A Path To Enduring Introspection

Tom Eldridge
5 min readNov 7, 2015

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In November 2014 , a year ago, I left my strategy role at LinkedIn to go it alone. As someone who by the very definition of their role is required to plan for brands, I had no plan of my own.

By own admission, I was paralysed by a future unwritten and which demanded a quick response. What did I want to do? What were my strengths? My weaknesses?

Without the answers to these questions it would be impossible to create a meaningful plan to guide the next chapter of my life.

The following is a set of principles and supporting framework that I adapted from smarter people then myself to get my out of the rut. This framework encourages you to examine your career within the broader context of your life and values.

What follows is a series of self-reflective exercises that can help those individuals on the first wobbly steps that comes from pursuing a new direction in life.

Be brutally honest with yourself

Unless you’re into self-flagellation, knowing what you suck at is probably the last thing someone should take onboard when considering a career change. Yet being searingly honest with what I was not good at, helped me put some hard edges to a future I wanted to have.

What do I suck at? A list of things I needed to improve on in November 2014

The first step was to understand the triggers behind my lack of confidence in my abilities and lack of grit. Unpacking some of the causes on the 2nd row allowed me to think how I could improve in these areas. The next row (in pink) was to have a clear set of actions in place to guide me.

I would recommend that while it’s important to go through this process of introspection by yourself, do get someone who knows you well and get their input.

Giving up a salary raised these concerns in November 2014

Addressing the very real possibility of not being able to pay the mortgage forced me to think how I could mitigate these issues.

Where do you spend meaningful time?

Pereto Law works on the basis of the 80:20 rule. Imagine you’re running a business, you will find that 80% of your business will come from 20% of your customers

The question I needed to understand was identifying where I needed to spend my time that will deliver real value in my life.

In this case I divided my time into three key areas. My family, my business, and my wellbeing. All are interdependent on the other and yet at the time were out of kilter with a life I wanted to have.

The goal here was to identify areas (in blue) in my where I could use my time more wisely and to put together some tangible actions (in white) against each one.

Input / Output

Related to where I spend my precious time, I looked long and hard at what my main inputs were. I divided them into two parts. Those things grouped under ‘Stock’ are the bedrock, the enduring ideas, people and principles that I believe add value to the way I live my life. ‘Flow’ items are what I would class as non essential in the sense that they are easily accessible but deliver only marginal value.

The enduring (stock) and the temporal (flow)

Having identified my inputs, the next step was to have a clear idea on what my output was.

My outputs it transpired were very intangible

By looking at my outputs I could see, at the time, that my work was at risk of being too theoretical and intangible. It forced me to think about how I could take my strategic thinking and start to create a more joined up approach that could be tested and iterated upon.

The Input / Output process of introspection allowed me to see objectively where I could develop my offering and to create meaningful actions to move me in the direction I wanted to go down.

Social Bindings

I’ve tended to drift in and out of relationships throughout my life depending on the choices available to me at the time. Knowing who I surrounded myself with and the time I spent with them was a good measure of the emotional investment I have with friends, family, and co-workers.

For each group of people in my life, I attempted to express the importance they have in my life. One of the aha moments doing this exercise was recognising I had neglected catching up with old and new friends. I made a promise to take the time out each month to catch up with new and old friends.

Introspective framework of development

I found the following framework to be rigid enough to create real and meaningful actions, but with enough flex to evaluate different facets of my life.

You may choose to skip or add sections depending on what suits you. However I would recommend you take the time and try the techniques I have highlighted as it imposes searching questions of your life.

If you are interested in diving deeper and broader into some of the exercises highlighted, a good place to start is from the smart mind of Ian Fitzpatrick over here, here, and here.

Another heavily influencing factor came from David Whyte’s Three Marriage: Reimagining, Work, Self and Relationship. Whyte examines how the three areas of our life are in constant balance with one another and that by strictly separating them from the other.

A final word, I do not see the techniques covered as a once in a lifetime activity to get someone out of a rut. Although it could be used in such a capacity. The real value, I believe, is to repeat the exercises every 12 months as this allows an individual enough time to implement the actions and to adjust, as required, every year.

Tom Eldridge is an independent Innovation Strategist whose clients have included LinkedIn, Sony Pictures Entertainment, and presently Vodafone.

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Tom Eldridge

Strategic Designer, Triathelete(ish), Mangler of words — For a peek behind the curtain I’m usually found at https://www.strategyxdesign.co.uk/