Humans-in-the-Loop
AI can do many, many things. But it cannot replace Lived Experience
This month at Optionality our theme is “Wisdom Exchange” and we are hosting members of the community with deep wells of Lived Experience to share a spoonful of it with our community. It got me thinking about much we stand to lose — at the company, societal, global level — from letting Lived Experience go to waste. And it reminded me of this story that reminded me how, even when work is changing at a break-neck pace, our Lived Experience is what will guide us.
Nearly ten years ago, after exiting the first startup I co-founded with my Optionality Co-founder Elisa Camahort Page, I decided to start dating other technologies.
Don’t get me wrong, social media, and the creator economy it inspired, had been very good to me, but I had become disenchanted with aspects of digital media, intrusive and creepy ad tech in particular. I wanted to take the skills I’d developed as a founder to storytell around something entirely disruptive, mission driven, and uncharted.
My first post-acquisition crush: Virtual Reality. And through this crush I was introduced to another technology that was still commercially unproven but that opened my eyes even wider to possibilities than social media had, with use cases in finance, government, healthcare, even space exploration: Blockchain.
Once I grasped even an ounce of its potential I was hooked. THIS, I told myself, is where I’m going to build next.
I was connected to one of the largest and, I would argue, influential blockchain companies that existed at the time, and it so happened this company was looking for a marketing leader to take it to the next level of its meteoric trajectory. I threw my hat in the ring and joined the company.
I was told that this company worked very differently than others, it was a holacracy, or had a “flat” org structure, in alignment with blockchain’s decentralized technical framework. And it had an extremely progressive remote-first workplace policy, especially noteworthy for a startup in the pre-Covid, pre-hybrid era, that enabled employees to work from anywhere–from home, from any of its offices located in over 20 cities globally, or even from an Airbnb in Majorca. It wasn’t unusual to have team members from other countries visiting the local office, in town on personal business.
The company was growing rapidly, and while it had a strong reputation as a pioneer in the space, with leading global experts to inform strategy -- from former entrepreneurial rock stars to former executives in finance, media and tech -- there was no coordinated strategy or set of KPIs for my team to follow. I would need to establish them, gaining consensus among my team and across the organization every step of the way.
I managed a global group of 30 people in the marketing “circle”; for many of my team this was their first or second post-undergraduate job. Yet for a team lacking experience or a cohesive strategy, it was insanely productive, producing hundreds of events around the world and generating awareness among untold numbers of developers, organizations and influencers. Each member took it upon themselves to learn about the technology and the ecosystem enough to have a significant individual impact.
Still, I questioned the sustainability of the holacratic model. Holacracies are not democracies–decision-making authority may be distributed, but authority is not granted to a person or idea simply because the majority agrees to it. Consensus could be achieved without unanimous agreement, but only if everyone in the circle agreed to that standard. I needed consensus on all decisions, from how the team worked to what we would prioritize.
Polling the team, I noted that it used multiple CRMs, PM tools and workspace systems, which impacted cohesive productivity; something everyone on the team agreed was an issue, but on which some refused to compromise. Some team members did not agree on what activities were most important. For instance, one told me he wouldn’t “do marketing,” and kept to his very specific priorities building developer initiatives in his country and not engaging with any other activities in his region. One was going to spend several months on another continent, which I feared would impact his ability to run campaigns in his region, but under a self-management mandate, there was little I could do to enforce, shared, cohesive practices that I know worked.
I sensed that most of the team were highly skeptical, perhaps even scared that I would interfere with their individual projects by imposing priorities and best practices. One teammate who referred to me as a “Middle Management Marketer” set up a poll for the group suggesting a change in my title, from group Head to something with less implied authority, a proposition the team overwhelmingly voted in favor of. Only one member expressed to me privately any appreciation for an experienced team member, confessing that prior to my arrival she had been feeling quite aimless and needed some structure.
It took many months to earn the team’s trust and implement my strategy, but by then Crypto Winter impacted the market and a massive reduction in force cut my team to half its size.
Despite the downturn I stayed on to help strategize and rebuild under a different economic climate, finally feeling like my experience as an operator scaling in resource-constrained environments could be useful. Still, I ended up leaving a few months later, not because I was done learning from the organization, but because its structure made it nearly impossible for others to learn from me. I came to the company wanting to apply my experience in one field to build something new in another. I didn’t feel unappreciated so much as underutilized.
