I feel myself primed, tensed, spring-loaded, but still maddeningly sat on a precipice. I feel so profoundly open to possibility and change, ready for something—anything to happen.
Where does one find the chance of a lifetime? Is it constructing itself, rumbling underneath the banal mechanics of your daily life? Is it more like a sculpture, growing more corporeal, more possible, carved by your decisions, actions, and choices? Or is it something more ephemeral, summoned to you by the unknowable combination of luck, pluck, and timing?
I don’t know. But at this point, I’m squinty eyes glued to the horizon, scanning for any silhouette that looks and feels like The Big One. I also wonder if this somehow precludes me from it. If the wanting, yearning, seeking of opportunity repels it. I have a difficult time contextualizing my successes. When I reflect on my life, it’s hard for me to recognize having anything to do with it. When I look at my career, my relationships, everything feels like a right place right time stroke of absolute random luck. I’m not saying for a second that I was undeserving of the opportunities. It’s more a sense that my skills and attributes don’t necessarily feel like a factor in how the opportunities arrived to me in the first place. I am grateful for every single one that has, and I long for the feeling of gritted teeth and hot palms readiness that comes with walking up to a new chance, having no clear vision of what will come of it, and absolutely devouring it. Things tend to land on my plate, but that doesn’t make the path that led me here a straightforward one. I often spend my time fingers crossed for a happy ending.
My consulting career was borne out of my experience with homelessness. After a brutal assault in my early 20s followed by a string of bad luck, I found myself without a place to live. It still astounds me to this day how few crises we all are away from homelessness. A car breaks down, a bad bout of bronchitis, an argument with a parent—and boom—you’re on the other side of the margin, placeless in a world that demands we all spend, buy, and work to be a part of it. For me, it was a stroke of luck to experience homelessness in Boston. With its rotating calendar of conferences, all I needed was a dropped name badge to have something to do for the day, and a company name combined with a suggestible (or easily intimidated) concierge to have a room for the weekend. Age was also a matter of luck, to a certain extent. What should be obvious risk factors aside, being 21 in Boston without a place to stay was made relatively more survivable aided by what back then was a whole universe of Allston house shows, and other 20-somethings hopping couches, borrowing cash, or just generally dealing with issues with their parents too. So most nights I had good luck finding a place to put my head. Most nights.
The thing about homelessness that people don’t think is as much of a problem as it really is are the days. Our western, American capitalist world is not composed of many third places. We have the day made up of Working Spaces, Spending Spaces, Leisure Spaces (an extension of Spending Spaces) and the entirety of our life is scheduled around when and how we cycle through them. For example, there are very few places it is expected and accepted to see people at 6 am. Home, on the commute, maybe having a coffee. Certainly not rubbing sleep out of your eyes, on a park bench you’ve clearly been occupying for a longer than normal time. Unusual activity, which can really just boil down to doing something in the wrong place at the wrong time, is conspicuous, and when you’re homeless, being conspicuous is criminalized. More signs spelling out ‘No Loitering‘ than ‘No Littering’ says the quiet part out loud, making it brutally clear what’s actually important. In needing to avoid being seen, every day felt the same, and ended the same, like a slate wiped clean. Being invisible is a lot of work, and it doesn’t allow you much space for novelty and risk taking. Whenever I would go to sleep, no matter what had happened the day before, I would awake with the exact same set of problems. Running out of reasons why my phone doesn’t work. Running out excuses for why I can’t hang out or go out for dinner. Where would I eat? Where would I sleep? Where could I warehouse myself to avoid being caught? Caught sore footed, and red handed being the living, breathing, ever hiding personification of at least 3 systemic failures. Guilty of not dying or disappearing the moment I didn’t have a place to stay anymore.
This problem was somewhat remedied by daytime services. Thank goodness a combination of multiple generations of homeless youth, advocates, and policy makers identified a need for youth (18-25) focused spaces. So, though my days would take a Truman Show sense of repetitiveness, these spaces gave me a place to be, a sense of moving forward, even if just going through the motions of getting housed, or the illusion of progress. I had a case manager! My case was being managed! What that meant for me materially, I couldn’t tell you to this day. Was I the case? Was my lack of a house the case? In any case, it was being managed, and it made me feel better. The invaluable gift I was offered during this time was a deep sense of community, shared by other young people experiencing homelessness, and opportunities. That’s what the folks at Youth on Fire called them, or any service providers, really. The program manager would emerge, or some staff member with a sign-up sheet curled against a clipboard and announce some “speaking opportunity” or “writing opportunity,” or “advocacy opportunity.” They’d explain it, you’d go, usually they paid you in a gift card.
These “opportunities” built the foundation of what would come to be my career as a nationally recognized advocate and systems consultant, eventually taking me into the private sector where I actually became financially stable for the first time in my life. I don’t want to act as if these programs were perfect, or even net positive, because I don’t believe most of them were. However, they worked for me, or maybe i was just able to work them. These clipboards led to conferences, panels, and nominations. My network expanded from mentors, to sponsors, colleagues, to now friends of many years. When I consider my role in how this came to be, I don’t take much credit for the opportunities themselves, or the fortunate timing. What I will say is, I’m incredibly adept at recognizing when an opportunity has arrived, and not fumbling it, for the most part. I take the baton and I run, as long and as far as I can.
