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Startups

9 Things I Learned Far Too Late in My Career

Tim Denning Advice

Photo by Leo Broadbent on Unsplash


Career decisions require my head to be WD-40’d.

It’s the hardest part of a career. Do you stay or do you go? Do you hop on over to the greener grass, or stay on the pee-stained grass you’re already sitting on? Or do you go and look for a new field of dreams to work in and become an entrepreneur?

While Bezos is not my buddy, his advice on career decisions is gold.

“All of my best decisions in business and in life have been made with heart, intuition, guts, … not analysis…it turns out in life that your most important decisions are always made with instinct and intuition.”

I wish this wisdom had struck me at 26-years-old, when I left a business behind that I loved, cried myself to sleep, and eventually, rejoined the workforce. Here’s what else I learned too late in my career.

The more perks, the more jerks

HR crazies try and lure “talent” with perks. Here are a few.

  • Unlimited barista-made coffee, or ice-cold kombucha
  • Ping pong tables
  • Arcade games like Space Invaders
  • Backpacks with business logos
  • Pencil cases
  • Chef-made lunches
  • A campus rather than an office
  • T-shirts with forgettable, minimalist logo design

Perks equal jerks.

Take a walk around a tech giant’s office. It’s not uncommon to meet a bunch of adult babies wrapped in privilege they can’t see. Perks attract entitled individuals — and they’re the worst ones to work with. You’ll be dodging egos all day long at work.

HR took the perks game to new levels. But you wouldn’t take candy from a stranger leading you into a dark alley, would you? Then don’t take the bait from HR politicians who will happily fire you if a senior leader says to.

HR is there to protect “the business,” not employees. Took me ten years to figure that out.

The total hours you have to work isn’t on the job ad

The scary thing about getting a new job is not knowing how many hours you have to work. I remember this guy at work (let’s call him Jack). Jack joined all excited for his new job. The sales pitch from HR was Oscar winning.

After the two weeks of training, our company worked him to the bone. He had to be on call every day of the week. Reports had to be done on Sundays. There were never enough hours in the day to complete all the tasks given by the leadership team.

The job description he signed up for had his duties. They never mentioned anything about the fact those duties could be called upon by a large number of people at any time.

As a result, Jack worked himself to the bone for the same salary as people who did similar duties in a 40-hour week. When you take a job nobody lays out how many hours are required.

A job that pays $60,000 and can be done in a 40-hour week is a way better opportunity than a job that pays $65,000 but has endless requests that cause you to work weekends to catch up.

Find out how many hours you really have to work. Be bold about it. Otherwise, you’ll be working 7 days to do a job others get the luxury of doing in 5 days.

People quit bad bosses, not companies

A company is a fictitious entity registered by filing a piece of paper. You don’t quit a piece of paper for a new job. Nope.

People quit bad bosses, not companies. I left a boss who ignored me and couldn’t be quiet about how great it was to live on a golf course. All I could think about was golf balls hitting his windows, and the golf pants parade up and down his street every day. Then there was the way he tormented my team.

He’d create Hunger Game challenges. There’d be a winner and a loser. He couldn’t wait to see the loser put up for public execution and to watch the crowd throw fruit at the victim’s face.

The loser of one of his games created a chance for him to laugh his evil laugh, and get an erotic form of pleasure he clearly did get at home. I eventually quit that boss. On my way out a HR lady spoke to me.

“What did the company do wrong?”

She didn’t get it. A company doesn’t have feelings. It’s the people that work within a company that carries a vision forward. Those people need to be led. And no amount of excuses for assholery will do.

The challenge is we often quit bad bosses and don’t realize that’s what we’re doing. It’s not necessarily evil behavior, like I experienced, that’s the problem. A lack of attention from a boss is the most common problem I’ve seen. A boss that never allows you to step up. A boss that locks you in your work from home office like a prison and forgets about your life goals and dreams.

After a while you stop growing. You remain stagnant. You’re dying to get in motion again and be challenged. Meanwhile, boss man is scoffing down doughnuts at morning work events and completely forgetting you exist.

Nobody likes to be ignored at work, especially by our boss. We want our boss to enable us to outgrow in our career and perhaps become a leader one day. Bosses can kill career dreams, not just by acting like a fool, but by doing nothing, too.

Quit a boss that feels invisible. There are lots of good ones out there.

Take all of your holidays

I spent five years of my career never taking a single day of holidays. I bragged to other employees how good it was. I wore that zero holidays stat as a badge of honor. Eventually, I completely burned out.

