7 Life Lessons from Cycling Across Africa

I expected the 12,000km journey from Cairo to Cape Town to be a challenge; I didn’t expect to find the keys to leading more fulfilling life.

It’s hard to believe that nine years ago, I was cycling in the desert of Egypt, still doubting how I would ever make it all the way to Cape Town. Every day of the four month journey across Africa presented new challenges, adventures, and lessons (like: aren’t most challenges in hindsight just adventures?).

Nearly a quarter of the forty riders who set out from Cairo didn’t make it to Cape Town due to a severe accident or illness. Another quarter made it, but suffered a broken wrist, rib, or collar bone along the way. The other half of us who were lucky enough to avoid such physical damage still endured our own share of challenges — gastrointestinal illness, malaria, thefts, rock assaults, flat tires, you name it. Thankfully the scorpions and hyenas and elephants that we encountered kept their distance.

Cycling an average of 125km (or ~80 miles) per day, over all imaginable terrains and in all imaginable conditions, redefined suffering and relief for me. It’s hard to imagine feeling as hungry, hot, sore, tired, bored, or terrified again. Which, in hindsight of course, was the entire point.

On a daily basis, I would reach what appeared to be yet another physical or mental limit. Then — out of sheer necessity — I would manage push right past it, until my concept of ‘limits’ dissolved entirely. I found that beyond my imagined physical and mental limits lay my practically unlimited potential and a kaleidoscope of emotions.

Until I reached the top of the Blue Nile Gorge, our most grueling and relentless day of uphill cycling, I didn’t realize that satisfaction wasn’t exactly the same feeling as happiness. I’d lived my whole life believing words like joy, equanimity, and wonder were virtually synonymous with happiness, not different states of being entirely. When I paused at a viewpoint in Namibia, exactly 10,001 kilometers into our tour, my eyes traced the cobblestone road which lay ahead as it wound down the hill and stretched out into the horizon without a single other being in sight, I had the thought “ahh, so this is serenity.” Upon seeing my first giraffe, “awe.” Cycling on dirt roads during a downpour in Kenya, “exhilaration.”

Fear too started to take on different shades: worry that I might not have enough water on me to get to the next rest stop in the Sudanese desert was distinct from the nervousness I felt approaching groups of drinking men reaching out for me from the side of the road on Saturdays in Ethiopia which in turn was distinct from the anxiety I felt after consuming edibles on the beach of Lake Malawi.

I must have experienced the whole range and depth of human emotions over the course of this transformative tour, but nothing compared to the sense of security that unfurled in me when Table Mountain appeared on the horizon and all the trials and tribulations of the past 120 days suddenly made sense.

I’ve compiled the seven main lessons I learned over these four months here. They have helped me gracefully weather four years of a presidency that threatened to disrupt world order and what feels like four years of a global pandemic that did, and have guided me through subsequent breakups, deaths, moves and career transitions. I hope they will help others do the same.


When I look at the photos of myself from the first day of the tour, I am reminded that despite my wide smile as I pose with my bike in brand new gear in front of the Great Pyramids of Giza, I felt a palpable and pervasive terror in anticipation of what lay ahead.

Where would I go to the bathroom? How would I survive nights in the desert when the temperature fell below freezing while alone in my tent? What if my tent leaked when it rained? What if I get saddle sores? What if I get sick? What if I get a flat tire and no one is around to help me? What if I run out of water? toilet paper? Sunscreen? Food? What if I get lost? What if my phone dies? Or worse, breaks? The what ifs were endless.

And then I started encountering the very scenarios I had been dreading. Shortly after lunch, near the beginning of a 60+ kilometer stretch of gravel road in Ethiopia’s highlands, I noticed my odometer had stopped working. I panicked and immediately took out my phone to study the picture I took of the day’s directions which had been scribbled on a whiteboard:

STAGE 22, 126KM

0KM: back to main gravel road, turn L

23KM: R after village

40KM: coke stop

65KM: lunch

92KM: R at dirt road

120KM: R at bottom of hill

126KM: camp

Our directions for the day almost always used kilometers as the main guidepost. I strained to remember the more detailed directions given by the Tour Director the prior evening while we sat around eating dinner. I couldn’t remember her sharing any landmarks that would help guide me when I was supposed to make the right turn at a dirt road, let alone which hill bottom turn would take me to camp. Every road in this hilly country so far was made of dirt. I didn’t take notes because I assumed I could rely on my odometer.

