Your career is going to take up roughly a third of your waking life. That’s around 90,000 hours if you work until you’re 65. Yet most of us spend more time planning a two-week vacation than we do thinking about where our careers are heading.
Here’s what happens. You get comfortable. The paycheck comes in. Your routine becomes familiar. Then one morning you wake up and realize you’ve been on autopilot for years.
This post gives you 20 questions that cut through the noise and help you figure out if you’re actually building the career you want or just showing up because that’s what you’ve always done.
Questions to Ask Yourself about Your Career
These questions aren’t meant to be answered once and forgotten. They’re tools you can return to whenever you need clarity about where you stand professionally and where you’re going next.
1. Am I Learning Anything New?
Growth happens when you’re stretched. If you can do your job with your eyes closed, that’s a red flag. Your brain craves challenge, and when it doesn’t get it, you start feeling restless.
Think about the last three months. Have you picked up a new skill? Tackled a problem you’d never faced before? If the answer is no, you might be coasting. And coasting feels safe until you realize you’ve been standing still while everyone else moved forward. The people who stay relevant are the ones who keep learning, even when it’s uncomfortable. Even when it means admitting they don’t know something.
2. Do I Respect My Boss?
This one’s huge. You don’t have to be best friends with your manager, but you should respect how they lead, make decisions, and treat people.
If you find yourself constantly questioning their judgment or feeling embarrassed by their behavior, that’s exhausting. You’ll spend your energy managing up instead of growing. A good boss challenges you, advocates for you, and makes you better at what you do. A bad one drains you. It’s really that simple.
3. What Would I Do If Money Wasn’t a Factor?
Strip away the salary, the benefits, the financial pressure. What would you actually choose to spend your time doing? This question reveals what matters to you beyond survival and comfort.
Maybe you’d teach. Maybe you’d build things with your hands. Maybe you’d write or consult or travel and document stories. The gap between what you’d do and what you’re doing right now tells you something important. You don’t have to quit your job tomorrow, but understanding that gap helps you make choices that slowly close it. Small pivots add up.
4. Am I Proud of the Work I’m Producing?
You know that feeling when you finish something and want to show it to people? That’s pride. It’s different from just completing tasks and checking boxes.
If you’re consistently creating work that feels mediocre or pointless, that chips away at you. Quality matters, not because of some abstract standard, but because you have to live with what you make. Your work is an extension of who you are. If it doesn’t reflect your capabilities or values, something needs to change. You deserve to feel good about what you’re putting out there.
5. Can I See Myself Here in Five Years?
Five years sounds far away, but it arrives faster than you think. Picture your life in 2030. Same role? Same company? Same daily routine?
If that image makes you feel trapped or bored, pay attention. Your gut knows things your logical brain tries to rationalize away. On the flip side, if you can see a path forward that excites you—promotions, new responsibilities, expanded influence—that’s a sign you’re in the right place. Vision matters. Without it, you’re just drifting.
6. What Drains My Energy at Work?
Every job has annoying parts. That’s normal. But there’s a difference between minor irritations and soul-sucking activities that leave you depleted.
Make a list. What consistently drains you? Pointless meetings? Office politics? Repetitive tasks that feel meaningless? Micromanagement? Once you identify the patterns, you can address them. Sometimes that means having a conversation. Sometimes it means restructuring your role. Sometimes it means accepting that the drain is too big and it’s time to look elsewhere. Energy is finite. Spend it wisely.
7. Do My Values Align with This Company?
Companies have personalities. They have priorities, cultures, and ways of operating that either match who you are or clash with it.
If you value transparency but work for a company that operates in secrecy, you’ll feel the friction daily. If you care about work-life balance but your company glorifies 70-hour weeks, you’ll burn out. Values alignment isn’t about perfection. It’s about core compatibility. You should be able to support what your company does and how it does it without constantly compromising your principles.
8. Am I Being Paid What I’m Worth?
Money isn’t everything, but it’s not nothing either. If you’re consistently delivering results and your compensation hasn’t kept pace with your contributions or market rates, that’s a problem.
Research what people in your role, with your experience, in your location are making. Sites like Glassdoor, Payscale, and Salary.com can help. If you’re underpaid by 10-15%, that’s thousands of dollars a year you’re leaving behind. Over a career, that compounds. You don’t have to be greedy to advocate for yourself. Fair pay is about recognition and respect.
9. What Am I Avoiding?
There’s usually something. A difficult conversation you keep postponing. A project you’re dragging your feet on. A decision you know you need to make but haven’t.
Whatever you’re avoiding is probably important. It’s creating background stress, taking up mental space, and holding you back. Sometimes the thing you’re avoiding is the very thing that would move your career forward—asking for a raise, applying for a stretch role, admitting a project isn’t working. Avoidance is a signal. Listen to it, then act.
10. Who Do I Want to Become Professionally?
This isn’t about titles or salaries. It’s about identity. What kind of professional do you want to be? Someone known for their creativity? Their reliability? Their ability to solve complex problems? Their leadership?
Your answer shapes your decisions. If you want to be a leader, you need to start leading, even in small ways. If you want to be an expert, you need to go deep and build specialized knowledge. If you want to be an entrepreneur, you need to start thinking like one. Your future self is built by the choices your current self makes. Choose deliberately.
