How Coaching Can Help You Cheat Death

Cheating Death


One of the most thought provoking questions I’ve received is whether I can help people cheat death.

Are you coaching people on how to cheat death?! If so, shut up and take my money.

Cheating death implies there is a grand design and order that predetermines the specific moment and manner in which you will die. The universe is far more subtle than that. It is not overly concerned with you and your sense of self. The universe doesn’t care if your ego lives or dies, if you are happy or suffering. But it does have an order to how it operates. Once you are on the final runway of life it would take a significant force to redirect your energy back to our reality and bring you back from the brink. Let’s call this a life force multiplier.

I do believe my transformational coaching can help you to harness that force. I believe I can assist you to understand the energies at play. When the time comes, you will know what to do to create your life force multiplier. You can then choose to ‘cheat’ death for a higher purpose.

Let’s use an example to delve deeper.

You are seen by your peers as a great leader who has already made it. But if at any point in your life you had taken the time to really stop and think about it, deep down you would know you could do better. But now it’s too late. You know you haven’t stepped up enough, and disappointment pervades your moment of death. You could’ve done more. You could’ve faced death satisfied you had done your best to make the world a better place. Instead you slip away surrounded by defeat and regret. This is a very confronting thought.

In that moment of death comes pure clarity and you know, without a doubt that you could have avoided that feeling of disappointment by:
* tackling your challenges head on,
* confronting your fear of the unknown,
* dealing with the complexities that surrounded you.

Had you stepped up earlier, embraced your greatness, done all you could and given your best, there are two possible outcomes at that moment of death:
1. You could move on to the next realm with a smile on your face. Sometimes it is a person’s time to go and c’est la vie; or
2. Whatever affliction or situation threatened to kill you, you could turn things around, fight it from the depth of your soul and make it back – your determination to continue your great work radically boosts your inner strength and your life force multiplier kicks in, you achieve flow and pull yourself back from the brink.

There have been numerous accounts of near death experiences in which people have come back filled with an overriding desire to make the world a better place. In my case I faced overwhelming odds, but as I recovered I knew with absolute certainty: I had done so to change the world.

I had done so to change the world.

How do you get to be in such a position where you have the inner strength to effectively ‘cheat’ death in order to achieve more?
This is not about your ego, your sense of self, or what defines you. You need to be working on things that totally resonate with you at your deepest level. You need to be totally focused on your soul work. And this is where my role as a transformational coach kicks in. We spend time finding what resonates with you and finding your purpose. We work through any blockages to you achieving your goals and then developing a plan of action. I am there for you on your journey as you execute on your goals. I have your back. I act as a sounding board and a trusted advisor, because your board of directors is not there for you in this capacity.

Where are you positioned on the Life Purpose Spectrum?
How purposefully you live your live can be measured on a continuum. We can call this the Life Purpose Spectrum.

If you are placed at the far left of this spectrum your life has no purpose. Perhaps at some point you felt it did, but your priorities have shifted. A common example is that you realize your role leading your organization no longer resonates with you.

If you are placed on the opposite end of the continuum, the far right of the spectrum, your life is filled with purpose. To continue the above example, you may have found your purpose again by transforming your organization, changing its business model to be more relevant to a more engaged customer ecosystem. Or you may have moved on to another organization that better reflects what you find important in life.

Take a moment and ask yourself,

“Where do I sit on the spectrum?”

Write your answer down.

Now think about people who participate in death-defying activities. Your first thought is probably that they are off the continuum, that they are at the far, far right of the spectrum. That may well be the case, but it is their mindset that I want to highlight. Their mindset is instructive for you as a leader as you think deeper about where you truly sit on the Life Purpose Spectrum.

Consider Loic Jean-Albert. He is a proximity flier. That means he dons a $2500 wing suit and jumps off mountains. After an initial free fall of a few hundred meters to achieve optimal acceleration speed, his suit inflates. He then hurtles downwards at a speed of more than 50 meters a second. The smallest error can be catastrophic. He has had a lot of friends die – he isn’t playing golf.

But for him it is life, it is living – in a Newsweek article he says that he watched his grandmother die of cancer in bed and he found that horrific.

“I can’t imagine anything worse. What is important is how you live. Death is inevitable. I don’t care how or where I die. Those details are not relevant. And who knows, death might just be one of the most beautiful things that we get to experience.”

For him it is all about purpose. If he is following his true purpose then whether he lives or dies is neither here nor there.

“We are evolving, through technology and through skill. I liken what we’re doing in proximity flying to the first animals that left the water. We are evolving and growing. And becoming stronger. What else is the purpose of life?”

