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

LinkedIn

North America Sales Executive leading team of 25+ Sales Managers and single point of contact sellers who manage customers advertising on LinkedIn. Primary responsibility is to grow customer’s digital ad spend on LinkedIn.

Accomplishments include: 
• Built LinkedIn Marketing Solutions North America scaled sales organization, supporting 10k+ customers and $150M in annual revenue generation, averaging 112% quota attainment.
• Crafted team vision, global KPIs, and streamlined workflows, elevating employee satisfaction by 20pp to 90%+.
• Formulated revenue growth and churn prevention strategies by using customer insights, market analytics, and industry trends, achieving a 10pp boost in bottom-line performance, securing leading segment margins.
• Launched first US-based 3rd party outsourced sales vendor, covering $40M in annual revenue.

Awards:
GLOBAL SMB MVP Award Winner, July 2022
NAMER Club Sales Winner, July 2022
NAMER Leadership Sales Coaching Award, May 2022

Head of North America Scaled Sales | LinkedIn B2B & Online Advertising Sales

Second-line Manager overseeing a Client Solutions team of 30+ people and partnering with 10+ cross-functional roles across Australia, India & Southeast Asia, delivering $30M in annual revenue.

Accomplishments include: 
• Managed a diverse, multilingual region, tailoring sales strategies and employee development plans to accommodate cultural nuances and business norms in each country. Averaged 105%+ quota attainment.
• Facilitated growth of front-line managers through mentorship, enhancing sales coaching skills, and cultivating executive presence, leading to +15pp in employee satisfaction and +10% in revenue within six months.
• Deployed strategy to shift customers away from paper contracts into online buying, while maintaining high customer satisfaction. In under 9 months, online buying shifted from 15% of business to 90%+.

Head of APAC SMB Client Solutions  | LinkedIn B2B & Online Advertising Sales

Front-line Sales Manager managing Southeast Asia Account Management & Ad Operations Team (14 Account Managers and Campaign Managers in Singapore, Hong Kong & Japan). Team was developed sales planning, campaign set-up, campaign analysis, and renewal strategy. 

Accomplishments include: 
• Ensured seamless support for customers, maintaining 95% ad trafficking accuracy for Enterprise customers.
• Identified upsell and cross-sell opportunities to drive +22% incremental revenue to hit quarterly sales targets.
• Piloted innovative organizational restructure initiative merging account management and ad operations roles; led to global rollout of new org due to pilot results of +2M in-half revenue and +18% in customer satisfaction.

Awards:
APAC Marketing Solutions MVP Award Winner, January 2017
Singapore 'Act Like An Owner' Winner, December 2016

Manager, Enterprise Account Management & Operations | LinkedIn B2B & Online Advertising Sales

Lead Generation Specialist that partnered with Enterprise brands to identify digital marketing strategies to drive high volume of leads for the customer, while reducing Cost per Lead of advertising on LinkedIn by -61%.

Accomplishments include: 
     - Relocated from New York to Singapore to launch LinkedIn’s first marketing SaaS lead generation product across JAPAC, acquiring 100 new customers in the first six months.
     - Developed cohesive digital strategies that automate email, social media, and display marketing initiatives reducing time marketers spend on campaign creation by -72%, while improving lead volume by +62%.
     - Compiled comprehensive executive reports detailing MRR, CLV, CAC strategies across JAPAC region.

Senior Marketing Automation Consultant | CRM & Digital Integration Expertise

Bizo (Acquired by LinkedIn)

As a manager in our rapidly growing New York office, I played a key role in increasing office headcount by 30 people, improve client renewal rates by 17% and seamlessly manage the transition following Bizo’s acquisition by LinkedIn in August 2014. Responsibilities included renewal revenue forecasting, delivery rate analysis, training new hires, facilitating new product releases, and conducting performance reviews and employee development.

Accomplishments include:
• Supervised, led, and coached a team of 9 account managers, setting clear expectations and performance goals.
• Served as the main point of contact for escalated client issues, reducing customer churn rate by 31%.
• Partnered with marketers at F500 companies to generate leads and improve brand awareness.
• Focused on client retention by providing exceptional service, identifying upsell and cross-sell opportunities.

Manager of Client Solutions & Account Manager | Account Management, Customer Success

New York Red Bulls

Outbound Sales & Client Retention Executive for the New York Red Bulls, the Major League Soccer Team owned by Red Bull. Responsibilities included outbound prospecting, client retention of current season ticket holders, and running in-game event day experiences. 

Accomplishments include:
• Managed annual sales of 700 season tickets, group ticket packages, 10 premium suites, and 20 youth soccer programs. 
• Led game-day activities including on-field events, sales tables, customer service & troubleshooting fan issues. 
• 4 consecutive seasons of customer retention above 85%+, including year when prices increased +88%. 
• Named MLS Silver Award Winner for New Ticket Sales & Bronze Award Winner for Total Ticket Revenue.

Account Executive - Outbound Sales & Account Retention

Motivational and people-oriented Sales Executive, awarded MVP twice at LinkedIn. Experienced scaling enterprise and mid-market level sales teams into high-volume operations that drive exponential growth and expand market reach. Built and led LinkedIn B2B Ads North America scaled sales organization, which oversees 10k+ customers and $150M in annual revenue. Launched US-based 3rd party outsourced sales vendor, before transitioning ownership to full-time team to lead. 

Skilled leader in both North American and Asia-Pacific sales, averaging 110%+ in revenue attainment. Previously led both SMB Client Solutions and Enterprise Account Management divisions, gaining direct experience around how to drive customer success and growth across all customer types in both local and international markets. Prior to LinkedIn, worked at an acquired tech start-up so understand hyper-growth phases and the need to ensure sustainable, healthy business growth, and strong management to remain attractive to investors. 

Most passionate about my team and the people I am around. I love coaching, mentoring, and helping individuals become their best professional selves. I'm authentic and vulnerable with a sense of humor that drives connectivity between groups. My Manager Support scores consistently have been in the top 10% of LinkedIn. Cross-functional partners love working with me because I'm kind, yet direct. Always clear on what's good and what's not, while identifying clear, actionable steps forward toward joint success. 

Currently on a 6mo career break recovering from an achilles surgery and completing a Berkeley Haas Product Management Certificate to compliment my sales leadership and digital marketing skillset. Plan to re-enter the workforce in 2024. Email me at mallory.s.fahy@gmail.com to connect personally or about any role that I'd be a stellar fit for!

Skills: Managing Managers, Strategic Planning, Communication, Sales Coaching, Scaled Sales, SMB Sales, Revenue Forecasting, Business-to-Business (B2B), Performance Management

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Tim Denning

Mallory (Sullivan) Fahy

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