Category : Entrepreneurs


We’ve Been Trying to Quit Our Jobs Since Forever. The Great Resignation Is Stupid.

The Great Resignation Is Stupid.

Photo by Hanna Morris on Unsplash

The phrase “The Great Resignation” is a plague.

It’s infected all media platforms. Everyone’s dropping the new buzz phrase like we did back in 2019 with the word #Innovation. Good god. Make it stop.

Since when is wanting to quit our jobs new? It’s not. Still, I quit my job.

The 1990s version

In the 1990s I remember infomercials that would advertise the franchise life.

“Buy this great Jim’s Mowing franchise and you’ll be free from your boss.”

They’d then whip up a stock photo of an angry boss pointing their finger. They’d even use Las Vegas magic show techniques. They’d flash the tv screen black and white. Then the words “Now! Now! Now!” would appear. Then smoke. Then a strange, deep voice would speak.

“Is this the life you are destined to live, or is there something more! more! more! you could be doing?”

The scene would quickly change to the beach. Palm trees in the background. A hammock conveniently placed between two trees. Cocktails served by a waiter … and no laptop. Laptop life didn’t exist back then.

As a 90s punk kid I didn’t get it. What’s work? School is the real downer. Help!

The Great Resignation misses the point

It’s not about the coroni-macaroni. It’s not a timing thing. It’s not because of LinkedIn content that we’re finally reevaluating our careers.

We didn’t suddenly wake up and go, “I’ve had enough of this sh*t.”

It was always going to happen.

We’re tired. The factory worker model of employment hasn’t worked for a long time. Our motivation levels are zero. KPIs don’t get anybody excited. HR puppets selling company life dreams are ignored by anybody with a brain.

‘Heads of Nothing’ that don’t do any real-world work — unless you count meetings — are slowly dying. Chief Executive actors are another category of huge egos that everyday workers are sick of — and their 300x higher salary for giving a few speeches at town halls each year.

The point is, now we’ve been home alone for so long we’ve finally accepted the career lie we’ve been living.

But the lie isn’t new.

The internet guaranteed that the number of workers that wanted to kiss a boss’s butt each day was going to rapidly decrease, eventually.

We want autonomy

Some people are trying to manage multiple side hustles to figure out what work they want to get paid to do. Some people are trying to manage a family with kids that love to interrupt Zoom calls and need to be picked up from school. Others like flexibility to work during their best hours.

The idea we all start and finish work at the same time and work for five days and rest for two days is old fashion. Technology means we’re always working, even when we try not to. The segregation between the two, therefore, means the factory worker 9-5 dream is dead. It was always going to die.

Most of us don’t work in factories anymore and click a button to punch in and punch out.

Most work can happen from any location and it should. Our work location determines our cost of living — and the cost is too damn high in big cities. That’s why we want to quit our jobs so we can be location-free.

We wouldn’t need to quit if you let us do Zoom forever. Too late.

Gif Credit: Gifer/Pegg Olson

We want control

Traditional leadership is even more broken. Our bosses are so busy stuck in back-to-back meetings that they barely know us.

What we want is control. We want to be trusted to make small decisions and own our tiny part of the business pie. We don’t need bosses anymore to tell us what to do. Sing it with me now! Come on…

~ Well we don’t need no one to tell us what to do
Oh yes we’re on our own and there’s nothing you can do
So we don’t need no one like you
To tell us what to do

~ We don’t refer to the past when we’re showing what we’ve done
Our generation gap means the war is never won
The past is in your head
The future’s in our hands

Aussie Band: Living End

Software can tell us what needs to be done. Code can verify what we do.

Our career path has little control, too. There’s no guarantee that if we deliver the outcomes we’ll get our end of the bargain.

You sell us dreams but we just don’t believe them anymore.

The brainwashing phase is over. The prove it with code period is here. Put it in a smart contract if you mean it, otherwise please shut up.

We want to use our creativity

As robots and code continue to take over more traditional jobs, all that will be left is creativity. We may as well start now then. Let us use our creativity. Make creativity levels a KPI if you must.

