Do You Ask For The Order?

[Jay is downing Coronas today before heading back from the beach… Please enjoy this article by Erin of in his absence. It’s an important one to keep in mind – esp for you hustlers!]

My mother had an adage she often used if my sister and I ever complained about wanting something we didn’t get. Anytime I’d moan about how (my incredibly privileged) life just wasn’t fair she’d ask, “did you ask for the order?”

The first time I heard the expression, my head snapped up and my pout turned into a look of confusion. What did ordering something have anything to do with the insufferable injustice I happened to be dealing with (probably not getting enough playing time on the soccer field or something equally as insignificant in my life today)? She explained that people weren’t mind readers and if you didn’t ask for what you want how were you supposed to just magically get it?

Asking for the order doesn’t mean you always get what you wanted, nor did it mean acting entitled to something you didn’t deserve. It simply was my mother’s* take on the famous quote, “you miss 100% of the shots you don’t take.”

Her expression became something of a personal mantra for me over the years.

The first time I put it into action had nothing to do with a career or money. As a senior in high school I was required to complete a rigorous thesis project for my International Baccalaureate Theatre class. I knew I wanted to do something no other students in our school had done before. So, I asked if I could take over the theater teacher’s position as director of the school’s fall play.

She not only said yes, but also gave me complete creative control and rarely even sat in on rehearsals. Let’s face it – she probably liked having a break from dealing with dramatic youths.

I got a taste of asking for what I wanted, and now it’s a regular habit (and sometimes not always appropriate).

On the night of my 23rd birthday, I staggered into a Dunkin Donuts around 12:30 at night after a few birthday beers. They had some sort of deal, like two doughnuts for a dollar, but in my inebriated state I started to negotiate for more doughnuts.

I pointed out that in a few hours all the remaining doughnuts would be getting tossed for fresh ones for the morning. What would be the harm in saving them from a sad end in the trash by letting me put them in my stomach?

The pimply teen at the register ended up tossing in six doughnuts for a buck and I felt victorious (until I bit into a doughnut that had been sitting out all day).

Freelancers have to “ask for the order”

I first made the jump into blogging with the lofty mission to help my fellow millennials learn about personal finance. I didn’t have goals of using my site to create revenue, and didn’t even think about leveraging my work for a career as a freelance writer.

As the months went on, I started to hear all about side hustles and picking up extra gigs outside of a 9-to-5. It dawned on me that I could take the skill set I’d developed from my blog and get paid to write. The only catch: figuring out how to find someone to pay me for my work. Thinking back to my Mom’s expression, I simply started to ask around. If someone tweeted at me that they liked my work, I asked if they were hiring.

My first big break happened just about a year ago.

AOL’s DailyFinance tweeted a millennial-focused article to me, probably looking to have me share it with my network. I took a few seconds to draft up a 125 characters response (their handle takes up 15) and asked if they were looking for contributors.

Not only were they in the process of onboarding contributors (I actually got the inaugural slot and still serve as a DailyFinance contributor), but they also asked if I could come in and lead a discussion with the AOL interns about practical budgeting.

All that from a simple tweet.

This success gave me the confidence I needed when a career-changing opportunity presented itself.

A couple of months ago I was approached to write a series for a reward travel site. After deciding to take the job, the owners of the site mentioned they were in the works of creating a finance-focused website with a consumer advocate angle. They asked if I could come in to test the site and give some feedback.

I went into their office, started playing around with the site, and immediately knew I wanted to work for them. The company mission was perfectly aligned with my hopes for helping the American public become financially literate, with the added bonus of increasing transparency in our financial system.

Hearing my mother’s voice echoing through my head, I asked if they had anyone to help develop the content on their blog and to handle their social media presence. When the answer was no, I asked if they were looking to hire someone.

The next step was to more-or-less create my job because the company was a startup and didn’t exactly have defined roles for a brand and content manger (a title I also made up for the job).  I went home and created a proposal, which explained the various aspects of what I thought I could do to help the company as it launched and worked to become established. The proposal also included my desired salary and benefits.

A few weeks later I started working for the company, making more money than my previous job and matching all the benefits.

In the last few months, I’ve quite literally changed the course of my professional life by asking for the order. At only 25, I hadn’t quite settled on exactly what I wanted from a career, but I knew I wanted to get into something more finance-focused than my previous job in public relations. I knew I wanted the opportunity to write and to help people. When the opportunity to fulfill those professional desires suddenly appeared before me, I decided to go after it.

After all, why not ask? The worst I could be told was no.

