Street Smarts – San Francisco Bay Area Exec’s Lessons As A Homeless “Street Person”

homeless prada

Note:  This story occurred in 2000 and I initially wrote about it in 2002.  Since that time it continues to run in local papers, usually between the Thanksgiving and Christmas.  I have more recently added a few “epilogues.”  – Bob Fagan

(Bob Fagan, a Pleasanton resident, is the Western Vice President for The Callahan Group, Inc. and specializes in mentoring and personal coaching of CEO’s and top management as well as aspiring and world-class athletes. He is about to publish a DVD and audio CD on applying The Law of Attraction- a sequel to “The Secret” together with two similar products for golf and business leaders. A former golf professional, he has a background of more than twenty-five years in the corporate world, which has included startups and turnarounds at the CEO-COO level. Mr. Fagan would invite feedback and may be reached at

I’m not much different from many East Bay dads or businessmen, but awhile back I stepped out of my safe, secure suburban existence and spent five days and nights living on the streets and sidewalks of San Francisco.  To say the least, it was an enlightening experience with some unexpected surprises. Maybe the most significant lesson from the whole escapade took nearly two years to realize.

By way of background, I am a fifty-year old divorcee, the proud father of two wonderful teenagers, and call Pleasanton home. I have owned some modestly successful businesses and headed up and turned around some organizations in a continuing career that now has included startups. There is nothing too remarkable or unusual about me except that no one would ever picture me as a shabbily dressed homeless person existing on the sidewalks with not even a blanket or tarp. Hardly street savvy, many of my life lessons were more apt to be gained on the farm fields of southeastern Pennsylvania, the playing fields, or in the Boardrooms rather than the streets of San Francisco.

As life would have it, you sometimes do crazy things. Why did I do this? It was mostly to “stretch” myself and step outside my comfort zone, hopefully learn something about myself, and simply experience life in a more unique fashion. Also I was curious about how some of our less fortunate live and endure. And finally, part of me wanted to search for God’s force or Source Energy, wherever it might show up. I chose the week before Thanksgiving to become “homeless” in San Francisco – to literally live on the streets. Following the ending of a long-term marriage five years earlier, my life had typically been so busy with the children and work, and trying to start a dating life. With my children and lady friend out of town, and just having finished an assignment as President and Chief Operating Officer of a Berkeley-based E-commerce software company, there was a perfect window of opportunity for time off. No one knew of my whereabouts except for leaving an answering machine message that I was “away and out of communication until Thanksgiving.”

Working in cities from time to time, I have long observed those weary tattered folks, pushing a shopping cart or curled up over a heat vent or asking for a handout. If you are like me, you have noticed them too. Perhaps you have avoided them, afraid to make eye contact, or maybe you have shown them compassion and dropped some coins their way. More than likely you have not been too comfortable in their presence. Besides many are dirty, sick, or in some way disturbed. Some might be dangerous. Others can be obnoxious. Now, just for a moment, consider what if the tables were turned?  What if you or I were on the streets?

Would living on the streets be uncomfortable, dangerous, degrading or humiliating? Where would I wander? Where would I sleep? How would I eat? Showering? Not likely. Would I be hassled or helped, threatened, harassed or welcomed? Would I stay with my challenge or quit?

My preparation for this special sabbatical was minimal. I stopped shaving a few days ahead of time, delayed a haircut, and for about 24 hours ahead of time, I only drank water. If this was going to be any kind of worthwhile experience or test for me, I should be hungry and properly grubby. As far as personal items, I took a pocketknife, a magic trick, $25 in quarters to give away, and twenty dollars stuffed into my socks for emergencies. Because it always feels chilly to me in San Francisco, I wore five thin layers of clothes up top and long underwear and old blue jeans below. Some old shoes that were ready for the dumpster and a faded red hooded sweat jacket with an old knitted green and white stocking cap completed my attire. As my contact lenses would be impossible to maintain in such an environment, my coke-bottle thick glasses would be a fitting complement to my outfit and grubby salt and pepper stubble of a beard. Whether I was recognizable or not is debatable, but I did look “uninviting” to say the least. Now I must add, my ace in the hole was that I did possess a return ticket to the Dublin/Pleasanton BART station with my car parked there waiting for me.

