How to answer “what do you do?” on a pathless path

I was at a gathering on Thursday and someone asked, “What do you do?”

Given that I was in Austin, I thought I could share the real story: “writing online, podcasting, internet things, you know.” It was a creator’s hangout after all.

“What do you write about?” he followed up.

Ah nice, he’s interested.

“I write about our relationship with work and how common knowledge of work’s role in our lives seems to be shifting.

The guy, still skeptical, looked at me and said, “Is there really anything more to say about that?”

Brutal.

But, I’ve had many of these kinds of conversations over the years. I misread him as someone who wanted to hear more. He wasn’t, so I moved on, made a joke, and shifted the conversation away from my work.

This doesn’t frustrate me at all. I write about something very niche and most people are simply not interested. I also work and live in an unconventional way, one that often makes people uncomfortable. I love what I’m doing but genuinely don’t want to convert people.

The world demands a story of what the hell you are up to

Deep down many of us wish we could say “fuck it” and do bold things in our life without having to explain ourselves.

But that’s not how the world works.

When you do things that are not common, people ask questions, and to answer those questions you need a response.

When you are working full-time you have a story called a job. A job is the most accepted story of adulthood. Even if you hate that job or it’s a job working for a sketchy company, no one cares that much. It is a passable story.

But on a pathless path, you will struggle ever fully to explain what you are up to.

This is most challenging at first when your uncertainty and confusion are off the charts and your desire to make up a story (for others and yourself) that you know what you are doing is high.

You need three stories

The three stories are:

  1. A boomer-compatible story
  2. A curiosity trigger story
  3. The real story

A “boomer-compatible story is necessary for people who just want to know how you fit into the world of work

The first one is for those anchored to a traditional view of work or for someone you simply don’t want to defend your path to.

Despite this, you need some answer that isn’t dismissive. It should be directionally true but does not need to be true in your heart.

An example could be, “I am doing some part-time work and looking for my next job.” While you may not be actively looking for a job, you theoretically might consider one if someone offered you a million dollars.

Another example could be, “I’m trying to build a business” instead of the more accurate “I’m dabbling with podcasting, writing online, and trying to post my way to Twitter fame.”

The key thing with a “boomer compatible” story is that you are trying to share something neutral. You don’t want to appear as if you are making a moral judgment about the other person’s chosen path or preferred working arrangements.

The other thing to avoid sharing is your inherent uncertainty. While it may be “true” that you don’t know what you are doing, this can trigger the hell out of people. They will experience it as their fear and insecurity: “What do you mean you don’t know how you’re going to make money six months from now!? Can’t you just get a job?”

This is hard because of course, you want to feel seen. You need support. But this is not the group to seek it out from.

Not all boomers either, of course. Some boomers rock. And you’ll find people of all ages, gender and background questioning your journey.

The key with this group is to keep it neutral and pivot to other topics ASAP.

Next, you want a story that is a little more “you” and has some “curiosity triggers” if people want to go deeper.

This is essentially what I did in that creator meetup. I was sharing some buzzwords that might make someone curious. Podcasting, writing online, etc…

This is perfect for a somewhat friendly crowd but with people who you don’t know quite well.

You want a balance of a “normal” answer and one that is a little weirder.

Something like, “I just left my job but am excited to explore mindfulness and breathwork.”

A small number of people might respond with “Oh wow, you should meet my friend, Jonny,” or offer other pieces of helpful advice. Others may ignore it completely. Cool. Move on to other topics.

This kind of story is better for people who might be more accepting of people following unconventional paths, or people who are known to be helpful and curious.

But they, like most people, usually still demand a story.

Finally, the REAL story for your fellow weirdos

The third story is for your fellow travelers. These people, god bless them, want to know everything and actually are curious about what you are up to. Many of them are on very similar paths and just want to learn from you to improve their own approach. For these kinds of people, I personally say something like “I’m doing a bunch of stuff; writing, podcasting, online courses, consulting, and different ways of working and living” From there I answer whatever questions people have. These conversations can be fun and they push me to think more deeply about what I’m up to and offer useful advice.

You Should A/B Test And Pay Attention

You should always be changing these stories and noticing what happens. This has two benefits. You can see how you feel and you can also see if others think you are crazy or on the right path.

From your perspective, does it make you feel excited? Does it make you want to run away? Do you feel ashamed describing what you are up to?

Similarly, you should watch and notice how others react to your stories. Watch their faces. Do their eyes light up with curiosity? If so, why? By asking them questions you can learn more about your own path.

When you first leave a conventional path, describing yourself is one of the hardest things. This is mostly because you’ve likely traded a path with a certain future for a path with an uncertain one and you don’t know what you are up to by design.

Things like sabbaticals and taking breaks from work are becoming more accepted.

But for now, we still need stories.

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.

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