Hardcode creativity into every job. Force us to be creative if we’ve forgotten how to be. Measure and pay us based on creativity rather than hours worked.

Hours worked doesn’t measure value. Creativity deployed measures valued.

“Hit revenue number” is no longer a reason to go to work.

We need meaning in our work. That’s why we quit our jobs, because we get more meaning when we create our own work through freelancing, contracting, and making WIFI money.

The truth is we figured out a long time ago that we can make money online. We can leverage or borrow other people’s assets and then add our creativity over the top and make a living. So we are. It was always going to happen.

Traditional company infrastructure — like offices, furniture, departments on top of departments that force prices up — are dead weight. Your operation model is bloated. Optimization now happens at an exponential rate, so inefficiency must decrease at an even higher rate.

You either optimize or die. So instead of staying on the Titanic, we’re continuing to jump off the ship to enter the digital world without you.

Let’s kill the buzzword and call it what it is

No more “Great Resignation” headlines, please. We’ve always been trying to quit our jobs so we can own our time and make our own choices. It’s nothing new. Work will change whether bosses and businesses like it or not.

We’re just going to keep doing what we were always going to do: quit.

As Web 3.0 takes over, the word “digital” is going to look like a drop in the ocean in comparison. Your buzzword innovation departments will be steamrolled.

Business-decisions-as-code already exists. Meetings will continue to be deleted and replaced with consensus algorithms. Customers will make more of the decisions with voting rights of the products and services they use.

Leadership-as-code is coming. Bosses, you’ve been put on notice. “The Great Boss Annihilation” is next.

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It’s Time to Build Something That Will Change Your Life. Stop Wasting Time.

Stop Wasting Time

Photo by Fábio Lucas on Unsplash

A lot of you have a guilty secret.

You’re literally dying to build something.

You’ve had an idea for years. You’ve done a few experiments. But to date you still haven’t started building. Creators get all the rewards. A creator is simply a person who builds something online. All of us have it inside of us to do it.

Don’t let ideas die inside of you

My business partner Todd Brison has an interesting way to explain it.

He says every creator leaves behind two graves when they die.

One grave contains the skin, bone, organs, and hair leftover from your body that will slowly decompose in the ground to eventually become at one with the soil. The second grave holds all of the ideas you never got to release.

Some of the smartest people are in the cemetery. They were geniuses but we never got to know because their ideas were buried in their second grave. It’s why I’m so crazy about writing online.

I want my second grave to be empty when I leave this earth.

Many people will go to their graves early without your ideas. Your ideas have enormous power. They contain life lessons, moments of enormous creativity, strategies, and helpful inspiration that can get someone out of a dark place.

When your ideas die so do the people who they could have helped. That scares the crap out of me. It should scare you too.

When you build something it changes your life

The trouble is I can’t tell you how.

Creative endeavors don’t reveal their awesomeness until long after they’re released into the world.

I spent years building a portfolio of writing. I didn’t really know where it would lead or what it had the power to do.

Even after 7 years, I still find out that some of my writing helped people start a business. For others it helped them rethink their life or get out of a bad relationship. And for at least one person, that I’m aware of, a single article stopped them from taking their own life.

I didn’t know this at the start. Helping other people with their problems changed my life, although it wasn’t obvious.

The act of creation rewires your thinking. It shifts your mind into creation rather than the default mode of consumption.

A good life needs meaning.

Creation gives meaning to your life. It takes everything you consume and all the ideas bubbling around in your head, and makes them all worthwhile.

I started my YouTube channel 1.5 yrs ago.

Changed my life.

I started my Twitter account 9 months ago.

Changed my life.

I started my crypto journey 4 yrs ago.

Completely changed my life.

It’s time to build something that will change your life.

— OhHaiAndy

Why we don’t build our dreams right now

You’re not stupid. Some of this is obvious. Let’s explore the hidden problems.

1. You think you need more information

The desire to collect information in your favorite note-taking app until the end of time is huge. You’re never ready. It feels like there is always more to know.

“No point building now. The quality of my work will be too low,” you say to yourself each time you sit down to start.

You learn by doing.

