Month: February 2021

In the first three parts of my look at the evolution of the gig economy from my own 10-years-in perspective, I looked ±10 years at the 3 layers of the stack that I think of as forming the background canvas of our work: workflows, trust, and money.

In this part, I want to explore what I think of as the element between foreground and background: scenarios. Scenarios are how you imagine how evolving patterns in workflows, trust, and money coming together around big, external, non-economic forcing functions to form larger economic stories. These stories cannot be told in the form of a “view from nowhere.” They can only be told from a particular interested perspective: in our case, that of the indie consultant.

Looking out at the future is only a meaningful exercise if you look back at least as far in the past: after all scenarios that cannot even achieve consistency with the past have little hope of comprehending the future. And for telling big stories and positioning yourself within them, you have to look past the boundaries of your own chapter.

But to avoid getting trapped by a single story, you have to tell yourself multiple stories.

Four Stories

Here are 4 ways to look at the last 50 years of consulting, and corresponding ways of looking at the next 10 years. These 4 scenarios are very US-centric, but there will always be some bias in this sort of scenario construction, and US-centricity remains the best bias for telling any story of global significance. In the future, China-centricity might be the right way to develop scenarios, but we’re not there yet I think.

These are not meant to be great models of evocative storytelling, but as quick glosses of stories that seem implicit in the way significant clusters of people seem to think about indie consulting.

Story 1: A New Technocracy

Modern consulting emerged in the 1970s following the oil shocks and the rise of Japanese competition, making the MBA a sought-after degree. With deregulation, through the eighties and nineties, it continued to grow as an industry in prestige and influence, and came to be regarded as the main repository of business knowledge.

After 2000, the growth of the digital economy, and increasing perceptions of cronyism, corruption, and being out of touch began to slowly tarnish the reputation of the sector. The industry found it especially hard to make inroads into the emerging technology sector, which had a natural hostility to MBA-style consulting. Though it managed to establish a foothold, especially on the business side of the larger companies, it could not penetrate to the technological side, or down to the smaller startup scales, where much of the real action was.

Unlike in the old economy, big institutional consultants were essentially cut out of the most consequential conversations, even though they were able to access a large share of the available money. Talented young people in MBA programs read the writing on the wall, and increasingly began migrating directly to the heart of Silicon Valley, choosing to work in VC firms, directly for big companies, or even found startups. Others began migrating to Asia, establishing direct footholds and expertise in the Chinese sphere of influence.

In this environment, independent consulting began to take root, especially around boutique needs requiring deeper technical knowledge, alloyed with management experience in the new economy.

Over the next fifteen years, a large boutique industry of indie consultants emerged, offering expertise in every aspect of the new economy from SEO and growth hacking to product strategy and UX design, to database scaling and sourcing manufacturing in China. Blogs, newsletters, Twitter, and podcasts became the preferred source of business expertise, displacing traditional sources like consultant company reports, business books, or the Harvard Business Review. Private online forums began displacing old-style backroom conversations.

Through the Great Weirding (2015-20), the divide grew deeper, as the old consulting industry became increasingly out of touch, and the emerging indie sector gained credibility and professionalism rapidly.

In the next 10 years, the trend will continue, as indies organize more effectively to take on larger, more complex engagements, and offer more imaginative services at lower cost, with less focus on paper trails and manufactured justifications and more focus on fundamental problem solving. They will go beyond solo gigs to networked collaborations in larger teams.

As we head into an era defined by climate change, decarbonization, and deep reconstruction, indies will be critical to navigating events with agility and real problem-solving intelligence, since technology is the main lever for addressing the big challenges of the post-Covid world.

Sclerotic and cronyist consulting firms will be left behind and die along with the old economy they serve.

Story 2: A New Socialist Hope

Modern consulting emerged as a dark force in the 70s, as several decades of thoughtful and compassionate politics from FDR to LBJ drew to a close, and the ambitious social programs of the Great Society floundered during the Nixon administration.

An economy founded on treating workers well and fostering inclusive growth gave way to the rapacity of neoliberalism, marked by the greed of supply side economics, globalization, union-busting and deregulation. For a quarter of a century, traditional consulting served as the mercenary sword arm of capital, extracting an ever-greater share of profits from labor, and working with oligarchs and totalitarian regimes across the world to create and secure a global system of exploitation. Unions were busted, environmental and civil rights concerns were tossed aside, and sociopathic business leaders, supported by consultants, systematically stole the future from the people and made it the preserve of the 1%.

In this environment, indie consulting emerged as a boutique segment of individuals who combined highly valuable technological skills with a sense of integrity and ethics. Between 1992-2015, indies used the cheap and disruptive tools and technologies provided by the internet to gradually create and offer a systematic alternative to the corruption and cronyism of the old economy. At the same time, they pioneered a third way of work, rejecting both the role of neoliberal exploiter and exploited low-agency worker, to make their own way with dignity, using digital tools to asymmetric advantage.

Through the Great Weirding (2015-20), the contradictions of the neoliberal world order finally became unsustainable. And though Bernie Sanders did not win in 2020, the election of Joe Biden finally offers some hope for a new, more equitable future, and a return to dignity and prosperity for all has become possible.

In the next decade, indies will be at the forefront of a revitalized middle class and a socially aware and ethical response to climate change. Though unions are obsolete and beset by the same kinds of corruption that plague other neoliberal institutions, new kinds of collective action based on a new authenticity and post-capitalist modes of solidarity will emerge. Indies will be at the head of this movement.

A compassionate, socially conscious, networked workforce, supported by mechanisms like UBI and universal healthcare, will emerge to form the new backbone of the post-Covid decarbonizing economy.

Story 3: More Neoliberal Than Thou

Modern consulting emerged in the 1970s alongside fresh new ideas in economics and wealth creation. Thanks to the oil shocks and Japanese competition, moribund and inefficient American industry was shocked out of its complacency and forced to scramble to remain competitive. Decades of indulgent socialist policies had created a corrupt, bureaucratic, and inefficient economy with stagnant innovation, weak leadership, and a non-existent strategic culture.

Between 1980 and 2000, consulting played a critical role in making the American economy competitive, efficient, and innovative again, driving the greatest burst of wealth creation in history. It however, became a victim of its own success, growing complacent and corrupt in turn.

Indie consulting emerged alongside the internet as an agile, entrepreneurial, and effective alternative source of business knowledge and strategic capability that slowly began beating the traditional consulting world at its own game. Using the internet as a tool for asymmetric advantage, it slowly established itself as the go-to source of competitive advantage in the emerging tech industry. A new economy built on startups needed a new kind of consulting that was itself organized in startup-mode.

Through the Great Weirding (2015-20), the indie world finally came of age, with its own “passion economy” stack allowing it to compete sustainably. In the next decade, traditional consulting will recede and decline, and as the passion economy stack matures and grows, indies will grow along with it. Blockchain-based technologies will be especially important in this evolution.

