20 Years…
Migrations, career building and changes, awards, recognitions, failures, moves, love, death, publications, stages, marriage, family, pandemic, philanthropy, none profits, entrepreneurship, and everything in between.
Today is a significant day for me…
20 years ago today, on a very cold November night, I found myself homeless on the streets of New York, and several months later, I walked through the door of a tiny basement studio apartment on East 32nd Street and Kings Highway in Brooklyn, after months of living on the streets of New York in the heart of Chelsea area.
Here I am, living in North Bay, California, just about 45 minutes outside of Napa Valley and 55 minutes from San Francisco (with zero traffic), in my home office, at my 8 foot standing desk, sitting on my Herman Miller office chair, typing on my MacBook Pro with Studio Display attached to it, with my iPad pro to the right of me, AirPods Max on my head, listening to a nice focus music on Spotify, wearing my Moscot glasses to see better what I’m typing here… and paying $50 for a take out dinner just because my wife felt like Thai tonight, didn’t make me flinch even for a second.
But not in a so much distant past, a $1.75 slice of pizza and cup of coke for dinner was a 10 minute decision making process if I should spend the money or not, and a good night sleep was an old bench at a subway station with hopefully no one around for at least 3–4 hours to get some uninterrupted sleep for a bit, office was a random table at a local Starbucks, and water, well, water was a small walk of shame into a random coffee shop or a bar, asking for it, hoping a person looking at you, and judging you, would feel generous enough that day to waste a paper cup on you and few minutes of their time to fill it up with tap water.
It is surreal sometimes to think about it… I frankly dont think about it too often, but sometimes, just sometimes, I catch myself remembering these days, how it felt, how I felt, and how I feel today, how greatful I am to be where I am.
I sometimes sit in silence with myself and can’t believe it, I used to be homeless, not in a sense of between apartments and couch-surfing at my friends places for a bit, no, like seriously, really, actually, homeless, no money, no income, no food, no home… Just me, the streets, other homeless, and society that puts you in a very special box, a box that very few manage to brake out of, its not hard to adopt, really, first few weeks are fucking hard and terrifying, but then, your brain figures out how to manage, how to live that life, adopt, shift, and live it… and you know what, even sometimes smile and find joy through all the sadness and despair.
But I honestly sometimes look back in complete awe of how I just got out, I mean it didn't happen accidentally, or I wasn’t given a gift, no one discovered me, and it wasn’t a miracle, it was me, clawing my way out, one step in front of the other, one act, and one decision at a time, with a clear goal, no plans, no missions, no 5 year strategy, just one simple goal, OUT.
I still believe that I owe this to where I came from, how I was raised, and more importantly by whom… my parents are the bravest strongest people I know, we are Soviet Jews, and for those of us who know what that means, know exactly what I’m talking about, we are built different, we don’t see blockers, we only see obstacles on our way to our goals or aspirations, we don’t make plans, or vision boards, we set goals, but never timelines, because we know that we will get what we’re after, if takes 5 years or 20, we will get to our destination, with focus, rigor, hard work, commitment, and zero distractions, we reach it, doesn't matter when or how, what matters is the where.
I don’t want to retell the entire story all over again, I already wrote about it, and I’m not gonna lie, I didn’t really wanted to write about it, someone that was in my life at the time managed to convince me to write about it, I still feel like it was maybe a mistake to open up to the world, write about it, share the journey, almost felt like I was looking for pity, but I wasn’t, and am still not, random people throughout my life, the ones that I did open up to about this, said I should share the story, I should write about it, someone even suggested I should do a TED talk about it.
But here is the thing…
While I was writing the first story about my homelessness, it felt good, it felt liberating, and really helped me work through some seriously and deeply buried trauma that’s been with me all these years, to the point that my brain even blocked some events out of existence, and brought it back for the first time two years ago when I was writing about it, so yeah, it was liberating, freeing myself from the burden of feeling that I wasn’t good enough and had to prove myself my entire life just because of that chapter of my life, I felt that I had to hide it, avoid it, and make sure no one would ever find out about it, because I was afraid, I was afraid, and sometimes I still kinda do, that people would look at me differently, maybe even with some disgust “Oh man, this guy used to be homeless, ate scraps, smoked cigarette buds that he picked up on sidewalks or public ashtrays”.
So I kept it inside, locked and tucked away, never to show that my life was anything but perfect, and that I had to sleep on the floor of my first apartment for the first 6 months after walking through that door, using my only coat as a blanket, eating on the floor, working on my $400 HP laptop that could baely carry the weight of Photoshop when I worked on design projects, but I would patiently wait for it to render something, move 10 pixels graphic for 5 minutes because of how heavy the file was.
Nonetheless, I was proud, I was proud to have a place I could call home, finally, and make a bit of money from a craft I loved, and be able to buy food, basic, minimal, but still food, and buy my own cigarettes and not pick up buds of the street.
But in those moments, I could never imagine, even in my wildest dreams, of where I was going, what will be next, and how my life would turn out to be…
Get Yan Grinshtein’s stories in your inbox
Join Medium for free to get updates from this writer.
