Category : Startups


Every Successful Leader You Know Has Experienced (At Least) One of These Massive Setbacks

Successful Leaders

Photo by David Huck on Unsplash

On day one of a new job I feel like a fraud.

My smile is fake. My palms are sweaty. I run to the toilet a lot for fear poos.

Basically, I have no clue if I can do even 20% of what’s in the job description. I wing it. I tell the hiring manager what they want to hear so I can pay for my shelter. I return home each night to my bat cave, thinking “what the hell have I done?”

It lasts about three months. Then I’m sweet as.

In my last job people thought I was hitting home runs every day. They couldn’t lift the veil and see inside my head full of fear. None of us can. Leaders look like geniuses — until they tell you the truth about their careers.

Every successful leader you know has experienced (at least) one of these seven massive setbacks.

1. Taken a new role and felt like an imposter

Leaders take roles they’re not qualified for all the time.

My old boss used to say, “every leader is trying sh*t on to see what sticks. If they get away with it, then great. If not, they’ve lost nothing.”

The challenge is you can fake your way into a new role. You think you’ll learn as you go, but not always. Sometimes the leaders at your new gig need results straight away. They don’t have time for you to learn.

When they realize they’ve been oversold they put you under enormous pressure to get to the truth. Your career can fracture into a million pieces from all the pressure. They’ll either get rid of you, or force you to step down or cop a demotion.

It’s better to oversell and fail than undersell yourself and go nowhere.

2. Been betrayed by another leader

Workplaces are a game of thrones battle.

When you’re a leader you’ve got supporters and haters. There is always politics to navigate. Everybody has their own agenda. Whichever leaders get their agenda done, wins the prize: a fat cat bonus.

Through the process there’s always one sly bastard that betrays you. You think they’re on your side. Secretly they’re talking smack about you to the big bosses to get you in trouble — normally, so they can march in and take your leadership gig right off your hands.

Leadership politics is a nightmare. It’s one reason I quit working a job forever.

It sucks to get betrayed, but humans let each other down. Expect it so you don’t get wrecked by it.

3. Worked an entry-level job

I started my career at 12-years-old working in the local pizza shop. I later got a promotion to work in a hotel. Scandalous couples would rock up to reception all through the night and try to look innocent.

They were there for a naughty time. I had to keep a straight face and pretend I had no idea why they wanted a room at 1 AM.

We all start in humble beginnings.

Every big shot leader you know worked their fair share of entry-level jobs too. It can feel like a setback when you work one. You can feel like you’ll never get anywhere. Even worse, if your career explodes (like mine did) you can find yourself back in an entry-level job.

There’s a huge advantage: when you’ve worked entry-level jobs, it helps bond you better to frontline workers that do the majority of the heavy lifting.

4. Battled mental health issues

Take one look at LinkedIn. It’s clear since March 2020 that mental health issues are common amongst leaders. Unfortunately, mental health is still seen as a career weakness. I’ve been told to shut up about it plenty of times.

Make no mistake. Anxiety or depression has affected ever flawesome leader. They just don’t talk about it. I wish more would.

Talking leads to healing.

5. Felt like giving up

As the leader there’s nowhere to hide. You’re accountable for the results.

Sometimes the goals you’re set are nothing more than wishful thinking. A group of strange folks in pinstripe suits make random decisions about an idealistic revenue number or target.

This happened in 2020. My boss told us that we had to exceed targets. We explained that coroni-macaroni might make that hard. We got ignored. We had to tell leaders stupid stories about revenue that would never happen.

Meanwhile our competitors lowered their targets and focused on building goodwill with customers through honesty. They later thrived. We got hit by a leadership freight train. Leaders’ heads rolled.

It’s normal to feel like giving up at some point. The key is to persist. The truth eventually surfaces. Mother Nature takes out the trash.

6. Been rejected for multiple leadership roles

I’ve known many successful leaders that took a redundancy. I thought they would get a new job fast.

Only once you have behind the scenes conversations, is the truth revealed. Leadership roles are hard to get. Many people want them.

The best leaders only get hired because they can pass the minimum threshold of rejections needed to succeed.

7. Experienced personal tragedy and not wanted to go to work

I went to work many times right after I said goodbye to dead people. You’d never know it. I could act my way through it (mental illness teaches you).

The most successful leaders are where they are because of the tragedies that shaped them. Tragedies are inspiration that leads to an unusual form of motivation for a team. Tragedy extracts all the normalcy from your brain and spits it into the gutter.