The future will only have more and more post-industrial, post-capitalist weirdness and the unique challenges of climate change, which will not yield to business-as-usual thinking.

Indies will be at the forefront of helping the economy innovate its way through the challenges of a post-Covid decarbonizing economy with an entrepreneurial approach to big problems.

The traditional consulting industry, full of empty suits, may have started this game, but indie consultants, armed with just a laptop, internet connection, and blockchains, will finish it. The traditional consulting world will simply be unable to keep up in this accelerationist future.

Story 4: The Empire Strikes Back

Modern consulting emerged in the 1970s alongside monetarist economics and globalization. It was instrumental in creating the neoliberal world order and the great wealth that flowed from it.

When the internet economy emerged in the 2000s, the traditional consulting industry was initially caught flat-footed, but it learned rapidly and reinvented itself. It soon became an essential part of the new economy. In the first two decades, the tech sector had all the problems of emerging frontier economies. It was full of grifters and amateurs wielding outsize influence, and playing roles normally played by seasoned business veterans. Due to the small scale of much of the early-stage startup world, and the newness of the technologies being adopted rapidly, it took some time for the traditional consulting industry to catch up. But as the early tech companies grew into giant platforms that dominated the economy, consulting firms reinvented themselves for the digital age through acquisitions and building up of new tech practices. They successfully migrated from the old economy and established themselves as partners for the new economy, bringing much-needed professionalism and seriousness to the sector.

In the future, as tech matures and large companies continue to shape the future, the wild frontier of indie consultants and boutique operations will consolidate and become integrated with the traditional consulting industry. A new normal will emerge, leaving behind the anomalous dynamics of the Great Weirding (2015-20) will soon be a distant memory, like the Wild West.

As climate change and China increasingly become the priority for businesses post-Covid, the resources, scale, and deep global expertise of the the consulting industry will once more come to the fore. The wild west will be tamed, and deep expertise and institutional knowledge will come to be valued once again.

Eight Questions

Before we proceed, ask yourself these 8 questions:

1. Which scenario do you most resonate with?

2. Which one do you least resonate with?

3. What can you see with greater clarity through each story

4. What are the blindspots baked into each story?

5. What sort of indie is described by each story?

6. What sort of client is described by each story?

7. Which of these stories are best/least supported by known numbers?

8. What story threads do the available numbers not capture?

If you like, post your thoughts on these questions as comments below.

Now for some commentary.

Seeing Through Scenarios

In case it isn’t obvious, these 4 scenarios correspond roughly to the 4 quadrants of the well-known political compass:

• Story 1, A New Technocracy is a Left Libertarian future

• Story 2, A New Socialist Hope, is a Left Authoritarian future

• Story 3, More Neoliberal Than Thou, is a Right Libertarian future

• Story 4, The Empire Strikes Back, is a Right Authoritarian future

I’m probably hoping for Story 1 with some elements of Stories 3 and 2, perhaps an 70-20-10 mix, but that’s probably wishful thinking. I suspect the actual future will be about 10-20-5-30, for a total of 65%. I’d guess about 35% will be stuff nobody saw coming.

There are, of course, way more than 4 stories that can be told about the next ten years, and every way of reading the past leads to a way of reading the future. And every story offers its own way of grappling with known new elements in the landscape and unknown unknowns.

In this case, the new elements I incorporated are: Covid, China, Climate, and Crypto. The 4Cs of futurism today. They are not the only elements stories could or should be aware of, but scenario building is about making choices, since you only have so much room in a story.

The trick is to tell yourself many stories, and believe in all of them enough to become sensitized to the truths they uniquely apprehend, but be skeptical enough of all of them to avoid getting wishfully attached to, or blinded by, any of them. That is perhaps the best way to leave yourself open to the upsides of what nobody saw coming, and prepared against downsides that at least somebody saw coming.

Next week, for my 10th anniversary post, I plan to pull together this series with a grand finale exploring the most important question: what am I going to do with myself?

In the first two parts of my ±10 years look at the evolution of the gig economy from my own 10-years-in perspective, I looked at the 2 lowest layers of the stack: workflows and trust. The third layer is what I think of as the money layer. It is for free agents what the management layer is for the paycheck world.

What did the money layer look like in 2011? What does it look like in 2021? What might it look like in 2031?

These are not the questions you might think they are. It’s not about your money, but about money in general. What is it? Where it is? Who controls it? Where is it going? How does it flow? How is its fundamental nature changing?

You should be curious about these questions, independently of what seems to be the main selfish question: how to get some of it?

As a free agent, you live dangerously at the assembly language and API level of money, not safely at some high-abstraction level. You can’t afford to have the passive, disinterested (or even slightly contemptuous) attitude towards money paycheck people often have. If you don’t develop what I call a “money-positive” attitude, you risk both failing to make money, and developing unhealthy and fearful attitudes towards it. Just as, if you’re an employee, if you don’t get past disinterest and contempt and develop some curiosity about management, and a “management-positive” attitude, you’ll fail to advance. You’ll be reduced to seeking solace in Dilbert cartoons.

So you can’t treat money as a spectator sport. You have to develop a genuine, intellectual curiosity about money that goes beyond your personal needs.

But I don’t mean the kind of interest that bankers and investors have. I mean the sort of interest detectives and forensic accountants bring to their work. Like them, you can follow the money as a source of personal economic intelligence to guide your gig economy activities.

Following the money means understanding money the way you understand the weather and climate.

The weather is the low-level details of transactional flows, while the climate is high-level macroeconomic shifts. Each by itself can be misleading, but together, they can help you follow the money.

Let me illustrate with myself as an example.

Money Weather, 2011-21

If you’re primarily used to getting money via direct deposit, and spending it via checks and credit cards, with things like PayPal and Venmo being “play money” on the side, the transactional complexity of the open economy can come as a shock to you. It’s as different from the paycheck money-flow world as outdoor weather is from indoor weather (to continue our parallel, management activities inside companies are like indoor weather control — adjusting the HVAC system and so on).

One of the most interesting ways to develop intuitions about following the money is to pay attention to how you’re paid at the level of transactional details, learning why things work the way they do in different industries, and developing preferences for being paid in certain ways. It’s like picking the sort of weather that suits your temperament.

Early on, you should aim to get paid in as many different ways as possible, so you learn about weather patterns and develop a sense of how they might be shifting. And you should always be willing to experiment being paid in a new way, unless it looks illegal or scammy.

Tracking how you are paid is to money what going outside and looking at the sky is to the weather. It reveals a lot about the client, the industry, and the local economic culture. Tell me how you are paid, and I’ll have some pretty good guesses about what sort of gig-work you do, and in what part of the economy. You probably can guess better than you think as well.

See if you can infer the “story” behind my history of payments below.

