I am a lot like you temperamentally and currently homeless, though the two things are not really directly related. I have thought a lot about it over the years. For me, part of it is that I was one of the smart kids in high school and got a lot of not subtle messages about how I owed the world benefit for my gifts and would be evil incarnate to try to, gasp, get rewarded for them. For me, I think gender also plays a role. I am female and a lot of my strengths have a social element which is routinely treated by other people like I owe them some free motherly love, I should be a total fucking martyr about it, and, to add insult to injury, making people feel good is not some sort of intelligent, valuable skill set or knowledge. It is treated like I am just cute and lovable like a tribble.

I have my own ideas on how to solve these issues for me. I sm not giving you advice here. Just saying it resonates, fwiw.

I would recommend not being so open and candid, emotionally and concerning life events, on the internet. This is doubly true when your handle is linked to your photo, location, and real name.

I wouldn't hire you for freelance work due to your seemingly incredibly unstable situation.

Thank you for your concern. As is typical, off the cuff advice about something you know almost nothing about isn't going to be useful to me. Your remarks smack of jumping to conclusions, probably very erroneous conclusions. Arguing about the particulars is not likely to do either of us any good but I am also not comfortable letting your characterization of me stand. Suffice it to say, your opinion has been noted and I plan to continue to be emotionally open as well as open about my life. My financial mess is getting cleaned up. I am clear I am on the right track.

I hope you have a great day. The world would be a better place if more communication came from a place of concern for another person's welfare. I hope you do not stop caring about other people. Although the road to hell is often paved with good intentions, I believe it is usually due to good intentions combined with poor execution. I think execution is easier to fix than a cold heart.

Take care.

It's worth a lot, and while I am not female, and can't fully empathize, I would like to say that I at least sympathize and that I see and try to speak against what you are describing. Women in particular seem to be taught not to profit. In fact, I think on the other side of the equation it is part of what has been awkward for me. Many of my closest male friends see profit as part of their self-identity and it wasn't until your post here that it clicked for me that it may be related to gender identity.

So, like I said, worth a lot. And making people feel good, caring for people, it's the most valuable skill so far as I'm concerned. Glad there are other people who value it.

My situation is complicated. I am not making much money but I am "saving" millions kind of by not being sick. Long story. So can't really be too terribly unhappy about it. At some point, the dough will role in but I will know I am doing stuff I am okay with...etc...

((hugs)) & take care.

Now that's interesting. Please do share more about your disposition away from revenue. What does that mean to you?

I'm trying to think how to explain it without using anecdotes, as I want to understand it myself without punting to simile. I know that I undervalue the importance of money in my own life (I have been poor to the point of homelessness once, poor the point of selling possessions to get rent/food money a few times). I also undervalue my worth, almost never charging an appropriate amount for my time.

I've cultivated a niche expertise that I translate well to a wide range of communities, but when asked politely I tend to give my time and even tangible goods away for free.

Now, I'm actively trying to change that. I'm getting married next year and am very excited to have a family in the relatively near future, so I'm paying off debts, I re-entered the workforce at a decent salary, and have been trying to train myself to be comfortable asking people for money in exchange for my time & expertise.

It has been harder than you might imagine, but I'm making progress. Being able to externalize the need to earn money via the idea of a future family has helped me, but I remain very uncomfortable asking and often find myself under-reporting hours spent, transportation costs, etc.

If I could just produce content, conduct research, give workshops & lectures & have someone else handle the money, I would be in heaven, but the few people I've spoken to about it, despite initial enthusiasm, have never followed through. Considering my own disposition, I obviously don't blame them at all :)

emhart This just went on HN front page: http://blog.quoteroller.com/2013/09/19/uncomfortable-convers...

I read your comments here and then I saw it. I think it is a sign :)

Seriously, I am not sure this aproach will help you. It looks like to me that it is more about "why do it" than "how to do it". I think what you should do is put yourself in a position where will just assume you will charge for it, so you don't have to say "oh, I would like you to pay for that".

But that wouldn't help with you refusing to charge for long hours. But you may consider a transparent aproach for it. Why not sending an email asking your clients if they feel confortable with you charging some extra hours. If they complain, you don't charge, but I guess some may accept it and even enjoy if they are rewarding a good job. This way it is no more a binary "I don't charge and they never know/I charge and they don't like it". There is a dialogue about that may substitute any confrontation.

I appreciate you sharing the link, I missed it on the front page. How fitting! :)

And I also appreciate your thoughts. Thank you.

I am like you. Recently, I was given the advice (by someone who the advice was working for well) to hire a business manager. You do what you are good at (producing content, conducting research, giving workshops & lectures) and they manage the business. You need to be able to trust them, but assuming you can find somebody like that and afford to pay them, it makes a lot of sense. Perhaps there should be an app for that (outsourced business management??).

Best of luck to you :)

I'd love to! But, the 3 people I've approached about it so far have all failed to work with a single lead. Literally I'll forward them an email asking me to come speak somewhere, and they never communicate with the person or me about the work again.

If anyone on HN wants to start a speakers agency for tech/security folk, I'd be first in line to sign up :)

I'm interested in your need - in your example, you have a verified, paid speaking lead and you need someone to line up the work for you, get it billed, maybe find you other leads, what else? I'm not going to promise anything other than to think about your need and see if I can come up with a simple solution (I have an idea in mind). If you'd like to email about it, send me a note - noj AT dimensionsix.com.

Relevant new Wondermark comic: http://wondermark.com/969/

The person asking you politely for free work is probably someone good at sales and manipulating people. In other words, you aren't doing them a favor. They see you as a sucker. You sound like a nice guy, and everyone assumes most people are like themselves. But in business there are tons of wolves in sheeps clothing. The line of people who will take advantage of you will last longer than your life on earth. So you have to learn communication, and learn that you bring value and they should pay what they agreed to pay. Invoice them for the full amount, and don't give them any freebies unless either they complain (even then they need a good reason), or at the very least they have to know that you are trying to do them a favor. If you do free work and they don't even know about it, you have just shot yourself in both feet. You remind me of me. I speak from experience. It's not easy, but it is worth it.

Hey, halfcat, I hope you revisit this thread and see this, but you are apparently hellbanned (only those of us with "showdead" on can see you. I actually can't imagine why, your comment history all seems pretty reasonable. Anyway, figured I'd leave this here to let you know. Good luck.

Also maybe read some of Ramit Sethi's stuff. He has a book and tons of stuff on his website and YouTube.

Not the OP, but I can put forth that perhaps it's an ethical dilemma? Objections could be raised to collecting money without expending effort. Similar to objections to copyrights that last indefinitely.

I do think that it has some sort of knurled ethical/moral center in the middle there. It's definitely an emotional response, but logic & emotion are at odds on this one for me.

That's a cool idea and I made only 1/3 of that.

Made about $200-$350 every 3months investing no time at all. Last year I started feeling bad, because I didn't do anything and made the menu free. I wanted to sell other stuff, but never had the same motivation to be honest.

I made a menu for a customer, then decided to sell it for $1, but the system didn't allow that (no micropayments). So I just made a dozen additional colors of the menu using Photoshop and sold it for $15 for 2y.