5 Questions You Should Ask Yourself About Your Job Right Now

If your goal this year is to get ahead in your career, you need to know the answers to these questions.
Answering these critical career questions will teach you what actually matters — or what seems productive but is actually a waste of time.
Maria Stavreva via Getty Images
Answering these critical career questions will teach you what actually matters — or what seems productive but is actually a waste of time.

The new year is a time for resetting and reflecting on the year ahead. And for many of us, our careers can be a big pain point or a confusing open question.

“I know I want to change up my job, but I don’t know where to start,” you might think. Don’t worry: Help is on the way.

Before you commit to a work-related resolution, figure out what you actually need to change first so you can start the new year ahead of the curve. HuffPost asked a variety of career experts the most critical question professionals should ask themselves if they want to level up this year and why. Get out your journals and be prepared to take notes.

1. ‘What do I want to do more or less of this year?’

Angelika Karachristos, associate director of talent acquisition for the University of New Haven, said an important question professionals can ask themselves to level up this year is, “What do I want to do more of?” as well as, “What do I want to do less of in my current role?” This way, you can clarify what you want out of your next move.

“Leveling up just for the sake of it can still leave professionals feeling unfulfilled if the move didn’t lead to more of the work they want to do,” Karachristos said. “On the flip side, [knowing] what you want to be doing less of can be a powerful motivator.”

Reflecting on this question can be a win-win for you and your employer. If you’re dissatisfied with your current job, it can help you target your job search for the next role. And, in the meantime, sharing what you learn can help your manager set new goals with you that you actually want to accomplish.

“For example, if you want to do less administrative work in your role, perhaps trying to find ways to improve processes or collaborate with others will showcase your initiative and leadership skills in a way that will lead you to a new role,” Karachristos said.

“These are great questions to discuss with your manager as part of your development planning. Specifically knowing what work you’d like to do more of can be very helpful to your manager in providing opportunities for development, projects and assignments,” she added.

2. ‘How can I increase my visibility at work?’

“In order to advance our careers, we should continually ― or at least periodically ― be thinking about who we are visible to. ‘Are we visible to enough people, are we visible to enough of the right people?’ Because in work and career, people hire people, people promote people, people amplify people,” said feminist career strategist Cynthia Pong.

“Essentially, the more of the right people you’re visible to ― in the way that you want to be seen ― the better ‘insurance plan’ you have for your career. And the next time there’s mass layoffs, budget cuts, an economic downturn, the faster you’ll be back on your feet and the more of a cushion you’ll have should you be subject to any of those things.”

3. ‘What’s my one big win this year that will make 2024 a year to smile about?’

Sometimes it can be clarifying to visualise your best-case scenario. Gorick Ng, a career adviser at Harvard University and the author of “The Unspoken Rules: Secrets to Starting Your Career Off Right,” said the question he encourages professionals to ask, as if looking back at year’s end, is: “What’s your one big win this year that will make 2024 a year to smile about?”

“Do you hope to have led a certain project? Presented at a big conference? Become the mentee of a certain higher-up? Built a deeper relationship with a certain co-worker? Moved to a new city? Gotten promoted? Started a side hustle? Be exercising five days per week?

“Close your eyes and really picture the life you want to be living. Then write it down. ... Stick it on your bathroom mirror. Do whatever it takes,” he said.

Similarly, career coach Jasmine Escalera said she asks clients to visualise what it would feel like to have achieved the best year of their professional life and then ask themselves: “What happened?”

She said this question helps people clarify: “What are the commitments that you need to make to yourself to be able to achieve those goals? Who do you need to be? What mindset do you need to have? What habits do you need to adopt in order to achieve this?”

“Someone who has achieved the goal before can tell you what actually matters and what seems productive but that is actually a waste of time.”

- Gorick Ng, author of “The Unspoken Rules: Secrets to Starting Your Career Off Right"

For those who have a big goal but don’t know where to begin, Ng said a great first step is to find someone who has achieved such a goal, like a “near peer —someone just a few steps ahead of you and is invested in you and doesn’t see you as a threat.”

Request a brief conversation and ask that person how they did what you want to do. “Someone who has achieved the goal before can tell you what actually matters and what seems productive but that is actually a waste of time,” Ng said.

If you’re shy on what to say to this colleague, Ng shared the template of starting with: “At the top of my new year’s resolutions list is to [ ]. I immediately thought of you, given that you’ve [ ] and are the master of [ ]. Might you have a few minutes to chat? I’d love to follow in your footsteps!”

Escalera said you can use the beginning of the year to reflect on potential logistical or mindset challenges to your big goal. If you know you want a promotion by the end of the year, for example, you can then start “to gain and hone some of the skills necessary to be a leader.”

4. ‘What’s my reputation at work?’

Jenny Fernandez, a leadership coach and startup mentor for the entrepreneur accelerator program Techstars, said this question can give you clarity on if how you see yourself aligns with how people in power are seeing you, too.

Fernandez, a Latina, said professionals from underrepresented communities like herself can make the mistake of believing “our work should speak for itself.”

“The challenge is that then management or HR or leaders may think that you’re comfortable where you are or that you’re not expecting the promotion soon, so you can wait,” she explained.

To find answers to this question, it’s going to take some detective work. Beyond looking at the feedback from your performance review, Fernandez suggested identifying three to five people who can be honest with you and letting them first know that you trust and value their opinion. That way, “they feel safe to give their opinion,” Fernandez said. “Then ask them: ‘What are three words that you think best describe me.’ And if you get those three words from three to five people, you’ll have a lot of data that is going to give you concrete information about what they think about you.”

If you know people who get promoted are known as collaborative, strategic and analytical, and those are not the words that co-workers are bringing up, then you know you have a mismatch you need to address, Fernandez said.

5. ‘What fills my cup?’

Before you put your all into a new goal, figure out if it will align with what nourishes and restores you.

Licensed clinical psychologist Cynthia Shaw said asking yourself “What fills your cup?” can help you reflect and better identify what you are looking for professionally, “whether that be making financial strides or gaining promotional shifts, taking part in entrepreneurial startups or nonprofit volunteer opportunities, or learning how to incorporate better work-life balance.”

To make these desires more concrete, it can help to trace their source. Take wanting to be more successful, as one example.

“Does being successful mean making a lot of money, or does it mean making impactful change? Does it mean feeling purposeful in life or does it mean having time for things outside of work?” Shaw said to ask yourself.

“If being successful means making a lot of money, as an example, what is a lot of money? ... When is it enough money, and what about making money means you are successful? Furthermore, it may be helpful to ask yourself what has influenced this view of success.”

In this way, you can use the beginning of the year to set yourself up for a year of wins that will actually feel rewarding in the long run.

Give yourself grace if the challenge seems daunting. Finding the answers to these questions might not all happen in the first month of the year, but asking them now can give you a holistic view of where you are today and who you can become tomorrow.

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