Today in “WWYD,” one of our favorite topics: tipping. And learning to be assertive.

I’m curious about how to tip when something has been removed from your bill. I went out to breakfast with a friend and my food came out the way wrong. Without saying anything to me about it, the server kindly removed it from the bill. I left the tip for our table, and left him 40 percent, which seemed reasonable as I was leaving it, but when I calculated it more precisely at home, I realized that I only tipped two dollars more than what his tip would have been if my food were on the bill. So now I’m concerned that I low-balled him.

Do you have any guidelines for what I should do in the future? I want to be generous to someone who has been generous to me, but if I’m being honest, I guess I also don’t want to pay back the entire cost of the bad food in the form of the tip. Or would that be the best thing to do? — M.

Perhaps our readers who have worked in the service industry can help me out on this one, but it seems to me that if you really want to be generous to your server, the thing to do is, well, tip generously. Generally, when you get comped items, I think it’s a good idea to tip as if your bill wasn’t comped at all, which is what you did. Continue to dine at that restaurant. Be kind to the servers, and tip generously for the great service. That’s the best thing thing to do.

Just over a year ago, I was awarded a scholarship for students in my area of study from a community foundation in my area. The scholarship fund is supposed to give me $500 per semester for the remaining years of study. I received the award no problem during the Fall semester of ’11 and Winter of ’12. Then I took the Fall semester of ’12 off. Now I’m back in school, and there’s been no indication that I’m getting the $500 this semester.

The last time I spoke to anybody at the foundation, it was early August of last year and I was still planning to be in school that fall (and graduate in December). Since they were waiting on my enrollment certification to send me the money (I have to be in school full-time to be eligible), I figured they just didn’t send it that semester, since they never got my enrollment certification, because I didn’t enroll. I sent them my enrollment certification for this semester, once I went back to school, and assumed that would set things in motion for me receiving the award again.

But the money hasn’t come, and I’m feeling super guilty because I have been really bad at communicating with these people—I never told them I was taking the semester off—and I want the money because I’m a poor college student and I could really use it (and, you know, I was awarded this scholarship and everything). But I really don’t want to write to them and ask because the whole thing is going to be me saying, basically, “Um hey, remember me? You gave me a thousand bucks and then I kind of disappeared and didn’t send a letter to the trustees updating them on how my education was going even though I promised I would do that? Well, I’m back in school now and I would really love it if you would keep giving me money, ha ha!” I’m going to be graduating in May—finally—and I won’t have to deal with this again after this year.

Do I avoid the humiliation and never ask for the money and remain quietly resentful of them and myself? Or do I risk it and write them a nice letter and explain what was going on and see if they got my enrollment certification for this semester? The answer is SO OBVIOUS when I write out the question like that, but I am just really bad at asking for things I want, especially when I feel like it’s my fault somehow that I don’t have the thing I want. Also, how do I write this letter? — N.

So even though the answer to N.’s question is obvious and she basically answers it for herself, I wanted to post her question in full to show how helpful it can be to write out a problem you’re having and examine it on the page. Yes, clearly N. needs to get in touch with the foundation and get this all sorted out. And the easiest way to go about doing that is to pick up the phone and track down a person who can help her get this matter cleared up: “Hi, I’m a scholarship recipient and haven’t received my funding for the current semester. Can you connect me to someone who can help me?” Once you’re connected, explain the conundrum, just as you described above.

It’s hard to be assertive if you’re the shy, non-confrontational sort of person—the sort of person who over-apologizes for things. I know because I also tend to lean in this direction. But I’ve also learned that if you don’t assert yourself and ask for things, you lose out. I saved myself a lot of money by asking for more financial aid when I was in college. I asked for and negotiated a smaller broker’s fee for the apartment I currently live in and saved myself $1,000. And as Rebecca says in her Craigslist piece today, you’d be surprised by how much you can save simply by asking for a discount.

I’d skip the letter and pick up the phone. You’ll get this resolved much more quickly.

Email me your WWYD experiences to me with “WWYD” in the subject line. See previous installments.

I’ve been fortunate enough to spend the majority of my twenties traveling across five continents and temporarily living in some of the most exciting cities on earth: London, Los Angeles, and New York City—with long stints in Paraguay and Belize. I’ve been able to afford this, not because of a trust fund, but because I rarely have to pay rent. Before you get super excited about reading this article and fantasize about all the places you’ll jet off to, let me explain that I have made almost the equivalent of no money. I’ve learned to be savvy. The trade-off for my wanderer’s lifestyle has been that I’ve never owned a car, maintained a rental lease after college, bought furniture (maybe a table, once) or seriously thought about having children. My bills consist of student loans, a smartphone, health insurance, and a subscription to a streaming yoga website. I don’t own much besides my laptop, camera, and clothes that would not be considered business casual. Still, for anyone with insatiable wanderlust, check out the following ways I’ve traveled on the cheap:

Scholarships
Back when I was in community college (I’m serious about having no money), I got a financial need-based scholarship to study James Joyce in Ireland where I encountered a lot of retirees who had a difficult time walking uphill and seemed slightly afraid of the Irish. I vowed to travel while I was young and work while I was old. A reverse retirement, if you will. If you’re in college or graduate school ask the financial aid office about scholarships for study abroad programs.