Turns were usually also marked with orange flagging tape, tied to the nearest pole when one was available. But the frenzied chaos of the Ethopian villages that dotted the road every few kilometers of this road meant that looking out for orange tape tied that *might* be tied around a pole every inch of the journey was impractical. Not to mention the fact that sometimes locals took the tape. I didn’t have a SIM card in my iPhone, which I kept on airplane mode anyway and only used it for photos and music since power outlets were few and far between, and I needed to stretch my last battery charge for several more days.

The one thing I could rely on, as someone who was always dozens of kilometers behind the peleton, was that locals would definitely remember any riders who passed before me. Including the direction they went. This might have seemed like an obvious and easy answer — to just ask for directions — but on top of the language barriers, I have always hated — not just *hated* but felt incapable of — asking for help.

As I approached the next village that afternoon, my heart started racing. I didn’t want to bother anyone. And I didn’t trust they would be willing to help me once I did. I’m ashamed to admit I even wondered if they would take advantage of me, knowing I was somewhat lost. I reluctantly made eye contact with the first group of locals I saw, and pointed down the road with a quizzical look on my face. At once, the young men and women enthusiastically and confidently raised their arms and nodded while pointing me down the road I was on to continue my journey behind the other riders. I breathed my first sigh of relief. That wasn’t *so* bad.

In every village thereafter, with somewhat less apprehension, I asked for help until finally a group didn’t point in the same direction but waved their arms in a different direction, guiding my turn at what I *hoped* was the 92km mark. Sure enough in the village that followed this turn, locals smiled and motioned for me to continue down the road I was on. I could only assume this meant that I was on the same road as the other strange, albeit faster, faranjis. By the time I reached camp that evening, I felt no apprehension at all. I had survived, and it turned out I could rely on others to help me. And help me they did, every time I cycled alone, the rest of the way down the continent.

Not only that, other scenarios from my nightmares continued to prove I could trust and rely on strangers. I ran out of water in the middle of the hottest day of my life, in the sparsely populated Sudanese Saharan desert. I still describe the day as the closest to death I think I will ever feel until the day I die.

Just when I thought I couldn’t possibly go any further, a few huts blessedly appeared on the sandy horizon. I pointed my wheel in their direction, closed my eyes, and put every ounce of energy I had left in me into the pedal strokes needed to get me to safety. At the first hut, I dropped my bike, breaking the mirror affixed to my handlebar, and stumbled with blurry vision and shaky legs up the first step of what turned out to be a store — with refrigeration no less! — where the shopkeeper was waiting, or so it seemed, for me. I didn’t have any cash on me, but without hesitation, the man handed me a cold soda. It was the most delicious Sprite ever consumed in the entire history of time. I waited in front of the shop until another rider passed so I could borrow money to repay him. He refused the payment anyway.

The temperatures dropped below zero while I slept. But I survived. My camera broke. I got sick. My butt never stopped hurting. I survived, I survived, I survived.

The mountains were bigger, roads rougher, and days longer than anything I had experienced before. As the challenges stacked up, I started to trust more and more that I would survive whatever the day could throw at me. Not only that, I felt at total peace with the idea that I might not, because at least I was living. Everything felt as it should be, and I could take each challenge as it was presented to me. One day at a time, without worrying about what might happen.

In hindsight, the hardest days of the tour ended up being the best because these were the days I grew the most. In confronting all the emotions I instinctively wanted to hide from, I found my power, an inner-calm, and a deeper sense of connectedness.

I went from being afraid of anything and everything, including asking for help, to seldomly feeling intimidated or scared. I gained a deep confidence in myself that I can do hard, terrifying things. And because I believe this for myself, I believe it is possible for anyone. I mean this from the bottom of my heart: there is nothing special about me, or extraordinary about what I did. Anyone can do it.

You can do hard things too. I can promise you that anything that feels challenging in the moment will feel surprisingly manageable in hindsight. With enough time, whatever you are struggling with, even if it’s as awful as the death or illness of a loved one, will in the long-run make you a stronger, better version of yourself.

