A homeless couple I’ve worked with for several years recently described what they believe makes outreach actually effective. Their perspective matters—because they’ve been on the receiving end of nearly every kind of outreach imaginable, from well-meaning but harmful to genuinely life-saving. I come to this work as a journalist now, but for many years I was a homeless outreach worker myself. Most of what I learned came from failure. I watched people shut down, disappear, or lash out after encoun
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