Erin is the founder of the blog Broke Millennial where she uses sarcasm and humor to explain basic financial concepts to her fellow millennials. Erin lives in New York City (as cheaply as humanly possible) and now works for the startup MagnifyMoney.

*In recent years I found out she actually ripped off this expression from my father’s college roommate!

[Editor’s Note: Remember when I told y’all I was thinking of doing some freelance writing myself? So I started asking what peoples’ budgets were before turning them down blindly? That resulted in $1,000 and $500 writing gigs. PER ARTICLE. So asking for what you want REALLY does work. Not always, but often. And Erin helped me to realize this even more after hearing about how many times she just goes after it. So def. keep this in mind while out there hustling!]

[Photo by the (incredible) Reggie Bibbs – Learn about his story here]

(Visited 7 times, 1 visits today)

Get blog posts automatically emailed to you!


  1. Nicola August 15, 2014 at 5:16 AM

    Great post! I think that the saying “if you don’t ask you don’t get” is the same – people don’t know you’re looking for work if you don’t ask/show the fact that you are. Thanks for the reminder :)

    1. Broke Millennial August 15, 2014 at 10:58 AM

      Thanks, Nicola. Hope it works well for you in the future!

  2. Kirsten August 15, 2014 at 5:46 AM

    Oh my gosh, this is so motivational to me. Exactly what I needed to read as I start trying to get freelancing work. I actually just sent in a guest post to another blog last night and confessed I’d been wanting to do that for months, but I’d been too chicken. You are so right though – I can’t get what I want without going after it!

    1. Broke Millennial August 15, 2014 at 10:59 AM

      Aww, thanks Kirsten. Glad this came at a perfect moment for you! I bet your guest post kills it and can lead to other opportunities.

      1. J. Money August 19, 2014 at 1:56 PM

        Smart Kirsten! Imagine if you got in the habit of asking people once a week?? Odds totally in your favor and you get better with each ask :)

  3. Stefanie @ The Broke and Beautiful Life August 15, 2014 at 6:33 AM

    I’m always inspired the180 you’ve made simply by doing good work and being clear about what you want. Sometimes it’s the simplest things.

    1. Broke Millennial August 15, 2014 at 11:01 AM

      You’re a pretty similar story yourself and leveraged your work into a lucrative situation! *high-five* for going after what we want.

  4. Aimee August 15, 2014 at 6:59 AM

    LOVE THIS!! This is something I learned from my experience as a Girl Scout, both as a girl and a leader. I teach it to my girls and my sister. At work my coworkers ask me how I “get away” with things or how I “convinced” the guys (the partners) to let me do something. My response every time is “I just asked.” My coworkers say “I could never!”

    1. Broke Millennial August 15, 2014 at 11:03 AM

      I was a girl scout too! Maybe that was the secondary push in life to go after what I want. :)

      I love to hear this tactic working for others, especially women because we so often are viewed as less aggressive in the workplace. Props to you!

      1. J. Money August 19, 2014 at 1:57 PM

        The only thing I remember from Boy Scouts is to leave an area cleaner than you found it, haha… which I literally think of at least once a day :) And probably act on every other day – hah.

  5. Brandy @ Busted Budget August 15, 2014 at 8:17 AM

    This is awesome. As a new blogger and someone who hopes to break into freelance writing, thank you for the tips and motivation to get started!

    1. Broke Millennial August 15, 2014 at 11:16 AM

      It takes a bit of time, but stay persistent and it can lead to really big things! Glad to have you in the community. :)

  6. John @ Frugal Rules August 15, 2014 at 8:27 AM

    VERY cool Erin! It’s awesome to look back and see how things turned around from a simple tweet. But, it really comes down to that mindset of being forthright to ask for what you want. It doesn’t always work out like you want, heck it often doesn’t, but it’s so worth it in the long run. We see this ourselves with our business – it’s funny how you take on this mindset when what gets put on the table depends directly on how much you hustle. :)

    1. Broke Millennial August 15, 2014 at 11:19 AM

      You’re right, it doesn’t always work out. But you gotta ask, right? It’s amazing how many people say, “I wish I had {insert here}” when they may have gotten what they wanted if they just asked for it. And if you’re told no, at least you have the closure. That’s how I prefer to live.

  7. Kate@GoodnightDebt August 15, 2014 at 9:02 AM

    Love this! Thanks Erin! I can’t expect those around me to be mind readers! Just gotta ask!

    1. Broke Millennial August 15, 2014 at 11:21 AM

      Wouldn’t it be awful if everyone around us were indeed mind readers? :P I know I’d be in trouble, A LOT!

