How to achieve anything by changing a single question.

Alt text: Kate stands in front of a chalkboard with an empty thought bubble drawn on it with an inquisitive look on her face

If you’ve ever had a big dream or desire, then you have had to wrestle with the question “How?”. 

For bright-eyed idealists like me, the “How” often comes from other people (the type I call “Dream Crushers”), and usually sounds like “Uh-huh, yeah right, HOW are you going to do that?” It’s not really a question. It’s a dream crush. 

But before we even share our precious dreams with other people, we usually ask ourselves “How?”, and immediately come up with 100 reasons why HOW is impossible. We dream crush ourselves. 

This often happens in a few different ways, based on the tone we use: 

  • The Pity Party “How”: 

    “How would poor little me EVER DO THAT? Can't you see how totally broke/tired/incapable I am?” This self-defeating “how” is more like a blanket we are hiding under, and when we using this tone it’s a good indicator that we could probably use a nap, under a real blanket. When we wake up we are likely to have a fresh perspective on our next best steps.

  • The Skeptical “How”: 

    “YOU? Start a business? You can’t even take that package to the post office that has been collecting dust on your desk for the past 5 months. And besides, haven’t you noticed we are on the brink of a recession? How are you going to even get clients?” This inner bully loves to batter us with “HOW” like it was a weapon. This voice is likely to reflect a montage of internalized voices from the people in our lives who have doubted us, even if it was coming from a place of genuine love or concern. While there can be an appropriate time and place to apply critical thinking, when we ask “how” from a skeptical place, we can easily spiral into overwhelm and self-doubt and shut down possibility.

  • The (highly irrational) rational “how”: 

    “It’s simply not possible. I’ve reviewed the data that we’ve never done this before, and the data points to the fact that we cannot. There is nothing in the data to suggest that we can. Dream application denied!” We are quick to jump to the assumption that, because we do not know how to do something, we can never do it. This may sound rational to the part of us that craves prediction, but it’s also absurd, given that literally everything we currently know how to do was once something we had to learn. You learned to speak an entire language when you were a baby—I’m pretty sure you can learn how to create a marketing plan.

If we want the question of “how?” to be effective and empowering, it requires discernment. 

The timing and tone of the “how?” will make or break your ability to actualize your dreams. If you start to feel the stirring of a vision and you immediately, desperately shout “HOW???!!!”, it will shrink back into the mysterious folds of your unconscious, and you will go around telling people that you “don’t know what you want.” 

As a coach, I have learned that more often than not people do know what they want, but every time it tries to emerge from them they “HOW??!!” it to death.  

When “How?” comes from fear, it shuts us down. When “How?” comes from genuine curiosity and a sense of possibility, combined with a clear desire and commitment, it can work wonders.

Allow me to offer an example of this from my own life: 

In 2011 I was fresh out of graduate school, newly married, and my biological clock was ticking, LOUDLY. My oldest son, August, was itching to be born. Problem was, I was a part-time yoga teacher with a very limited income and no health insurance, my husband and I were living in a 600-sq foot house that we rented, and when I started looking up the cost of childcare I realized that I made less per hour than I would have to pay in order to go to work. When I tried asking “How?” from this place, I was drawing a big ol’ blank. I remember saying to a friend, “Do you think it’s irresponsible to have a baby if we can’t afford it?” and he was like “Uh, YEAH.” Let the Dream Crushing commence. Yet, I couldn’t get over a deep, intuitive sense that it MUST be possible.


For one, billions of humans throughout the course of history who had fewer opportunities and resources than me had somehow managed to have babies, so why couldn’t I? I also believed that the choice to have a baby should be based on one’s capacity to love, not transactional notions of preschool tuition costs. I believed in the basic human right to choose whether or not to have a baby, in either direction. Because of all this, I wasn’t willing to accept that there was no HOW, so I started asking how with more genuine curiosity. 

“How could I get health insurance?” led to me being insured within the first month of my pregnancy. “How could we buy a house with no down payment?”, led me to discover an amazing local resource called the Portland Housing Center, where we found out about opportunities we never would have known about that led us to becoming home owners within the year. 

Becoming a mother came with a huge learning curve, but most of that training comes with experience, and no amount of planning and asking “how?” could have prepared me for it. I had to go into it with the willingness to stay in the curious HOW each day, instead of the defeated HOW. 

By doing this, I found out that I was capable of more than I ever could have predicted, opportunities opened up that I never could have known about, support came forward from other people that I could not have planned on, and I was capable of handling challenges that I would have avoided if I’d known they were coming my way, but once they arrived brought me valuable growth. 

The HOW was created in the doing of the thing. 

INTEGRATE:

Ready to stop crushing your own dreams? Take some time to get resourced and rested, and then sit down with the following journal prompt:

What am I holding back on because I don’t know HOW I will do it? What would I do if I did know HOW?

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