Pursuing the Autonomous Life

In May of 2020, my CEO, Rob, sent me a message I wasn’t expecting. “I want you to co-lead our future of work project.”

COVID was still raging on, and every worker had been displaced. At the time, we, like many companies, were scrambling to figure out how to work well together while fully distributed. We still had targets to hit. We still had earnings to report each quarter. We still had customers to support. We still had to build and ship new products and features.

That experience didn't just change how I thought about remote work. It changed how I thought about work, period.

What I witnessed during Project Beehive was a preview of where everything was heading. Here we were, a hundred volunteers from a 1,300-person company, redesigning how a public enterprise was supposed to function. We didn’t design it from a boardroom or a corporate playbook, but from the ground up with the people in the hot seats. We used first principles, believing that the way most companies operate is a relic of an era that was well past its expiration date.

I didn't know it at the time, but that experience planted a seed that would grow into the single most important decision of my professional life. The decision to stop building on rented land and start building something I actually owned.

Most people reading this probably sense something similar stirring. Maybe it's a quiet hum in the background while you're grinding through pipeline reviews. Maybe it's louder than that. Maybe it’s keeping you up late at night every once in a while.

Good. That feeling is a healthy signal.

There's a video from a popular futurist, Sinead Bovell, that explains this simply. She studies economic disruption the way meteorologists study storm systems — tracking the signals in the data, mapping where the pressure is building, and calmly explaining what's coming before most people feel the wind change.

Her thesis is clean and hard to argue with: the job market, as we know it, is going away. Not in some distant, speculative future. Now.

Her argument rests on a few observations that, once you see them, it’s hard to unsee.

The first is about who gets disrupted. The last several waves of automation — factory robots, warehouse systems, self-checkout kiosks — targeted physical labor. Blue-collar work.

But this wave? Artificial intelligence is optimized for cognitive labor. White-collar work. If your job is conducted primarily on a computer — marketing, sales, finance, software engineering, customer service, content creation — you're sitting in the crosshairs. This isn't a maybe. The data is clear.

The second observation concerns how disruption occurs. AI isn't replacing entire jobs overnight. It's automating tasks within jobs. For example, maybe six of the ten things a financial analyst does in a day can now be handled by a machine. The analyst doesn't disappear tomorrow, but their role gets fundamentally restructured. The number crunching gets automated. The job that remains looks less like a financial analyst and more like a financial strategist — someone who directs AI systems, evaluates tradeoffs, and communicates judgment under uncertainty.

That unbundling of jobs into tasks is the real story. And it creates a cascade effect that changes the shape of the entire workforce.

When a company realizes it can automate 60% of a role's tasks, it stops asking whether it needs a full-time employee. It starts asking whether it needs a contractor. A specialist. A fractional expert who can come in, deliver against a specific scope, and move on.

Bovell calls this the rise of the independent worker. Work becomes more entrepreneurial for all of us. Instead of holding a single role at a single company, you offer your skills to several. You assemble a portfolio of engagements. You operate more like a small business than like an employee.

This isn't aspirational thinking. It's structural inevitability.

This wasn’t possible before, as we rose through the corporate ranks. The economist Ronald Coase explained in 1937 why large companies exist in the first place: because it was cheaper to coordinate work inside a firm than to contract for it on the open market. That logic held for decades. But when intelligent systems can coordinate across organizational boundaries at near-zero cost, Coase's equation inverts. Companies don't just shrink their headcount. They shrink themselves.

And the people who thrive on the other side of that contraction? They won't be the ones clinging to a job title. They'll be the ones who built transferable skills, a financial runway, and a point of view that travels with them wherever they go.

A few years after Project Beehive, I was coaching one of my Inner Circle Members — someone deep in enterprise tech sales, navigating the same waters I had navigated not long before. During our conversation, he mentioned a keynote he'd attended in Chicago by Rishad Tobaccowala, the author and longtime advertising executive who had spent the previous five years advising over 150 major companies on the future of their industries.

Tobaccowala opened with three questions that every executive he worked with was asking:

Those questions hit different when you let them land. Especially the third one.

How do you stay relevant? Both Rishad and I agreed: you keep learning. Relentlessly and deliberately. Not learning for the sake of accumulating credentials or impressing a hiring manager, but learning to stay adaptive in a world where the rules are being rewritten faster than most people can read them.

And Sinead Bovell would agree.

But here's what Rishad said that stuck with me most. He talked about AI not as a tool, but as a different species. And he framed the challenge of the next era as figuring out how humans and this new species coexist.

How do we harmonize?