The best learning is when you do trial and error. When it’s your mistakes and lessons you learn, the education sticks around — it has context. There’s only so long you can consume everybody else’s learning. Eventually it will feel empty.

You can live through someone else’s eyes, or let your eyes witness the gorgeous miracle of having deeply personal experiences.

2. The secret feeling none of us wants to admit

I shouldn’t admit this.

Here goes: I wanted to quit my job for years and build things. Fear held me back. I’d have nightmares of everything *not* working out. I’d do role plays in my head of having to beg my boss to take me back, and them saying, “yes, but we can’t pay you the same anymore.”

We all experience fear, even though we pretend to the outside world that we’re flawless and nothing scares us.

The trick is to, first, admit your fear to yourself. Then admit your fear to another person. It helps put a voice to those destructive thoughts. Then all you do is act in spite of your fear. Feel the fear and do it anyway, as the cliche goes.

Once you know you’re not alone with the feeling of fear it normalizes it.

What’s obscure feels like an erotic fantasy you should never share. What’s normal is easy to talk about. That’s how it can be overcome.

3. The past does not equal the future

You may have been a creator before. Things may have gone bad.

I feel for you. Ask anyone who knew me during my startup days. The mistakes I made were beyond idiotic.

For example, witnessing employees commit sexual harassment and saying nothing is something I’m not proud of. Even worse, when I found out the extent of the problem and our company organized training to make it stop, I was the only person not to attend. I thought I was too good to be there. That sent the message to staff that the problem wasn’t real. So it continued until we took it seriously.

Those mistakes haunt me.

But the past can be corrected in the future. You can learn from your mistakes. If all you do is reflect on what you screwed up, you can never move forward. Acknowledge your errors and then omit them in the future.

Take mistakes and use them as opportunities to build better next time.

The time is right now. Today.

The internet contains infinite leverage. You can literally build anything you can imagine without too many constraints. The only limit to what you can build is your mind.

The sooner you start to build, the sooner you can start to get results. We’re on the cusp of Web 3.0. This will give creators even more tools and lower the costs and barriers to entry.

If you’re not excited, then get excited. This is the best time in history to be a creator. Stop wasting your time on Netflix. Stop engaging in toxic conversations and being a serial social media commenter. Stop speculating. Stop with the excuses. Stop with waiting for the perfect time.

The trouble is, you think you have time.

— Jack Kornfield

You don’t have time. This is your wake-up call.

Life is short. Start to build something today that will soon change your life in bizarre ways you could never predict.

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Hustling Is Stupid. You Inevitably Burnout.

Hustle Culture

Photo by Tong Nguyen van on Unsplash

Side hustles can change your life.

*Inserts huge caveat*

But don’t let the second word “hustle” fool you. Too much hustle leads to burnout, and burnout is stupid. Why? You’re a useless human when you’re burned out. How do I know? You’re speaking to the burnout king.

I once held the record in my 20s for 7 years without a single annual leave day.

“You’re lazy. Who takes holidays? LOL.” That person is dead. I don’t think like that anymore because it’s just not worth it.

Let’s not worship people who work 18 hours a day, 7 days a week and think it’s cool. Instead, let’s make these activities below go viral.

A hard stop to the end of the workday

For many of us the workday is 24/7. Before I quit my job earlier in the year, I was getting invites to meetings at 11 pm on Saturdays. One of my bosses got angry at me.

“You missed an important meeting. You need to check your phone more often.”

The meeting I missed was due to our company getting hacked (publicly). There was no outcome to the meeting other than to restate the fact we got hacked. There was nothing I could do about it, as I can barely find the power button on my desktop computer.

On Monday I got the official correspondence and sent it to clients. Not one of them replied or cared, as expected. A company being hacked is like a natural disaster. Bad stuff happens.

From that moment on I set a further hard stop. No calls or emails after 6pm, and definitely no weekend meetings. People got the message.

When you switch off for the day turn off your devices. Being on call 24/7 stops your brain from relaxing and decompressing from the day’s events.

Mental health days

It’s no secret I endured severe mental illness. Later in my life mental health days became a thing. I embraced them. Co-workers called me a snowflake.