Art director working with such brands as Microsoft, Volkswagen, Deloitte, BlackBerry, Sony, and hundreds more, photographer who wanted to just take photos, but somehow ended up being published, award winning, and lecturing on the subject of street and documentary photography at a museum and university.
And doing some wild things along the way… launching a non-profit in Israel, being featured in a Forbes equivalent Business Magazine in Israel, finally moving back to New York in 2014, this time as an accomplished designer, art director, and photographer, pivoting into UX space and starting from scratch again, just to rebuild my career all over, and again, going from entry level UX designer to Head of Design in a span of just 5 years, increasing my income from $60k to over $300k in just 6 years, creating and running a non-profit project with Starbucks serving food and hot drinks to the homeless in Brooklyn during winter months, mentoring and coaching over 2,200 designers and design leader from some of the largest companies in the world, organizing PPE shipments to New York Hospital and local grocery stores during the peak of the COVID19 pandemic PPE shortages, and making New York my home for a decade where I met my amazing wife, bought a house, and got an awesome dog, before moving to California mid 2025 to focus on my company.
So here we are… end of 2026, what a wild ride it has been thus far, but this is not where my story ends, this is where it begins again.
Some might say I’ve lived many lives, and they are probably right… first 10 years of my life I spent in Soviet Union (Ukraine USSR), the next 10 years I spent growing up in Israel and serving in the military, then 6.5 years in Canada where I learned web and digital design, then a year in New York going from homeless to working with one of the largest Law Firms in the state, then back to Israel and building a succsseful design career, and photography recognition, then, back to New York to build my UX and Design Leadership career.
Most people would say that’s it, I’ve arrived, gone through lots of hardship, built a career, solid foundation, family, I’m good! Now, chill and enjoy the fruits of your labor and long years of hard work, sacrifices and dedication.
But I guess not me… I was never able to sti still, I always wanted to do more, know more, try more, learn more, be more.
So, early 2024 right after my 44th birthday, I told my wife I wanted to start a business, I’ve spent a decade across tech startups, and just love the environment, my best work, imagination, and innovation shined through working crazy startup hours and living the startup life, and so I decided to start my own… the problem though, becoming a tech founder, meant putting yourself, and now your family alongside you, through some serious heardship, stress, and risks.
But, I felt deeply that I had to do this, like with every molecule of my being, I just had to do it, and when you marry a life partner that not only supports your dreams, but also truly believes in you, the hardship and risks feel less terrifying to some degree, but it does not make things easier… I wrote about that too, a very personal and deep retrospective of 2025, sharing the rollercoaster I’ve gone on again, losing the high income, depleting our savings, and having to sell the house to keep going, downsizing our lifestyle and going from 1,800 sqf house with a massive back and front yards, to an 800 sqf apartment.
It can feel like I’m going backwards, it took me years to get to top, to get to a point where both Google and Meta tried to hire me for years, at times offering over $700k in total comps, and a Fortune 100 company giving me an offer without even interviewing me… and now, I am working 12 hour days, 6 days a week, stress, sleepless nights, constant rejections, self-doubts, constant learning, and doing things I really dont like doing… like sales, prospecting, cold pitching, asking for money, etc.
But… none of that matters! I wouldn’t be here today without all of the hardship, and the many lives that I have lived through and experienced, and this is why I know that I will build a generational company, solving some of the worlds biggest problems, and leave a lasting legacy for my family and build a better future for the human kind.
As I am marking this day, I want to leave you all with an important life lesson that I’ve learned along the way…
Wherever you are in life, and whatever you do in life, NEVER make money your number one priority and focus, life is an interesting thing, when you concentrate on the right things in life, money follows.
I know it might sound counterintuitive, we need money to live, to eat, to survive in this world, but if I learned anything through all the rollercoasters, countries, and cultures I have lived through, money is not the most important thing in life, along the way my life journey thus far, I have met thousands of people, from former homeless like myself to ultra wealthy, and I noticed an interesting pattern, people who chased money as their number one life goal, were not always wealthy, but were always unhappy and didn’t like their life, no matter how much money they had in the bank, but people who had different goals in life, such as learning new things, being helpful to others, solving problems for themselves and others, inventing something, experiencing something, building relationships, etc. were not always rich in a sense of how much money they had in the bank, but were always happy, satisfied with their lives, and liked their life.
On my journey, I never had financial goals, but I always had and still do life goals, money comes and goes, I can become a multi-millionaire tomorrow, and loose it all the next day, but the one thing I cannot gain overnight and lose overnight, are wealth of knowledge, experience, and relationships, I have never measured my wealth by my income, bank statement, or what I own, but rather by how much I know, my experiences in life thus far and hopefully learn and experience more, and the relationships I’ve built, and how many people I’ve helped.
Money will come, I know it, but everything else, we all gotta work really hard for… and I guess thats the little wisdom I’d like to leave you all with as I am wrapping up this article.
If you made it thus far reading my ramblings and thoughts out loud, I have a single ask, mark this day with me but doing one, just one act of kindness, it can be buying a homeless person a cup of tea or coffee, helping someone carry their groserries, giving someone your umbrella on a rainy day, just one, today, for me.
Thank you kindly for reading, and for being kind today to another fellow human.
With warmest wishes,
Yan
