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Find Your Why Journey Update #2

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I recently sent out a Wednesday Wisdom about a traumatic time I've experienced in my personal life and business.

When I shared this story, I invited my followers to come on a journey of introspection with me. I share the results from my first week of this experiment in this article.

Today, I sent out the final update. I recapped the ten questions we faced together, urged people to bring their thoughts to a conclusion and shared a summary of my experience.



In our first week, we tackled the following four questions: 

1. What's currently missing from your life?

2. When was the last time you felt fully alive? What were you doing?

3. What would your worst life look like? What would it involve? Why would you hate it?

4. What do you feel guilty about not having more time and space for? What is that guilt about?


This week, we made it an even 10:

5. What are your most important values? What lines do you refuse to cross, no matter the reward?

6. How are you currently living your values? How are you not? 

7. What really fires you up/ f**ks you off?

8. Who do you wish you could be? Why?

9. If you could start all over again, what choices would you have made differently? Which regrets would you erase, and which crossroads would send you in a different direction?

10.If you had no limitations whatsoever (time, skills, money, dependants, et al), what would you be doing? What would you do more of? What wouldn't you do at all? What would you do quite differently?


Your Challenge Today

Read back on what you've jotted down so far, adding extra things as you think of them, and catch up on any of the questions you've missed.

Then, challenge yourself with these prompts:

  • What opportunities do you have to move closer to the things you want?

  • What is inside your control?

  • What unhelpful stories fuel your fear or reticence, which you can challenge? Where do those come from? What can they be replaced with?

  • Who can you surround yourself with to shift those perspectives?

And most importantly of all...

  • Are you being kind and forgiving to yourself while you do this?

My Find Your Why Journey 

I wrote a brief summary of my first week's thoughts in this article. Here's an overview of the thoughts I added this week. 

Day Five - Values

I used one of the online tools I recommended, which came back with 5 key values:

  • Family
  • Freedom
  • Authenticity
  • Excitement
  • Growth

I spent some time thinking about those, and changed them to the following, which feel like a better representation:

  • Freedom
  • Fairness
  • Challenge
  • Contribution
  • Change.

I don't need to list family, that's my lifeblood. The rest are a better representation of what I truly value, even if I'm not living them as clearly and confidently as I want to.


Day Six: Alignment

This was a tough exercise that I spent a lot of time with.

The good:

Overall, I see lots of ways I walk the talk. I'm dedicated to work that demands authenticity and growth from myself and others. I actively push for freedom from norms that hold us back, and challenge structural and systemic conditions that lead to finger-pointing, victim-blaming and convenient myths of personal responsibility. 

I choose a life where I carry the risk, responsibility and reward of designing and delivering my own future, one which I can be proud of.

The bad:

I'm not doing all I want to be, to actively challenge and dismantle ideas that I'm aware of, and yet am still complicit in. I'm frustrated by the ways my distaste for pointless and harmful ideas, especially about work, rub up against profiting from that pathology. I feel guilty that I throw rocks while also benefiting from what isn't OK.

I also have a deep unease about the "inspirational" narrative that's resulted from starting to own and claim my story more publicly. I worry about reinforcing the misconception that the answer is more effort and better character from the marginalised, rather than paradigmatic shifts and structural change. I worry about the disconnect between my personal and political and often feel like a hypocrite.


Day Seven: Fury

I thought this would be a longer list, but my thoughts arranged themselves more neatly than I expected. The first thing I wrote, word for word, was:

"The audacity of privileged people, including myself, to disbelieve, correct or reframe the lived experience of others who are less fortunate."

I then got more specific, and added:

  • Gender inequality
  • Embedded and invisible classism
  • Child poverty
  • "Humour" and opinions that appropriate the trauma of others while claiming intellectual superiority 
  • Racism
  • Internalised misogyny. Internalised everything.
  • Fake allyship and performative wokeness
  • Toxic positivity
  • Lack of meaningful action
  • Bullsh*t work and the hope it will save us.

Day Eight: Aspiration

This was a curly and complicated one, as I found myself confronting my internal contradictions.

Part of me is about what I admire in others: I want to be more impactful, more activist, more forthright and less couched in the ways I spread ideas.

Another part of me wants to be more like what I resent in others: more privileged, safer, and freer.

Yet another wants to be what I've internalised I need to be: nicer, more loved, more attractive, et al.

All these things butt up uncomfortably against each other. It was useful  to see it all written down that way and begin to untangle the spaghetti.


Day Nine: Regrets

This was hard, and I felt myself holding back. Regrets are uncomfortable. They call your current reality, values and ideas into question and they feel... wrong? Naughty? 

The main themes were: times I've treated people badly, especially when I've hurt them or made them feel small. Times I didn't speak up.Times I've sacrificed my health, pleasure, dignity or values. Times I've been fuelled by fear of inadequacy or potential future loss. Times I've put work before joy and growth. Times I wanted to say no but didn't, or couldn't.

This quote hit me like a ton of bricks here:

"Recovery only comes when you actually do let go, when you get to a place of safety and can trust that there will be enough in the future - enough food, enough joy, enough love." - p.106 of "Sexual Revolution" by Laurie Penny.


Day Ten: Dreams

This one was even harder, which was surprising. I deal in dreams regularly, why did I find it so hard to access true freedom and imagination? 

I wrote that I would like to do more of: helping people who have no voice or choice. Writing more freely, and finding the potential in my creativity that I can sense I'm limiting.

I wrote that I would like to do less of: the labour and distraction of beauty. Consumerism. Work with clients I don't want to do. Guilt. Shame.

I feel like I need another go at that one, to be honest. It's incomplete.


Coming next

I'm going to sit with what I've produced, and answer the same recap questions that I posed to you at the beginning of this email. I can feel, very deeply, that there are a lot of things I can do to shift the dial, but that doing is probably not the answer.


To be very clear:

This was not an exercise to add more things to your plate to worry about or feel guilty for. It was to get clearer about what drives you, so you can start to explore and practise that in ways you feel good about.

I don't want you to write yourself a list of ways to be better. I don't want a list of potential tasks or projects to fail at.


Your final task:

The final thing I'm asking of myself, and of you, is to capture your overall sense of "why" into a short form you can use. Maybe a mantra or statement. Maybe a visual or diagram. Maybe a signifier or item that summons the energy you need or reminds you of what really matters.

Then, keep it around. Put it in your phone. Write it on a post-it note. Make it your background. I don't know, just... make it. Keep it there. Look at it regularly. Extract joy, strength and confidence from it. Don't feel the need to be something different, or do something more.

Just get acquainted with it. Make friends with it. Listen when it whispers to you. Ask it what it might need to grow and thrive. Roll it between your fingers and notice how it feels. Let it sit there, and expand or contract as it needs to.


Closing thoughts:

That's all you need to do for now. Finding your why is not a task you can tick off, but rather, a life's labour. A constant reevaluation. You've done a great job. If you've read this far, please accept a large burst of appreciation, warmth and pride directly from me and my tired, ink-stained fingers.

This is hard work, and work that many don't have the willingness, time, luxury or inclination to do. Well done for being someone who had the ability and drive to try. Whatever you've done was worth it.

Above all, thank you for coming on this journey with me.