Should I take that job? Ten questions.

I’ve recently had a few conversations with people wrestling with a decision on whether to take a particular job. Here’s my list of ten questions you should ask yourself.

Hovering over all of this are two words that might seem a little morbid.

Memento Mori. Remember that you will die.

I first learned this reading Ryan Holiday’s works, especially The Obstacle is the Way, which re-introduced me to Marcus Aurelius and his Meditations. Great life reading. Anyway, it’s not morbid, it’s liberating. It means, do what matters and do what is important. And don’t waste time on the crap.

OK, the 10 questions. If all these are a ‘yes’, the job is a keeper. If not, keep looking. Life is too short for bad jobs. (look, I get families need to be supported, people have obligations, and sometimes you just need the job and the money. But don’t settle!).

1. Does the company & opportunity have a Mission?

If they have no discernible mission, or don’t tell you about it during the interview process, it’s just a job. Keep looking.

2. Are you passionate about that Mission – does it matter? mean something to you?

Life is too short to spend on jobs that don’t matter.

3. Will I learn new things in this job?

If you’re not learning, you’re not growing. If you’re not growing, you’re stagnant. And who wants that?

4. Is there a specific person I believe I can learn from?

Ideally, it will be the person that you report to – but it doesn’t have to be. Just someone you’ll have access to on a regular basis.

5. Are there people I can teach? Do I have something to give?

This is more important as your career progresses, but learning and teaching should be hand-and-glove – you should be doing both. Your satisfaction will double if you know you are making other team members better.

6. Am I doing something new, from previous roles?

This has always been a hard and fast rule for me. The next job has to have something different. A new domain, different levels of responsibility, a different functional area. Otherwise, you won’t be learning much.

7. Is this company going to be around, or am I OK if they are not? 

Figure out if the company is going to work (a startup requires a different set of questions than a big company). You’re investing a good chunk of your life in it.

Are they in an industry that’s growing? Do they have something different going for them compared to their competition? Does the company have its shit together? (Note: the interview process is a good 1st test for having their shit together – if the interview process is confused, drawn out, mismanaged, indecisive, opaque, etc. – they’ll be that way after you join too…). And if you’re not sure the company is gonna make it in the long run, but everything else looks good, then go in with your eyes open and take the gamble!

8. Do I care enough about these people, this work domain, this company, to spend 5 years of my life on it?

Life’s too short to spend on things you don’t care about, or to work with assholes. Even if the pay is good. Is the chemistry good with the people you met? Will you be excited to work with them every day? You’re going to see them more than your family! Find a good fit.

9. How many “at bats” do you have?

We all only have so many jobs to take in our life. To borrow baseball language, I call these “at bats”. How many “at bats” do you have left? When I was 50, I thought, well, I have maybe 2 or 3 more jobs left – I’m not going to waste an at bat on something that doesn’t feel quite right. When you’re 22, you have more time, and more at bats to take a flyer on.

10. How does this set me up for my next job?

When I am done with this job, what will I have learned and how can that advance my career the next time? Will it open doors for bigger roles? New industries? Maybe starting my own company? Have some idea where you want to go in your life and career, and try to take jobs that help you get ready for that. (in my list of work rules, this is #16).

OK. You got through all those questions, and the answers were all solid. You’ll notice none of the questions were about money. Not an accident. It’s not because money isn’t important – it’s because you shouldn’t start there. Figure all the other stuff out, and if you’re passionate about the role, the money will figure itself out. Just remember, “you don’t get what you don’t ask for“. If you don’t like the offer, tell them you love the opportunity but you need the compensation to make sense.

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