So what did I learn those few days living on the streets with virtually no identity, ties, or shelter? Well, to be certain, missing the normal daily hygiene needs and the comfort of a dry, comfortable house and bed was to be expected. My first shock was witnessing nearly two-dozen men and a woman choosing to relieve themselves during a two-hour period on the Market Street sidewalks that first night. Next it was really problematic to find a place on the concrete to lie down that did not have the stench of urine. I finally salvaged a small piece of cardboard to rest my shoulders and head on. Next I was really surprised how noisy the city was late at night with street construction work all around. About 2 a.m. the first evening I fell into a deep sleep only to experience two sharp pokes in the ribs. Looking down at me was a fellow looking far older than his years hunched over asking me if I had any “smokes or coin?” Though the man was harmless enough, I then realized that when I was asleep I was physically vulnerable. I never did sleep quite so well from that time on.

The first two nights were quite cold and damp. In fact, the temperature dipped below freezing, the coldest nights in years. I found myself crawling into commercial buildings on my hands and knees to avoid security every so often so I could warm up for a few minutes. The evenings, however, were therapeutic, a great time to meditate, reflect, and walk about the city in quiet solitude. The days were quite another thing.  Nothing could have prepared me for the emotions and loneliness I encountered during the day.

Just five days, they dragged on and on. Sitting on the sidewalk or standing aside a building for minutes seemed like hours, and hours. Here I was in the midst of hundreds of people and never have I felt so alone. Whether I was situated on busy Market Street, in the Tenderloin section or near a homeless encampment, everyone I saw had a purpose, to do an errand, get back and forth from work, go shopping, meet someone for a meal, enjoy entertainment or a friend. What’s more, I assumed they would all enjoy a soft, warm dry bed and a hot meal that night. Me, I had nothing, no purpose, no responsibilities, no acquaintances, nowhere to go, and no one in the world knew I was here. I never did expect a “normal person” to engage me, let alone make eye contact, but I never anticipated the loneliness that would accompany having no purpose. It simply didn’t matter to me or anyone else in the world what I was doing or where I was regardless of whether it was 7:30 a.m., 10:30 a.m., 1:30 p.m., or 4:30 p.m. Sure, I could pop into some bookstore for a short time, but under the circumstances, even that grew old. If someone is a sane, sober person, I can now appreciate how and why they could lose either their sobriety or their sanity. Before I could not.

Yes, the days were pure hell. They simply dragged on and highlighted my loneliness. The reason was that I was completely stripped of all relationships. Typically those homeless have very few if any relationships, which is the saddest twist. Come to think of it, with a friend this whole homeless experience could actually have been fun, but I would have totally missed my lessons. My solo expedition was not fun. Though I am slightly on the introverted side, those seemingly endless days on the streets of San Francisco drove home how much I need people in my life. Besides, isn’t wonderful to share memories together with someone?

Properly hungry, I frequented the back door and dumpster areas of restaurants, hardly the table cloth and fine wine decor that I usually associate with my upscale San Francisco dining experiences. Standing outside some of the Union Square establishments, I was ushered on, to keep moving, as opposed to being accustomed to being welcomed in. Fast food establishments were my restrooms of choice, a place to take a paper towel bath. (Longer term good personal hygiene would be a virtually impossibility.)

In the early morning, I was never at a loss for reading. The homeless like me can peruse The Wall Street Journals and New York Times that are cast on the sidewalks long before their owners arrive. I would recycle those papers later stuffing them inside my clothing to try to keep warm against the damp night cold. I quickly learned that many homeless would commandeer a blanket, tarp, or shopping cart with the more enterprising building their own mini-shelters. My only protection was plastic trash bags that I scrounged from the trash and poked a hole in the bottom to put over my head for the heavy rain I encountered on my third evening.

Taking BART into the city, I was wondering if I would engage any of the other homeless in conversation. Would I encounter down-on-their-luck professionals? Soon I deemed it better to keep to my own business. Interestingly I must have encountered maybe two hundred fellow drifters and less than a dozen I could identify as women. Most of those people were sadly mentally or emotionally ill or the casualty of drugs or all. The vast majority appeared fiercely independent, though most would be quick to accept any charity cash, a drink, a drug fix, or food; and cash is king. Other than a few other homeless talking at me, none really talked to me. I heard many strange conversations, anger, and requests for money. It was here that I dispersed my stash of quarters to my fellow squatters with a smile and some encouraging words, and would then move on. No, I cannot boast of any interesting “new friends” and in a real sense again that was part of my experience, the loneliness.

