What happens when you become the boss?

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It’s easy to hate on the boss. The clueless middle-manager. The power-hungry doofus. Bill Lumbergh. Michael Scott, if we’re lucky.

So when we see that more and more people are starting to work for themselves instead of for bosses, we celebrate the fact. We throw up giant flags that say “do what you love.” We romanticize it, and for good reason.

But there’s a flipside to all the newfound liberty. While we may be right to take joy in shedding the oppression of full-time employment, we also must take caution in acknowledging the support and security we lose along with it. Shedding the personified human boss above you on the org chart doesn’t mean that the role of the boss ceases to exist; it means that the role now shifts to elsewhere. In large part, it shifts to inside of you.

You become the boss now. You’re the man. You are, now, perhaps, the clueless middle-manager. Heavy is the head that wears the crown, right?

Do we really want that responsibility? Are we well-equipped for it? Are we going to love it?

In a world whose attention is increasingly being consumed by an ever-improving system designed to stimulate our brains with shocking listicles and engagement-optimized tweets, do we really trust ourselves to manage ourselves well?

When the boss is us, who’s going to tell us to unplug the social media and get back to work? Who’s going to remind us that instead of playing into the development of the 21st century Couch Potato, we should be doing what we love– like we said we would?

Not everyone who is making the shift toward independent work is going willingly. Traditional full-time jobs, like them or not, are going away and not coming back. Some people welcome the change, but some are kicking and screaming. They fear a world in which they’re on their own, and with good reason. We’re not meant to be on our own.

I know how badly I need to not be on my own. I don’t want to be consumed by my own lack of discipline. I really really don’t want to hate my boss now, because he’s not going anywhere. I know I’m not the only one facing these sorts of things.

And therein lies an opportunity to shape how this plays out.

We can scatter, each of us on our own, battling social media and our own shortcomings and ever-increasing costs and who knows what else, and hope that we might eek out a happy life somewhere in between. Or we can find new ways to organize and help each other.

This is why I believe so deeply in the potential of Coworking. By putting us in the same room together, it gives us a fighting chance. But it can’t just be window dressing on an office space rental business, as many believe it is now. We have to think of it as a tool to build better ways for us to support each other.

How we approach that is something I’ve been looking at from a lot of angles. I’ve found some answers, but there are so many more yet to be found.

If you’re around next Saturday, a group of us will be talking about these kinds of things all day. I’d love for you to join. I’d also love to hear your voice in the comments below if you have a moment.

Collaborative motivation groups

Cotivation at New Work City

Back at the end of 2012, I was facing an interesting challenge: New Work City’s membership was lagging after a slow Fall season, and the culture was starting to slide into one of passive workspace consumption. Which is not what we’re about.

So I wanted to undertake an effort that would simultaneously stimulate interest in membership while also creating an opportunity to revitalize the culture from within. I wanted to promote our place in a way that was more substantial than just “we’re great, come hang with us! Really!” — so I thought about a program that would give people a way to forge deeper, more intentional working relationships with each other.

I thought about what I needed myself, and what I saw in others. Two themes came up consistently: structure and accountability. In traditional employment, these things are taken care of, but for independent workers these critical constructs are nearly nonexistent without some kind of deliberate effort.

So to that end, I cooked up a basic but powerful concept for an accountability group, dubbed Cotivation (think collaborative motivation), where participants would meet weekly to set goals, keep each other accountable, and discuss whatever’s holding them back.

I themed the first one around making and keeping a New Year’s resolution and published it just before the end of the year, inviting people to join for our official kickoff in mid-January (why mid-January? because that’s when you most need a boost; after the initial excitement of the new year has worn off. But also because it gave us some time to promote it).

What resulted was incredible: a dozen or so people, some existing members and some newcomers, got together and started opening up to each other. We dug deep. We talked about our hopes and dreams and what was holding us back.

We set monthly goals and then weekly interim milestones, checking in each week to see whether we’d done what we’d said we would. Inevitably, some of us would fail, which gave us a chance to examine why. We’d discuss, we’d adjust, and we’d repeat.

When the first Cotivation came to a close in February, the next step was obvious: let’s do this again. So we repeated the format, inviting others to join.

We quickly formed deep bonds. The people who participated in those early Cotivation sessions ended up being the same people who went out for drinks after work and joined our volleyball team in the springtime.

