Month: July 2020

For people in paycheck careers, the “career path” is a familiar and useful long-term planning artifact. For free agents on the other hand, there is no such convenient construct, which makes meaningful long-term comparisons between paycheck and free-agent careers hard.

Worse, the lack of such a construct means free agents often fail to even imagine meaningful progression in the work lives, leading to increasing disenchantment through lack of growth.

So they do the same thing in Year 10 as they did in Year 1, not because they want to (which is a fine thing), but because they can’t imagine alternatives. Often, they end up rationalizing this lack of imagination (a bad thing) as lack of ambition (which can be piously spun as a holier-than-thou “good thing,” as in quitting the rat race and feeling superior to paycheck types).

We need a meaningful way to talk about long-term career planning for free agents, a way that allows for apples-to-apples comparisons with paycheck careers. And obviously we can’t use variables specific to paycheck jobs, like “title”, “budget” or “number of reports,” OR variables specific to free agents, such as “number of clients” or “bill rate.”

I made up a construct that I think works — a leverage graph. It is based on the observation that the unifying feature of both free-agent and paycheck careers is that if you do well, you land in situations with increasing leverage, via relatively discontinuous jumps. These jumps are promotions in paycheck careers, and new types of gigs in free-agent careers.

Let’s understand the concept in paycheck career terms first, since it is the more familiar and legible case. Here is the leverage graph (green line) for a typical high-flyer paycheck career:

I’ve left the term leverage undefined, but it is loosely anything that shapes the actions of the company beyond your individual work output. So individual contributors might produce something that is used by others in the company. Managers raise or lower the productivity of everyone under them based on how good or bad they are. Leverage is closely related to knowledge. The more you know and understand, the more you can consciously engage in leveraged behaviors with bigger consequences. Leverage is how knowledge turns into power over the organization’s fate. So a leverage curve is a big brother of a learning curve.

Here’s how you read this graph:

1. Each smooth curve is a learning curve with a single leverage type; the jumpy green curve is a leverage curve for an individual career that jumps across leverage types.

2. This diagram illustrates successful career paths with at least a little lifelong learning, but obviously people can and do “plateau” on a long S-curve or crash

3. Each smooth curve has slowly compounding gains over a single-leverage-type career; higher curves have faster rates of compounding leverage

4. The default curve is the solid line (individual contributor); you can stay on so long as you maintain a minimum acceptable performance for your experience level

5. The managerial curves (black dashed) are not default, but not exceptional either. There are systematic ways to get on them and stay on them.

6. The executive leadership curve (blue dashed) is exceptional, and crosses the other three. There is no systematic way to get on it or stay on it; you have to hack your way onto it.

7. There is a leverage distribution on each point of each curve. Not everybody on the same nominal smooth curve with the same years of experience has the same leverage.

8. Managerial curves feature normal leverage distributions at every point. Exceptionally good and exceptionally bad performers both tend to be weeded out.

9. Individual contributors and executives have non-normal leverage distributions. While exceptionally bad performers tend to be weeded out as on the managerial paths, exceptional stars (“10x” types) can persist and grow in their roles.

10. True promotions are leverage-increasing jumps across curves, and to be distinguished from grade-progression promotions within each curve.

Leverage in Paycheck Careers

The leverage graph should be familiar and easy to parse for people with some work experience, but here’s an illustration.

For engineers, for example, there are generally two recognized career paths in big companies. The first is a path as an individual contributor rising from an entry-level role to one with a title like “Principal Engineer” or “Fellow,” marking deep expertise in some area. The progression is often marked by a system of grades, such as 1-10. At Google, for instance, the two star celebrity engineers, Jeff Dean and Sanjay Ghemawat, are the only “Level 11” engineers among thousands at the company.

This path can play out across multiple companies within an industry that share a technological base.

The second path is a technical manager path, where you rise from individual contributor to some sort of general line management role, via an intermediate role in project or workgroup management. The difference between the two is whether you manage other managers, or whether you manage individual contributors (a crucial distinction that is central to management theory, but not critical for free agents to understand deeply unless you consult on organizational psychology problems). This path typically tops out at some level that is internally recognized as just short of an executive (aka business-risk-owning) role, such as an “Associate Vice President” or “Director.” The titles don’t matter. What matters is that leverage increases across and within curves.

Leverage (and compensation) can continue to increase after the company runs out of titles and grades to hand out.

Along either path, exceptional people tend to get picked out and groomed for executive leadership, but unlike progression through individual or managerial grades, the process is not systematic.

