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Most of us have been taught that asking for anything can cost us. Perhaps we’ll look weak, impolite, or needy. Maybe we’ll lose status or wind up owing somebody else a favor. But asking is often the only way to access the opportunities and resources that can change our own lives and others’ for the better.

In this installment of The Living Experiment, we talk about the art of making requests based on your authentic desires. We explore how asking can create stronger connections with others, even as it helps us build a more honest relationship with ourselves.

Finally, we suggest some strategies for making more successful requests, and experiments to help you explore the possibilities that asking might help open up in your own life.

Rise Above Resistance

  • It can be scary to ask for what you want, particularly if you feel your request might be judged or resented, or otherwise make you look bad.
  • Women, in particular, may be societally discouraged from asking for what they want, for fear of “making a fuss” or becoming “a burden” on others.
  • Regularly settling for less than we want tends to create patterns of resentment and frustration.
  • Not sure what you want? Look at where envy is showing up in your life, then look below the surface. Envy and jealousy are often desire in disguise.

Build Connection

  • Skillful, thoughtful asking tends to build intimacy, not degrade it. Think of your request as a means of deepening your relationship with the person considering it, not as an obligation or order for him or her to fulfill.
  • Consider sharing with that person the process that brought you to this moment of asking, whether a period of reflection, a sudden insight, or an emerging sense of what would work best for you and others. Help him or her understand the foundations of your desire, explaining the context of your request and articulate the deeper values that are driving it.

Embrace the Benefits

  • Look for the places your hopes and desires overlap with others’. See the bigger picture and ripple effect that could result from inviting others to participate in the fulfillment of your goals.
  • Regard your desire as inherently valuable and clarifying — no matter how your request is received. Desire, when clear and authentic, creates movement and momentum. It produces opportunities for all.
  • When any one of us gets healthier and happier, the people around us benefit. The more sustainably gratified and satisfied any group of people is, the better virtually everything in our society works.

Release Attachment

  • When you ask for something, set a clear intention for how you’d like things to go, but hold the outcome lightly, and be open to alternatives. Even a solid “no” or “never” can be a clarifying gift in its own right.
  • Recognize that somebody can deny your request without rejecting you as a person. Practice making small requests and receiving a full range of responses as a way of building toward bigger asks.
  • Remember: Asking equals agency. When you clearly express your desires, you steer your life in the direction of your own highest choices.


Pilar suggests:
Reflect on requests you’ve received from others. Pick one that felt good to receive and one that was harder to handle. Notice what made those asks feel the way they did. Explore the relational dynamics at play. The next time you ask for something, keep those insights in mind. Create a short list of requests you would like to make, and start with one that feels doable now.

Dallas suggests:
Consider one thing you would like to ask for, and dare to ask for it using the suggestions offered here and in the “Asking” episode. Keep your attention on how it feels to ask versus being attached to the outcome.

Thoughts to share?

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