Aussie writer with 1B+ content views in 10 years | I teach people to use writing online to create career opportunities | Let's connect: tim@timdenning.com

I quit my eCommerce startup with 100+ employees. Then got depressed, developed an eating disorder, and got a minimum-wage job in a bank. I now work for myself and make 7-figures writing.

I'm not that smart and have no college education. The way I used the internet made the difference.

And going to a Tony Robbins event changed my mindset. He taught me to go from being a victim to be in control.

This led to:

• 1B+ content views
• Financial freedom
• Book deal with a major publisher
• Meeting my heroes (like Tony Robbins)
• Quitting my banking career forever in 2021
• Multiple successful businesses fuelled by obsession

My mission: Help 100,000 people start online businesses. 

My beliefs that drive everything I do:

- Anything is possible
- Positivity above all
- Ego is the enemy
- Challenge the status quo
- Chase obsession, not passion
- Always be kind, grateful, and a good person

How can I help you?

• Social media audience building
• Starting or growing an online business

Join my email list with 200,000+ other high performers for more helpful insights:
https://timdenning.com/start-social-hustle-linkedin-bio/

Tim Denning

I interviewed 50 people who quit their jobs in 2024.

Here's what nobody tells you.

━━━━━

They didn't quit for more money

38 of them took pay cuts. Some massive ones

The software engineer who went from $180K to doing one-off writing gigs. The CMO who became a pottery teacher. The investment banker selling surfboards

Everyone said the same thing: "I'd do it again tomorrow"

━━━━━

The pattern that shocked me:

**The 3-month mark**
Everyone hits it. Pure terror. Bank account screaming. Partner questioning. Parents "concerned."

There's a twist: The ones who made it past month 3? They never looked back.

The ones who returned to corporate? All quit before day 90.

━━━━━

What they actually quit:

• Sunday night anxiety (47/50 mentioned this)
• Asking permission to live their lives
• Meetings about meetings about nothing
• Pretending to care about Q3 targets
• The soul-crushing commute
• Being "on" from 9-5 regardless of actual work

Not jobs. They quit the entire system.

━━━━━

The money truth nobody admits:

Month 1-3: Hemorrhaging cash
Month 4-6: Ramen profitable
Month 7-9: Matching old salary
Month 10-12: "Why didn't I do this sooner?"

But 23 of them said something that stopped me cold:

"Even if I never matched my salary, the freedom is worth more."

━━━━━

The unexpected side effects they reported:

• Marriage improved (32/50)
• Lost weight without trying (28/50)
• Stopped needing anxiety meds (19/50)
• Kids said they're "different" (better) (41/50)
• Sunday became just another day (50/50)

One guy: "I didn't quit my job. I quit dying slowly."

━━━━━

Their biggest regret?

Not the money lost
Not the security abandoned
Not the benefits forfeited

49 out of 50 said the same thing:

"I wish I'd done it sooner."

The 50th? She wished she'd been bolder

━━━━━

What made them pull the trigger:

• Health scare (12)
• Kid asking "why are you always tired?" (8)
• Passed over for promotion (7)
• Random Tuesday breakdown (11)
• Watching someone die with regrets (6)
• Just... done (6)

Not grand epiphanies. Just moments of clarity.

━━━━━

The skill they all developed:

Comfort with uncertainty.

Corporate trains you to fear the unknown. Quarterly forecasts. 5-year plans. Predictable misery.

These 50 learned something better: How to surf chaos.

━━━━━

The advice they'd give their past selves:

"Your backup plan is a prison"
"Start the side thing NOW"
"The fear never goes away, jump anyway"
"Corporate security is an illusion"
"Your kids need you present, not rich"

My favorite: "Stop asking for permission to live your own life"

━━━━━

None of them had it figured out
None of them were "ready."

All of them are more alive than when they had "secure" jobs.

━━━━━

To anyone reading this from a cubicle:

That feeling in your chest? It's not anxiety.

It's your life asking for permission to begin.

What's stopping you from escaping the rat race? 👇
♻️ Repost if you know someone who needs to read this

Join my Substack: https://lnkd.in/gMkRFmj9

Most people grind 40 years at a job they hate.

So they can retire at 67 and finally "start living."

If they make it that long.

━━━━━

Met a guy last week. 66 years old. One year from retirement.

Stage 3 cancer diagnosis.

"I was so close," he said. "One more year and I could've traveled."

40 years of waiting. For nothing.

━━━━━

The retirement lie we all bought:

• Suffer now, enjoy later
• Trade your best years for a pension
• Postpone happiness until 67
• Work yourself sick for "security"

Meanwhile, your knees give out. Your energy tanks. Your spouse becomes a stranger.

You saved all that money to enjoy a life your body can't live anymore.

━━━━━

I watch 30-year-olds planning for retirement like it's the f*cking promised land.

Contributing to 401ks while skipping their kid's soccer game.
Working weekends to boost that pension.
"Just 35 more years," they say.