We’re not snowflakes for needing mental health days. A tired, frustrated brain is highly unproductive. It’s better to reset yourself and come back to your work fully recovered and a lot more productive. What looks like lost business profits because of free days off is actually higher company output in the long term.

Mental health days aren’t for snowflakes. They’re for smart, highly-effective, driven, action-orientated weapons of mass destruction.

Work that has meaning over work that pays a lot

Hustle culture encourages us to work hard for money. Screw that.

Work that has no meaning — other than to make a boatload of money — will burn you out faster. Humans are driven in the long term by why we do what we do, according to Simon Sinek.

The downside of meaningful work is it requires you to think more. You can’t think deeply when you’re brain is exploding from back-to-back meetings all day. So high-quality work needs rest, and mediocre work needs enormous amounts of time.

How you spend your time decides which category you fall in.

A busy calendar and a busy mind will destroy your ability to do great things in this world — Naval Ravikant

A minimum of 4 weeks holiday per year (8 weeks if you’re a badass)

Holidays are where you zone out. For many of us, holidays are where we jump on planes and travel the world. This might seem silly. It’s not.

When you travel to new countries you experience new cultures. That changes how you work and interact with others. If you want to be more relatable, and less like a hustling zombie, you need to get out there and meet people who are nothing like you.

A friend of mine took it a step further. When he got a promotion at a new company he sacrificed more money for 8 weeks of holidays a year instead of 4. Now that’s badass.

Time away from work enhances your work. Read that again.

8-hours sleep per night. Sleep-ins on Sundays.

The productivity snobs stay up until all hours of the night. They think it’s cool. Not really. Humans that don’t get enough sleep do damage to their bodies according to science.

Sleep is a productivity enhancer. When you wake up after a good night’s sleep, you’re on fire once you get going. When you wake up tired from not enough sleep, all you can think about is going back to bed.

Thoughts about going back to bed are a distraction worse than phone notifications that interrupt your workflow.

If you want to go to the next level then sleep in on Sundays. Give yourself a reward for a week full of hard work. Rewards like this are a form of motivation no amount of money can buy.

Have rewards to look forward to.

Work that generates outcomes over time worked

The amount of time you work doesn’t matter. That’s a factory worker concept that should have died with the industrial age.

We’re now in the internet age that has infinite leverage. Leverage means the number of hours you work doesn’t matter.

It’s the outcomes you achieve while you work that count. It’s the reason good copywriters can demand over $100,000 for a short email. The time it takes doesn’t matter. It’s the skill they’ve developed and their proof of work that attracts the fee.

Cliche (but true): work smarter not harder.

Friends over dead bodies

Hustle culture makes us see those around us as competition, like we’re all in some make-believe war and leaders are Generals. LOL. I once worked with a bad boss who believed this fantasy.

Those around you aren’t dead bodies you have to walk over to achieve results. Nope. They’re your friends.

Ask some of the top writers on this platform. They’ll tell you my motto: we rise by lifting each other up. That’s why I give away my best stuff for free and support those who have similar goals. I’m not interested in hoarding all the good stuff for myself. Maybe I’m stupid.

The best part about an online business is the friends you make in the process, not the money. Few people understand this and it leads them to focus on the wrong goals.

Make friends. Friends become collaborations. Friends help each other. Friends grow their results together. Friends don’t see jealously, only opportunities.

It all boils down to this

Hustling too hard leads to burnout. When you’re burned out you’re in a sh*tty mood. Sh*tty moods are highly unproductive.

I’ll leave you with this killer strategy from Eric Barker: “Think a little less about managing the work and a little more about managing your moods.”

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Seven Things I Had to Give up to Quit My Job and Never Go Back

Quit My Job – Tim Denning

Photo by Charles Collingwood on Unsplash

A dream job sounded like the answer.

Becoming a young Gordon Gecko on Australia’s Wall Street seemed like a smart plan. I tried to pivot my career into stocks. I got close to my goal. But I discovered the world of tech and banking and did that instead.

