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What should I do with my Life?

Case Study - What should I do with my life? 

Case Study - What Should I do with my Life?

This case study illustrates how my life coaching can sometimes be a deep journey into the self and what it means to be alive. My coaching is always a delicate balance of spiritual discourse and movement towards real-world action. Perhaps some of the ideas I offer here can stimulate your own inquiry into the potent "What should I do with my life?" question.

As a Life Coach. I want the people I've touched to become better with themselves. Not because of me, but because of them. Because of the intimate experience of two people sitting down and working deeply together to answer life's biggest questions.

Jason settled into our initial coaching session. Within minutes his distress at life became palpable to me. His desperation at the bleak-place that he found himself meant that he quickly opened up to me. He had become desiccated in his own efforts of self-discovery. Spilling the beans in a splurge of great honesty.

"Some days I'm fine. I muddle along through the admin of life, I feel busyish, and the day passes without an onset of any dark feelings. It's as if the needs of basic life-management, blocks out the desolate feelings that accompany being so lost in life. And then several days a week, I call them wretched duvet days, I become paralysed with a self-loathing. Everybody else seems to have their shit together. Why is it that I haven't got a clue about what I should do with my life? I'm a smart, capable, pro-active man. I'm prepared to do what it takes to find my way. But for the past five years, ever since I was made redundant, I have been caught in a weekly cycle of dread. Especially Monday mornings, oh Man, when I know everybody else is off to be productive. I plummet. What can I do with my life, Lee? How can I make a difference? How can I matter? How am I supposed to apply my best-self to solving this problem, when I feel so WRETCHED? Life, what do you want from me? Give me a break won't you. At the very least let me feel zingy, vital and powerful, so that I can solve this problem. I have never felt so low, so cut-off, so useless. I don't want to waste these precious years of my life."

Over the past 16 years of working as a Life Coach, this sort of challenge is one that I have heard many times. I have become a specialist in helping people find their way out of this debilitating what should I do with my life-pickle. Life journey work generally has three phases: Awareness, Planning and Execution.


Over the next several weeks our dialogues focussed on Awareness. My objective was to support him to capture a tangible snapshot of his self-observation. I wanted Jason to become very self-aware. Aware of all the good stuff and all the negative chatter that would almost certainly fog any progress out of this space. It is important to write this stuff down, to pull it out of the foggy-chatter.

What should I do with my life? Is one of those fundamental questions THAT WE SHOULD ALL STOP AND ASK OURSELVES. Although Jason wanted to make a pathology out of his life-situation. I encouraged him to see what a masterful Earthling he really was. At least he was taking the time TO RECOGNISE THE NEED to ask that question. To then take the time to deeply explore the space and then seek to answer the question. The crappy-feelings that arrive when we don't know what to do with our lives are all too common. They are a major malaise of our culture. Do you know anybody wrestling with this question?

Life is short, and it is masterful to live each day with a self-chosen sense of how we are walking the path. It is up to us to bring our own meaning to our life. But if we are seeking to answer the question, what should I do with my life? We should also develop an understanding of WHERE DO WE DERIVE GUIDANCE FROM to determine what to do with our life? What is the source of our own life-navigation if you will? I love exploring the answer to that question with clients.

"Lee I'm really caught in a desperate struggle of trying to answer this question. I'm hiding under the duvet; my life is passing me by. Some days are easy. Some days I wake up and my mission is just to distract myself for the day -- to get to the other end of the day without sliding into a depression. And frankly some days I don't give a shit. But when I get honest with myself, I am aching and craving for connected productivity."


In one of our awareness sessions we started to explore Jason's relationship to being "normal". Was he just trying to be average, to look like he's holding it together, rather like everybody else? Or was he looking for something beyond the normal. This line of inquiry was provocative. Be normal? Be beyond normal? Be at odds with doing nothing? Be at ease doing nothing?


As we started to go in with an observational scalpel, I invited Jason to notice his conditioning. To explore how his conditioning was creating the angst and confusion within. What societal and cultural influences was he taking on board? What external dictates was he believing as being pre-requisite for being a stable, able human being. What BS was he buying into? How was his conditioned way of playing the game of life hiding his real purpose?


