In the early days of my 5-year experiment with semi-retirement, I brainstormed ways it could fail. I worried that I might end up too distracted to make useful stuff, or that I'd end up being incapable of pursuing my ideas, or that I'd mess up somewhere–paperwork, people, products–and botch the whole thing. I worried that I'd finish the experiment with nothing to show and no compelling story for the gap I'd have in my resume. I worried that W- would get tired of this exploration.

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I feel less worried now. Part of it was realizing that I can plan for only so much safety. Part of it was learning how to choose what I'm going to focus on, how to select my projects without managers and track my progress without annual performance reviews. (Well, I still have annual reviews, but they're self-driven.) Part of it was trusting that I can handle things, a confidence which grew after each small step.

Looking back, I can see the things I found mentally challenging in the beginning, and how I worked around them.

• The career gap doesn't look all that scary now. I know lots of other people who have managed it. They're fine, and I'll be fine too.
• Self-direction turned out to be good to learn, and it seems like I can come up with useful projects.
• Paperwork? There were a few stressful hours as I learned more about the tax code – I amended my first corporate tax return a number of times – but I think that doing my own books was worth it. Besides, Canada Revenue Agency is surprisingly approachable. Hmm.
• Opportunity cost? “Wasted potential” only

2014-02-21 What did I find challenging when I started #experiment

If you're starting your own experiment or you're well into one, I'd love to hear about some of the challenges you faced and how you worked around them!