Never forget …

  • Leaders get cancer
  • Leaders go bankrupt
  • Leaders lose loved ones in tragedies
  • Leaders give birth to stillborn babies
  • Leaders get addicted to illegal drugs
  • Leaders gamble away their life savings

Leaders aren’t special, they just look like they are. They’re like you and me.

It all boils down to this

People at work look like they’re winning

It’s all an act.

We’re all trying to make it through the day. We’re all uncertain about the future. We’re all scared out of our minds.

Don’t let corporate marketing or LinkedIn make you think any leader is winning every day.

We’re all just figuring stuff out as we go.

Career fear is normal.

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You Can Still Rebuild Your Career After These Common Tragedies Occur

Common Tragedies Occur

Photo by Ulrich Derboven on Unsplash

He was the envy of 40,000 employees.

You’d see his face on the company intranet. He won all the career awards. He got a fully paid trip to an exotic location each year as part of the star performer program. The Chiefs were grooming him to take over the finance industry. One afternoon I came to the office.

“Hey, he hasn’t been around for a few days. Where did he go?” I said.

“Oh, he got demoted and moved to a regional office out in the sticks.”

I didn’t see him for a year.

The public demotion was the talk of the office. Everybody laughed at him. They wanted him to fail because of his perfect career record.

A year or so later he reappears in our office. He joined my team. It felt strange because he used to be a “Head of” and now he was a frontline pleb like me. We were the rats that dealt with the customer. We got paid peanuts while our bosses sipped lattes and did Facetime calls with their kids in private schools.

I liked the guy. What happened in the past rarely came up in conversation. He got on with the job. He knew there were judging eyes everywhere. Yet he stayed strong and wowed his little patch of customers.

After several years of slaving away he disappeared again.

“Where did he go this time?”

“Oh, the black and yellow logo snapped him up. They promoted him up three levels and gave him a massive pay increase.”

It turned out I wasn’t the only one watching. One of the more quiet managers had seen what I’d seen: a resilient son of a gun. That manager changed employers, and took the effort to recruit him.

None of my colleagues were laughing anymore at his demotion. He went from hero to zero and back to his rightful place.

A public demotion is a career tragedy that you can come back from with the right mindset.

The loss of a loved one

When someone close to you dies, it tears your career apart. 

Yesterday I saw a post on LinkedIn from Tim Jones. He announced his retirement from the world of work. About halfway down I noticed this wasn’t a typical retirement.

One thing I did not see coming was a recent health diagnosis: I have a terminal cancer which has no available treatment.

My oncologist has estimated I have less than 12 months to live. This clearly focuses the mind, and so I have decided to spend the time ahead with family, some close friends and make 2022 the best it can be…

So that I don’t get left in digital limbo, will also shortly be deleting my social media accounts.

One can only imagine what this health crisis means for Tim. His family will get left with a big hole in their lives after he passes away in approximately one year. They will have to learn to rebuild their careers after the tragedy.

And they will rebuild.

It will hurt like hell. Then they’ll think to themselves, “What would he [Tim Jones] of wanted us to do?”

The answer will be obvious. Move on and let his spirit lift them up.

Crippling mental illness

Mental illness could have destroyed my career.

I distanced myself from all work events and meetings wherever possible. My team leader thought there was something wrong with me. I didn’t have the kahoonas to admit my dark secret. It stuffed up my career for years until I eventually got help.

The mental torture ended up being the best thing that happened to my career. The story became an inspiration for my work colleagues. My company embraced the fact I was willing to share the journey online.

No doubt it helped some people. Only a few have revealed themselves to me over the years and told me, how that vulnerability to share, helped them with their battle.

What doesn’t ruin your career can become a defining period of growth when you consciously use the situation to help others in business.

Going through divorce

A divorce becomes an avalanche in your career that can tear down all of your daily work activities.

You can feel like crap. You can stop caring about everything. You can say things you shouldn’t. You can let frustration dictate your actions in the workplace.

When my boss’s boss got divorced a few years ago it ripped her life apart. One afternoon my colleague let her know he’d be leaving the company. They’d worked together for a decade. The departure was expected.

She broke down crying in the meeting room.

Unfortunately for her the meeting room was a fishbowl office and all of us could see. She got fired shortly after because she lost a Game of Thrones duel with the other senior managers.

She ended up unemployed for a year. Her ex-husband took the two kids. She barely got to see them.

