REEP Challenge: How to Gamify the Art of Living

Total Reading Time: 14 minutes.

I’m not going to lie to you. I’ve struggled a lot with working while traveling. Over the years I have devoured a tremendous amount of education on productivity and effectiveness and experimented with many of these various solutions.

There’s always that moment in the taxi or Uber/Lyft where the drivers asks…

“So are you traveling for business or pleasure?”

“Umm…well, you know. It’s always kinda a bit of both!”

The idealistic world of blending business and pleasure is 100% possible. I’ve done it on many occasions. Nevertheless, this blending can be the cause of much frustration, FOMO, and angst.

So how does one flow through life? How do we value presence over productivity (as the amazing Maria Popova beautifully describes) rather than hustling until our limbs fall off? How do we accomplish big goals and leave a lasting contribution for humanity, while still cultivating a sense of awe (as my friend Jason Silva masterfully captures in his videos), gratitude, and “living in a beautiful state” as Tony Robbins describes?

The art of living - flowing through life.
Flowing through life. (Image: Amsterdamized)

Years ago, a friend sent me a quote saying that it would resonate strongly since this is what I also try to embody in my life:

The master in the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his information and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence at whatever he does, leaving others to decide whether he is working or playing. To him he’s always doing both. – James Michener

It’s a beautiful description of a sometimes elusive space many of us want to live in…

Now let me be clear — it is much easier to live in this space when we’re settled into routine. But avoiding routine is often why we chose this lifestyle in the first place. You’re likely an adventurous “wonder junkie” like me and seek awe-inspiring moments in your own unique way.

When it becomes difficult to cultivate this is while we travel. We’re pulled completely out of the ordinary and our senses are electrified. We’re kids in a candy store with insatiable hunger and this conflicts with our need to be responsible about certain things, mainly around work and making money.

Some solve this by achieving financial freedom through modeling the wealthy, but most of us aren’t there yet. In order to feel good while we travel we need to check off a few boxes each day. If we do this we can live in that elusive space. Growing up, my father, my first and favorite teacher, would always tell me…

“Arman, you’ll regret playing now if you haven’t done your homework yet. You’ll spend your whole time playing worrying about what you need to do. If you just spend 30 minutes now doing your work you can be completely free and present while you play.”

I think perhaps a similar philosophy needs to be implemented in adulthood. So how do we maintain the same level of effectiveness in our work while traveling?

My refusal to give up on a sustainable solution landed me on a method that could work for just about anyone, even me, the “I need to maximize this experience and still get all my work done” person. The solution is the REEP challenge.

Types of Self-Directed People: Solopreneurs, Entrepreneurs, and More

Before I dig into the REEP challenge, let’s speak to the different types of self-directed people this applies to and could be helpful for…

The Vacationer

This is everyday Josephine. She has a more traditional career and doesn’t necessarily want to have a full workday while she travels. Things like exercise, maintaining diet/nutrition, and working on personal projects are still important to her.

This could also be everyday Jeffrey. He’s an entrepreneur and business owner but more of a traditionalist when it comes to travel, in that it’s meant to be a vacation. Perhaps he’s traveling with his family, or he intends to use the trip as an opportunity to completely disconnect, rest, and rejuvenate. Health, fitness, and personal growth are still important to him.

The Full-time Digital Nomad

These are your modern day full-time vagabonds. Digital nomads often station themselves into a new city for weeks, months, even years. As travel lovers, a digital nomad will still feel the urge to experience the new culture and will struggle with who to balance work and play. Our game below will help them stay focused and create a daily ritual that rewards both.

These are people like Natalie Sisson, who run successful online businesses and call themselves Suitcase Entrepreneurs. Natalie clearly has an insatiable thirst for travel, and having to run a six-figure plus business as she does this is no easy task.

Dan Andrews and Ian Schoen of TropicalMBA are pioneers of the digital nomad world, and have gathered a large community in Southeast Asia. After personally having spent 97 days traveling throughout the region, I know how great the lifestyle can be. This means distractions, and the REEP challenge will help remedy that.

Colin Wright, a writer and entrepreneur who moves to a new city for three months at a time, is famous for traveling light. Colin has in a way gamified his travels by involving his community of readers to vote on his next destination.

The Location-Independent Solopreneur

Our next travel lover may have a home base, but they often pack up and move to new destinations at a moment’s notice. This solopreneur prides themselves on being an independent minimalist.

Minimalism is not a lack of something. It’s simply the perfect amount of something. — Nicholas Burroughs

Sean Ogle spent the first six months of his entrepreneurial career living abroad in Thailand and Vietnam. After years of living a conventional disillusioned lifestyle, he was fired from his job (that he hated), and made the move. Today, Sean is married and loves his homebase in Portland, Oregon, but he continues to travel at a moment’s notice and truly embodies a location-independent lifestyle.  

