Perform a “Career Check-up” with these 5 questions

The same way that we visit the doctor and dentist annually to make sure we haven’t completely combusted into a pile of deteriorated skin and bones - we should be checking in on our career’s health too.

If you’re the type of person who skips those doctor visits already (I’m not sick, everything is fine - my elbow bends great!), you might be due for a check-up. On your health… and your career.

It’s hard to create a relationship with ourselves to be reflective, introspective, and curious about what we want. When we’re on autopilot, we like to avoid stepping back and reviewing the landscape. But, if we don’t, it might become a trip to urgentcare when we realize we’re miserable.

So, consider this an invitation to check-in with yourself.

What is a Career Check-up?

A career check-up is exactly what it sounds like. It’s taking stock of what’s been happening, what direction things are heading in, and how to take good care of yourself. Similar to when you visit the doc they ask you about your habits, lifestyle choices - they also ask you “do you have any questions for me?” That’s the part of the visit that we often say, “uhh… no?” In truth, it’s the best part of a doctor visit. You’re sitting, with an expert, naked in a paper gown, and you can ask them anything you’ve been secretly googling on webmd. So take the moment to check-in on your check-up.

Why are Career Check-up’s important?

We rarely pause to take stock of our lives. We’re often going and moving so fast that we skip it. And then it hits us all at once. Think about it - the world was built around immediate gratification. Crash diets, get-rick schemes… we’ve been taught to make changes right when think of them.

Instead, taking time to sit, think, wonder… it gives us the tools to continue to examine our livelihood in a proactive, thoughtful way. That’s a far cry from the reactive knee-jerk way most of us furiously floss the day before our dentist visit. (They know you don’t floss by the way.)

I’m in. How do we do it?

The best way to do a career check-up is the same way we set up any habits. We need to create the time, space, and supporting tools to make it easy.

Let’s get to it. Follow the three steps below!

Step 1: Schedule it

First things first. Schedule your career check-up. Pick a time that makes sense for you. It is annually? Twice a year? Quarterly? Monthly? Whatever you choose, make it happen. If you decide annually - do it before your annual performance reviews. It’s a great way to check in on your career before the rest of your team tells you what to think and you get sucked into wanting a promotion before you know that you want a promotion.

Step 2: Ask these 5 questions

For your career check-up, you can technically ask yourself anything, but here are the five questions I like to ask myself:

1. Am I being challenged? Am I continuing to grow, learn new things, find ways to feel productive? Do I feel like I’ve hit a plateau? That I’m phoning it in?

2. How excited am I about the next level? When I look around for what that next step is… do I get excited? Do I get stressed by the idea of that role? Would I want something different if I had a choice - and I can have that, instead?

3. Do I want to go to work 80% of the time? When I wake up, am I excited about starting my day? (Please note - no one wants to go to work every single day every single minute. It’s normal to have moments in the day, the week, the month, or the year that you’re less excited about work. What we’re trying to diagnose is if, on average, you like the work that you’re doing.)

4. Does this path still meet my life situation? What has changed in my personal life that may impact how I feel about my work? Am I interested in making more money? Working less? Having hybrid/remote options? Do I want to be able to travel to Europe for 3 months out of the year? Do I need more flexibility? Do I want better benefits? Do I have a mortgage? Aging parents?

5. Am I supported? Do I feel like I have people, colleagues, managers, mentors, sponsors, team members in my corner? What can I do to find and grow my support network to create a strong sense of home where I work?

You can ask yourself anything you want - but these are a great litmus test to check-in and start the self-discovery we need to assess what we want.

Step 3: Track it over time

The secret sauce of this practice is that we get to continue to reflect on what we think. I personally keep an “Of Interest” folder in my google drive that lets me double-check how I’m feeling about my path as I move forward.

Want a deeper diagnosis? You can take the 15 Questions to Career Clarity challenge:

Or take it even deeper and have a discovery call to air out all your skeletons: