Setting goals to avoid feeling set adrift

I’ve taken quite a hiatus from Simpli recently, going from working 8-10 hours a day to working 1 or 2. I did this for several reasons, but mainly because my identity was wrapped up in my business. I was having a difficult time discerning what I wanted in life because my life was my business. After 6 years of running Simpli, and 4+ years of running it full-time, I decided I needed a break to figure out who I really was.

That break has been everything I hoped for, but at the same time has presented a host of new challenges that I wasn’t expecting. I figured I’d spend a significant amount of time working on new ideas and completing goals, such as learning a new language and learning how to fly a plane. That part has been fulfilled (I’m working on Spanish and taking classes on how to fly a Cessna.) What I didn’t expect was the emotional rollercoaster this put me on. Suddenly I went from working all-out, all the time, to not working much at all — in the space of 6 weeks. Instead of the expected excitement at having all these new things to do, I found myself depressed and “floating” — treading water and not feeling motivated to get out of bed at all. I watched a lot of TV and found that rather depressing, too.

After struggling with this for quite a while, I came to the realization that what was keeping me afloat at Simpli was that I worked every day toward goals — keeping customers happy; growing the business; managing my employees. Each of these presented new challenges on a daily basis. Every day when I woke up, I had a ton of problems and ideas to work on. Granted, a lot of these made me stressed out and sometimes an emotional wreck. But what I could count on was getting up and knowing there was something I could do to make people’s lives better in some small way. That is, after all, why I started Simpli.

Suddenly my focus had been shifted from “How can I help others as the CEO of Simpli?” to “Wow, there are a lot of hours in the day and I don’t really know what to do with them all.” This put me in a bad feedback loop of boredom leading to frustration. My brain seems to be wired to solve problems, and when there aren’t any problems to solve, it just gets depressed. I had some vague goals, like “Write more in my blog” and “Learn a new language”, but I hadn’t defined them in any meaningful way. There weren’t any real problems to solve there.

Eventually it dawned on me that what I needed to do was exactly what I did when I first started Simpli. There were two things I wasn’t doing:

1) Defining my goals as clearly as possible, with problems to solve and dates to achieve specific goals.
2) Working every day in some small but meaningful way to get to those goals.

When I started Simpli, my goal was just to work every day on Simpli in some way. Whether that was answering support tickets, promoting the website, posting ads for our hosting services, or even just writing +5 posts on Slashdot with my signature enabled, I did something every day that would make Simpli more valuable. That persistence paid off, and 6 years later my single $15,000 investment turned into a $1.1MM company.

Now I have to plan to do the same thing, but with my new goals instead of Simpli. I will post a new blog post here soon that will show my goals for 2008 and farther out, and how I plan to work on them. More importantly, since I now know I need to frame my goals in terms of problems to solve in order to keep them interesting, I’ll have more information on the problems I intend to solve as well. You can help me track my progress through this blog, since I enjoy sharing what went wrong and what went right. Finally, a short-term goal I have is updating some previous blog posts to answer the emails I get that say “What happened with…?” I’ll have that soon as well.