Why Is It So Hard To Ask?

Why Is It So Hard To Ask?

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Why Is It So Hard To Ask?

Twenty-four people are sitting in a high-level coaching session.

They are assigned a task:  that of breaking into groups of six and, within two hours, seeing how much money they can raise.  The rules of the game include not being able to leave the hotel where the session is being held and not using any of their own money.

Two hours passed.  What then unfolded was fascinating.

The first group got up and reported that they had selected a child from the Make-A-Wish Foundation and contacted the venues of everything that made up his wish.  They got the hotels and relevant companies to commit to freebies.  Then they went to their email, Facebook and other social media and got their friends and fans to commit to donating directly to the Make-A-Wish site.  All told, they raised over $4,000 in cash and kind.

The second group got up and announced that they could never even agree on a concept.  Instead, the exercise turned into a personal development session with all sorts of tears, breakthroughs and aha’s.  But no money.

The other two groups reported differing levels of success, landing somewhere between those two extremes.

Then the session leader revealed the purpose of the exercise:  “to test your ability to ask.”

To ask.  Sounds so simple.

But think about it.  How difficult is it for you to ask someone to pay you money they owe you?  Whether for services already rendered or money they borrowed.

How hard is it to ask for help when you need it?  Or how hard is it to ask someone for a favor?

Are we worried about being indebted to others?  Or being a burden?  Are we afraid we will be showing our weakness or vulnerability – our soft underbelly – if we don’t present an exterior of steel?

Think about how far our civilization has come.  For example, what ever happened to neighbor-helping-neighbor, as in the old days?  Do you remember hearing about the famous barn raisings, where an entire community came together and built a barn for a family?  Of course no chits were ever exchanged because they all knew that one day someone else would have a need, they would ask and the same community would meet the need with grace.

What are we so afraid of?

Are we afraid the person will say no to our request for help?  Well, that could happen.  But is it the end of the world?  There may be a perfectly logical reason why they’d have to say no in that specific instance that is no reflection whatsoever on our worth, ability or intelligence.

Are we afraid the person will think we’re only after their money if we ask them to look at our business venture or opportunity?  Well, that too could happen.  However, to not ask could mean we prevent them from accessing or getting involved with something that could bring them tremendous value … all because we were afraid.

What’s even  more important is that by not asking, we may be denying someone else the possibility of feeling really good about themselves.  After all, think about how good we usually feel when we can do something to help others.

Like the old barn raisings, we’re not meant to go through life doing everything alone.  But I admit that I have trouble asking for help and don’t  know how I would have handled the exercise.

So here’s what I intend to do next time I hesitate asking someone for something:  I will acknowledge that I am creating my own fear.  I’ll figure out how I’m scaring myself.  I’ll recognize that I’m adding layers of unnecessary negative ‘what ifs’ to what may be a perfectly positive interaction.  I won’t give in to the fear, but will be willing to feel it … and then take the action anyway.

What about you?  What would you have done had you been in one of the four groups?  Would you be willing to ask?

Let me know in the comments section below if you’ve ever even thought about this topic.  I know I hadn’t.


Bio: Sharon O’Day lost everything at age 53: her home, her business, everything. But how could that be? She’s an expert in global finance and marketing with an MBA from the Wharton School. She has worked with governments, corporations, and individuals … yes, she was the secret “weapon,” if you will, behind many individuals in high places. Yet she did! Since then, with her finances completely turned around, Sharon has gone on to interview countless women. She’s done extensive research to understand how that could have happened, especially with her strong knowledge of numbers and finance.

The surprising answers will be shared in her upcoming book “Money After Menopause.” Today her mission is to show as many women as possible how to become financially free for the long term, through her Over Fifty and Financially Free coaching programs. She has developed a step-by-step plan to get past all the obstacles that keep women broke and scared … and from reaching the financial peace of mind they so deserve … if they’re willing to do what it takes!

  • I must confess I too have a problem with asking for help. But after reading this Sharon it is on the top of my list if things to explore in my on-going quest of personal growth! I honestly don’t know what I would have done with that exercise…what the successful team did was brilliant! Thanks for a great article!

    • SharonODay

      It doesn’t surprise me, Denny, that you too might have struggled on the exercise.  It’s one more thing we share!  😉

  • Very thought provoking post Sharon, I personally don’t have too much of a problem to ask for others, however I must confess it is not the same to ask for myself… well I am challenging myself often and I have a strong sense of independence, so it is not that easy… Thank you for such an amazing article.:)

    • SharonODay

      Somehow we place independence above interdependence … where we all have our space but are there to support and assist one another on our individual paths …

  • Shahina Lakhani

    Love it! Feel the fear and take the action anyway! As a middle (and forgotten child) I always thought that no one cared to help. So I never asked for help. Years have passed since then. I am where I am today because a lot of people have helped me through my journey and because I have learned to ask freely, I am also inclined to give more freely. Thanks Sharon for such a thought provoking post.

    • SharonODay

       Shahina, terrific that you’ve been down this path … both of asking AND giving.  I find the giving very easy, the asking much harder.  But I’m working on it!

  • Janinedavid

    I was suppose to read your post today Sharon, it is wonderful when I’m toying with an idea that I should open my emails & there awaits an answer for me . What I have to do is get out there and ask appropriate people & business if they are in need of Alternative Healings or wanting to learn them as my studies are nearly over. Advertising myself is the key.
    I’m hoping I have made sense to you with that . The key is to “ask”
    Much Gratitude to you .

    • SharonODay

       Janine, what it comes down to is “asking” the right people for the sake of improving THEIR lives, not because you need or want to provide the service.  (In the case of the successful group in my post, they were thinking of the Make-A-Wish boy, not of themselves.)  Besides, if done this way, a “no” is never a rejection of ourselves, but rather a depriving of themselves of receiving the benefit … 😉 

  • Hi Sharon, it’s so good to be ‘back’ and I must say that your article was so well timed. Asking is a muscle that I need to develop more of. As you share in your article there is this context around asking that has to do with not being looked upon as ‘weak’ or ‘needy’. But genuine asking creates community and connection. That was evident in the group at that hotel that went on to raise $4000 for a child. Thank you for continuing to share your wisdom and insights with the world in such a genuine and compassionate way. Best wishes!!

    • SharonODay

       And it’s so good to HAVE you back, Eno!  I think many of us are guilty of not wanting to look vulnerable.  And my concern is that, as we become more separated through technology, we’ll have less and less feeling of community … and even less willingness to ask …

  • Sharon, maybe I am of the rare breed but not shy ever to ask for money except one time recently when I learned this lesson.  I had a roommate split the event fee with me.  She sent payments through Paypal. Guess who paid the fees?  ME!  Guess who didn’t receive anything from this person? ME!  So guess what ME has learned if there is a split?  Add in the additional ME charges. So I fell through the cracks this time but one time is enough for ME.  Great post.

    • SharonODay

       Carol, I hope you won’t stop being as open as you are about “asking” because of that one incident.  It was less about being willing to ask than it was dealing with someone who was simply out of integrity!  Now you know who that person “is” … 😉

  • Pat

    Enjoyed your post.  You certainly hit on a topic that can bring a lot of fear. I like your advice of how you will face it yourself.  Recognizing what is causing our own fear is a good thing, and the step to overcoming it.

    • SharonODay

      Pat, sometimes we can surprise ourselves with what triggers fear or with what’s behind the façade of “oh, I don’t need anyone’s help.”  As you know, I’m all for being brutally honest with ourselves.  What we choose to put out to the world is a matter of choice, but being honest with ourselves is key.   😉

  • Vicky Horner 3637

    This is so timely Sharon.  I was talking with a friend yesterday about how it “takes a village to raise a child”…. and also to care for an older loved one.  After a long conversation we decided that we could ALL use a village, whether the help comes from a friend, family member or even someone we pay.  None of us can do everything ourselves. 

    • SharonODay

      Vicky, more and more people are realizing this each day, especially as those already in their 50s and 60s recognize the chance might be behind them of still making a “big kill” in their salary or investments to fund their retirement.  Not 100% true, but it does raise concern in the present economic environment.  That being the case, being part of a tight-knit community offers all sorts of benefits!

  • Sharon, I had certainly thought of this but really had not come up with a solution for it.  My natural tendency is to not bother or burden people.  I feel much more comfortable helping others than getting help myself.  So I’d begun to realize the problem with a personal system like that.  Your article not only puts it into perspective, but provides a simple solution.  I will try that and let you know how it goes.  Thanks for this valuable insight!

    • SharonODay

      Hope it’s helpful, Robert.  Somewhere along the line we equate “not asking” with independence.  Or not bothering others.  How wrong we are … if we expect to help others when THEY ask!

  • Michele

    Much to think about. I absolutely HATE to ask for help. I am always happy to help in any way possible….

    • It’s such an easy pattern, Michele, but really doesn’t serve us well! I know I had to work at it myself, but what a relief to take off the Superwoman cape! 😉