  8. Brian @ Debt Discipline August 15, 2014 at 9:05 AM

    Great stuff Erin. It never hurts to ask, people just tend to be afraid to take the leap. Your story proves it’s worth it.

    1. Broke Millennial August 15, 2014 at 11:24 AM

      Thanks, Brian. More need to realize that “no” isn’t an awful rejection. It happens to us all, so just take the leap sometimes! You never know how it will pan out.

  9. Kassandra August 15, 2014 at 9:31 AM

    It’s definitely about having the right mindset to go after things you want even if the worst that you can be told is no. Many people are too afraid to try and be rejected.

    1. Broke Millennial August 15, 2014 at 11:27 AM

      I know I’m afraid of rejection in certain realms, but being told no about a job or guest post or freelance opportunity via the Internet is definitely not one of them!

      1. J. Money August 19, 2014 at 1:58 PM

        Over time you expect to be rejected too which is MUCH easier to deal with than being scared of it :) It’s like getting hate mail from your blog – all a part of the game. Especially as you get more popular.

  10. Will August 15, 2014 at 9:43 AM

    Oooh, I love this article. The good jobs are never advertised so you’ve gotta do the sleuthing.

    1. Broke Millennial August 15, 2014 at 11:29 AM

      Thanks, Will! I never guessed I’d fall into such a great job through an interesting set of circumstances, but thank goodness I did.

  11. Emily @ evolvingPF August 15, 2014 at 10:01 AM

    What an inspiring set of stories! I do this a bit but I should do it everywhere! It reminds me of the “good guy discount” but more impactful because you’re applying it to your career instead of just purchases.

    1. Broke Millennial August 15, 2014 at 11:29 AM

      At least do it at Dunkin Donuts super late at night! Who doesn’t want free donuts?! :P

      1. Darrell August 15, 2014 at 12:29 PM

        The Dunkin Donuts part was my favorite. An article this week talked about asking for discounts on coffee…and I’ve heard the good guy discount. Rather than making it a test of thick skin, you can just ask, “Are there any coupons that you have in circulation?” I don’t imagine it’d be too hard to convince them to apply them. I do this when I get oil changes. Before I hand over the keys I say, “I don’t have it with me, but I saw an ad in the Pennysaver for $21.99. Can you honor that price and change the oil now…or do you want me to come back later?” 60% of the time, it works every time.

        1. Broke Millennial August 15, 2014 at 1:29 PM

          Money saving tips and an Anchorman quote. Swooning!

          1. J. Money August 19, 2014 at 1:59 PM

            Speaking of Dunkin Donuts – went there a few hours ago and they gave me back a dime instead of $0.7 I was owed??? Great for me, but why do they hate money so much?? :)

  12. Shannon @ Financially Blonde August 15, 2014 at 12:46 PM

    I love this! I always quote Wayne Gretzky, “You miss 100% of the shots you never take.” If you don’t ask, then how can you expect to receive anything. I tell clients to do this all the time with getting better deals, lower rates on cable, and fees refunded from banks. They always look at me like I am crazy, but you never know unless you ask. I am SO proud of how far you have come in a year and I can’t wait to continue to follow your successes!

    1. Broke Millennial August 15, 2014 at 1:31 PM


      And I sincerely appreciate you being someone for me to turn to and ask tons of questions and serve as a mentor.

    2. J. Money August 19, 2014 at 2:00 PM

      Yes Shannon!!! Calling up and asking is literally the easiest way to save/make money – it takes minutes, if not seconds?!

  13. Mrs. Frugalwoods August 15, 2014 at 1:43 PM

    Very inspiring, Erin! You’re so right that if you don’t advocate and hustle for yourself, no one else will. Thanks for sharing this–I’m definitely feeling motivated!

    1. Broke Millennial August 15, 2014 at 2:27 PM

      Thank you! Everyone should be their #1 advocate (parents are probably a close second).

  14. Ben @ The Wealth Gospel August 15, 2014 at 2:02 PM

    Love it! I just wrote about asking when it comes to my first year freelancing. It does wonders! Oh, and you’re awesome. Boom!

    1. Broke Millennial August 15, 2014 at 2:52 PM

      Haha, well thanks, Ben. Your $13k+ story is insanely impressive (including the German blog spin off!)

  15. Grayson @ Debt Roundup August 15, 2014 at 2:19 PM

    You rock Erin and you are correct. You can’t get anything you don’t ask for. No one is a mind reader and giving hints is not good enough. You are awesome Erin!

    1. Broke Millennial August 15, 2014 at 2:53 PM

      Grayson, you’re making me blush! Thanks for the kind words.

