Don’t Start a Job Search Without Answering This One Question

I love when people quit their jobs. Ok, that’s probably a bit strong. Let me clarify. I love when people leave a job because they’ve made an impact and want new challenges; or feel they could be accomplishing a greater number their goals somewhere else. But when these folks approach me for advice as to what to do next, there’s one question most haven’t asked themselves. And it’s a critical question. I don’t know how you decide without answering it first.

The question is, What Are You Optimizing For?

Now let me caveat that this question is most important when you’re deciding between several good opportunities. In a tough economy there are many who feel lucky to hold on to the job they have, and those making a transition might not have the luxury to hold out for the “perfect gig” or even be able to find a new one easily.

The most successful folks are rarely trying to decide between a good option and a bad option when it comes to employment. This is especially true in today’s technology sector where it’s not uncommon for skilled engineers to have almost daily inbound interest from recruiters, founders and former colleagues. Choosing between a good option and a bad one is easy – don’t do the bad one. However when you’ve got multiple intriguing roles available to you it’s not a question of good vs bad or right vs wrong. It’s a question of which one is best for you in this next phase of your career. And to do that you need to decide what to optimize for.

When you are clear on your prioritization, the resulting framework can cut through the noise. I find it helpful to narrow down to 2-3 attributes of how you’d describe the “perfect job” for you at this moment. What are some things you can choose to optimize for? Well the list is near endless so you can start by just naming all the characteristics important to you. Examples could include: nearterm compensation, longterm compensation, commute time, quality of colleagues, brand reputation, title, geographic location, flexibility of schedule, quality of manager, health benefits, and so on.

Next is the hard part – the narrowing. You need to be firm and clear. These decisions aren’t indelible but you’re trying to end up with a job that will meet your goals for at least 2-3 years, so be thoughtful and honest with yourself. Once that’s done, start force ranking or any other assignment of relative value for each attribute to the job opportunities you’re currently considering. At the end of this process you should have one or two ideas that rise above the others. Those are what you should pursue the hardest. If it doesn’t feel right then you’ve either misjudged what you want to optimize for or gotten your rankings wrong. Revisit.

Post-job change you can check back in every six months or so to assess whether you were correct in your assessment of the job you took and whether your optimization has shifted based upon your own evolution, life events, and so on.

This process helped me ultimately make the decision to leave Google and start my seed stage venture firm Homebrew. Prior to being honest with myself about what I was going to optimize for, everything I considered doing next was just a list of pros and cons, and it was difficult to turn that into conviction. With this process I let some other good opportunities drop away because I knew they weren’t right. And Homebrew was so clearly what I wanted to work on.

Good luck in any current or future career search!

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