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Win­ning Through Uncer­tain­ty: Lessons In Over­com­ing Adver­si­ty with Gratitude
Jeff Kirshman Apr 30, 2026
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Sam Good­win spoke in a keynote address at SAP Con­nect Day Chica­go on April 22026.

Sam Good­win would like to invite you into his prison cell.

It is 8 feet by 8 feet, buried deep beneath the city of Dam­as­cus, with no win­dow and no sense of time. The air is stale. The floor is con­crete. In one cor­ner sits what pass­es for a toi­let. In the oth­er, only dark­ness. Noth­ing to read. Noth­ing to watch. Noth­ing to do but think.

I’d like you to do your best to smell the stench of that imag­i­nary small hole,” Good­win told a ball­room audi­ence in Chica­go ear­li­er this month, paus­ing long enough to let the visu­al set­tle. I’d like you to imag­ine being stuck for months, 7,000 miles away from the good life.”

It was an arrest­ing way to address a room full of busi­ness lead­ers. But Good­win, speak­ing at SAP Con­nect Day Chica­go on April 4, was not inter­est­ed in eas­ing into his sub­ject. The best­selling author and founder of SGI Ven­tures used his sto­ry to pull the con­ver­sa­tion out of abstrac­tion and anchor it in some­thing real.

The Uncer­tain­ty of the Situation 

On the sur­face, Goodwin’s path to that moment had been unlike­ly. A sea­soned trav­el­er with a goal of vis­it­ing every coun­try in the world, he had spent years mov­ing through places often described as off-lim­its, find­ing that the real­i­ty on the ground was often warmer than it was portrayed.

Vis­it­ing Syr­ia in the spring of 2019, that pat­tern changed. Short­ly after land­ing, Good­win was tak­en off the street, blind­fold­ed, moved through a series of loca­tions, and even­tu­al­ly placed in a mil­i­tary prison after being accused of being a spy. He would remain in iso­la­tion for 27 days.

The days passed with­out mark­ers. He could hear oth­er pris­on­ers in near­by cells, at times being tor­tured, but he remained com­plete­ly alone. He had no reli­able infor­ma­tion about his sit­u­a­tion or whether it would change. His life had nev­er been more uncertain.

What fol­lowed, as Good­win described it, was not a sud­den shift so much as a grad­ual recal­i­bra­tion. Stripped of move­ment, infor­ma­tion, and con­trol, he began to test what remained with­in reach.

Good­win began with some­thing sim­ple enough to feel almost insuf­fi­cient. Grat­i­tude, in its most basic form, became a way of inter­rupt­ing the instinct to spi­ral. There was air to breathe. There was food, how­ev­er min­i­mal. There were moments when the sit­u­a­tion did not get worse.

These things may sound ele­men­tary or insignif­i­cant,” Good­win said, but I found that each one of these small expres­sions of grat­i­tude became this silent rebel­lion against the uncer­tain­ty of the situation.”

The exer­cise was about cre­at­ing dis­tance from the instinct to cat­a­stro­phize. Over time, those small acknowl­edg­ments accu­mu­lat­ed into some­thing stead­ier — a way of ori­ent­ing him­self when noth­ing else could.

From there, his atten­tion nar­rowed to con­trol, or the small por­tion of it that still exist­ed. Good­win could not influ­ence his release or change how he was per­ceived. He could not alter the con­di­tions of the cell. But he could decide how to respond to the thoughts that sur­faced in that environment.

My goal wasn’t to get rid of neg­a­tive thoughts and feel­ings,” Good­win said. That would be unre­al­is­tic. My goal was to change the way I respond­ed to them.”

Not Only Some­thing To Sur­vive, But Some­thing That Might Shape Him In A Use­ful Way”

That dis­tinc­tion, between elim­i­nat­ing uncer­tain­ty and man­ag­ing a response to it, intro­duced a form of struc­ture into a sit­u­a­tion that offered none. Move­ment, even in the form of pac­ing a few steps at a time, became inten­tion­al. So did the effort to notice when his think­ing drift­ed and to redi­rect it. These were small acts, but they cre­at­ed momen­tum, a sense that not every­thing had been ceded.