Another proximity flier, Ellen Brennan, points out that for her it is all a question of what you want from your life.

“Do you want to go work your ass off, never get out of that hole and exist knowing that this is all that you’ll ever have, apart from maybe two week’s vacation in Florida every summer? Because that’s not what I want. I want to do things that people tell me I can’t do. And that domestic grind, to me, is not life. I want to live.”

Now ask yourself again,

“Where do I sit on the spectrum?”

Write your answer down. Does it differ from your initial answer? If you are truthful to your inner soul and find yourself further left on the spectrum than you initially thought, you’ve got some work to do.


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Should You Become an Angel or Venture Capitalist? Transitioning from Operational Executive to Portfolio Player


Leading executives can become totally focused on their operational role. Yet at some point, a trigger results in them losing their mojo for working in one business. What type of role is better suited to their next phase in life?

I posit that it is a meaningful transition for them to coach entrepreneurs and manage a portfolio of startup investments.

I’d like to illustrate my hypothesis by exploring two case studies.

Finding His Creative Mojo: From Ad Agency to Angel

David is a successful CEO of a world leading advertising agency. He has been focused for the last 12 years on growing the business, its reputation and its people. When he first approached me he felt that something wasn’t quite right. he had used an executive coach for many years, so understood the paradigm. Yet he realized that he needed to work more with a transformational coach. A coach who not only understood the business landscape, but also had firsthand knowledge and understanding of and empathy with people going through a transformational journey.

He loved to sing in the shower, especially on mornings before a big pitch, or when he was traveling on business. But he found himself no longer singing. This was the initial signpost for him to realize that it was time for him to go on a different journey. Many people ignore these early warning signals until it’s too late for them to change.

We spent our initial time together exploring what had excited him before. We delved into what areas he most feared. We explored if there were deep, unresolved issues that could stand in the way of him making a transformational shift. It is always best to work through such issues in the early phases of a transformation. They may cause blockages in your ability to perform. They could also act as blinkers to you discovering what you find purposeful.

We started the process of getting him to hear his inner voice. It had been suppressed for many years by his ego. This voice is always there in every one of us. We may suppress it to the point were it is so faint that we cannot hear it. What we were looking for from his inner voice was a deeper understanding of what resonated for David. What was his true soul work? In his 20s, he had worked with some start up companies on their market positioning. He had also been active in creating a technology spin out from his advertising agency.

He came to the realization that it was time for him to move on from running the operational, day-to-day side of his agency. It was time for him to get back into the world of creating. At his core he was a creative, which is why he had been so successful in the advertising arena. In particular, though, it was time for David to move deeper into the world of startups. Meaning and purpose for him was about building companies that were making a difference in the world.

This was never going to be a binary process, with him being an operational executive one day and a startup portfolio player the next. We had set that expectation early on. He knew it was a significant journey. It would have many moments: some positive, some negative.

A thought leadership position can benefit the move from operational CEO to Non Executive Chairman. David had no interest in writing books, but was keen to do outreach activities. He joined the board of a not-for-profit organization in the medical health arena. He was invited to be be a regular on a well-known, news-related television show. This significantly raised his profile. He took two further board seats of large companies. This positioning helped him make the mindset shift from single focus to portfolio player. It also ensured the right circles noticed when he made the announcement of his transition to Chairman and startups.

The next transition activity was a robust succession plan within the advertising agency. He identified two executives who had the skill set, drive and passion to step up into joint CEO roles. They were both positive about taking over the operational aspects of the agency. They began working with executive coaches to assist them in this process. David also began the discussion with his Chairman about his decision. They mapped out a plan for him to transition into the role of Non Executive Chairman within 24 months. The Chairman volunteered to take a less active board role.

We then began exploring the role that David should play within the start up space. He didn’t want to take on a CEO or other operational role in any one company. Instead he wanted to build a portfolio, working closely with startup CEOs as a coach. He wanted to ask the hard questions. He wanted to accelerate their growth and keep them on track as they scaled up. He preference was to invest into these companies, rather than consult to them. Their upside would be his upside.

He was comfortable working as an independent agent, as a lone wolf. Although he could see the benefit of teaming up with other investors when it made sense. He was suited to becoming an angel investor. He had significant net wealth at that point. His financial investment portfolio was diversified and included properties and blue-chip stocks. He could afford to allocate a few million dollars towards his initial startup portfolio. He was also of the mind that this was risk capital. He wanted to deploy his capital into companies taking bigger risks that had above average goals. He was mentally prepared for the fact that he may not receive a positive return on investment from this activity. It was to be a learning experience.

