Daily Endeavor Blog

How many times have you heard the question “What do you want to do?” More often than not the person asking wants to help. It seems a friendly enough question: it’s an expression of interest in the other person, it’s asking vs. assuming, it’s forward looking, it’s an invitation to talk more.

So why do so many people fill with dread when they’re asked? My opinion: it’s nearly impossible to answer. It’s not as impossible as the utopian “What do you see yourself doing in 20 years?” but it’s well on its way.

For many, the question they hear is: “What’s the one thing you want to do?” or “What do you want to do with your life?” You mean, the rest of my life? It’s an awkward position to be put in. You either need to skirt around the truth by stating there’s only one conceivable thing you want to do for the next 70 years which may put a big dent in your credibility, or if you don’t know, then you look shallow, unprepared, or even weak by not having a genuine answer to such an important personal question.

Awkward. It’s possible the person is trying to test you, but most often it’s someone trying to be friendly, someone who really wants to see you find it, whatever it is. In fact that someone may be you, asking yourself for the umpteenth time.

Ask a different question. The direction is right, but the framing is wrong. Instead of going for certainty, lower the bar a bit.

What do you think you want to do?

This seemingly small change acknowledges you’re a warm-blooded person with multiple (if not disparate and conflicting) interests, and gives you space to be intrigued by something, but not wed to it.

Then put the drop on the forever thing. Move the horizon to something much closer that you can actually picture and act on. Two years out is about as far as I can picture, and truthfully it’s already pretty blurry by that point. Continuing to re-frame, it looks like:

Over the next two years, what do you think you want to do?

For getting stuff done, two weeks is a much better period to have a clear line-of-sight. The problem with two weeks though is it’s hard to do anything that really stretches you; it’s a tactical block of time. If you’re thinking about a full-time role as the next step in your work life, a two year horizon gives you enough room to start to think big and has the benefit of being a period of time that hiring firms know how to speak.

Sometimes though, even this question is still too open-ended to be able to answer. The canvas can feel too blank. The implied question can still often be “What job do you want to do?” You and I both know life is so much bigger than a job. I find It’s easier to answer a question about an idea, an interest, a way of doing things, or a result. In other words, think about what else you’d like to include in your growing reputation.

Over the next two years, what do you want to be better known for?

Now that’s a question you can sink your teeth into. For example:

• I’d like to be better known for my real estate deal analysis prowess
• I’d like to be better known for my open source code
• I’d like to be better known for my growing microfinance expertise
• I’d like to be better known for closing big sales
• I’d like to be better known for describing our cleantech future
• I’d like to be better known for enabling local eyewitness reporting to flourish

This form of the question is not a 100% solution; it’s simply one step along the way. Nonetheless, I’ve found working with folks that it’s a good way to break the logjam of beginning to think about what next. What do you think?