anyway is at the heart of the human evolutionary process.

What’s your biggest challenge when it comes to change? How do you deal with it? I’d love to hear from you in the comments section below.

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Ash Roy

Ash Roy has spent over 15 years working in the corporate world as a financial and strategic analyst and advisor to large multinational banks and telecommunications companies. He suffered through a CPA in 1997 and completed it despite not liking it at all because he believed it was a valuable skill to have. He sacrificed his personality in the process. In 2004 he finished his MBA (Masters In Business Administration) from the Australian Graduate School of Management and loved it! He scored a distinction (average) and got his personality back too!