Is it a Problem to Just Ask?

I want people to like my writing. I want them to love the work that I do. But I’m scared to ask.

I spend hours working on every article–writing and rewriting; adding and deleting; searching for the perfect words and flow. Believe it or not, that’s the fun part. The hard part is hitting “Publish.” With the click of one mouse button, my work is now on display for anyone to read.

Here it is, folks. This is what I’ve been working on, in all its glory. Feel free to criticize or tear it to shreds.

Anyone who has been to Mexico is familiar with the “foot soldiers.” I don’t know what they’re called–I just wanted to make a Ninja Turtles reference. They’re the people who walk down the beach or the street selling trinkets. It’s mostly useless junk: cheap jewelry, blankets, or sunglasses.

But there’s one thing these urban sales specialists have in common: they aren’t afraid to ask you to buy their trinkets.

You may be wearing sunglasses, but someone will ask if you want another pair. They’ll try to sell you a new blanket to replace the one you’re sitting on. They walk through the beach restaurants, and they linger in front of all the resorts. They’re relentless–and impressive.

For some reason, most Americans have trouble asking for things we want. It could be a raise, a sale, a promotion, some feedback, support, maybe a little help–it doesn’t matter. We’re stubborn or scared or intimidated or something. So instead, we go through life, continually disappointed when what we want or deserve isn’t handed to us.

Children have no problem asking for every toy or piece of candy they see in the store. They don’t need those things, but they want them. So they ask.

As kids grow up, they’re exposed to authority figures and gatekeepers everywhere. Outside of their parents, they deal with teachers, coaches, counselors, principals, bus drivers, cops, deans–the list is exhausting. And every one of those authority figures enforces rules and tells them, “no.” Over time, kids learn to conform to the rules and stop asking for each and every little thing they want.

We call this “maturity.”

Maturity is a good thing. Throughout the development process, we learn the importance of patience and respect for others. We learn that we don’t always get everything we want, and that life isn’t always fair. We rebel a little bit in college, trying to take some of our freedom back. Then they hand us a piece of paper that says we’re ready to be “real” adults.

At this point, the list of authority figures that we have to answer to is whittled down to law enforcement figures. We’re adults, with full authority to make our own decisions and do only things we want to do, so long as we don’t break the law.

Yet, we can’t seem to shake this feeling that we have to go through life under the thumb of someone else. We don’t take back all of the autonomy that was kept just out of reach as children. We don’t realize we’re actually allowed to say “no” ourselves. That we can ask for things from other adults because we’re all on the same plane now. And those adults get to make their own decisions and answer “yes” or “no.”

In reality, the worst thing that can usually happen if we ask for something is someone says, “no.” Oh, the horror!

In 2008, the company I was working for put a freeze on raises and promotions. The real estate and banking industries had crashed, and that didn’t bode well for construction companies. New projects had all but dried up, and the outlook for the near future was grim.

At that point, it had already been 2 years since my last raise. No cost of living increase, no merit increase–nothing. An indefinite freeze on raises was scary.

The worst (and best) part was that I was still busy. We had a client who kept giving us work throughout the recession because their industry wasn’t affected as badly. I finished a dozen or more projects for them between 2008 and 2011, and we were profitable on every one.

I kept asking for a raise every few months, and always got the same response: “Sorry. There’s nothing I can do about it. There’s a corporate mandate–no raises.” It didn’t matter that I kept bringing in profitable work–projects that helped carry the overhead for our entire office, I might add. There was a “corporate mandate,” so my boss could use that crutch as long as it was there.

But I kept asking, increasing the pressure each time. Did I actually have the leverage to change jobs and take that client with me? I don’t know–we never talked about it.

After another year or two of asking, my boss somehow managed to get an “exception.” He gave me a raise after 4 years of asking. I don’t know if I annoyed him enough to finally ask his boss, or if he asked every time and was denied. Either way, it finally happened.

I tell this story because of what I learned. I’m not a confrontational person. I avoid difficult conversations and situations at all costs. So asking my boss for a raise was hard for me.

The turning point was when I convinced myself of my true value. I had brought my company a lot of revenue, and I thought I deserved some recognition. Most importantly, I figured out the worst thing that could happen: my boss could say, “no.”

