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Your Boss Doesn’t Care About Your Career, Personal Development, or Income

by | Jul 31, 2023 | Startups

He didn’t care about me.

I was destined to be fired. I applied for jobs as fast as I could. I had rent to pay. But I was too late. The bugger beat me to it. He fired my fine ass in 2019.

You’ve got to see the signs of a boss that doesn’t care — or the same can happen to you. This article isn’t a guidebook to quit your job and live a laptop lifestyle. Soz, to the people that wanted that. The 4-Hour Workweek is a better option for ya’ll.

What you’re about to read is for the people who like having a career and want to get the most out of their jobs. I was that guy. A bank jock.

Here’s how to get career growth faster than most.

Not gonna lie … most bosses don’t care (by design)

The mistake I’ve seen people make in their careers, that’s the same one that’s been going on for eternity is this: thinking your boss cares.

There are some rare ones who do care.

But most don’t. Not because they’re the devil in a suit, but because the modern corporation doesn’t allow a boss to be your best friend.

Spend a day in their shoes and you’ll see. Being a boss is mostly a pain in the ass. You’re responsible for everything. Under-resourced. And your calendar is jammed up with a sh*t sandwich of back-to-back meetings.

The last thing your boss wants is to get out of a meeting and into another one with you. If they don’t hit their KPIs and manage the team to deliver revenue-generating value, then they will lost their title.

Everything they’ve worked for will go up in smoke. Poof.

Get in your boss’s shoes before you try to think about how they can help with your career growth.

Advancing your career is a threat to your employer

Think about it.

You get the awesome job title. Now your employer has to backfill that pain in the butt job you used to do on the frontline that not many people want to do. And don’t get me started on side hustles.

A friend of mine committed the cardinal sin and asked his boss for approval of his side hustle. What came next wiped the smirk off his pretty boy face.

“You can’t do that. It’s against company policy. Focus on your work. We can give you extra hours if need be.”

His online dream died. Oh…and he mentioned he was going to post on social media. His boss hated that idea too.

“You need permission to write on LinkedIn. Stop! Let me speak to HR.”

There’s no incentive for your boss or employer to see you become an online superstar. Or for you to build a passive income machine that allows you to retire from the workforce.

Side hustles are even worse. Your boss thinks you’ll do it on company time. They’d rather you work back late and serve them instead of you going home at 5 PM and letting you become the next Mr Beast Youtuber.

Give your boss a “do they give a fudge” test

Like I said, some bosses do care. But they’re rare.

Do a test to see if you have one of these career unicorns. Invite your boss to a career development meeting. Pay attention to see if they do any preparation. See if they bring ideas to the table.

Are they passionate about the conversation once it gets started? Or do they just sit there and let you do all the talking?

The big reveal happens when you assign next steps. Do they take those steps? Do they want to make this conversation recurring?

Here are a few more signs:

  • Do they use their network to help grow your career?
  • Do they get secondments for you or trials in other departments?

If none of these signs are good then you have an anti-career boss. They’re the norm. These are the bosses you shut up around. Don’t let them know your plans. Shhhh about side hustles or making money online.

Don’t ask them for favors. Just stay around until you find the next opportunity then part ways. They’ll be pissed but you’ll get ahead.

Increasing your income is the last thing in the world they want to do

Asking nicely for a pay rise or bonus is like asking Marilyn Manson to be on his best behavior.

It’s easier to keep paying you the same money. A higher salary for you costs your boss and employer more. Sure, you could quit — but most bosses know you won’t do that because people are afraid of change.

We prefer comfort and certainty.

Don’t get me started on bonuses. Paying you above your salary has little benefit to them. They might do it as a token gesture or a once-off.

But you can’t rely on employee incentives because they change more than my daughter’s diaper does in a day. No bonus is a guarantee. It’s a dream they sell you so you’ll stay and believe the lie that you’re an owner in the business.

Don’t get fooled by the be-your-own-boss fallacy.

Unless you own 100% of the shares in the business, you’re an employee. Act like it.

Take control of your own goddamn career (like this)

Great, you’re sold.

This reality isn’t supposed to get you down. It’s meant to get you to take action, and in the right way. Time to steer your own career.

Practice daily self-education

Your skills determine your income and career growth.

A person of value will naturally advance in their career without too much hassle. Therefore, have an unlimited budget for plain online education. Use it to learn uncommon skills like copywriting, persuasion, AI, entrepreneurship, etc.

Interview for jobs all the time (even when you don’t need one)

The key to better jobs is to master job interviews.

If you can’t win this game, you’ll never make it past round one of the career game and get hired anywhere else.

Practice makes perfect. I interviewed at investment banks for a year with no intention of getting hired. By the end I could ace interviews. An interview a week is a good KPI for yourself.

If you get hired by accident, just say no and pretend you’re in high demand and got another opportunity.

Network outside your employer

Jobs come from people, not job ads.

Stop applying for jobs and getting racially profiled by an AI. Make jobs come to you. Network in the LinkedIn DMs. Don’t ask for stuff. Don’t suggest coffee. Just start interesting conversations.


Do 5 minutes of research before you send a DM. Find an unusual angle to kick off a conversation. If it goes well in text then make it a Zoom call. If it goes really well then turn it into coffee or lunch. If it goes bad or you get ghosted, move on.

Random conversations lead to jobs that increase incomes.

Write up your career plan and show no one

Have a rough back-of the envelope idea where you want to go. Just nail what job titles and industries interest you. Think about the ideal work day. Better yet, write down your ideal work day.

Get some paid mentors

Free mentors are good. But paid coaches, advisors, and mentors are better.

Hire one if you’re serious. Find someone who’s already successful in the area you want to work in. Then get them to help write up the plan and pay them well for it.

Post on social media and shut up about it

Social makes you a magnet for opportunities, too.

Share your ideas. Post daily. Be a thought leader in your field. Start public conversations. Share trends. Then watch your DMs light up.

One of those messages will change your career forever. But you won’t know which one — that’s the best part.

Work on a new lifestyle after hours

A career is 10x easier when you don’t need the money.

Make your financial life easier by having a side hustle that earns you a second income. Use it as an insurance policy against job loss. While you’re at it, learn basic finance too. Invest in assets and generate passive income.

Not enough to buy Lambos because that takes risk. But enough to live comfortably with less stress (the ultimate success).

Final Thought

There are just a few ideas to kickstart your career growth. If you sit still and don’t take your career seriously it won’t grow. And if you rely on a boss to do the work for you like a babysitter then progress won’t happen.

Remember: An employer needs you to stay in the same position for as long as possible so they can profit off your time.

Practice proactive career design.

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