“What’s the most challenging part of working for yourself and how do you work through this challenge?”

I was recently interviewed by Laurel Staples of the Go Fire Yourself blog. I really dig her site and her approach to encouraging entrepreneurship. One of my favorite questions from the interview was:

Q: What’s the most challenging part of working for yourself and how do you work through this challenge?

A: I think the biggest challenge is time management. When you have partners, employees, suppliers, customers, etc all vying for your attention things can get hectic. It can be tough to prioritize what’s really important vs. what’s being presented to you in the moment. At the end of the day I don’t want to be putting out fires and not accomplishing anything to help grow the business. I also want to have plenty of time to relax and enjoy life outside of work!

I approach this a few different ways. First is limiting unnecessary communication. I’m vigilant with my Gmail filters to keep anything unimportant out of my inbox. Programatically, we’re continuously automating more and more on the back end with our vendors, and giving our customers more functionality to empower themselves so that our overall email volume goes down. And we frequently discuss the importance of choosing the right form of communication at our company meetings. An email is passive and can be addressed whenever I have time. A Skype message or a phone call interrupts me. Knowing when to interrupt someone and when not to is something we’ve gotten really good at.

I also make sure I stay organized on my end. I use Remember The Milk to manage my to-do list. Any recurring tasks go on there. Appointments go on my Google Calendar. Programming plans and project plans are in Google Drive. Each weekend I try to spend a few minutes outlining my objectives for the week. Each night I try to do the same for the following day. Those exercises keep me focused on what’s important when things start to get crazy. They also set boundaries for me. If I happen to have a chaos-free day and get everything done earlier than normal, I generally take the rest of the day off instead of starting on something else. It’s rare to get a day like that, so when it happens I chalk the day up as a win and enjoy my free time.

You can check out the full interview over at GoFireYourself.com!

1 comment on “What’s the most challenging part of working for yourself and how do you work through this challenge?”

  1. It was such a pleasure to feature you on GFY and I love the way you answered this question. Time management is so critical when you work for yourself and I appreciate you giving insight into your own life about how you handle it. Great post!

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