“So, what are you going to do?” That’s always what people ask after I tell them that I’m leaving IBM in order to experiment with entrepreneurship.

“I don’t know yet,” I say. I explain that I haven’t yet experimented with anything that could be seen as competing with IBM, following our Business Conduct Guidelines – and that covers so much ground. I’m leaving without a solid business plan or a proven opportunity, just itch and curiosity and the sneaky suspicion that there’s probably at least one business that I can build considering how others have succeeded.

The first thing I’m going to do after I leave is to create a structure for experimenting. Despite the associated costs and paperwork, incorporation makes sense to me. Limiting the downside – building that part of the safety net – makes it easier to experiment.

How can I go about testing possible business ideas? There are some conventional things I’d like to try.

Writing: I love reading and writing. If I can combine that with drawing and design, maybe I can create engaging e-books that will help people save time and be inspired. People have earned money from information products, so this has worked for other people before. Some have even succeeded without sleazy marketing tactics and without preying on people’s greed, which is encouraging! =)

I can test this by researching topics I’m interested in, writing blog posts and chapters, and eventually building up to e-books for things that people might buy. I’ll be writing notes anyway, so I may as well invest time into making them more usable for others.

Coaching: I’ve gotten so much value from writing, presenting, and experimenting with life. People find these things intimidating. Maybe I can help build scaffolds so that people can gradually try things out, succeed, and then gain enough confidence to do things on their own. (And I can write about what we learn along the way!)

Self-tracking: I like the results I’ve been getting from tracking my life, and I’m curious about building and tailoring tools for other people’s lives. Can I turn that into a recurring source of income? We’ll see.

Sales and customer relationship management for development: Quite a few developers have told me that they don’t particularly enjoy this part of freelancing, and it’s one of the parts I’m actually the most curious about. Maybe I can get started by helping my friends take better care of their clients and leads, and then see if the arrangement works out well.

Community analysis tools: Considering the success of the Lotus Connections toolkit within IBM, it might be interesting to make it more available to other companies. Right now, some of the functionality is available externally in a plugin for Lotus Notes, but things are still difficult to adopt. If I write a new implementation from scratch and I build the tool based only on externally-accessible information, that might be okay. It’s been quite a useful service within IBM, and it would be great to share it with more companies.

Testing ideas: How meta is that? If I’m going to be testing lots of business ideas and possibly working with other people to help them test their business ideas, then it would be great to gradually build processes and infrastructure for doing so.

Freelance consulting and development: I want to focus on the other initiatives first before I get into freelancing. I’m reasonably confident that I can figure out freelancing (especially with a little help from my friends). The kinds of work I’m considering (consulting, web development, technical writing, data migration) are similar to my work at IBM, so there’s less uncertainty to resolve. Custom work often means fewer opportunities to build compounding value, and I’d like to see if I can build a business that can scale up beyond my time.

I’m looking for things in the sweet spot: the intersection between what people need, what I’m good at, and what I love to do. If you’ve been reading my blog for a while, you’ve probably picked up a good sense of what I’m interested in and how I might help you (and lots of people like you!). Is this list missing something that would help you even rock more?