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?


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)

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