So I encourage you to test your perceived limits, to challenge your biggest fears, and to trust that you will not just come out physically alive, but that you will also feel more alive than ever before.


Some days, smells, views, and feelings from the Tour d’Afrique are seared in my memory. Among these are the couple days which shifted my whole way of thinking.

By the time we reached the highlands of Ethiopia, we were almost a month into the tour and I was rather used to the challenge of cycling off-road, in extreme heat, up steep hills, and over long distances. So when I saw the directions for the day that took us into Bahir Dar, my heart jumped with joy. The ride promised to be an easy 60 km cruise, mostly downhill, on an entirely paved road into town. We wouldn’t even need to plan for lunch on the road that day because it was to be such a short day.

And yet, I was exhausted as I rolled past the finish line. The day felt exactly as difficult as all the days that preceded it. How could it be that 60 kilometers felt as tiring as 120?

I thought it was funny, but didn’t give it a second thought until a couple weeks later in Kenya when our finish line was unexpectedly pushed back a couple kilometers, so we would have more comfortable ground to pitch our tents on. Two additional kilometers after cycling over one hundred shouldn’t make too big of a difference right? Wrong! Every one of those extra inches I had to cycle were the most gruesome and excruciating of the tour.

There is nothing worse than thinking you’re done with a challenging day and realizing you’re not.

I realized after the longest day on the tour, 210km with headwinds in Botswana, and the day with the most climbing (2000m in Ethiopia) — which both felt bearable — that we really can do anything we set our minds to.

Our experience is entirely determined by our expectations.

Looking forward to an adventure? You’ll surely enjoy the ride. Hoping for a smooth day without any interruptions or setbacks? You’ll surely be disappointed.

This lesson shows up for me over and over again. At work, when I expect the unexpected — staff turnover, cancelled contracts, delays, new competitors — my days are much more enjoyable than when I try to force things that are out of my control to unfold according to a plan that is convenient for me. I knew in the first days of the pandemic that it was better to mentally brace myself for a year of sheltering at home than the initial two weeks that most people were anchoring on.

I think this also plays out interpersonally, especially in education and dating. Students rise to the expectations that teachers set for them. If you expect someone to treat you well, or give them the benefit of the doubt, most people will surprise you.


After the first day of the tour, as I lay down on my sleeping pad in my tent, I wanted to cry. It was the furthest I had ever cycled, at 134km, and I didn’t think I had it in me to complete the next day’s 166km. 100 miles in the desert. My body was already screaming with pain. I was jet lagged. I was so uncomfortable sleeping on the ground. And my ego was bruised. I was among the slowest of the 40 riders. Even the women in their 60s were much faster than I was at 25. It was embarrassing. So much mental and physical anguish and I was only 134km out of 12,000. The road ahead felt insurmountable.

But I’d backed myself into a corner — everyone who knew me was expecting me to finish, so I knew I at least had to give it a better shot. Sometimes backing yourself into a corner with huge commitments is the best thing you can do for yourself.

I told myself “if you can bike one mile, you can bike ten. If you can bike ten miles, you can bike twenty.” Before you know it, twenty miles becomes thirty, forty, a hundred. I just needed to focus on one mile at a time. Baby steps.

By the second night, I was still having a terrible sleep, and my butt hurt so bad I could hardly tolerate sitting down to eat. But I had an epiphany. Yesterday I was 1/120th of the way through the tour, but today I was 1/60th, and tomorrow I would be 1/40th, and the following day 1/30th. These baby steps sure added up fast.

With every day that passed, I realized I didn’t have to do something huge to have meaning, I just had to start. Once I took the first step, I just had to take the next. By the time I made it to Cape Town, 12,000km later, I could see that by far the hardest part of the tour was actually just deciding to do it. Taking that very first step.

I have so many big goals in life — whether finishing a book or a documentary. Whatever they are, I have learned to think about just taking the first small step — telling others about my goals, writing one sentence, posting one photo, researching equipment, etc. — and seeing where that leads me. Then I take the next step.


When I signed up for the Tour d’Afrique, I was looking for a BIG challenge. I had just come home from the 2010 Winter Olympics in Vancouver and was feeling extremely inspired. But at 24, I thought it was unrealistic to start trying to become an Olympian. The only other BIG challenge I could think of was climbing Mount Everest, but I hated being cold, so that was out. I googled “epic bike tour,” the next idea that came to mind, and this was the first result.

