Should You Change Careers? 4 Common Fears and How to Work Through Them

🌱 Career Transition? Read This First.

Hi there! I’m Jill—your digital friend—and today, I want to talk about breaking through the mental barriers that can show up when you are changing career paths.

If you're in your 30s, like me, there's a good chance you'll be working for another 40 years before retirement—and still have 30 more years to enjoy life after that. With people living longer, working longer, and redefining what success looks like, career change is becoming more than a bold move—it’s a life skill.

I’ve personally navigated four different job functions in the past seven years since graduating from university. In this post, I’ll share why career transitions matters, what often holds people back, and how to move forward with more clarity and confidence. In the end, we’ll return to a topic close to my heart: how to maintain inner peace through uncertain times.

💡 Why Think About a Career Transition?

With advancements in healthcare, global life expectancy is projected to increase from 73.6 years in 2022 to 78.1 by 2050.

Even within my own family, this trend is clear—my grandfather passed away at 92, and my husband’s grandmother lived to be 104.

There’s a strong possibility that many of us will live to be 100. If you're in your 30s, that means you may have decades of both work and life ahead. It’s a good time to ask: Is the career I’m in today still the right one for me tomorrow?

Now that we’ve put things into perspective, career transitions don’t just seem reasonable—they’re becoming essential life skills. To stay relevant and competitive over the coming decades, many of us will either need to switch roles or keep expanding our skill sets.

🧠 What’s Holding You Back?

Here are four common reasons people hesitate to make a career transition—and what to do about them:

1. Self-Doubt

“I’m not sure I can do it. I don’t know how long it will take to master new skills.”

Self-doubt can be paralyzing. The key is to build confidence gradually. Try this:

• Start small—so small that you can’t fail: If you’re a Data Scientist considering a move into Product Management, start by reading the product pages on your company’s website. Take note of key features and try to understand how the product is positioned and communicated.

• Gather information: If you’re a UX Designer thinking about becoming a Software Engineer, try looking up a simple SQL tutorial online. Dip your toes into the coding world and see if it sparks interest.

• Learn from others: There are countless YouTubers and bloggers sharing their career journeys—what their day-to-day looks like, how they transitioned, what challenges they faced. Even though every path is unique, you might find patterns, inspiration, or reassurance in their stories.

The more you learn, the more confident you’ll feel in your decision—whether you move forward or not.

2. Attachment to Current Level or Momentum

“I’ve been doing this job for years. I might get promoted soon. If I switch now, I’ll have to start over.”

Starting over often means slowing your momentum, as it takes time to build expertise in a new space. But ask yourself:

• Is your current role aligned with your 10-year vision?

• Does it bring you genuine satisfaction?

• If not, how meaningful will that next promotion really be?

• Will transitioning later be harder once you're more specialized?

• Does the new opportunity align more deeply with your values?

The key is to stay true to yourself—and to be brutally honest about your career aspirations.

3. Lack of Motivation

“I’m comfortable where I am. Even though I know I have more to offer, I don’t feel motivated enough to leave my comfort zone.”

That’s okay. There’s no need to force movement. If your motivation isn’t strong or clear yet, it may not be the right time—and that’s totally valid.

Come back to the reflection questions from the previous section when you’re ready. You’re not behind. You’re right on time.

4. Risk Aversion

“The new role sounds exciting, but I’m not sure how stable it is. I have responsibilities. I need security.”

This is the most real risk—and it's valid. Financial stability is a top priority for many, including me.

But remember: career transitions can be gradual. Explore while you’re still in your current role. Test the waters through side projects or learning on the side. With planning, you can honor your need for security and create space for change.

🧭 Find Your “Why” before “How”

At the heart of every successful transition is one key question:

Why do you want to switch jobs?

• Is it for better pay? A healthier work environment?

• Is it something more—something that genuinely interests you, that lets you do what you're good at?

• Maybe it’s even a deeper calling—one that aligns with your core values and makes you want to dedicate the next 5 to 10 years pursuing it.

Take your time with this, every story is different. There’s no right or wrong path—just the one that’s right for you.

🧘 Inner Peace

There is nothing to fear but fear itself.

The key to staying grounded in this process is having a firm belief in who you are—and continuing to move forward, even if just inch by inch, as you gather more information.

Most transitions happen while people are still in their current roles. The process might take 6–18 months or even longer. As long as your financial stability is intact (or even if it's not, depending on your risk tolerance), you're free to explore.

And remember: you miss 100% of the shots you don’t take.

Cheers.

📬 Final Thoughts

You don’t have to figure everything out today. But asking better questions now can lead to more intentional decisions later. I hope this post helps you move forward with clarity, and a little more peace.