I think there can be something taboo about this kind of eagerness and determination to seize moments, and capitalize on luck. Ambition is tricky, and most of the time, models of success often come in the form of trophies held in bloody hands, every win a violent conquering, at the expense of another. I don’t ever want to win like that. The idea of chasing down opportunity, of seeking chance, of intentionally setting out to get something that I want brings up complicated feelings. I also don’t want to be fearful about the place of yearning that I’m occupying. Sometimes saying you want something, expressing that you believe you’re worthy of something can be the most terrifying and shameful thing. As I wonder what being a full-time writer could look like, as I dream into what cultivating a YouTube channel could look like, I’m almost instantly shutting myself down.
“What makes you think you’re good enough?”
“You think you could actually do that?”
“That’s so embarrassing, people are going to think you’re (insert literally anything negative and self-aggrandizing).”
However, on the other side of these creativity-mutilating thoughts, is a deep knowing tied to a deep fear tied to a deeper yearning.
Knowing: The only way to absolutely guarantee that I do not get to have the things I want is by not going after the things that I want.
Fearing: I am afraid I will never get the things that I want. I am afraid I will get the things that I want and destroy them. I am afraid I am not a person who gets to have things.
Yearning: I deeply need to express myself, and I believe what I have to make is important. Write, think, feel like your life depends on it because it does. We need this.
There’s a desperation to it. The deep pelvic pull calling us all into communion with ourselves. Our mission, our purpose hungering, requires requitedness. It’s so many Jamilas that needed to express, process, be heard that want to fill their lungs and take the baton, and fucking run. Not away, but towards, in the very direction of dreams and life, wounds and waking ups. So this Monday, I’m sitting on my bed, head full of dreams, thinking about podcasts, and the life of a Working Class Artist (a gift of a phrase from a friend of mine, Thanks Nathan!), of 6-month sabbaticals to write my book. I’m thinking of cold emails, putting myself out there, going and getting the god damn baton myself.
And I’m scared. I’m thinking about you too. Yes, you. I’m thinking about how if you’re here with me, a screen and a breath away, real and solid, then I’m not alone. Neither are you. So, If you think there’s any way I can lend you a hand, reach out. And if you see any opportunities on the horizon that are my shape and size, send them my way.
In the spirit of joining hands, and active pursuit of our dreams, I offer you a prompt, in closing:
Take a deep breath. Call into your mind a moment you were at the edge of an opportunity, anticipation flooded with a new reality shimmering just beyond your sightlines. Remember the fertile feeling of the moment, the “something is about to happen” buzz that lets you know you that it’s almost time to leap. Hold that feeling of prospective prosperity and keep it with you through this process.
1.) Let your heart write a list of what it needs, yearns for, seeks to fulfill. Not your head, no what ifs, or “possibility detectors.”
2.) Pick 1-2 from the list. Think about two 5-minute activities that could bring you closer to that yearning. It doesn’t necessarily have to bring you closer to obtaining it, it merely needs to bring you into closer contact with the need itself.
3.) Do those 2 activities, write down how you feel after.
Reach out to me and tell me how it goes, if you feel called to. My DMs are open.
In kinship,
Jamila
💕BONUS CONTENT💕
To my beloved paid subscribers, I’ve decided to include some personal moments + anecdotes, photos, videos and writing from my time experiencing homelessness and my journey through. I offer you my vulnerability, small and tender moments from my past self as an expression of gratitude. Thank you for supporting me.
During this period of my life I was in the first years of what would grow into a 10 year period of estrangement from my family, and I never shared my homelessness with anyone I actually knew. I lived a double life until I got housed and was able to integrate them. I feel honored to let the Jamila who carried me and our shame through these years have a voice, to let them be seen and loved. If you happen to have known me through these years, and are still in my life, I am eternally grateful to you too.
I’ll try to keep things chronological, but no promises.
2014 was my accident. A little bit after the assault I was back in the hospital because of some abdominal pain, which turned out to be some internal bleeding and glass particles. I’ll spare you the details. After some bad luck with my family dynamics, I ultimately ended up in Boston, unable to pay my rent recovering from my first of many laparoscopic surgeries, with no place to go. Of course, as the cringe laws of 2014 demand, I documented it on Facebook.
April 2015. I was homeless homeless and I learned the reality of unintended consequences. One day while I was leaving Youth on Fire to figure out where I was going to go, a photographer stopped me. He was doing a project called Portraits of Boston. I told a bit about my experience, what I was going through, and how my life had changed. Weeks passed and suddenly I was inundated with tags on Facebook. My portrait had been selected and posted (it’s still up if you want to read Part 1 + Part 2 or need a reminder that the internet is forever. the comments are unreal.)
