Personal Development

If You Don’t Ask, The Answer Is Always No

By July 2, 2018July 16th, 2018No Comments
if you dont ask

“If you don’t ask, the answer is always no” is a phrase that has stuck with me ever since I graduated from Miami (OH) University back in 2002. It appeared in my email signature for years until I created Fact About Me of the Day and is a phrase that I can attribute many successes in my life to.

In sales and in life many people walk around scared. The fear of rejection, the fear of what others will think, the fear of the unknown. Fear is very powerful. It’s figuring out how to deal with and overcome fear and turn it into a positive that separates the men from the boys. And that’s where “if you don’t ask, the answer is always no” comes in.

One of the earliest jobs of my career was doing inbound sales at a Fifth Third Bank call center for home equity loans in Cincinnati. It was just as glamorous as it sounds. At the time I was a 23 year old still living like he was in college, caring more about kicking it with my friends outside of work than the crappy $10.50/hour paying job where my marketing degree was being severely under utilized (aka non-existent). While there I did the best I could with the gig, all things considered, but when you are young like that the grass is always greener on the other side.

At the time going out on Thursday nights was the norm. That made Friday’s less enjoyable than watching this year’s Knicks and Lakers play. If only there was a way to not work on Friday’s yet still keep the 40-hour/week schedule so that I could continue getting paid what I am now. And that’s when it came to me. I hatched a plan where I went to my boss and told him that I was most productive first thing in the morning and then again at the end of the day. When everyone else is slacking off that’s when I’m at my best (or so I said.) I’d come in an hour early (7 am) and leave 3o minutes later (5:30 pm) plus I’d shorten my lunch from one hour to 30 minutes. I’d do this Monday thru Thursday and that would still have me working a 40-hour week.

In what will go down as one of the most unbelievable backdoor covers of the world my boss said yes. I couldn’t believe it, the few guys I worked with couldn’t believe it, and my friends working at other companies couldn’t believe it. How in the hell did I make this three-day weekend thing happen?

“If you don’t ask, the answer is always no.”

What’s the worst that happens? He says no and I’m right back where I started. For the slight discomfort of pitching a ludicrous plan for having three-day weekends to my boss I got the upside of being able to sleep in until 11 am on Friday’s, lounge around, and have an absolutely phenomenal day doing whatever I want to.

Upon hearing about my new three-day weekends others in the office wanted to do the same but guess what. No one had the balls to ask. I kept hearing, “there’s no way they’d allow a second person to do that.”

“If you don’t ask, the answer is always no.”

If you’ve checked out the Our Work section of our site you’ll see many more examples of how I’ve used this phrase in action: the Ultimate NASCAR Bachelor Party, the Redhook Road Trip, and both Bacon, Sports & Beer Celebrations.  People often ask, “how did you make it happen?” It all started with an idea and the willingness to move towards discomfort knowing that the payout at the end would make it all worth it.

I challenge you to implement “if you don’t ask, the answer is always no” into your life. Who knows, you just might get what you ask for. I did.


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Rob Cressy

Rob Cressy

Sports loving free throw specialist and yinzer living in Chicago who is awesome most of the time, has run with the bulls in Spain, and is a graduate of Second City's Improv program.