The Hardest Parts of Changing Careers That No One Talks About

Everywhere you look online, you’ll find gurus, books, and courses promising to take you from the land of misery—where you hate your job—to the promised land, where you wake up every morning excited to do work you love. That’s a noble goal. I believe it’s absolutely worth pursuing.

But what gets overlooked in all that motivational hype are the real challenges you’re going to face along the way.

I’ve been navigating this process myself, shifting from the chemical production and transportation industry to IT and network engineering. And I want to share some of the hardest parts of career transition that rarely get talked about. Because if you’re in the middle of this journey—or thinking about making the leap—knowing what’s ahead can prepare you for the fight.

Let’s get into it.

1. Your Family Responsibilities Dictate Your Options

I started this process in my early 30s. I went back to school around 30 or 31, and now, at 34, I’ve been grinding at this for years. But unlike a fresh college grad, I have real responsibilities—bills to pay, a wife and kids to take care of, and a standard of living I can’t just ignore.

Here’s what that means:

When you transition to a new field, especially a completely different industry, you often have to take a pay cut to get your foot in the door.
The size of that pay cut depends on your circumstances—how much flexibility do you have? Can you afford to make less while you gain experience?
I don’t chase money. I’m doing this because I want to solve interesting problems and do meaningful work. But that doesn’t mean I can work for peanuts. I still have a baseline income I need to maintain.

That’s why entry-level IT jobs were never really an option for me. I tried it once—took a job as a NOC Technician(Network Operations Center Tech), making far less than I needed, thinking I could make up the gap with side gigs.

It didn’t work.

I was driving Uber, doing DoorDash, taking IT gigs on platforms like Field Nation and WorkMarket, but I barely had time to breathe. I couldn’t spend quality time with my family. And worse? I didn’t have the time to learn and develop my skills like I needed to.

That experience made one thing clear: I couldn’t take an entry-level job just to “get my foot in the door.” Instead, I had to be laser-focused on building real, demonstrable skills so I could go straight into a network admin or engineering role.

If you’re in a similar boat—if you have a family, responsibilities, and real financial needs—you have to be more strategic. You need to create your own opportunities, not just wait for someone to give you one.

2. The Competition is Brutal

When you start this journey, it’s easy to think that as long as you work hard, you’ll find an opportunity.

But here’s the truth:

You’re competing with a sea of candidates—young, fresh college grads with degrees, people with years of experience, and others just like you trying to make a transition.

I didn’t take college seriously the first time around. I flunked out of a small community college when I was younger because I wasn’t intentional about my future. By the time I did get serious, I was already behind.

Now, as I compete for mid-level IT jobs, I’m going up against:

College grads with degrees and internships
People with several years of IT experience
IT career changers who might have fewer responsibilities than I do, meaning they can take lower-paying jobs and build experience faster

That means I have to work twice as hard to stand out.

This is why Bits of Progress is so important to me. This isn’t just a content brand—it’s my proof of work. It forces me to:

Learn deeply and actually master the skills I need
Document what I’m doing to show my work to potential employers
Differentiate myself from every other job seeker out there

Someone with a degree and a couple of years of IT experience might be moderately valuable. But for me to compete, I need to be extraordinarily valuable.

That’s the mindset shift you need to have. If you’re up against people with more credentials, you have to bring something else to the table.

3. The Timeline is Always Longer Than You Think

Gurus love to tell you about their fastest success stories.

“John landed his dream IT job in six months!”
“Sarah transitioned to cybersecurity in three months!”

They sell you the success story, but they don’t tell you about the blood, sweat, and frustration. They fail to mention the months and years of sacrificed evenings and weekends.

Here’s what no one tells you:

However long you think this is going to take, you might as well double or triple it.

When I started, I thought I’d land a mid-level IT job within a year or two. That was way off.

I underestimated how much time I’d need to learn real, applicable skills
I overestimated how much entry-level IT jobs actually paid in my area
I didn’t realize just how much competition there was for every single role

This journey is longer, harder, and more frustrating than most people expect. But if you stick with it, you will break through.

Why It’s Still Worth It

Despite all of this, I’m still excited about where I’m headed.

Why?

Because this transition isn’t just about getting a better job. It’s about becoming the kind of person who can handle the challenges that come with that job.

If you’re just chasing money, this is going to be miserable. But if you’re chasing work that truly energizes you, the grind is worth it.

Here’s why passion matters:

It gives you a competitive advantage. If you love the work, you’ll spend extra hours learning, practicing, and honing your skills—while others are watching Netflix.
It makes the long journey easier. You’ll push through the frustration, rejection, and obstacles because you actually care about the craft.
It makes you more valuable. Companies need problem solvers, not just people looking for a paycheck. When you love what you do, you naturally become more skilled and sought after.

I don’t go home and waste time. I go home and:

Build networks.
Lab new configurations.
Study cybersecurity principles.
Sharpen my problem-solving skills.

Not because I have to. Because I want to.

And that’s why I’m confident that, in the long run, I’ll win.

Final Thoughts

If you’re thinking about changing careers, here’s what I want you to take away from this:

Be realistic about your financial situation. If you have a family, you can’t afford to take just any job—plan accordingly.
Understand the competition. You need to differentiate yourself if you want to stand out.
Expect it to take longer than you think. If you assume it’ll be a quick transition, you’ll get discouraged too soon.

This journey isn’t easy. But it’s worth it.

Because at the end of the day, the real reward isn’t just a better job. It’s becoming the person capable of earning that job.

So the question is—are you willing to go through the process?

The Hardest Part of Changing Careers That No One Talks About