Engineers who rise to executive roles typically do so by showing a capacity for risk-taking leadership early in their careers, pulling off high-stakes projects that others didn’t think possible. This marks them for fast-track grooming for leadership, customized roles, and customized compensation packages. “Executive” roles typically begin with VP titles, but again, don’t take titles too seriously. It’s the substance of the role that matters — participation in the risk-taking of the business being central to the job.

The career paths in other functions such as sales and marketing are similar. Career paths in what are known as “staff” functions like HR are somewhat different, in ways that make this leverage graph view less useful.

Leverage in Free-Agent Careers

Now that we have the familiar paycheck career case established for reference within this leverage graph framework, this version for free agents should be easy to read.

Since most people bank a few years paycheck work experience before embarking on free-agent careers, the story begins at a non-zero quit point on the x axis. This is anecdotally around 5-10 years, though it is rapidly falling, and many younger free agents are skipping a paycheck world bootcamp altogether, either out of choice or necessity (which has consequences good and bad — they lack traditional organizational literacy, but also have fewer bad habits of thought to unlearn).

The big difference between the paycheck and free-agent versions is the nature of the leverage represented by the y axis. For paycheck types, it is budgets, number of reports rolling up to them, and participation level in strategic decisions. For free agents, it is informal influence in their economic sector. This difference leads to a particular portrait of the four smooth leverage curves a free agent must navigate:

1. The solopreneur is the equivalent of the life-long individual contributor, who slowly gets exceptionally good and increasingly unique at something. Their leverage lies in being the loci of accumulation for industry-wide best practice knowledge.

2. The thought leader is someone whose work directly influences the work and choices of others. As the derogatory jokes suggest, this is the equivalent of your basic project or workgroup manager within the corporation. The thought leader is the pointy-haired boss of the gig economy. Their influence is exercised in a diffuse way through public writing and speaking, and the production of artifacts (such as open-source programs or influential terminology) used by others. Their leverage lies in being the trusted loci of consensus formation around key trends, standards, and evolutionary choices in an industry.

3. The guild leader is someone who begins to take on something of a market-making role within the gig economy, helping people find gigs, making key backroom connections, and doing a degree of event organizing and community building. To the extent there is a need and opportunity for any sort of collective action, they catalyze it. Note though, that the incentives are wrong for them to play union-leader type roles, because the gig economy, especially above the API, is fundamentally an economy of unrepentant scabs who side with capital by default. The collective action takes other forms. Their leverage lies in being loci of network capital accumulation.

4. The mover and shaker is someone who can genuinely influence the course of events in an industry through the force of their personal reputation alone. An example is Linus Torvalds. He can shape the vast universe of Linux with his personal opinions, and exercise influence at a level similar to the CEOs of big tech companies. Their leverage lies in being the loci of extra-institutional agency based on connections to ground reality unmediated by large organizations.

Besides this big difference in sources of leverage, the free-agent leverage graph also has one other key difference: In the paycheck leverage graph, typically the curves are mutually exclusive. Managers rarely continue to do individual contribution work. Executives rarely spend a lot of time directly managing.

In the free-agent version though, this is not true. As I’ve illustrated with the forking green path, you often have to keep doing the work of the lower level curves even as you take on work on the upper levels. This means, at any given time, you’re exercising many different kinds of leverage simultaneously. Often this happens across the multiple gigs you might be doing at any given time.

For example, let’s say you’re doing 4 gigs at once:

1. In Gig 1, a solopreneur gig, which you got based on your paycheck resume, you’re applying a technical skill that the client lacks internally but is common in the industry.

2. In Gig 2, a thought leader gig, which you got via a viral blog post, you’re applying models and ideas unique to you to a specific challenge faced by the client, perhaps by delivering a workshop.

3. In Gig 3, a guild leader type gig, you’re helping a young startup new to a market map the environment, navigate crucial meetings, hire talent, and structure external relationships.

4. In Gig 4, a mover-and-shaker type gig, you’re sparring with a well-known executive, helping them make decisions that you know will set precedents for the industry and make the news.

Depending on the percent of time you’re devoting to each of these, and the amount of money you’re making from each, your role in the gig economy is some sort of superposition of the four curves. While people in paycheck roles do sometimes spread themselves out this way across projects, typically, they tend to play the same kind of role in every project.

So now that you have a construct for thinking about your career as a free agent, the question you have to ask yourself is: where are you, where are you headed, and where do you want to be headed?

