9 Questions You Need to Ask About Your Career

Do you have big questions about your career? (or lack thereof)

Searching for a career is more than just finding a job, it’s about finding a place to call home where you can thrive and grow in.

I believe it should matter that you want your work to matter.

You will spend more time working than you will anywhere else. Don’t you think it should feel like a good fit, instead of something that’s forced? If you’re always trying to kill time at work, what does that say about the way you’re spending your life?

If you’re struggling with your current career, are confused about the direction it’s heading, or just want to re-confirm you’re on the right one, here are nine questions you need to ask.


1. Are the people who have obtained success in your career path, you know, actually happy?

When you look at the higher ups in your field of work, the people who have really made it, are they happy? Are they living a life they enjoy or are they doing just the opposite?

As I wrote in twentysomething problems, if the thought of doing your bosses job 15 years from now makes you throw up a little, then maybe that’s a sign you’re in the wrong job.

2. The moment right before you enter into your day’s work, how do you feel?

Tomorrow right before you begin your work, pause, ask yourself this question, and see what you say. Are you excited? Anxious? Overwhelmed?

You might be surprised that you find yourself thrilled to begin another day of work. That’s a great sign! Or maybe you notice that dread is slowly wrapping its fingers around your neck?

How you feel the moment before you begin your day will tell you a lot about how you will feel when your day ends.

3. What’s your Dread/ Tolerate/ Love breakdown?

Let’s make a chart! This will be fun!

Look at a typical work day. Break down each hour. From email, to meetings, travel, and then when you’re actually plugging away at the work you’re supposed to be doing.

Looking at your breakdown, how many hours would you place in each category – Dread, Tolerate, and Love.

Now take your hour breakdown and make it into a pie chart. Does this pie chart make you nauseous or happy? If your day is filled with more dread than love, is there a way you can tackle more projects in your “Love” category?

Is there a way to spice up some of those Tolerate hours to make them fit better within your wheelhouse? Or is this career taking up permanent residence in the Land of Dread.

Define what you love about your job and then refine your job to do more of what you love. (tweet that?)

4. Or do you feel you’re full throttle-ly (that’s a word, right?) employed in a crappy job and it would take an act of God to help you enjoy it?

A crappy job can feel like a black hole — it sucks and feels impossible to escape.

Yes, working a crappy job is a twentysomething rite of passage. But how do we make it smell a little better?

The key to working a crappy job, and then leveraging that job into a better one, is to find and hone your One Thing.

Find and focus on the One Thing you like about this job.

Then do that one thing even better than before. Grow your skill-set there. Learn from co-workers who do that One Thing well.

Make that One Thing your crappy job trampoline, bouncing you to greater heights.

Your twenties are about putting in the work now so that you can enjoy your work later. (want to tweet that?)

Too many of us want to escape our crappy jobs before we’ve grown in a skill-set that we can leverage into a better opportunity. If you leave your crappy job without learning and growing, chances are another crappy job awaits.

5. Does studying, researching, and becoming more proficient in your career give you energy or drain it?

Does learning about your industry or craft give you life or take from it?

If becoming a master of your craft is something you’re avoiding, it’s either time to fully dive in or it’s time to pick a new craft.

6. Does this career path create the life you want?

Sometimes you can have an amazing career, but the wake from it is choppy and uneasy.

Do you love your job, but it’s pretty much a given that you’re working 70 hour weeks? And your boss works 80. Or maybe your career is filled with purpose and passion, yet it doesn’t really pay the bills? Basically, what’s most important to you? If you’re not sure, maybe start with these 11 questions every twentysomething needs to ask and then come back here.

It’s a strange paradox when you love your job, but you don’t love the lifestyle it creates.

Choose a healthy life, not just a successful career. 

This might mean you have to make a difficult decision about the kind of life you want to live. But I promise it will be easier to make that choice now, than when a house, spouse, and a few kids are in the picture.

7. Are you doing work that matters? Do you believe in it? Should you believe in it?

Boomers and Millennials especially sometimes find themselves at a disconnect when it comes to career choices.

And it seems whether or not you should have purpose and meaning in your career is at the heart of the debate.