One of the liberating aspects of being homeless was the complete sense of freedom, but at that high cost of loneliness. No one came to arrest me though I did not try to provoke anyone. Yes, a few times I was asked to “move on.” No security guards ever discovered me sneaking past them; many were asleep. Neither did anyone ever offer to help me or direct me to food or shelter.  Had I really been desperate, I could have entered a church or police station and sought assistance in a homeless shelter. The thing is that most of the people on the streets do not want help either. They live a very independent life of freedom, no mail, no bills, no bosses, and no responsibilities. Survival appeared to be their primary and possibly only purpose. For many, it appeared that drugs or alcohol might be just as important to them. Yes, life on the streets can be numbing.

In an interesting sidebar inspired by the movie, “Pay It Forward,” I chose to beg for money on my fifth and final night. Armed with an outstretched arm, a cup, and a hopeful smile, I had fourteen people or couples drop coins into my cup during a two-hour period on Market Street. For each who did, I gave them a dollar bill from my emergency stash in return. Eleven of the fourteen were dumfounded by my gesture – the three others were likely frightened and hastened to escape me. To those I could communicate with, I simply told them to “pass it forward” and “thanks for showing heart.” It made me feel human again; I had been starting to wonder.

What I would have given for a blanket or sleeping bag!

It was my final morning, the day before Thanksgiving, and at 4:00 a.m. I was ready to go home. I had weathered the cold, the rain, the dangers, and my loneliness. Another day was not going to prove anything more, and I decided to utilize my BART ticket back to Pleasanton. I had stretched beyond my comfort zone, enjoyed much solitude, and had a better appreciation of what living on the cold, hard concrete is like. No fun.

By 7 a.m. I was home in my familiar warm, safe surroundings. The first thing I did before entering my house was to strip down in the garage and toss my clothes in the washing machine, then take a long, welcomed hot shower, followed by a late morning nap in my cozy, warm bed. Later, rested and clean, I called people to reconnect and made sure to tell my children and girl friend how much I loved and missed them. (I waited until later to reveal my urban adventure.)

The life lesson that immediately hit me was that I, as well as most of us in America, live a life of abundance – more than a billion people would instantly trade for my worst days. I concluded that you could take everything away from me except my health, my time, and my relationships, and I would still be a very wealthy man. That’s a powerful thing to internalize. That realization has since led me to a greater contentment with life in general. In the mean time, the company I had been helping to start lost its funding and closed and, like many, my savings portfolio suffered some significant losses. These were hardly the circumstances I had anticipated; yet now I was better prepared than ever to cope with them and go happily forward minus the stress.

During the next year and a half as I recounted my story to friends, I was encouraged to write about it. I delayed because I did not want the theme to focus too much on me, but rather the experience, and I hoped to find and offer some revelation that might benefit others.  It was not until writing down my thoughts for this article, that I discovered the real epiphany, the “Secret.” In our nice little pocket of Northern California affluence, perhaps this message is particularly relevant.

It finally dawned upon me. The more important lesson was one just as powerful as that newfound appreciation for relationships, health, and time.  Simply stated, each of us is presented every day with a life-altering choice. That choice is whether or not we choose to be content with what we already have. The challenge for me has been an acquired taste and an appreciation for the better, finer, faster, smaller, more powerful, and more prestigious “stuff.” I now realize that when that appreciation becomes an appetite, it creates stress and puts things out of balance. Whether a newer car, a more lucrative investment, faster gadget, fancier dining and nicer abodes, or a higher salary, etc., those items are exciting only for a short time. When they become engrained in everyday life, I (we) take them for granted and they stop bringing contentment. Remember that great raise you received several years ago, the nice car or big screen TV you bought, or that fancy house that you finally moved into?  How exciting are they now?

Many of us are constantly racing through life, failing to stop and appreciate the many blessings we have all around us. We are racing toward the future, be it an appointment, a vacation, a retirement, or even a relationship. What if we were to simply step back and observe, and appreciate?

