A Portfolio Approach to Modern Work

In the past, being a freelancer meant being a specialist.

The only way you could generate enough income to make it as a free agent was to focus on a single, highly monetizable skill. For example, copywriting, coding, graphic design, photography, journalism, or language translation.

You had to be able to perform this skill in isolation, because collaborating closely with others involved too much friction. Thus paradoxically, becoming a freelancer has traditionally involved making your work more predictable and structured, not less. You could only afford to make your lifestyle more flexible by making the work itself more rigid and monotonous.

This has always limited the number of people who could sustainably become freelancers. There are relatively few people who have the passion and intensity to develop a highly specialized skill, who also are willing to spend years deploying it in isolation.

But there’s another, deeper drawback: freelancers have always been exposed to the downsides of self-employment (income volatility, no safety net, no benefits, changing market needs), while at the same time not being able to take advantage of unexpected upsides. Forced to stick to their prized skill, they’ve had difficulty moving to related fields, riding upward trends, or training in new skills, because any such move resulted immediately in a drop in income.

But I believe we’re witnessing the rise of a new kind of worker: the Full-Stack Freelancer.

Full-Stack Freelancers respond to technology as an opportunity, not a threat. They leverage software-as-a-service and online platforms to vertically integrate a “full stack” of capabilities, instead of focusing on one narrow function. This allows them to capture a much greater percentage of the value they create, instead of giving it away to gatekeepers and distribution bottlenecks.

Full-Stack Freelancers are responding to a series of technology-driven trends — contingent employment, intensifying globalization, and automation — by taking advantage of the other side of the coin: technology finally becoming powerful enough, cheap enough, and user-friendly enough to be deployed productively by a single individual.

They borrow freely — from tech startups, digital nomads, lifestyle designers, independent contractors, the sharing and peer-to-peer economies — but placing them squarely inside any of these categories is not quite right.

That’s because Full-Stack Freelancers manage a portfolio of income streams, not a job based on one set of skills.

These potentially include both products and services, online and offline businesses, digital and physical products, active and passive income sources, in-person and remote interaction, individual contribution and group collaboration, and offerings that are low margin and high margin, mass-produced and customizable, high risk and low risk, monetized directly or indirectly, short-term and long-term, or any combination of the above.

Sound impossible? It’s not. But it requires a skill that virtually none of us are educated for: portfolio thinking.

Portfolio thinking

It’s trendy now to proclaim the universal superiority of “deep work.” We’re advised to lock out all distractions and interruptions, fixate completely on one project at a time, and optimize for long, long stretches of focus.

This advice isn’t wrong; it’s just limiting. It’s appropriate if what you want is to be the best employee you can be. If, on the other hand, you want to be a manager, run a business, develop side projects, or collaborate with others, it is terrible advice. It gives you no portfolio to work with.

Portfolio thinking recognizes that having multiple parallel projects provides many opportunities for synergy. They don’t have to interfere with and impede each other — they can actually combine into something greater than the sum of its parts. Each one can make the others easier, more fun, and more profitable.

My freelancing business, Forte Labs, turned 4 years old this month, and I’ll use it as an example. My portfolio contains (in the order they were added) public workshops, self-paced online courses, corporate trainings, consulting on various topics, 1-on-1 performance coaching, and a membership subscription for my blog.

Here is a breakdown of my aggregated income sources over the last 4 years:

This pie chart masks huge variability month to month and year to year, but the takeaway is clear: the great majority of my income comes from two sources, corporate trainings and online courses. They are both services — training and teaching — that I’ve productized using digital platforms, to make them more scalable and automated. They are, obviously, essential to my continued survival, as they allow me to make money semi-passively (in the case of online courses) and without having to start from scratch each time (in the case of corporate trainings).

But describing what I do as a training business doesn’t feel quite right, when you look at how I spend my time:

The two sources that make up 81% of my income take up only 34% of my time. My third biggest source of income, consulting, produces 13% of revenue but takes up 24% of my time. And the least profitable sources — public workshops, membership subscriptions, coaching, and other — contribute 6% to the top line, but consume a whopping 42% of my time.

One way to think of this is that technology helps me produce enough leverage for 3 days of the week, that I can invest 2 whole days in activities with no immediate return.

This graph at first glance looks like the epitome of multitasking. If I was an employee, it would suggest that I’m dividing up my time among too many priorities, and therefore not developing the specialization that is my golden ticket.

But as a Full-Stack Freelancer, this distribution looks just about right.

To explain why, we need to look more closely at the key principle that makes portfolio thinking work.

Opportunistic addition

Portfolio thinking takes advantage of the principle of opportunistic addition: there are many things you can spend time on that add value when done in moderation, but whose returns quickly diminish the more of it you do.

James Clear uses the example of a book author who also does speaking engagements. Writing fewer books would obviously negatively impact his ability to secure speaking slots. But doing less speaking would also hurt him. Doing a few such speeches a year can add thousands of dollars to his bottom line with relatively little effort. Without these extra dollars, he may have to take on more time-consuming projects that leave him less time to write.

In other words, occasional speaking engagements are not a distraction for this author. They are essential enablers of his ability to dedicate large amounts of time to the deep work of writing.

This may seem like an isolated example. I want to convince you that such opportunities are totally pervasive, low-hanging fruit available to anyone willing to diversify their portfolio.

