Jobs provide a ready-to-inhabit psychological home-away-from-home that a mere portfolio of gigs does not. Home, sweet office, as a refuge from home, sweet home. In a good political and economic environment, this is not very important. If your gigs are enough fun, and the local Starbucks or other “third place” is open, you might not even notice that you lack a psychological home for work. Not everybody is a homebody at work, or wants to be.

But when the economy and political environment go bad, being in the gig economy is like being caught outdoors in the middle of a winter storm. Then you notice. Suddenly, being indoors in a nice job offering home comforts seems really attractive. It’s not even really about the money. It is about having an intact social reality to inhabit.

I’ve been trying to come to terms with this sense of being caught outdoors in bad political-economic weather. I made myself this little iPad painting to contemplate.

I’ll explain the picture in a minute, but some more general thoughts first.

Gig Economy Weather

Under normal conditions, when the economy and political environment are healthy, being in the gig economy is like being outdoors in a park in nice weather, with a picnic basket, and a clean bathroom nearby. The sun is shining, squirrels are running around. Birds are chirping. You don’t miss home, and in the moment, it seems like being outdoors is an obviously nicer situation than being cooped up indoors, at least for you.

Interactions with clients feel like they are happening across a window ledge: they are indoors, you are outdoors. You’re both happy with your choices. Indoors or outdoors is a matter of lifestyle tastes.

When the political and economic environment are really nice, you even get a whiff of a yearning for the outdoors from clients (I got this feeling sometimes in 2013-15). They are mildly envious of your freedoms. There they are, trapped indoors within the limited reality of a single organization, while you are free to participate in many realities in many organizations, and also to enjoy the broader economic outdoors with personal projects, writing about larger macro trends, and so on. That’s what good times in the gig economy feel like.

These are not good times. Lately, I’ll admit, in meetings with clients, I’ve found myself feeling mildly envious that they are indoors, within largely intact private social realities, while I’m outdoors in the midst of an unraveling public reality, facing the full fury of the politico-economic elements without a roof and walls around my work.

Dulce Domum

We are so used to thinking in terms of the work-vs-home dichotomy that we often lose sight of the fact that work is in fact a home-away-from-home. In a job, it almost always is literally so. You have a desk, or even a room to yourself, with access to kitchen facilities, bathrooms, and a bunch of people you probably like — your work “family” so to speak. If you work for a particularly paternalistic company like Google, there might even be good food, places to nap, a game room, and laundry. It might even be better than home.

In the gig economy, this home-like feeling may or may not exist. Perhaps you have a coworking space and regular lunch buddies. Perhaps the friendly Starbucks barista substitutes for the friendly coworker; someone you say hi to every day.

This feeling of being home-at-work (HAW) is important. More so than work-from-home (WFH). It allows us to relax, and trust the work environment to supply a certain amount of both material and social comfort. It provides a thoughtfully mediated sense of connection to the broader world. It fosters a productive and generative state of mind.

This is the sweet-home feeling, dulce domum. For work, perhaps we should call it dulce officium, the sweet-office feeling (my Latin translation might be off, but I’m sticking to it since I like the sound of the phrase).

What is this feeling like?

In Kenneth Grahame’s classic, The Wind in the Willows, there is a moving chapter titled Dulce Domum, where the two main protagonists, Mole and Rat, are making their way back from yet another crazy adventure on a cold winter night. They pass through a village with many people comfortably ensconced in their warm homes:

But it was from one little window, with its blind drawn down, a mere blank transparency on the night, that the sense of home and the little curtained world within walls—the larger stressful world of outside Nature shut out and forgotten—most pulsated…

Then a gust of bitter wind took them in the back of the neck, a small sting of frozen sleet on the skin woke them as from a dream, and they knew their toes to be cold and their legs tired, and their own home distant a weary way.

Thus primed to yearn for home, as they exit the village, Mole catches a whiff of his own home nearby, which he’d abandoned several months earlier, disgusted with chores and cleaning, to go adventuring. He is overcome by a powerful homesickness, and is inconsolable until the two of them find their way back to his home and spend some time there.