The first time I got paid, it was via paper check. I was paid mostly with paper checks for the first couple of years (and conscientiously saved the paper stubs like they were trophies). At some point, I got paid against a “purchase order” (PO) for the first time. And also got paid late via an invoice that somehow got “lost” for the first time.

At some point, most clients started paying via credit card. Even though I was set up to receive credit card payments from the beginning, it only became popular a few years in, reflecting changes in the infrastructure, environment, and who I was working for.

At some point, wire transfers started becoming more common, initially for international clients (and I had to get used to SWIFT codes), and then domestic. Sometime around 2013-14, payment via services like bill.com started becoming common.

For a gig in 2017, I was supposed to be paid in crypto tokens, but the company kinda “forgot” and since it was a small amount I didn’t bother pursuing it. I think that was also the year I received a paper check for the last time.

One big company I have worked with for the last 4 years has a really solid and futuristic self-serve automated model for dealing with POs and payments that I genuinely love. Once I year I do a big invoice with them, and immediately get an email from a partner firm called C2FO, offering immediate payment (instead of in 60 days) in exchange for a small discount that they calculate based on current economic conditions. It feels very futuristic. I’ve never had to avail myself of the discounted early payment offer, but it’s nice to know it’s there. It’s like high-end payday loans (and unlike payday loans the rates are reasonable). More such mechanisms are coming online.

One time, I was paid for an hour of consulting with… a pair of shoes.

This year, for the first time, I am accepting part-payment in stock options for a gig. It’s not an uncommon thing to be offered, but it is uncommon for the offer to be worth the trouble to accept.

I’ve paid a lot of my own subcontractors via PayPal, but can’t recall an instance of accepting money via PayPal. I feel that makes me part of the gig-economy middle class. PayPal has become something of the working-class transaction layer. It’s fine for occasional gig-economy dabblers, but a PITA for full-timers. Real indies use Freshbooks and integrate with Stripe. Using PayPal marks you as not quite serious.

Stripe has been a huge game changer in the plumbing of the middle-class free-agent world. It set up a whole parallel universe of financial plumbing, and a big chunk of my consulting income, and all my non-consulting income began flowing through it at some point.

Stripe and Paypal now also offers loans against cash flow analytics, without the bureaucracy associated with getting lines of credit at traditional banks, or the high interest rates of credit cards.

I never noticed it while it was happening, but the landscape of financial flows has shifted slowly but decisively under my feet, to become more automated, more electronic, more seamlessly international, and with much better risk and credit management. And at all scales from POs worth tens of thousands of dollars, to small transactions on the order of $5. Even for solo free agents, the cost of capital has come down sharply, though I’ve never needed it (nothing I’ve attempted to do so far has required any capital outlay bigger than the cost of a computer).

It’s almost like when I started out, it was in a primitive financial wilderness, and now it’s a well-paved urban built environment. In part, I’ve moved to a better corner of the economy. In part, the economic environment has changed.

Why is it important to pay attention to these things? Because often you get early warning about where things are headed based on these low-level details.

And often, the mechanics of transacting with a company can give you clues about its economic destiny (if you’re curious about why, look up Coasean economics). In 2021, you should be eager to work with companies that pay you in sophisticated, low-friction ways, and be wary of ones that involve a complex exchange of physical paperwork and end up mailing you a paper check. Following the money means following lower transaction costs.

Can you tell from the details above what the higher-level story of my money-making evolved? It’s like tracking someone through the woods based on footprints.

Money Climate, 2011-15

If the transactional environment is the weather, the macro-environment is the climate. To follow the money thoughtfully, you must pay attention to both.

In 2011, when I went free agent, the world economy was just beginning to limp out of the global financial crisis (GFC). At least in the United States, money was not yet flowing freely through the economy. Corporate budgets were still tight, with restrictions in place. In 2011, it seemed obvious that despite the “recovery,” the GFC had changed the world in very significant ways.

Banks had just been bailed out, and the economy was getting used to weird new phenomena like “quantitative easing” distorting the money supply in ways people were still not used to.

Silicon Valley had only recently started recovering from the effects of the dotcom crash a decade earlier, with a new wave of “2.0” companies that was yet to demonstrate viability. People were wondering: would it create another bubble and crash, or was this a more sustainable arrival?

I asked myself: Where is the money?

Specifically, the discretionary, liquid money that was not already spoken for, and might be available for me? The answer I came up with was:

1. Governments had money

2. Banks had money

3. A few big old companies had money

4. Silicon Valley had money

5. Ordinary individuals had some money

Straight off, I decided I was never going after government money via things like grants. Governments always have money, but it is always painfully hard to get at any of it. And it always comes with vast amounts of baggage, but few interesting risks you can meaningfully participate in. I might be willing to jump through a few hoops for a government gig at unique places like say NASA, but that’s it.

I also decided I was not going to go after individuals (via business models like personal coaching). As an established blogger, I had an advantage in reaching ordinary individuals, but “consumer consulting” was not really a meaningful idea in 2011. Neither the infrastructure, nor a culture of individuals paying individuals in their private capacity for consulting-like services, really existed back then.

There was no “direct to consumer” market in consulting, so to speak (this would change). Consulting was something you sold primarily to businesses above a certain size.

That narrowed things a little. I was after open-market, private sector money. But that was still too broad. I also decided that while I would be open to old economy and financial sector money, I would not pursue it.

That left Silicon Valley, or “tech money.”

I’ve been associated with the scene for a long time now, and am generally considered a “tech insider,” so this might seem weird, but in 2011, coming from the East Coast, this was not an obvious move. As a mechanical/aerospace engineer by training who had worked at Xerox, it was by no means the obvious conclusion that I should head towards the tech scene on the West Coast and try to find a foothold there. I was already 36 at that point, so not exactly young.

But in 2011, it seemed obvious that software was going to eat the world, and that the tech economy was slowly going to turn into the whole economy.

It was equally obvious that old economy companies were either going to go into decline-and-harvest mode, or into fraught “digital transition” attempts, most of which would fail.

Which meant, whether or not I had anything to offer, I had to position myself primarily in relation to Silicon Valley. That’s what following the money meant in 2011.

I did it physically. First we moved from Washington, DC to Las Vegas in the summer of 2011, and then from Las Vegas to Seattle (aka Silicon Valley North Annex) in 2012, after briefly considering and rejecting the Bay Area proper.

My bet paid off. Being located on the West Coast put me right next to the biggest, most free-flowing rivers of money in the world at the time. I began getting and closing more leads, mostly from tech companies, though not necessary on the West Coast — people from everywhere involved in tech tended to pass through all West Coast cities frequently back then. If you think of potential clients with money to spend as walking around with dollar signs on their foreheads, in 2011-15, they were all constantly passing through Seattle and the Bay Area (Portland and Los Angeles developed as significant tech hubs a little later).

