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Ask: Stigma of the unemployed - a better job title for a lifestyle entrepreneur?
41 points by dubeye 1512 days ago | hide | past | web | 48 comments | favorite
I run a small, unsexy internet business in Europe, with a two person office and about 20 people working from home.

Around here, 'entrepreneur' is assumed to mean 'unemployed' or at best 'freelancer'. I'm dating at the moment and find it difficult to succinctly describe my occupation in a way that does not kill the conversation dead, as it either comes across as bragging or an attempt to disguise unemployment. It's major taboo here to talk figures or numbers.

So any ideas for pithy ways to describe a happy lifestyle entrepreneur without coming across as defensive?




> I'm dating at the moment and find it difficult to succinctly describe my occupation in a way that does not kill the conversation dead

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.


Why not simply say 'run a small company'. Nothing says 'success' like success, I'm assuming that your company actually works and makes money. That's as good as any employment or better depending on how well you're doing. Any date that just wants you if you have a steady job is not worth having imo, then it's no longer about you but about a search for financial stability.


I wonder about this. Why can't a person have some criteria to narrow the pool, and from that subset select for love? It would be different if they took the first person who came along with financial stability, if that was the only thing that mattered.

If a person aims to have a family, financial stability is important. Note, I don't believe that kids actually need financial stability all that much, but the stress and conflict between parents commonly caused by financial instability definitely do affect them.


Financial situations that are attributable to state of employment are subject to violent and sudden change. They're not a good basis for any future predictions, especially not for viability of a relationship.


> I wonder about this. Why can't a person have some criteria to narrow the pool, and from that subset select for love?

Pretty much everyone does (whether they are explicit or not), and pretty much everyone resents potential partners that do, to the extent that they end up getting weeded out by the filters.


'Run a small business' is a great phrase to test.


Well, i am from Eastern Europe too, and my business can be best described exactly as yours, and i don't see absolutely any stigma. Everyone is ready to accept that running a small business is way better than working 9-5 for a meager wage.

Maybe in U.K. or Germany it might sound as 'unemployed', but in Eastern Europe 'employed' almost always means 'poor loser' unless you work for a big name company (SAP/Gazprom) or at least a mid-tier manager. So, there is more stigma attached to employment than unemployment. In fact, many people just tell to girls 'i don't work' and that adds to their image rather than subtracts. Remember old Soviet curse "i wish you live on your salary alone!"

If you feel bad telling you don't work 9-5, buy a sports car. It helps.


I used to pitch myself as a freelancer/entrepreneur/self-employed. Lots of women were not interested, and that was good. I found one who bought that that my status was cool, was supportive, and we ended up getting married after a few years. Just had our 25th anniversary.

Be who you are, and if women don't like it, they're not a good fit. Bullshit now comes back to haunt you later.


"Be who you are, and if women don't like it, they're not a good fit. Bullshit now comes back to haunt you later." These are extremely wise words to live by.


I run a small software company which $BENEFITS_STATEMENT.

You can tailor the benefits to whatever you thing the person you are speaking to values.


Did you A/B test those kinds of statements with girls prior to getting married? :-)


No, because dating a statistically significant sample of women sounds dreadfully expensive and conversions would be too slow to get results while I was still young enough to use them.

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."


You should also consider an MVP approach. What is the minimal viable product I can entice these customers with? I mean... what is the least I can do in order to get laid as quickly as possible?


HA! Yeah, that's what I used to use.


Can you give us some good, non-awkward-to-say, benefit statement examples?


If you ever feel awkward saying something, trying saying it like the Old Spice Guy would say it. It seems to me this often makes things almost magically less awkward.

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.


Good advice. A confident delivery is often more important than the words you used.

I didn't feel that confident about my work in the first year, now I do. I say the same thing to different reactions now.


Old Spice Guy, or The Most Interesting Man In the World also works.

"I don't have many customers, but the ones I do, are satisfied."


I am Italian and have been an entrepreneur myself, for this reason, I understand your difficulty.

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 <your business goes here> 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.


Definitely. If it were a dating game, I'd almost go with 'I don't have an employer, I'm really passionate about software though' and leave it there.

girls.filter( girl => !girl.isGoldDigger ).map(_.reply("how about you?"))


You don't have to use the "entrepreneur" label. I don't, but mostly because it sounds stupid. If you run a popular media site, you're in the media business. If you sell e-books, you're a publisher. If you run a time tracking SaaS, you're a business tools provider, software engineer, productivity expert, whatever.


I am co-owner of a company that make children games.

When people ask what I do, I say: "I make children games."


I do consulting in quantitative software and analytics for finance. I have my own small company and can give myself any title. "CEO" sounds too pretentious to many, so I went with managing director, the title for upper-middle to upper management in many financial companies.

Choose something similar for your industry. Couple of guesses: vice-president of business development, director of professional services, executive producer...


