Ask: Stigma of the unemployed - a better job title for a lifestyle entrepreneur?

However, before even trying to describe your lifestyle in a less defensive way, I would suggest to change attitude about your job.

Far from being a stigma, running a small business makes you a successful person if you enjoy what you do, if your business is stable, if it grows organically, if it allows you to employ people, if it leaves you time to live your life fully.

Saying "I am an entrepreneur in the field" should be convincing enough if you feel strong about what you are doing.

After all, if you feel strong about your choices, anyone who kills the conversation at this point might not be someone you want continue dating anyway.

Sorry, I'm a bit literally minded. OK, so did I try saying different things to ladies to see how they reacted? Yes.

What worked very poorly: self-deprecation ("I'm gainfully unemployed"), describing myself as an engineer, and minimizing my accomplishments in starting a company. What worked very well: focusing more on the benefits of software rather than on the "software" bit, leaving a bit of ambiguity about what I actually did for a living, and mentioning things which "normal people" tend to associate with successful businessmen. (e.g. It was, at one point, equally truthful to say "I do A/B testing" and "A firm in Germany recently flew me there to speak to the CEO about what they would need to do to increase sales by a few million dollars." Try asking young ladies of your acquaintance to rate the attractiveness of two friends with those occupations.)

I got radically more successful with dating after I treated it as a marketing exercise and realized that some scripts I had internalized about it were the dating equivalent of "Good products always win so just focus on product quality and that obviates your need for a marketing strategy."

My answer around techies is different and generally focuses on tech-centric social proof, but if I were e.g. at a McKenzie family reunion where capitalism is vaguely distasteful and teachers can do no wrong, I would bang the "I helped teach X million kids a reading lesson last year" drum pretty hard.

As a general rule, don't answer questions like that straight. They're bound to kill the conversation, you're not at a job interview.

Jewel thief ("casing the joint" if it fits), duck cleaner (watch dirty jobs), art forger ("-- Really?! Can you draw something for me? -- No, that would be original art.")... will all go over much better than whatever your real occupation is.

It's the same with age ("64, hanging in there! Just 8 more months to retirement. Great genes though, right?"), where you're from, what your hobbies are... The difference between lying and flirting is that the embellishment should be almost obvious.