Three Delusions I Learned from Quitting My Job That Could Stop You from Doing the Same

Right before I quit my job it felt like the start of a fairytale.

I imagined my ideal day. I pictured sitting in local cafes with my laptop and eating black forest cake with a chai latte. My work colleagues joined in on the fairytale. “You’re going to have the best life mate.”

A few weeks into this change in work, there a few delusions I’m starting to see about quitting a job and going solo that you can learn from.


Delusion 1: Without a job you will have extra time

Parkinson’s Law: Work expands to fill the time allotted.

I always thought this quote was stupid. Then I tried the no-job life. It can easily become true. Without a job you can waste the extra time.

Here’s a look at my Monday-Friday schedule so you can see how quickly time gets away from when there is more of it to spend. (It’s rough and obviously I don’t sit down with a stopwatch.)


Before I quit my job I’d wake up at 6 am and bounce out of bed. Why? Fear.

My worst nightmare was wasting the time before work. The time before work was when I worked on my side hustle. It was my ticket out of the rat race and catching trains to crowded offices.

Soon as I quit my job, I still woke up at 6 am. I’d walk to the other side of the bedroom and turn my alarm off. But then I went straight back to bed. I used the excuse “I need to get warm again — it’s winter.” Before I knew it thirty minutes of my day was gone. It’s not a lot of time. But losing time creeps up on you as the days move on and your new routine takes over.


Between this time I have a nice hot shower to shake off the Australian winter and relax. The showers get longer each day. Then I do a ridiculously silly beauty routine, even though I have no office to go to or people to see.

7:00–7:30 am

This is where I eat breakfast and procrastinate while watching Youtube videos. I call this Youtube watching “research.”

It isn’t really. Again, it’s fear.

7:30–8:30 am

This is the time slot where I read. I scour through the Pocket App or go down an endless Twitter rabbit hole. Like a programmed factory worker, as 9 am gets closer my fear level starts to increase.

“You’ve gotta do work, buddy.”

The work I often choose is maintaining social media accounts. Why? Marketing your work on social media is hardcoded into all writers. We think social media is a money-making tool that can further our careers. The truth is a little harsher. Building followers on social media doesn’t make you money directly, especially if you already have an audience.


Having meetings with people feels like work — given my entire 9–5 job was a series of back-to-back unnecessary meetings that sucked the life out of me and created zero progress. My salary worker programming kicks in once again and forces me into bad routines.

10:00–10:30 am

This is where I typically panic for thirty minutes. The fear kicks in again. My mind starts predicting all sorts of terrible endings to this phase of life.

“You’ll be back at work before you know it, you lazy ass.”

Or — “No company is going to hire you now you big douche bag. Social media will be the death of your career. You’ll be forced into hibernation.”


A series of unexplainable tasks occurs here.

11:00–12:00 pm

The first real work gets done for the day. I actually write something. I actually sit down and compile a business plan for a new idea. I actually send email pitches to people who can help me. I actually write a new article that becomes the outline for a new eBook. I actually write the title for the new eBook. I actually come up with the chapters for the eBook.

I feel slightly alive again.

12:00–1:00 pm

Time for lunch because my fiancé says so (I used outsourced accountability to pull me back into relaxation mode, and away from doing the work).

I eat slower than when I had a job because I can. I talk a lot to my partner. I drink extra cups of tea as though it’s normal.

1:00–2:00 pm

I do more high-value work. Momentum is building.

2:00–3:00 pm

“Let’s go walkie,” says my fiancé who talks to me like a dog, because I like dogs and mine died in 2005. I say yes because exercise is a cardinal rule all good little self-help believers follow. Walking is another excuse.

3:00–4:00 pm

I attempt to restart work. Fail. Fake Youtube research creeps in again.

4:00–5:00 pm

Productive work happens because the usual 5 pm salary worker psychology tells me it’s almost time to end the day and catch an imaginary train home to a pretty crappy apartment next to a fire station that has sirens going all through the night.

5:00–6:00 pm

End work. Read a book and call it research to pretend-work.

6:00–7:00 pm

Eat dinner with my partner (used to take 15 minutes).

7:00–9:00 pm

Watch tv with my partner and call it ‘couple time.’

9:00–10:00 pm

Race back to the computer and do my usual LinkedIn work.

10 pm

Sleepy time.

Time slips through your fingers when you have more of it

Look how much time I wasted. Before I quit my job I had a sense of urgency in everything I did throughout the day. Without the threat of an angry boss, I turned into a Youtube-watching hermit crab.

The lie is, having more time will help you work on your dreams. The truth is, having more time isn’t the answer to working on your big goals.

Delusion 2: You won’t get lonely working by yourself

I miss my work colleagues. As soon as you leave a job you think they’re going to be thinking about you every day like a lost lover.

The truth is most of them will forget about you within a few weeks. They want to stay in touch, but they simply don’t have time. They’re stuck working 12-hour days from home, trying to make up for the lost revenue your former employer is bleeding because of a global health crisis.

The good news is there’s always one. I have one work colleague who has become a close friend. I realized you don’t need lots of ex-colleagues to stay in touch with. One colleague who becomes a friend is worth all of the other relationships you shed when you quit your job and take an unconventional career path.

Delusion 3: You won’t regret your decision

On some days I do. I had it good. A 4-day workweek, a brand new Macbook, a fancy job title, cool customers, a job in tech — working with machine learning, AI, robotics, blockchain.

Regrets are normal after you quit your job. That’s fear, yet again, showing up at your mind’s door to focus your attention on the work that matters, that you quit your job to do.

Fear is normal.

Channel your fear into your new line of work.

How to Make Quitting Your Job an Actual Success

With these slight tweaks I got my workday back on track.

  • Accept fear.
  • Take a few weeks off after you quit your job to reset your mind (I should have done this).
  • Introduce accountability partners. Share your goals with them. Get them to ensure you stay on track with your new work goals.
  • Stick to a schedule. Book appointments with yourself in Gmail — this time slot is for writing, this time slot is for pitching, this time slot is for recording videos, this time slot is for working on the website, this time slot is for making sales calls, etc.
  • Set up constraints to enforce discipline.
  • Track where you spend time.
  • Remind yourself daily of why you quit your job. This is your motivation.

– Tim Denning

PS – If you’re interested in writing books, make sure to catch up on my Amazon Book Blueprint Mini Course. Check out Lesson 1 here and Lesson 2 here

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