One of the running themes in this newsletter is that indie consultants serve as shadows to the client principals they work with, especially leaders. To serve well in this role, it is important for indie consultants to learn to identify real leaders accurately, by a robust and useful intrinsic definition rather than by titles. Here is mine:

A leader is someone with a high level of individual agency within an organization, with responsibility for an independent connection to external reality.

For those who like Boydian jargon, a leader is simply someone who owns their OODA loop. Or more precisely, they own the risks of their agency and decisions.

I tend to only work with leaders by this definition. Not because I’m a snob, but because it is the easiest, most robust situation, and I’m lazy. Your job as an indie consultant is to get inside the OODA loop of the “client” as an ally, and help advance their goals. This is easiest when the client is a single person rather than an illegible ghost in the organizational machine.

Identifying Leaders

A leader is someone who can directly judge and use any thinking or work they sign off on. They are not intermediaries accepting counsel or advice on behalf of other individuals or groups, and sending it up or down a chain of command (or into the blackhole that often exists deep inside large organizations). They are not applying inflexible standards controlled by others that they lack the discretion to override.

When you work through non-leader intermediaries, there is high risk that you will end up doing the wrong thing, or doing the thing wrong.

For example, perhaps you do work for a low-agency middle manager who is sourcing a report that will be presented to the CEO. The CEO will actually sign off on the report, declaring it good or bad, but you never get to meet them while doing the work. In such a situation, the chances of things going wrong are very high. Your chances of getting stiffed on the payment go up. The likelihood that you’ll get thrown under the bus and blamed for failure goes up. The chances of reputational damage go up.

All these risks can be mitigated and managed, and it’s possible to craft good gigs out of such situations, but it is neither easy nor particularly fun. So it is best to work directly for leaders when you can.

A true leader will acquire and maintain control of as much financial agency they need to do what they think is their job, including the ability to pay for other people’s time and labor. If they can’t acquire this agency, they will typically leave.

This means for an indie, a leader is also someone who can in practice determine entirely on their own whether to pay you, even if they nominally need someone else to sign off. Being recognized as a leader within an organization means your funding requests within your domain are not typically challenged. So you, as an indie, only have to make one person happy.

Leaders include executives by default, and others (such as uniquely skilled individual contributors) by exception.

Trust, but verify, that the defaults hold. You might find leaders in unexpected places, who are a pleasure to work for, or you might find that someone who walks and talks like a leader, and has all the right titles, isn’t actually a leader in any meaningful way.

Finally, don’t go by size of organization a leader runs. Leaders may or may not have a large number of reports “rolling up” to them, but they tend leave as much of the direct management work to others as they can.

Having to directly manage a lot of people directly weakens leadership tendencies, and strong executives tend to limit that to a few direct reports, so they can focus on leading. They encourage high-autonomy organizations where people need little management.

This does not mean they neglect people working for them. It just means they have a laissez-faire approach based on high situation awareness, strategic intervention behaviors, and strong inspection and monitoring habits. Like good teachers, they seem to have eyes in the back of their head. They are able to get the behaviors they want out of the organizations they lead without micromanaging or spending all their time in meetings with reports.

But their focus is on leading, not managing.

Working with Leaders

Within the idea of an indie as a shadow, there are two aspects to working with leaders, an opposed aspect and an integrated aspect. In areas where the leader is still growing, you occupy a somewhat opposed role, where you are growing as well. In areas where they have integrated personalities (where they have “eaten their shadow”) you have to occupy a much more aligned role, and you need to be integrated in complementary ways.

The net effect is something like being an evil twin. The “evil” part is the opposed growth aspect. The “twin” part is the integrated aspect.

Sparring work in particular, is about managing the tension of these two aspects of work. This means your ideal client is someone who is mature in the same ways you are, and growing in the same ways you are, just from the “other side.”

When this condition is not met, elements of coaching (teacher/learner) dynamics enter the sparring work. I personally tend to avoid this, again because it makes things harder. Being cast as a teacher or student in a consulting relationship means there are mis-aligned learning curves to navigate, in addition to the actual work of the gig itself. This introduces additional risks into the gig: they may like the work but be disappointed in your performance as a teacher or student. Or vice versa.

Again, the risks of learning curve elements can be mitigated and managed, and as with working for organizations instead of individuals, it’s possible to craft good gigs out of such situations. But as in that case, it is neither easy nor particularly fun. So it is best to work directly for evil twin leaders when you can.

Opposed Aspect Work

For the opposed aspect (where you’re growing together), the shadow aspect of everything positive associated with leaders is often a visible part of the perception of consultants they work with.

