How to Figure Out Whether or Not You’d like Someone’s Job
One of the best ways to figure out if you’d like a certain job or not is to talk to someone who actually does that job.
But what questions should you ask them? How do you figure out how YOU’D feel about that job?
Here is my 3 step process for walking away from coffee chats and informational interviews with more clarity rather than more confusion.
Step 1: Get their circumstances, not their thoughts
Most people, when you ask them about their jobs, will give you their thoughts about their job. Things like:
I really like it! The problems we work on are challenging and engaging. It feels like I’m making a direct impact every day. Sometimes I get frustrated when things move slowly, but we can usually find some quick wins or workarounds and keep things moving.
Now here’s the reality. Their job isn’t really “challenging” or “engaging” or “impactful.”
Their job is a set of factual circumstances and they’re giving you their thoughts about those circumstances.
But you don’t really need their thoughts. You need to know what YOUR thoughts would be if you had THEIR circumstances.
So ask questions that reveal the specific circumstances of their job.
What problems are they currently working on? How did they spend their week or their month? What activities do they spend their time doing — and what are they NOT doing? How are they evaluated?
Here’s what a more circumstance-based answer might look like:
My main priorities this quarter are growing our customer base by 20% and improving the efficiency of our onboarding process.
For the first one, I’m working with our marketing team to launch a new social media campaign. They handle all the creative stuff, like the messaging and graphics. My job is to set up and track the metrics for the campaign and help them make adjustments if the metrics aren’t looking strong.
For the second one, I gathered the data and did the analysis to figure out where people were dropping out of our onboarding process today. And now I’m working with our developers to implement process changes. I don’t do any of the coding — my main role is to go to prioritization meetings and fight for our project to be prioritized.
Step 2: Jot down your automatic thoughts about their circumstances
Once you have their circumstances, notice where your brain automatically goes.
What does your brain automatically like? What does your brain automatically NOT like?
This could look like…
Circumstance: It took us 3 weeks to get that new feature implemented.
Automatic thought: That’s so fast! I love that!
Circumstance: My job is to set up and track the metrics for the marketing campaign.
Automatic thought: Oh, nice! I don’t know much about marketing, but I know a lot about data and metrics. That sounds fun!
Circumstance: My main role is to go to prioritization meetings and fight for our project to be prioritized.
Automatic thought: Oh, that sounds like a lot of influencing and persuasion… I’d rather have direct authority over things.
Circumstance: I spend 70% of my time on sales and customer acquisition and 30% of my time on actually delivering the projects I sold.
Automatic thought: Oh no! I wanted an advisor-type role where I could feel like a helpful expert all the time… But this sounds like a pushy sales role, not a helpful advisor role!
This is the data that you really need in order to make a decision — YOUR automatic thoughts about THEIR circumstances.
Step 3: Sketch out the Thought Mountain you would have to climb in order to enjoy this job.
Here’s the secret: No job is going to make you perfectly happy, fulfilled, or passionate all by itself.
Because remember: a job is just a circumstance. It’s a neutral set of facts happening around you.
How you feel about your job is driven by your thoughts about your job.
And no matter what kind of situation you end up in, your brain is automatically going to give you 50% positive thoughts and 50% negative thoughts.
(Honestly, that’s a generous estimate. My brain usually gives me 80% negative thoughts.)
So the question ISN’T: What job will perfectly trigger my brain to be happy and fulfilled all the time?
That job doesn’t exist. NO circumstance will trigger your brain to be happy all the time, because your brain’s whole job is to flag problems.
I promise you, even if you won the lottery and moved to Hawaii with all your best friends and a supermodel spouse, your brain would still do a stellar job of flagging problems. It’s literally evolved to be that way.
So the REAL question is: In what job do I want to do the mental work of making myself happy, fulfilled, and passionate?
Of appreciating what I automatically like…
And of being okay with OR changing my perspective on the things I don’t automatically like?
Another way of saying this — Which Thought Mountain do I want to climb?
In the example from Step 2, the Thought Mountain might be:
If I want to enjoy this job, I would have to…
Appreciate how fast things move.
Enjoy the fact that I get to work with data and metrics.
Learn how to be okay with operating through influence rather than direct decision-making authority.
Learn how to make sales FUN. I need to figure out how to not see it as being pushy but as an extension of the helpful advisor role that I enjoy playing.
And there might be a different job with a totally different Thought Mountain, that you can compare this to. That job might look like:
If I want to enjoy this job, I would have to…
Appreciate having direct decision-making authority.
Really enjoy getting to spend all my time delivering projects and not having to sell.
Be okay with the fact that things move more slowly than I like
Learn how to enjoy NOT working with data and doing more qualitative work. I need to figure out how to make that just as nerdy and fun for myself as quantitative work.
As you have conversations with people and hear about their jobs, you can sketch out the variety of Thought Mountains available to you and figure out which one you want to climb.
Here’s the other secret: There’s no right or wrong answer about which mountain to climb. They all require about the same amount of effort.
Framing the decision as a choice between different but equal Thought Mountains (rather than a high-stakes search for the “right answer”) helps you take responsibility for creating your own happiness and fulfillment wherever you go…
Rather than outsourcing that responsibility entirely to your job (and then wondering why no job ever seems to solve your problems).
When I say I help people get clear and get moving on their next career step, this is what I mean.
This isn’t about resume reviews or networking tips or specialized interview prep. All those things are awesome too!
But what I’ve found again and again is that’s not actually the biggest blocker for high-stress high achievers trying to figure out what to do next.
You can do the tactical stuff. You have the network. You have the resources. You have the drive and work ethic to make it happen.
The problem is that you’re avoiding doing it, or you’re doing it frantically and taking lots of action but still feeling stuck.
That’s where I come in.
If you’re feeling stuck, it’s always because of something you’re thinking.
There’s some unquestioned story or assumption lurking in your brain, that feels really true, and is keeping you from moving forward with clarity, confidence, and conviction.
I’ve already given you 7 of those common stuck-points in my job search & career change masterclass, along with simple, practical ways to get un-stuck today.
Imagine how much EASIER it gets when you’ve got me in your pocket — customizing everything to YOUR specific situation and keeping you on track and accountable every step of the way.
Don’t spend weeks or months (or years!) trying to figure out what’s keeping you stuck and what to do about it.
I can tell you in the very first session: This is exactly what the problem is. Here’s the solution. Here’s how to implement it. This is how we’ll track progress. Let’s check in next week and see how it’s going.
And the following week, I can tell you: Oh yep, you ran into Common Implementation Problems #2 and #5. No worries. Here’s what to do in this situation. Try this, track what happens, and let’s see where you are next week.
This is why you move faster when you have a coach.
You waste no time wondering what the problem is and getting confused about how to solve it and feeling bad for having problems in the first place.
You can lean on my expertise, pattern-recognition, and deep bank of practical solutions.
Which means you stay laser-focused on identifying and knocking out problems, one by one by one until it’s done.
You can’t afford to wait another day. Let’s get started now.
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