35 years of Sunday night dread. 35 years of "not now, I'm working." 35 years of waiting to live.

For what? To be the richest person in the nursing home?

━━━━━

The people who get it do this instead:

Mini-retirements throughout life. Not one big one at the end.

Take 3 months off at 30. Travel for 6 months at 40. Start that business at 50.

Use your energy while you have it. See the world while you can walk it. Play with your kids while they still want you around.

━━━━━

"But I need job security!"

Your job isn't secure. Ask anyone laid off after 20 years.

Your health isn't guaranteed. Ask anyone with an unexpected diagnosis.

Your retirement isn't promised. Ask the 66-year-old with cancer.

The only thing guaranteed? Right now. Today.

━━━━━

Stop banking on someday.

Someday you'll travel. Someday you'll write that book. Someday you'll learn guitar. Someday you'll actually live.

Someday is a scam sold by companies that need you to believe happiness can wait.

It can't.

━━━━━

To everyone killing themselves for a retirement they might never see:

Take the trip now. Start the side project now. Have the experience now.

Your 67-year-old self doesn't want your money.

They want your memories.

What are you postponing until retirement that you could start today? 👇
♻️ Repost to share this idea with your network.

If you want to level up your career faster, then join my unconventional Substack newsletter with 162K others: https://lnkd.in/gMkRFmj9

My 4-Year-Old's Business Card Says 'CEO'

But she's only 2. And that's the whole f*cking point.

━━━━━

I'm already teaching her what corporate won't.

Not ABC's and 123's. The real curriculum:

How to fail without feeling like a failure.
How to ask for what you want without apologizing.
How to see problems as puzzles, not roadblocks.

While other parents prep their kids for employee life, I'm raising an owner.

━━━━━

Here's what I'm NOT teaching her:

• "Wait your turn" (opportunities don't queue)
• "Color inside the lines" (innovation lives in the margins)
• "Don't talk to strangers" (your network is your net worth)
• "Share everything" (know your value, price accordingly)
• "Be careful" (calculated risks beat careful stagnation)

Controversial? Maybe. But I've seen where conventional wisdom leads.

━━━━━

The corporate skills they'll teach her in school:

Sit still. Follow instructions. Ask permission. Wait for approval. Don't question authority. Memorize the right answers.

Perfect recipe for a middle manager in 2045.

━━━━━

The real skills I'm teaching her now:

**"No" is data, not rejection**
When she wants a cookie and I say no, we talk about negotiation. What else could she offer? Different timing? A trade?

**Money is a tool, not a goal**
Her piggy bank has three slots: Spend, Save, Give. She decides the ratios. Already learning money flows, not just accumulates.

**Problems are opportunities in disguise**
Toy broken? Let's fix it. Or invent something better. Can't reach something? Find a solution. Every obstacle is a chance to think.

━━━━━

My corporate friends think I'm nuts:

"Let her be a kid!"
"She needs structure!"
"What about college prep?"

Meanwhile, their kids are being groomed for jobs that won't exist.

━━━━━

By the time she's actually 4, she'll understand:

• Value creation vs time trading
• Asset building vs paycheck chasing
• Problem-solving vs permission-seeking
• Leadership vs management
• Ownership vs employment

Not because I'll lecture her. Because she'll live it.

━━━━━

The business card thing? It's not cute. It's preparation.

While other kids play "house," she'll play "startup."
While they practice being employees, she'll practice being the employer.
While they learn to fit in, she'll learn to stand out.

━━━━━

I'm not raising her to have a job.
I'm raising her to create jobs.

Not to work for the system.
But to build better systems.

━━━━━

Will she actually become a CEO? Who knows.

Maybe she'll be an artist. A teacher. A stay-at-home parent.

But she'll approach it like an owner, not an employee.

And that makes all the difference.

━━━━━

To every parent reading this:

The world needs more humans who think like owners.

Start young. Start now.

The employee mindset is learned. So is the entrepreneur mindset.

Choose wisely.

What "unconventional" skill are you teaching your kids? 👇
♻️ Repost if you're raising owners, not employees

ATS Critical Facilities

CF Engineer 1

Ainsworth Inc

• Assists Delta Connects in designing and selling control systems for commercial buildings.
• The idea is to move into a sales role after mastering the basics of construction project management, to include working with contractors and designing building plans.

Estimator

Urenco USA

Building Operator III

Entest of Testforce Systems

• Commit to growth and development by participating in supplier and training workshops (technical andsales).
• Travel (as required) throughout the United States of America and Canada.
• Demonstrate strong technical competence in our suppliers’ products and how they can benefit the
customer.
• Build strong working relationships with customers and suppliers.
• Identify and prioritize accounts by developing a deep understanding of customer profiles including details on the customer’s businesses, strategies, operating methods and needs.
• Identify new sales opportunities with existing or prospective customers.

Technical Account Manager

Testforce Systems

SolarWinds

As a Sales Development Represenative, I make 60-100 cold calls + e-mails a day to schedule discovery calls and demos of Solarwinds products. I use a variety of tools in order to prospect, such as Sales Navigator, Salesforce, Outreach, Netsuite, and Zoominfo.

While my job primarily involves cold calling for meetings, with almost no inbound, management trusts me enough to do Solarwinds product demos as part of discovery calls before I qualify a meeting. My programming experience helps a lot with demoing some of the more involved software such as security and database analysis.

I bring a level of technical expertise and engineering knowledge to. My goal for the next 3-6 months is to build my business acumen with sites like CIO and Harvard Business Review to give even more value to clients.

Sales Development Representative

OEM Group, LLC

Managed relationships with emerging and established customers of OEM Group, a semiconductor capital equipment manufacturer. Provided integrated product solutions from tools to customer support contracts for semiconductor customers from universities to microelectronic manufacturers.
* Used a combination of inside and outside sales techniques to assist senior engineers, C-level executives, and VPs with purchasing multimillion dollar tools, upgrades, and services from the Lead to the Close stage.
* Maintained pipeline predictability and forecast accuracy via face-to-face meetings, teleconferences, and phonecalls for 80+ FABs and foundries.
* Covered a sales region to include TX, CO, NM, AZ, and MN.

Account Executive

DRS Technologies, Inc.

Designed procedures and test fixtures and used these to executed tests on Naval power electronics such as overload relays,controllers, contactors, meters, circuit breakers, and switchgear. Tests include thermal, humidity, computer operational tests,hi-impact shock, and withstand and interruption testing. Able to repair and troubleshoot the hardware and software of units under tests to MIL-SPEC and customer requirements.
* Developed, reviewed, and tested over 2000 hours worth of procedures to test military hardware according to Navaland customer specifications.
* As needed, worked closely with a rotating team of technicians and other to support continuous testing, procedurerevision, and test fixture construction.
* Instrumental in re-qualifying the N2000 DRS Overload Relay under budget and on time through the use ofprogrammable power supplies and customized AC Controllers.

Electrical Test Engineer

CSID

Led and developed an electrical engineering graduation project, under the supervision of CSID, a peer-to-peer botnetinfiltrator called CAP2P. Project required several months worth of server sandbox assembly, malware decrypting, and programming.

Software Engineering Intern

US Navy

After 18 months of schooling at Nuclear Power School/Prototype, served the rest of my career at the USS John C. Stennis stationed in San Diego, CA and then Bremerton, Washington.

Senior reactor operator during deployment, along with being chosen as the reactor operator for the ORSE workups. Position required months of downtime training to culminate in a multi-week performance where difficult and esoteric plant conditions are simulated to test divisional readiness and level of knowledge.

Nuclear Reactor Operator

I wish to share others' thoughts and raise questions on the aspects of sales and business culture that I feel get overlooked for being too counterintuitive or obscure. Which is why I also have a fondness for sales and marketing leaders who think at a more systemic level like Dave Brock and Keenan and Hank Barnes. These leaders specifically see the value in focusing on details and trends we overlook and try to bring our attention to them, and I want to one day be one of their peers.

As for my personal history, I enlisted in the Navy as a Nuclear Electronics Technician/Reactor Operator for six years, then received my electrical engineering degree in a Top Ten university. I spent two years with DRS Naval Power as an Electrical Test Engineer and afterwards transitioned from Engineering to Sales with Solarwinds as a Sales Development Representative (SDR). After working at TestForce as a Technical Account Manager, I spent some time in Operations as a Building Operator over at Urenco, which provides enriched Uranium. Worked as an Estimator at Delta Connects, but left shortly after ChatGPT came out in March 2023 after seeing the potential of Large Language Models (LLMs) and Prompt Engineering. I am currently looking for a role that will allow me to leverage my past experience in sales, engineering, and the military in a way that develops AI through the magic of LLMs.

I know it seems strange to say that becoming a prompt engineer is a lifelong dream, but it is. The technology just wasn't there to give me clarity of vision until ChatGPT got released, but now that it's here, I know exactly what I want. I want a job that engineers and creates, but not just a surface-level on requirements. Having been on both sides of the vendor and customer table, I know how frustrating it is not to be able to precisely execute a project the way you want due to real-world friction. And LLMs promise to change that.

As far as teaching goes, I've had quite a bit of experience. As a B2B sales rep who gave customized solutions to customers, such as semiconductor capital equipment or commercial HVAC plans, I know how to explain my proposals and give post-sale support to customers. I also had to train other people while I was in the Navy. And I don't just teach as part of my career, one of my favorite things to do is to write guides. I have a couple of guides I am particularly proud of in this link: https://docs.google.com/document/d/1zgCcjuHcuq1aoZl0Z0ljVxchV6WPOZ8F5DYBqn3vTRk/edit

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