Josh and Jill Stanton from Screw the 9 to 5 wanted to test out what it would be like to build a business together. They started a small affiliate website working endless caffeinated nights and eventually built up their business to making over $10,000 a month…how cool is that?

The Solopreneur Consumed by Wanderlust

Many solopreneurs, entrepreneurs, and even freelancers enjoy having a home base. Yet, they’re often consumed by wanderlust and crave the adventure of life on the road.

A famous example of this is NYT #1 bestselling author and entrepreneur Chris Guillebeau. Chris went on a quest to travel to every country in the world by the age of 35 — and he did it. Oh, then he wrote a book about it

Another example is…me! Yes, yours truly, Arman Assadi. One of my core motivations for living a self-directed life is a strong desire to see the world and experience every culture. To me, it’s education that keeps my mind nimble and aware of cognitive biases. But I live in San Francisco and am lucky enough to have a modern apartment I don’t want to give up.

No matter how much I travel, I love the feeling of coming home to my “old familiar pillow”.

No one realizes how beautiful it is to travel until he comes home and rests his head on his old, familiar pillow. – Lin Yutang

The Traveling Entrepreneur or Businessperson

Pat Flynn runs his online business built around passive income, which allows him to spend more time with his family. Between traveling around to different cities to speak at conferences and running a major brand, productivity on the go is essential. His business enables him to plan his day around his life and family, not around his business.

Chris Ducker began blogging in 2010 to document his journey of becoming a Virtual CEO. Not only did he achieve that goal, he launched another business in the midst of it all called Virtual Staff Finder, which I’ve used multiple times to hire virtual assistants. He then wrote a bestselling book called Virtual Freedom (4.9 stars on Amazon!), and continues to run multiple business, speak around the world, travel to conferences, and maintain a life at home with his family.

Gary Vaynerchuck, the author of multiple NYT bestselling books and host of the #AskGaryVee Show,  is best known for loving the hustle. When it comes to keeping up rituals and staying productive while traveling, Gary is someone to watch. Rather than allow the environment to take control, Gary is proactive rather than reactive and utilizes a lot of the principles you’ll learn about below.

The Lifestyle Entrepreneur

Lewis Howes is a rock star lifestyle entrepreneur. As a New York Times bestselling author and host of The School of Greatness, Lewis spends much of his time building his brand and inspiring people to achieve greatness around the world. At the same time, Lewis also greatly values his freedom and ability to travel as a lifestyle entrepreneur.

I’ve spoken to Lewis about this before and it’s clear he values his home base in Los Angeles, but he also loves the flexibility to travel at any time. If you watch Lewis on his Snapchat (username: Lewis_Howes), you’ll see exactly how he does it. One example — no matter what, he makes sure to get some form of exercise (one of the keys points in REEP) in each day, regardless of where he is in the world. Lewis plays the same game below, he’s just set up his own incentives and rules for it.

The REEP Challenge

The solution is this: we turn the entire event into a game.

Sometimes turning difficult tasks or the formation of building new habits and rituals into games can be very effective. And in this case, I’ve found the game that I’ve developed below — inspired by The Grand Travel Experiment from ZenHabits’s Leo Babauta — highly effective.

The four areas our game focuses on are:

  1. Rituals – morning routine
  2. Eating – nutrition
  3. Exercise – health
  4. Performance – business

On Rituals

When traveling, it’s incredibly easy (and painful) to forget your morning ritual. For each of us, this is the one thing or series of activities we do each morning that puts us in a good mood/state and prepares us to rock the day. Carefully crafting your ritual is an important and fun activity I discuss in detail here.

On Eating

It’s natural to want to consume the local food, but this often leads to daily cheat meals that you legitimize with self-told lies, “this is the only time I’ll ever get to try pizza in Napoli!”.

Maybe partly true, but problematic. Bad nutrition puts your body in an instant coma, and often leads to digestion issues, which means no work for you. It’s also a lot easier to get sick and your energy levels will decrease. This is the last thing you want when you’re traveling.

On Exercise

Back home you might have a regular gym you visit, or perhaps you regularly play a sport or do things like Soul Cycle and Crossfit. When you’re traveling or living abroad, it’s hard to keep up any exercise routine. But getting the blood flowing is imperative, and one way or another it’s possible if you make it a priority.

The REEP challenge will help. If you’re feeling down, sluggish, and low on energy — you can often trace it back to a lack of exercise or proper nutrition. A University of Georgia study proves thisBuzzfeed compiled a list of exercises that you can perform pretty much anywhere. 