For example, I’ve found that pure consulting is extremely difficult for me to do profitably. Starting each project with a new client and a blank slate means there are huge startup costs, long periods of exploration and experimentation with no corresponding compensation, and lingering projects that never quite seem to finish. Selling my time directly, it is too easy to get nickel-and-dimed with small asks. Not to mention the difficulty of bringing my very best creative thinking to the table every single day.

But when done in moderation, say once per quarter, consulting jobs are an incredible source of exploration and learning. The best, most original ideas simply can’t be found by reading blog posts and books. They are emerging from the chaotic process of conceiving, designing, producing, and selling real products in the real world. Getting access to this messy, but priceless learning requires some level of engagement with makers. If I can do that while being paid, all the better!

The same goes for coaching. If I had to make a full-time living as a performance coach, I’d have to lower my per-hour rate until my schedule was full, leaving me no time for other projects. But doing it only occasionally, it provides a valuable opportunity to look deep inside someone’s productivity systems. Hearing about their experiences and the unique problems they face is like a shot of adrenaline to my empathy centers. It helps me step outside my perspective and into someone else’s world, where I’m always surprised to find different ideas and beliefs than my own.

Building a portfolio

It’s probably not hard to believe that each of these activities is worthwhile on its own, but you’re probably wondering how in the world one person could maintain so many threads.

The key is to understand that premium products and services, like corporate trainings and high-end online courses, require long sales cycles. They are not something one buys on impulse. The customer has to know you, understand where you’re coming from, and trust you. This requires a rich, interactive process of reading your writing, watching your videos, seeing your social media posts, perusing your email newsletter, and trying out your more affordable offerings.

In a large company, much of this is done by salespeople and marketers. They can dedicate themselves to having long conversations, covering the dinner checks, putting out free content marketing, and organizing events and demos. They can do all this knowing that another part of the business, the product, will monetize their efforts.

As a Full-Stack Freelancer, you have to monetize this sales process yourself. You can call it a “relationship builder sequence” if that makes you more comfortable. You can’t put in a ton of work upfront only hoping it will someday pay off. Some of what you put out should be free, of course. But the sooner you start charging, even if it’s $5, the faster you’ll start learning. The words of a paying customer are worth far more than a spectator’s.

The different ways you monetize and derive value from your sales process are the items in your portfolio:

I’ll expand and fill out this visual in subsequent posts

Social media shares and free blog posts are your lead capture, bringing people into your audience. They also keep you exposed to the wider world beyond your niche.

Your introductory offerings are your qualification and filtering system, helping you identify not only the people who are most committed to your message, but also the best ideas and formats to help carry that message.

Premium offerings are the cash cows, allowing you to provide the most value with your time, and be compensated accordingly.

Network effects

What may not be immediately obvious is that the model above is not just a one-way funnel — it is a network. A given customer can follow multiple possible paths through my network of offerings. Each additional offering provides another entry point into the network, which increases the number and diversity of people I can serve.

But it isn’t just customers that traverse the network in all directions. Information and value do too.

I often learn about a new topic or trend from a consulting job that fuels my writing for months, adding value to memberships. Facilitation skills learned in public workshops make me comfortable offering a live online bootcamp, combining the best of online and offline formats. Nearly every coaching client shows me a new tactic I’ve never thought of, which I can then package up and share in corporate trainings as real-world implementation advice. And of course, all sorts of “unpaid” activities suddenly become worthwhile when I know that every conversation is an opportunity to bring someone into my network, where I often can’t even predict the value they’ll contribute.

All of these are real examples from my experience, and they are all examples of the principle of multifinality — accomplishing multiple ends with a single means. If you only have one offering, then the value of, say, building a new website only flows to one node. If you have 5 offerings, that single website adds value to all 5 nodes with a single effort.

Since my portfolio is a network, it exhibits network effects: each offering added increases the value of all the others. Why? Because there is tangible brand equity involved in having a multi-touchpoint relationship with my audience. I build trust by interacting with them in different environments with different goals. This trust in turn makes it easier to launch new offerings, as more people are willing to give new products a chance.

Unbounded learning

Formal schooling frames our career choices in stark terms: either hyperspecialize, putting all your eggs in one basket you hope and pray will be relevant for years to come; or take a gamble on self-employment, testing your resilience and risk tolerance under extreme conditions.

Perhaps the most compelling aspect of Full-Stack Freelancing is that it offers a middle ground, with potentially the best of both worlds. It is pragmatic, recognizing that most people are generalists who want to pursue diverse interests. But it is also aspirational, recognizing that you need the flexibility to take advantage of unexpected opportunities.

A Full-Stack Freelancer does not see a black-and-white world of free agents vs. wage slaves. They are more than willing to incorporate full-time employment as one item in their portfolio, temporarily or long-term, knowing that it neither defines them nor limits them. Breaking down this barrier, we see that the full stack is available to everyone. It requires only a level of engagement with technology as producers, not just consumers. More fundamentally, it requires a willingness to grow your portfolio toward toward areas of uncertainty and discomfort, instead of only toward existing strengths.

I believe this is actually the most profound benefit of a portfolio approach to work: it is fundamentally unbounded when it comes to personal growth, creativity, and learning. Changing direction is just a matter of adding or removing an item from your portfolio, not making a dramatic, wrenching career change. This offers the possibility of a deeper sustainability than even a well-paying job can provide.

In the following posts, we’ll explore what is required to make Full-Stack Freelancing work, and dive deeper into the components of the stack.

Read Part II here

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Series NavigationThe Rise of the Full-Stack Freelancer, Part II: The Stack >>