It dawned on me that I was setting myself up for recurring dissatisfaction. Whatever is going on in our lives, we immediately adapt to and then it becomes a neutral, a given, and eventually will not be enough. The only solution is to make the willful decision to be content with what we already have. Am I selling out, giving up, or being less competitive? Heavens no, but I am reintroducing balance and sensibility back into my life, and it’s exhilarating, better than a new Porsche! In retrospect, my grandparents and even my parents, all reasonably affluent and definite achievers, practiced enjoying what they had. I used to think that they missed much, but now I realize that they didn’t. They bought quality, saved, donated, were well read and educated, traveled, and played, but not at the break-neck pace that I and many of my baby-boomer compatriots have.

Life is so abundant is many ways. We choose and attract into our lives that which we think about. Maybe the answer for me is tempered between the scarcity that some of my earlier family lived with to today’s realization that life is rich, wonderful, and here for our exploration and growth – a mixture of giving, receiving, and caring, but never thoughtless taking. Yes, I do aspire for more and better, but now in a more measured way, and not simply for myself. Anyway, it is our choice; one each of us can make every single moment. Enjoy your present and savor its abundance. You may find something even more precious as did I. I found something in that week that seemingly many others don’t possess – “enough.” My race was over, but my journey continues. Gone is the nearly frantic pace to succeed. Perhaps now I may work to transition from whatever success I had to that of significance and giving. The lessons of my “homeless experience” really caused me to discover that home lives within me surrounded by a wondrous sense of abundance!

Two days later on the Friday after Thanksgiving, clean-shaven and well clad, I revisited San Francisco for a day of shopping. I did not go alone, but enjoyed the company of my lady friend. There were more than few familiar faces that didn’t recognize me, and I observed some very familiar patches of pavement as I recounted to her what I had just experienced. San Francisco will never be the same for me; I am different now, grown a little. I purchased nothing that day, which was fine, perhaps even exhilarating.  Thanksgiving was sweet and it was the best of Christmas’ too. And now every day is Thanksgiving.

Did I also find that God Force or Source Energy? Just perhaps I did. It’s in all of us, whether or not we have a home. If you look for it, the wonderfulness is all around us. Treasure the life you presently have. God bless.

Epilogue, November, 2010.

Bob Fagan today.

It is a decade to the day that I returned home from my San Francisco street experience. Interestingly enough, the weather this week has been nearly identical to what I faced those five days and nights – record below freezing temperatures in the high 20s intermixed with rains as the arctic storms buffet Northern California.

I continue to live by myself in the same home I did ten years ago, but no one, most of all me, could have predicted how the next decade would transpire for me in both good and unintended ways. Had I possessed a crystal ball, I most assuredly would have taken pause if not been downright frightened. The details are unimportant, but as I look back, I wouldn’t change anything.

In addition to the lessons I related in the story, in the many times I’ve retold the story I have always emphasized that I could be stripped of all my worldly possessions, and left with only my health, time, and friends and I’d still be a very wealthy man. Earlier this year, I amended that. Though I don’t intend to manifest this, you could also take my health and time, but leave me with my friends and I’d continue to be a very wealthy man. I am not trying to sell you or anyone else on that. Rather I only encourage you to be open to the change and possibilities that your journey offers you, and not be addicted to what you currently believe to be your truth. “While your head and ego may often lie to you, your heart never will” is but one of many lessons I’ve since learned.

November, 2011.

For me, I have realized that the answers to my life’s dilemmas and questions are found within as Jesus, Buddha, and the other great philosophers have offered. And reflecting back on all those people I watched while living on the street, I realize that for all our differences, we are all connected sharing more commonalities than differences. No one is better or worse than others, but each of us are the products of different experiences and perspectives. We view life and existence from our own unique lens of experience. Maybe in another dozen years I will have an entirely different perspective.

I now agree with what they say about “what doesn’t kill you makes you stronger.” I can now look back on that crazy idea of living without for a few days and realize that it was indeed a gift.

November, 2013.

I now am transitioning my belief that we are all, indeed, “connected,” and love or pure energy connects and fear disconnects us. When we focus upon our differences, we become fearful and nothing truly revolutionary, creative, or sustaining can ever come from fear. When we judge others, we take ourselves away from our best or highest selves and into a hellish fear. Though they may not appear as such, all of our journeys are perfect – perfect for our own lessons and impacting others simultaneously. Trust and focus upon love works far better than trying to avoid fear. And my journey continues…

December, 2015.