Later, I realized I didn’t want a job after all of the effort. Here are the things I had to give up to quit my job and decide never to go back that can help you think through your own career.

Give up the pain of past failure

I only realized this recently: I took a job because of a bad entrepreneurial experience in the startup world that caused me to walk away from everything.

What I’ve never said before is I made a big mistake. Instead of getting a job, I should have started all over again as an entrepreneur. The reason I couldn’t is because I was afraid.

See, when we have one bad experience that blows up in our face it scars us. So we do anything we can to get away from it. That’s what I did by doing a complete 360 and going from a startup to a minimum wage employee.

I had to give up the idea that one bad failure should cause me to seek an escape and do the opposite of what I love. Failure means same direction, different route. Not wrong direction, do a u-turn.

Give up bad money habits

In my 20s I worshipped the gods of luxury. Stupid BMWs. Fine dining restaurants to look cool. New clothes every few weeks to show wealth.

My worst money habit was I had no safety blanket. I spent every dollar I earned. I liked buying audio software and giant keyboards with synthesizers attached to them. One could easily cost $5000.

Then I’d buy expensive microphones that would get used a few times a year so vocalists could sing on my music. My side hustle of music never made me any real money. Yet, I kept throwing bad money at it with zero return. I had to give up these terrible spending habits.

My mantra became: spend less than you invest.

Give up the fear

Most people will choose unhappiness over uncertainty — Tim Ferriss

Not having a job can be scary. There’s no way round it other than to accept the feeling. Otherwise you can end up in a job where you’re unhappy because you’re afraid of uncertainty.

Uncertainty goes down when you build yourself a safety net. That’s what your investing habit is for.

When you have a few financial assets to your name, it’s easier to stomach back-to-back months of no income while you figure out life without a job. Or if you discover your side hustle dream isn’t finished and needs a rework.

Feel the fear and do it anyway, says Tony Robbins. I’m glad I did. Give up the fear, or at least accept the fear and use it as motivation.

Give up the toothless excuses

Obviously not everyone will be better off without a job. But some of you will. What held me back were the excuses.

  • “I’m not ready.”
  • “I need to learn more before I quit.”
  • “I need a team.”
  • “I need more money.”

There are millions of excuses your clever brain can come up with. But excuses don’t create progress. They keep you in comfort which leads to regrets if this whole quit-your-job thing is something you really want to do.

Squash the excuses. Here’s how: you can always get another job again. Now you have a Plan B. No need for excuses.

Give up LinkedIn shame

Some of your colleagues will hate you. They’ll tell you they’ll keep in touch and then never speak to you again. If you’re on LinkedIn some of your connections will think you’ve lost the plot.

You’ll attend functions with old work colleagues and feel like an alien. You won’t be able to speak their language anymore. They’ll secretly laugh at you when you go to the bathroom to urinate. That’s okay.

Shame is only placed on you because of a lack of understanding. There are two possible reasons:

  1. The people who shame you wished they could quit their job.
  2. Or they can’t imagine a world without their job.

Both reasons are fine. You do you. Feeling shame for going after what you want just isn’t worth it. Your true friends will be revealed when you quit. The people who used you for your career status will be revealed, too. Move on.

Give up salary crack

The three most harmful addictions are heroin, carbohydrates, and a monthly salary — Nassim Taleb

A predictable salary is a drug I love more than candy. The consistency of it is nice, but I figured out it leads me to be paid a lot less as a consequence.

A salary is where you give up your leverage to a middle man who gets the upside in return for the comfort of the same amount of money each month. For plenty of people that works fine.

No problemo.

For me it’s a nightmare. I knew I was leaving a lot on the table. I didn’t want the extra money to buy a Lambo. No. I wanted the money to buy back time.

A near-miss with cancer in 2015 taught me to be fiercely loyal to time, because every day we’re slowly dying. So I gave up the gorgeous salary in return for lumpy paydays. Some months I earn money. Some months there are tumbleweeds rolling through my apartment because I didn’t work hard enough.

The solution is to keep money from the larger paydays to cover the times when there are no paydays and you’re figuring sh*t out. Proper money management sets you free from a job, if that’s your goal.