The woman that used to inspire me looked like a different human being. None of us knew if she’d ever get a job again. We tried to put in a good word for her, but the brokenness showed up in every job interview.

Then I got a new job. Two months in I noticed her walking the corridors.

“Strange to see you here. You got another job. Congrats.”

She got counseling. She repaired the damage with her husband and he allowed her to see the kids again. Her infectious smile came back. This time she took a job that was several steps below her old one.

“I’m not that person anymore. I’m going to reskill and apply for jobs in a different field when I’m ready.”

She’s now in a new job, higher than where she has ever been. She rebuilt her career better than before.

A divorce shows you what you’ve been neglecting. With that new perspective you can rebuild.

Going bankrupt

I’ve worked with several bankrupts over the years. It almost always comes down to one thing: they took too much risk.

When you can’t pay bills or rent it really disrupts your life. It’s hard to have a side hustle, go to the gym, have a killer morning routine, do yoga, meditate, or drink green smoothies.

You’re just trying to get by.

As a result, money becomes your primary focus. The difference is whether the person gets the lesson from their bankruptcy or ignores it. Whether they blame the world or take personal responsibility determines if they will rebuild. Many of them do.

They rebuild their finances to a higher level than before.


Because they learn about proper risk management. They stop taking dumb risks to get rich off a dog coin.

Getting fired

A good ol’ fashion firing can happen to anyone. It’s happened to me. It right hooked me in the mouth. I felt like garbage for months. I felt worthless, used, abused, and angry.

The best revenge was to get a job twice as good as the one I got fired from. It wasn’t easy though. It took months. I got more rejections than expected. The career gap messed up straightforward job interviews.

With enough determination you can reuse the negative energy and turn it into momentum. I’d go into interviews like a tiger ready to kill. I’d overprepare. I’d be a little more humble, thanks to the firing. I wouldn’t take no for an answer. I’d follow up like a golden retriever.

A firing shows us we’re disposable. We become wise. We see through the corporate fakeness and get down to business. That rebuilds our careers.

The magical trifecta

This part sucks. You can cop the career tragedy trifecta: get fired, lose a loved one, and suffer mental illness (perhaps even lose all your money at the same time, too).

Don’t mess with these folks.

When three tragedies occur all at once it rewires a person’s brain.

The enormous loss gives them laser-like focus. They get to the point. They ignore critics. They act like they’ve got nothing to lose (because they haven’t).

These individuals don’t just rebuild — they transform. They become superhuman. I wouldn’t wish this trifecta on anybody. But if it happens to you, get ready for the pot of gold at the end of this magical rainbow.


You will fall down in your career, that’s guaranteed.

The question is whether you will get back up. My advice is to try. It won’t be easy but it will be worth it. You’re good enough to rebuild your career. So when it happens, you know what to do.

Enter your monk mode and rebuild.

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The One-Time Customer Mindset Demolishes Many Online Businesses

Online Businesses

Photo by Aziz Acharki on Unsplash

Transactional relationships are the dumbest way to make money.

A customer can buy once, or multiple times from you. A person who never gives you a dollar is one of the best people you can ever meet in the online business world. Let me explain.

The dumbest company in the world

I recently tried to get a website built. The company sold me the dream. I fell for it like a sucker.

Halfway through they started talking about profitability. They said they couldn’t make every customer happy because they’ve got to meet minimum profit margins. So rather than try to make me a happy customer, they simply raised their quote by a lot after they already agreed on the price.

The goal of their business is to screw each individual customer for the maximum profit. They’re profit-focused like the typical corporate juggernaut. Because they rarely have happy customers it requires them to always go back out to the ridiculously competitive market for selling websites and run Facebook Ads to attract more suckers like me.

Ad-driven businesses exist because they don’t understand the magic of referrals.

Underneath the iceberg of every customer is millions of dollars

My website company saw me as a one-time transaction. Those who know my work know that I have a massive community of content creators.

Many of them have done my courses — and lots of them need, right now or later on, a good-looking website. I get asked all the time about websites.

To date I can’t suggest any good providers. Template websites don’t convert traffic into customers. Custom websites are the best option but that requires you to know a person or company that can build a good one. Most of us don’t.

Most of us get screwed because we trust an amateur based on fake testimonials with smiling imposters.

Imagine if this website company that saw me as a one-time transaction knew I was a single sale with more than 1000+ possible referrals — all with zero commissions and no Facebook Ads needed. I could fill them up for years with work. Yet they chose to focus on making $200 extra of profit rather than deliver a job they admittedly stuffed up.

