WINSight // Finding Direction Through Uncertainty

WIN LDN’s New Year, New Heights: Life & Career Coaching Workshop with Caitlin Cockerton

In January 2022, we saw a shift away from unrealistic New Year resolutions to micro goals - small frequent targets plotted throughout the year. This disruption of the annual plan felt more manageable and attainable and instilled a certain optimism after the tumultuous years following the peak of the pandemic. But back then, we weren’t expecting to end the year locked in a state of ‘permacrisis’. 

The “instability” and “insecurity” that permeated 2022 reinforced the resilience and agility needed when working innovation. Women who had spent their careers battling against under representation in leadership and the lack of diverse perspectives in their work were now juggling shifting timelines with unpredictable futures. And when balancing this with the growing cost of living in the UK, finding that 2023 motivation wasn’t coming so easily.

This is where I found myself during ‘betwixtmas’ - trying to disconnect from the world and reconnect with myself - when inspiration struck during (another) Netflix binge. In one film, a therapist offered up his golden advice that he gives to all patients; “figure out what you want in life, and learn how to ask for it”. For a few days this felt like a lightbulb moment. So simple and obvious. But that light is quickly dimmed when you're left with the question, ‘But how do I figure out what I want?’

A powerful orientation towards the self

In January, WIN LDN hosted the aptly timed event; New Year, New Heights: Life & Career Coaching with Caitlin Cockerton. Dialling in from the French Alps, Caitlin Cockerton (PhD, MSc, CPCC), in partnership with WIN, delivered a virtual workshop - our very own ‘WIN Retreat’ - that put vision-setting into practice and created a space for all attendees to reflect, connect and paint a picture for the year ahead.

Caitlin guided us through the session with empathy, having spent over a decade in fast-paced business consulting in London, until she burnt out and rebuilt a more fulfilling and sustainable way to work and live. This led Caitlin to set-up Great Heights Pathways to deliver coaching with a mission to help people reconnect to themselves, one another and the world around us, in service of creating more meaning and deeper connection in the work we do and lives we lead. 

We started the session by physically looking back to reflect on the year. Using our breath to soothe our inner monologue and our bodies to pivot backwards, separating where we’ve been, from where we want to go. Applying this physicality allowed us to separate our cognitive thoughts from our physical feelings. We then asked ourselves, ‘What were we grateful for? What were the highs and the lows?’  We reconnected with where we came from, so that it could guide us to where we wanted to go. 

Separating your haves, wants and needs to find clarity

Now we were ready to start looking ahead and visualise our climb to the mountain top. In order to pinpoint our summit, we were asked to identify 3 ‘ways of being’ that we wanted to experience for ourselves; from being “less critical” to “more balanced”.  This pushed us to look inwards and consider what we wanted to experience next year. Rather than listing a set of goals we felt we “should” achieve, we personalised our vision by how we wanted to feel within ourselves.

Finally, we could build a map of milestones to help us navigate to our summit. To do this, we wrote a list of our ‘haves’, our ‘needs’ and our ‘wants’ - pulling them into separate columns. So often we conflate our needs with our wants, and our haves with our needs, and so by pulling them apart, you’re able to identify where you have gaps and to better understand what matters to you. 

As Caitlin took us through these visioning exercises for 2023, we learned through a series of breakout rooms that our attendees (established and experienced professionals) are broadly all keen for change; whether it be to slow down or to be more me-centric in their careers, or playful in their lives. It felt like a clear and renewed focus on self-preservation.

Embracing the guiding force of uncertainty 

In their 2023 Expert outlook, “The Age of Instinct”, Canvas8 explain that “in the tumult of 2023, we’ll see people act on their instincts to preserve their sanity, protect themselves, and safeguard what they care about”. They go on to feature Careers Expert and the Co-Founder of Amazing If, Sarah Ellis who believes that “we’ve seen a shift away from climbing ladders to navigating ‘squiggles’. Squiggly careers are characterised by change and uncertainty, by possibilities and personalisation.”

Working in innovation, we’ve spent a career trying to get comfortable with the unknown, and yet we struggle to accept that feeling when it comes to ourselves. But with “72% of individuals feeling more uncertain about their careers'' this uncomfortable feeling is familiar for most.

This uncertainty and discomfort is almost always clouded in shame or guilt. One attendee thought herself “lazy” having not found the motivation to apply for jobs despite being a new mum. As a woman, hearing that was incredibly sad, yet completely understood. Thankfully, another attendee stepped in to help reframe this narrative; it’s not your fault that you haven’t found a job worth applying for yet?! It’s not laziness, you’re embracing this time to find clarity.

That’s the beautiful thing about community, this conversation pulled us all towards a powerful realisation - that taking the time to feel is OK. And as Caitlin had explained, we had given ourselves, “the gift of time” to use this workshop to guide us through our feelings. Because without these moments, how do you know what you need to change? If the compass of our lives is how we feel, then our signals are the anxiety, fear, sadness, joy we experience. What I took away was that having these feelings isn’t the problem, but rather, not having the self-awareness to acknowledge them.

In order to plot a course to our summit, we have to identify what is worth climbing for. And it’s likely the answer isn’t something to go in search of, but instead something we already know but need to accept. So in those times of uncertainty, prioritise slowing down and looking inwards in order to be more honest with yourself and figure out what you want.

Once you’ve done that, all you need to do is “learn how to ask for it.”

Authored by: Meera Pathak, Head of Innovation at Canvas8 and WIN London Chapter Trustee.

Find out more about Caitlin’s work at Great Heights Pathways. Here, Caitlin offers 1:1 life & leadership coaching, team building and development experiences, company, leadership & personal growth retreats, and facilitates one-of-a-kind seasonal mountain retreats open to all.

If you’re interested in learning more, feel free to reach out to Cailtin at connect@greatheightspathways.com