How To Be Bold: The Art of The Bold Ask

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The Art of the Bold Ask: The Bigger, the More Audacious, the Better

Asking for what you want is never easy. This coach blows that timid concept up

By Christina Langdon

Women often attempt to handle everything on their own, balancing careers, family, and the daily demands with a never-ending to-do list… and NOT ask for help.

That was me for 30 years working in media. My life may have looked perfect on paper, but I felt perfectly miserable on the inside. I was showing up each day by default. I would look at my calendar to direct my days instead of creating the week I wanted. Instead of getting clear on what success looked and felt like for me, I was a robot answering to others, taking care of the kids, and living the expectations others had for me and that I had for myself. I believed things happened to me, not because of me.

When I finally realized that the biggest influencer over me was, well, me, it was a game changer. Learning to take control starts with one simple yet bold request. 

Boldly asking for what YOU want.

How To Be Bold: Ask For What You Want
My perfectly miserable state of mind changed when I set out on a new career path, coaching high achievers and visionary leaders to help them redefine success and happiness in their second (and better, in my opinion) half of life. I attribute my newfound success to letting go of the fear of asking for what I want. 

And today, I make it a practice to make one bold request each week. 

I’m thoughtful about the practice of bold asks. A bold ask must be out of my comfort zone; it cannot be easy. In fact, it must be audacious and meaningful (the more outrageous, the better), and it must have a target or intentional outcome. 

Expert entrepreneurial coach Dan Sullivan, in his book, Who Not How, shares that success comes from the who (remember, things happen because of you), not the how (things happening to you). In other words, asking, who can help me? This is the bedrock of my bold ask protocol.

I committed to the practice by making a long list, which I keep adding to in a Google document. If I complete one bold ask, I add another. Each week, I open the list and pick one ask that gives me the most energy. The list has become a playground for adventure and growth for me. 

How To Be Bold: The Practice of Bold Asks
My appearance on the Reinvent Yourself podcast came from a bold ask. I asked a friend if she would share Lesley’s email with me and wrote to her to share my story and ask if we could meet. That meeting not only led to the podcast but to writing this article, and teaching a Covey class.

My most recent ask was a big one: I asked an old colleague to offer my Success Unleashed class inside her organization. I have not heard back, but I’m hopeful. On the list next is asking for a rental fee to be waived for an event I’m hosting.

Most times, the bold asks are by email, but often I look at my week ahead of my meetings or events and consider where (and to whom) I can make a bold ask. 

Looking back on this list throughout the year gives me a sense of accomplishment, even awe. I think, ‘Who am I to have made such requests?!’ It becomes the history of my year and a place I can visit when I’m feeling off-course or down and need a swift reminder that things are working. 

What I’ve learned by putting this protocol into action is that, more often than not, I receive a positive response. A YES to my bold ask. Those dream ideas, wants, and wishful thinking get accepted and put into action. I can look back at my highlights from the last year, and a lot of it was due to — or because of — a bold ask. 

Knowing this, the asks have gotten easier. When I started this practice, I would go into overthinking and ruminate about what “they” would think about me or how “they” would judge me for my bold (and sometimes brazen) ask.

Today, I no longer make a negative response mean anything about me or the ask. This huge shift has made me focus on the next ask instead of brooding over a No. I’m no longer attached to the outcome. If a bold ask comes back with a big “No,” I tell myself it’s not a “No,” but a “Not yet” or “Not now,” and I move on to the next one. 

The feedback has been so positive, with people responding saying how happy they are that I asked. They were so happy to hear from me. That “the ask” was a wonderful idea. That they love helping others. 

Life is not a one-way street. My bold ask practice comes with a return receipt. I make it a practice to return asks of me to actively and happily help others. As for me, I’m focused on the possibilities of where a bold ask can take me. Because I know from experience that you get what you ask for.

Christina Langdon is a high-performance coach who helps high-achieving women live a whole life by unlocking new awareness, power, and freedom from whatever may be holding them back, mentally and physically. You can connect with her on Instagram @christinalangdonbosslady or sign up for her newsletter, The Sunday Sunshine.

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