I started to realise that what he was describing as confusion was his curiosity in disguise. I invited Jason to indulge in his curiosity, explore, vigilantly look inside. That isn't confusion, its simply in an inbuilt faculty that is designed to connect us with our innermost navigation system. It was that navigation system that could show him the way forward.

When we become curious, we can start to notice our self-sabotaging mind-chatter, the thought processes against the self. I'm broken, I'm not good enough, I'm useless etc.

This discourse then leads us to the importance of self-love as a foundation for being able to answer the big question.

Self Love

In almost every coaching relationship I explore the practice of self-love. Sure enough with Jason we arrived at the Mother Lode... Happiness starts when YOU LOVE YOURSELF. Self-love is the foundation that is required before we can start to answer the question "What should I do with my life?". Jason first needed to answer the question HOW CAN I LOVE MYSELF? If Jason were to be very Self-ish, how could he love himself? By being Self-ish, he will have lots of surplus to give. When we have surplus, we can influence and change the lives of people around us.

Self Love has many dimensions. One important dimension is to answer the question Why am I here? You didn't choose to show up. You are a Unique person. The Universe brought you here for a reason. Find that reason. Be that reason. Our coaching work seeks to reveal and clarify that reason.

"I want my life to matter. Despite my temporal impermanence. Despite the magnitude of my cosmic insignificance. I want to share life. To be life. To watch the way the sun and Earth request a kiss at night. To talk about this moment over coffee with a friend." -poem*

Look at the Reflections

The awareness and observation phase of coaching is very important. In this phase, my objective is to cause the client to bust themselves out of their normalised way of looking at life. Sooner or later though, the forensic work yields towards ACTION.

I know that when Jason actions some tiny-footsteps towards the mountain, he will eventually conquer the mountain. I gave Jason an assignment.

Connect with People

Go out and meet 42 people. Explore your network, friends, colleagues, meet-up groups, conferences, clubs, societies, lectures. Contact people, buy them a coffee and go talk to them. Notice how they change the world, what drives them. What makes them tick (especially the apparently-happy ones). As you talk to and watch people, keep a journal. Notice what you want, notice what you don't want. If you don't have a network or don't know anybody. Simply go out and be a voyeur, watch people in action, ride a bus, visit a hospital, watch a market stall. See if you can figure out the difference that they are making to the world. Ask them what their vision is, notice their attitude, what mindset do they have?


Get inspired, watch people, read books, watch documentaries, get inspired. Your vision, your attitude, your mindset will determine how you will behave.

If you have a felt sense of making a difference, then you have purpose. I have written about how to discover your life purpose here.

Jason managed to meet 6 people over the next few weeks. It was a good start.

I invited Jason to ponder the question, "What need, or problem would you like to solve?" Be inquisitive, just for the sake of it. There will be something.

In my truth we are here to understand the fundamental of what we are here for. In some ways that IS the purpose of your life – to get to know yourself.

In one session, Jason started to push back, so I decided to open a different line of enquiry… If you haven't got a clue what to do with your life, then go out and do what makes you happy. If you fancy the extreme-sport version of finding out what to do with your life, then … Be present. Ask yourself, what purpose is there here for me to do in this present moment? It could be watering your indoor plant, it could be starting to write a book, it could be volunteering or planning a trip.

Whatever you come up with do not take the path of least resistance is back under the duvet, towards an addiction, or back to porn. For the male readers who have made it this far, although porn can instil yummy feelings, it will rot your life to the core. Spurting over digital images of naked girls is not what you are here for.

Create Yourself -- Practically and Spiritually

Shortly after 9/11 I had a life crisis of my own. I really wasn't sure how to continue my onward journey. 20 years of being a tech-entrepreneur had become derailed by the popping of the Dotcom tech bubble. 9/11 rocked me to my core, not because of my family connections to the USA, but because of my humanity. Around that time, I also read a UN report on the State of the Planet Earth. Climate change, droughts, dead fisheries, parched forests etc.

The facts punched me to my core. I felt sad, depressed, powerless. I started a journey to find out what difference I could make. A teacher told me to go and meditate/contemplate the statement.

What would you have me do?