When I framed it that way, it became a lot easier for me to just ask. This mindset is crucial, but I still struggle with it.

Take writing, for instance–this is what I love to do. I’ve started 5 or 6 other blogs over the last few years. I bought the domains, perfected the designs, created logos, and set up email lists. I started writing articles for them–and then deleted the sites completely, without ever sharing them with anyone. Why?

Sharing your work with other people is basically “asking” for approval. It’s asking people to confirm that what you’re doing is good or right or helpful. It’s asking them for feedback, both good and bad. And I don’t just mean sharing it with your friends and family, either. Let’s face it–they’re biased.

It was hard for me to share my first articles on Facebook, even though my network is small. Why is that? What’s the worst that could happen? People could ignore it, maybe? Or they could actually read it and then tell me how bad it was?

Life would still go on. The sun would still rise tomorrow. I’d still have my family and my friends. Basically, life would remain exactly the same. And that isn’t horrible at all!

What if you’re in sales? You can only wine and dine clients so much, and you can’t keep giving them trial licenses. At some point, you have to ask them to buy your product. If not, they’ll just keep taking advantage of you.

Maybe you’ve exceeded all your goals at work and are due for a promotion. Is it going to hurt to ask? At worst, you’ll get some feedback on what more you need to do to earn the promotion. I think you can guess what the best outcome would be. And if the boss says, “no,” enough times, then take your services elsewhere.

The trinket peddlers in Mexico have zero shame asking you to buy their stuff. If you say no, they’ll just ask again when you walk by 30 minutes later. Maybe they love the job. Or it’s a survival mechanism, and they have to sell things to buy food for their families. Maybe they believe in their products so much they can’t help but ask you to share in their joy.

I don’t know what’s different in America. Maybe we just yearn for people to notice our work without us being pushy. Maybe we think everyone else is too busy or preoccupied to respond. I do know that we’re sometimes scared to ask for things from people–I certainly am. But what’s the worst that can happen?

If the worst thing that can happen doesn’t involve you lying face down in a gutter or dead, then just ask.

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9 thoughts on “Is it a Problem to Just Ask?

  1. You asking for a raise for 4 straight years reminds me of a study my wife found on the wage disparity between men and women. The study found that one of the major reasons for the disparity was that men would ask for raises more often than women.

    • Good thing your wife is the boss!

      I’ll have to Google that study. On top of just inherent gender differences, I’d bet women feel even more intimidated because of the fact that there are more men in positions of power. And so the cycle continues.

  2. I experience this constantly with my artwork – afraid to price my work and share what I “value” my work at. Comparing it to other artists – is there work “better” or are they more tenured? Do I deserve that price point? Is it accurate? Will people simply laugh at me and find something cheaper on etsy?

    I’ve been reading your posts and it insipires me in many ways. I currently still hold my 9-5 corporate job and it limits my ability creatively to spend the amount of time I’d like to on my side business (artwork).

    I commend you for being vulnerable and putting this out there and being honest (and vocal) about this subject. Creatives are often afraid of this or scared of the feedback, but I welcome it!

    • Double (or triple) your prices. Seriously.

      I just spent the last hour looking for some articles to send you, but I couldn’t find the ones I wanted. I’ll keep looking. But here’s the premise:

      People place a higher value on things they pay more money for.

      If someone gives you a pair of $100 sunglasses for free, you’ll probably toss them around and not care if they get scratched up. But if you pay $100 for those same sunglasses, you’ll take better care of them.

      The same goes for services and products, like paintings. If someone pays $80 for an 18″x18″ oyster painting, they aren’t going to value it as much as if they paid $300 for the same painting. It’s because of this little psychological tick we all have that makes us justify to ourselves every decision we make–including spending money.

      Once consumers make a cognitive decision to buy something, they immediately begin justifying that decision. The human brain cannot STAND to be wrong, so confirmation bias kicks in and it does everything it can to make sure nothing contradicts its decision. Instead of telling the movers, “Oh, that painting just cost $100. Just toss it in the box with all the other picture frames,” it’s, “Wait! I need to wrap that up and box it separately! That painting cost $400!”

      And the best side effect: You’ll get rid of all the customers who want to nickel and dime you and complain because one brush stroke doesn’t look right 🙂

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