Today, Cotivation groups are running or in development in New York, Seattle, Toronto, and Fort Collins. A handful of members run their own Cotivation group at New Work City now, with new groups on the way.

I’m excited about the ways Cotivation can help independents have a sense of the crucial structure and accountability they need, while also giving coworking spaces a valuable way to facilitate stronger connections and greater value between members.

If you’re interested in starting a Cotivation group, contact me!

Quarantining new ideas for monthly review

I have this terrible tendency to flit from one idea to the next. Ask me what I’m up to today, and I’ll tell you something I’m really excited about, but then ask me again in two weeks, and odds are I’ll give you a different answer. Ask me again in a few months and I might tell you about the first idea I mentioned to you again.

In Bruce Lee terms, it’s like practicing 10,000 kicks once. It’s paralysis.

To combat this, I’m practicing developing a routine in which I funnel all new ideas onto a Trello list that I’ll make space to look at with intention at the end of each month. This will be a time when I’ll be setting intentions for the following month, so it will be a good time to look at this.

This allows me to feel good about letting the ideas go in the immediate moment, knowing that if they’re true winners they’ll prove themselves out when compared to the many others at the end of the month.

More importantly, I’ll keep the shininess of those ideas from interfering with whatever I’m working on in the present moment, which incidentally was probably an idea that was really shiny to me sometime in the past. If I can clear enough space to follow through on those ideas, execute them well, and build on them, then I’m onto something.

 

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Routine challenges

One of the main areas of professional self-improvement I’m focusing on right now is developing, refining, and, perhaps most importantly, trusting a routine.

In theory, everything that comes across my transom should be able to be handled in a consistent and predictable way. I’ve found, however, it really hard to nail that down. I think I just have to start somewhere, identify what doesn’t fit with the system, and refine as I go.

As I work towards that, I thought I’d share some things that have so far defied my attempts at systems:

  • A request from a friend to help me find sponsors for her conference. She’s a good friend, so I want to help her, but I’m not sure how to allocate time to reach out to potential sponsors for her. It seems like a painful task, so I’m not sure where or how to slot it in.
  • A friend of a friend who’s looking for a job. I’m getting a sense that this, and other things, could be batched together into a single, let’s say weekly, digest of things I post to NWC’s group and maybe my blog. It wouldn’t be much work if I focused on it for a solid hour or so once a week. I’m going to start a “Batch Favors” label as an incremental step for this.
  • A member who wanted to introduce me to someone who might want to add coworking to their space. I have some pretty good systems in place for this. I have a primer I send to people who ask my advice, which includes a compilation of questions I’ve answered in interviews and similar correspondence, and an appointment system I can direct people to for office hours-like meetings. I think, for now, this is largely a matter of trusting the systems I already have in place.

    …HOWEVER, I can’t help but feel like more can be done to better gather even just the NYC-area coworking organizers I encounter. I don’t want to obligate myself to organizing Another Thing, but… something. Another puzzle piece.

  • Friends sharing ideas for projects I’d love to do, but have no space to tackle.
    • A program for helping people get on their feet working for themselves (establishing an LLC, bank account, basic routines, etc).
    • A Welcome Center program where we create little brochures introducing people to the core communities and resources available to them in NYC (and then partnering with like-minded coworking spaces to have them offer the brochures as well.) Maybe also a paid consulting service for people who want to sit down with someone who will work with them to get them properly acquainted.
    • Lots of possible accountability / shared structure groups

This is a partial list I put together just from spending an hour going through things in my backlog. Perhaps I’ll add to it as I identify more.

Do you have a consistent way of handling things like these in a non-painful way? Help me out!

Help me put together the puzzle pieces (or stop trying)

As part of my continuing effort to revisit transparency as a general practice in my life and work, I share here an overview of the various puzzle pieces I see somehow one day converging into a more singular, focused, highly impactful effort.

It kills me not to know how to fit them together, so I am working to stop trying to figure it out all by myself. In a very short conversation I once had with Simon Sinek, he sized me up so quickly that he was able to cut me off mid-sentence and advise me to stop trying to do it all myself. So, really, I’m just trying to do what Simon says!