• If leaders are missionary, their indie consultants are mercenary

• If leaders are idealistic, their indie consultants are cynical

• If leaders are holy warriors, their indie consultants are pragmatic operators

• If leaders are charismatic stars, their indie consultants are grey blurs

• If leaders are taciturn doers, their indie consultants are voluble talkers

Generally only indies can truly play this opposed role. Consultants from larger firms don’t relate individually to leaders in the same way. Instead, the self-shadow relationship holds at an organizational, firm-to-firm level.

This default shadow role means the default perception of an indie consultant showing up in an organization is negative. This is why it is important for indies to be conscious of their halos. Consciously managed halos are how you counter-program default negative perceptions (created by the shadow position). You will never completely counter-program it, and that’s not a good thing to aim for anyway. You just want to be perceived in a way that allows you to be effective. You don’t need to be universally liked or admired within the organization. It’s okay to be in the shadow zone.

That said, in rare situations, the default perception of an indie consultant is positive. If the principal has a terrible reputation, then people supporting them can sometimes end up with positive perceptions, as foils who mitigate the negative traits. These are not good clients to work for generally.

Basically, you are the evil twin in the relationship by default, but if the principal is obviously seen as evil by everybody, you might be seen as good.

Integrated Aspect Work

If you have a passing familiarity with Jungian psychology, you’ve probably heard something along the lines of self-actualization being about “eating the shadow” or “integrating the self.”

This means, as (and if) they grow and become more self-actualized, leaders and their indie consultants start to resemble each other in key ways. Each begins to integrate their personality in complementary ways to the other.

This is why it is important to primarily work with clients you admire and respect. You are their shadow, but they are yours too. Either both of you grow, or neither of you does.

But while working in areas of shared growth is fun, working in areas of shared maturity is even more fun.

The biggest such area is being right. I got the idea from the Amazon leadership principles (a rare non-vacuous document of its kind) that includes this one: Good leaders are right a lot. You can actually make a triad of such statements:

• Good leaders are right a lot

• Good managers win a lot

• Good employees accomplish a lot

It is crucial to recognize that leadership often means being right but not winning. This is because leaders own risks they don’t entirely control, which means their game is more like poker than chess. Even with perfect play and no mistakes, they might lose.

By contrast, managers tend to control the risks they own, and play more deterministic games, so it is appropriate to judge them based on their win rates.

And down the hierarchy, non-leader individual contributor employees are typically judged on effort and output, whether or not it is winning output, or output that is right about a lot. That’s called doing your job, within the inner reality of the organization.

For an indie consultant working with a strong leader, striving to be right a lot, in ways that are complementary to ways in which the principal is right a lot, is the most important area of aligned, integrated work.

• Good leaders are right a lot. Good indie consultants are right a lot.

There are several other areas where leaders and their consultants can be aligned and integrated, but this is the most important one. They have aligned gut instincts, and are therefore right a lot in complementary ways. When they disagree, chances are, there is either incorrect or missing information in the picture, or an analytical error somewhere. So it is possible to have an important and interesting discussion that gets somewhere, instead of a futile argument that runs aground on fundamental misalignments.

A recurring theme in this newsletter is that gig work is shadow work. One of the subtle consequences of this is that the gig economy is extremely fragmented and arbitrary in structure and behavior. Once you get past the broad 3-way distinction among indie consultants, contractors, and platformers, the detailed structure of the terrain is really hard to map out. Generalizations and narrative threads are for the mainstream paycheck economy. The gig economy is defined primarily by the glitches, exceptions, and incoherencies of the mainstream paycheck economy.

Our messy map is the reason their suspiciously clean map doesn’t fall apart.

The gig economy is the part that’s been swept under the rug. It is the set of patches for the mismatch between the map — the institutional landscape with its org charts and job descriptions — and the territory of economic reality. That’s why the gig economy is by definition also the shadow labor economy. And no part is more shadowy than the indie consulting part.

I took a shot at making a map of indie consulting as a shadow zone. This is a draft beta version that I intend to refine and label/annotate properly in future versions. It is meant to suggest broad contours, not exhaustively cover every sort of indie consulting you could do. I’ll explain the overall logic, and then drill down into a few of the markets to illustrate.

The map reflects the fact that indie consulting is the messiest and most shadowy of the three subsectors of the gig economy. Why?

• The contracting subsector inherits the structure of the paycheck workforce via extension/augmentation. Every contractor in principle could be converted to a regular employee in a simple way by extending or re-scoping the org chart.

