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Career Cheat Codes I Know at 36 That I Wish I Knew at 26

by | Oct 24, 2022 | Startups

I got trapped in a finance career like a caged lion.

Then through a bizarre series of events, I invented my own job. This led me to get access to uncommon opportunities and build an online business that eventually replaced my job.

These are cheat codes that allowed, what some call a miracle, to happen. Steal them & apply the lessons to your career to get an unfair advantage.


1. Make your boss’s job easier

I’m not talking about kissing your boss’s sexy legs or anything.

Early in my banking career I got a new boss. He was in over his head. I could see it. So I told him to send me the hard stuff. Then I did the work for him and said “put your name on the bottom and don’t mention me.”

When he got too busy I went to his leadership meetings to ease the load. As soon as bonus time came around I got lots more money. Whenever I needed a favor I always got it.


2. Trade non-financial poker chips

Employees think the most about money. When they do good, like a doggie, they want their fat cat salary increase or bonus.

There are so many better things you can trade with your employer/boss instead of money — which makes them easier to get approved.

One boss gave me a day a week to hang out with the team that ran social media at my company. I learned so much from them which helped me become a blogger. Those skills have now earned me more than 7-figures.

Access to new industries/departments/information is worth more than money.


3. The path to follow that isn’t obvious

Society teaches us (wrongly) to follow the path with the most money.

That’s why many people become doctors, lawyers, and bankers. Not because their hearts desire them to, but because it sounds good and can pay well. The path to follow though, which leads to career happiness, is to follow your curiosity.

On the other side of curiosity are types of work that will stimulate you. Mine was writing online. Yours could be some other bizarre pursuit.


4. The least risky career path is a nightmare

Many of us choose jobs that pay a salary because there’s an illusion of security. I did this for most of my career.

A salary has the most risk though. Once you get comfortable in a job your ability to deal with change deteriorates over time.

Then one day your cool, hipster employer with ping-pong tables and coffee machines faces hard economic times and lays you off.

That’s when you learn how disposable you are.

Careers where you never take a risk lead to regrets. You’ll wake up one day and wish you did something else for work. But it will be too late.


5. Business is about who has the best story

Solutions, right answers, great ideas — they’re a snoozefest.

The person who wins in business has the best story. The story is what makes a manager hire you. The story is what makes a startup successful. The story is why customers buy products.

Get great at telling stories.


6. Put your career in brutal context

All the bonuses and corner offices sound great in the moment.

But when you’re dead and your grandkids are looking at photo albums of you, they won’t give a sh*t. Neither will anyone else.

Stop piss-farting around and do work that makes a damn difference.


7. Career plans = career p*rn

Everyone’s got a great career plan until they get laid off.

I’ve seen people in my career sit there and map out the path they’re going to take. It all sounds fine.

They know they’re worth more than they get paid but are afraid to try another employer. Or they stay put and believe the lies of the HR puppets.

All they have to do is wait.

They’ll get chosen. A promotion will come up. Someone will see their greatness. A few more years. One day.

These people wait for something that’s never going to happen. If it’s not happening now then make a new career path happen.

People tell you what you want to hear to delay your career dreams. But the market has the incredible power of giving you new opportunities and experiences when your current employer isn’t ready — or is lying.


8. The #1 sign of a successful career

You don’t know what day it is. Monday feels like Saturday night fever.


9. Never work for a weak leader when you can work for a strong leader

Weak leaders live in fear. They micro-manage. They do leadership performance that looks like work, but is nothing more than mediocre middle-management behavior.

These jobs are slowly dying.

Get around a strong leader. Learn from them. Then become them. Leaders get all the best opportunities in business. And even if your job title doesn’t include it, it doesn’t matter.

People don’t need permission to act like leaders.


10. The point of a job is to learn

When a job teaches you new skills you earn more money. If you get really good at business you can even leave to start your own.

Skills learned over size of salary.


11. Motivation over credentials

If you ever become a hiring manager, choose the positive person with more motivation over the person with the best credentials.

Credentials come from doing the same thing over and over, which often lacks creativity. Many credentials are earned through memorization instead of inspiration.

And credentials can even be bought with money.

But a motivated person has energy. They’ll take noes and turn them into yeses. They’ll see rejection as misdirection.

That’s the badass you want on your team.


12. Don’t get stuck in the passenger seat on the road to nowhere

Most people get certified and then join a company ladder. The ladder has fixed, unclear guidelines with all sorts of long-ass timelines.

The longer you do the job the harder you work. You’ve gotta become a yes mam! momma’s boy/girl. Then you suck up to your boss to get ahead. The whole strategy is built on eat, hope, pray, love your boss.

That’s no way to live.

To get into the driver’s seat you have to go from minion to CEO. You get control back of the steering wheel by writing down goals, taking risks, shopping for the best career deal, and building your own thing on the side.

Otherwise you’ll drown in mediocrity by being stuck in the passenger seat — always watching the action, but never getting to do anything noble, while being paid a peanut salary.

Stop relying on the pinstripe suit weirdos.


13. The saddest part of a career is stagnation

It’s where good people go to bury their careers.

Change jobs. Do secondments. Take risks. Change employers like you change underwear.


14. Lazy people hold a lot of meetings

Avoid these people like the plague.


15. Work only feels like work when you can’t stop thinking about something else

So do what you can’t stop thinking about every day for a job.


16. Try this career paradox for yourself

Many employees tell themselves they’re not qualified, or they need more experience, or they feel like an imposter.

They self-reject.

Your career only grows when you start taking the opportunities you’re not qualified for. If you get a new job and are a master on day one, you chose comfort not growth. This leads to an eventual career disaster.


17. The most courageous career act one can achieve

Everyone has the opportunity to start their own business.

Yes, most people will fail at it … but that’s not the point. Betting on yourself is a big deal. If it doesn’t work out you can always get another job. If it does work out you’ll never look back.

Always choose courage.


18. Stay the heck away from red tape

Many companies are drowning in bureaucracy. Nothing ever gets done and it rots your soul. If your company can’t do basic tasks like approving a $4 latte expense for a customer, runnnnnnnnnnnn.

Execution thrives when bureaucracy takes a back seat. And execution produces results that help you build a successful career.


19. This career skill is a rare diamond

When I worked in tech everyone drooled over technical skills.

But the ones that got ahead were those who had the skill to figure stuff out on their own. Independent problem-solvers get paid more than technical memorization gurus.


20. The career backup plan everyone needs

Side hustles are a naughty idea.

If your boss finds out they could fire you. If you tell people on the internet about a side hustle you might get stones thrown at your pretty face.

Side hustles have nothing to do with being cool. Without one you run the risk of being fired with no other source of income. In a deep recession with no end in sight, that’s a dangerous position to be in.

Build an online side hustle to de-risk your career.


21. Fact: Your employer doesn’t give a crap about you

You are a human resource designed for an employer to extract the maximum profit from, so the CEO can get rich and shareholders can make enormous returns off your labor. It is what it is.

So don’t tie your identity to a dumb job that can be dead tomorrow.

Spend your career hanging out with people you like working with, doing work you enjoy, trying new experiences, and having fewer regrets.

That’s how you retire one day & make it to your deathbed a happy human.

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