We worked closely on how to place him within the entrepreneurial ecosystem. He began to get a feel for how he could determine whether a startup was worth looking at closer. He crystallized his Investment Charter. This set out his strategy for the kinds of companies, types of technologies, geographical preferences, stages of development and many other factors that assisted him make investment decisions. The aim was to ensure he was targeting the right kinds of businesses that could deliver him significant return on investment.

As he started doing meetings and due diligence on potential investee companies, we continued with his education in this area. The aim was to make sure that he was not making emotional investment decisions. It was also to ensure that he was able to draw on his significant business experience. He became comfortable that he could add significant value to the companies that he chose to invest in. He wasn’t keen to join a formal angel group. Nor did he want to become part of the herd that chased investments at pitch competitions.

Some of the companies that he was targeting already had angels circling them. In some cases he had a meeting of the minds with these investors. This was one way he was able to start growing a network of angels he was comfortable to invest with. He also reached out to senior executives were either already active, or wanted to get active, as angel investors. Within a matter of months he had four different informal networks that he was teaming up with.

David went on a three year journey from operational CEO to having a portfolio of board seats and angel investments. He has not only found his inner voice but is also singing in the shower again.

Adventure Capital: A Venture Guy’s Journey

Tom was the CEO of a large communications service provider. He had been in this role for six years, having worked his way there from inside the organization.

Similar to David, he reached a point where he no longer saw colors. Tom’s world became black and white. He approached me with the realization that he needed to make some significant changes in his life. He had worked with an executive coach for a number of years and so understood the power of coaching.

He wanted to explore how best he could get excitement back into his life. He had also become enamored with the entrepreneurial fervor that was sweeping the world. He initially sat on the investment committee of his company’s corporate venture capital group. He found that he enjoyed spending time with their investee companies.

His company had already created a succession plan and there was no need for us to revisit that. He was also well known in the business arena. He had a high profile thought leadership position that we could leverage. We could move forward at a fast pace.

Tom decided to make a clean break from his company. We explored the best positioning for him within the entrepreneurial ecosystem. He didn’t want to operate as a lone wolf. He was more comfortable being part of a formal group that had significant track record and a brand name. He preferred to work with a group of partners from whom he could learn the ropes.

Through his corporate venture capital exposure he realized that he didn’t want to work with very early stage companies. He found this time in a company’s development frustrating. He was well suited to work with companies that had already reached product market fit and were experiencing rocket ship growth. For example, startup companies that were about to receive a significant Series A investment.

It became evident that the best place for him to play would be as a partner in a venture capital firm. He had discussions with venture firms that his company had done deals with. He got on well with some partners of these firms. He started receiving offers from VC firms. He chose to join a well-known firm. They were raising a new fund. This meant he could both participate as a limited partner in the fund and as one of the general partners deploying the capital they raised.

I continue to coach him in his position as a VC. There are many VC nuances he is finding a deeper understanding of – for example,

* the healthy tension between being an individual VC and a partner within a partnership;

* the potential for conflict between a venture guy and their investment companies.

* how best to coach portfolio CEOs – what kinds of questions he should be asking, what signs he should be looking for that they are on target and on track both operationally and emotionally.

Both David and Tom have not only stepped up through their transformations. They have also proven the power of having a virtuous circle by referring some of their portfolio CEOs to me and some of their former colleagues have also expressed interest in coaching.


1. Be aware of trigger signs that a transition is imminent. You may miss the signs and find yourself in a trough – it is significantly harder to catalyse a transformation the deeper you fall into a trough. Heeding the signs earlier is better. This ensures there is no urgency to your transformation journey.

2. Be prepared for significant change. Transformation is never linear and this organic journey may take you places you didn’t initially imagine. Go with that flow.

3. Be prepared to listen to your inner voice. You may have a tussle with your ego not wanting to let go. Eventually your inner voice will win out.

4. The world of startups is not for everyone. Nor is being an entrepreneurial investor. Go there for the right reasons – it resonates deeply with you, you enjoy creativity, you have the right risk appetite and profile. Don’t go there because you’ve read in a business or in-flight magazine how hot startups are or how much money you could make in the space.

5. Don’t burn bridges. Once you’ve made your mind up to transition, do so gracefully. Ensure the right succession plan is in place. Leverage your current position to create your thought leadership position. This will ensure you optimize your transformation trajectory. You already have a solid network in place, they want to help.