Several of my family members and friends of my mother were in the comments absolutely enraged. It blew up in my face, and as I type this, I’m cringing as I revisit myself recanting my own experience of homelessness out of fear of embarrassing my family. Literally rejecting resources offered by empathetic subscribers of the page, out of shame and guilt, feeling as if my predicament was not only my fault, but also a tarnishing to the reputation of everyone around me. I’m squeezing the child in this picture (below) with all my might.
Here’s the life altering text that cemented 10 years of estrangement, and countless other joys, wonders, changes and horrors. Hindsight is a wild thing. I was afraid to read this, to be remembered in this moment, and I am shocked at how completely unproblematic it is, and how truly dire my situation was at that time. I am astounded at how openly and casually respectability was prioritized over my life. Somebody(s) owe baby Jamila some big apologies.
Part 1:
“I moved to Boston last summer. When I went to a work party, I was badly beaten and then raped by four people. I was in the hospital for a month, so I lost my job and all the friends I had made. I literally knew no one in the city, and I had to start from the bottom. I got out and spent a week with my mom, but once she saw that I wasn’t the same person anymore, she kicked me out of the house. I still had stiches from the surgery, and I was out on the street.
“I’ve never really had people—every time I rely on someone, I end up in a terrible situation, which is why I’ve become defiantly self-sufficient. You can’t let another person decide whether you’re safe or not, or whether you’re housed or not. Those are too big of things to leave to outside variables. I actually get more hurt when I expect things from people—like expecting my mom to do the right thing and being angry with her for not doing it.
“So I just seek out fictional alternatives. I read books and associate really deeply with specific characters—I use them as mother or father figures. Or I watch movies and do the same. Those people comfort me because they have things to say that relate to me. I’ve always been big on figurative alternatives. That way I don’t have to be angry with my mom for being something that she’s not. Asking her to be my mom is the same as asking her to build a church. She doesn’t have the tools to do that, and it’s not her fault. She just got saddled with a job that she didn’t know how to do.”
Part 2:
“The craziest thing about being homeless is that everything you know how to do—get a job, work—none of those things apply anymore. None of those things will keep you safe or help you get back on your feet. You have to relearn or rediscover how to survive. It’s really primal, animalistic, crazy. You have to use parts of your brain that you’ve never had to use: Where is the safest place for me to sleep outside? Where’s the safest place to get food without being harassed? Which shelter can I go to without someone doing something terrible to me? You don’t learn how to be homeless in school.”
“Why do you feel that trying to get a job doesn’t really help you get back on your feet when you’re homeless?
“Well, what do you put down for an address when you apply for a job? How do you show up for work on time if you don’t have money for a bus pass? How do you show up for work looking clean and presentable when you just slept outside in the park? Are you going to show up for work with a suitcase and a backpack because you have to carry your possessions with you all day? I had pretty severe post-traumatic stress disorder when I became homeless, so I couldn’t physically bring myself to get on the train. I would sit down and all of a sudden lose three hours. I was having a lot of issues disassociating.”

This was in 2015, for the opening of Y2Y Harvard Square, first ever youth led, youth run shelter for young adults. As you can read, I have never shut up and also spoken pretty intensely for a very long time. Baby Jamila was no word mincer. I had been been homeless, gotten angry about it and now set my attention on solving it completely. A lot had changed, and I was starting to think I was going to be okay. I was right. I ended up serving on the board for awhile.
My first (and only) piece published writing also overlapped with my period of housing instability. It was an opportunity that came by way of Youth on Fire, the drop in center I would frequent during my days. This particular opportunity was emailed to me, and if I remember correctly, wasn’t a guarantee, due to a selection process with a few other writers. The piece is titled ‘Welcome Home’ and was published in Architecture Boston’s December 2016 Issue. I was paid $50 for the piece.

My life became flooded with meaning and purpose and direction. I had friends, I was reading, writing, even starting to dream again. I became a facilitator, a policy consultant, and I was good at it it. I decided I was never going to get a high school diploma. I stopped explaining myself. I made speaking up my job. I co authored






This is the press announcement for my first real life adult job following getting housed, and I was such a baby in this photo. I was the aide to Vice Mayor Marc McGovern. He was a fantastic boss and an even better person. I didn’t leave the job on the best terms, but it remains a life changing opportunity and an incredibly important chapter of my life, largely due to Marc. I think I was still processing a lot of the trauma of my experience, and unsure how to manage responsibilities, and what also would become the beginning of the health symptoms I’m learning the name of now.
I doubt anyone will sit through these but it felt right to include them. I want this person to be seen and heard and I feel lucky to have this stage of my becoming caught on video occasionally. This took place at a conference that I was invited to speak at in the very very early stages of my career. I didn’t quite understand the concept of business casual, but I still think I looked fabulous. I wasn’t completely broke, totally destroyed credit, and waking up to the possibility of having, being and doing more than I’d ever imagined.
Closing words: My first and absolutely disastrous TV appearance. Zero media training, zero facial awareness, enough said.
Thank you for spending time with me here, in this period of my life.
Thank you for supporting this new chapter.