Ten Uncomfortable Life Lessons I Learned from the Corporate World

Tim Denning

Doers get paid more.


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A corporation is a human experiment.

Watching how people interact in a big company can teach you so much about life — both good and bad.

I’ve worked in corporate for a good chunk of my life. It’s taught me a lot. I have seen people rise to unbelievable heights. I’ve also seen people bring others down, and lose everything, over and over again.

Who you are outside of corporate life will determine what good you can do for a big company. You can have all the innovative thinking, business degrees, and network of power connections you like. It all means nothing if you don’t pay attention to who you show up as at work.

How do I know?

I was a red power-tie wearing knob in a black pinstripe suit, driving a BMW, lost in a world of selfishness and logo-dropping chess porn.

Not anymore. I use corporate. It no longer uses me.

These points will take you right back to the corporate office. Guaranteed or your money back. Pinky promise, double-dare you.

1. Polite assertiveness is a superpower.

I am no badass.

But corporate life has taught me not to take crap from anybody. Last week I cold-called a prospect from a company I already deal with. “Hi, I’m from XYZ company…” Beep. Beep. Beep. This happened several times. So I sent a polite assertive text message.

“Hey, no need to be rude. You never know who the person is on the other side of the phone.”

They messaged back and apologized. Now we’re going to catch up for lunch. There is a good chance of business occurring going forward.

Your needs in life are not an inconvenience. You don’t need to apologize for asking for a few minutes of someone’s time. The opposite is true. Stick up for yourself. Nobody has the right to be rude to you. Call them out nicely. Magic fairy dust stuff will happen when you do.

2. Your ego will build your career or destroy it.

Senior leaders can quickly lose the plot with a promotion. What goes wrong? Their ego gets a spit-shine. They forget their leadership role is a privilege not a certainty for the rest of their career.

Your ego can tell you to be mean.
Your ego says “I’m better than you.”
Your ego can make you think you deserve privileges.

But leadership is a rental property. You pay the price through your commitment to the people you lead. And if you stop paying the price, you end up out on your ass with an eviction notice and no job to shelter you.

Measure your ego regularly.

Compare your ego to previous years. Do you think you’re too good? Has your confidence got the better of you? Are you talking down to people? Are you unnecessarily impatient? Big question…

Are you being a good human? Only you can answer that.

Confession: my corporate career has fallen apart a few times. Each time my ego got the better of me and started telling me I had a spidey sense for success. Really, I’d become delusional and stank of selfishness.

3. One-way thinking is created by a lack of diversity, gender, sexual orientation, and race.

There’s a lot of one-way thinking applied to corporate problems.

Applying one segment of society’s thinking to a problem is a terrible idea. You’re going to get blind spots all over the Powerpoint solution. Instead, the uncomfortable truth is when an organization is lacking diversity, it messes all over itself trying to chase revenue in places it can’t be found.

Revenue is found in a diverse workforce of people who represent customers (humans) from all walks of life and backgrounds.

Bonus: some corporate marketing doesn’t make sense. It’s because of a lack of diversity. I see ads for luxury designer brands and often can’t put my finger on why I don’t care about what they’re selling. Then I think to myself, “Ahh it just feels too…umm…white.” Imagine what a splash of color/diversity could do to a lot of corporate marketing.

4. Drop the buzz words.

I read a CEO letter to shareholders from a corporation recently. It read like something Captain Planet wrote. Every second word was a buzz word. “Innovation, exponential growth, market position….wank, wank, wank.”

Drop the cliches too. “All about the people.” Really Captain Planet? Why so many covid layoffs then?

Nobody believes corporate words anymore. It’s all about action.

5. Replace business improvement with people improvement.

Business improvement is a huge industry. Some corporations have kaizaned or agiled the heck out of their company for years and still become Kodak.

Business improves when people do. People improvement in business should be the next booming industry. Help leaders see their weaknesses. Take away their bonuses when their emotional intelligence plummets.

‘Become a better person’ is the best advice I’ve ever been given. When you improve, everything you touch, including the business, improves.

6. Customers buy from people, not businesses.

A business speaks a different language. Marketing campaigns don’t speak as loud as the people whose voices talk to the customer. A voice can sound humble, kind, helpful, imaginative, and curious. It can be harsh, impatient, unhelpful and sound disinterested too.

Improve the people to improve the business.

7. Getting things done affects the size of your paycheck.

Doers get paid more.

Become a doer, not a talker. Talkers have meetings, over-plan, speak too much, fall in love with Powerpoint, shuffle paper, overthink, commit, but rarely do.

The doers get to work. They take the first step. They try something. They lean into the natural fear business brings out in each of us. Doing is taking small risks in disguise.

As my first boss said: “Take action first and apologize for your mistakes later.”

Execution is a superpower. If you learn execution, you can take the skill from the corporate world to the startup world and make a fortune, while making a difference. Try taking action for breakfast.

8. Smartasses eventually end up unemployed.

It happened to me. I was a smart ass. My corporate ass got lifted from one seat to another. If every business conversation you have becomes sarcastic, your corporate comfort cushion is going to explode. There’ll be duck feathers everywhere. You’ll be saying a word that rhymes with duck a lot too.

People are doing the best they can at work. They don’t need you turning their work into a never-ending joke. Cut people some slack.

Most corporations are more dysfunctional than the tv show Faulty Towers. It makes work interesting.

9. Dating someone at work can end badly.

Don’t do it if you can avoid it. I did it twice.

My friend said to me, “Don’t shit where you eat.” I ignored her wise words. When the romance turned into flames, everybody was talking. My career progression was defined by that bad romance.

Having your sex life on display to your work colleagues is probably a bad idea. Unless you’re an exhibitionist — which I’m not.

10. Jobs for the boys.

Some corporations are boys’ clubs. It sucks.

Career opportunities are given to “the boys,” not the hardworking people who have earned them. The interview process is tampered with or never happens. A fake job ad goes up to pretend it’s an open opportunity.

Unemployed people who have been out of work for longer than they would like, and are feeling the pressure, are invited to the corporate headquarters to waste their time interviewing for a job that doesn’t exist.

It would be awesome if software could put an end to jobs for the boys. Maybe making the corporate hiring process more spread out, with AI checking for bullshit, could be a way to end the boys’ club. Until then, say no to jobs for the boys bro culture.

At the end of your corporate career, you will forget job titles, promotions, business deals, revenue, office politics, bonuses, and products/services.

All you will remember are the people you enjoyed working with, who you became in your corporate life, and the difference you made. Don’t wait to the end of your career to realize the power of work.

What do you want to leave behind when you exit earth through the grim reapers’ trap door? Surely not meaningless corporate mediocrity games.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com


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