Here’s what I see:

  1. We have our own coworking space in NYC. We can do anything we want with it (so long as it’s legal!)— daytime, evening time, weekends.
  2. We’re friendly with other coworking spaces in NYC. And around the world. We have a growing number of like-minded neighbors whose higher purposes are in alignment with ours. We have so much to gain by joining forces, if only we can find the proper impetus.
  3. We’ve got a big lovely Meetup group. Coworking Community NYC Meetup has over 1,800 members on it and it’s growing every day. We could be having more people host more Meetups.
  4. We’ve got some really handy constructs. Work Sprints and Cotivation in particular are really handy tools people can use to externalize some structure and accountability in local communities. We also use this idea of To-DONE lists to share what we’re getting done and get a mutual sense of accomplishment.
  5. We’ve got this sticker-based social network idea. Dubbed “underground laptop mafia,” the idea is to manufacture semi-anonymous stickers that people could put on their laptops, so people could discover each other in cafes and elsewhere, look up their profiles, and see if they want to connect in real life. It could let us essentially build a distributed coworking community. Plus, it would be really cool to have a neat secret-society-looking sticker.
  6. We’ve got this new coworking network forming. My friends Drew and David, who run Conjunctured in Austin, are building Nomatik on top of the Seats2Meet platform, which allows people to broadcast where they are and find people to connect with. This could naturally fit in with the Underground Laptop Mafia idea above. But how does it fit into the bigger picture?
  7. We’ve got a new spot for charting out new ideas. I’m calling it Project Bossless. It’s a clean slate that could evolve into a more well-formed entity once these pieces start coming together better.
  8. I’ve got this crazy idea that I can’t get out of my head. The idea centers around a fictional company, dubbed Bossless Industries, that masquerades as a traditional industrial employer, but is in fact the opposite of one behind the curtain. It would serve as a vehicle for those used to full-time employment to transition into independent work without it being too much of a popped-out-of-the-matrix experience.

I’ve got countless of ideas for projects: winter retreats, mastermind groups, consulting projects, unconferences, books, and so much more. I would think the obvious answer is to “just pick one and focus on that,” but I feel like I could use a little something more. I want to feel like I’m making the right choices amidst a wide array of options.

What does this look like to you?


If you caught the very subtle Groundhog Day reference in this post, many points to you.

Act IV

This fall, New Work City will celebrate its sixth anniversary since first opening for business in 2008. It’s hard to believe it’s been six whole years; building and sustaining a small brick-and-mortar business for that long is no small feat!

The current version of New Work City, the one located at 412 Broadway, is in what I would call Act III of the overarching narrative of our story.

As we look to the future, it’s time to think about what Act IV will look like for us. Before we get to that, let’s go over how we got here.

ACT I – Jelly & CooperBricolage

Back in 2007, coworking was this obscure thing that happened in a Williamsburg artist collective and five-bedroom loft apartment on 39th Street. When I attended my first Jelly, my life changed forever. It was the first time I’d been exposed to a world of my peers who were working for themselves, doing creative work that was in alignment with their souls.

Soon thereafter, I moved into that apartment and eventually picked up where the original organizers had left off, hosting Jellies and helping others do similar. At the same time, I started working with my new friend Sanford and a bunch of other new friends on building a dedicated coworking community, dubbed CooperBricolage in tribute to Peter Cooper and Nate Westheimer’s vision of a cafe-based coworking concept called CafeBricolage, using East Village cafes as our home bases.

Between these two communities, we were able to develop a sense of consistent culture and critical mass that would be necessary for us to take the next step. Act I: Culture: Set!

ACT II – New Work City

While working in cafes was great, one can only take so many conference calls on the sidewalk before feeling some wear and tear. We needed a place we could count on to be ours. By late 2008, there was still a tremendous need for someone to build a central coworking space in Manhattan, so when NWC opened its doors, it was a boon for the people who needed it and for many who would be inspired by the example it set.

We didn’t have any investors, but we did have a lot of friends. Sanford found a startup that had more space than they needed and helped convince them to give us a chance.

We conspired to develop an arrangement that would allow us to open for business with minimal risk. With a little bit of cash and a trip to Ikea, we were in business. Act II: Business: Launched!

ACT III – New Work City 1.5 and 2.0

The space we shared with our startup friends was a fantastic incubator for what we were building. What we really needed, however, was a home of our own. Sharing space with our sublessors felt, at times, like living with our parents. Fortunately, we were able to be just successful enough with what we had there to get ourselves to the next level: a place of our own.