That framing matters because it changes the stakes. This isn't about learning a new software platform or adding a line to your resume. This is about evolving — as individuals, as companies, as a society — in ways that most people haven't even begun to contemplate.

And the skills required to navigate that evolution? They aren't exotic. It will be through curiosity and creativity. And when I say creativity, I don’t mean in the artistic sense, but the ability to create new experiences where none existed. It will also require collaboration, because nothing significant is achieved alone. The ability to convince others by making your ideas clear, understandable, and actionable. And finally, communication. Rishad put it bluntly: if you can't write or present well, a machine will take your job.

My client and friend summarized the whole thing in a way that still echoes in my head. He said we're in a sales race to become point-of-view experts. If we don't develop strong, evolving perspectives, connect authentically with customers, and show them how a transformation actually gets done, we're finished. Because churning out proposals, generating quotes, and making cold calls? AI handles that now. What it can't handle is showing up with earned judgment and a stake in the ground. A lens shaped by real experience and real consequences.

That's the currency of the next strategic sales era. Not information. Point of view. You’d could argue that was always the case, at least that’s what the top performers figured out. Now, it’s necessary for survival.

I know this because I lived the transition myself.

When I joined LivePerson as a Strategic Account Director in 2018, I was still playing by the old rules. The hustle-bro playbook. Wake up early. Grind all day. Sleep when you're dead. Growth at all costs. I was closing deals, sure. But I was also running on fumes, averaging five hours of sleep a night and working ten-hour days, carrying the largest quota in the company.

Then COVID hit. The world stopped. And I was forced to look at the machine I'd built my life around and ask whether it was actually serving me or whether I was just serving it.

During that forced slowdown, while co-leading Project Beehive and discovering the philosophy of 37signals — a company with no salesforce, 75 employees, 100,000 customers, and eight-figure profits for 24 consecutive years — something clicked. The popular rules for growth aren't the only rules. Being purposeful about doing less can deliver better results with healthier margins. Not to mention, you feel more satisfied in the process.

I redesigned my work from the ground up.

I started tracking everything I was doing. I ditched goals in favor of systems. For the first time, I defined my "anti-goals" — things I wanted to do less of. I designed my calendar around deep work. I started reading more, writing more, sleeping more.

The results were definitive.

In my first two years at LivePerson, before the shift, I delivered $11 million in ARR across seven opportunities. I averaged five hours of sleep and worked ten-hour days.

In my second two years, after the shift, I delivered $16.3 million in ARR across seven opportunities. My deal size increased by 48%. My deal cycles shortened. I averaged seven hours of sleep and worked six hours and forty minutes a day.

Same win rate. Same number of logos. But radically different inputs. Better sleep. Less time working. Deeper focus. And a 48% increase in deal size.

By treating myself like a “calm company” instead of a burnout machine, I was able to slow down and deliver more. My fitness improved. My relationship with my wife improved. And because I was doing more reflection and writing, I was able to launch a side business, give it the attention it needed, and accelerate my path to independence. All within those six hours and forty minutes.

And nothing beats earning your first dollar outside of your sales job. That $34 brought me more satisfaction than a $14.4M did just a year prior. It proved I had specialized knowledge and value to share outside my sales role.

That wasn't luck. That was architecture. And it led to authentic autonomy.

I share these numbers not to impress anyone, but to make a point that matters more now than it did when I lived through it.

The window for this kind of intentional transition is closing.

Not slowly. Not on some far-off timeline. Some predict that, within the next five years, the structural conditions that allow a strategic tech seller to accumulate wealth, build transferable skills, and design an exit on their own terms will look fundamentally different from what they are today.

Here's why.

AI is not a complement to cognitive labor in the way tractors complemented farming or spreadsheets complemented accounting. It's a substitute. The tractor didn't replace the farmer — it made the farmer ten times more effective. The spreadsheet didn't replace the analyst — it let the analyst do in minutes what used to take days. The tools changed, but the fundamental equation held: humans plus technology equaled more output, and more output meant more demand for humans.

That equation is breaking.

When a company deploys AI to handle work that used to require a team, output stays the same or increases, labor costs drop, and those savings are reinvested into more AI capability, which displaces more labor, freeing up more capital, which funds more AI. There's no natural brake in this cycle. Every previous technological disruption had one: displaced workers found new roles created by the technology, and the system rebalanced. But AI improves at the tasks themselves. It doesn't create a new category of work for the people it displaces. It compresses cognitive work into fewer and fewer human hands on an accelerating timeline.

Dario Amodei, the CEO of Anthropic, has described it as a “century's worth of progress compressed into a single decade.” That's not hyperbole. That's the planning assumption of every major AI research lab on the planet.

