Most of us spend a lot of time thinking about our careers without ever really checking in on them.

You go to work. You finish what needs to get done. Another week passes. Then another month. Then somehow you’ve been at the same company for two years and you’re not entirely sure whether you’re moving forward, standing still, or just really good at answering Slack messages.

That’s why I think every once in a while you need a career check-in.

Not because something has to be wrong. You don’t need to hate your job, be planning to quit, or have some massive career crisis to take a second and look at where you are.

You just need to ask yourself a few honest questions.

A career self-assessment can help you look at your strengths, weaknesses, accomplishments, values, and goals to figure out where you want to go next, according to Indeed’s guide to performing a self-assessment.

So wherever you are in your career right now, here are 10 questions I think are worth asking yourself.

1. Am I Still Learning?

This might be the first question I’d ask.

Are you better at what you do today than you were six months ago?

Think about the skills you’ve developed, the responsibilities you’ve taken on, and the things that used to feel difficult that now feel normal.

Early in your career especially, learning is incredibly valuable. You’re building the skills and experiences that will eventually give you more options.

But sometimes you reach a point where that stops happening.

You know how to do the job. Nothing feels particularly challenging anymore. You’ve stopped getting new responsibilities. You’re basically repeating the same week over and over again.

That doesn’t automatically mean you need to quit.

But it is something worth noticing.

Your career should be giving you something. Money is obviously part of that, but so are skills, experience, relationships, knowledge, and opportunities.

If you’re no longer getting any of those things, ask yourself why.

2. Do I Understand How I Create Value?

Could you explain why your company pays you?

Not your job description. Not your title.

What do you actually do that creates value?

Maybe you bring in revenue. Maybe you manage relationships. Maybe you make something more efficient. Maybe you solve problems. Maybe you create something the company sells.

Understanding this changes the way you look at your job.

“The quicker you figure out how you fit into the big picture, the faster you matter to the company and the more important you become.”

When you understand what matters to the company and how your work connects to it, you can start prioritizing the things that actually make a difference.

That’s a big part of The Secret To Standing Out At Work. The goal isn’t to constantly look busy. It’s to become someone who consistently creates value and who other people know they can rely on.

3. Do I Know What I’ve Actually Accomplished?

What have you done over the past six months?

Seriously.

If your boss asked you right now to list your five biggest accomplishments this year, could you?

A lot of us probably couldn’t.

That’s not because we haven’t accomplished anything. It’s because work moves quickly. You finish one project and immediately start another. Something that consumed your entire life in March is barely a memory by September.

That’s why I’m such a big believer in keeping a running record of what you do.

Projects. Results. New responsibilities. Positive feedback. Problems you solved. Numbers you improved.

“Having this running document will be incredibly helpful for you in everything you do at work.”

I get deeper into this in Why You Should Keep Track of Your Accomplishments at Work, but this is one of the easiest career habits you can start today.

Your accomplishments tell you more than whether you deserve a raise.

They show you how you’re growing.

4. When Was the Last Time I Asked for Feedback?

Not received feedback.

Asked for it.

There’s a difference.

If the only time you find out how your boss thinks you’re doing is during a formal performance review, you’re leaving a lot up to chance.

Ask.

What am I doing well?

Where could I improve?

Is there anything you’d like me to do differently?

And then actually listen to the answer.

“Take it seriously, not personally.”

That’s much easier to say than it is to do. Feedback can feel incredibly personal, especially when you care about your work.

But it’s information.

The goal is to find out what you can improve while you still have time to improve it.

5. Do I Have a Good Relationship With My Boss?

You don’t need to be best friends with your boss.

But you should understand them.

Do you know what they expect from you? Do you know how they prefer to communicate? Can you bring problems to them? Do you trust their feedback? Do they know what you’re working on?

Your relationship with your manager can affect almost every part of your experience at work.

If that relationship feels off, figure out why.

Maybe you need to communicate more frequently. Maybe expectations aren’t clear. Maybe you need more feedback. Maybe you need to take more ownership over your one-on-ones.

And sometimes, yes, maybe you simply have a bad boss.

But before jumping to that conclusion, ask yourself whether there’s anything you can do to make the relationship work better.

6. Am I Building Relationships or Just Doing My Job?

Think about the people you work with.

How many of them do you actually know?

It’s incredibly easy to become transactional at work. You message someone because you need something. They message you because they need something. You finish the project and go back to your respective corners of the internet.

Especially if you work remotely.

But your career is also being built through relationships.

Harvard Business Review has explored how stronger workplace relationships can contribute to connection, collaboration, and a better experience at work.

