Common Mistakes in Self-Management: Introduction

Simon Mont
4 min readSep 24, 2019

Every day more organizations are reimagining how they work together. People feel the pains, inefficiencies, and contradictions of the rigidly hierarchical systems that pervaded 20th-century organizations, and they sense that there is a way to bring more passion, humanity, creativity, and fulfillment into our work. These folks are rolling out plans based on ideas like “self-management,” “flattened hierarchies,” “distributed leadership,” and the like, all of which promise to make their dreams of a utopian workplace come true.

And every day, the people implementing these ideas confront struggles. The struggles often beget frustration, and disappointment that the reality of these systems seems to fall so short of the wholeness, community, innovation, and effectiveness that they promise. It’s not uncommon for these experiences to even lead folks to disavow the idea of self-management completely.

But we don’t need to interpret the struggles of self-managed organizations as evidence that self-management is ineffective; it makes much more sense to interpret them as evidence that self-management is hard.

And this difficulty should be expected. Self-management isn’t just a new approach to business management; its a new approach to being humans in groups. We aren’t just solving for productivity and efficiency, we are solving for the fact that past ways of organizing ourselves only solved for productivity and efficiency. We are stepping into the challenge of genuinely tending to human dignity, personal fulfillment, and well-being. We are trying to work together in ways that let us support each other to achieve common purposes while providing fulfilling personal experiences. This isn’t a small shift. It’s a fundamental re-evaluation of many of the systems, practices, and assumptions that have structured how humans have worked together for as long as there have been such things as “businesses,” “corporations,” and “nonprofits.”

If we approach this task with the mindset that we just need to implement the theory in a book, we will fail. If we think that there is a predetermined structure that will bring the outcomes we want, we will fail. If we confine our thinking to the limits of management and business thinking, we will fail. The reason is simple: reliance on theories, predetermined structures, and the history of business/management thinking are precisely the things self-management is trying to transcend. So while self-management may appear to be another theory, its not. Self-management (or non-hierarchy, democratic workplaces, etc.) is vision that another way is possible, it conveyed in words that remind us of potential that already lives inside all of our hearts, and it shared along with practices that point the way to path each organization will have to uncover for themselves.

It’s not surprising that many folks who think they understand self-management are disappointed by the results when they try to implement it. There is a long distance between understanding self management and embodying it. When we try to understand it, we often see it as a set of rules, structures, and processes that are designed to create certain outputs. But when we actually start to live it, we confront the fact that many of the ways we think, feel, and behave are not resonant with the way that we truly want to be engaging with each other. And skillfully navigating this reality is not something many of us have been trained to do.

For example: We may understand the idea of a system where every member is empowered to contribute their unique talents, but trying to live it brings us into an amount of complexity that no book or article can fully capture: We quickly realize that we each need different types of support in order to fully show up, and some of this has to do with personal history and systemic oppression; we constantly project our conditioned beliefs about what each other are capable of, and we are impacted by each others projections; we often feel threatened by folks with similar skills; we have been trained to value different skills differently; we’ve even been trained to see some people as more worthy of human dignity than others. All of these currents (and more) influence whether people will actually bring their skills in practice. Until we learn how to navigate this cultural and relational terrain, promises like “everyone will utilize their unique talents” will remain unfulfilled.

We could say self-management doesn’t work, throw it out, and revert to hierarchy. Or we could stay committed to a vision that creating a better system is possible and proceed to navigate this terrain with unprecedented creativity.

Converting to self-management is like taking the training wheels off a bike. Suddenly we have to consciously and responsively balance all sorts of factors; factors that we hadn’t even realized were previously being taken care of by an apparatus that was as limiting as it was supportive.

As we wobble along, trying to make our visions real, there are a few common mistakes that folks are making. Hopefully by naming them, we can come to understand them not as reasons to reject self-management, but rather as the terrain of the emerging frontier in self-management practice. And hopefully by embracing the opportunities for growth they represent, we can help each other navigate them more skillfully.

This series overviews three common mistakes:

(1) we let informal hierarchies dominate;

(2) we don’t support people; and

(3) we avoid authenticity.

The series then closes with some takeaways.

May it serve our journey toward a more just, loving, thriving, and liberated world.



Simon Mont

A co-creator of just, joyful, and innovative workplaces. Reach out to for consultation, training, and coaching.