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Avoiding the comfort trap

A picture of Steve Jobs, co-founder of Apple. He is holding an iPhone on stage at an Apple event, but the photo is tightly cropped, showing only his shoulders and above.

There’s a quote floating around the internet that is supposedly attributed to Steve Jobs and although I confess I don’t know if he ever said it, I like the sentiment regardless of the source. It goes something like this -

For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today? ’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something

As a hiring manager, I take part of dozens of interviews per month, and since I see them as a chance for a candidate to interview me as much as I’m interviewing them, I always make a point of dedicating a certain amount of time for them to ask me questions without interruption.

The questions are varied, ranging from “how does career progression work there?” to “what’s an average day for your team?“. Regardless of the question, most of the time it’s the candidate trying to assess if the job I’m offering is right for them, and that’s exactly the kind of question I think they should be asking.

But it’s important to remember that we should all have a consistent set of questions we would ask if we were interviewing for a new role, and we should ask ourselves those questions about our current job, answering as honestly we can. We should have a similarly objective way to grade the responses.

Heck, if you have a strong enough relationship with your manager, you should even feel comfortable asking them those questions from time to time.

And if you find yourself consistently not liking the answers you get, then maybe it’s time to start looking around for a new opportunity. Sometimes people stay in jobs not because they enjoy the work, or they’re growing, but because change is hard, and the path of least resistance is to just maintaining the status quo.

Changing jobs, or even careers, is not always a comfortable or easy thing to decide, and for many it’s not a luxury they might have, but if you work in technology there’s a non-zero chance that you have that level of job flexibility, and you should take it whenever makes sense, because you might not have that flexibility forever.

I can’t tell you what the right questions for you are, because everyone looks for different things from work, but you should try to figure out what makes you happy. Maybe it’s learning new things, maybe it’s having more impact, maybe it’s making enough money so you don’t have to answer to anyone again. I spoke a bit about these in the past but it’s a very personal thing, so figure out what works for you.

So my advice to you is this. Imagine you were being interviewed tomorrow. What questions would you ask of your interviewer to decide if it was the right job for you? Write them down, and write down the best possible answer. Now ask yourself those questions about your current role. If you don’t like the answers, well that’s an answer all by itself isn’t it?