Moonlight
Coat check attendant. Babysitter. Waitress. Author’s assistant. These are all unglamorous jobs I’ve logged thousands of hours doing. In Los Angeles, I made a few grand working as a temporary nanny (while the stay-at-home mom recovered from surgery) and used the money to check out art museums in Buenos Aires and the beach scene in Uruguay. Craigslist and asking friends for connections seem to be the best way to find short term, cash paying gigs between trips.

Peace Corps
Aside from the free round trip airline ticket, the two-year commitment to helping communities in developing nations, and the character development of living on eight dollars a day, the Peace Corps offers volunteers $6,000 cash at the end of service. Of course, this money could be used for a security deposit or a car back in America. I used it to bike in China, swim in Thailand, and get cheap spa treatments in Indonesia. Applying for the Peace Corps can be competitive and take anywhere from three months to a year.

Freelance
I’m a freelance travel writer. I’ve been paid everything for my work from exposure to a few thousand dollars. Better, I was the writer-in-residence for Belize as part of a social marketing campaign with the Belize Tourism Board. That means I was paid (not a whole lot, $30 a day) to travel around Belize for three months, while scuba diving and blogging. I’ve also gone to Micronesia, San Francisco, Miami, and Mexico on press trips. MediaBistro offers online writing courses, including several focused on travel writing. Or, WordPress has free blogging software.

Glammy
I don’t like to refer to myself as a babysitter, because that’s a job for teenagers. Bethenny Frankel calls her fill-in nanny a glammy, or glamorous nanny. So I’m comfortable referring to myself as that, too. I’ve gone to France, Newport, and Virginia with a lovely family whose full-time nanny isn’t always willing or able to travel. Being a glammy also means I’ve been stuck with a screaming baby in the back of coach for several hours and cleaned up his vomit at a gas station. Still, I never could have afforded a trip to the South of France during high season otherwise. Nanny agencies in urban centers are usually looking for babysitters (glammys) as support for clients who already have full-time nannies.

Frequent Flyer Miles
I was way too late to the frequent flyer miles game. It’s heartbreaking to think about all those flights I took across the ocean without accumulating anything. I’ve since educated myself and got a Delta credit card. Last week, I flew to Denver for five dollars and 25,000 miles. Sign up for the free miles program with every major airline carrier. Remember that the individual whose butt is in the seat always gets the miles, regardless of who paid for the flight.

Vouchers
Even more precious than frequent flyer miles are airline vouchers. Travel enough and the airline will eventually screw up. You’ll get bumped off an oversold flight or it will get cancelled and the airline will give you a voucher (usually worth $250) towards a future flight as an apology. Apologies are how I’m going to Costa Rica over Thanksgiving and to Wisconsin for Christmas for next to nothing. If a flight attendant asks for volunteers to be bumped onto the next flight in exchange for a voucher, for God’s sake, volunteer.

Friends
How was I able to live in Los Angeles for five months? My best friend had a guest bedroom. When my boyfriend swapped his apartment in Brooklyn for one in the Bay Area, I went with him. I just got back from a road trip through New Mexico because a friend works for the Marriott and got us incredibly cheap hotel rooms. I’m happy to return the favor (that is, once I settle down). For now, I’m looking into spending the summer volunteering for the National Park Service, housing and stipend included.

Megan L. Wood wrote this shortly after returning from the airport, and filed it before she left again. Photo: MikeBaird

I was pretty excited when I was accepted into my graduate program at Columbia University. I had only applied to one program, so it was going to be all or nothing. Columbia had overnighted the acceptance letter to me, so I pretty much knew I had gotten in before I opened the envelope (who would pay an overnight fee to reject someone?). But then I received a letter letting me know how much the university was going to give me:

I wanted more. I needed more. 

Tuition and fees were going to be about $44,000, and I also needed money for living expenses. One of the things you have to do when you’re applying to Columbia’s journalism program is take a writing test proctored by an alumnus of the graduate school. After I was accepted, I emailed my proctor asking her for tips, and she gave me a lot of great advice about choosing a place to live in New York, which classes were worth taking, and ended her email with the best tip of all: “By the way, don’t hesitate to go straight to [the dean of admissions and financial aid] and ask for more money. I badgered him enough to get a few more grants to cover expenses.”

I was young, and had little experience with negotiating money, so if she hadn’t tacked on that last bit of crucial advice at the end of the email, I would have never thought of simply asking for more money. It’s one of those things you need to learn as early in your life as possible: If you don’t ask for something, you don’t get it.

So, I asked for it. And when I was initially turned down, I asked for it again. My proctor ended up being right: If you plead your case long enough, and do it as politely as possible, there’s a good chance you’ll end up with more money. While I was in school, I received an additional $10,000.

I took this experience with me after I graduated and got a few job offers. Can’t get your employer to budge on the salary? Maybe you can get an extra vacation day. Lather, rinse, repeat: If you don’t ask for it, you don’t get it.