The answer... Why do people cry? I want to know why people cry. I know how to smile, I want to teach them how to smile. I then went and watched the sun rise. It worked. Great Life Coach, the what I should do with my life, was born.

Much of my coaching work explores polarities. As we develop a coaching relationship, I like to use each session to lay a few bricks. We can eventually build the cathedral. My work with Jason shifted gears to explore the practical with the spiritual. The what would you have me do question provided an opportunity to lay a few more bricks.

I invited Jason to spend some time meditating with the statement What would you have me do? To see if this beautiful line of enquiry would yield some subtle navigational answers.

If you are wrestling or dancing with the question, what should I do with my life, you too may like to follow this kind of questioning.

Over a period of several sessions, Jason and I captured a great deal of collateral material (bricks) that would allow us to identify some possible ways forwards. We eventually became ready to take the first footsteps on the journey.


"Soul-searing heart-scorching beauty. Failure. Success. Triumph. Defeat. Persistence. Defiance. Resilience. Repeat…" -Poem*

As a life coach, I am passionate about moving people into action. Unlike therapy, counselling or the other word-arts, coaching is about fostering tangible change. I know that if I can get a client to start to move towards their chosen mountain, then they have a far better chance of climbing their mountain. But Jason question of what he should do with his life, was a big one. He was a smart capable man but hadn't solved the question by himself. The awareness process in our coaching took some time. It was time for Jason to leave his uncomfortable comfort zone.

Right Now

Creating change that is born of the What should I do with my life question ultimately gives us a guidance for what to do right now. It wasn't about mapping out Jason's whole life. It was about getting to walk forwards with a clear sense of direction. The answers are rarely a whole-life guidance.

"We are learning. Day by day. I want to feel the time go by. I want to know that I have lived and be exhausted when I die." - Poem*

Where our attention goes, our energy flows. Whatever we focus on increases.

I had to move Jason out of surviving-mentality into thriving-mentality. If I could also get him to have a tangible sense of helping others, then I knew we could be onto a winning path.

I outlined to Jason a basic game plan -- start the journey, then evolve the journey. While on that journey, be honest. Notice what feels good, notice what feels repellent. Then use that honesty to tune up the path. I provided a support system constantly reminding him to use passion as his power-source to overcome problems. A significant part of my work as a coach is about connecting people to their passions.

When I first started working with Jason, I was working with a primitive desire. The desire to do something with his life! This desire was rather like the feeling of hunger, moving us towards getting some food. He had noticed the desire and reached for some help to get what he was looking for. Much of our work was in discovering the "what". I knew that as he moved into action, then he could actively fine tune and figure out the what, by actually doing it!

"Your beliefs become your thoughts,
Your thoughts become your words,
Your words become your actions,
Your actions become your habits,
Your habits become your values,
Your values become your destiny."
― Gandhi 

Your choices create your habits and habits become your life-journey. You are the product of your habits.


Over the past sixteen years I have been trusting my life-path of helping people as a Life Coach. I shared a lot of navigational detail of my own journey with Jason. I believe our job in life is to figure ourselves out. Ultimately we have to trust that life will look after us.

Ups and Downs on the path

I invited Jason to go forth without expectation of outcome and knowing that it would be OK to fail. As he started to take his tiny footsteps, he reported that some days continued to be bad. There aren't any quick fixes for life. It's OK to not-know. Embracing not-knowing creates purpose. The purpose becomes to know. The purpose becomes to find out… that's what do to with your life.

Jason got rolling with his onwards journey. He felt called to develop an idea in the Financial-Technology space. The path was full of entrepreneurial challenges, people challenges, and soul-searching. But he seemed to have tapped into a rich seam , that should keep him purposeful for at least a few years.

He called up one day telling me he was at a loss as to what to do next. We spent some time in silence. I invited him to "Feel the ancient breath of time on his skin and be free". We both started laughing.


Isn't it amazing that you could choose right now what to do with the next phase of your life. You can change it all right now if you choose to. 

At the end of your life-journey you will realise the treasure that you spent a lifetime searching for was always with you.

*This article contains excerpts of a poem that was sent to me. I do not know who wrote the poem. But deep bow to that lovely human being for sharing such elemental words. Thank you.

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Tuesday, 16 August 2022

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