Considering a Career Change? How to Know What You Really Want Next

There comes a point in many successful careers when a question starts quietly showing up: “Do I really want to keep doing this?”

Maybe you’ve spent ten or twenty years building your career. You’re good at what you do, you’ve developed valuable expertise, and you’ve created a lifestyle that depends on the income you earn. Walking away from all of that doesn’t feel particularly realistic. At the same time, another thought keeps coming back: “I need the money, but I don’t want to do this work forever.”

When someone comes to me at that crossroads, I don’t think the first question is whether they should stay or leave. I think we need to step back and understand why they want something different in the first place.

Maybe the job simply isn’t fulfilling anymore. Maybe every day has become monotonous and there’s a feeling that you’re no longer learning or growing. Perhaps the problem is the relationships or environment at work. It could even be that you’re looking at the future of your industry and wondering whether you want to spend the next decade there.

Or maybe you’ve reached the uncomfortable realization that your ladder has been standing against the wrong building.

Those are very different reasons for wanting change. And until you understand what’s actually making you question your career, it’s difficult to know what kind of change you need.

Once we understand what isn’t working, I think the conversation needs to go deeper than simply looking for another job. It becomes a conversation about who you are today.

That matters because we can become very attached to what we’ve already invested. Someone might say, “I’ve been doing this for twenty years. I invested so much of myself in becoming good at this.” Or perhaps you spent years studying for a particular profession, and leaving it feels as though you would somehow be walking away from everything you worked for.

But the person who studied law years ago may not actually want to be a lawyer anymore.

That doesn’t erase everything that came before. It simply means that who you are today may be different from the person who made that original career decision. Life develops. We develop. The world around us changes. Even the geopolitical environment we live in can cause us to question whether the values and beliefs that once guided us still sustain us in the world we live in now.

So instead of immediately asking, “What job should I do next?” I would ask something different: “Who am I today?”

And then I would take money out of the equation for a moment and ask, “If money were not an object, where would I go? What would I do? And why would I do it?”

The “why” is especially important because it starts uncovering your values, desires and beliefs. It can also reveal things you would happily do even if nobody paid you to do them.

From there, you can begin exploring possibilities. And this is where people sometimes make career change much more dramatic than it needs to be.

You don’t necessarily need to be the corporate lawyer who suddenly quits everything to become an outdoor YouTube creator. Maybe that is somebody’s path, but meaningful change can also be much smaller.

Perhaps you need a different environment. Maybe you need a different schedule. Maybe there’s another role where you can use many of the skills you already have, but in a way that fits who you are now. There may be possibilities you’ve simply never considered because you’ve spent so long looking at yourself through the lens of the career you already have.

Sometimes a relatively small shift can make a huge difference.

Only after exploring those questions would I bring the practical realities back into the conversation. Of course, money matters. You need to understand your financial situation and what it takes to sustain your lifestyle. You also need to think about your desired outcome and what kind of change is realistically available to you.

But there’s another reality worth considering too: time.

Do you want to stay where you are for another five years? Ten? Twenty? For some people, perhaps another thirty?

If the answer is no, then maybe the question isn’t whether you should abandon everything tomorrow. Maybe the question is whether it’s time to begin moving toward something that feels more meaningful and more resonant with who you have become.

And if you’re still struggling with that decision, there’s one final exercise I would suggest.

Imagine yourself thirty years from now. Imagine it is your last day on Earth and you’re looking back at this particular moment in your life. You remember knowing that something didn’t feel right. You remember wondering whether you should make a change. You also know, looking back, that you had an opportunity to at least attempt one.

What would you regret more?

Would you regret making the change?

Or would you regret knowing that you wanted something different and never attempting to find out what it could have been?

You may not know exactly what’s next yet. That’s okay. Sometimes the first step isn’t finding the answer. It’s becoming willing to ask yourself the questions that can eventually lead you there.

If you’re at this crossroads in your own career and want help figuring out what’s next, let’s start here..