If The Wind in the Willows were a story about the gig economy, the village would be a business district full of offices full of people happy to be away from home, and the adventures of Mole would be gigs. The dulce officium moment would be a sudden yearning for a regular job, with lunch buddies, malfunctioning printers, and running gripes about bad coffee.

I occasionally get a whiff of that feeling now, when I peek into the lives of paycheck people, through client meetings or otherwise. They are secure in their warm jobs, inside organizations with their inner social realities largely intact, even if the material realities of work-from-home regimes have made the home-at-work feeling much messier.

For people with secure paycheck jobs, the reality of Covid19 has not yet fully hit, and possibly never will, no matter how long they work from home.

They are able to immerse themselves in the pleasant reality distortion fields of their jobs, within which the pandemic has been aestheticized and processed into a business crisis, complete with recovery strategy meetings. Hardship is of a familiar corporate sort — budgets cut, pay cuts, travel and events canceled.

Organizations do these things in the face of every crisis, so there is a certain ritual familiarity with the response pattern, if not the stressor. Paycheck employees are at home in their responses. Dulce officium.

You’re Exposed

Dulce officium is not the case for the gig economy. The much flimsier work-homes we construct for ourselves, out of a favorite table at Starbucks, lunches with friends, and occasional meetups, have fallen apart.

Even if your cash flow and gig work routines haven’t been impacted — mine largely haven’t — the overall sense of being home at work has evaporated. I definitely feel exposed and outdoors. So should you. In the gig economy right now, any sense of security is a false one, unless your talents naturally turn towards profiteering off black-market PPE supplies or something.

The main reason, of course, is that if you’re in the gig economy, strategizing the recovery is not an optional spectator sport for you, consisting largely of tracking what the CEO is doing. It is an unavoidable imperative, fraught with real risk.

You literally have to think for yourself right now, because it is nobody else’s job to do so. If you don’t, things could go really badly for you. Already, almost by instinct (which is a result of nine years of experience), I’ve made several quick, tactical moves that turned out to be really wise. I’d already be in trouble if I hadn’t thought of them, and moved very quickly to do them. Like the rest of you indies, I have no paternalistic organization prompting me to do the necessary thinking and acting, and no concerned manager asking after my welfare. So this is not idle speculation.

This political-economic environment really is dangerous.

You really are exposed.

Lack of tactical and strategic foresight will cost you.

Newbies have to be extra careful — lack of experience navigating uncertainty increases your chances of making bad errors.

For an employee in a stable organization, there may be some tough times, but trusting the leadership to do a good job navigating the crisis might actually be a reasonable option. If you think your employer will be among those that will crash and burn through the crisis, but you have solid marketable skills in job-like domains, you might still be able to avoid strategizing the recovery for yourself. You could simply look for a new job with an organization that seems set to recover strong.

Of course, this is also an option for some in the gig economy. I’ve already heard of several giving up and heading indoors to jobs. But for many, it is either not an option (you might have marketable skills, but just not in a job-shaped package), or you don’t want to. A little bit of both apply to me. My skills don’t fit jobs, and a part of me is convinced that “whatever doesn’t kill me makes me stronger” in this environment.

If I can make it through this thing, I can probably make it through almost anything. So despite the unpleasant political-economic weather, the challenge appeals to me.

A Mood Map of the Future

Let’s talk about the picture at the top. It’s a mood map of the future.

There’s of course a lot of very specific forecasting, mapping, and maneuvering you can and should do relating to how your particular corner of the gig economy is responding to the crisis. But underneath those practical tasks, there is a more important emotional self-regulation task you have to tackle: dealing with the feeling of being outdoors in a harsh environment, without an economic “home” to work out of.

You have to assess the general mood, your own mood, assess whether the fit is a positive one that lends you agency, or whether you need to work on your own mood (since you can’t affect the general mood outside of a small, local zone).

This is not an environment that will be kind to depressed listlessness and weak motivation.

I’ve tried to map the general mood in the picture above.

To the left of the 2020 vertical line, there is a diffuse but defined mood. It is a patchwork of red, yellow, and green (which signify what you think they signify). Against this backdrop, the futures of individual organizations are evolving, with much stronger internal reality-distortion field moods created by things going well or poorly. Each forking tube is a reality distortion field evolving in time.