Give up being poked with a stick

A boss has one job: to poke you with a stick to get the most out of you. Motivation can be hard to cultivate. I had to learn to give up the brute force variety of motivation my boss gave me and to “self-motivate.”

Sounds easy. It’s not. The temptation to binge on YouTube and eat mango gelato twice a day is enormous. That’s why you need clear goals. Not cheesy self-help goals written on the wall that you place gold stars on like a 5th grader. I mean real goals.

Goals that move your work forward. I mean ranking what you do each day based on fake work versus work that leads you to pay utility bills, cover the cost of the roof over your head, and put tacos in the refrigerator.

And the biggest liar is yourself. The temptation to label something work that’s actually bullsh*t in disguise is high. So learn to be honest with yourself, otherwise you’ll end up right back at the cubicle with your boss’s stick lodged in the side of your rib cage.

Self-motivation over external motivation.

Final Thought

I hope to never see my boss’s yellow teeth or smell his horrible seafood breath again. But if I do have to call him up and ask for my job back, then at least I’ll know it’s because I managed this list poorly.

If you love your job then stay there and send me a smiley face emoji. There’s nothing wrong if you already love what you do 🙂

But if you hate the idea of a job then build a side hustle after hours that can replace your salary. That’s the smart transition path.

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Most People Quit Their Jobs Only to Be Enslaved by a New Type of Boss

New type of boss

Photo by Ubiq on Unsplash

Right now I am a scared little man.

People think I’ve gone a bit nuts because I started a brand new Twitter account, set up a Substack, and joined Bitclout. They’re bang on.

I am scared. A lot of what I’ve built online has been centered around one platform: LinkedIn. I’ve been banned (accidentally) multiple times. When 7 years of hard work is at risk, you start to go a little bat sh*t crazy.

Recently I quit my job. That’s when it hit me. Most people trade their job for a fantasy they think is entrepreneurship, or freelancing, or a small business, or a startup, or whatever the heck you call making money online.

Maybe you’ve quit your job. Or maybe you’ve dreamt of doing it. This firsthand experience will save you from a giant pain in the ass. Let’s go.

The illusion of time freedom

I spoke to a friend recently. They quit their job in a big corporation a few years back. I imagined they must be really happy.

“It’s a nightmare. She won’t stop calling me. She wants it by Christmas.”

He now writes on various platforms and has a freelancing business. That lady is a client of his.

“She is worse than my boss. If I don’t do as she says then I can’t pay my bills. Remember: I don’t have a job. Ahhh.”

Does that sound like freedom to you? Nope. Personally, I want to sit at home in a jockstrap and watch finance documentaries. Call me crazy. Having a cranky old lady from the desert plains of outback Texas swear at me on a nice Australian afternoon feels like a death spiral into madness.

The algorithm slave life

My friend also relies on several tech platforms to run his content creation business. No matter what industry you decide to work in, you’ll face the same danger. If you’re not convinced then look at Gmail.

Did you know Gmail has an algorithm like Facebook’s that determines who does and doesn’t see your messages? Or what about the Newsbreak slave drivers? Okay, let’s not go there 🙂

At the start it’s hard to escape the algorithm captors that seek to maximize their profit, not yours. Jovan Cicmil runs an online course business.

If you rely on one platform to promote your work, then you are at the mercy of that platform’s algorithm. And let me tell you as a software developer: algorithms are fickle creatures, especially ones that use tens or hundreds of parameters.

One wayward line of code by one solitary web developer employed by the platform can ruin your entire business plan. One decision by a chief something officer can do the same.

The algorithm is like a boss. Follow its hidden rules that nobody knows. Accidentally break the algorithm dictator’s rules, and you’ll be punished. Unlike real-life where you go to a court of law and face trial, in algorithm land there’s no trial. There’s no innocent until proven guilty.

A high-fiving tech bro in a startup t-shirt with a Starbucks cappuccino in one hand and the keys to your entire life in the other hand makes a decision. They make lots of these decisions so they want your digital execution over quickly.