11. Am I Too Comfortable?
Comfort is tricky. It feels good in the moment but dangerous long-term. When you’re too comfortable, you stop pushing yourself. You stop taking risks. You stop growing.
A little discomfort is healthy. It means you’re trying things that challenge you, exposing yourself to new situations, expanding your capabilities. If everything feels easy and predictable, you might be playing it too safe. The market rewards people who stretch themselves, not people who stay in their comfort zones. Comfort is a warning sign dressed up as contentment.
12. What Feedback Do I Keep Hearing?
Patterns in feedback matter. If three different people have told you you’re great at building relationships but struggle with follow-through, that’s data.
We all have strengths and weaknesses. The people who succeed are the ones who acknowledge both and work on the gaps that matter most. You don’t have to be perfect at everything, but if the same critique keeps coming up, it’s worth addressing. Feedback is a gift, even when it stings. Use it to get better.
13. What Would Make Me Excited to Go to Work on Monday?
Monday dread is real, but it shouldn’t be permanent. Think about what would actually make you look forward to the start of the week.
Is it different projects? A new role? Better colleagues? More autonomy? Clearer purpose? Once you identify what’s missing, you can start building toward it. Sometimes it’s possible within your current job. Sometimes it requires a bigger change. Either way, you deserve to feel something other than resignation when Sunday night rolls around.
14. Am I Building Skills That Transfer?
Some skills are specific to one company or industry. Others travel with you wherever you go. Communication, problem-solving, leadership, strategic thinking, and adaptability—these are portable.
If you’re only developing skills that matter in your current niche, you’re limiting your options. Think about what you’re learning and whether it would make you valuable somewhere else. The job market changes. Companies restructure. Industries evolve. The more transferable your skills, the more secure your career. Flexibility is the new security.
15. What Am I Tolerating That I Shouldn’t?
This could be a toxic coworker. Unreasonable demands. A commute that’s killing you. Consistent disrespect from leadership. Whatever it is, you’ve probably convinced yourself it’s fine, or temporary, or not that bad.
But tolerating things that diminish you has a cost. It affects your confidence, your health, your relationships outside of work. There’s a difference between dealing with normal workplace challenges and accepting unacceptable treatment. Stop tolerating what you shouldn’t. Set boundaries. Speak up. If that doesn’t work, move on. Your well-being matters more than any job.
16. Do I Have a Network or Just Colleagues?
Colleagues are people you work with. A network is people who can open doors, offer advice, introduce you to opportunities, and support your growth beyond your current role.
If you’re only connected to people in your immediate team or company, you’re missing out. Networking isn’t about being fake or transactional. It’s about building genuine relationships with people across your field. Attend industry events. Connect on LinkedIn. Have coffee with people doing interesting work. Your next opportunity probably won’t come from a job board. It’ll come from someone who knows you and thinks of you when something opens up.
17. What Success Stories Am I Telling Myself?
Your internal narrative shapes your reality. Are you telling yourself a story about how you’re stuck, underqualified, or unlucky? Or are you focusing on problems you’ve solved, skills you’ve built, and progress you’ve made?
Both stories contain truth, but the one you emphasize determines how you show up. People who highlight their wins—even small ones—build confidence and momentum. People who fixate on their failures get trapped in self-doubt. Be honest about what’s not working, but don’t forget to acknowledge what is. Your story matters. Make it one that moves you forward.
18. Is My Work Making a Difference?
This doesn’t mean you have to save lives or change society. Impact can be smaller and still meaningful. Are you helping customers solve real problems? Supporting a team that’s building something valuable? Making processes better so others can do their jobs more effectively?
Feeling like your work matters is fundamental to satisfaction. If you can’t connect what you do to any meaningful outcome, that’s a problem. Purpose doesn’t have to be grand, but it has to exist. Find the thread that connects your daily tasks to something bigger. If you can’t find it, maybe it’s not there.
19. What Would I Regret Not Trying?
Regret is future pain delivered by present inaction. Think about your career five or ten years from now. What might you wish you’d attempted?
Starting that business? Pursuing that promotion? Switching industries? Learning that skill? Moving to that city? The things you don’t try are often the things you regret most. Not every risk pans out, but you can live with failure. It’s harder to live with wondering what might have been. Permit yourself to try the thing that scares you.
20. Am I Happy?
This seems obvious, but it’s the question people forget to ask. We get so focused on advancement, stability, and meeting expectations that we forget to check in with ourselves about the most basic thing.
Happiness at work doesn’t mean every day is perfect. It means more good days than bad. It means feeling valued, challenged in the right ways, and aligned with what you’re doing. If you’re consistently unhappy, no amount of money or prestige will fix that. Life is too short to spend it miserably. You’re allowed to want more than just a paycheck. You’re allowed to want fulfillment.
Wrapping Up
These twenty questions aren’t a test you pass or fail. They’re mirrors that reflect where you are and where you’re heading. Sit with them. Answer honestly. Some responses will reassure you. Others will make you uncomfortable. Both are valuable.
Career clarity comes from asking hard questions and acting on what you learn. You don’t need all the answers right now, but you do need to start asking.