To the right of the 2020 vertical line, the mood is not so much good or bad as it is undefined. Like in those movies set in simulated worlds where the character runs to the edge of the simulation and discovers an empty grid. It’s not good or bad. It just isn’t.

The future we thought we were inhabiting has been trashed. The future that we are creating right now is largely undefined, still very much under construction.

There’s a few defined red, orange, and yellow patches, but not much green. But mostly it’s empty grid space.

There is enormous opportunity in this lack of definition of course. It means the future is waiting to be invented, and as a free agent, you have more ability than most to participate in that invention. But there is also enormous risk and anomie in that lack of definition. That grid-like outdoors is a stark space, bereft of that lovely home-at-work feeling that normally keeps you going. No dulce officium there.

If you’re outdoors in this gig economy, this is your element. An undefined grid with patches of danger, and very little by way of soul-nourishing at-home comfort. You can peek in through Zoom windows at people enjoying such comforts, like Mole and Rat in The Wind in the Willows, but you’re not one of them.

Don’t let their sense of security contaminate your mood. They can afford it, you cannot. You need to maintain a much higher degree of alertness.

If you’re indoors, there’s a good chance (to the tune of 60% of businesses in California according to a news report I just watched) you’re with a stable employer, whose inner reality can actually withstand the collapse of the outdoor grand narrative, at least for a while.

Of course, if your employer was already in bad shape, there is a good chance it’s on the verge of crashing and burning.

The green-turning-red thin line outside of the corporate “reality tunnels” is a typical free agent trajectory in this environment. The green and red lines inside the tunnels are the trajectories of paycheck employees in organizations that are surviving versus failing respectively.

You’ll notice I’ve illustrated a fork in the futures of the 3 surviving organization. If an organization isn’t being killed by immediate existential threats, it is at least facing a range of possible futures. Some have a narrow range, some have a wide range.

The point of this map is not to make specific predictions, gesture at specific environmental realities, or suggest specific maneuvers and strategies. The point is to become sensitized to the mood of the environment, your own mood within it, and how it relates to the distribution of environmental risks and opportunities.

Specific predictions can go wildly wrong. Maps can be inaccurate. Maneuvers may fail. But the mood of the party is generally unmistakeable, and the mood you bring to the party is the biggest determinant of whether you weather the storm, whether it drives you indoors, or whether it destroys you.

So for the time being, there’s no dulce officium for you. Just a challenge to survive and thrive outdoors in bad weather.

Newbie indie consultants tend to have a LOT of questions on their mind. Most of these are bad questions because there are no great or terrible answers to them at the newbie stage of the game. The good-enough answers, on the other hand, are obvious and not worth overthinking.

The problem is, newbies pay so much attention to the bad questions, they often forget to look for the good questions that can actually pay huge dividends if asked early enough. So how do you avoid getting sucked into the black hole of bad questions while looking for the good ones?

The key is to think like an actor rather than a model.

Bad Questions

Here are some examples of bad questions.

• LLC or S-corp? (or equivalent question in other countries). The right answer is “probably LLC,” but if you don’t trust me, sure, go with S-corp. It’s not too costly to fix this if you get this wrong.

• Blogging to attract inbound leads, or proactive email pitches? The obvious answer is the right one: try both, see what works, double down. Cheap effort.

• Targeted, researched pitches versus spray-and-pray? Targeted, obviously. But sure, waste your time on spray-and-pray for a while. Maybe you’re one of the exceptions.

The only reason to waste a lot of time on these questions is that you don’t actually feel ready to get going with serious trial-and-error for whatever reason.

Bad newbie questions are not bad because they aren’t worth asking at all. They’re definitely worth say 15 minutes of fairly mediocre mental effort and googling to get to good-enough starter answers. So what makes them bad?

• They’re bad questions because they can trap you into endless analysis-paralysis and hold you back from actually trying things.

• They’re bad questions because you’re trying to fix an information deficit (which calls for trial and error) by over-analyzing information you do have.

• They’re bad questions because they are read-fire-aim or ready-fire-steer questions that you’re posing in ready-aim-fire ways.