See people, not dollar signs

There’s nothing that kills a business faster than treating humans like numbers. That’s why I hate too much automation in my business. When all you do is send a series of automated emails like a lazy ass, you show email subscribers you don’t care about them.

You build robo relationships, not genuine human relationships. 

That’s how most online businesses operate.The person on the other end of your marketing emails simply switches off and unsubscribes. 

Can you blame them? Nope. When you get to know people they see who you really are. That connection unlocks a form of trust. That trust leads them to refer people they know to your online business later on. I don’t say this as an amateur either.

A large number of people who buy a course from my online academy come back for a second, third, and even fourth product.

I previously worked with thousands of online businesses in my banking career. I got to see all their customer data, and I’ve never seen as many repeat customers as I have somehow managed to get in my business (not to brag).

How to unlock the magic of customers that refer

When a customer is happy they can’t stop themselves from sharing your business, name, and products with everybody they know. Think about businesses you love. It’s true isn’t it? Try these tips.


I don’t sell crap. I do loads of research. I collect data through surveys to make sure my imagination isn’t running my business. (Many online business owners live in a fantasy land.)

When it comes time to build a product I spend months to get it right. No corners are cut. Quality over quantity is the focus, even if it takes longer. I tell people what they’re going to get. I always add in more than they were promised as a nice surprise.

Look at the lifetime of a customer

One transaction might go bad. One transaction might make no money. I don’t give a sh*t. What I care about is caring. If somebody decides to part ways, I leave them better than I found them with a gift they didn’t expect.

Some of those departed customers never bought another thing. Their friends and connections did though.

Think about how many referrals are hiding under the surface

Every person that buys from you is sitting on a mountain of referrals.

Referrals cost $0 to acquire. It’s the compound interest you get paid for doing the right thing and not being a d*ck.

The trick is once you overdeliver on your promise, you have to ask for referrals. Some will flow naturally. Others will require you to extract them like mining for gold in the desert. That’s okay. Ask. Ask again. Ask “why not?”

Give free stuff away

I like to add free upgrades to paid products later on. Customers don’t expect it. I also love to make 90% of what I do free. Anybody who is on my email list will tell you how much free stuff I give away.

My motto is this: only charge money if you have to.

If I can live for the next year without asking for money then I will. The need to extract money from every person is a disease, not good business practice.


Don’t be like the website company that treated me as a one-time transaction. Not every customer of your online business will be profitable. Not every person you meet online will be your customer. Doesn’t matter.

Treat people like humans, overdeliver, give more than you take, do free (a lot), think with abundance, and for the love of god, don’t forget the hundreds of referrals hiding beneath the surface of every person you encounter.

Dumb online businesses are forced to use ads. Smart online businesses harness the power of referrals to make money while they sleep.

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Traits of a Non-Sleazy Salesperson Who Leaves You Stunned

Non-Sleazy Salesperson

Photo by Shayan Rti on Unsplash

The world of sales can be revolting.

Not with her though. She had sass, personality, and quiet confidence. We arrived at the customer’s office at the exact same time.

Our boss called us “B1 and B2.”

She let me open the meeting. I spoke about the impacts of blockchain on the insurance industry. A bit of a snoozer to be honest. Then she asks the client to speak. They go into their biggest problems.

She sits there and listens. She occasionally asks questions. The customer reaches the end of their explanation. My colleague gives a careful playback. She’s able to filter out the signal from the noise in real-time.

Then a careful pause.

“Is it okay if I share some thoughts?”


She goes on to explain our philosophy as it relates to them. There are no cheap sales lines. She doesn’t brag about what we do or any services we may offer. The focus quickly goes back to the customer. Over the next three weeks she takes them on a journey.

No asking for money. No prices. No biased opinions.

At the end of the three weeks she refers them to another provider to assist them. That company is our major competitor.

I’m in shock.

All that work to simply handball a freebie to our competitor. That same competitor annihilated us with another client.

“Why’d you do that?” I asked.

“It’s the best option for them.” *Smiles*

6 months later that same client came back to her at the start of a new financial year. They had a different opportunity unrelated to blockchain. Without hardly any negotiation we got the entire business. She made her annual KPIs for the year at the start of quarter one.

Nobody knew how she did it. I got to watch. It left me stunned.

It’s always about the customer, not what she can sell.

