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 find yourself owing somebody else a favor. But asking is truly the only way to access the opportunities and resources that can change our own lives and others’ for that better.

In this installment from the Living Experiment, we discuss the art of making requests according to your authentic desires. We explore how asking can make 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 that will 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 may be judged or resented, or otherwise make you look bad.
  • Women, in particular, may be societally discouraged from asking for what they need, for fear of “making a fuss” or becoming “a burden” on others.
  • Regularly compromising for less than we want tends to create patterns of resentment and frustration.
  • Not sure what you want? Look at where envy is turning up in your life, then look below the surface. Envy and jealousy in many cases are desire in disguise.

Build Connection

  • Skillful, thoughtful asking tends to build intimacy, not degrade it. Consider 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 satisfy.
  • Consider sharing with that person the procedure that brought you to this moment of asking, whether a time of reflection, a sudden insight, or perhaps 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 sign up 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 happier and healthier, the people around us benefit. The greater 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 items 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 getting a full range of responses as a way of building toward bigger asks.
  • Remember: Asking equals agency. Whenever you clearly express your desires, you steer your life in the direction of your own highest choices.


Pilar suggests:
Reflect on requests you've caused by others. Pick one that felt best to receive and one that was harder to deal with. Notice what made those asks have the way they did. Explore the relational dynamics at play. The next time you ask for something, keep those insights in your mind. Create a short list of requests you want to make, and start with one that feels doable now.

Dallas suggests:
Consider something you would like to ask for, and dare to inquire about 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.