Hi Reader,

Working in a self-managed organization is fun, liberating, and extremely rewarding. Both our companies, Corporate Rebels and Krisos, are set up as self-managing teams.

No bosses. No hierarchy. Instead, everyone takes initiative within their own roles, leading their areas of the business and involving others where necessary.

Most people see why that's a great environment to work in. And if you’ve been following this newsletter for some time, you know we love it.

That being said, it’s important to understand it’s not all rainbows and sunshine.

Today, I want to talk about the other side.

The struggles, the challenges, the pains

Let’s dive into the challenges of self-management – both from personal experience and from the research we’ve conducted into self-managing organizations from around the world. For those of you working in a self-managed company or team, prepare for some aha moments.

1. The paradox of freedom

In self-managed organizations, we often talk about freedom. Freedom to make decisions, freedom to shape your work, freedom from bureaucracy. But it doesn’t come in solitude: with great freedom comes great responsibility. And sometimes, that responsibility can feel overwhelming.

You're not just responsible for your tasks, but for the entire ecosystem around them. You need to consider how your decisions impact others, how they align with the company's purpose, and how they contribute to the bigger picture.

There’s nowhere to hide. No manager to save you when the going gets tough. Sure, there’s (hopefully) a supportive team around you, but they’re there to support, not to take over your responsibility.

It's exhilarating, sure, but it can also be paralyzing and uncomfortable.

2. The leadership challenge

In self-managed organizations, leadership becomes a delicate dance. It's about knowing when to step up and take charge, and when to step back and let others shine. This constant shifting between leading and following is a skill that doesn't come naturally to most.

One day you're driving a project forward, rallying the troops. The next, you're supporting a colleague's initiative from the sidelines. Finding this balance is tough. It requires a level of self-awareness and flexibility that can be mentally exhausting. It's a constant struggle to know when to assert yourself and when to create space for others.

Personally, I regularly struggle with this. Especially with roles that are closely connected to mine that I’m highly passionate about. My enthusiasm sometimes eclipses the space that others need to thrive.

Clearly, a work in progress 😅.

3. The autonomy-alignment tightrope

Self-management offers a great deal of autonomy within roles. You're the captain of your own ship. But here's the catch: we're all sailing in the same fleet. The challenge lies in finding the right balance between individual autonomy and organizational alignment.

Too much autonomy without alignment can lead to chaos, with everyone rowing in different directions. Too much alignment without autonomy can stifle creativity and lead to the very bureaucracy we're trying to avoid. Walking this tightrope is a constant challenge, requiring ongoing communication and adjustment.

Currently, at Corporate Rebels, we’re finetuning our balance. With lots of new developments, projects, and opportunities popping up, everyone was heading off too much in their own direction. Great in terms of autonomy, but not in terms of alignment.

We’re redoing our strategy now and will jointly evaluate new big opportunities. To guide the passion and the autonomy in the same direction.

4. The skill gap challenge

Self-management requires a unique set of skills that most of us weren't taught in school or previous jobs. Suddenly, you need to be adept at taking responsibility, conflict resolution, strategic thinking, and collaborative decision-making.

For many, it feels like being thrust onto a black diamond ski slope with only sledding experience. It takes time, training, and a whole lot of practice to master it.

Remember, every expert on that slope was once a nervous novice at the top. The key is to start, persist, and never stop learning.

5. The emotional toll

Here's something we don't talk about enough: self-management can be emotionally draining. When you're deeply invested in your work and your team, conflicts hit harder. Failures feel more personal. The line between professional and personal blurs, and that can be tough to navigate.

So, to all you self-management practitioners out there, I salute you. It's not an easy path, but it's a worthy one.

And to those considering this approach, go in with your eyes open. It's a rollercoaster ride, but one that can lead to incredible growth and fulfillment.

What about you? Have you experienced similar challenges in your self-managed organization? How do you deal with them? Hit reply and let me know. I'm always eager to learn from fellow rebels.

Until next time, keep pushing boundaries and embracing the beautiful chaos of self-management.

Cheers!

P.S. If you want to dive deeper into making self-management work (challenges and all), check out our upcoming Masterclass. We don't sugarcoat it – we show you the real deal. When you enroll before 31st of August, you get complimentary lifetime access to our membership platform with the courses, live events, and community you need to enhance your self-management expertise. Enroll here.

Updates from Corporate Rebels HQ

Here's a quick overview of everything happening at Corporate Rebels:

• Our database of self-managing organization continues to expand. We’re close to 1,000 organizations now. If you know of any, please share them by replying to this email.
• Our new book is still in the finalizing stages, but takes longer than expected. Some major improvements are being done at the moment. This pushes the publication date back somewhat. It was October, but will be a few months later. Stay tuned for one of our most important contributions to the world of self-management.
• As mentioned above, we have a few spots left (just ten!) for our September Masterclass cohort (Asian/Oceanian time zone). Enroll before August 31.
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New article

A new article has been published on our website earlier this week:

• Stapelstein's Transition to Steward-Ownership​
  Discover how Stapelstein, a mission-driven toy company, fought to realign its ownership structure with its core purpose. From startup enthusiasm to ownership deadlock, their journey reveals why the often-overlooked aspect of business ownership can make or break a company's mission. Learn how Stapelstein's innovative solution could reshape how we think about purpose-driven enterprises. Read it here.
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What inspired us

Here's something noteworthy we discovered this past week that you’re going to love:

• The Double-Edged Sword of Self-Management
  ​In line with today’s theme, this recent study on a public sector addiction rehab center reveals the complex reality of self-managing organizations. While confirming benefits like increased responsibility and efficiency, it also uncovers challenges such as inter-team conflicts. The authors find that work in a self-managed organization can be simultaneously positive, challenging, and at times, "impossible." A crucial read, download it here. ​​

Your weekly challenge

At Corporate Rebels, we believe that small changes lead to big results. That's why we challenge you each week to make a small but significant change. This week....

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Cheers,

Time-Limited Offer: Complimentary Lifetime Access (only 9 spots left!) We've sold out all available seats for the first September cohort of our Masterclass "Running and Scaling Self-Managing Organizations," so we opened a second cohort, which kicks off on September 24. ​ If you enroll in our Masterclass before August 31, you will get: Full, lifelong entry to our online community, where you'll enjoy monthly events, exclusive interviews, cutting-edge case studies, and much more. Unlimited access to your Masterclass content, extending beyond the usual one year. Ongoing access to all our current and future on-demand courses, typically valued at €948/year. ​ That's right – all of this is included in the one-time Masterclass fee of €5,000, with no annual subscription fees (usually €948/year) required. Ever. ​ But act fast – this offer is limited and there are only 9 spots left. Click below to discover more about the Masterclass program and this special promotion. ​ Explore the offer

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