The way I now relate to the world is far different than it was 15-20 years ago. I am pained to witness the hate, fear, and judgment that is highlighted and spirited on by the media, the elected elite, and the fearful, but even more delighted to see still more others shifting toward peace, love, forgiveness, compassion, and service. History has told us time and again that violence and killing don’t create lasting peace. Hate and anger don’t dissipate hate and anger. The competition/scarcity model is sorely obsolete and the creation model with collaboration, communication, and cooperation lies ahead. The fixes to our opportunities may not be instant enough, but the shift has begun and better things are ahead, especially when we truly realize that every thought and action does affect or contribute one way or another to this spaceship called Earth that we’re all traveling on.

December, 2018.

There is enough deceit to go around and I continue to be dismayed with the general lack of leadership and integrity in our large institutions fed by greed and controlled by fear. The media continues to feed us fear at a non-stop pace because it’s profitable, but don’t allow this outside noise to infect you. Research all points of view, most importantly those opposite of yours before you opine. Think for yourself. Righteousness, judgement, hate, jealousy, and anger are all cousins of fear and if you are like me, you are better to eliminate them from your diet. I continually remind myself to notice and appreciate all the good about us – and it’s there in so many forms. Our personal improvement is more important than ever. Don’t bury your head in the sand, but instead take daily positive actions no matter their size to improve yourself and serve others. Every act of love counts. Our survival in a very real way depends upon our kindness to one another. What is heartening to me is the growing amount of love, compassion, and consciousness I witness first-hand growing around me. Besides, life is so difficult, how can we be anything but kind? Lets you and I be an important part of that!

December, 2020

It’s a stretch to believe that it’s now been two full decades since my adventure. We are so quick to label things and especially other people. I find this so superficial, inaccurate, and dehumanizing. (I commit to doing less of this myself.) With Covid-19 ruining any sense of normalcy for hopefully the time being, my comments of 2013 return to me. We are all connected and no act of kindness, consideration, or courtesy is too small. I’ve never taken my own or anyone’s health for granted so the pandemic forges nothing new there. Life can change or end in an instant. With the gift of aging during this 20-year period, I’ve lost about one hundred friends, acquaintances, and associates apart from this pandemic. My own mortality becomes increasingly scarce and fragile – it’s autumn and the colorful leaves have begun to drop revealing human frailties common to all fortunate enough to make it this long. It reminds me that each moment is precious and it is never too late to finish strong. As a country, a species, and, of course, for me the individual, we have much improvement and growth opportunities ahead.

December, 2021

It’s been a year of much quiet reflection and I continue to be amazed at the abundance we enjoy in America. No, call it over-abundance. Now, many of the poor in America literally live better than royalty did just a few centuries ago. Most others have it far better. We enjoy the options of instant entertainment, so much stuff that hundreds of millions of storage units at more than 50,000 U.S. facilities are stuffed to capacity, over-consuming food, drink, worthless information, and polluting noise. We have so many options, we can barely manage. My grandparents never had it so good or easy! Phones that have incredible capabilities, and our government that has in short order made better health an option for most all with the distribution of the Covid-19 vaccinations — a pretty amazing logistical feat.

I learned last evening that one simple Google search consumes about the same energy as an incandescent bulb burning for several days. Wow! Yet, no one seems happier; many are quietly frightened. Women’s rights are being attacked, but not weapons and violence. Police reform languishes as do voting rights. Hyper-individualism is championed at the expense of our common growth and even survival as a species. Our diets are being subsidized to encourage obesity and all the side effects unhealthy metabolism brings making any decent healthcare system virtually unsustainable. Democracy is being attacked while the separation of church and state is blurred. So many seem oblivious to how connected we and the the planet are. American statesmen are rapidly disappearing and replaced by greedy, selfish tribalists intent only on keeping their power. On the other hand, I also witness an awakening in many where giving, sustainability, and more conscious awareness balances a growing sense of entitlement by others. We still enjoy wonderful opportunities. I realize that not only you, but I am either part of the problem or part of the solution, but never not one of them. Be the change you wish to see. I will.