• And most importantly: they are bad questions because they distract you from looking for the good questions to ask.

Unfortunately, the few good questions worth asking early on tend to not be asked.

These are not questions mentors or advisors can just formulate for you to ask, because they tend to be highly situation-specific. They are the good questions for you to ask.

So how do you quickly get past the 100 bad questions everybody asks, while making sure you spend serious time on the 4-5 questions that are good for you to ask, that nobody can tell you how to ask?

I have a meta-question that you should ask about every question that occurs to you:

Is this a model question or an actor question?

I need to detour through a discussion of actors vs. models before I can explain how to ask the meta-question.

Models versus Actors

Modeling and acting are both gig-economy professions. Both have a bit more structure than most gig-economy careers. In particular, there exist agents and audition processes for both. Neither is a plug-and-play under-the-API gig economy career like rideshare-driving though. You need talent, aptitude, some training, an element of luck, and a decent amount of mindful strategizing to succeed at either.

But despite their similarity, there is one crucial difference between them.

Modeling is a career based on looking like other models. Acting is a career based on looking different from other actors.

This is not a subtle point. Modeling is a high-end commodity labor market, acting is a differentiated labor market.

The difference is right there on your TV screen.

Actors tend to be recognizable and imitable (their style is unique enough to allow for recognizable impressions and caricatures). They try hard to make a unique impression and create a memorable new idea in the viewers’ head. Benedict Cumberbatch, for instance, changed everybody’s ideas about what Sherlock Holmes could look like.

Models, on the other hand, tend to be interchangeable and unmemorable. They either embody a particular standard of beauty really well (like ramp models), or a particular societal role like “mom” or “office worker” really well (ordinary commercials). They try hard to conform to an idea the viewer already has in their heads. You can’t impersonate or caricature a model, only the broader category that they exemplify well.

Of course there is a fuzzy area of overlap and crossover. Flo, the character in Progressive Insurance ads in the United States, is really more actor than model, and the campaign has been developed more like a television show than an ad campaign.

And of course, there are plenty of B-movies that feature very forgettable model-like actors.

And then there are exceptions like Daniel Craig (James Bond) and Stana Katic (Kate Beckett in Castle) who crossed over from modeling to acting successfully (it’s hard to go the other way, since successful actors by definition are too recognizable to “work” in most ads).

But the basic distinction is a solid one.

The distinction has only a very weak correlation with fame. Actors versus models is a distinction observable both in newbies and famous examples of both.

There’s a game I play with my wife we call “I’ve seen him/her in something else” that is especially fun with obscure actors who have bit roles in lots of shows and movies. Something about them “pops” in a way that transcends the context of a particular story. I’m pretty good at this game, and I usually figure out where I’ve seen an actor before my wife does.

But the game doesn’t work well with models!

This was driven home for me in a very powerful way recently. Walking around downtown LA a few months back, I walked past a photoshoot in progress (a frequent thing around here). The model looked very familiar, but I couldn’t immediately place her.

It took me a couple of minutes before it hit me: it was Cindy Crawford. Only the most famous model of the 80s (as well as star of a few B-movies). Can you imagine that delayed recognition happening with say Meryl Streep, Samuel L. Jackson, or Jack Nicholson?

The takeaway is this: even the most obscure actor tends to pop recognizably from their context, but even the most famous model tends to blend into their context.

Two Kinds of Questions

Now here’s the thing: for almost all of you, the good questions are going to be actor questions, and the bad questions are going to be model questions.

At the same time, 9 out of 10 questions that occur to you to ask are going to be model questions. So your meta-process should be: quickly get to good-enough on the “model” questions, while keeping your eyes open for your unique version of the true “actor” questions.

The reason is simple: even though there are a lot more “modeling” gigs in the gig economy overall, they tend to be staffed by contract agencies rather than true free agents, and mostly offer no financial or life-satisfaction advantages over similar paycheck jobs. They’re basically consolation prizes for jobs.

If you truly want to be an “indie,” then you are going to be fishing for “acting” gigs, not “modeling” gigs. In the short term, model questions help you tread water. In the long term, you sink or swim based on your actor questions. So the sooner you figure out what defines you as an actor, the more quickly you’re likely to break through.

