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The Biggest Regrets of a 9-5 Employee
The Biggest Regrets of a 9-5 Employee


The Biggest Regrets of a 9-5 Employee

You will learn a lot from them and be incredibly inspired.

I am a 9-5 worker. I am a writer too. And I have been in and out of entrepreneurship like rehab.

It’s hard to admit, but I have regrets, although they aren’t going to hold me back anymore. I want to share these regrets in the context of 9-5 work because many people can identify with them. See, your problems are not so different.

When you think to yourself, “I felt like that once too,” after reading about another person’s regrets, everything changes.

Didn’t try a side hustle

I sacrificed my outside work passions for years. I let work dominate me when my hobbies gave me the most joy.

You have probably experienced this too. Where you love something after-hours and hold yourself back from making it a reality. Maybe it’s fear. Maybe it’s your family. Or maybe you’re afraid of your employer. You might just be overworked and not have the time left in your calendar to take action.

Ignoring your side hustles can only get you so far. Your side hustles have the potential to become your main gig. Knowing if that’s possible for you is something you must explore and experiment with.

Didn’t tell my boss “enough!”

I once worked for a bad boss. I saw them treat my direct reports unfairly. I watched them brag about how they were going to get all the other leaders (their competitors) fired. I enabled their bad behavior. I ignored the harsh treatment they dished out to my team. I let them turn work into a game of musical chairs, where the last person standing faced the death penalty followed by public ridicule.

I regret not saying to this selfish son of a gun “enough, mate!” Even when he fired me I regret not telling him the truth. I didn’t want to give him a piece of my mind.

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I wanted to tell him so he could learn the lesson and change.

If you witness toxic, selfish behavior then you can stand up and say “enough.” Only when bad behavior is pointed out can the potential for growth occur. Many people live in a vacuum. They can’t see themselves as others see them.

Didn’t help the person who got fired

I have watched many people in my working life be fired. I regret not reaching out to many of them to let them know I cared, and their contribution mattered. In recent years I have made it a habit to treat people who get fired with the same respect I received when it happened to me last year.

The person who gets fired could be you one day. The person who gets fired can go on to bigger and better things, and take you with them. Never underestimate an underdog who loses their job and experiences a transformation, followed by an epic comeback.

Nobody who gets fired is broken. They’re human.

Didn’t become a content creator

I spent most of my career afraid to publish anything on the internet. “What if my boss sees,” I’d think to myself. 9-5 employees are afraid to publish on platforms like LinkedIn because they’re afraid of what people might think.

People will form a positive or negative opinion about you regardless of whether you publish content online. So you may as well hit the publish button and let what will be, be.

No corporate entity can buy your voice. No boss is worth silencing your right to freedom of speech.

Here’s the crazy thing: when you create content your day job gets better. Most of the success I’ve had in my career is because of things I published on the internet. Last year I was walking to an important meeting. I bumped into the leader’s personal assistant.

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Before I could open my mouth he said “Loved what you wrote on LinkedIn yesterday. Thanks for the inspiration.” That personal assistant ended up helping me get meetings with incredibly hard to reach people. The first time he met we instantly clicked. It was content that did it — not me.

You hear the term thought leaders all the time in your career.
A thought leader is just a content creator.

Thought leaders get paid more money and get access to better career opportunities.

So why can’t you do it? You can. A thought leader publishes thoughts online, otherwise known as content. You’ve been lied to. It’s okay to be a thought leader. Pro tip: positivity rarely gets tired and it’s nearly impossible to get corporate punishment for it.

I regret not becoming a content creator sooner. Don’t make the same mistake.

Didn’t have control

Having one income stream made me feel like a prisoner.

When you bet everything on black and allow deposits into your bank account from only one entity, you’re dependent. They can cut off your livelihood at any moment. I wish I gained control of my work life sooner and had the guts to charge people money in return for my skills.

I also lacked control earlier in my career because I had no savings or financial assets behind me. All it would take was a $2000 hospital bill to bankrupt me. Once I made sense of how money works, I found ways to help money grow on its own without me having to always top up my personal money supply.

Control in your career gives you freedom to do whatever the heck you want. A 6-month sabbatical is a powerful idea that can change your life.

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Didn’t get a work wife

A work wife is a best friend you spend time with every day at work. I was a recluse for the early part of my career. I locked the office door of my startup and told people not to disturb me.

Later, while working in a bank, I found two work wives. We went everywhere together. We made coffee appointments with customers so we could “chew the fat.” Our customers became our children. We loved them to death. We wore their company t-shirts as if they were our own. We took them out to lunch like we were having lunch with our dying mother for the final time.

It wasn’t customer satisfaction. It was bulletproof relationships built on trust, where both sides did well out of the business transaction. Oversimplification: it was hanging out with friends and helping each other.

Didn’t experiment enough with entrepreneurship

Entrepreneurship became my unsafe word.

After seven startup failures I gave it away. To be an entrepreneur made me feel sick. I stayed in a 9-5 job to hide from my entrepreneur phobia. I regret this immensely. Entrepreneurship is in my blood and always will be. One business failure or two doesn’t make you a failure. Your belief about what entrepreneurship really is makes all the difference.

Don’t worship entrepreneurship.

Entrepreneurship is overrated. It’s just having the guts to charge money for helping a person out who asked you for it. The help starts out as free assistance (MVP). Then the help turns into tiers: free, low price, higher price, and back to free again for the underdogs.

If you never try entrepreneurship then you’ll wonder for the rest of your life what it’s like. Try charging money for something outside of your 9-5 job. You may discover you like working for yourself better than you like working for a company. You never know if you don’t try. Try, try, try, fail…repeat. Win.

Didn’t ask for a day off

I regret not asking for one day off a week to write, sooner. I waited years. The first time I asked my hands were shaking. I thought it would cost me a dream job leading a team of sixteen account managers. It didn’t. The HR person said yes. Then at my next job I politely asked again and they said yes.

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Working 4 days a week means you take home 20% less pay. But what you learn on that one day off a week from your 9-5 job will pay your bills for the rest of your life. You’ll learn independence, the power of sacrifice, having the guts to do your own thing, risk mitigation, and diversification.

Or you can do what my friend Chris did and spend the extra day off a week to watch your children grow up and help out at their school.

A 4-day a week job can change how you think and how you act. That’s worth giving up 20% of your salary for.

Didn’t understand the point of a job

I regret not understanding the point of a 9-5 job sooner.

I went to work and chased titles and money for most of my career. I thought a BMW was the meaning of life. I wore stupid-looking suits trying to be somebody I wasn’t, to impress people who wouldn’t attend my funeral if my life ended. The point of a 9-5 job are these things:

  • Meet people you like working with
  • Discover your talents
  • Build skills
  • Meet people who could one day become your own customers
  • Attend events
  • Experiment with someone else’s money
  • Test your ideas with your employer’s business
  • Discover ideas you wouldn’t find piss-farting around at home by yourself trying to figure out how to make money
  • See the suffering in your colleagues as your own

The point of working is to give your life meaning. The point of work is to make enough money to retire as quick as possible so you can quit whatever it is you do, take a short break, and then go back to work while never having to bother caring about how much you get paid ever again.

By not needing to care how much you get paid, you make three times the amount of money — it’s counter-intuitive.

It’s never too late to take your regrets and act on them. That’s what I have done and now my regrets are my driving force.

Why couldn’t you take what you regret about your work and turn it into a superpower?

Source : Medium

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