• The under-the-API platformer subsector has a structure dictated by platform architecture and various algorithms that handle tasking and coordination.

• But the indie-consulting world? No structural forcing function, but a great deal of shadow energy. Which is why you end up with a picture like the one above.

In the map above, the x-axis represents the level of client principal you serve, the main person you deliver to, who signs off on your work. The y-axis is the basic category of consulting offering: skills-based, process-based, or strategy-based. The distinctions are the obvious ones:

• A skill is anything learnable that you can improve with practice, and acquire prowess at. If you can win a grade or excellence award at it, it’s a skill.

• A process is anything that primarily needs some sort of basic procedural literacy, and conscientiousness, rather than talent to do well. If it doesn’t take much practice, and you can earn a certification for it, it’s a process.

• Strategy is anything that relies on insight rather than prowess or conscientiousness. If you can earn an illegible reputation for it, but awards and certifications for it are cringe, it’s strategy.

Now the thing about this 3×3 grid — shown as light dashed lines — is that it’s tempting to identify each “square” as a clean-edged role you could play. Unfortunately for us, the gig economy does not allow for such clean boundaries.

Each of those squares is actually a typical paycheck role (likely occupied by your client). For example, executive leadership + strategy = CEO, executive leadership + process = VP, Human Resources, executive leadership + skill = CFO (I’ll leave the other 6 boxes for you to fill out as homework).

But our map is based on ways in which their nice map fails to actually cover the territory it is expected to cover. So each indie consulting niche is like a fragmented country on this map. It has a main coverage region, but also a bunch of scattered outposts.

There are 10 offering-based markets on this map, but I won’t attempt to describe all of them in detail, only the ones I have some experience of.

Insight-based Indie

I’ll start with my market. As an insight-based indie, mainly offering things that get labeled “strategy,” most of what I do is in the top right corner, and is delivered through 2 kinds of offerings: sparring and investigations.

But not all of what I do is in that corner, and I don’t cover all of the needs of that corner. There are isolated spots of sparring and investigation required in the “skill” row, and some bleed-over into the “process” row (for example, OODA-related things I do often bleed into the middle).

One of the reasons strategy offerings for executives is so dominated by “sparring” relationships is that leadership is famously and visibly a lonely, solitary kind of work. So the primary “shadow” need is actually intellectual company that can keep up. As a result, much of what is delivered in this corner is delivered through sparring style interaction, even though the content can be hugely varied.

Skill-based consulting

This is probably the most crowded market on the indie consulting map, and the place where most younger entrants into the gig economy start out.

It tends to include anything that is adjacent to an individual contributor skill. I very rarely operate in this market, but when I do, I make sure it is something I deeply enjoy doing hands-on, and typically don’t bother about billing time accurately. I’m happy to spend more time on this kind of thing than the client might think reasonable, to get it right by my own standards and curiosities.

One way to think of this market is that it can be described via prefixes like pre-, post-, meta-, para-, or infra- attached to individual contributor paycheck employee roles.

For example, (software) architecture skills are a kind of meta-development (the real architecture part, not development title-inflated to architecture). So an actually skilled and experienced Scrum trainer would fit into this market.

Design skills are a sort of pre-product development skill. You won’t be doing all the detailed engineering or design work, but you might be crafting the broad approach and creating the design space for the adjacent employees to work with.

Often this kind of consulting builds up a foundation, capability, or starting condition in a short period and then hands it over to regular employees to run in production mode. Either that, or it is a transient “special projects” type need that does not need sustaining once it’s achieved its objectives.

Notably, you deliver via a skill, but not to the adjacent-role individual contributor paycheck employees who will eventually take over, or even their managers. For maximal impact, you must deliver to executive leaders who own the risks of the initiative (if you’re delivering to another locus, chances are, the project will fail).

Sometimes you can turn skill-based consulting into strategy content for individual contributors, via a blog post or a talk for instance, in the square dominated by business book writing. Other times, you might coach individual contributors briefly, especially in hand-off processes. But in general, you should be selling to executives, either to get some new risky initiative off the ground, or as a special project.

Managerial Indie

A harsh truth about hierarchical organizations is that the amount of room shrinks as you go up the corporate ladder. This means a lot of indies start out mid-career when they find they’ve hit some sort of ceiling and can’t get promoted, but are too bored or frustrated to remain at their current level. Or they’ve just been laid off. So they go sideways and turn into managerial indies.

Managerial indie offerings are typically things that require a degree of managerial experience and skill (and often based on something they first learned to do as an employee), but are primarily based on conscientious delivery. A dead giveaway is that you offer the same thing to many clients, with little to no modification. If it can be labeled a “best practice” it can be a managerial indie offering.

