The Must-Answer Questions You Should Ask Yourself About Your Career (at least once a year)

career goals career path Feb 06, 2020

In this post

1) Why it's so important to know where you you want to go with your career and not leave it to other people

2) How I fell into this trap (an example of what NOT to do)

3) The 20 questions to ask yourself, in order to get back into the driver's seat

Why career clarity is a must

In last week's post (, we discussed the importance of working ON your career, not just in it.

One of the key steps to working ON your career, is to know exactly what you're trying to achieve. This will give you a map from where you are to where you want to be.

Today I am asking you - what do you REALLY WANT from your career?

  • Money?
  • Fulfillment?
  • Significance?
  • Accomplishment?
  • All of this in some form?

Having clarity on exactly WHAT YOU WANT from your career and for your life, is the only way you're going to achieve these goals.

Yet, you probably don't take the time to think about the bigger picture - what you want, why you want it and how to get it.

Most people don't. (I didn't either but more on that in a minute).

Are you thinking things like:

  • If I keep my head down and deliver, I'll get recognized (promoted, more money, etc).
  • If I meet the goals and objectives the company has given me, they'll reward me.
  • I'm sure the next opportunity will come my way when the timing is right.

I fell into this trap too

I thought all of these things too.

I was so consumed by the day-to-day that I had lost sight of the big picture.

I worked myself into the ground, focusing on hitting our monthly, quarterly and annual goals. 

And, I did get a lot of what I wanted - money, titles, ownership of mission-critical projects, etc.

But, at the same time, I didn't see how much I had compromised of myself until it was almost too late.

  • I was run-down. 
  • I was very unhealthy.
  • I was just surviving day-to-day, hoping to make it through the gauntlet of meetings and have enough energy to play with my 1 year old and husband before we all crashed and had to get up tomorrow to repeat the same thing.

I was living the ultimate groundhog day life.

Where I went wrong in all of this (looking back of course), is that I didn't take a step back to look at what I was doing, why I was doing it, and what would be the best fit for me in that phase.

  • I didn't consider the work-life balance I wanted and if it was possible.
  • I didn't notice that I had hit my peak several years earlier and was staying for reasons that didn't align with who I am at the core:
    • loyalty (to a detriment), 
    • the money and
    • a comfort zone.
  • I didn't even open up the possibility that another company would be the best next move for me.

I just kept going on that hamster wheel, focusing on pure survival.

What is your current story?

What is your current career story?

  • Are you surviving day-to-day like I was?
  • Do you feel content where you are, but secretly want more?
  • Are you afraid to explore other opportunities because you feel so loyal to your current company/boss?
  • Are you holding back on going all in on a job search because you're afraid to fail?
  • Do you question whether you can repeat your success?

If you can relate to any of this, or you simply haven't taken time to work ON your career in awhile, here's where to start.... ask yourself these 20 questions (and don't be afraid of the answers.)

The 20 questions you should ask yourself about your career (at least once a year)

1) Have I stayed at my current job too long? Why? Why not?

2) If I leave, what would I be running toward?

3) If I leave, what would I be running away from?

4) What's left for me to accomplish in my current job?

5) What was my predominate feeling last year? last month?

6) What predominate feeling do I want?

7) What's my greatest fear about staying?

8) What's my greatest fear about leaving?

9) What's missing from my career right now?

10) What do I have in my career right now that I'm taking for granted?

11) What do I really want in my career but have given up on?

12) What would I choose to be doing if I new I wouldn't fail?

13) If staying in my current role AND leaving for a new job would both turn out to be amazing, which would I pick?

14) What does my best week look like?

15) How is it possible to achieve my best week in my current job?

16) Where am I failing ahead of time in my career?

17) Where am I not giving myself credit?

18) Where am I blaming external things for me not reaching my goals? (e.g. my boss, my co-workers, my clients, my company, my family)

19) What does it look like and feel like when I'm at my best?

20) What do I plan to celebrate at the end of this year?

Answering these questions will give you clarity, direction and purpose.

Then, after you have your answers (it will take several sessions), map out your plans to achieve what you want.

Do you need help with this?

This list of 20 questions is a great starting point.

It's easy to get stuck when you're so far in your own details and thought processes.

I can help you get out of that as neutral, expert sounding board and professional question-asker. If you'd like help, set up a Career Strategy session where we can dive into your specific details. Here's the link to find a day/time that works for you:

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