Why Leaving a Dream Job is So Hard

No matter how hard I try to make this a soft landing, it's a hard one.

Today, I’m handing in my formal resignation letter.

There’s the sinking feeling that happens every time I leave a job. Part of me will deeply miss my coworkers, there’s some FOMO around what was to come and a craving to stay in my familiar routine.

Since I love my work, there’s a blurry line between professional connections and close friends.

To imagine my life without those people, habits or routines is a real struggle.

On my walk this morning, a part of me argued:

“You’ll never find work as great as this ever again. This is the best it gets. You found something here that’s even better than a business.”

Naturally, there’s a lot of internal resistance. But externally there’s change too. I struggle to navigate the flip from being deeply embedded in someone’s life to getting treated differently after people learn that you’re leaving. This is never personal. But you do get pushed to one side when you aren’t part of the plan anymore.

This is the part of the process I wish I could surgically remove. It pulls the heartstrings every time, and I think it’s what drives me to pursue soft landings.

My new life as an Entrepreneur

The chapter I’m leaving behind has been the highlight of my 20s.

Looking ahead, there are 3 reasons my new business could fail:

1. It gets lonely building a business in my room while the rest of the world is at work. I’m left to my own devices, uninspired because I’m not around likeminded people.

Through my job with Ali Abdaal, I found:

People who shared the same values, principles and ideas that I do.

People who inspired me, pushed me, reasoned with me, introduced me to new ways of thinking, politely interrogated old ones, confronted the bigger questions and, without fail, always blew me away by how impressive, intelligent and kind they are.

If I hadn’t met these people, it would be a lot easier to move on. The thought of starting a new chapter without of them is devastating.

It doesn’t have to be so binary though. It’s a limiting belief that I’m confronting. You can in fact stay in touch with the people who matter to you after you move on to do the next thing you really want to do. People come back. Or new people will come. Have faith in the process.

2. The offer for my business isn’t good enough.

If I had £1 for every time I thought of a business idea was going to be the one that is wildly successful in the least time possible, then I could probably afford to buy a London townhouse 😉

Jokes aside. Experience has taught me that what I think will work and what other people will actually pay for can be very far apart.

I don’t know what I don’t know. And there’s no guarantee that my business has enough legs to be profitable, let alone replace my salary.

3. I could procrastinate (a lot) without the guardrails of a manager or a 9-5.

Last year, I averaged more than 1 holiday per month.

Yep, let that sink in. How is that even possible, I don’t know. Suddenly I find myself in a position where I can’t blindly take annual leave since I’m my own boss.

For the first time in my life, I don’t get paid for logging in to Slack and being at my desk. I get paid based on my outputs. This is both comforting and disorientating.

Also, Parkinson’s Law says work fills to expand the time you allocate to it.

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The 12-Week Plan

This is one pot my favourite things to do. Write down the top 3 reasons why something won’t work (☝️), then list out the potential actions you can take today to mitigate against that.

I’ve combined this with building out some clear milestones for what I’d like to achieve in the next 12 weeks.

Here it is in all its glory:

The 12-week plan for how I was going to hit my goal of 2-3 clients by Christmas.

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Please tell me which topics you’d love for me to talk about.

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