August, 2022

At the time of this adventure, I was ascending in my career. At the age of 50, given my resume and trajectory, I reasonably could have easily expected a good fifteen more years of prosperity when those similar to me are awarded with their greatest responsibility and income. It wasn’t to be. At the time on the streets of San Francisco, if you had passed me, you might have felt sorry for me or more fortunate than me. The truth is that appearances can be deceiving; as you know, I was fine. That said, the next 7-8 years were extremely challenging for me. With the exception of a few successful interim executive stints, I mostly lived below the “U.S. Poverty Level” albeit in one of the country’s most expensive areas. Annually earning less than my HOA condo fees and rewarded only for brawn or for doing the most menial clerical tasks, the time was indeed a challenge. If you had seen me then, you might again mistake my challenges that were disguised by my cheerful, positive demeanor. I was living on fumes and when traveling for writing assignments, my resulting income wouldn’t even match my airport parking fees. Trying to practice abundance, I was nonetheless reintroduced to scarcity, coveting any gift, giveaway, or asset. The point is that none of us are immune to pain and you can’t tell it from someone’s appearance, conduct, or social media posts. This would later again be emphasized in my coaching where I realized that some of my uber-successful clients lived lives of quiet desperation.

After spending well into five figures attempting to market myself for jobs, I realized that I had to reinvent myself – to discover other ways of serving and adding value, and grow my skillset. This transition began slowly with failures and disappointments, but falling forward, I began to realize that my messages had value. During this time, my gratitude never dipped and taking small steps, the progress soon became measurable and then large. I was “The Law of Attraction in action” taking massive inspired action, practicing as best I could “loving awareness,” and feeling what I was seeking. For all the things I lacked during this “down time,” I now have in abundance. You can appreciate that I take none of this for granted. If I can do this from some very discouraging points, you can too. How might you proceed? What might you change? What action might you take? When?

Is yours one of a growth mindset or are you stalled in a fixed position? Consider that a growth mindset is one of the foundations of excellence, growth, and ultimately fulfillment. Are you curious and if so, how is it evident?

And should you want to change the course of your life, pay attention to your thoughts and beliefs. Honestly examine which ones might not be working for you. We always have choice, and should you choose to reframe or change a non-working belief or story, your life can pivot in an instant. I also realize that perhaps I needed that difficult period in my life. It shattered any expectations I may have had and provided me the fuel for growth that otherwise I might never have experienced if I had had continued prosperity.

Though you and I may not always appreciate it, during this “street adventure” or when I now quiet myself and see more clearly, I realize, “We have so much in common, and life is good!”

December, 2023

At this time, I am reminded that violence does not create sustainable peace, darkness does not make light, and hate and fear won’t foster love and trust. I am perplexed that a significant portion of the American electorate as well as those in several other countries don’t demand or support integrity in their elected officials, allow fascism to grow, and are satisfied watching others practice greed and power-grabbing while taking away hard-earned freedoms. By their own actions, it has exposed those previously thought to be honorable people to be otherwise, consumed by personal ambition. I am similarly perplexed how so many think that it’s Christian to be an anti-Semite or anti-Muslim. I find it ironic how a political party that for so long championed individual rights and fiscal responsibility created legislation that produced record deficits, eroded the middle class, and is attempting at every opportunity to impose a national religion and tell women even under the most dire circumstances what they can and can’t do with their bodies. It’s quite the turnaround and perhaps the biggest turnaround disappointment of my lifetime!

On the other hand, I am heartened by the realization that the vast majority of human beings live in harmony though those damaged outliers attract the most attention. We can and must do better starting with everyone of us. Today, more die prematurely from overeating than from violence. Personally, I appreciate more than ever the importance to one’s life in having purpose and healthy relationships along with the ability to experience “experience.” And what an absolute joy it is to keep on learning, growing, and expanding. That keeps me younger and more alive than otherwise. May you be blessed and pay it forward!




3 Responses to “Street Smarts – San Francisco Bay Area Exec’s Lessons As A Homeless “Street Person””

  1. Carlos Silva

    Thank you for sharing. In my opinion, life’s biggest challenge is to find oneself and spirituality no matter our status or ethnicity.

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