So talk to people.

Ask someone what they’re working on. Take the coffee meeting. Spend five minutes talking about your weekend before jumping into the agenda.

You don’t need to turn every coworker into your best friend.

You should just avoid becoming someone who only appears when they need something.

7. Does My Job Still Fit the Life I Want?

This one gets overlooked.

A job can be good on paper and still not fit your life.

Maybe you’re making good money, but you’re working until 9 p.m. every night.

Maybe you like the company, but you have no energy left for your friends, dating, working out, hobbies, or anything else you care about.

Maybe your priorities have simply changed.

Your career is part of your life. It isn’t your entire life.

That’s something I get into in How Do You Balance Work, Friends, Dating, and the Gym?. Balance doesn’t necessarily mean giving everything equal attention every day. But if one part of your life is consistently consuming everything else, it’s worth paying attention to.

Ask yourself what you want your normal Tuesday to look like.

Then ask whether your career allows you to live anything close to it.

8. Am I Being Challenged or Am I Just Stressed?

These can feel very similar.

A challenging job stretches you. You’re doing things you haven’t done before. You’re learning. You might feel uncomfortable sometimes, but you can also see yourself becoming better.

Stress without growth feels different.

You’re overwhelmed, but you’re not learning anything. You’re constantly putting out fires. You’re working more without developing new skills or getting more responsibility.

There will be stressful periods in almost every job.

The question is whether the stress is taking you somewhere.

If you’re going through a difficult stretch but you’re learning an enormous amount, maybe there’s value in pushing through.

If you’re miserable and exactly where you were a year ago, that’s different information.

9. What Do I Want More of in My Next Year?

More money? More responsibility? More flexibility? More creativity? Better mentorship? A promotion? A completely different kind of work?

You don’t need to know what you want to do for the next 30 years.

You should probably have some idea of what you want more of over the next one.

That’s where career planning becomes much less intimidating.

Instead of asking, What am I supposed to do with my life? ask, What would make the next year better?

Maybe you want to manage someone for the first time. Maybe you want to develop a specific skill. Maybe you want to make more money. Maybe you want to work somewhere that gives you more flexibility.

Start there.

10. If Nothing Changed for the Next Year, Would I Be Okay With That?

This might be the most important question.

Imagine your job stays almost exactly the same for the next 12 months.

Same responsibilities. Same boss. Same salary. Same schedule. Same problems. Same opportunities.

How does that make you feel?

If your immediate reaction is, Honestly, that sounds pretty good, great.

You don’t need to manufacture dissatisfaction just because the internet constantly tells you to optimize your career.

But if the thought of being in exactly the same place a year from now makes your stomach drop a little, pay attention to that.

That doesn’t mean you need to quit tomorrow.

It means something probably needs to change.

Maybe you need to ask for more responsibility. Maybe you need to have a conversation about compensation. Maybe you need to start developing another skill. Maybe you need to quietly start seeing what else is out there.

You don’t have to immediately know the solution.

You just have to be willing to acknowledge the answer.

And Here’s The Thing

You don’t need to love every part of your job.

You don’t need to know exactly where your career is going.

And you definitely don’t need to have your entire professional life figured out in your 20s.

But every once in a while, you should look up from your computer and ask yourself whether where you’re going is still somewhere you want to go.

That’s the point of a career check-in.

Look at what you’re learning. Look at what you’ve accomplished. Look at your relationships. Look at your life outside of work. Think about what you want more of and what you’re ready to leave behind.

Then make one adjustment.

Because careers usually don’t change through one massive decision.

They change through a bunch of smaller decisions you make after finally paying attention to where you are.

Frequently Asked Questions

How often should you do a career check-in?

Every few months is a good rhythm, and major milestones like a work anniversary, performance review, birthday, or beginning of a new year can be natural times to do one.

How do I know if I’m progressing in my career?

Look at whether you’re learning new skills, taking on more responsibility, creating measurable value, building stronger relationships, and getting closer to the kind of work and life you want.

How do I know if it’s time to leave my job?

One bad week probably isn’t enough. But if you’ve consistently stopped learning, don’t see opportunities to grow, dislike the day-to-day work, or realize the job no longer fits what you want, it may be time to explore other options.

What should I do if I feel stuck in my career?

Start by identifying exactly what feels stuck. Reflect on areas including your skills, accomplishments, strengths, weaknesses, values, and development when assessing your career. Once you know what’s missing, it becomes easier to decide what needs to change.

Do I need to know exactly what I want to do next?

No. You don’t need a perfect five-year plan. Figure out what you want more of, what you want less of, and what the next better step could look like.