[Note: Names and situations have been altered for confidentiality reasons]


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#ComeAlive: Turning world peace into an irresistible business opportunity

World Peace


EXOscalr, the world leading transformational coaching and advisory business, has announced the recipient of its inaugural #ComeAlive Scholarship.

Melbourne-based RMIT student Bridget Dunne was selected from amongst a strong group of contenders for the scholarship which is worth US$120,000. She will now take part in the #ComeAlive Program, a 12-month, quest-driven coaching program designed to trigger and support clients on their quest journey.

Rand Leeb-du Toit, Chair & CEO of EXOscalr, says that she was picked on the basis of a range of criteria related to each applicant’s quest.

“We were looking for three things: the quest needed to be high on impact, it needed to be aligned with their passion, as opposed to their ego and while it doesn’t have to be completed within the 12 month program, realistic progress should be made during that time.”

“Bridget’s quest is to change the world through turning world peace into a marketable and irresistible business opportunity. This aligns well with EXOscalr’s moonshot goal of positively impacting the lives of 2 billion people by 2025.”

“When I look into the future, I see a different world, a better world, and I want to be part of making that happen,” says Bridget Dunne. She is looking forward to the accountability, discipline and guidance that the #ComeAlive Program offers.

“The world needs more people focusing on making massive difference. Yet embarking on such a quest can be a daunting experience. ComeAlive is designed to provide those pursuing such important endeavours with a high level of encouragement and support”, said Mr. Leeb-du Toit.

“We created the ComeAlive Scholarship with a view to encouraging people to take a deeper look at how they can make the world a better place, while they are still in their formative years, before the stuff of life gets in the way.”

EXOscalr is a transformational coaching and advisory business that works with high achievers and influential leaders, coaching them from great to extraordinarily great.


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6 Hacks for Gaining High Achiever & Elite Performer Status

StepUpThe media loves to trumpet overnight success, but there is always a back story of blood, sweat and tears. The journey from amateur to professional and the path to elite performer can be daunting. How can you ensure you succeed in your quest for success? We provide six hacks you can use to gain elite performer status and become a high achiever.

1. Set a guiding principle and just start

As daunting as your quest may seem, you need to take the first step or you will never get closer to your destination. You may not have mapped out the entire journey. You may not know exactly where your quest is taking you.

But just start.

Take one small step forward, and then another.

Before you know it, you will have established something unique that the world has never seen.

As you start on your quest, ask yourself a transformational question. This will become your guiding principle.

It will kick start your passion and give you the impetus to take that first step.

For Odysseus the question was, ‘where is true home?’

     What is your transformational question?

2. Aim for regular milestones, achievable annually

There are no overnight successes. Nor will the answers to your transformational question just arrive out of the blue. It will take hard work, long hours and persistence.

Your focus is on answering that big question, on achieving your goal. Yet many things can intervene and sway you off course. To ensure you remain in pursuit of your goal set some smaller milestones you can achieve each year.

Every year you want there to be two to three things you feel you’ve made progress in. This prevents you from getting stuck. Some years will be better than others. By constantly moving yourself forward you will smooth out the years. You will come to view yourself as a success. This will give you the motivation to continue on your quest.

Doing this year in, year out will lead to some big wins. That’s when you will be referred to as an overnight success. At that point smile and nod, knowing that it was the little things, the small milestones that got you there.

     What is your first milestone?

3. Understand the levels of competence and timing in your industry

Each industry sets expectations of how long it takes to become an elite performer. Form an understanding of what these time lines are.

In most professions or crafts there are three levels of competence: beginner, intermediate and advanced.

What can you expect to achieve in each of these phases?

Beginner – you will be parroting the insights of your influencers. Success in this phase is being able to produce a body of work that isn’t an embarrassment.

Intermediate – you will have a clearer idea of what you are doing. You may feel you’ve changed direction and wasted time. But you are always building on your experience and adding to your skill set.

Advanced – your unique voice will emerge in this phase and you will produce work that has not been seen before.

     Are you prepared for the long haul?

4. Step up from performer to elite performer

Stepping up to the ranks of elite performer requires a psychological shift. This needs to be a threefold shift in you:

1. You need to come across as being relaxed. You don’t have to prove yourself anymore and you don’t want to come across as trying too hard.

2. You need to be deliberate with the things you are saying and doing.

3. You need to belong. You need to be within a space that you own. You need to feel that you are entitled to be there.

You also need to catalyse a psychological shift amongst those you engage with. They need to see that you’re not just trying things out, but you have a reason to be there. They will then take you more seriously.