Stuff like workshops and retreats are the bread-and-butter for this kind of indie, and often this attracts the most bureaucratic types who crashed out of their paycheck careers through cluelessness. In the indie world, this cluelessness can sometimes turn into an asset, since it comes with an infectious enthusiasm that can charm clients despite being borderline cringe. On the flip side, on occasion, when clueless types clue up, they can often get radicalized and resentful, and turn to grift — and nothing is easier to turn into a grift than a managerial indie offering. They know how organizations work, and are pissed off enough at society at large to use that knowledge against the world.

As a result, a lot of managerial indie consulting work is offerings that are more theatrical and CYA than impactful. But when these offerings are crafted and delivered well, they can be very interesting to do, and valuable to get as a client.

I’ve done this sort of thing occasionally, but frankly I don’t enjoy it, and am not conscientious enough to do it well, especially repeatedly without much change. The exception is when it’s a workshoppy topic that lends itself to very high customization and context-dependent redesign for each client. So it’s essentially fun each time, and has strong skill or strategy components to it.

One special type of offering in this market is troubleshooting. Experienced managers who were once skilled individual contributors are often the best troubleshooters for tricky, highly specific problems that confound employees without the right experience. If this were a common type, it would be a market in its own right, but typically so few people do this well, they tend to present as regular managerial indies, but with a “fixer” or “bagman” footnote to their nominal reputations.

Functional Expert

Finally, there is the functional expert. It can be hard to tell this kind of indie apart from the managerial indie, since both are typically mid-career and process-focused. The difference is that the functional expert typically brings seasoned individual contributor abilities to the party, rather than managerial, and delivers to individual contributors rather than managers.

Often this involves experience with highly domain or industry-specific tools (such as SAP) that are not taught in schools, and have to be learned on the job. The presence of specialized tools means that compared to the manager-indie market, there is some resistance to bullshit. But don’t trust that too much. It is possible, just harder, to sell a lot of bullshit tooling, and training for that tooling.

This is a type of consulting I’ve never done (I have no relevant skills of this sort), and never want to do, but have seen close-up a lot.

One “tell” of this type is that they go to industry conferences a lot, and all know each other within a given geography or market. They are the most heavily networked of all indies, and present a guild-like brand. There’s a good chance they’ve authored an O’Reilly type book.

Other Markets

To wrap up, the 6 markets I didn’t cover in detail (due to a mix of limited knowledge and limited interest) are:

1. Coaching: Anything involving 1:1 soft or meta-skills training and mentorship for individual contributors that is typically not available in schools and can’t be learned from books alone. Coaching qua coaching is typically an early career market. So-called executive coaching is, I’m increasingly convinced, 90% either sparring, or therapy in disguise. The rare specialized coaching you need at executive level, such as media-training, is usually procedural rather than strategy or skill-based.

2. Psychology, motivation, and testing: Highly adjacent to the managerial indie market, but with a bigger skill component. Stuff like non-violent communication, motivating employees, active listening, Myers-Briggs. You can often earn premium-mediocre credentials in this market that are somewhere between certifications and actual hard skills.

3. Trend report/analyst work: This is probably the most legible kind of indie consulting work and is the most “researchy” kind of offering. It also has the biggest moat for indies, since it takes serious time, effort, and network capital to produce. Which means you’re most likely to get this kind of work via an intermediary analyst firm. Or you burn up savings producing it on spec, hoping to sell it once you’re done.

4. Regulation, compliance, legal, media: Self-explanatory. Any kind of indie consulting that involves pragmatically navigating an arbitrary and complex external maze. Unlike the adjacent workshops/retreats market, this market is created by 3rd parties like the government or media forcing your clients to do something.

5. Airport business books: It is hard to sell “strategy” offerings to individual contributors because of the impedance mismatch. Strategy work costs time and money to produce. That’s why you can bill 4-10x as much for sparring work as for coaching work, and why analyst reports go for thousands of dollars. The only way to make money off individual contributor interest in strategy matters is via a mass product: a book typically. But this category includes anything that can be sold indefinitely via distribution (including recorded workshops, materials, and workbooks).

6. Ethics: I’m breaking this out as a separate market even though it’s tiny and usually absorbed in one of the adjacent markets (sparring if you want to think seriously about hard ethics conundrums, compliance if you just want to comply with the letter of ethics regulations enforced by the government or other external party).