I believe it should matter that you want your work to matter. (tweet that)

For many twentysomethings, they are more focused on finding a job filled with purpose and passsion, than a healthy paycheck.

As a recent Barna study on Millennials states: “When it comes to work and career, more than anything this generation wants to be inspired. Finding a job they are passionate about is the career priority Millennials ranked highest.”

For me personally, doing something that makes an impact in a meaningful way was a number one priority for me. It was a non-negotiable. And it’s compelled me to make hard choices away from comfort and job security. It’s led me through seasons of unemployment and utter leanness. And it’s meant a lot of early mornings and late nights working at a dream, before I went and worked at my work.

This path towards meaning has not been easy, but I love where it’s led me.

8. What are the top skills that you currently using and growing at your work? Are those skills you want to be harnessing and focusing on?

Write down the top 3-5 skills you’re using and developing at work? Or if you’re not working, the top skills you’d like to be developing.

Are those skills you want to be developing? What deeper values are those skills tied to?

I’ve found that many people get stuck in their jobs because they are doing something they find success in, yet they feel this undercurrent of discontent and frustration because the skills they’re using are tied into anything deeper.

Success in your skill-set alone is not your purpose. Your skills should be infused in pursuing something purposeful, but your skills are not your purpose in and of themselves.

Sometimes what we’re good at can become a comfortable trap from living a life away from our true purpose because we’re using skills apart from what we think is important — our “why” – our full Signature Sauce.

9. Do you even want a career?

Career sounds stuffy and inescapable like getting lost in the back of your Aunt Martha’s closet.

The world is flat now with the ability to work anywhere, on anything, at anytime. I’m not sure the standard ideas and concepts behind a linear career are completely relevant any longer.

I don’t think our generation will as readily climb the ladder. Our generation will swim from island to island, picking up necessary skills and experiences as we travel towards our Promised Land.

Right now take the time to answer a few of these questions within the comments on this article at All Groan Up. I promise it’s worth the time. Be intentional about your career and watch the doors begin to open.

And I’d love to give you feedback on at least one of your answers in the comments section.


  1. Jef Miles

    Brilliant content Paul.. Where/how did you put this all together?

    I would love to individually answer all of your questions but for me briefly yes I am doing a job I enjoy and enables me to live a comfortable (very) life however I am not 100% passionate about it, which is why I have my career coaching site..

    Looking forward to reading more from you and would love to have a chat at some stage.. Am going on holidays now for 5 weeks but will reply upon my return 🙂

  2. gonzomatic

    I look at my dad who’s in his mid 50’s and he seems rather miserable in his career. Then again i look at a lot of 50 somethings and wonder if it’s even worth living past 40… help

    • Paul Angone - All Groan Up

      That’s why we need to be intentional with our career, right now, no matter the age you’re reading this at. If not now, when?

  3. Mike Nopper @ BigLifeGrowth

    Awesome writing, Paul.

    I love the use of exercises rather than just spitting out information. It really helps the reader internalize the concept when they have to think about their own situation.

    Speaking of concepts, it blows my mind that we’re not taught to practice self-awareness in our early years. A lot of what I got from this post was the importance of looking inward, and yet the it seems to be nonexistent in the education system.

    Over at BigLifeGrowth I like to work with principles and show others that this can be applied to career development as well as many other areas of one’s life.

    Thanks again for the great content!

  4. José

    Very grateful to your article. I spent 10 years in a job I hated. I went into depression and almost lost my marriage. Until the day I realized I was on the wrong track and that much of my day was doing something I did not like. It was not my way. At that point, I should have read your article. I’m sure it will suit a lot of people. Thank you


Submit a Comment

Your email address will not be published. Required fields are marked *

You’ve got questions.

We’ve got your-


SurVival PAckAge

A free, super-stuffed care package of resources to help you get through your twenties (and thirties too).

Order my new book "25 Lies Twentysomethings Need to Stop Believing"!

25 signs its a quarter life crisis

Instantly access: 

- "3 Ways to Pay Better Attention to the Answers Right in Front of You" - a quick, three step action guide to paying better attention that you can implement today.

- The first two chapters from best-selling author Paul Angone's new book Listen to Your Day: The Life-Changing Practice of Paying Attention.