Have you ever made an impulsive decision and later wished you’d gathered more information first? I know I have.

Too often, we changemakers make quick decisions without pausing to consider the information we need first.

Often, we invest lots of energy in pursuing a certain path or coming up with new policies or programs before we pause and listen for what is truly needed.

But, as I’m sure you know, neglecting the critical information-and-feedback-gathering phase can have many negative, unintended consequences.

To make wise decisions that increase our potential for impact and joy, we must learn to ask questions and listen carefully.

We must get the outside view.

What is the outside view?

In Thinking Fast and Slow, Nobel Prize laureate Daniel Kahneman defines the outside view as statistical data from similar cases.[1]

For example, if you’re considering starting a business, knowing that 20% of new businesses close in the first year, 50% close in five years, and 70% close in the first ten years can help you set realistic expectations and not feel like a failure if you struggle.[2]

I use a slightly expanded definition of the outside view.

Whereas the inside view is what we feel, need, want, and think, the outside view is information from the world outside of ourselves, including what others need and want and what has worked and not worked for people pursuing similar paths and facing similar challenges.

For example, in 2018, while preparing for my MBA capstone, I decided to analyze the words my coaching clients write most frequently in their intake forms. I got out my spreadsheet and tallied the words I read repeatedly.

That’s how I realized that the word my clients use most often on their intake forms was clarity. Getting the outside view in this way inspired me to study what helps people get clear about what’s next in their lives and, ultimately, discover the body of work that I call radical discernment.

In my love letter this week, I’ll share three sets of guiding questions that I’ve found particularly helpful for getting the outside view.

Outside View Question-Set #1: What Information You Need

Often, my clients come to me facing a dilemma, spinning in their minds about what to do next, and while I do have all sorts of practices in my toolkit, I prefer to choose the easiest route first.

And so, often, I invite my clients to respond to these seemingly simple questions:

What do you know about your challenge?

What don’t you know about your challenge?

What questions do you need to answer?

What information do you need?

And who might you ask to help you gather this information / answer these questions?

You might be surprised how much clarity these questions can elicit. I still often am!

If you’re facing a challenging situation and are confused about your next steps, I invite you to grab your journal and open it up to two blank pages.

At the top of the left page, write: What do I know about this situation? What don’t I know about this situation? Brain dump everything you do and don’t know.

When you’re complete, ask yourself: What questions do I have? What information do I need to gather? Who might I ask? And, what’s my next step to gathering the information I need?

Then, take your next step to gather information.

PS: If you hear yourself asking questions that start with Why can’t I…?, I invite you to ask something slightly different. “Why can’t I” questions stem from an assumption that we can’t do something. Instead, try asking a question starting with “How might I?,” which assumes curiosity and that with enough desire, time, and support, you can learn what you want.

Outside View Question-Set #2: What Has Worked For Others

Dominant culture trains most of us to try to solve our questions by ourselves and to believe that we’re only successful if we go it alone. But the truth is, we’re much more likely to meet our needs, achieve our visions, and build strong movements when we turn toward other people for support and guidance.

With that in mind, from now on, when you’re facing a challenge or a question, I challenge you to get curious about who else may have successfully answered the questions you’re asking or have overcome similar challenges.

For example, if you’re considering starting a business, reach out to people who’ve started similar businesses or people who serve a similar clientele. If you’re considering running for public office, reach out to people who’ve run for office or trusted people who know your community well. If you’re considering applying for a job at a new organization, contact people who work there. If you’re contemplating a significant work-life change, you might even think of people whose work lives you admire, even if they are only tangentially related to what you want to do.

Start a running list of people who might have successfully undertaken an endeavor similar to the one you’re considering, have insights about the challenge you’re facing, or who might introduce you to people they know, and add names as they come to mind.

Then, reach out and ask people to have a conversation. Let them know the path you’re considering or the challenge you’re facing, and ask if they have any words of wisdom for you.

Outside View Question-Set #3: What Does the System/Do Others Need

When people burn out from over-giving, over-achieving, and over-caretaking, we commonly want to shift to the opposite side of the spectrum.

The Giver says: I’m putting myself first! The Achiever says: I give up! The Caretaker says: Screw everyone else!

Granted, there is wisdom in this impulse to let go. Sometimes, a part of ourselves that’s been overactive must sleep for a while to nurture parts that we’ve rejected or neglected. For example, the part of ourselves that gives to others may need to stop giving so much for a while so that the part of ourselves that is learning to receive can grow stronger.

However, the dominant culture’s insistence that we see the world through an either-or, all-or-nothing lens can keep us oscillating between extremes, hold us back from perceiving possibilities, and prevent us from becoming the full expression of ourselves.

Ultimately, becoming liberated and whole is about learning to dance in the both-and:

  • Giving and receiving
  • Caring for ourselves and caring for the collective
  • Resting and rising
  • Taking space and making space.

Not necessarily at the same time, but in ways that meet our needs and the situation’s needs at any given moment.

Besides, if the collectives we’re a part of—our families, friend groups, workplaces, communities, humanity, the planet—are not well, we cannot be fully well, either. So only focusing on ourselves is not an effective strategy for lasting wellbeing. But you know that.

So, in addition to tuning in and discerning what we need personally, we must also look outside ourselves and listen for what others and the system needs.

The English word system comes from the Greek word systema, meaning a whole composed of parts. When I use the word system in this context, I’m referring to the sum of the interrelated elements or beings that your actions touch—you, other individuals, the group/community/organization/relationship you’re a part of, the place/land, and so forth. I often use the words situation, collective, and system synonymously.

For example, imagine you’re in a conflict with a colleague at work. In this case, the system might include you, your colleague, other important people at your work, your values, the greater purpose of your work, the people you serve, and perhaps other elements.

Asking what the system needs can initially feel disorienting because the dominant culture trains us to focus on the individual rather than the collective. So, I encourage you not to try to find a clear-cut, perfect answer to these questions. Instead, I challenge you to allow your analytical-thinking mind—which breaks things into parts—to rest and your holistic-thinking mind to play.

It can also be helpful to play with different questions to help you get a sense of what the system/situation/collective needs.

I invite you to play with these possibilities:

  1. Who do my decisions impact? This might include children, partners, parents, friends, clients, collaborators, comrades, colleagues, employers, employees, stakeholders, community members, or anyone else your decisions impact.
  2. What do they need and want? How might I find out what they need and want?
  3. What does the system need?
  4. What does the collective need?
  5. What does this situation need?
  6. What is in the highest good of the whole?
  7. Do I need to ask any questions to understand better what the system, situation, or others need? Who and what do I need to ask?
  8. Keep asking What else? Anything else? until you’ve written down everything that arises.

Often, it’s impossible to answer these questions or get the outside view on our own, so I encourage you to reach out to other people you trust and listen to what they think is needed.

If you take anything away from this love letter, I hope it is the encouragement to reach out to others for support. We can move so much farther, often so much faster, when we have insights and thought partnership from others.

I am wishing you all the clarity you long for!


[1] Daniel Kahneman, Thinking, Fast and Slow. (New York, NY: Farrar, Straus and Giroux, 2013.)

[2] https://www.fundera.com/blog/what-percentage-of-small-businesses-fail

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