There is a lot to be said about all these markets of course, and my own direct experience of most of them is fairly limited. As I said, I’ll be refining this map, and perhaps in the future inviting guest contributions to cover parts of it where I’m weak.

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.

Independent consulting and independent investing share some tantalizing similarities. Both involve direct risk-taking, without an organization providing a safety net for you. In both, you have to strategize about returns that are not strictly causal functions of effort (ie you have to wrangle luck). Both are activities that inhabit a larger open-world economy of macro-trends and forces where you can try to go to where the action is, instead of waiting for the action to come to an organization that employs you. Both are unlike paycheck employment in that it is hard to blame others for “unfair” consequences. You have to own the results of your actions, good or bad.

But there are two crucial differences.

First, for investors, the primary input is capital, while for consultants, the primary input is time. Second for investors, the primary driver of returns is exogenous events, while for consultants, the primary driver of returns is the quality of your own actions.

Basically, as a consultant, you primarily create or destroy value directly, as a result of your efforts. An investor on the other hand, primarily banks profits or losses due to creative destruction happening out there in the economy.

As an example, take conducting a workshop versus executing a trade based on some information. A significant part of the returns from a workshop depend on the workshop itself being good or bad. For a trade on the other hand, the returns are good or bad depending on how the world actually behaves. You might have set up a technically perfect trade, but lose because the world does something else. Or you might have set up a sloppy trade, but the world does something that makes it a winning move anyway.

One clear way this difference shows up: As a consultant, you tend to win big when you do good, smart work that opens more doors, drives referrals, brings in more interesting and lucrative gigs, etc.

As an investor, you tend to win big when the world does stupid things. Legendary trades on Wall Street tend to happen in the context of crashes and meltdowns, where a minority presciently bet against the world.

Investor World vs. Consultant World

Let’s capture these ideas in two graphs representing the investor world and the consultant world respectively. In both cases, there is a curve of proportionate rewards and losses (yellow-orange) where value is created or destroyed based on the quality of your effort (smart/stupid) and a curve of serendipitous/zemblanitous (“surprisingly lucky” vs. “unsurprisingly unlucky”). Here the red/green curves are the net return curves — the proportionate returns plus the effects of unexpected good or bad luck.

Here we’ve assumed a convex (what Nassim Taleb calls antifragile) world for both the investor and consultant, with increasing-returns upsides, and bounded-losses downsides. But the x-axis is different for the two cases. For the investor, the x-axis represents severity of positive or negative events relative to the logic of the trade. For the consultant, the x-axis is smartness or stupidity of the effort.

In both cases, we’ve assumed a synchronization in the crossover points for both proportionate consequences and luck effects.

The difference between the two worlds, as illustrated is twofold:

• The x-axis is different (event quality vs. effort quality)

• Relative proportion of proportionate returns (orange-yellow) in net returns (red-green)

(of course both event and effort quality apply to both, but I’m not about to plot a 3d graph here for what is already an outrageously cartoonish model)

As you can see, very little of the gains or losses of the investor can be attributed to the creative, causal effects of the trading actions. Trades do not create or destroy value by themselves (unless you’re a market mover like Warren Buffett, whose trades are read as “smart money”, implying quality, resulting in a premium). They allow value to flow from one part of the economy to the other, usually with a degree of entropic loss along the way.

Now that we have a basic picture in our head, let’s examine some varieties.

Four Consulting Regimes

It is useful to carve up consulting activities along two axes: whether the environment is one of scarcity or abundance, and whether the consultant’s own actions are strategic or not.

Strategic is not the same as smart. Strategic means you’re taking advantage of being a free agent to constantly discover or create opportunities for yourself that would not be open to you as a paycheck employee confined to a single company. So for example, if you do a good project whose results are public, you can parley that into getting more gigs of the right sort at a better rate. Regardless of their strategic abilities, paycheck employees are limited in their ability to act strategically by the limits of their environment.

Here’s the 2×2:

There are four regimes here:

• Non-strategic and scarcity: you’re exposed to non-convex conditions and high downside zemblanity risks. There will be little luck for smart effort, and highly compounded negative consequences for dumb effort (eg: drain your savings and then get hit by a health crisis with no safety net).

• Non-strategic and abundance: conditions are nice, and you might enjoy a little luck with smart effort, and your downsides will be capped. Overall, it’s not that different from being a paycheck employee. Your gains and losses are just exaggerated a bit, due to higher exposure to luck forces. You’re neither benefiting too much, nor suffering too much, for being in the open economy instead of in the safety of a paycheck job.