Here are some examples of model vs. actor questions:

Model questions

1. What certifications should I get?

2. LLC or S-Corp? (US-specific)

3. Should I get into the SBIR game? (US-specific)

4. What industry niche should I pick?

5. How do I craft a pitch?

6. How do I describe my services?

Actor questions

1. What is the first thing people notice about me?

2. What are the unique associations that attach to me?

3. What do people typically want to talk to me about?

4. Who do I naturally attract and repel?

5. Why did I get this gig as opposed to someone else?

6. Could anyone else do this gig without rescoping?

To make it crystal clear, let’s cast all these example questions into actual model/actor questions:

Model questions

1. How tall do I need to be?

2. Should I try to break through in LA, Paris or New York?

3. Should I try to get a famous agent?

4. What roles in commercials can I fit into?

5. What kinds of portfolio photos do I need?

6. How should I dress for the audition?

Actor questions

1. What movie/show do people remember me from?

2. What catchphrases do people associate with me?

3. What scripts come my way?

4. Which directors/co-stars do I have good chemistry with?

5. Why did I get this role?

6. Could anyone else play this role without a rewrite?

Notice something? Model questions can be asked and answered before doing anything. Actor questions typically require you to already be in the game before they can be answered.

Another lens. Think about how actors and models are discovered. There’s a chance a model might be noticed by a scout on the street, but most are heavily groomed for the career from a young age, often by parents, and go knocking on the doors of agencies.

Actors on the other hand, are more likely to be noticed by casting agents or scouts in actual performances on stage or in bit roles. While there are famous stars who begin life as child stars, and there’s more of a learning curve to it, acting is much less of a career you can be groomed for. You have to just dive in and strategize your way to success.

It should be obvious that actor questions are all versions of the question, “what makes me pop memorably from context?”

Model questions are all versions of the question, “how can I fit harmoniously into the context?”

Getting to Good Questions

Newbies mostly obsess over the questions they do for one of two reasons: they are procrastinating on actually trying stuff, or they are trying to hold on to the securities of paycheck jobs by asking questions that are analogous to ones you ask while navigating a paycheck career. They usually don’t need the obvious answers pointed out either. Mostly, when they ask more experienced people these questions, they are wishfully hoping for miracle answers that aren’t there.

Of course, knowing how not to overthink the bad questions is not the same as knowing how to ask the good questions.

What’s a good question, beyond being an actor question that you have to ask and answer in a unique way about yourself?

A good question is one to which the answer supplies a ridiculous amount of liberating leverage. A question to which the right answer proves unreasonably effective in moving your career along. A strategic question that’s right for you, even if it looks banal or even ill-posed when asked for other people.

Most importantly, they are very fertile questions that lead to lots of good follow-on questions that generate more energy, via a cascade of self-discovery.

A good place to start looking for your good questions is to think about how people typically mock or typecast you.

In my own case, long before I started writing, a friend used to make fun of me for always “looking for the punchline” in conversations. I decided to own that. It eventually turned into a central skill in both my writing and consulting a decade later.

As an example of typecasting, my first viral blog post, The Gervais Principle, an analysis of The Office, led to an endless stream of requests to do the same kind of analysis for other TV shows. That’s basically typecasting.

Though I refused to let myself be typecast as “blogger who analyzes TV shows,” reflecting on that typecasting led to a series of very good questions and commitments that helped me develop my consulting practice. Some of those good questions, which will make no sense for anyone else, include:

• Am I good or evil? (answer: slightly evil)

• What’s my favorite deliverable medium? (answer: plain email)

• What’s my signature shtick? (answer: 2x2s)

It would take too long to explain how I got to these questions from reflecting on a viral blog post, but trust me, the dots do connect.

Getting to good questions is a process of following a trail of clues, and solving the mystery of who you are as a free-agent. When you’re done, you’ll have a story rather than an answer, one that energizes your career rather than merely removing some uncertainty from it.

And the only way to get to the good questions is to actually get started on your gig-economy career. They cannot be asked or answered a priori.