A Quote That Clicked

Have you ever had a quote, comment, or piece of advice that just immediately clicked?!

A few summers ago, two of my girlfriends and I were trying to figure out our late-night transportation plans (we were in a little town without Uber/Lyft) and while the location and details are completely irrelevant, one of my girlfriends said a phrase that has stuck with me for the last two or three years…

You don’t get what you don’t ask for.

My other girlfriend and I were going back and forth about asking our driver for a later pickup or not… We ‘felt bad’ and didn’t want to put him out or inconvenience him, you know? When our other girlfriend, who works in sales and is constantly negotiating and crushes it at work, interjected and said, “You don’t get what you don’t ask for.” If he says no, he says no, at least you tried. The context itself is silly, but I swear I’ve told myself (and others) the same thing at least once a week since then.

A few months ago in Santa Fe, for example… We were connecting in Texas between Albuquerque and Chicago and early in the morning, our later flight was already getting delayed. Dave has status on American and I asked him to call and see if there was any way we could switch onto the direct flight from Albuquerque to Chicago and he was like, “Jess, come on. There’s no way they’re going to switch us from a connecting flight to a direct.” Turns out, they did, and we got home hours earlier than we expected! (And that later flight ended up getting cancelled and we would have been stuck in Austin overnight.) We may or may not have tried a similar tactic with our upcoming flights to Italy to see if we could get an upgrade and were promptly denied, haha. 🤪

I was pinged to write a blog post about this little piece of wisdom from a DM I got over the weekend… I was talking about our garden center experience and someone said “Did you have to make an appointment to have it planted? I have been there before, but have never been offered the planting option.” It instantly reminded me of… You don’t get what you don’t ask for.

Especially as women, I think we’ve been programmed to just go with the flow, not inconvenience anyone else, and take what we can get. And for me, personally, I shrink away at the thought of most confrontation or putting myself in a position to get rejected.

I don’t know what’s gotten into me over the last few months, but I’ve found a lot more confidence to ask those uncomfortable questions. I was telling another girlfriend recent that I actually think Dave’s job has a lot to do with it… He also works in sales and I feel like I’ve learned a lot just from observing (and overhearing every. single. call. 😅) about persistence, finding detours around roadblocks, and not getting discouraged by rejection.

Dave likes to joke that I “negotiate against myself.” Sales have never been my strong suit. I worked at Nordstrom in handbags for a summer and quickly realized that I could talk about something I loved for hours, but I just didn’t have it in me to try to be “salesy.” It made my skin crawl, and honestly still kind of does. When I used to think of sales, I’d think of the stereotypical sleazy used car salesman. (No offense to any used car sales people!) I thought of someone just trying to shill a product to make a buck. But I’m trying to reframe my thoughts around this because, as I heard on a MasterClass talk, almost every single thing we do is technically a form of sales. Your personal brand, persuading effectively in a presentation at work, self-motivation, etc.

We all know that asking the uncomfortable questions can make a world of a difference… A higher salary, a signing bonus, a lower interest rate, etc. But it’s been helpful for me to just start asking similar questions on a smaller scale, so they feel less intimidating. “Are you able to do a bundled rate?” “Is there any sort of discount for paying upfront?” “Are you able to reverse this fee?” “Is there any way you’d be able to start the project sooner?”

I’ve had three part-time employees over the course of this blog and two of the three were from cold emails when I wasn’t even hiring. I know my last assistant told me she was so nervous to randomly email me, and I can relate because I get *so* nervous about emailing brands I’ve never worked with before. It’s so nerve-wracking putting yourself out there. But if you just ask, sometimes the answer is yes!

And as luck would have it… I was scrolling through some old screenshots on my phone last night and realized I screenshotted this post back in 2018, a couple of years before my friend said that comment that clicked. Maybe sometimes it just takes seeing and hearing and filing things away until that piece of advice finally clicks. Take it from Oprah…