I also learned a few things:

1. Startups were eager for consulting help but had little to no money

2. Growth-stage companies had money but were generally not operationally set up to handle consultants outside of very specific, targeted “special ops” needs

3. Large tech companies generally had anti-consultant cultures, unlike large East Coast old economy companies.

4. Investors had money, and were open to spending it on consultants

It took a couple of years, but I eventually developed enough of a strong network (see my previous newsletter) that I was able to plug in to the money flows of the tech economy fairly reliably, if not predictably. By 2014, I had worked for small startups, medium startups, large companies, and investors.

I was inside the tech scene, and perhaps more importantly, seen as being inside the tech scene. I had followed the money to its source.

Money Climate, 2015-20

Sometime around late 2014, I sensed a disturbance in the force. Flows of money were beginning to shift around me… again. Specifically:

1. Private equity (PE) money was becoming a bigger deal in tech

2. High-Net-Worth Individual (HNWI) and “family office” money was growing fast

3. The big platform companies were starting to behave like old companies

4. Investment money was pooling at the extremes — seed money, or growth money, with the middle slowly starving

5. Money was starting to seriously flow into climate and sustainability tech

6. Software was eating healthcare and bioscience, creating another large flow of money to follow

7. Money outside of Silicon Valley wanted to be like money inside Silicon Valley

8. Ordinary individuals had money and there was growing infrastructure to get at it

While I didn’t specifically try to follow these shifts in an explicit way, I began to keep an eye on them and staying informed, and saying yes and no to gigs in ways that reinforced my exposure to flows I wanted to drift with.

Often, the biggest source of intelligence was the mix of leads I was getting, whether or not they turned into gigs. After factoring out the effects of my own evolution, the rest was priceless intelligence about the economy.

Towards the end of 2015, I began consciously following the evolution of the sustainability and energy sectors, and thanks to a couple of new gigs, was able to start following that trail. To a lesser extent, I began following money in healthcare, and landed a few gigs in healthcare tech as well. That’s on the back-burner for now, but I might pursue it more actively in the future as it gets more interesting and moneyed.

Today, I say yes to tech gigs only if they are technologically interesting, and trying to push computing frontiers in somewhat fundamental ways. I no longer like gigs that simply run known Silicon Valley playbooks against new opportunities, or push existing technologies in incremental ways. I’m more likely to say yes to climate and energy gigs — that’s a big flow of money that’s only getting bigger with every passing year, but the sector also interests me because it is doing some of the most technologically interesting work happening today.

I used to be wary of PE money, and would often treat PE-funded status as a red flag in leads, but have grown increasingly comfortable with it. There’s PE and there’s PE. There’s the vultures, and there’s the bold turnaround operations. Some of the most interesting things these days happen neither at public companies or venture-funded companies, but at PE-funded companies.

And boundaries between PE, VC, and ordinary corporate money have started to blur anyway.

Money Climate Change, 2021-31

In the next decade, once again I sense vast shifts in the offing at both the weather (transactional) and climate (macrotrend) levels.

As I mentioned earlier, this year, for the first time, I accepted part payment in stock options for a gig (generally a bad idea — if they’re offering equity participation to consultants, it is unlikely to be a good startup).

One of my clients just IPOed via a SPAC.

One of my larger clients last year was some strange hybrid of a VC firm, PE firm, and family office.

The world’s financial hydraulics are changing yet again, as they do every decade or so. Never a dull moment when you live in the open economy.

The post-Covid economy is going to be… weird. In ways I can’t yet see. I feel like a beginner again, as should you.

The West Coast is also going through some sort of cyclical maturation late stage. “Tech” is getting dispersed around the globe, so it is harder to see what it means to “follow” the tech money. Life was simpler when you could simply physically move to where the action was. On the other hand, online pathways have become much better. Media like Twitter and now Clubhouse offer ways to “follow the money” virtually. In 2011-15, the “VC blogosphere” was a big deal, but that’s pretty much dead now.

The “Direct to Consumer” market, which in 2011 I dismissed as not a real thing, has finally emerged. With Stripe, and the “creator stack” of the “passion economy,” you can now sell things that look and feel kinda like consulting directly to consumers (or employees acting in their private capacity, with or without corporate reimbursement). This newsletter, arguably, is me selling consulting in an aggregated way to individuals, in a form factor that would have been highly inefficient 10 years ago. Depending on what you teach, online courses can be a form of consulting.

The cryptoeconomy also shows signs of maturing, and evolving from primarily an investment sector to a transactional sector. Expect to get paid in usable tokens in the next few years, and it being not such a weird thing.

Will I have to pack up and move physically once again, following the money? I will almost certainly not stick around in Los Angeles more than a few years. But where to next?

I don’t yet know. But this time, it will only partly be about following the money.

As I’ve grown somewhat more financially secure, I now have some freedom to solve for things besides money. That could of course change in an instant. All it takes is a few bad quarters, a major economic crisis, and some bad luck to go from feeling like you’re in a secure position to feeling like the world has collapsed around you. It’s happened before in my lifetime, and it will happen again. You think you understand the weather and climate, and then get blindsided like Texans did last week.

There is no permanent security to be found in the money layer of the world, but there’s always interestingness, and a general curiosity about money — but short of obsessive maximizing tendencies — tends to pay off. It’s part of our world, and it’s an interesting thing that rewards study both intellectually and by flowing towards you.

Money flows are never still. While ancient rivers of money always keep flowing robustly, they do change course slightly. But new rivers of money are always emerging, and fragile ones drying up. And the nature of money keeps changing.

In absolute terms, the oldest rivers tend to contain the most money by volume, but also the least money in terms of accessibility. Money in ancient rivers tends to be very stable and spoken for, and requires a lot of work to access. Money in newer rivers is easier to access, but is also liable to shift suddenly on you, so you have to stay on your toes.

Following the money has been quite the ride for the last decade. I expect it to be even more of a ride for the next decade.

Last week, I kicked off my 4-part series to mark my tenth anniversary as an indie consultant with a look at the past and future of my workflows at the inbox level.

Workflows are the lowest layer of the consulting stack. The level at which Fingerspitzengehfühl (“finger-tips feeling”) operates. I like to think of workflows as the embodiment of your trust in yourself. Intra-personal trust if you like. In this second part, I want to take a similar ±10 years look at trust between you and others, or interpersonal trust. For indie consultants, this is primarily trust between you and clients. This is the second layer of the stack.

How Trust Actually Works

Indie consultants tend to be highly conceptual people. So we tend to model interpersonal trust in ways that are too abstract, like game theory (prisoner’s dilemma anyone?), crypto-like “proof of work,” or “trust signaling” through devices like a clear personal manifesto on a website, a list of values, or a curated bunch of gushing testimonials speaking to the virtues of a fictionalized version of yourself.