Most of the time they push the red button to throw you out like trash. There’s no phone number you can call to talk with them. Platforms don’t have humans that answer phones, only programmed robots in human skin that couldn’t care about your livelihood. Sell ads. Make money. Dominate the world. Do no evil (or is it do evil but don’t get caught?).

The algorithm is a modern-day boss. Some would say they’re crueler than a bad boss in a pinstripe suit with a huge ego. You decide.

The simple answer to hidden bosses that enslave us

A mentor of mine said to me once “if you can’t package it all up and sell it as a business then you’ve bought yourself a job.”

That’s what many of us do. We create something outside of our 9-5 job and then one day do it full time. It feels like a dream until we realize that if we’re sick for a few days then the whole thing can’t run without us. That’s not a business. That’s not time freedom. That’s not the life you expected to transition to.

There are three ways to quit these pain-in-the-ass bosses.

Smart diversification

I need algorithms for the time being. Because I can’t trust any of them to serve me like a loyal human, I cheat on them with multiple algorithm girlfriends. That way if one of them dumps me then I’ve got a new one to love.

Find a second algorithm until you’re established enough not to need them.

The breaker of slave chains

Financial assets aren’t bosses. Although if you become a landlord then you’ll meet the other type of boss: tenants.

The way you avoid digital enslavement is to make money and buy financial assets. Over time they grow and help you to care less about what XYZ tech platform is doing, or what your client’s next book they want you to write will be about.

Financial assets help you say “screw that” to yourself, quietly.

The hidden enhancer of time

Twitter has been a big part of my diversification. It’s an old app many people don’t get. I’ve seen multiple firsthand creators build 6-figure passive income streams on the platform.

Their strategies are so stupidly simple it should be criminal. I’m not going back to Twitter with a brand new account for the money, though. I’m going there because I love Twitter Threads.

Passive income is the ultimate way to avoid these new forms of horrible bosses and enhance how much free time you have. Passive income is the easiest to generate on the internet. Here are some examples:

  • Online courses
  • Affiliate links
  • Membership communities
  • Paid newsletters (Substack)
  • eBooks
  • Paid templates
  • Cheatsheets to popular apps like Notion
  • Youtube videos with ads
  • A website that generates traffic that can be monetized in lots of ways

Move away from bosses with passive income. Then you can say “thanks but no thanks matey.”


The key isn’t to never use a tech platform with an algorithm or to avoid every client. No. The key is to be aware of how algorithms and clients can become a type of boss if you don’t pay attention.

A millionaire Youtuber who only gets paid by Youtube is an employee, not a person who has all the free time in the world and can do whatever they want. This point is often missed.

Don’t trade a 9-5 boss for clients or the algorithm equivalent. Oh, and don’t trade your life in to become a debt slave to a bank either if you can avoid it.

What do I suggest? Have a website you own as well as multiple algorithms that expose your work to new people. Replace clients over time with passive income from digital products and services. That way, you can say no to clients or only work with the ones that treat you like a sweetheart.

Then when you’re successful enough, follow the path of some of my favorites — like Ryan Holiday, Mark Manson, Tim Ferriss — and divert everybody to a website you own and control. That’s how you don’t trade one boss for another, and buy back your time to explore your true creativity.

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People Fail at Side Hustles Because They Don’t Understand the Only 4 Roles in the Creator Economy

Side Hustle Success

Photo by Anthony Fomin on Unsplash

The power of doing only one thing is often neglected.

Shaan Puri is a great example. He sold his side hustle to Twitch for $25 million. Then he went on to invest in startups like Lambda School that is replacing universities.

He wrote about one particular week recently. The outcome for the week was to go deep in the new field of Web3. “I learn by doing” is the reason he gave for canceling all meetings for a week.

The result is he came up with a powerful metaphor. His metaphor says there are only 4 roles you can play in any field.

1. Skeptic (on sidelines, judging everyone)

These are the people guaranteed to fail. Sinem Gunel says “haters mostly hate because they’d like to have what you have.” Haters are skeptics in disguise.