When it came time for us to leave that space, we set our sights on just that. After a life-saving four-month stopover sharing space with our friends at Greenspaces, a Kickstarter campaign and an overwhelming amount of support from hundreds of loving people, we got our own space open at 412 Broadway in September of 2010. We’ve been there ever since. Act III: Mission: Accomplished!

ACT IV

Next June, our current lease will expire. It gives us an opportunity to revisit why we’re here and what we want to do next. The end of this lease will constitute the end of the third act. What does Act IV look like? That’s for us to ascertain together.

As we consider what Act IV might be, I gravitate towards two main areas of focus: purpose and sustainability.

Focus 1: Purpose

Our purpose for a long time was to build and sustain a great coworking space in a central part of Manhattan. That mission is largely accomplished. So, what’s next?

Every business should be aspiring to something more. It’s no fun to just try to tread water. How, then, might we go about articulating a higher ambition to strive for?

We’ve always had a general ambition of better supporting the needs of the growing ranks of the independents. Considering the litany of things we still each have to deal with on our own without any external support, there’s no shortage of opportunity there.

New Work City as it’s currently constituted isn’t organized around working towards that purpose. It was designed to get us to where we are today. In order to develop a mandate that aligns us with the larger mission in a more specific way, we must consider how to develop a proper vehicle for that.

Focus 2: Sustainability

I very deliberately shaped New Work City into something that wasn’t to be treated as a business venture. Back when it was getting started, I thought doing so would dirty it. I wanted to see New Work City become something that people could trust to have their interests in mind, not the interest of profit-minded investors or other entities with their own agendas.

Now, as we look ahead, I’m revisiting that philosophy. A sustainable entity has a robust structure around it to ensure its vitality beyond the constraints of any one individual. NWC, as it stands, depends way too much on Peter and myself to be sustainable as a long-term entity.

So if this thing is to continue to live on in some form for the foreseeable future, it seems worth considering how we might best develop such a structure to wrap around it.

What happens next

We know that whatever Act IV looks like, it’s something more purposeful and more sustainable. That could manifest in the form of a new business entity, or a partnership with a like-minded organization, or something else we can’t yet see. What we can do, now, is take action that creates space for those possibilities to become more real.

Here are some of the things I’m currently working on:

  1. Exploring new ideas with Project Bossless – I recently launched this site to create a clean slate from which new approaches could be explored. The core of the project focuses on the emergence of the larger ecosystem that I believe coworking is a part of—an interdependent support system for people who would otherwise be on their own.
  2. Organizing IndieCon, an unconference by and for independent workers – We did the first one last fall, and it was an amazing way to rally people around finding new ways to help one another. This year, we’re planning on doing it again, bigger and better, with intention to continue building on the ideas after the conference is over.
  3. Facilitating Meetups – We’ve ramped up self-organized coworking gatherings this year through our Meetup group, which has been hugely helpful in giving us a better understanding of the different ways we can play with the coworking model. We should continue to explore how we can use this group to try new things.
  4. Talking more – So much of what helped make New Work City survive and thrive in its transitions from one act to the next came from a commitment to share and engage openly in the process as we went. The more we invited people to buy into the conversation and participate in shaping its direction, the better it got for everyone involved.

Now that the next act is coming into focus, it makes sense for us to be talking more openly about what happens next.

We know that coworking represents an important part of the future of work. As more and more people join the ranks of the never-again-to-be-traditionally-employed, the importance of coworking spaces as support systems rises accordingly.

We can’t just all be trying to figure everything out on their own. We need each other to make this shift a healthy one. Coworking is a vessel for that.

Let’s look together in earnest at how we can take what we’ve got and build on it, for ourselves and those who follow us.

If you’re reading this, you’re a part of the effort already. Comment below with your thoughts, join IndieCon (stay tuned), attend or propose a coworking gathering through our Meetup group, or of course join as a member of New Work City and help shape our future with us together.

The problem with coworking (and an idea for how to solve it)

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Coworking has served to unite millions of people around the world who share a common interest. Over seven years ago, when I was living with my parents, working from home and losing my mind, I was able to discover Jelly in NYC and a global movement with a simple Google search. Once I saw the word, I knew that whatever coworking was, it was what I needed.