If you go down that road, the risk is not that you will fail to build trust, but that you will succeed at building a sort of ersatz, dehumanizing “artificial trust machine” that “works” in the sense of making money, but turns you into an increasingly commoditized and packaged offering. At best you will turn into a “trusted personal brand” within a clearly circumscribed market niche, rather than a trustworthy person living and working in a world of other humans.

What’s the difference?

• A trusted personal brand represents a clearly specified and bounded promise, and a demonstrable record of delivering against it consistently. A trusted personal brand lowers risk on some close-ended front.

• A trustworthy person it is worth trusting — somebody it is interesting to take risks with in an open-ended way. They increase your capacity for risk, and win or lose, you will be left feeling enriched rather than betrayed.

Not that there’s anything wrong with wanting to be a trusted personal brand. If that’s what you want, by all means go for it. If you play it right, and get a little bit lucky, you’ll make more money in a year than I have in ten, and move on from this level of the game entirely.

But the deeper reward of being an indie consultant is the chance to forge yourself into a trustworthy person in a fully human sense — but on a larger scale than most humans will ever enjoy. Everybody has a circle of coworkers, friends and family within which they are viewed as trustworthy or not. Indie consultants have a shot at a more public sort of trustworthiness in the open economy that goes beyond such local, personal circles.

This trustworthiness is condition that magically leads random distant strangers to reach out to you, and take on risky, uncertain challenges based in part on your support and promise of fellowship.

I like to think of it as projecting “spooky trustworthiness at a distance.” It’s my substitute for sales and marketing.

The “distance” of course, is distance on a social graph. Like between dwarves and elves in Middle Earth.

When it works, spooky trustworthiness at a distance opens up a world of optionality for you, where epic adventures can be had. Adventures where you won’t be the hero or heroine, but the shadow of fascinating heroes and heroines. What I’ve been calling shadows’ journeys in previous posts.

This requires an approach to trust that may feel awkward and unfamiliar at first.

Spooky trustworthiness at a distance rests on an individualized, anthropological understanding of how your actual gigs actually come about — or fail to. Trust, in other words, lies in the truths contained in a collection of stories that you start building with your very first client. It eventually turns into a sort of personal ethnography, or thick description, of the interpersonal dynamics triggered by your visible, available presence in the world of work. You are supply. The story of demand for you is a story about trust.

In my case, I can identify a sort of three-act arc in the ten-year story.

Act 1: Trust Ramp-Up

Here’s a quick tour of how I ramped up with the first few clients, and how trust developed in each case:

1. In February 2011, I got my first two clients off of Quora. Strangers who decided to trust me on the basis of my answers to questions on a public site. These were sparring gigs. The amounts were small, but the confidence boost was huge (thanks Gene and Mat!)

2. I got my third client in June 2011 via friends at a PR firm I had hired for a project at the job I had just left behind. It was a medium-sized strategic marketing writing gig. Though I got along fine with the client and was paid directly by them, the trust equation never really extended past my friends. It was a subcontract pretending to be a contract.

3. In early 2012, I landed my first big gig, my fourth client, for an analyst report project. It came via a reader of some of my enterprise software blogging (back in 2009-12, I was briefly blogging for the Enterprise 2.0 blog). It did not go well, due to misaligned expectations that didn’t become clear until the eleventh hour.

4. My fifth client — who I still work with, and is now my oldest client — cold-approached me in 2012 on the strength of my Gervais Principle series of blog posts. I’ve now worked with him across four senior executive roles at different companies, and I first developed 80% of my bag of tricks working with him.

The interesting thing is, at the time (2011-12) I could not easily tell what was working. But it was quickly clear what didn’t work well — my unhappy fourth gig taught me that initial trust must be converted to working trust by getting expectations aligned and crystal clear early on. But not through painful and structured conversations seeking “alignment” or clarifying “expectations.” That’s a waterfall approach to trust that basically never works because you just don’t know each other well, and end up making ritual noises. Instead, you do it by iteratively setting and delivering on small, bite-sized goals that get larger and larger.

Alignment and expectations are not things you define at each other, but things you learn about each other iteratively, possibly adapting and compromising along the way.

If all trust in a gig is actually “trust debt” linked to a big, uncertain deliverable outcome, you’re setting yourself up for trouble. Do not mistake a pleasant, collegial relationship for working trust.

Working trust is primarily a learned, shared, and genuinely felt confidence in the mutual acceptability of future work output before it is delivered.

This is a weird definition of trust — and one that I’m writing down for the first time, though I’ve operated by it for ten years. So what I learned in Act 1 is that there’s actually 3 elements to trust, with working trust being the most important:

1. Discovery trust: you trust the pathway that catalyzed the relationship, whether it is a chain of referrals, or a social object like a blog post. It is tempting to rely on credentials for this, but that doesn’t work. Credentials are filter criteria, not trust criteria.

2. Commitment trust: you establish enough 1:1 rapport to sign a contract that you feel good about, without too much scrutiny or a lingering sense that you might potentially get screwed over.

3. Working trust: you learn to trust each other according to expectations that have been aligned by iteratively learning about each other early on.

In Act 1, I experienced four kinds of discovery trust across five clients in two years (trust via mediated readership, trust via referral, trust via subcontracting, and trust via direct readership).

Commitment trust was always the same — the contract only got signed after I met in-person with the client and had a chance to establish rapport. That’s all it was — a test for a kind of shallow capacity for simply getting along during a low-stakes meeting.

Here is a contrarian opinion: it’s not worth getting too clever or careful with contracts. If you find yourself doing that, you’re attracting the wrong kinds of clients and losing at the game of becoming a trustworthy person. Most of the real risks in interesting gigs cannot be captured in contracts no matter how clever you get.

Early on, I just made up my own one-page contract and have used it for the majority of my gigs. When the client wants to use their own contract for whatever reason, I give it a quick once-over for typos and obvious mistakes, and just sign. If I find myself hesitating or wanting to argue minutiae, I back out. You cannot fix in the contract what is missing in the commitment trust level.

Working trust was the hardest to learn. The first year convinced me to avoid “working trust debt” (it’s like technical debt in software), and instead build working trust early and aggressively — in my case by specializing in what I call a sparring approach to consulting. This is of course not always possible. Many types of consulting are built around big deliverables and a lot of back-loaded risk. You have to figure out your own approach to mitigating that.

Act 2: Track Record

After those first five clients, I settled into a pattern. I had a non-empty track record, and always had 1-2 active clients going, even if billings were at a trickle. Though nobody has ever asked for references to past clients, the fact that they exist and are credibly listed on my website seems to make a big difference, both in clients’ ability to trust me, and in my own confidence in how I present myself. A track record is not really about the verifiable list of gigs you point to. It is about the confidence you project and inspire due to that list existing.

My slowly growing ability to do this kicked off, somewhere in early 2013, a second act in my adventures with trust.

The fact that I was mentioning a consulting practice in my writing and talks without sounding apologetic, or like I was faking it, and clearly not starving on the sidewalk, seemed to create the beginnings of an aura of trustworthiness.