Over time, some­thing else began to shift. The con­di­tions did not improve, but his rela­tion­ship to them did. The rep­e­ti­tion of those days, the absence of dis­trac­tion, cre­at­ed space for a dif­fer­ent per­spec­tive to take hold. Good­win began to see a gap between what uncer­tain­ty felt like and what was actu­al­ly hap­pen­ing. The feel­ing was expan­sive, over­whelm­ing. The real­i­ty, while still severe, was more contained.

That dis­tinc­tion became a turn­ing point. If the feel­ing could be sep­a­rat­ed from the facts, then it could also be man­aged. It was in that space that the expe­ri­ence began to take on a dif­fer­ent meaning.

Being tak­en hostage was as insane of a sit­u­a­tion as I could have ever imag­ined being in,” Good­win said. But I began to real­ize and believe that if I could main­tain hope, per­se­vere through this, and sur­vive, I would then be bet­ter equipped to take on more chal­lenges in my life going forward.”

It was around then that he began to con­sid­er the expe­ri­ence not only as some­thing to sur­vive, but as some­thing that might shape him in a use­ful way. If he could endure it, Good­win rea­soned, he might come out of it bet­ter equipped to han­dle what­ev­er fol­lowed. The idea did not reduce the dif­fi­cul­ty of the moment, but reframed it. The cell became, in a lim­it­ed sense, a place where some­thing was being built.

Good­win was even­tu­al­ly moved out of soli­tary con­fine­ment to anoth­er prison in Adra, where he spent addi­tion­al time with oth­er detainees, form­ing rela­tion­ships and shar­ing lan­guage. His release came through an unlike­ly chain of con­nec­tions that reached from his fam­i­ly to inter­me­di­aries in the region. When he was dri­ven across the Lebanese bor­der and reunit­ed with his par­ents in Beirut, the expe­ri­ence that had defined those weeks began to recede into some­thing he could exam­ine at a distance.

Lat­er that year, despite his family’s objec­tions, he board­ed a flight to Brazil, com­plet­ing his goal of vis­it­ing all 193 countries.

Act­ing with Con­fi­dence Today to Lead with Vision Tomorrow

Telling his sto­ry in Chica­go, the sto­ry func­tioned less as a nar­ra­tive end­point than as a frame­work for think­ing about a dif­fer­ent kind of uncer­tain­ty — the kind that defines much of mod­ern work. The conference’s through­line of act­ing with con­fi­dence today to lead with vision tomor­row depends on the abil­i­ty to oper­ate with­out com­plete infor­ma­tion, to make deci­sions in con­di­tions that do not set­tle into clarity.

Goodwin’s argu­ment is that the skills required to do that are not abstract. Rather, they are prac­ticed, often in small, repeat­able ways. Per­spec­tive, estab­lished through some­thing like grat­i­tude, cre­ates a base­line. Con­trol, even when lim­it­ed, cre­ates move­ment. And uncer­tain­ty, when reframed, becomes a space where some­thing use­ful can take shape.

We can’t always choose the exact path that we take in life,” Good­win said. But we can always choose the man­ner in which we walk it.”

The phras­ing is famil­iar, but in the con­text he described, it lands dif­fer­ent­ly. Four steps for­ward, four steps back, pac­ing in a room with no exits. The con­di­tions remain fixed. The response does not.

For an audi­ence of busi­ness lead­ers and prac­ti­tion­ers, the trans­la­tion was direct. Uncer­tain­ty is not episod­ic. It is con­stant, built into mar­kets, tech­nolo­gies, and the pace of change itself. The ques­tion is not how to elim­i­nate it, but how to func­tion with­in it with­out being defined by it.

As Good­win closed his remarks, he turned to a con­cept that has shaped how he under­stands his own expe­ri­ence: post-trau­mat­ic growth, or PTG. If post-trau­mat­ic stress cap­tures the last­ing weight of hard­ship, PTG sug­gests anoth­er pos­si­bil­i­ty, that those same expe­ri­ences can also pro­duce strength, clar­i­ty, and a deep­er sense of purpose.

The idea is not that adver­si­ty is desir­able or that it should be min­i­mized. It is that it can be used.

We could be held hostage by any­thing: alco­hol, drugs, ill­ness, rela­tion­ships, finances, injuries,” he said. But the way that we embrace and man­age those chal­lenges, the actions we take, I think that defines who we become — and from where we begin again.”

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