Every career change needs to set up the next one, writes Ken Goldstein.

Few people these days seem to have a lot of choices to make about job opportunities. With national unemployment stuck above 9% for the past 26 months, those who have jobs are largely counting their blessings, and those who don’t are spending most of their waking moments trying to get anything at all, hoping to stay in a field relevant to their expertise and not drain their savings. We all hear the stories of people’s sorrow, hardship, and demoralization. The impact is daunting, and those you meet fighting to pursue their passions and remain financially independent deserve our most sincere empathy. If you have the chance to offer support to a friend or networked acquaintance, do it. Even if all you can do is lend an ear, you may be surprised just how much that outreach is valued and appreciated.

This past week I had the opportunity to lend an ear on a different tangent, helping advise a bright young rising executive on his next career move. I enjoy being able to mentor those whose careers I have watched evolve from anywhere from one to twenty years, and although the last thing in the world I ever want to do (or will do) is tell someone what to do, I do like to put very difficult and often uncomfortable questions in front of people for them to answer, hoping that the thought process leads them to their own answers. My sense is, the better the questions, the better chance you have at improved answers, and anyone who knows me knows that I love to ask questions.

I didn’t know this fellow extremely well, but I had the good fortune of observing his broad range of skills. He called me up and wanted me to help him decide if he should leave his current position and take another offer. Simple enough, right? You have this package and set of circumstances, and the other company is offering that package and set of circumstances. Compare and contrast, make a decision, stay in place or move on. Well, if that’s your framework for making a career decision, I am certainly the wrong person to ask for coaching. First, you don’t need someone else to help you with that framework, you can do that math in your head all by yourself. Second, I would never use that framework, to me it’s a path to an almost certain dead-end.

Don’t like ads? Become a supporter and enjoy The Good Men Project ad free

Where I begin the process of deciding if you should make a move is with a very simple metaphor: have you ever played pool? If you haven’t, have you ever watched a pro run the table? And if you haven’t, check out Jackie Gleason and Paul Newman in the original 1961 version of The Hustler. But I digress. What you observe in the difference between amateur and professional pool is how the table is run. Amateurs look for the best shot on the table and sink that ball. Pros only take a shot when it lines up their next shot, so after a ball has dropped, there is another ball ready to drop, then another, then another, letting them run the table and only then sink the eight ball. A shot is only good if it sets up the next shot. Period.

That’s the framework I suggest for anyone trying to make a tough career decision: each move has to set up the next move, even if you don’t know where the balls are going to stop moving—which you never will, because our lives are governed by market forces and luck as much as they are our own determination (that’s a lesson humility teaches us). The job and package you have is a known. The package being offered is a known, the job not so much because you haven’t done it yet. What is unknown is where and when you will be at the end of the next job if you take it, and the one after that, and the one after that. Those can never be known, unless you can see the future, in which case you don’t need to have lunch with me.

To have a chance at getting the right decision, you’re going to need to answer three extremely personal questions. Sorry.

The first question I asked this fellow was quite simple: to what do you aspire? If you could see the future, five years out, ten years out, what do you think you want those illusive opportunities in your target sights to be? Force yourself to focus on that, think about what you want downstream. It may never happen and you may change your mind a dozen or more times between now and then, that’s fine and natural. Still, ask yourself right now, what is the downstream job you want?

Now the second question: why can’t you have that job right now? It’s a trick question, you can’t have it because it isn’t being offered, but the real question is what skills and experience don’t you have right now that would let you step into that job? You know what experience and knowledge you have today. What don’t you know or haven’t you learned to make you qualified for that opportunity? You must answer this honestly and specifically.

Now you’re ready for the third and most important question: what knowledge and experience do you need to acquire in your next opportunity to most closely qualify you for the opportunity beyond it? You know the present, you have an inkling of what you think you want the future to look like. How do you close the gap between the present and the future? What do you really want out of your next job to set you up for the job beyond it, or set you up for the best chance at the desired job beyond it, or set you up for the best and broadest set of potential choice opportunities for the job beyond it?

To me, that is how you decide if the next gig you are being offered is the right gig for you. Don’t take the shot unless it sets up another shot. More money is nice, more responsibility is nice, an expense account is nice, a beautiful office is nice. All of those things are very, very nice. And all of those things are fleeting. They can disappear in a nanosecond. When they are gone, what will you have? The only thing you will have is your experience — what you have learned is what you can take with you. Nothing more, including salary history. What you can do next is a combination of your track record, your integrity (= your reputation), and the probability that what you have learned will be of value to your next set of challenges.

At the end of our lunch, the fellow whom I assaulted with these questions made an interesting decision. He was neither going to stay in his current job nor take the new offer on the table. He was going to revisit an offer that had been made to him a few months earlier that he had rejected. He realized he had rejected it for the wrong reasons. He rejected it for the package and relocation requirement. When he thought about the opportunity downstream that he really wanted and the gap he needed to fill to be ready for that, the offer he rejected appeared to him to be the perfect fit. He left the lunch hungry to see if that gig would still be there, and if not, how he could actively find one more like it. He was 100% focused on filling the learning gap, that was his new criteria. That felt pretty spot on to me, and it will be interesting to see where he goes from here. I have a pretty good idea that he and I will be talking again in about five years.

Don’t like ads? Become a supporter and enjoy The Good Men Project ad free

Oh, one more thing. If you are going to be a manager and have never had a good boss, get one. The odds are terribly against this, as you know from your history. The reason most employees complain about their bosses is because their bosses aren’t good bosses, and the reason their bosses aren’t good bosses is because they never had a really good boss. There is no way you can learn to be a good boss if you haven’t experienced one, been mentored by one, and drained them dry of all they know. If this is part of the package, value it over cash big time. Most people don’t quit jobs, they quit bosses. The value of someone who cares about you and will help you become your best cannot be quantified.

—Photo Tim Green aka atoach/Flickr