Zoom way, way forward to present day, and coworking is now quickly seeping into the collective consciousness. As an ardent champion of coworking since I first discovered it, I see this as a tremendously good thing.

That growth was made possible by a simple fact: the guy who invented modern day coworking freely offered it to be taken and shared and copied and remixed by anyone anywhere. While that simple act ignited massive rallying by people all around the world, it came with one critical tradeoff: no one person or entity can control the direction or perception of the word now that it’s out in the world for anyone to use.

As a result, the meaning behind the notion of coworking has undergone an extremely long game of telephone, wherein a little bit of the original signal is lost every time it gets passed along from one to another.

Along its journey from obscurity to household name, coworking found a powerful delivery vehicle in a business model that relies on renting space and then charging people to share that space.

Over time, the deep, meaningful, purposeful power behind the word got overwhelmed by the business model. Coworking, to many people, has been reduced to simply another way of renting workspace.

Those of us who have experienced what is possible with coworking, however, know that it speaks to something far deeper and more important. Experiencing it illuminated to me the direction that work as we know it is going: away from traditional employment and even from independent models toward something that mixes the best of both.

Coworking gives us a peek way ahead, to a world in which people are empowered but not isolated. In some ways, it’s way ahead of its time.

But so long as coworking remains outside of anyone’s control, we can’t use it by itself without some additional help.

I’ve seen this in a number of stories I’ve heard and experienced myself when coworking spaces in the same city try to get together to support each other. They struggle to find ways to collaborate, because ultimately their businesses rely upon them renting space, and there’s little room for their ultimate interests to align.

If coworking spaces such as those could be united under a more specifically articulated, higher purpose, we may have an opportunity to go further.

Idea: Articulate a higher purpose people can rally around.

If the aspirations of a coworking space can extend beyond simply getting enough members to pay the rent, new opportunities for collaboration come into play. Neighboring coworking spaces have a better chance of working together, while each individual space also has an opportunity to re-cast its relationship with current and future members in the context of their shared efforts toward this common purpose.

It’s what most of us are already in the business of doing—we just need to call it out in a way that invites others to participate.

I didn’t dedicate myself to New Work City because I thought it was a fab way to make profits trading space for cash.  I’d venture a guess that most coworking space owners would agree.

We got into this business because we want to help people. We want to help ourselves, and future generations. We see a way of working that is made better when we gather and organize together.

What would it look like if we articulated, in a specific way, why we’re doing what we’re doing and started speaking and acting with that in mind?

Potential higher purposes, just off the top of my head:

  • Making your town a more welcoming place for independent creatives
  • Improving your city’s economy through increased commerce between citizens
  • Growing the number of people who are successfully working for themselves
  • Reducing economic inequality by providing low-cost access to education and resources
  • Making it just as easy to work for yourself as it used to be to work for someone else
  • Helping 1,000 people in the region make their first $100 working for themselves by the end of 2014
  • Building a support infrastructure for the emergent interdependent workforce

I’m keen on developing my own take on these higher ambitions. I want to see coworking spaces around the world working towards a shared mission in a way that’s more explicit and exciting.

How can we go about better fostering this greater sense of purpose?

 

Coworking on a train to a museum (AKA my crazy coworking experiment at six months)

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Towards the end of 2013, I found myself wracking my mind thinking about a major question that’s been bouncing around the coworking world for some time: how do we stop coworking from losing its identity to the workspace industry with which it is so deeply associated?

Coworking’s been continuing to grow into an established industry, with no signs of slowing down, but as it grows it seems to continue to lose its identity to its primary delivery vehicle: the office space rental business model.

This is important to me, because I (and many others) see in coworking so much more potential to help people than simply to allow it to become a slightly different way to cut up and rent office space.

For some reason, on January 1, 2014, I saw something I could do next from the moment I woke up. I told Amy I had an idea for what we could do now to make real progress in advancing the conversation. We immediately got to brainstorming and, shortly thereafter, I published a post entitled “27 ideas for hosting a coworking gathering that’s more than just people sitting around on laptops,” and followed up a few days later with “Crazy idea: 14 days, 14 different coworking experiences. Who wants to help organize?” — which led to the kicking off of an experiment in which I found people to lead coworking gatherings in the most diverse circumstances possible.