One year the board of directors found out. They called me into the boardroom and insisted I take holidays immediately. I took their advice. I booked holidays for that January. On 9 am of the first day of my holidays, there was a blow up at work. The board rang me and asked me to abandon my holidays and come to work immediately.

“There’s been an incident.”

I got tired of working on the Titanic. Not long after, I left behind a business I loved to escape the insane nightmare of endless sieges.

Holidays are where your mind resets. What you learn at work makes sense when you take time off to do nothing. Then when you come back to work, the ideas that get you ahead in your career come to you with a lot less effort.

The salary is forgotten after the first paycheck

Taking a job with more money feels amazing. You think you’ve won the lottery. When it happened to me it felt good … for about a fortnight. After that, the extra zero on my bank balance became meaningless — the same way points you earn playing a Nintendo game feel lifeless. They’re just numbers.

A side hustle can make you more money than an annual bonus

Corporations try and lure their victims into the dungeon of broken dreams by dangling bonuses in front of us.

A bonus is an illusion. Read that again.

Whatever you’re told about bonuses can be completely changed. Your employer can decide a global health crisis means nobody is getting one. Or the profits can be down, so bonuses are reduced or forfeited. Or a crappy boss can decide to give your bonus to someone else they like better. According to CNBC, 1 in 3 workers in the US faced a pay cut in 2020 due to lockdowns. 

I quit working for bonuses years ago. All I want is as much time off as possible to work on my after hours side hustle. A side hustle is an experiment that can eventually make you more money than any silly little bonus can.

A side hustle can turn into freelancing. A side hustle can cause you not to need a traditional job. A side hustle can even become a business that turns into a tiny empire you didn’t know you had the power to create.

Ask if your bonus can be traded for more time.

Be wary of flashy culture presentations created by HR politicians

If a company has to talk about its culture then the slide deck is lying.

Good company cultures I’ve worked in don’t have a marketing department churning out content full of stock images with dudes in suits shaking hands and pretending to look happy while missing their kid’s baseball game.

Good company culture comes from good people.

A no asshole policy is how the best startups I’ve seen produce high-performing cultures. Letting a new person into their company is a big decision. They require different parts of the business to be part of the process. Senior leader approval isn’t enough.

“Jobs for the boys” is outlawed.

They do rigorous reference checks on the individual to find out if there are any skeletons in the closet, to ensure there aren’t any incidents where they randomly blow up like a 5-year-old at grown-ups. They’d rather hire nobody than a culture killer.

Look for humility and honesty and you’ll find kickass company culture.

A percentage of your salary can buy back time

As you climb through the ranks of your career, there are hidden opportunities to negotiate a better way of life thanks to the value you provide.

When I got my chance, I didn’t ask for more money. In fact, I didn’t put them through a used car salesman back and forth like I normally would. I did this.

“Could I trade 20% of your salary offer for one day off per week?”

The company said yes. I got to work four days instead of five. That extra day per week allowed me to work on my writing. I also built an online business. That one decision became the stepping stone to leave the corporate world behind and do my own thing full-time.

A colleague of mine negotiated differently. He’s a farmer who loves to travel around Europe. When he changed jobs he asked for eight weeks of holidays per year instead of four … and got it.

Buy back your time. Time is a better currency than money.

Beware of the Bitcoin monsters

This one is obscure. Sorry. Be careful talking about Bitcoin at work.

When I joined a new company and confessed my love for the Bitcoin god, one colleague tore me to pieces. He shared my Bitcoin secret with senior leaders and made me look like a crazy person.

He told them how I worshiped the high priest of Bitcoin, Michael Saylor, and went to Sunday crypto church, and drank holy Ethereum water while bowing down in front of the almighty bible that contains the sins of inflation.

Before I left that job, I reminded him of what he did. We both sat down and analyzed the Bitcoin price together. It went up over 100% since he called me a Bitcoin terrorist. He smiled and confessed he too had joined the secret society.

Bitcoin is a religion. Not everybody will respect your religion.


A workplace is a Hollywood movie production full of actors. Learning to see the illusions from the reality is key. Once you can see work for what it is, you can make the most of it.

Work is where we go to find our place in the world and meet friends for life. All that’s left after you hop from one job to another are the awesome people you collect. The rest is marketing.

Tim Denning
I am an Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship. You may have seen my work on Medium, LinkedIn, Bitclout, or Twitter.

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