Thinking About "Graduating From Your Job? Here's Your Sign.

Graduation season is here, and it’s a momentous occasion for so many. They’ve experienced so many trials and tribulations to be able to hear Pomp and Circumstance being played for them. Long nights in the library, building friendships and relationships, and testing the waters of the “real world.”

They are about to enter a realm that feels both freeing and scary. It’s a place where your potential, and many pressures, collide.

Sometimes, when we’ve been in our careers, we think that this is it—this is all we’re going to do. And maybe, every so often, we wonder:

Is it time for me to graduate from my job?

Is it time to reassess where my career is heading?

It’s not an odd notion. Sometimes, we’ve done as much as we possibly could in our field. And we look around and wonder—what’s next for me to do? What else is out there that excites me? What dream have I put into a box, that it’s now time to take the lid off?

What’s holding me back from chasing that dream?

And that’s the holdup, isn’t it?

You may be thinking, I want to graduate from this job. But I’m scared to. It’s stable, it provides for me and my family. How can I jump without a net?

And how can I change lanes in the middle of this highway I’ve been racing down for decades?

Life situations may be a roadblock in the way when the realities of adulthood—responsibilities, expectations, financial commitments—weigh a lot more than our desire to try something new.

If that’s the case, then what can you do if you’re ready to graduate from your work?

Here are three common reasons people hold back from “graduating” from a job, and what to do about them:

You think it’s too late to start over.

This is a big one. You’ve built a whole identity around what you do. Maybe you’re the editor, the producer, the manager who always knows the answer. Changing careers can feel like you’re erasing all that.

Here’s what I want you to know: You’re not starting over. You’re starting from experience.

Everything you’ve done—every challenge you’ve solved, every project you’ve led, every hard conversation you’ve had—that all comes with you. Instead of throwing that out, you’re now repurposing it.

Overcome it by reframing what you know.
Ask yourself: “How could I use what I already know in a new context?” If you’ve been managing teams, maybe you’re ready to consult. If you’ve been storytelling in journalism, maybe you’re ready to apply that gift in marketing or advocacy. The skills are there, you just have to see them through a different lens.

You’re scared to let go of the steady paycheck.

That fear is completely valid, especially in today’s uncertain economy. Bills are real. Responsibilities are real. And you’ve worked hard to get to where you are.

But holding onto something just because it’s safe is like staying in college forever because the dining hall food is predictable. At some point, you’re being called to something bigger.

Overcome it by getting on the runway.

Many times, we feel like we have to leap without a net. But that’s not really the case. You can build a bridge. Start exploring. Take a course, do some contract work, build up a savings buffer. Career change isn’t always about ripping the Band-Aid off; it’s about building a path that supports the version of you that’s coming next.

You’re waiting for permission.

Maybe no one around you is making a move. Or maybe people are moving, and it makes you feel behind. Either way, you’re waiting for a sign—something or someone to tell you: “It’s okay. You can go now.”

Here’s that sign.

Overcome it by trusting your own timing.

There’s no right age, no “correct” moment to change. There’s only the moment when the desire becomes louder than the fear. That moment might be now.

Here’s the thing about a graduation: it’s a ceremony, yes. And, it’s also a commencement.

A beginning. A new chapter.

If you’ve been wrestling with whether to stay or go in your career, maybe you’re at your own personal commencement.

And maybe it’s time to step off one stage, and onto one that best suits you.

I’m Richard Taliaferro. I’m a certified career and health coach specializing in helping mid-stage professionals gain clarity on their career journey. I’ve written a guide on how to escape the work hamster wheel. Click here to download yours.