Starting around 2013, almost all my clients came via my own blog: direct, inbound leads. The majority — perhaps 70% — tended to reference the Gervais Principle as their reason for reaching out to me. A few came via a couple of other lightning-rod type bits of writing. Interestingly, almost none of my leads came from my few attempts to write “content marketing” type lead-gen content.

Referrals, which accounted for 2 of my first 5 gigs (and probably more than 60% of my revenue over that period) became vanishingly rare, and stayed that way. I’d say they now track at around 1% of leads, and maybe 5% of closes. This was very surprising to me in the early years. I’d expected referrals to play a bigger role, and even made some half-hearted efforts to catalyze them. But apparently, the kind of trustworthiness I operate with is not very transitive.

Act 2 lasted perhaps 3 years. In terms of the three kinds of trust:

1. Discovery trust: was increasingly being established by my own visible online presence, mainly my writing, but speaking gigs played a small but crucial role. I was real! There was video evidence! I was not a dog on the internet!

2. Commitment trust: remained the same — the in-person rapport meeting remained key to establishing it. I’ve never had to change the approach I adopted in Year 1.

3. Working trust: increasingly I was only doing sparring work, which besides many other benefits, has a sort of pay-as-you-go trust learning structure. There is never any trust debt, and no nasty surprises lurk in distant deliverables. I’m only as trustworthy as my last sparring session.

Along the way in Act 2, in 2014, I did a year-long stint with Andreessen-Horowitz, a gig I think of as a charismatic megagig that significantly reshaped trust perceptions for me.

Charismatic megagigs are are important, and you should try and land a couple. They are what turn a strong but commodity track record into a differentiated one that marks you as the only person who can do certain things. I think I have 3 such on my record, though only one has a significant public aspect.

It proved to be an interesting milestone, since it added a sudden sharp spike of glamour and visibility, and added some high-visibility narrative color to how and why I was trusted, and by whom.

This actually had one significant downside, as I started getting a bunch of low-quality leads from second-rate entrepreneurs hoping for introductions into elite Silicon Valley circles in the guise of a consulting engagement. In many cases, it was openly crude overtures that assumed I was in the influence-peddling business (I’ve never accepted money or gifts to make introductions, and have never made an introduction that I didn’t actually think had potential).

But the upside of the gig (besides the Breaking Smart workshop I spun out of it) was that it triggered a shift to Act 3, where I was not just a track record from nowhere. I could be located with respect to economic scene landmarks — I was a guy with a track record in the tech scene. I was part of the software-eating-the-world bigger story, if only as an extra.

This is important. Nobody is every trusted or trustworthy in isolation. You are trusted against a larger backdrop or scene. Your fortunes rise and fall with that scene. You can have a reputation that is hedged across multiple scenes, but you can’t be a “trusted guy from nowhere in particular.” I’ve seen changes in how new connections react to me based on how the reputation of Silicon Valley and tech have changed over the years. If the reputation of the tech scene ever takes a terminal nosedive, I’ll probably go down with it.

This is neither good or bad. It’s just the way it is. Stick around long enough, and you’ll be part of both the hero and villain sides of every story you’re in.

Act 3: Part of the Scenery

After 2016 or so, things got a bit… diffuse. I could tell from the way leads led to gigs that it wasn’t really about track record anymore. Somehow, mere visible survival, general approachability, and avoiding the allure of packaged, branded self-presentation seemed to have done the trick of making me look “established.”

It feels kinda like being a human bus stop in a city. People who traveled certain routes in certain scenes were simply aware of my existence because I was a visible part of the landscape in those scenes. This can feel a bit strange — you end up being at once seen and not-seen.

One result of this is that gigs these days feel less like the result of mechanical effects or numbers games, and more like little vignettes in a big story where I have a small role. Vignettes that could be footnotes in a sufficiently voluminous business/economic history. The logic has gone from statistical to narrative.

In Act 3, the three aspects of trust start to work differently in some sort of mature mode:

1. Discovery trust: This works via simple known presence. You’ve been around long enough, and the world is small enough, that enough people already know who you are. You’re part of the scenery that’s their mental model of a scene. You don’t need to be “discovered” by the local economy any more unless you want to venture into new domains or geographies because you’re bored (which I suppose might happen to me some day).

2. Commitment trust: This still hasn’t changed. It’s still about meeting face-to-face (on video is okay, but not ideal) and establishing rapport, and signing a contract you don’t have to think too hard about.

3. Working trust: This has again broadened somewhat beyond sparring work. I now am more willing to take on more complex kinds of work, including calibrated amounts of “trust debt,” but only with people I’ve established baseline working trust around something simpler like sparring or a quick workshop.

So that’s where I am now, in the middle of the third act of a 3-act story of evolving ability to trust and be trusted by real people, while remaining an actual person rather than a brand. How does this act end? How many more acts remain? I don’t know but I can speculate.

The Future of Trust

Looking ahead, I can see some interesting new challenges already emerging. Some are a result of personal things — in the next 10 years I’ll go from 46 to 56 years old. When I started, most of my clients were my age or older. Increasingly, most of my clients are younger than me. In rare cases a full two decades younger.

I can see clear signs of a looming trust problem I haven’t had to deal with so far — simply being out of touch with the world my clients live in (feels weird to think some of my future clients may be in kindergarten right now).

This isn’t an academic problem. Already, I’ve found myself saying no to potential clients who are clearly looking for some sort of paid elder mentoring rather than the kind of consulting I am comfortable providing.

I’ll cross that bridge when it becomes impossible to avoid crossing it.

A slightly different trend is also shaping my anticipation of trust trends. The Great Weirding has left the business world in a very altered shape. The Culture War has reshaped the landscape of trust. Tribalism is an actual factor now, in how consulting works. Increasingly, to access some space of gigs, you first have to gain membership into some sort of tribe that controls access to that space. I don’t like that, and avoid that kind of space, but it may become harder and harder to do so.

Trust works differently now in subtle ways I’m still trying to make sense of. Spooky trustworthiness at a distance is getting spookier. I have a feeling only half of what I think I know about trust will remain true in 2030. The challenge will be figuring out which half to keep, and which half to toss.

My ten-year anniversary as an indie consultant is coming up. On March 1, it will have been exactly 10 years since I quit my last job. It’s the longest I’ve ever been in any life situation as an adult. So I’ve decided to devote the next 4 issues of this newsletter to systematic reflection on the last 10 years, and to looking out at the next 10 years.

Let’s start on the base layer of the working life for everybody, whether in a job or an independent: workflows.

In this issue, I’m going to share a look back at how my workflow, more specifically my email inbox, has evolved over the last ten years since I quit my job. And look forward to how it might evolve in the next ten years.

