Stop waiting for permission to do your life's work

The only person who needs to give you the green light, is you.

A few weeks ago at an event, a young whipper-snapper asked me if I wished that I’d made any different choices over the last 10+ years of my career. Without drawing a breath I emphatically responded with “no, absolutely not!!”.

But as I walked home a few hours later I gave the question some more thought. I feel pretty stoked with where I’m at in life right now, but I certainly haven’t always felt this way, and if I really think about it, I’ve felt stuck and regretted my inability to make a change many times. More than I care to admit.

As I pounded the pavement and pondered, a series of memories started flashing before my eyes: there I was…in my last year of university after failing to fulfil my 23 year-long dream of becoming a spy. I shed tears reading the email that said, after ten months of doing interview after interview, test after test, I was not accepted and no, they would not provide an explanation for why. I remained lost for weeks, waiting for someone to tell me what to do next.

There I was…years later going all in on a business I’d started with two friends and then having the rather inconvenient realisation that I wanted to walk away. An impossible decision, I put it off for months because I believed someone else needed to give me a tick of approval to leave. Even though I knew, deep down, it was right.

There I was…a former-founder entering a new chapter of my career with eyes wide open but no destination in sight. Behind the wheel, but not really. Engine on, but idling in a yellow haze. Waiting for the light to turn green without realising that the person holding the switch was me.

There I was…rain pummelling the street below my apartment while I sat at my desk, listening to the deafening droplets shout at me to open my laptop, write, and share my words with the internet. Naturally, I chose to ignore this message. I was waiting for a real, legitimate, non-internet Writer to tell me I could write, I had permission to write, and therefore I should write.

That Writer never came.

There I was…turning my back on traditional work and contracting here, consulting there. I kept an essay about what I was doing - building a portfolio career - locked away for months while I waited for someone to confirm that what I was doing wasn’t weird. That it was acceptable. That I was ok.

That person never came.

There I was…endlessly waiting for permission. Hoping someone would shake me by the shoulders and say that it’s ok to quit the job, write the newsletter, post the TikTok, broadcast the idea, start the book proposal and do the work to become the real me.

All of a sudden the memories faded, and the streetscape came back into focus. I became hyper aware of the sounds around me. The group of guys behind me laughed as one of them cracked a dirty joke. A car horn honked in the distance. The pots and pans from the pita-joint around the corner of my building crashed and banged.

I felt lighter, somehow. Like the cascade of memories that had just tumbled into my consciousness had reminded me that one day, at some point, I had decided to stop waiting. I had decided that I would no longer ask for permission. That I would make my own way and move forward without regret.

And that’s really what life’s all about, isn’t it? Isn’t that why we’re here? To tremble on the edge of an idea. To explore and find out what we’re good at, what we enjoy, what we feel called to do. To turn each red light green.

Because when you stop asking for permission, you realise that there’s an entirely new reality waiting for you. One where you’re not surrounded by fog. One where you’re pursuing your life’s work. One where the pathway is open and the destination is clear.

There you are.

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If you’re waiting for someone else to give you permission, this is a message for you:

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🫶🏼 When you’re ready, here are two ways I can help:

• The Portfolio Career Operating System: the exact system I’ve used to grow my portfolio of work to multiple six figures across startup consulting and advisory, mentoring, writing, speaking gigs and digital products, all while being a solo operator (good systems = no need for assistants or contractors = high margins = good vibes). Learn more here.

• Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

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