Get comfortable operating in the grey
Because that's where dreams are made.
Something happens when you make a decision to jump off the ladder you’ve been climbing for your entire career. People start looking at you weirdly, their reactions typically falling into one of two categories:
‘Have you lost your fucking mind?’ they say, unable to contain their surprise at your decision to throw it all away (whatever ‘it’ is)
‘That sounds…interesting’ they murmur while breaking eye contact and wondering if you have, indeed, lost your mind
I’ve experienced these types of responses twice in my career. First, when I left my literal dream job at beauty retailer Mecca to go all in on a business, and second, years later when I said goodbye to founder-life to go solo and create a work structure I couldn’t yet name. Both times, various friends and family were perplexed. Wrapping their heads around my choice to leave something well defined to do something undefined was difficult and many were understandably sceptical.
In moments of weakness, their questioning led to my questioning…
‘Should I have left the business I spent seven years co-building to consult and write and tinker and mentor and see what happens?’, I thought to myself while wondering if I had legitimately lost the plot. It didn’t help that I had nothing concrete to move onto. There was no bigger, brighter, shinier opportunity, and my only plan was a loose one to explore roles in venture capital or as Chief of Staff at a startup while writing on the side.
I felt lost operating in the space in-between; no longer a founder but also not not a founder. Still running a business, but just an enterprise of one. At the time I’d never heard the term ‘portfolio career’ and didn’t have a mental model to understand what I was creating let alone the ability to articulate it in a way that made others feel at ease. And so I fumbled along, trying to understand who I was becoming while drowning out the voices making me question where I was going.
It was a confusing time in my life, and it wasn’t until I did a values exercise and uncovered what’s truly important to me - independence, meaning, adventure, connection and financial security - that my fumbling turned into rumbling. My conviction grew and I realised that other people’s opinions were no longer my business, thank you very much.
Funnily enough it was right around this time that my enterprise of one took off. Clients landed. This newsletter gained traction. Months later I discovered the term ‘portfolio careers’ and something clicked. While the doubters still lurked in the shadows, I knew their whispers weren’t a reflection of my poor choices but a sign of me being ahead of the times. Their critiques were a natural byproduct of going against the grain.
Everything changed when I got comfortable operating in the grey. I learned how to sit still. I learned how to stand strong. I learned that the grey isn’t as muted and murky and hopeless as it seems. In fact, hidden within it is something that’ll make you lose your fucking mind.
A future of infinite colour.
🎙️How I use values to stay grounded even when the voices of sceptics ring in my ear:
Why it’s so easy to get disconnected from your values when you’re operating in the grey [0:46]
My first core value: independence, and why I thrive as a solo operator [2:31]
My second core value: meaning, and how I get this from writing [4:20]
My third core value: connection, the most important thing of all [5:20]
My fourth core value: adventure, something I need more of! [5:37]
My fifth core value: money and security, and how this informs how I manage cash and structure my income [6:10]
❤️🔥 Subscribe for more ideas and frameworks…
…to help you build a financially lucrative and creatively fulfilling portfolio career and life.
I say this every time but it is literally like you are in my head! In 2017 when I lost my passion for my corporate career, I remember standing in my kitchen and saying "I feel like I've climbed this ladder and turned around and realised I climbed the wrong one." It can be so destabilising and I felt lost for a long time. Finding people like yourself made me feel less alone on this wild ride of finding an intersection of career and meaning.
I renamed my newsletter to "Wandering the Grey" two years ago to explore this theme of forgoing an unconventional path after five years of engineering in Big Tech. The skepticism and the sneers you faced in your journey sound all too familiar. I created a little group with two other post-tech brave souls called "sabbadie hotline" where we share all the ups, the downs, the wins, the worries, but it's a very supportive group, and it helps having people who understand what you're going through. I wish you the best luck!
PS, I've written a lot about this stuff e.g.
1) Unshackling from golden handcuffs: https://www.tobiwrites.com/p/unshackling-myself-from-golden-handcuffs
2) How to design a sabbatical https://every.to/p/how-to-design-a-sabbatical
3) So you're a writer now?: https://www.tobiwrites.com/p/so-youre-a-writer-now