This is a tale of 7 inbox conditions, marking a journey from my past workflows to my aspirational future workflows. Specifically, I want to take an inventory of the changing mental state induced by hitting Inbox Zero over the years (for the Gen Z among you, Inbox Zero is an idea most associated with David Allen’s famous GTD productivity system).

In theory, hitting Inbox Zero is supposed to make you feel mentally free, so it is an ideal best-case sampling point for your situation. How you feel when you hit Inbox Zero should reveal how free you really are.

Inbox Kinda-Free

This time, ten years ago, I had a job I had just decided to quit, leading R&D projects at Xerox.

In a job, once you’re above entry level, you’re typically on many email distribution lists. You are typically included in dozens of communication loops, whether or not you have any actionable responsibilities within them. You are expected to generally know what’s going on if you think you have — and want — a future in the company.

You have a manager and colleagues who expect specific things from you, but you’re also part of a larger corporate community that expects some general involvement from you, and gets generally involved with you in return. How you manage your involvement beyond immediate expectations is a function of your email game.

Back then, I used to be pretty disciplined about Inbox Zero.

In 2011, getting to Inbox Zero periodically with my work email, and enjoying a modest afternoon of clear-headedness every couple of weeks, was how I knew I was on top of things and at the right level of involvement with the corporate hive mind.

In the GTD philosophy, Inbox Zero is shorthand for the visceral experience of freedom. What I didn’t know then was that I hadn’t really experienced the intoxication of true Inbox Zero. Only a sort of low-alcohol-content ersatz version. As I now know, you cannot actually experience Inbox Zero at a job.

See, the thing is, at a job, your email is part of this river-like flow of the inner life of a business. Even if you happen to have nothing to do on a specific day, and are drifting between projects or bosses, you have an immersive situation awareness that you cannot turn off. Not even if you clear your inbox.

A nonzero fraction of your attention is locked up in the internal corporate stream of consciousness. Seeing, and being seen, in an open-ended way, within a shared situation awareness field, is how jobs work.

This is part of the definition of a full-time job — you commit to a mutual attention lock within the internal corporate stream of consciousness of an organization.

So even if you happen to achieve Inbox Zero at a job, in a decent-sized organization, your head never gets completely clear, because in a sense it’s not entirely your head to clear.

Inbox Zero amounts to Inbox Kinda-Free.

Your mind is not entirely your own to clear as you see fit. Other people have a certain right to peek into it and dump ambiguous things into it, generally via email (and these days via Slack and other media). A part of your head is devoted to, for want of a better term, “holding state” for the organization as a whole.

So you’re never quite free of and clear of the attention lock. Even if you hit Inbox Zero nominally, a part of your mind is always still “at work,” sharing in whatever sentiment superstate prevails in the organization at the time.

Inbox Void

On March 1, 2011, the day I left Xerox, that attention lock snapped free. And Inbox Kinda-Free turned into Inbox Void: the kind of emptiness it is terrifying to look into.

I no longer had my Xerox email account, and my Gmail was a desert.

Clearing it was trivial. But the clear state that resulted was not the Inbox Zero ideal of freedom. It wasn’t even kinda-free. Instead, it was a stark, oppressive emptiness that reminded me that I was not free. I was merely unemployed, and now newly burdened with figuring out how to make a living. My time wasn’t my own, but beholden to dollars I hadn’t yet figured out how to make, and clients I hadn’t yet landed.

Nobody needed me by default. It was no longer anybody’s job to check in on me and make sure I had enough to do. Or that I was getting paid enough to remain happy and productive.

The empty inbox was not a sign that I was on top of things, but a sign that I had nothing to get on top of, and that it was not actually a good state.

I didn’t need Inbox Zero. Inbox Zero was bad. I needed Inbox Busy. I needed a healthy flow of leads, inquiries, promising conversations for gigs, requests from clients, and so on. And I didn’t have it.

It took me perhaps another two years to get to there.

The interim was constantly stressful. The inbox would keep going to zero, with nothing to do, no leads to pursue, no obvious money-making options to simply exercise.

And there was no background stream of activity I could feel part of, to occupy my attention. At my job, even if I cleared my inbox on Sunday afternoon, I’d get up on Monday morning and face an inbox full of stuff to track, even if I was on top of my own stuff. It was like Twitter. The feed was always moving.

Early on, as an indie, I’d often clear my inbox, and it would stay clear of “work” email for days and sometimes weeks on end (not counting alerts, newsletters and personal email). Oppressively, stubbornly at zero even as the savings level slowly went down.

I’ll call this Inbox Void. A stressful kind of Inbox Zero that you don’t actually want. An empty state that oppresses rather than liberates, and can kill you if it persists long enough.

Inbox Anxious

It was probably sometime in late 2012, almost two years later, that for the very first time as an indie, getting to Inbox Zero became a non-trivial task again.

There was finally a there there to my consulting life. Enough going on in my email that getting to Inbox Zero meant doing some actual work. I had moved from Inbox Void to Inbox Anxious — activity tinged with ever-present financial uncertainty.

Multiple conversations were actually going places, email exchanges that could be called “work” were happening, contracts and NDAs were being sent back and forth. Hours were being billed, invoices were being sent out and paid (or not), context was being switched between clients.

I don’t remember the first time I had to handle two back-to-back meetings with different clients on the same day, and switch context on a dime, but at some point I noticed I was doing that sort of thing.

And suddenly it hit me: I’d gone from mostly faking it to kinda making it.

My indie consulting life felt real for the first time. It happened quickly, but not quickly enough that I noticed a sharp boundary. It wasn’t like a sudden switch being flipped.

But there was something new here. Unlike at a job, getting on top of consulting commitments and deliverables temporarily, and getting to Inbox Zero, felt different. Unlike at a job, there was no generalized background stream of corporate consciousness that would reassert itself and expand to occupy my mind via an attention lock.

This was a true zero. Once I got on top of things I owed clients, it was a kind of clear headspace with no background collective stream of consciousness at all. No attention lock within a hive mind.

But for the first few months, this state was fleeting and unstable. Impossible to sustain for more than a few minutes.

The thing is, even though there was no background stream of corporate consciousness to sink into, there was still the anxiety of insufficient gigflow, and too few leads turning into closed deals and signed contracts. Every time I hit send on the last thing I owed a client, and cleared the decks, the mild-to-medium anxiety (depending on cash runway) would flood right back in. And instead of enjoying “freedom,” I’d be thinking about how to drum up more work, or brainstorming other income streams.

This was what I call Inbox Anxious. Inbox Zero where the commitments have been cleared, but the anxiety has not, because you still haven’t acquired confidence in your ability to keep the gigs flowing. It’s better than Inbox Void, but hardly freedom.

You still haven’t learned to manage the stress of not knowing where your next billable hour will come from, or acquired the confidence that it will come, even if you don’t know from where. Part of you still itches to have a sure-fire plan for the next month’s rent. You haven’t yet shaken off the addiction to a predictable paycheck, to being needed-by-default by some large corporate consciousness.