This was it. It was exactly what I didn’t know I was looking for. From that day on, I obsessed about it quietly. I mentioned it to my mom, who was terminally ill, and her response was “not while I’m alive!” I’ll wait until you die then, I thought. I think she thought I was joking, and her reaction made me think maybe it was too crazy. I was scared to tell anyone else about my dream. But I still couldn’t stop thinking about it. So, when my mom passed away, I signed up.

You know you should do something when you literally can’t get it out of your head until you do.

As soon as the tour started however, I realized it was nothing like I expected: it was less about the sum of the days — reaching the grand finish line — than about making the most of each individual day.

I couldn’t have imagined all the beautiful people and places I would encounter along the way. I expected to see the Pyramids in Egypt, camels in Sudan, highlands in Ethiopia, zebras in Kenya, Mount Kilimanjaro in Tanzania, the beaches of Lake Malawi in Malawi, Victoria Falls in Zambia, elephants in Botswana, sand dunes in Namibia, and Table Mountain in South Africa. I did not expect to help a girl with her application to Harvard while I was in Sudan, or be shown around an Ethiopian town by a brilliant boy with whom I am still in touch, nor did I expect to pass through fields of butterflies in Kenya, or develop a full-blown donut addiction in Namibia.

What a shame it would have been for me to rush to the finish line and neglect to stop and smell the flowers.

As the Tour d’Afrique is technically the world’s longest bike race, there were a few riders who raced the entire way. My 10 hour days took them 3 hours to complete. They stopped for no photos. They met no locals. What a shame, the rest of us thought, to come all the way to this beautiful continent just to stare at the few inches of road in front of you.

I signed up for the tour with the finish line as my trophy, but what I won through the friendships built and small moments along the way were so much more precious than I could have imagined. I wish I told my mom before she died that I actually was going to do it. She understood better than anyone that the joy is always more in the journey than in the reaching finish line.


Preparing for four months of bike touring in Africa was daunting to say the least.

I agonized over which tent and sleeping bag and pad to get. Which bike and tires and bike shoes and helmet and accessories. Which water bottle and replacement parts and rain gear. The options — and trade offs — were endless. In addition to the weight and space limits to what we could bring, I was on a tight budget. Most of all, I feared that one misjudgment of what I might need, which wouldn’t have mattered over a short distance or in North America, would surely compound into a disaster of epic proportions on the rough, remote roads and campsites of Africa.

Then I got to Africa and realized I had made so many “bad” decisions. Everyone seemed to know that Schwalbe Marathon tires were the best, but I had only bought the “Durango” tires. They also had blow up mattresses to sleep on that looked way more comfortable and took up less space than the stupid folding pad I brought. I instantly regretted not getting laser eye surgery, and not investing in a better saddle bag.

But almost as soon as the cycling started, a rider’s bike shoes were stolen. My odometer broke. Thorns penetrated even the indestructible Marathon tires. My water bottle flew off my bike and rolled down a cliff when I hit a giant pothole. Another rider’s tent poles snapped in the high desert winds. Someone got so sick she soiled her sleeping bag. Someone else lost his camera.

And guess what, we all survived. We adapted. We moved slower than expected. We got creative. We embraced the art of letting go.

The more I lost, the more I realized how little I needed. The more that broke, the more I appreciated that which didn’t. The dirtier I got, the more I could accept that mud is just mud. The more obstacles I hit, the more I realized that slow is not a lesser speed to move in life.

It’s incredible what we can adjust to if we try. My body would wake me up in the middle of the night to eat two energy bars to satisfy my caloric needs. The appropriate nerves in my bum went numb. I even got used to going to the bathroom with a curious and watchful audience.

We all got blisters and saddle sores and regretted some of our purchases, but this is just where things got interesting. We bonded over losing feeling in our fingers and the futility of our rain gear. Had we run away from the slightest discomforts, as most our cultures train us to do, we wouldn’t have gazed at the starriest of skies while eating the juiciest of mangos in the best of company.

Lessons 6 & 7 were lengthier, so I created separate posts — read more here.

Brooklyn based Start-Up Advisor, Impact Investor, Filmmaker, Writer, and Leadership Coach. I focus my time on the future of learning and the future of work.