At this point you’ve achieved a foundational shift. But to truly step up you need to be developing your own material. You need to come up with your own compelling thinking. You may still rely on your old influencers, but you need to be exploring new territory.

Find your authentic and unique voice. Think of yourself as a force.

     Do you aspire to be a great master, to hold the universe in your palm?

5. Avoid the ruts, never feel secure

This is a long-haul. There is a possibility that you don’t push yourself enough. If this happens you will dig a deeper and deeper rut over time. You’ll need to create a breaking point and find your raw groove again.

Keep revisiting your transformational question. Check that you remain in hot pursuit of the answer. You should not feel 100% secure. If you are not somewhat scared, you will become complacent. Your inspiration will wane.

     Is the fear always there?

6. Lift your game and focus

“Nothing contributes so much to tranquillising the mind as a steady purpose – a point on which the soul may fix its intellectual eye.” – Mary Shelley

This quote sums up the point that if you want to operate at a higher level, you need to lift your game and bring focus.

There are three ways you can do this:

1. Whittle away the things that you don’t need.

2. Create a solid core of who you are both as a person and as an elite performer.

3. Become aware of your compulsions and the rabbit holes that you could scurry down. Initially you may meet these urges. You will need to leave them behind to elevate yourself to the next level.

     What do you fundamentally believe, as a person, is important?

About EXOscalr

We coach for difference. Our clients are influential leaders, high achievers and outliers. Interested in an initial session? Sign up here.

Six Ways to Fast Track Yourself to Rocket Ship Performance

Are you

Most people are comfortable going through life at a steady pace. High achievers put themselves onto a steeper trajectory.

How can you break orbit, fast-tracking yourself to the higher-altitude terrain of elite performance?

Here are six ways to step-change your performance levels.

1. Actively engage – be a rocket ship, not an altimeter
An altimeter reacts to its environment, measuring altitude. A rocket ship takes you on a journey to new altitudes. Influential leaders fly rocket ships. They become actively engaged in their journey. They do not leave everything to chance. They decide they want to change and they actively engage in doing so.

2. Form powerful and positive meta-beliefs
Success is not only about tactics, but also about mindset. Listen to your self talk. Is it your worst critic? Does it constantly engage in negative thought patterns?

Your mind eavesdrops on your self talk and it becomes a predictor of performance. If it constantly says that you won’t achieve a particular goal, there is a very high probability that you won’t achieve that goal. Shift your meta-thinking, your thoughts about who you are. Visualise yourself on a higher level. Create the right-thinking patterns to get you there.

3. What you put in, is what you get out
High-performance requires the right inputs. There are four areas within which you can optimise your input levels – diet, oxygen, exercise and sleep.

Diet – Make sure you’re getting the right level of nutrients out of your diet. Fresh local produce is what you should be eating, together with lots of water.

Oxygen – Breathe deeply to optimise your oxygen intake. Your brain uses up to a quarter of the nutrients and oxygen you take in.

Exercise – The more physically active you are, the more focus you will have. Consider as a rule of thumb that anything that is good for your heart is also good for your head.

Sleep – Sleep more. You don’t build muscle by working out, but by resting

4. Manage your stress
The more stressed you are, the more time you spend in fight or flight mode. This state is not conducive to curating information and reflection. Manage your stress better and you will make more measured and informed decisions. This is essential for elite performance leadership.

5. Learn constantly
Stimulate your brain constantly by learning new things. Mix up your learning by focusing not only on your domain of expertise, but also orthogonally. Cross-fertilisation can lead to powerful insights. Our brains thrive on new connections. Use writing as a way to crystallise your thoughts and achieve pattern recognition. Many high achievers write daily.

6. Peer yourself positively
Your social networks determine how smart you are. There is a lot of truth to the saying, who you spend time with, is who you become. Make sure to spend time with people that challenge and encourage you and from whom you can learn.

What can you do today to fast track your performance?
Look at these six areas and determine which ones you are neglecting.

What can you do today to improve on each of these?

Ask yourself active questions to monitor your progress. For example, have I done my best today to manage my stress levels?

About EXOscalr
We coach for rocket ship performance. Our clients are influential leaders, high achievers and outliers. Interested in an initial session? Sign up here.


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The delicate balance of transformation

Be ready to transform but do not provoke, illuminate the darkness of ignorance but do not blind.

This quote from Tao Te Ching highlights the delicate balance of transformation and coaching for transformation.

Are you ready to #comealive?