Questions to Ask Yourself at Every Point in Your Career

When you’re going about your day-to-day, it’s easy to put important questions about your career—what you really want to do, how you get there—on the backburner as you complete the tasks you need to get done now. And who wants to think about work in the few hours we have off?

But getting lost in the daily to-dos means you can miss the bigger picture, and not progress toward accomplishing your larger goals. So here’s a happy medium: On your next Personal Inventory Day or during your next Life Audit, take some time to answer the following questions, depending on where you are in your career.

Entry level

What do I want to be good at?

This is a version of “what’s your passion?” except that it takes the money-making part of the equation into account. You need to work, and more likely than not your job won’t be your “passion” right out of the gate, but there’s always room to grow. So nail down what it is you actually want to be good at. As Allison Jones writes for Fast Company, “[y]ou need to think more concretely about your motivations, needs, skills, and what you’re willing to do–or give up–in order to find that great opportunity.”

Then ask how the company you’re working for (or considering working for) will help you grow. Writes HubSpot’s Katie Burke for Fast Company: “How does the team you’ll be working for plan to grow in the coming year, and what do the prospects look like for growth for the broader company?”

What skills do I need to be good at it?

Once you decide what you want to be good in your career, ask yourself what skills you need to succeed. “Figuring out the skills we want to use and develop and the work we’d like to do takes time and experimentation, but it’s a far more practical way to get closer to what we actually want out of our jobs,” writes Jones.

Once you’ve zeroed in on actual skills you want to attain, you can work toward them and hopefully avoid some of the directionless-ness and misguided purpose some of us feel early in our careers (otherwise known as a quarter life crisis).

What can I do to position myself in the best place possible?

When you’re new, it doesn’t matter much what you accomplished in college or internships. Now’s the time to actually prove yourself and set yourself up for success. And if you start thinking about that early on, it will be easier to do so. What resources does your company offer for ongoing education? What networking opportunities can you take advantage of? Is there a manager you can take out for coffee who could become a possible mentor? Even if you have a crappy first job (and who doesn’t), there will always be things you can learn and people you can leave a lasting impression on.

What role does work play in my life?

Jones goes on to say that it’s perfectly ok if work isn’t your passion—it’s just a means to an end. So ask yourself what role you want it to play in your life. You don’t have to figure this out as an entry-level worker, of course, but it’s a good question to ponder before you move further up the food chain or have a family. “Decide what sort of life you want and what role work will play in it,” says Jones.


What tasks invigorate me, and what tasks drain me?

After you’ve worked a while, you’ll have a good sense of the types of assignments that energize you and those that deplete you. Maybe you enjoy research and putting power point presentations together, but loathe client meetings. Maybe it’s the other way around. Whatever the case, if you nail down what you actually enjoy (or at least, don’t mind) doing, you can use that to inform your progression.

Do I want to be a manager?

This plays into the first question, but deserves it’s own bullet. Now’s the time to decide if you really want to be a manager, and, if so, the steps you need to get there. Also consider, what sacrifices will you have to make in other parts of your life to make it work, if any? What work will you be giving up? On the flip side, it’s totally fine to not want to be management. So be honest with yourself and what you want.

Am I progressing in my career the way I imagined I would?

Once you’ve settled that, you can reflect on where you are in your career and where you’d like to be. Are you happy with your current trajectory? Is the path you’re on still the one you want? If so, great! If not, it’s time to recalibrate. Here are some resources on how to do that: Write your own biography or try this one hour writing exercise.

Is this career allowing me to do what’s important?

Is your career giving you enough money, time and flexibility to do the things in your life that are more important than working? Now’s the time to reflect on what’s important to you, and whether or not you to need to change your life around a bit to focus on those things.

Senior level

In what ways can I still grow?

Just because you’re at the top doesn’t mean there’s no room for improvement. Once you’ve made a name for yourself with the skills you zeroed in on in your early days, you have the opportunity to keep learning and growing, all with slightly lower stakes. So ask yourself if there was something you wished you were good at, or if there’s another industry that’s appealing? Might you want to start your own business or side hustle as a new challenge?

What legacy do I want to leave?

Later in your career, reflect on what you’ve done and in what ways you’ve helped others. Were you a mentor? Did you want to be? Consider your reputation and what you want to leave behind when you retire. It’s never too late to leave a lasting, positive impression.

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