The Super Definitive Guide to Evaluating Your Work Life

When’s the last time you gave your career a check up?

Photo by The Creative Exchange on Unsplash

It is waaayyyy too easy to get caught up in the everyday busy-ness of work and life . . . and suddenly realize that it’s been years since you’ve really paused to examine how your work life is going. Are you on a path that you want to be on? Are you growing in the ways you’d like to be? Do you still have the same priorities that you did when you started on your current path?

It’s incredibly valuable to take an hour or two to slow down and mindfully give some thought to how your work life is going. And what better time than as we approach the end of the end the year, so you can head into the new year ready to work towards any changes that you find you are wanting.

So block of some time all for yourself, put on some calming music, get a cup of tea or (if you’ll stay clear headed) a glass of wine and answer the questions below. Ideally, write out your answers, because you’ll tend to answer more fully AND will have a record you can look back at, rather than just letting it slip from your mind when you return to the pressures and needs of life. Try not to judge any of your answers or to give the answer you think you “should” give. Just be honest and let the answer be ok. I think it can be helpful to view this like an annual physical for your career — or more alliteratively, as a “career check up” to gather important information and stay on top of your career health and happiness.

Let’s get started.

1. If you’re really, really honest, how are you been feeling about your career?

• Do you like your job? Your career?
• Do you get the “Sunday scaries?” (ie, start to dread Monday morning on Sunday afternoon or evening?)
• Have you come to any new thoughts about your work since the pandemic began?
• If you won the lottery, what would you change about your work life?
• What is your definition of success? Is your job empowering you to reach that? Is your career path?

2. What are your priorities for your work and life? Have they changed since the last time you evaluated your career?

• Have you had any major life changes since you last evaluated your job or career? Have you gotten married, had kids, had a parent whose health has started to decline? How do those impact what you want from your work?
• Since the pandemic began, what have you realized you truly care about? Are there things you thought were important to you that you have discovered you really don’t miss?
• If you’ve been working from home, how has that experience been for you? Have you struggled with stopping work? Have you found a lot of freedom that you value?
• Flash forward to twenty years from now. What would you like to say that you have accomplished, both in your work and in the rest of your life? Does your current career empower you to accomplish those things?

3. How do you feel about returning to (more of a) pre-pandemic style of work?

• Are you chomping at the bit to return to the office and get back to the way things used to be?
• Did you move away during the pandemic? Do you want to continue to work remotely? How important is that to you?
• How supportive is your employer of what employees are wanting in terms of continued flexibility and/or remote work? How do you feel about the the way they are responding?
• What do you want to keep from your ways of working during the pandemic? Have you developed new rhythms of life that you’ve found you value? What do you want to ditch as soon as possible?

4. How do you feel about your daily work responsibilities?

• How often do you lose track of time during the workday?
• Are you excited for new projects? If yes, what’s exciting about them? If not, what do you feel when a new project comes up? What don’t you like about it?
• Do like your responsibilities, but feel overworked? Or just as importantly, feel underworked? Is there anything you can do to change that?

5. What goals do you have for the next year of your career?

• Are there ways in which you’d like to be growing? Would you like to improve any skills? Developing your leadership abilities? Taking on any new challenges or opportunities?
• What can you do to make that happen?
• Do you not have any goals for the next year of your career? How do you feel about that? Does that mean anything?

6. What’s missing from your work?

• If you could wave a magic wand, what would you give yourself to make your job better?
• Is that something you could try pursuing in your current position? Or with your current company?
• If not, how much does it matter to you? Is it something you could potentially get at another company? Does it feel like an inherent limitation of your career?

7. How are you feeling about your life outside of work?

• How do you feel about your hours? Vacation time? Flexibility?
• Does your boss respect your personal time?
• How is your energy at the end of the workday? Are you drained and just needing to recover? Do you end the day feeling good and ready to move on to the rest of your life?

8. How do you feel about your organization and its leaders? Your manager? Your colleagues?

• Have you felt like your manager and company have supported you and your colleagues throughout the pandemic?
• If you have kids, did your work support you with them being at home during the last year? How? If not, what did that look like? How did that feel?
• Do your organization’s leaders listen to what workers care about? Do you trust that they care about the employees?
• How do you feel about the direction of the company? The executives’ leadership style? Communication style?
• How do you feel about your boss’s management style? Do you work well with it? Is it making your work life easier or harder?
• Do you collaborate well with your colleagues?

9. If you’re really honest, do you want to be in this job (or career) in another year? In another 5 years?

• Why are you staying at your current job?
• What have you really appreciated about your job during the past year?
• Are there opportunities for growth at your current company that you are excited about?
• Are there opportunities for growth in your career path that you are excited about?
• What would you miss out on if you stayed in your current job (or on your current career path) for another year? Another 5 years?

10. What do you believe is possible for your work?

• Do you believe it’s possible to enjoy your work and still make a good living?
• Do you believe it’s ungrateful or shallow to be unhappy if you have a stable job? (ie, do you think you should “just be grateful” to have a job, especially when so many people have lost their jobs?)
• Do you believe that there is any work you would enjoy? Find meaningful? Enjoy showing up for every day?
• What messages did your parents give you about work? What stories do you tell yourself about work?
• If you were guaranteed not to fail, what would you want for your work life?
• Have you given yourself permission to change jobs — or careers — if you aren’t happy?

And . . . What Now?

Now, you’re in a position to actually make what you want for your work life happen! Maybe you’re wanting some growth and new challenges, which you can pursue by seeking an opportunity to lead a project or go to leadership training. Maybe you’ve found working remotely has been a game changer for your family, and you need to advocate for yourself to continue to be able to work from home. Or maybe you’ve realized you’re feeling unhappy or stagnant and and realizing that it’s time for you to change jobs or pivot your career path.

But big or small, you don’t have to make your goals happen all at once. You’ve taken the first step by getting clear on what’s going on — celebrate that! And keep the momentum going by thinking of a small step you can take in furtherance of your goals within the next week (or during the first week of January.)

Happy Holidays!

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Kelley Shields is a career and life coach who helps unfulfilled professionals find work they find meaningful, enjoyable and profitable. Feeling stuck? Don’t know what you want, but know your current job isn’t it? We should talk. Find me at www.kelleyshields.com