Inbox Busy

Around late 2013 though, things began getting consistently busy enough, and I began trusting enough in things working out, that a new kind of Inbox Zero headspace became accessible.

I could turn around everything I owed clients, and I’d be in this intoxicating kind of clear headspace where I could feel really free. There was a real, reliable stream of ongoing activity to get away from — Inbox Busy — and I could actually meaningfully get away from it. Taking a busy inbox to zero meant actually being free rather than vaguely anxious.

Free of deliverables or paperwork I owed clients.

Free of background corporate streams of consciousness.

Free of immediate cash-flow anxieties.

It helped that my average savings level — or runway length — had slowly crept up over two years. The more runway you have, the more you can actually enjoy Inbox Zero when you get to it.

Initially, this kind of headspace was pretty rare. Maybe one afternoon every few months. Then I’d go through periods where I could hit that mood for an afternoon or so every week.

Those were fun times, but they didn’t last.

Between 2014 and 2017 or so, I suppose I went through some sort of consultant-market fit threshold, and almost without realizing it, landed in a condition where I typically had multiple active gigs going at any given time (right now I have 5 active gigs and 3 on the back burner), and getting to Inbox Zero started getting rarer and harder than it had been in my old job.

I had gone past being busy enough to being too busy (which is not the same thing as making too much money). I’d landed in the regime I’m in now: Inbox Chaos.

Inbox Chaos

In a single company, the corporate stream of consciousness has a sort of harmonized flow to it, so you can generally stabilize and zero-out all your active threads at once. And when you do, there is something it is like to simply be immersed in the corporate stream of consciousness. It has a direction and purpose, and an ongoing story that makes sense. For me, at Xerox, on afternoons I got to Inbox Zero, I’d land in a sort of generic Xerox headspace. I’d check in on other projects, chat with colleagues, catch up on intranet news, and generally partake of the Borg’s mind-state (or more technically, the egregore mind-state).

When dealing with multiple clients operating on very different tempos within unrelated stories, with corporate streams of consciousness in different moods, it is much harder to wrangle them all down to zero at the same time.

And when you do manage it, while you don’t have a single corporate stream of consciousness filling your head, you have this sense of being in the eye of a chaotic storm.

The thing is, the economy is a wild place, and once you’re plugged in enough to the wilderness directly via multiple varied connections, there is a sense in which you’re now immersed in the stream of consciousness of the economy as a whole.

The larger gestalt of macro forces and trends starts to seep into your consciousness. It’s not just the news. You’re not a spectator or an analyst writing trend reports from the comfort of a Gartner office. You embody the health of an economy, in the sense an indicator species embodies the health of an ecosystem.

But unlike a corporate (or even sectoral) stream of consciousness, there is nothing it is like to be in the general macroeconomic stream of consciousness. The economy, unlike a single corporation, is not an egregore or Borg-mind. There is no mind directing the invisible hand.

While more diffuse and incoherent, and more resistant to anthropocentric identification, this stream of macroeconomic consciousness is ultimately far more powerful than that inside any single company. Once you get sensitive to it, and open your mind to it, it will start to colonize your mind, unless you do something to stop it.

Sometime around 2017 I noticed that this was exactly what I was doing. I had almost unconsciously started cashing out some of the freedom of Inbox Zero moments (turned into hours and days), with the chaos held temporarily at bay, by indulging in several “freedom projects” of my own.

And that had workflow implications.

For example, I realized that I liked to save mornings for writing, and that I did not enjoy having to work on two different gigs on the same day. Back-to-back meetings with multiple clients, previously a sign of having made it, and a sort of badge of honor, now began to seem annoying and exhausting.

Almost without planning it, I started doing active load balancing, batch processing, and time management to create and maintain conditions favoring more frequent and extended Inbox Zero headspace. Hilariously enough, this was the reason I quit my job in the first place — to be able to do that. It just took me ten years after quitting to actually get there.

I was starting to identify and wall off small, fragile islands of actual freedom that I could inhabit during the more stable periods of Inbox Zero, protected from the chaos.

I began saying no more often to potential clients whose needs didn’t fit the workflow rhythms I wanted to create, preserve and protect. I began setting expectations with clients that created room for my own activities. I no longer promised aggressive turnarounds that would disrupt my own routines. Protecting islands of true freedom on my calendar began to seem more important than maximizing billable hours.

It wasn’t that I was making more money, but that I had begun to value time better. That, I think, is the beginning of getting to Inbox Free. When Inbox Zero actually feels like freedom, rather than some lesser thing.

Inbox Free to Inbox Zen

I hope where I am now is on the cusp between Inbox Chaos and Inbox Free. A state where I can periodically get to Inbox Zero, and stay predictably in a free-and-clear headspace long enough, and frequently enough, to make steady progress on my own “freedom projects.” I don’t care about maximizing revenue, and I don’t worry about “leaving money on the table.” So long as I’m making enough to pay for my life, and some savings, I’m mainly solving for freedom. It’s just taken me a decade to get to where that’s a meaningful problem with real solutions at the workflow level.

I still can’t reliably do something like block out entire weeks to make progress on some freedom project, like my much delayed science fiction novel, or the rover I am trying to build. But I can do an afternoon. And occasionally a whole day.

Progress!

Admittedly, Inbox Free seems like a distant goal now, but it no longer seems like an impossible utopia. The chaos overwhelms me more often than I am able to hold it at bay. But I’m getting slowly and steadily better at holding my own. I wouldn’t say I’m winning the battle against chaos. But I’m losing less often.

This does not happen automatically.

It takes work to create these chaos-beating conditions and maintain them. It takes cunning to turn Inbox Zero moments into Inbox Free afternoons or days. And they can be destabilized at any time by a bad quarter or year. By a gig falling through or a contract getting canceled.

Experience and a ten-year track record do not make you immune to the vagaries of the gig economy. Just because I’m a decade into the game does not mean I can’t hit a bad patch, and regress back to Inbox Anxious or Inbox Void.

But having been there before, and having climbed out more than once, I have a certain confidence in my ability to do so again. And again.

It’s not Sisyphean though. It’s more like a video game, where once you reach a certain level a couple of times, even if you get killed and have to respawn at Level 1, you know you can get back to the previous highest level again. You might even be able to speed-run there. And each time you return to your previous highest level, you have another shot at making it to a new level.

I don’t know what the next ten years hold for me. I am 46 now, and will be 56 then if I am still around. Maybe there are a few more Inbox Levels to discover with increasing levels of freedom. And maybe there’s even an end to the finite game of inboxes, when I can quit playing the high-stakes version, where I have to keep score and actively work the time-vs-money tradeoff curve.

Maybe I’ll hit the Zen mode of the game, where I’m playing to continue the game, rather than to win the current level.

One can hope.