Basic sales skills are a survival technique

Maybe you think sales is BS. Unfortunately we’re all born as salespeople. Sales is the ability to persuade and influence other humans.

If you can’t do that you’ll never get married, have a kid, get any type of job, or effectively use social media. The great news is you’ve already achieved one of these goals. Congrats.

Sales is a survival skill to help you get what you want. But first you have to help other people get what they want. The first trait of a non-sleazy salesperson is the ability to put their needs second, the same way parents do for their children.

Here are the other sales traits to adopt.

Ask for money when the time is right

Sales is often seen as sleazy because in the business world it involves asking for money. Money is how you buy tacos and put a roof over your head. Let’s flip the idea of sales on its head.

You’re doing people a massive favor when you charge money.

When you help people for free you’re destroying their potential. It never works. Why?

When you don’t charge people money for what you offer they have zero commitment. Money is accountability. And people need to be accountable to have you solve a problem.

Once a person decides to get your help, nicely tell them how much it costs. If you take time to understand their problem properly they’ll be glad to pay you.

Feel good when you make a sale

There’s no need to feel guilty for getting paid. Maybe you solved a person’s problem in 30 minutes. That’s not the point. It takes you years of experience to be able to do that.

People pay for value, not time spent — Sahil

Understand that most execution in life boils down to this

When you sell an idea that’s only step one. Many people stop there or they think there’s no more to be done. They wait for something to happen. They get angry when nothing happens and play the blame game.

Non-sleazy salespeople follow up. The difference is they do it without being a pain-in-the-ass.

Results happen from follow up. After working in sales for most of my life, I’ve only seen a handful of times where a person buys a product, service, or idea from someone after the first time they explain it. That’s fantasy land. Humans need time to think. Let them. Then follow up to hear their thoughts.

Explain once. Follow up politely 3-6 times over a number of weeks.

Use Twitter to talk with hard to reach people

Non-sleazy salespeople are creative. They look for multiple ways to get in touch with people they want to sell an idea to.

Email is the worst.

Lex Fridman is one of the most interesting podcasters in the world. In a short space of time he built an enormous audience of listeners that requires the use of average sales skills. How? Most people don’t know — replies on Twitter. Here is Lex in action with Elon-Rocketship-Musk.

Screenshot from Lex Fridman Twitter

Contextual ‘asks’ of people’s time sells better than random out of the blue “can you give me something for free that I haven’t earned?” requests. Luck won’t sell anything for you. It’s stupid. Intentional asks are the smart way.

Get to the point (faster than you think)

Dunja Lazić got 60,000 signups for a new product as part of her non-sales job. She learned one huge lesson.

2–3 paragraphs is the ideal pitch. People can spot a mass email a mile away.

People don’t have time for 2000 words sales pitches. Write a long pitch for an idea. Refine it once. Wake up the next day and refine it again. Ask for feedback from a friend.

Yes, this process takes longer. But if you spend a bit more time with a sales pitch you’ll get 10X the results. Most people send pitches that never get a reply because they’re lazy with the process.

Effective selling to humans requires you to save the recipient time. Once you understand other people’s time your sales life will change. All of a sudden you’ll start getting a flood of yeses coming through.

Show proof of work before you ask

A non-sleazy salesperson puts in the effort before pitching. A sleazy salesperson seeks to extract value without proof of work.

I get messages all the time that say “how do I make money online?” That’s it. A pitch like this is pointless. If you haven’t even done a simple google search then you can’t expect a stranger to do all the work for you.

Whereas if a person says “I’m a writer. I’ve tried Substack, Twitter, Amazon, and Quora. None of the platforms have worked well.” And then they go on to explain (briefly) how they’ve gone about it, the question is more likely to get a response.

Nobody wants to get pitched by a lazy person seeking shortcuts and free help. The challenge is many of you do put in the work before pitching and simply forget to mention it. This is the reminder you’ve been looking for. Be like bitcoin: show proof of work.

Seek out others rather than wait for them to come to you

Non-sleazy salespeople do very little selling. They become a magnet for opportunities. How? Start publishing content online — videos, audio, illustrations/photos, writing.

Steal this formula from marketing expert Andrea Bosoni.

– If you write 250 words/day
– Every year you’ll publish 50 posts
– If each post brings you 10 visits/day
– Every year you’ll have 200k traffic
– If your traffic converts 1%/day
– Every year you’ll get 2k customers”

Nobody is coming for your work or idea. You have to become a magnet. Social media is a magnet. It attracts the type of people you can sell your type of idea to. Maybe that’s for money. Maybe that’s to serve a mission. Maybe it’s to help people in poverty.

