Why Working for Yourself is Hard

One of the things I’m learning right now is how to work on my own projects. I think starting a project for yourself is challenging in a way that doing work for other people is not.

We tend to grow up doing work for other people—teachers, parents, friends, employers. This has the benefit of accountability built right in. When someone is waiting for you to do something, you’re more likely to do it. It also has the benefit of someone else giving you specific requirements and tasks. Someone else defines the vision for the end result and makes a lot of decisions for you so you can focus on simply doing it. I think this is why so many companies are organized into groups of decision-making leaders and groups of people who carry out the decisions. It’s a lot to handle for one person to do both tasks at once.

But, if you want to do your own projects independently, you have to figure out how to work without those benefits. You have to make decisions for yourself, and you have to create your own accountability.

One way to do this is to get a partner. Either a collaborator, or someone to serve as an editor. Someone you can talk with regularly to create accountability and get feedback from regularly so you have opportunity to share and improve which is essential to any project. In fact, I think it’s rare that any creative project gets done completely independently.

One way of making decisions is getting really specific about tasks and limiting the scope of your goals for each time you work. When I’m working on my own projects, usually my to-do list ends up looking like “Work on Project X.” But that’s way too vague. It’s not specific enough. You have to decide what specifically to work on, and that can be really hard. But by deciding on a specific task you can complete in one working session, you’re more likely to make real progress, even if there’s still a lot of uncertainty about the other parts of the project. Vague tasks are much more likely and can even be helpful at the beginning exploration phase of a project. But eventually you have to make a decision and get specific.

In this video, Leo Babauta talks about how he works. Leo is someone who works for himself, and I was struck by how specific his tasks are. They sound just like tasks I have at my job. Instead of “Work on Project X” the tasks are “Write the appendix to Project X” or “Send manuscript to the designer.” If you’re not specific enough, you’re not really in the middle of the project. You’re looking at it from far away and not sure how to approach it.

In another video he also talks about how he created accountability for himself by creating an “alpha tester” group for his book (which I thought was a great idea) and enlisting the help of an editor.

This is something I’m learning and re-learning every day. Thanks for listening to my thoughts about it, and let me know if you’ve had a similar experience or other thoughts about the challenges of working on your own projects – I’m on Twitter.


About Kevin McGillivray

Kevin McGillivray is a teacher and web developer from Wisconsin. He writes about creativity, mindfulness, code, and tea. He is the co-founder of Sandcastle, a tiny studio.

See all posts

Subscribe to the newsletter: