3 Steps to Ask for Anything and Have Fun Doing It

ASK? the very thought is stressful. I always took it personally.  Every time I asked for anything.

You know what that does? It puts the stakes very high. When there is a greater risk we will avoid doing things. As a human, you are wired that way (Sure there are a few daredevils out there.). But, as kind and naturally loving humans, we don’t want to fail, we don’t want to hurt and we don’t want to appear stupid, foolish or arrogant.

When you ask for something and you have your whole self, reputation and inner sense of self-riding on the line, the asks don’t come. The emotions stop the brain and we FREEZE. We stay exactly where we are and then we call our self a “procrastinator”. Or, some make up a story to make sense of why we haven’t left our job, asked for the raise or negotiated a better contract with a client.

We don’t want to get demoralized… We don’t want to be turned down. It feels cruddy.

Feeling cruddy is not fun. And not getting what you need or want doesn’t feel good either, so you stay stuck because either choice doesn’t feel good.

We love to do things that are fun. We will put off doing anything that feels cruddy! Risk and feeling cruddy will keep us stuck.

We aren’t raised to ask for things we want, we are taught to share, be generous, make others feel better. But, ask for what we want?  That’s selfish, that’s being boastful and ego-driven (are those our words?)  

Instead, we think…. If I am good enough, work hard and do the “right” thing, good things will come my way….I know they will. They will notice what I need. It is logical, it is right, isn’t it? Won’t they treat me that way? I used to think that way, until reality showed me differently. Until I finally understood that we don’t get what we deserve, we get what we ask for.

The first few times I thought I asked for what I wanted was scary. It was new, it was — well…liberating. Scary, fun, liberating, scary, difficult. All those and more. I had to learn a new skill, just like anything new. It feels uncomfortable. It doesn’t fit. We have to wear it in, get used to it. But how?

The way to change our perspective and take on a new skill is through great questions. I asked myself questions, then I was able to make decisions. And I learned.

Do I want to be more successful?

Do I want to stand up for myself? Or be at the whim of someone else?

Do I want to be confident? Be a good role model?

Be more of an influence?

Do I want to be at the end of my days wishing I had?

I decided to learn how to ask for what I wanted and have fun. I asked better questions of myself.

Anytime we need to smash through barriers, change a habit that is holding us back or move forward in life we need a big WHY.  The why comes from asking great questions Yup,a really big WHY,  that BIG! The all caps, big (Kick Ass) reason why.

Here are the empowering questions to fuel your next big ask, (or even the small ones).


  1. What is this costing me to not ask?  Go ahead, write down what this is costing you. Think in terms of money, happiness, and long-term. What is your life going to look like at the end of the year if you don’t ask? What will you have lost in time, money, happiness in 3 years? Is the cost of not asking or not taking action for yourself? If you are making $80,000 per year and you know you can make $10,000 more in a promotion or a new job, that costs you $30,000 by not asking for 3 years. That is real money –GONE! Stack the deck in your favor. Power up– get clear on the cost in every way. This is fueling your motivation, get your WHY.
  2. What’s the worst thing that can happen? A NO? Yup. A no. Oh, you say, if I ask for the promotion and don’t get it, it is a NO and it is “them” knowing I didn’t get it. When I was an executive and leader, I thought well of people who asked, went for it, had ambition to do more and be more. Make your ask in the way that makes sense in your organization. Stand tall and know you are worth it. Oh, and, if it is time to move on….be real with yourself on that, also.  Take your emotion out of the ask as much as you can. De-personalize it. Be objective. I found this to be really important when I had client interactions and had to ask for things to make our contract or services valuable. Think about what you will do as the alternative. Having alternatives is necessary so you don’t have an ultimatum stand-off. Get creative and think about what is next, not as a threat, but for you and the position you want to make in your discussions. A great book on negotiating is the long-standing best seller, “Getting to YES” by Roger Fisher, William L. Ury and, Bruce Patton.
  3. Getting clear on the “WIFM”!!  Yes, you must know the other side’s motivation, the WIFM? “What’s in IT For ME?”  Yes, know what the other party wants out of the ask. When we ask for something and we know what the other party wants or what they will gain if they say yes we gain leverage and perspective. Let’s say you are asking for that raise or promotion. Stack the deck in the favor of your boss or company. DO NOT SAY they will get more work from you or more hours—that is not the point of a raise or promotion. Depth of expertise, organizational knowledge, and other reasonable aspects of your ongoing value. Think through these, list them, know them in your heart. You may not have to list them back when you ask. Yet, when you have a clear picture of what is in it for the other party and ask from that perspective it gives the ask a more meaningful tone to the other party. P.S- this works for any ask. You can put yourself in their shoes and see what they see.

All of these questions will fuel your next ask and keep your perspective open. Your life is worth getting what you want. Remember, we get what we ask for. So, ASK.

Visit my ALL New Webinar Bring Your Soul To Work. How I Landed My Dream Job. 

Here I review 5 SHIFTS you must make to finally put your inner self and outer work together. That’s what we all want,…to feel whole inside!