Questions That Keep Us Skeptical About Career Change

January 23, 2026

“I finally feel free, because I know I don’t need my job anymore. Now I know exactly what I do need. And it’s way less than I thought.”

I often hear some version of this from clients after we go through their numbers together. Before that conversation, they feel stuck. They know they want something different, but they stay put.

What holds them back? Probably the same things that hold you back.

Everything you’ve learned tells you to stay put. Since the Industrial Revolution, our society has been taught the same script. Go to school. Pick a career. Retire one day.

So it’s understandable that you are skeptical. Every thought of a better life is countered by doubts about whether it's even possible.

Four questions come up more than any others.

What if I'll actually miss the parts of my job that I like?

If you’re asking this, you’re in a strong position. The best way to make a career transition is calmy and patiently. And since you still get enjoyment from your job, there’s no rush for you.

But let me ask you a question: just because your current situation is good enough, does that mean you shouldn’t allow yourself to start planning for something even better?

After my own battle with cancer, I internalized the fact that we never know when our time will be up. And I learned that regret is much scarier than failure.

When you reach the end of your road, do you want to be thinking about all the things you wished you would’ve tried? Or do you want to be thinking about all the things you experienced?

The relationships you made more time for. The times you learned something new and grew. The passions you pursued.

Planning for these things doesn't commit you to anything. But it does open doors you didn't know existed.

What if some intentional financial planning showed you that you could walk away whenever you wanted? That knowledge alone might change how you show up at work. More confidence. Clearer boundaries. Better leverage.

Knowing you don’t need your paycheck, maybe you could finally work on your terms. How might your mood improve if you no longer felt pressured to say “yes” to aspects of your job that drain your energy? How might that improve your performance?

Or maybe the feeling of freedom and detachment would serve as light at the end of the tunnel. Which could allow you to strategically plan a transition at some point in the future, with an even bigger financial cushion. And a clear plan for what’s next.

You don't have to leave. You just have to know that you could. And if you're not there yet, you can start building toward it.

What if I can never go back?

This one held me back for a long time.

I spent more than a decade in a career where, too often, my work culture clashed with my values. And as a flat fee financial advisor, I’ve created a wealth management business that doesn’t clash with my values.

Establishing and growing my business meant I needed to clearly articulate this publicly.

Posting about this on social media, while former bosses and colleagues watched from the sidelines, was scary. I figured I was burning bridges.

But speaking in my authentic voice attracted people who actually shared my values. And those connections became more valuable than any door I thought I was closing. I’ve even turned down job opportunities I never had to apply for.

The same thing happens for most people who make this kind of move.

You may not be thinking about starting a business and posting on social media, but if you move toward something that’s truly important, you’ll find new connections that are just as valuable for you. When you build relationships around shared values, opportunities follow.

And remember, you don't have to leap right away. Just start planning. Your goal can simply be to reach a point where your answer to "what if I can never go back?" is "who cares?"

What if my income drops more than I expect?

Before making any transition, you need what’s called “financial margin.” You need to know you'd be okay earning less than you anticipated.

Start by checking whether your retirement savings are sufficient. The November 2025 newsletter, What is Enough? And Why Knowing Is The Path To Financial Freedom, walks you through exactly how to calculate this.

Then take a close look at your expenses. As you look them over, be honest with yourself about what is and isn’t necessary for you to live a comfortable life.

You’re not planning for frugality. That would just add more stress to any career transition. But you should eliminate any unnecessary excess. With every expense you evaluate, ask yourself, “does this meaningfully improve the quality of my life?”

And, as a mentor once told me, if it isn’t a “hell yes” it’s a “hell no.”

Once you have a clear picture of your monthly and annual expenses, you can figure out your minimum required income. If you have a two-income household, subtract your spouse’s earnings. And you should only leave your job if you are certain you’ll be able to earn more than that amount.

To give you an example, my number was $36k. With a decent amount of retirement savings and spousal income. But $36k was my floor. And that gave me a sense of freedom I hadn’t felt in a long time.

Your number will be different, of course. But you have one, whether you're already there or still building toward it. Knowing it is what turns “what if” into “when.”

How do I explain this to others?

Job titles have a way of becoming identity. So, it's natural to wonder what people will think if you walk away.

Before I made my own decision to leave my former job, I worried about this constantly. So has every career-changer I've talked to since. 

But the people we thought would judge us didn't. If anything, they envied us.

A few months ago, I reconnected with a former colleague. He's making high six-figures now and has moved into leadership. When I mentioned my income still wasn't back to previous levels, I waited for the conversation to get awkward.

Instead, he said, "That's awesome you have time to coach your son's baseball team." Then he told me he wished his son had a better coach, because his kid doesn't even like baseball that much.

The people who actually care about you will be happy you're pursuing a life that makes you happy. So, let me ask you: who in your life might be relieved if you made a change?

What's really holding you back

These questions feel like they're about money and logistics. They're not, at least not entirely. They're really about fear. Fear of the unknown. Fear of judgment. Fear that the life we've built isn't the life we want.

But on the other side of that fear is something most people never experience: the freedom to design your work around your life, instead of the other way around.

You don't have to quit tomorrow. You don't have to have it all figured out. You just have to be willing to start planning for a life that's actually yours.