Questions to Ask Instead of “What Are You Doing With Your Life?”

Last week I talked about the dreaded question young adults (and people in general) face all too often:

“So what are you doing now?”

I explained that many of us hate that question because it evokes feelings of shame and fear that we’re not “enough.”

Today I’m here to present some alternatives: things you can ask people without causing them to feel vastly inferior, enter into panic mode, or run for the hills. 😊

I’m a naturally anxious person, so admittedly pretty much any question can leave me scrambling for an answer as my mind goes totally blank. (What am I doing? Am I doing anything? I’m sure I am…what did I just finish doing?!)

But the questions below aren’t as loaded as “So what are you doing now?” or its cousin, “So what are you doing with your life?”

Questions to Ask Instead of "What Are You Doing With Your Life?" or "What Are You Doing Now?" | Millennials with Meaning


Here are some options that are a bit less daunting and not so career-focused:

  • “So what’s new?” This casual, open-ended conversation starter allows us to steer our response in a direction we’re comfortable with, emphasizing the things we’re excited to talk about while spending less time on subjects we aren’t as thrilled about. We might talk more about our families than our jobs (or vice-versa) or work our way up to the more difficult topics as the conversation progresses.
  • “So what have you been up to lately?” We know you’re asking how we fill our schedules and most of us probably spend the majority of our time at a job. But phrasing it this way takes off some of the pressure to say what sounds good (i.e. an impressive job title) and gives us more freedom to tell it like it really is.
  • “So what all has happened since the last time I saw you?” Whether it’s been a week or a decade, we know the main plot points better than anyone. We’ll touch on all the important things!
  • “So do you see yourself staying in this area/field/city?” This could apply to relationships too: “Do you see the two of you heading toward marriage?”
  • “So if you could live anywhere in the world, where would you live?” This could get us to start dreaming out loud, and you’ll probably learn more about us this way than in any formal inquisition.


Then there are the more career-minded questions that you might ask new graduates, those who are trying to decide on a career/new career, or those who may need a little guidance:

  • “So what’s your dream job?” We might very well reply that we don’t know, but if you’re trying to help, you can press us with further questions like:
    • “If you could get paid to do anything, what would you do?”
    • “What would you do even if you didn’t get paid for it?”
    • “Do you prefer to work with people or from home?”
    • “What time of day are you most energized? Are you more of an early bird or a night owl?”
    • “What did you dream of becoming as a kid?”
  • “So what did you major in?” Or “So what classes did you take?” This is an easy way to get a feel for what we studied in college and possibly more insight on whether or not we actually enjoyed it.
  • “So what made you choose the degree that you did?” We might not have had great reasons, but we’ll probably give you an honest answer and a glimpse at our thought process.
  • “So would you ever follow in your mom’s/dad’s/grandparent’s/whomever’s footsteps and go into _____________?” If you think we’d be great at a specific job that a mutual acquaintance has, it can’t hurt to tell us you see potential there! Just try not to add to the pressure we may already be feeling from others. We millennials aren’t always sensitive little babies, but we don’t want to feel like we’re letting you down with the truth, either. 😊
  • “So what did you do in your free time when you were at/lived in [college name or former place of residence]?” School itself or a job itself may not get us excited, but you might start to hear more passion in our voices when we talk about hobbies or other interests.

Notice a pattern here? These questions are all pretty conversational. They aren’t so vocation-oriented. If you keep your questions relaxed, you can help alleviate any fears as your subjects realize you’re really on their side and want the best for them…not just an opportunity to brag or compare.

Because I’m someone who gets easily intimidated, I try to pose questions to others in the way that would put me most at ease, and I’ve found it usually works pretty well.

These are obviously just suggestions – each person is unique and while some of us may prefer a less aggressive line of questioning, I’m sure there are others who’d disagree! I can only speak for myself and those I know, but I’ve definitely noticed a recurring theme of shame and fear among many of us when it comes to the “What are you doing with your life?” questions that are typically asked.

My biggest tip? Just be genuinely caring and do your best to show that you’re there for support, not to pile on more pressure.

We all need support. Advice. Guidance. Affirmation. Most of all, we just need to hear once in a while that someone believes in us…because some days we don’t believe in ourselves.

Whether you’re a millennial or not, what questions do you suggest as alternatives to the standard “So what are you doing with your life?” Do you prefer the more low-pressure alternatives or something else altogether?

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There are 2 comments

  1. Curious reader

    I have asked, “so what’s new?,” many times. If I know the person well, I will try to personalize my approach by asking questions that are related to what I know the person values, e.g., hobbies, family, faith, entertainment. Some people do like to talk about their vocational occupations, however, that isn’t usually the primary topic millennials what to discuss. For people I casually know, but I don’t know what they value, I might ask “how is your summer?” or “what do you enjoy doing during the summer?”

    I think many people (including me) are anxious about talking about their “progress” in life. Life is difficult, but I admire and respect people who are genuine and authentic about their lives. They are almost always the most kind, generous, forgiving, and loving people I know.

    1. millennialswithmeaning

      Great ideas! Asking someone about their summer is perfect for those who aren’t close friends. It can be so hard to know what to say in those situations!

      I, too, really appreciate people who are willing to be authentic. By being honest about their own struggles, they free others to live the same way and that is so refreshing! And it seems so much easier to talk about my own shortcomings when someone else is admitting theirs, too. 🙂

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