Content sells better than cold pitching.

Content = Stories

Let most opportunities die

The point of sales isn’t to sell to everybody.

Most people aren’t right for your ideas and opportunities. Most of what we do doesn’t have mass appeal. Once you understand that, you let people go far easier to focus your time on those who want what you offer. Then the number of things you successfully sell goes up. Boom.

When you part ways with someone, don’t be a d*ck. Leave on good terms. They might come back later for a different opportunity or after their thinking has changed. The non-sleazy salesperson that left me stunned taught me that.

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“Not Experienced Enough” Is Job Interview Feedback That’s Completely Misunderstood

"Not Experienced Enough" Is Job Interview Feedback

Photo by Brett Jordan on Unsplash

The job interview process feels like death by a thousand paper cuts.

In 2019 I got fired from a job I loved. As it came out of nowhere, I had to quickly play the job interview game.

The feedback “not experienced enough” could have destroyed my career and sent me spiraling back into a life full of darkness and mental illness. I’m not the only one. Every day on LinkedIn I get messages from nice people.

The most common message is this: “I got rejected for lots of jobs. My life feels like it’s over.”

It really stabs me in the chest when I hear this.

You will hear “not experienced enough” a lot

Despite what you might think, this phrase is common. If Elon Musk went out into the job market tomorrow, he’d be given the same comment lots of times too despite his impressive work resume.

“Not experienced enough” is a default response.

When I’ve interviewed people for jobs in my career and needed to reject candidates, it’s an easy one-liner I’d pulled out too. Honestly it’s lazy. It’s one of those easy responses you give when, frankly, you don’t care enough about the candidate or your day is slammed with back-to-back meetings.

I feel guilty for saying it. I wish I could go back and care more for the people I was rejecting. When you get rejected for a job it’s your livelihood on the line. I’ve seen it too many times before.

There’s a limit to how many rejections we can take before we lose confidence and start to believe we’re unemployable. Most of us aren’t bulletproof Arnold Schwarzeneggeres running around town doing job interviews.

Rejections hurt our egos.

All it takes is enough attacks of our ego for it to tell us “you’re sh*t, give up you idiot.” Self-talk can be destructive. It can lead to a career downfall if you’re not careful.

Experience is based on opinion, not fact

Do employers and hiring managers really do the due diligence to check your experience? Nope. They might ring one or two referrals. These referrals are pre-programmed by you to say nice things, so it’s mostly a pointless exercise.

Occasionally you’ll get a smart cookie who will go on LinkedIn to check your profile for mutual connections. Then they’ll anonymously contact a few people who have worked with you to get the off-the-record gutter talk about you. This is rare. Most people with jobs don’t have time.

Your experience is judged in an interview. You may be representing your experience poorly and that’s why rejection happens. When I went through hell in 2019 and got told by potential employers that I wasn’t experienced enough to work in tech or didn’t know enough about banking or social media or sales, it hurt like hell.

One smart-ass woman from a tech giant even dared say, “you’re perceived as sh*t because you have a career gap. Good people don’t get fired or have employment gaps.”

I had to muster up every bit of strength I had not to rip her unfair, biased, rude, illegal, discriminatory comments to pieces and get her in serious trouble.

None of us have mind control powers though when we interview for jobs. We do our best. Sometimes that’s not enough so it comes across as a lack of experience. Really, it’s a lack of preparation or a misunderstanding of the FBI interrogation questions asked in the interview under enormous pressure (the pressure to get a job and pay bills that are mounting up).

Don’t let opinions destroy your career. Most of them are made in a hurry, without a care in the world for your well-being or feelings.

Experience is stupid. It’s based on the past.

I don’t get career experience. If someone had predicted the future of my career at 21-years-old based on my past, the only logical outcome you could predict was I’d become a crack addict.

Dark mental illness, violent friends, probably an alcoholic, always around drugs, lots of time working in nightclubs — all were signs that my life experience would produce a terrible future. That’s not what happened though.

What’s better than looking at experience is seeing someone for their potential.

Some of those people with the worst past experience are diamonds in the ruff, waiting to come out of their shells and unleash their gorgeous potential.

Experienced people often think they know it all. People with average or bad experience, but loads of potential, have drive.

Drive is a form of energy. That energy pushes through career obstacles. Someone with drive can hear no from a customer and keep going until they get a yes. Someone with experience can think that customer is a waste of time based on their prior sales history and let them go.