That's funny, since in Commonwealth-speak managing director means CEO.


Business owner? Businessman? Or maybe it's the way you talk about it. I'm from Europe too and I'm not aware of this phenomena. Maybe the translation for that in your language has some other connotation or evokes a different feeling. In my native language we have a word for that too, but to be honest it feels completely different.

Anyways how does that kill the conversation? -What do you do for a living? -I'm an entrepreneur. -Ohhh, I see. I have to go now, bye! A bit odd.

Anyways - optimize for quality rather than quality. Having everyone fall in love with you is pretty crap if you don't like them back. You need just one.


I guess in SV the coolest is Founder and Investor, then Board Member and Advisor, but we still have CEO, CTO, Exec, etc. followed by standard positions like Distinguished Engineer, Senior Engineer, etc. and generics like partner, associate, and employee. VP isn't worth much since some industries use them at very low level.

If you can't call yourself a founder, or it doesn't go over well in Europe, what's to stop you from just saying I work for company x. No one knows it is a two person company + outsourcing anyway. It's the same as saying I work for amazon, etc..


"I own a business." Oh? What kind? "We make X for Y."


Just tell that you run a business. Most people who you don't want to be confused with (who actually don't do much and are business wannabes) wouldn't tell that about themselves. They “are entrepreneurs” in state of their minds and in their daydreams but they don't run any business. Actually, most of them think that “being an entrepreneur” > “simply running a business” so they wouldn't lower themselves to claiming that as they always aim so high and want to feel so important, right?


I got this from some older friends when I started DataStax. They took my wife aside: "Sure, Jonathan's 'starting a company.' But seriously, do you need help?"


Just tell people "I write software for x" where x can be anything. Teachers, government, hospitals, dogs, whatever it is. In my case it's "lawyers". You don't have to go into any more detail than that. Anyone who really cares will ask followup questions or say something like "oh you should talk to my brother, he's a lawyer".


Have pride and confidence when you speak of being an entrepreneur. Dammit, you're an innovator! A job creator! A creative person! With a variety of skills and challenges! You love what you do! You're a risk taker! You're your own boss! You are in control of your future and you are doing exactly what you want with your life!


There is no magic word, just say it confidently. And just hint at it, more can come out later. Mystery helps.

Though I think sprindrifts suggestions are better. If they're truly Iinterested in knowing they'll ask again later and you can respond seriously.


Honestly any woman is lucky to find a decent guy who has this kind of work. Mainly, because you'll have a lot more freedom and probably be able to spend more time with her than 9-5 slaves.

If they don't bite, then it's their loss. Good luck man.


Why don't you just keep it simple ?

You: I run my own business

Girl: hmm what kind of business ? (or she might just stop here)

You: Online business to sell $XYZ

Girl: Oh cool. <She asks another question about the business>

You: Well yea its kinda complicated. So what were you saying about that tilapia ?


Give yourself a title, like CEO or Director, of the company. Don't call yourself an entrepreneur, just a simple, but nice title.

You don't need to defend something that definitely works for you. Be proud, but not arrogant.


"I work online" is my go-to, it gets around the 'Im an entrepreneur aka out of work bum' trip wire that even I look out for, and leads well into a description of my service biz.


You're a CEO, a business owner and your own boss. I'm from eastern europe and maybe things are too different here, but I don't see how that would ever mean unemployed.


instead of saying you're an entrepreneur, say what you do. for instance:

blogger = author

information marketer = teacher

outsourced app = product designer

affiliate marketer = international sales manager

ecommerce store = ceo of import/export business

and so on


Some of those are deceptive. Nobody would mistake an information marketer for a teacher (One has a stable job educating a classroom, the other sells overpriced weight loss ebooks.). And international sales manager is a huge stretch from affiliate marketer.

Honesty is the foundation of a successful relationship. So when dating for love, you should always tell the truth. If you own a business, say you own a business. If your date can't accept your career, then they aren't worth dating in the first place.


>Some of those are deceptive.

All of those are deceptive.


Obligatory Seinfeld reference: https://www.youtube.com/watch?v=IrLtHatB6IU


I don't know what country you are in, but in Germany, the Mittelstand is a quite respected part of the economy, and that describes what you do.


I do what I want, when I want. Right now I want a sandwich. (Insert long pause and do not speak again until she gets you a sandwich.)


Obligatory manhood reference: http://manhood101.com/


Businessman/woman? Executive? Director? Founder? Cofounder? Go with something they're familiar with.


State what you do. Don't look unemployed.

Some can't take a spouse with unsteady income. That can't be helped.


what is your job title at the unsexy business? manager of sales, VP of sales, programmer? choose one and move on. if the person asks for more info, they you tell them what you do, just leave out of the entrepreneur thing.


startup founder is well understood in Europe...or MD of one




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