  16. Syed August 15, 2014 at 4:18 PM

    Love this. You’re exactly right people aren’t mind readers so it’s a good idea to just state what you want. The worst that could happen? They say no, you learn from it and move on. Thanks for the great reminder.

    1. Broke Millennial August 17, 2014 at 1:29 PM

      Thanks, Syed. Sometimes hearing no isn’t fun, but it’s better than regretting never even going for it in the first place!

  17. Jennifer August 15, 2014 at 4:49 PM

    So true! When I was graduating high school and planning to move to New Orleans for grad school I had no job, no housing, and knew nearly no one. While reading a Time Magazine article in my university’s student development office one day in my last semester, I learned about an organization that was helping rebuild New Orleans after the hurricane. Fascinated, I googled the group and wrote an email asking if I could work in exchange for free housing for them. They said yes and in the end said they would also pay too and let me set my own salary. It was crazy but it worked. In the same way, as I finished grad school I asked a visiting professor if he could help set me up with an internship with World Vision where he worked full time. He said yes and a few months later I was living in South Africa with a paid internship, a home, a car, and a maid three times a week. It was amazing and crazy. Just ask.

    1. Broke Millennial August 17, 2014 at 1:31 PM

      Wow, great stories! Thanks for sharing.

      1. J. Money August 19, 2014 at 2:01 PM

        HOLY $hit!!! That is fascinating! So awesome Jennifer!

  18. Melanie @ My Alternate Life August 15, 2014 at 7:31 PM

    This is amazing! I am starting to become more assertive. Now I have to as a freelancer! This is a truly inspiring tale and I’m so proud of you! Thanks for giving this great advice and sharing your story. :)

    1. Broke Millennial August 17, 2014 at 1:39 PM

      Thanks, Melanie. The freelance life certainly demands being assertive, especially if you have a difficult client!

  19. Steve August 15, 2014 at 8:39 PM

    I’m slowly coming around to the fact that you can approach the world in 2 ways:

    1. “Oh poor me!”

    2. “Oh look at all the opportunities!”

    Thanks for showing that opportunities are everywhere – one just needs to go searching for them!

    1. Broke Millennial August 17, 2014 at 1:39 PM

      Living by way #1 would just be bad for your health! #2 is what it’s all about.

      1. J. Money August 19, 2014 at 2:02 PM

        Also, it helps (immensely) to KNOW what you want too. Can’t ask when you don’t know.

  20. Rebecca @ Stapler Confessions August 17, 2014 at 10:41 AM

    You have a great point, and remind me of my athletic experience with “Asking for the order.” When I was in elementary school, my soccer coach instilled in us the belief, “If you ask to play in a certain position, you will play ‘left OUT.'” Doh! And it wasn’t until high school, when I played on a men’s lacrosse team and heard the guys constantly say to the coach, “Put me in, coach! Put me in!” how ingrained in me it was to NOT ask for the order. I could have used your mother’s advice at some point :/

    At the time, I thought it was a difference in gender expectations. But now I wonder if I ever had another coach tell us not to tell them to put us in the game or what position we wanted to play. It just so happened that one of my first coaches set the stage for the rest.

    1. Broke Millennial August 17, 2014 at 1:43 PM

      I think it can most certainly be a gender difference though. I feel a lot of women aren’t comfortable advocating for themselves, but then can on behalf of other people (there have been many studies on this). Perhaps I’m simply fortunate to have been raised in an environment where I was taught to ask for the order. I still find it difficult it at times, but overall it has served me well. Hope that first coach’s mantra can be erased from your memory!

  21. Even Steven August 17, 2014 at 11:46 AM

    I think it is great that most importantly you know what you want and ask for it, it has gotten you places you want to be for sure. I think I am figuring out what I want to be and I want to have a great personal finance site that goes through the story of paying back my debt, reaching financial independence, and retiring early. It’s going to be one long journey that’s for sure.

    1. Broke Millennial August 17, 2014 at 1:46 PM

      It will be a valuable resource to others and great for you to be able to go back through the journey yourself!

  22. debt debs August 17, 2014 at 10:12 PM

    Yup, the best advocate for yourself is yourself. Everyone else is busy with their own stuff (advocating for themselves ha ha and helping others who ask for the order), so you can’t assume they will have your needs front and center all the time.

    1. J. Money August 19, 2014 at 2:03 PM

      #TRUTH x10

  23. Laurie @thefrugalfarmer September 27, 2014 at 9:01 PM

    Smart lesson here, Erin. I am finally, at 47, learning the value in asking for the order and it’s working!!! I can’t believe I wasted all of those years being afraid of getting a “no”!