Drive is unstoppable. Drive is passion, thirst, hunger, and a mindset that says “get out of my way!”

You know who has loads of drive?

  • People who have been fired
  • People who have been unemployed for a long time
  • People who have been out of work due to cancer
  • People who have been mothers returning after giving birth

These are the same people cast aside by the business world as “not experienced enough” or “having gone backwards.”

What they miss is, when you go fifty steps backwards, you are able to go forward much faster than a comfortable person full of experience who thinks they know it all. Those career gaps fuel deep thinking and self-reflection. All of those job rejections form incredible amounts of humility that the experienced person can’t even contemplate.

The underdogs labeled as not experienced enough are actually high-performers waiting on the bench for an opportunity.

You’re reading an article from one of them right now. So many dudes in pinstripe suits told me I was “too entrepreneurial.” I stopped arguing with them. Here I am with no job and a successful online business. No one’s laughing now.

Here’s what you must do from now on to change your career forever

Do this: don’t give up until a person dares see your potential.

You don’t need everybody you meet in interviews and networking functions to think you’re a genius. All it takes is one.

I had one farmer see my potential early in my career. Everybody I told my failed startup stories to at work laughed. Not him. He saw something. He asked me to use those business skills to help launch a new department. So we did. The department run by the two of us and one other made more money than divisions at our employer with hundreds of employees.

All it takes is one. Don’t wait. Put yourself out there. Find that one person.

It all boils down to this

You’re only as experienced as you think you are. How you present yourself sells whether you are or aren’t experienced enough for a job.

And here’s the rub: sometimes people don’t want to see your experience because they have other ideas, like they want a mate or colleague to take the job you’re going for.

Biased people are in every single company. Incentives are misaligned. Just because you deserve a job or qualify for it, doesn’t mean you’ll get it. That reality is beautiful though. It means a lot of job interview feedback is completely useless.

Don’t let opinions drive or direct your career. Everybody has an opinion and it’s dished out not based on fact. Take feedback to improve. Don’t take it to heart.

The best job, anyway, is the one you have to work your face off to get. All of those rejections add up to an overwhelming feeling of fulfillment when you finally get the job you’ve been searching for.

Here’s how applying for new jobs works:

Not experienced enough.
Not experienced enough.
Not experienced enough.
Not experienced enough.
Not experienced enough.
Not experienced enough.
Not experienced enough.
Not experienced enough.

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Four Side Hustle Skills No ‘Guru’ Taught Me

Working without a boss sounds like a dream

Photo by No sense on Unsplash

Gurus are full of sh*t.

None of these making-money-online gods taught me a thing. Mind you, I’m not the smartest guy. I only learn from experience. The same probably applies to you. A side hustle that levels up your life has to be experienced to be understood.

All the online courses and blog posts in the world can’t replace a good ol’ slapping across the face that comes from realizing there are very few rainbows and unicorns in this style of work.

These are the skills you must have.

Working without a boss sounds like a dream

Gurus sell us the no-9-5 dream. Mostly it’s hyperbole. When I quit my job I imagined sitting in Starbucks cafes and doing morning yoga right after a green smoothie. The dream lasted about a week.

I quickly realized without a boss there is zero urgency to do anything. And if you’ve done okay financially and have savings, then the urge to work is non-existent.

Without a stick poking you in the back it’s easy to get lazy. I found that even before I quit my job and had a side hustle, my 9-5 work got done but my side hustle work could be a real struggle.

The first skill you need is to become your own manager. That requires accountability. I had to have weekly goals to have any form of direction. What stops you from becoming a Netflix slob is sharing those goals with a person you look up to. I shared mine with my partner. She asked me every day how each goal was going.

There’s one issue with goals, though: We often have too many. My goal list at the start was far too long. So I trimmed it back to one goal per day. Any other tasks that got done were a bonus.

Most people need third-party inputs

Traditional employers have robbed us of one of the greatest gifts in the world: how to think for ourselves.

All day at work I was programmed how to think. I picked up corporate slang and buzzwords from every person I worked with. Back-to-back meetings often involved lots of Powerpoint decks reinforcing the programming. My employer told us “we are great and we’re changing the world.”

Not really. Our value had eroded over time. We took our customers for granted and treated them like a line item in the black hole of a spreadsheet. Outside of company programming there was industry programming.