And the speed is accelerating, not stabilizing. The historical brakes on technological adoption — the time to invent, manufacture, distribute, train, and integrate — are gone. The internet eliminated distribution friction. Cloud computing eliminated infrastructure friction. AI is eliminating the learning curve itself.

What does this mean for you, the person reading this?

It means the economy is splitting into two distinct paths. One group uses AI to become dramatically more capable — they orchestrate, direct, and leverage machine intelligence to multiply their output by orders of magnitude. The other group becomes passive — consuming what AI produces, following its suggestions, and gradually ceding their agency to systems they don't understand or control.

And the middle is disappearing completely.

Where does this leave you?

The theory states that where you stand when this transition solidifies is very likely where you stand permanently. That's not alarmism. That's what happens when capital no longer needs labor to generate returns. The people who own assets, businesses, audiences, and equity pull away. Everyone else stops moving. Not because they quit trying, but because the structural advantage has been locked in.

So what do you do?

You start treating your current role as what it actually is. Not the destination, but the launchpad.

Every deal you close, every complex organization you navigate, every stakeholder you align — you're building skills that could set you free. Taste. Judgment. Storytelling. The ability to translate complexity into clarity for busy executives who need someone they trust to help them see around corners.

These are not skills AI replaces. These are the skills that determine who AI replaces.

But most sellers never extract the lessons. They chase the next number, the next title, the next President's Club award. They spend twenty years making someone else rich and never build anything of their own.

I sold a conversational AI platform to Fortune 500 companies where a single experienced operator, armed with the right tools and judgment, could handle the work that previously required a hundred people. That ratio — one to a hundred — isn't a ceiling. It's the new floor. And it's coming to every knowledge-work function within the next decade.

The question is which side of that ratio you're on.

Today, an executive still can't ask AI to map out a vision for their organization and understand which technology partners will help enable it. Human judgment and point of view based on real experience are still necessary. In the next era, they're not just valuable — they're a prerequisite for relevance.

But that window is narrowing. The skills that make you dominant before AI may not be the same skills that make you dominant after AI. The financial analyst who was valued for number-crunching now needs to be a problem-solver who frames complex decisions. The seller who was valued for activity volume now needs to be a strategist who designs buying experiences.

The rules you inherited — specialize, credential yourself, climb the ladder — those rules are expiring. They felt permanent to the people living inside them, just as loyalty to a single factory for a future pension felt permanent to your grandparents, or a college degree felt like a necessity for upward mobility to your parents. But rules always feel permanent right up until they don't. And by the time you realize they've changed, the early movers have already repositioned.

I was fortunate. Project Beehive gave me a front-row seat to the future of work years before most people felt the tremor. It showed me that the traditional office, the traditional role, the traditional career arc — all of it was already being unbundled. The question wasn't if. It was when.

That experience, combined with discovering a company that ran circles around competitors thirty times its size by doing less and doing it calmly, rewired how I thought about performance, leverage, and what a career is actually for.

Your tech sales career is not a destination. It's a vehicle. In fact, it’s one of the most powerful vehicles available for building a life no employer can touch. The rooms you enter. The patterns you recognize. The income you can generate in a single year if you line things up right. No other corporate role gives you that combination of access, income potential, and transferable skill development.

But a vehicle is only useful if you drive it somewhere intentionally.

The autonomous life isn't something you stumble into. It's something you architect. It requires seeing your finite resources — time, energy, attention, and money — not as things you spend, but as things you invest. It requires defining what "enough" looks like before you get trapped chasing "more." It requires treating your calendar not as a burden you endure but as a game console you design.

And it requires starting now. Not next quarter. Not after the next promotion. Not when you feel ready. Now. While you still have the income, access, relationships, and leverage that your current role provides. While the window is still open.

The future of work is not some abstract concept that lives in keynote speeches and YouTube videos. It's a structural reality reshaping the economy beneath your feet right now, whether you're paying attention or not.

The people who see it clearly and act with intention will build something lasting. The people who keep their heads down and hope the old rules hold will eventually find out that hope was never a solid strategy.

I built my autonomy from inside the corporate world. Not after I left — before. While I still carried a quota. While I still sat in pipeline reviews. While I still had a boss.

And if I could go back and hand myself one piece of advice during those early years at LivePerson — before the hustle almost broke me, before I finally woke up to what was possible — it would be this:

The game you think you're playing is not the real game.

The real game is building a life where your calendar belongs to you, your skills travel with you, and your identity isn't leased from an employer who can restructure you out of existence on a Friday afternoon.

Start building. The window is still open. But not for long.