Jenny and Shana, Urban Pioneers

I was seventeen and class was being held outside, under the tall pines at Fort Miley near Land’s End, atop sharp cliffs overlooking the ocean. We sat in the shade of those trees, their dried needles creating a billowy cushion on which we formed a circle and discussed the day.

She was upset, though that wasn’t new. It had been a long day of trials and tribulations at the ropes courses, designed to make us face our fears, build trust and stir emotion in the most stoic of contenders. We were all spent.

I remember hearing the waves crashing against the rocky shore in the distance. I remember the look on her face and the tone in her voice. I don’t remember what she said, only that her intentions were clear when she ran off towards the cliffs, and that no one believed she would do it.

But I remember what he said. “Jenny, go get her.”

Lots of things ran through my mind in that moment, and going after her was not the first.

Why me? That’s not my job. You’re the adult, you go. How could she do that? I could never do that, such a public cry for attention. I want that attention though. I’m hurting too.

Whenever I feel like I need support but don’t know where to turn for it, my mind brings me back to that day. The day I unwillingly became the person who gives support and learned that getting it requires extreme measures. Yes, that was the lesson that day: getting support requires extreme circumstances and extreme measures.


I wrote those first few paragraphs months ago, with every intention of regaining the momentum of an at least monthly newsletter after my hiatus earlier last year. I would open my draft and read it and rewrite it. I’d tweak a sentence, a word, and I’d rack my brain to find the connection—the next anecdote, the metaphor, the story—for the text to take me somewhere.

But I found nothing and went nowhere.

Eventually I squeezed out those last three painful paragraphs. The paragraphs where I was able to admit this misguided lesson I had learned. And I sat in that pain and the sadness that I hadn’t learned better. That to this day I still struggle with support, feeling that I give more than I get, and that asking for it seems out of reach, like something only for other people.

I started asking myself why. Why is it so difficult to find support? What it is that I expect? What is it that I really need? Why does it still feel like it requires extreme circumstances or measures to get it?

As I went around in circles trying to make sense of this lingering topic—support—that I was convinced was too important to ignore, I came back to my original tale, to that day at the ropes courses. I thought about him and about that program. I’ve written about them before: Urban Pioneers and Wayne MacDonald. Despite my ill feelings toward him in that moment, Wayne was a mentor to me, to her, to many. That program helped save my life, a life that was otherwise in a downward spiral toward nothing good.

I opened a new document and started typing:

Things I learned at Urban Pioneers

  1. Give me a fish and I eat for a day, teach me to fish and I eat for a lifetime. (this was our class motto)
  2. Only pack as much as you can carry.
  3. Mold adds flavor (or don’t discard too readily what looks ugly or rotten).
  4. Dig your trenches, wax your matches and don’t forget the iodine (be prepared for the worst).
  5. Trust that someone will catch you.
  6. Be ready to jump naked into a sleeping bag with someone, feed them, or guide them through the dark.
  7. How others see you may be different from how you see yourself.
  8. Facing your fears is its own reward.
  9. Someone always has it worse off than you do.
  10. We can live with a lot less than we think.

Urban Pioneers was a semester-long alternative program for kids who didn’t fit in anywhere else. We were the troubled youth, the rebels and the restless who, for different reasons, couldn’t conform to the classic curriculum of public high school. I spent my whole senior year there.

At the ropes courses we would overcome all sorts of obstacles involving rope ladders, nets, harnesses, and leaping to catch a trapeze 40 feet in the air. We volunteered in soup kitchens, at schools for disabled children, and helped shovel the debris out of people’s living rooms after the big earthquake of ’89. Each semester we took a two-week long survival trip in the California wilderness, carrying our own weight, pitching tents and fighting whatever the elements threw at us. I hurled myself face-first down an 80 ft. cliff face. I dug trenches in the dark and the pouring rain with a spoon. We fed each other, shared our victories and failures, shared our fears and were vulnerable in front of one another. We all got a glimpse of who we were and what we were capable of. We didn’t all like each other, but we got through it together.