Think of these first three areas as the foundation to your productivity while traveling.

Tip from Arman: Use this travel opportunity to learn more about the culture you’re in by investigating how people exercise there and do it with them. For example, you can join a Muay Thai in Thailand and get the workout of your life. Plus you’ll get really good at kicking people in the face, which you’ll hopefully never need to do. My friend Nick took a trip to Thailand for a month just to experience this. 

On Performance

Our goal here is balance. We want to have fun, experience life, see attractions, and create new memories. We do this by being very strict with our work schedule.

Your normal workday is 8–10 hours back home. You’re likely working on high value tasks less than 50% of the time. This is where constraints come in, which help you focus on the most important tasks only.

Constraints work very well for any type of work, especially that of a creative nature. Writers like James Clear often use constraints to create the work rather than wait for it. James is someone who understands that creativity isn’t happenstance inspiration, it requires diligence and the use of intentional constraints. 

If you have a home base, you likely also have a dedicated workstation setup, and if you’re like me you even have a standing desk and large monitor you’ve gotten used to. None of this is possible when traveling, so it’s important to dedicate time and simply do the work, as one of my favorite authors Stephen Pressfield talks about in his book

REEP Details & Rules of the Game

  1. Perform your morning/daily rituals, eat healthy nutritious food that gives you energy, exercise, and do the most important tasks in your work every day.
  2. For each category you’ll receive a certain amount of points each day — I’ve broken down the point structure below
  3. Track your actions either as you go or review your day before bed during your evening ritual
  4. To score big points perform the top action in each category, e.g., complete your entire morning ritual rather than just one piece of it
  5. Add up your points each day and measure your progress
  6. Celebrate the fact that you played the game and remember that progress equals happiness

What gets measured improves. Tracking these actions and playing the game is not only fun and addictive, but it’s what will lead to improved habits and results and the impact of that will be seen across all the areas of your life.

Rituals Actions

  • 5 points for completing your entire morning or daily ritual.
  • 3 points for completing the most important aspect of your daily rituals, e.g., meditation.
  • 0 points for not completing.

Eating Actions

  • 5 points for eating a healthy meal according to your nutrition standards and stopping when satisfied, not full.
  • 3 points for eating a healthy meal, but overeating.
  • 2 points for eating a cheat meal and stopping when satisfied.
  • 0 points for a cheat meal and overeating.

Note: Maximum of 15 total points from this category, based on a maximum of 3 counted meals per day.

Exercise Actions

  • 5 points for completing your chosen workout, e.g., push-ups and yoga, jump rope and a jog, sit-ups and air squats, etc. Keep it simple.
  • 2 points for staying active throughout the day, e.g. walk everywhere within a 30 minute radius, run up/down stairs (always choose the stairs over elevator), play with your kids, chase a dog, etc.
  • 0 points for no exercise

Performance Actions

  • 5 points for working 3 or more hours at 75%+ productivity — this means you focused at least 80% of your time on actual work (you can measure this with a free desktop app called RescueTime)
  • 3 points for working 3 or more hours
  • 2 points for working 2 or more hours
  • 2 points (bonus) for completing your highest value task 
  • 0 points for working less than 2 hours or not working

Note: Yes, the 2 bonus points for completing your highest value task can be combined with other point categories within work for a maximum total of 7 points.

Daily Point Totals

28+ – Preeminent Traveling Rock Star
17+ – Elite Globetrotter
5+ – Average Vagabond Hobby Artist
0–5 – A Tourist on Vacation


Gamifying an experience like mastering the art of living is a fun way to improve our rituals. If we are what we repeatedly do as Aristotle said, should we not focus the majority of our time and attention on mastering these habits? Instead of allowing our environment to dictate our lives and habits, we can proactively examine why we do what we do and implement better actions.

The REEP challenge is a fun and effective way for anyone who’s self-directing their life to get results starting today. Try the experiment out and measure your progress, and get ready to see tremendous growth and experience a sense of fulfillment. This idea is what gets me through my travels and I’ve even implemented a version of it in my daily life when at home.

I’ve shared this experiment with many of my successful entrepreneur friends, and they all love it. I believe this is because providing a structure and framework to our habits makes it easier for our minds to know exactly what we need to do each day to continue growing and making progress. If progress equal happiness people are going to experience a tangible uplift in their mood, not to mention their actual results and successes.

Note: If you really dig the experiment and find it useful, let me know. I’m considering expanding on the topic and creating additional tools and resources to make tracking and rewarding yourself easy.

Photo credit: Balancing actCC license

The Kilimanjaro Chronicles: Escaping Bandits, Upgraded Porridge, and a Deathly Blizzard

Total Reading Time: 20 minutes.