The objective? Develop a way to show people that coworking is about the act of gathering with people of similar interests, and that it’s NOT just about working at desks. And, further, to answer the obvious questions people have about whether one can truly get work done in sometimes very unusual circumstances.

Six months later, 13 organizers have hosted 21 events in 10 venues around the city, with more coming up. 242 people have RSVP’ed to meet up and work in places like a bed-stuy cafe that serves excellent kimchi, a wine bar with an insane sherry happy hour, the Q train, a high-rise Fort Greene apartment,  a fancy apartment in South Slope, the Met Museum, the Queens Museum, a super cute cafe in the East Village, and New Work City itself at less-than-normal days and times.

To help prove that work gets done at these gatherings, we developed To-DONE lists and challenged attendees to beat high scores from previous gatherings. The results?

People get a lot done when they gather with intention. Regardless of where they do it.

To-DONE Lists

The To-DONE list provided hard empirical evidence that people could be wildly productive in the most unexpected of circumstances.

We got work done. We got inspired. We had fun. And we formed healthy bonds discovering fun new places.

What’s next?

For one, more of everything. For example, two organizers, Nate and Jen, are now conspiring to mash up their respective gatherings to host a work-on-a-train-to-a-museum experience.

In the meantime, I am looking at how we can advance these efforts towards something more mature and sustainable. Three of the people who I collaborated with to develop events are now co-organizers of the Coworking Community NYC Meetup group, so they can schedule their own coworking gatherings now. We’re developing processes to help make it easier for current and future organizers to run great gatherings.

Ultimately, I’d love to shift what it means to be a member of a coworking community (starting with New Work City) away from one the emphasizes the space as the primary value and towards one that emphasizes the value people can generate by engaging in the act of gathering with intention.

The big challenge with that, I think, is that it’s not something that people know they and (and know they want to pay for). Space is tangible. It’s something we value. What I’m talking about is, I think, going to take some more work to prove out as a viable business model for a coworking space to successfully shift its direction.

By developing a network of sustainable, ongoing coworking gatherings around the city, we’re creating space to see how we might go about making progress in that direction.

If you’re in NYC and want to get involved, join our Meetup or consider a membership at New Work City (membership starts at $35/mo). If you’re outside of NYC, stay tuned here. I’ll have more to share soon.

Oh, and if you’re up for it, on July 9, join us as we go coworking on a train to a museum. We’ll also be visiting our friends at Beahive, a coworking space in Beacon, while we’re there.

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27 ideas for hosting a coworking gathering that’s more than just people sitting around on laptops

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A few years ago, I participated in an experiment called the Breakout Festival, in which we organized coworking gatherings in public spaces. It was awesome. I wonder what it would be like to revisit efforts to gather in new ways? Some potential gatherings, off the top of my head:

  • … go to a museum, appreciate art, then do our own creative work in the museum cafe
  • … get up really early and get a bunch done before 9:00am
  • … go on a photo safari, then settle somewhere to edit and publish
  • … pomodoro work sprints
  • … late night coworking with a DJ
  • … coffee snob coworking. meet at a high-end coffee roaster. order coffee. discuss coffee. drink. work.
  • … wine snob coworking. meet at a high-end wine bar. order wine. discuss wine. drink. work.
  • … commit to doing something you dread. do a pomodoro. reconvene. recommit. repeat.
  • … cafe crawl of (insert neighborhood here)
  • … coworking space crawl of (insert neighborhood here)
  • … coworking + drinking (infinite possibilities)
  • … coworking + brunch (no explanation necessary)
  • … coworking + saturday morning cartoons
  • … coworking + watching football games on Sunday
  • … everybody bring your pet
  • … enjoy a podcast / TED talk / etc, talk about it, then work in a way related to that topic
  • … co-workout. coworking + yoga/cardio/soulcycle/etc
  • … coworking while you wait for your stupid laundry
  • … inbox zero sprint (using the Email Game?)
  • … coworking road trip – split the cost of a zipcar, ride out to somewhere obscure and fun, work, ride back. maybe use the car time for brainstorming.
  • … coworking at a cool company’s office. fun experiences crafted around the cool company.
  • … shared interest coworking. pick a category: a particular programming language, photography, design, marketing, anything. Each person is there to work on something relating to that interest. Before starting, each person states the thing that they’re working on and one challenge they’re hoping to solve. Everyone coworks and checks back in with each other periodically to help each other out.
  • … coached coworking: one expert offers up some advice or guidance to kick off the session, then everyone works on that while they go around helping out.
  • … coworking in an Apple store until someone kicks you out
  • … coworking on a BoltBus to Philly
  • … coworking field trip: meet in a neighborhood you might never have been to before. immerse in the local culture during a group lunch break.
  • … combinations of the above