• Strategic and scarcity: The curve looks very similar to the diagonally opposite non-strategic/abundance quadrant, but here, there’s a chance you’re doing much better than paycheck employees at bad companies. You’re leveraging your freedom and strategic imagination to reshape a potentially default bad returns curve into a good one.

• Strategic and abundance: This is what we’re all shooting for, a regime that’s unavailable to paycheck people, where net serendipitous returns on smart effort grow, even as the proportionate rewards get smaller as a fraction. If you go sufficiently far to the right, the proportion starts to look like the profile of investing activity. Your time becomes as good as money.

In my 9 years so far, I have spent significant periods in all four quadrants. Net, I’d say my average situation has been strategic-and-scarcity, but with some delightful periods of strategic-and-abundance.

In the scenarios above, we’ve continued to assume synchronization: that the world will get lucky or unlucky in lockstep with your actions getting smarter or stupider. This is of course the most unrealistic assumption.

In general, the crossover points for the “luck” and “proportionate rewards” curves won’t coincide. To steal a term from the printing world, there will be a registration error (the term comes from situations like printheads being misaligned, leading to different colored inks being laid down differently, leading to weird artifacts at edges).

Misregistered Worlds

Let’s talk about worlds with registration errors. There are four kinds that you should be aware of (not on a 2×2 though):

• A stupid-lucky world is one where whether your efforts are smart or stupid, you still win overall. The net returns curve stays safely above the x-axis, and a nice green band keeps you above zero returns. You actually have to think hard to find ways to lose.

• A perverse world is one where smart effort actually leads to net mounting losses, while stupid effort is rewarded with net increasing gains. Be careful about jumping to the conclusion that you actually inhabit a perverse world. Most of the time, when the world seems to be acting perverse, it’s your assessment of smart/stupid in your actions that is backwards. That, or you’re being gaslit by someone with an agenda. Perverse worlds are actually rare. You’d be surprised how often people code their actions backwards because they can’t tell stupid and smart apart, and therefore project it as perversity onto the world.

• A pure dystopia is the opposite of a stupid-lucky world, where whether your actions are smart or stupid, the proportionate gains and losses are always swamped by overwhelming bad luck. There is always a red band of pain, and you’re always underwater, taking net losses.

• Finally, bahramdipity refers to a world that is fundamentally serendipitous, but malign forces try to kill the serendipity. This means that up to a point, positive smart effort will still lead to negative returns. But if you push hard enough, you might overcome the malign forces and start winning. So there is an effort deadzone where there is a proportionate positive return (the little yellow wedge near the crossover point) that is swamped by a negative environmental drag.

There’s a lot more you could do with these effort/return diagrams and parsing of luck effects vs. proportionate effects, but I’ll stop here. I’ve already built a rather wobbly edifice here, on the strength of a rather shaky analogy between investing and consulting.

Ultimately, the graphs and notional varieties are just scaffolding for thinking about luck, smarts, strategy, and environments. If you don’t like thinking in terms of convexity and effort/event vs. returns curves, you can reframe it more simply as a set of lessons about how best to invest in yourself. So I give you…

Consulting Like an Investor: Seven Principles

1. Independent consulting is like independent investing, except that you’re investing time into the quality of your own efforts rather than capital into beliefs about events in the world.

2. Going independent is giving yourself permission to be strategic, and putting yourself in a playing field — the broader labor market — with opportunity for strategy, just as investing is putting yourself into a broader financial market than your local bank.

3. Because you’re primarily investing time rather than capital, strategy is about quality of effort you put into your creative output, not the nature of events.

4. The winds of good and bad luck are often, but not always, synchronized with the smartness or stupidity of your actions. Be attuned to this synchronization state.

5. Strategy is a lot more consequential under conditions of scarcity, to reshape default bad into default good returns curves, but the relative positive returns of free agency primarily accrue when you figure out how to be strategic in good times. Strategy under scarcity makes survival as a free agent possible. Strategy under abundance makes survival as a free agent worthwhile, and preferable to paycheck employment.

6. Being strategic is not the same as your efforts being smart. Smart vs. stupid is about what you do within a gig. Strategic vs. not-strategic is what you do between gigs.

7. The world is often in a state of misregistration, and you have to be sensitive to four kinds of environment in particular: stupid-lucky, perverse, dystopian, and bahramdipity. Inhabit stupid lucky worlds if you can, and bahramdipitous ones if you must. Get the hell out of perverse or dystopian environments as soon as you can. 80% of strategy is putting yourself in the right environment. 20% is about what you do there.