My friend Adrian shared a post about an AI-powered boss — a digital overseer to manage your work schedule, enhance productivity, and eliminate the stress of decision-making. I could almost hear him screech through WhatsApp, "Hey machine, take away my freedom to choose!" After all, he is a fervent creative, rebellious spirit, and decidedly anti-authoritarian.

I didn't have such strong feelings, but it presented a tasty thought experiment: if such a service existed, should I consider it? There were wide swaths of my work week lost to distraction and AI has been such a revelation. So why not? When would it be appropriate to let AI take control? What does this reveal about our values, priorities, and our ability to live meaningful lives? Why do we feel both drawn and uneasy about this idea?

The seemingly inevitable possibility of an AI boss and Adrian's visceral response inspired me to reflect more deeply.

Why not let AI be our boss?

The truth is the vast majority of people work under the purview of someone else (boss or client), and most of us, under multiple layers of authority. So while working fully autonomously sounds ideal, from a practical point of view, few of us actually pursue it. Maybe an AI boss is just an innovative idea that we're yet not used to.

There are, of course, a few people who are legitimately independent, but I'd wager that distraction and lack of direction still remain a constant concern. I also think of those who clinically struggle with focus and productivity (i.e. ADHD) and the many more creatives, entrepreneurs and wantrapreneurs who struggle, albeit without the diagnosis. So AI, in these contexts, could serve as an ideal overseer — keeping us on track, never forgets, and always knows the next best step.

The allure is undeniable. With its 220k social media followers, there's clearly interest in the promise of super-charged efficiency. Get more done and spend less time doing it. After all, the algorithm would have an almost omniscient understanding of productivity, and for just a few cents a day. Who could resist? Why resist?

Why Resist?

The more I reflect, the more I see the potential value in such an AI boss. Still, there’s something disquieting about the notion of relinquishing control, to entrust our daily lives to an unseeable, unknowable, un-influenceable entity. It feels like an existential choice: do we plug in, take the blue pill, and embrace a life of effortless comfort? Or do we take the red pill, pierce the veil of reality, and actively engage in the struggle of existence?

I actually fear that this choice will not be presented to us as starkly clear as in The Matrix. Instead, I suspect it will be a subtle slide down into dystopia... a series of AI-supported, micro decisions… and that dystopia will actually appear as a vibrantly saturated, seemingly self-empowered world.

But, that is just a fear, probably heavily inspired by cinema. Plus, it's a future that is not here yet, so before I start building my doomsday bunker, let’s continue exploring the idea of an AI boss.

Managing Like a Boss

This service is sold as an AI-boss, and maybe it's a good metaphor. It conjures up memories of corporate life and the concept called "managing up" — being aware of your boss's goals, their expectations and tendencies and being a few (or many) steps ahead of them.

In building that awareness, we're also forced to reckon with our own, our goals, expectations and tendencies... working to negotiate the distance between our boss's and our own path. So perhaps our relationship with AI should be approached similarly, because the wrong approach with AI (or your boss) —would be of:

• Complacency: Losing sight of your own agency, failing to set boundaries, and simply accepting whatever directives are given without question.
• Ignorance: Failing to acknowledge your own emotions, disregarding the impact of it's decisions on your well-being.
• Negativity: Complaining and criticizing, without proposing alternatives or taking actionable steps to change, thereby perpetuating a cycle of dissatisfaction without resolution.

Framed this way, the question of an AI boss becomes: Who is leading whom? Are we consciously guiding our relationship with technology, or are we passively allowing it to lead us? This (as most things) requires a deep level of self-awareness... knowing what we want, our values and beliefs -- and trusting that internal compass as we navigate the complex and subtle web of external influences.

The Paradox of Self-Struggle

I consider myself fortunate to have had the luxury of time to find my own path towards autonomy and productivity. It's really taken years, decades, to cultivate this even basic sense of self-awareness and for it to develop into a reliable internal compass.

Of course, if I’m honest, I'm jealous of the AI superpowers that future generations will get to experience. I wonder: what would I choose if I were younger today? Wouldn’t I want that AI boss, wary of falling behind my super-charged peers? Or would I have been somehow strong enough to resist, patiently working through the painful struggle of autonomous productivity?

Because only, standing on this side of reality, having gone through the slow, uncertain and painful struggle that I know the joys and value of it: invaluable lessons about the creative process... a deeper connection to society and the world... and insights into myself that do not come from external sources.

What You Must Do

This brings us to a crucial distinction between management and leadership. AI may excel as a manager — it can assign tasks, track metrics, and ensure everything is completed on time. But what of leadership? AI lacks the ability to envision, to feel, to truly understand the nuances of a human life. Leadership is about creating meaning, about guiding not just tasks, but the human spirit. AI might help us execute flawlessly, but it will never replace the ability to offer a sense of transcendent purpose.

Ultimately, this is about self-leadership. I can’t tell you which choice to make—whether to fully embrace AI or keep it at arm’s length. It’s an individual decision, one that depends on your values, your aspirations, and your awareness of what makes life meaningful to you.

If AI is to become a part of our lives, we must be intentional in its use. Decide how you want to use it, in what capacity, and always maintain awareness of where the boundary lies — where assistance ends and autonomy begins. At the heart of this question is not whether AI should be your boss, but whether you are prepared to lead yourself, using every tool available, without ever losing sight of what it means to be human.

Brian Tam
-Thinking partner for thoughtful founders