What would you attend? What would you organize? Tony

I’m going to ask you to go ahead and come in on Saturday.

Edit: Updated for IndieCon 2 for October 2014!

But Sunday… Sunday you can stay home.

OK, seriously though, I’m sick of beating around the bush. We work for ourselves, we’re on our own, and we secretly suffer from so many things that wouldn’t be so damn hard if we just bothered to open up and share with each other a little.

You haven’t done your taxes in four years? The very thought of it makes you want to crawl under your desk? Guess what. You’ve got plenty of company. Maybe it wouldn’t be quite so hard if you fessed up and found other people who were in the same boat, and banded together to commit to getting it all over with.

You’re a freelancer but you’re not comfortable trying to go out and get clients? Then when you do, you’re afraid to charge what you think you’re really worth? You’ve got tons of company there too. Maybe you can feel more secure putting yourself out there and giving yourself the respect you deserve if you find other folks to pump you up a bit.

You don’t know what the hell to do next? Of course you don’t. You don’t have a boss setting quarterly goals for you to hit. You don’t have a promotion to gun for. You’re in charge. That means you can steer the wheel in any direction, captain! The ocean has a lot of bearings. 360 of them, in fact. Did you know it’s okay to not know exactly where you’re going? Do you need someone to remind you and help you stay on course, even when all you have is your own intuition and the stars to go by?

You start work too late, work until too late, have no concept of a lunch break, weekend, or vacation? Of course you don’t. You don’t work at a job where someone tells you when to start and stop. That was the point of forgoing that lifestyle, right? But being the boss and the employee at the same time is sometimes not so easy, especially when it’s 2:00am there are so many episodes of Dexter to catch up on and nobody to remind you that you’re probably going to regret starting your workday at 2:00pm the next day.

Your client refuses to pay you? You have no idea how you’re going to make next month’s rent? You don’t really even know how you made last month’s rent? You’re worried you’re going to get sued by that crazy former client? Being able to make as much money as you want sometimes feels like a double edged sword. If you could step back from the day-to-day and stick to a plan that helps you stay steady, maybe the tumult could be mitigated.

You forgot to eat breakfast *and* lunch again and now it’s 4:00pm and you need to eat more quickly than Seamless can get the food to your belly? You don’t even want to think about health care or that toothache you’ve been ignoring? You’re wondering if you made a mistake going out on your own, because having to figure all of this out yourself is starting to wear on you?

You.
Are.
Not.
Alone.

But you might think you are, because the millions of us who identify with the above scenarios have no good way to gather and work on these things together. That’s a problem, because our ranks are growing every day as traditional 9-to-5 salaried jobs are going away and opportunities for us to make a living doing things in different ways continue to grow.

The fact that so many of us can be in charge of our lives now is awesome. But if we learned one thing from Spider-Man, it’s that with great power comes great responsibility. It sucks to have to figure all of this out ourselves.

It’s time for us to change that. I’m hosting a brainstorming session on Saturday, September 7 to gather independents to share their best practices for how they manage their lives, and to learn from each other. But I’m also hoping to have a bigger conversation about how we can organize to support each other in ways that we would struggle to do on our own, while still preserving and reinforcing the independence and freedom we value so much.

Could we have a replacement for a 9 to 5 without feeling like we’re dragging ass to an office every day? Could we replace the idea of management, bosses, quarterly goals, or any of the other things that we kind of hated about the old office but now maybe kind of miss a little?

I don’t know the answers, but I do know the questions are ones worth asking. Let’s ask some questions and play with the answers.

 

IndieCon – An unconference for independent workers!

Saturday, October 18 from 9:30am to 6:30pm

Location: New Work City – 412 Broadway, Floor 2, NY NY 10013 (map)