Why do we agonize over things we want? I’m talking about those situations where there seems to be an opportunity, but we freeze before acting. We’ve all been in those situations; ones that require a simple ask. That new opportunity, that raise, that account, that job order.
It’s right there, but we stop short of taking action. Usually, we start over-thinking the ‘what-ifs’. What if they say no? What if they don’t like the idea? Fear takes over.
The simple answer is to “just ask.”
A Valuable Lesson
I learned a valuable lesson in high school. My senior year, the Homecoming Weekend was getting ready to happen. I needed a date for the big dance.
On a total whim, I decided to ask the prettiest, most popular girl on campus to be my date. We were in a couple of classes together so we knew each other only a little. I stress that because it was not like I was on her radar at all.
I picked my moment between classes and threw out the question. Would you like to go to Homecoming with me?
She said “Yes.” SHE SAID YES!!!!
I was more surprised than I should have been. But I had the prize! A Homecoming date with the prettiest girl in school. Well, word spread rapidly. The other guys couldn’t believe it.
The big day came and we had a nice time. It never turned into anything else, but I had achieved what I wanted to do.
Plus, I learned a very valuable lesson. You have to ask.
Current Story
I have a client who owns a multi-million dollar company. They’ve been in business for many years, but recent market shifts have required a total revamp of the business. Old product lines are obsolete and new technologies have taken front and center.
The team has done well making ‘pivots’ to support new products and services. The owner calls the business a “25-year-old start-up.”
At the core of the recent success and seismic shift in business has been the owner’s willingness to ‘just ask.’ If there’s a meeting with a new national distributor and some opportunity arises, just ask.
Or a meeting with new clients, just ask for the business. If they run into a problem with an order, just ask about the details.
‘Just ask’ has become their battle cry for newfound success.
And guess what. It’s working!
Roadblocks
Yet why is it so darn hard to just ask? I meet many clients who have opportunities, but they fail to make that one next step… asking.

From my view, there are several key reasons why asking the big questions runs into roadblocks.
First, you can over-think the situation. Smart, well-educated people do this a lot. Their brain goes into high gear when a situation comes up. What about this? What about that? The list gets longer than the original idea.
Pretty soon you talk yourself out of the opportunity before you ever pursue it.
Next is perfectionism. I see this a lot. The person with a perfectionistic personality will over-analyze the idea. “If it can’t be perfect, I won’t do it.”
So many opportunities are missed because of perfectionism. Remember “Perfect is the enemy of good.”
There are some great moments that get lost because you think your involvement won’t be perfect. So you miss out entirely.
Then there is procrastination. Procrastinators bridge between perfectionism and just plain avoidance. I’ve seen procrastination play out in many forms.
Generally, the person who procrastinates usually has some deeper drivers at work. Since I’m not a psychologist, I can’t go into those details, but I know how debilitating they can be. I’ve watched it with far too many clients.
On the other hand, if you avoid delaying the ask, you might just strike the perfect timing. In high school, my timing for asking for the Homecoming date had to be spot on.
Summary
These are the big three reasons people have trouble making the ask. If you suffer any or all of these, just try being bold for a short period of time. Stop over-thinking, quit being a perfectionist and don’t wait.
Just ASK! You might be pleasantly surprised at what it can do to your business, your relationship status, and your sense of well-being.
One last thought to share about asking for something.
I grew up being mentored by many people. I was an only child of a single Mom. She had wisdom beyond her years to go out and find willing individuals who would take me in and become my mentor.
They didn’t literally have me come live with them, but they made time to teach me things. Through the grace and strength of a long list of great men, I learned all the things a young boy should learn; how to hit a curveball, how to fish, how to do woodworking, repair things, play tennis, throw a spiral, build things, plus a few life lessons. (Like asking the prettiest girl to the dance.)
As I grew older, I still valued mentorship. So I asked for it. If I met someone who I learned to respect and admire, I’d ask for time to hear their views and learn how they got to where they were.
The point of this is, don’t be afraid to ask for mentorship. A lot of very skilled and talented people will be honored that you did ask. And they’ll be happy to come alongside to help.