Software companies would host zoom calls every day and tell us how great their product was. They’d pretend they “do no evil” with our data but nobody really knows. Cloud computing is another black hole.

Then our customers would program us with their products and services. They’d invite us to events and make us wear their corporate t-shirts to reinforce their message. It felt like Sunday church, except nobody believed their gospel.

Whenever a problem arose at work there was a team of lemmings to flood the room with excuses and Powerpoints full of poorly designed solutions. No one ever said to me “you must solve this problem or you’re fired.”


A normal job spreads problems across more than one person so you’re pretty safe. It’s how people can stay in comfortable madness their entire career.

In the side hustle world it’s different. I had to learn to think for myself. When I received poor programming from businesses, people and products I used, it cost me big time. I realized a lot of people do what’s in their best interests not mine. I had to learn to see through the bullsh*t and improve at evaluating people and opportunities. I made plenty of mistakes but I got better at it.

Tim Ferriss taught me to create a pros and cons lists for everything. I got multiple quotes for services. I asked hard questions to people who wanted to work with me. I stopped living in a house made of pillows where I couldn’t hurt myself. Instead, I got some bruises and fell down on my knees enough times to make them bleed uncontrollably.

Three separate website companies scammed me. Conversations I had in private got leaked online. Partnerships came and went. Content platforms went up and down with their strategies, and with it, my livelihood.

The path to a successful side hustle requires you to think for yourself and form your own opinions. Otherwise, if all you do is take second and third-hand information as gospel, you’ll fall flat on your face due to the hidden incentives being against you.

A life of no risk teaches you to be skeptical. You have to undo the programming.

A job doesn’t have a lot of risk. If the worst event happens then you can always get another one. There are record numbers of employers desperate to hire you. I’ve done plenty of online learning when it comes to side hustles.

Not one guru ever taught me how to take risks.

Our brain is programmed to avoid risks to stay safe. This explains why so many people are professional skeptics. They grow up in a work culture where risks are mostly prevented.

Then they get out into the side hustle world and have to sort through the bullsh*t. It’s not easy. So they quickly give up and let their skepticism take over. They blame fake gurus as the problem when it’s really their lack of courage to take a risk and see what happens.

Three websites I’ve tried to build in the last year have failed. It’s cost me a small fortune. And I’m fuc*ing smiling. Why?

The lessons I learned from how not to build a website have led me to a place where I now know exactly how to build a website like a pro. In fact, the lessons could turn into a separate business.

When I worked as a senior leader for a company that sold websites, I’d see people in the same situation lose their marbles. They’d call their mommy and get their lawyer to email us if the website didn’t make them money.

They failed to see that creating an online business with a website is their risk, not the website company’s. So they got conditioned to see every website company as a scammer, when the problem was their inability to take risk and have it go bad.

A side hustle equals risk. Take small risks and let them blow up so you can build your risk muscle. The more risk you get comfortable with, the bigger your side hustle empire can get.

What to do with the success

A friend of mine created a side hustle that became wildly successful. He got everything he wanted and more in a few months.

It all led to several years of dark depression.

The entire business got left on a laptop in a foreign country to rot away. I asked him what went wrong. “I don’t fear failure. I fear success.”

When your side hustle has some success it can all go to your head. You can think your god’s gift to humanity. The first sign is you oversell yourself with too many asks. The second sign is you give thank you speeches to random people on social media, like you’re accepting an Oscar. The third sign is you start counting numbers of followers. The fourth sign is you create some cheesefest personal brand that makes grandmothers around the world vomit. I could go on…

The first time I made $50,000 in a month I became a giant a**hole. I told one female manager at work “I could quit tomorrow you know, I don’t need this bullsh*t. My side hustle pays five times what this lame job does.”

Success gets to our heads. That’s why it pays to have people who can knock you back down to reality when your head gets too big. I intentionally have people do this for me via a verbal contract. They happily do it.

The last skill you need is to invest the profits. I see people doing well with their side hustle every day. Then they tell me they blew the money on some random purchase or let it sit in a no-life savings account been eaten up by 5%+ inflation.

Take a large amount of the profits and invest them in financial assets. These investments will help smooth out the ups and downs of the side hustle game.

A side hustle didn’t buy my time back. A side hustle that funnels money back into financial assets did. That skill is never spoken about by the gurus, so their followers end up stuck on the hamster wheel to nowhere. You can do better.

This article is for informational purposes only, it should not be considered financial, tax or legal advice. Consult a financial professional before making any major financial decisions.

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