That feeling, I suspect, is not dissimilar to how many in mid career are feeling now, with the emergence of AI.
I’ve been thinking of that bygone era of my career lately, as we watch an even more dramatic and ubiquitous shift in work forged by AI.
The most critical asset we earn by working is Lived Experience, and yet layers of the most experienced workforce talent are being supplanted, in essence being told, your years of learning and development are no longer good here.
And yet, it seems this is perhaps the most critical time for leveraging lived experience, to learn from others who have experienced seismic shifts in the marketplace and workforce.
A client of mine has built an AI-powered solution for closing the skills gap in the workforce, galvanized by stories shared with her by former peers. One, a senior executive in a Big Tech company, was laid off to make way for less-experienced talent with AI acuity, but the company never knew that this executive had been up-skilling in anticipation of shifting needs. She was never asked about her skills, or evaluated, or approached about transitioning into a newly-scoped role.
In cases like these we stand to lose untold amounts of institutional, or tacit knowledge that AI cannot replace, (or replicate quickly).
On the other end of the talent spectrum, promising, entry-level workers are being denied opportunities for developing this expertise. A report by Global Markets Investor revealed that unemployment among recent college graduates has surged to 9.3%, higher than during the Great Financial Crisis and the worst level since 2021.
Optionality Marketing Coordinator (and resident Gen Z) Ryan Tate gave this trend a face when he shared his story of struggling to get traction in an ultracompetitive job market
So then, how can we reclaim learned experience in the workplace?
Solve for Potential
Remember that phrase, “No one ever got fired for buying IBM”? I hear it bandied about in enterprise software circles to justify risk aversion and inability to try something (or someone) new. The result: Archaic backend processes and solutions, and a revolving door of the same archetypal leaders into companies.
At least until they are disrupted by something – or someone – greater, which is happening now.
With this seismic shift in the world of work, where the playbooks are not just being revised but replaced, we might want to stop pretending there is an endless supply of “seasoned” experts out there who have “done AI” many times over, and start extrapolating one’s competence based on potential and lived experience.
This is not as difficult as it sounds: The workplace is hinting at a new world order, and leaning on microindicators of potential–also known as skills–that can pinpoint potential more than any business fraternity membership or Six Sigma Black Belt can.
With more proven metrics available to us than ever before, adhering strictly to educational pedigree or competence-by-association hiring models will not just become passe; this could likely get you fired.
Distinguish between Experience and Entitlement.
During my time at Blockchain Behemoth, I recall being continually impressed with the level of understanding of the new decentralized world order among young team members, who never needed to unlearn centralized models of management, finance, and networking. They proved to me how unfettered potential, in the form of passion and brilliance, could create outsized impact.
I also recall being somewhat astonished at the sheer entitlement Holocracy hath wrought, and the poor proxy it was for enlightened management. I encountered several younger colleagues who, benefitting from the illusion of having more work experience in our flat org structure, were disappointed, even disillusioned when they discovered they were not paid the same as more experienced colleagues or consulted for high-level decision making. I recall some expressing more devastation over not being involved in the layoffs decision than in the layoffs themselves.
As much as I feared the disruption layoffs would have on my team’s morale, they had an unanticipated effect of focusing their attention and elevating guidance from those who had managed through downturns before. They enforced a reversion to good, old-fashioned management techniques based on lived experience: KPI development, budgeting, and a tried-and-true business analysis and strategy.
Education is a Door-Opener. Learn by Teaching.
Want to differentiate your product, service, or company in the AI economy? Offer to educate your market, leaning on your lived experience to level-up employees, customers, partners in your industry. People are willing to embrace new world orders when you offer them an edge in understanding them.
Back when I was growing an influencer media startup, I used my lived experience in media to educate brands on new forms of social marketing, resulting initially in building their trust, and eventually in paid partnerships. I took this same playbook to blockchain and now to AI companies, combining my management’s lived experience with my own experience mainstreaming emerging tech and building companies, all while learning new tricks for myself.
I learned a ton about AI’s impact on the enterprise when I worked with a team that built and took to market an AI learning experience for 750 non-technical Global 2000 executives. We were a small, but informed, team of experienced operators and educators, and new doors opened to us because we met a powerful need to learn and upskill in a rapidly emerging space.





You are a powerful writer, my friend. So food. I learn from you every time. Plus, food for thought. Yum!