Because they haven’t done it, they don’t want anybody else to. They want to stay in the land of mediocrity. It’s super easy to be a critic. You just sit your lazy ass on the couch with a laptop or phone and fire off comments to anybody who’s doing better than you.

Skepticism is a form of procrastination.

Why fix YOU when you can be a skeptic for free? Plus it’s fun. The internet loves skeptics. The plague of skepticism content can even earn you a tidy living on platforms like Twitter. I’m harsh because I used to be that skeptic.

In the early 2000s people told me you could make money online by setting up eCommerce websites. I was too afraid. I blamed the need to ship goods that could get damaged and collect payments via ‘risky’ credit cards as my excuse for sitting on the sidelines.

After work I’d go on Youtube and leave terrible comments on videos that talked about “making money online.” I even collected a few loser friends in the process.

If you think selling yourself or anything else is a pyramid scheme or a ponzi scheme or network marketing, then you’re not ready for side hustles. That’s the harsh truth.

A side hustle requires an open mind as the entry criteria.

You can’t be afraid of sales either. Sales is marketing, marketing is persuading, and persuading is a basic human skill that you do whatever your role is in society. It’s all just labels. You have to convince people to care about your side hustle. There’s no way around it.

Heal yourself of whatever you failed at before that made you a skeptic. Then move through the next three roles.

2. Cheerleader (on sidelines, cheering other people doing things)

This is a cool place to be. You’re not ready to start a side hustle yet. No problemo. You’re just cheering for other people who are while you figure out what you want to do.

None of us come out of the womb with a side hustle idea in our blood. I procrastinated on my writing dream for a long time. I watched from afar. I read a lot of other writers. I tried to emulate them. I left them thank you comments. Cheering doers is a noble sport. It’s better than tearing people apart out of jealously or because of daddy/mommy problems.

Doers build the things we use. Start there.

Be inspired before becoming motivated to start your thing. The people you cheer for along the way will be happy to help as a thank you, too.

3. Participant (in the game, using stuff other people created)

I shouldn’t admit this but I’m here right now with Web3. I’m a cheerleader of the movement and in the game, although I haven’t created anything yet. The truth is I don’t know where to start.

Where’s a good place on Web3 to publish content? Who are the people to follow? What projects, besides the obvious ones, are good to go deep on? What Web3 game should I play?

So I will use stuff other people have created until I figure it out. Then one day I will pivot part of my side hustle towards Web3. Until then I simply participate in the ecosystem. You’re probably similar. I doubt too many of you have built dApps or published content on a Web 3 blog with a .eth domain name. Makes sense. Much of the space has only been around for a year.

Using stuff other people created is how you figure out what you want to build. Despite what critics think, there are no original ideas anymore. As creators we’re all borrowing from each other. Author Austin Kleon said it best: “Steal like an artist.” Hell yes my man. Steal ideas we will.

4. Player (in the game, creating things yourself)

The more you create, the more powerful you become. The more you consume, the more powerful others become.

— James Clear

Your side hustle succeeds when you become a creator and that’s how you unlock the power of Shaan Puri’s metaphor. In the area you want your side hustle to be, how much did you create versus consume today? That’s the big question.

A side hustle is born through creation. You have to conduct a bunch of experiments to figure out what path you will take. Your path will be different from mine or anybody else’s. It requires you to face rejection, something many skeptics stuck in a death spiral leading to nowhere don’t get.

You can get rejected once and become a skeptic who calls everything a scam, or you can get back up and try again.

Ayodeji Awosika says it perfectly: No can mean be more creative.

It doesn’t mean “this side hustle doesn’t work and you should give up like a sucker.” Rejection is redirection. If this doesn’t work, try again. It’s the mantra of an entire side hustle generation that is redefining what work is on the internet.

If you don’t create you will never know what’s possible.

What’s guaranteed is anything is possible when you choose a side hustle and commit to it for 5 years. The skeptics won’t tell you that. They won’t tell you they gave up after 3 months and decided to call everything a scam.

It boils down to this

Success in any field simply means creating more than you consume. If you create for long enough, you’ll eventually succeed through experiments and the inevitable iterations that follow.

Don’t give up. Create more. Change direction.

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