This further trip down memory lane reminded me a few things about support:

Support is not help

Help is concrete, tangible. It addresses a problem, an obstacle, a situation. Help is about trying to fix something or find solutions.

Support is abstract, subjective. It offers encouragement, understanding, love, and even boundaries. Support is about sharing the weight.

No one could have helped me make the leap for that trapeze as I wrestled for hours with my fear while standing 40 ft. off the ground on a wooden disk no bigger than a Frisbee, wondering if she would catch me if I fell. Everyone did, however, support me by patiently waiting as I battled my demons, encouraging and reassuring me until I finally made the leap.

You’ll be happy to learn that she didn’t jump that day at the cliff, but she did catch me the day that I jumped.

Teach me to fish

Why is it difficult to receive support? Because we make ourselves vulnerable. We’re afraid to be seen as weak. We don’t want to burden people with our problems. We’re afraid of being judged. Sometimes support doesn’t come in the form we want it to. Because we don’t want help, we don’t want someone to try and fix us or our lives.

Why is it difficult to give support? Because it’s hard to reserve judgment. We have our own problems. We can lack empathy and therefore can’t understand. We can have too much empathy and therefore feel others’ pain too deeply. Because we don’t know how to listen. Because we don’t know it’s needed. Because we just don’t know how, period.

Because in the same way that it’s easier to talk about and treat physical pain rather than emotional pain, it’s easier to talk about and give help rather than support.

We need skills

Urban Pioneers existed to create support for kids who were otherwise falling through the cracks. All of the lessons we learned, the experiences we had, the challenges we faced, were designed to support us by teaching two essential life skills: trust and self-sufficiency.

Without trust we isolate ourselves, put up walls. Without trust we can neither give nor receive support readily because it means making ourselves vulnerable: vulnerable to disappointment, vulnerable to exposing our shame and insecurities, vulnerable to not having our caring reciprocated.

What if I come to rely on that support and it goes away? The truth is that we can’t always rely on other people. People do often let us down, because we have expectations of them, because they are fallible, because our expectations aren’t realistic.

Building trust means learning first and foremost to trust ourselves, and this gives us confidence. It means learning to rely on ourselves. In order to rely on ourselves, we need tools and we need to be willing to do the work: to dig the trench, to follow medical advice, to take care of ourselves, to fasten our own harness, to take the leap.

Being self-sufficient is taking responsibility for ourselves—looking within—before we can ask to share the burden. Because if we don’t, then we are the burden. And if we come to that point, we will need more than support, we will need help.

Learning to fish

Support happens in subtle and not so subtle ways. It is often there without having to ask. When we are feeling deprived of it, it’s easy to go to a dark place and remember the worst, to think that that’s all there is.

My journey ends with a profound realization: my feelings of lack are most often associated with expectations I place on other people. My spouse, my friends, my family, my coworkers.

It doesn’t matter if I’m right to have such expectations. It doesn’t matter that I deserve support. What matters is that god-awful feeling of lack and loneliness and what I do with it.

It’s no secret. In the end, if you are not getting what you need, then you have to ask for it. But I have developed a tool to help me through that transition of god-awful feelings that make it easy to put off the asking, or that make me particularly ungraceful when I finally do: taking the expectation off of the other person, and placing it on myself.

Placing expectations on people is really easy to do without even realizing it. It’s also unfair, because such expectations are rarely spoken, they are instead assumed and wrongly so. By shifting the expectation away from autrui and on to myself, I refocus all of the displaced emotions that go with, and I free myself to do two pretty amazing things: 1) figure out what it is I really need, 2) make the task of asking for support much easier. Because I am no longer blaming others for their perceived shortcomings. Instead I am taking responsibility for my own needs and giving others an opportunity.

Because many of us are willing and able to help, and many of us really enjoy giving support. Giving is a gift that we simultaneously offer and receive.


“Courage comes right at the whisper of secrets tumbling out and the light shining through them.” –@mandaviviers

PS: yeah, that’s me on the left, but no, that’s not her on the right. Photo by Noah Sulley, and thanks to S for agreeing to let me use it on this post 😘


This text is originally from my newsletter, Making Connections, and may have been modified for publication here.