Day 0 – En route to Arusha, Tanzania from Nairobi, Kenya.

It was 2 AM. We were sitting at a roadside “bar” on the border of Kenya and Tanzania. We’d spent the day in Nairobi, and were already enthralled by our environment. The city had awoken every sense, and it was already beginning to feel like a vivid, lucid dream.
The visa office was just a few steps down the road. We stumbled in and looked around. Old posters on the walls, a few electronics, paper binders to keep track of the transactions. It took us 15 minutes to find someone, but we finally found him sleeping behind the counter on the floor. Yellow Fever vaccines were “required”, but I’m pretty sure we could have handed over a yellow paper and it would have been the same.
The crisp Kilimanjaro beer, which we all savored, kept our minds occupied and bodies relaxed as we waited out the Kenyan bandits. Or were they raiders? Not sure what the right nomenclature is here. We were on our way through to Tanzania when our driver (and part-time bodyguard), Robert, noticed a flashlight beam into our car.
He slowed down until the car stopped, and pulled down his window on the passenger side. The men were actually local police. They spoke a few words back and forth. Robert turned around and said, “There are men hiding in the bush ahead. If we continue forward, they will rob us in the dark. If we wait until 4 AM we will be fine. Do you want to continue?”
How considerate of Robert to give us the option. “Holy shit. This is real!” I said, as I looked at my fellow mountaineering comrades. “I wish I still had my knife now,” I thought. “Yes Robert, let’s wait. And we can wait until sunrise if that’s better.”
“No, 4 AM will be fine.” So we turned around and headed toward the side road to the local hangout. Robert kept a watchful eye on us at all times. If we wanted to use the toilet, he’d escort us himself. We sat and drank our beer with the locals, making sure to maintain a “we’ve done this before” look about us. We surprised Robert by wanting to sit and hang out with the locals. He was likely more amused than surprised.
There was a small TV, no more than 18 inches wide, hanging in the corner playing African music videos. On the street side there was a makeshift charcoal barbecue. A young man was cooking up the remaining scraps of meat from the evening.
The locals were welcoming and we never once felt threatened. Robert seemed to know something we didn’t though, and eyed his surroundings. We sat at a table with plastic chairs and continued to sip our beers, waiting out the bandits. “Did we just avoid a robbery, or was this about to be a kidnapping? I wonder how much my ransom would be…” I thought. Either way, it was a relief to have avoided it all.
It was unanimous. The boys agreed, Kilimanjaro beer was delicious. The irony put a smile on my face. The tallest freestanding mountain in the world was still ahead of us.
There’s traveling, and then there’s Africa. So the adventure begins…

Day 1 – Mount Kilimanjaro

“I just threw up…”
Our fearless leader and birthday boy, Nick, woke up on day one of the hike looking like he needed an exorcism to rid the Kilimanjaro demons tormenting his insides. His face flush and emotionless—food poisoning had taken over.
Nevertheless, after months of anticipation it was time to begin our seven-day hike up the tallest freestanding mountain in the world. That first night we met our guide at the Outpost Lodge, a young Tanzanian man of Maasai descent named Babalou.
Babalou is the quintessential guide. He’s friendly, experienced (having climbed Kilimanjaro over 480 times), and a pure alpha male. He explained all the logistics and prepared us with the first day’s schedule. There would be 16 porters carrying food and supplies up the mountain. Two specialists. One cook. Two assistant guides. And Babalou.
We boarded the bus and were immediately met with big smiles. “Jambo!” said each new face. Babalou introduced some of the main players. They all had nicknames. Like Babu, our assistant guide. Baby is a 58-year-old man with a calm, quiet voice that implores you to lean in and hear every word. “Hakuna matata, my friends”, he’d often say, which is Swahili for “no worries”. We were surprised to hear the famous phrase from Lion King wasn’t just for tourists. Hakuna matata symbolizes life in East Africa, the way “Pura Vida” does in Costa Rica.
There were a handful of things we knew about the hike: prepare for the cold, drink lots of water, walk slowly, and be ready for a difficult summit night. Day 1 was a long 16 km hike through the first layer of the mountain—a beautiful rain-forest. We even spotted some blue monkeys along the way. Playful little fella’s…
We walked and walked. By the end of the first day, exhaustion had set in. I looked around to see the boys were in similar spirits. Nick never once complained, but looked like death. “Our bodies are just in shock” I thought. It’ll get easier.
At camp, we began integrating into life on the mountain. Hygiene and cleanliness? Non-existent. Comfort? Not an option. This meant embracing our core masculinity, which is a sexy way of saying we were filthy animals who barely remembered to brush our teeth for the next 7 days.
Like, really filthy. Blowing your nose with your own hands and wiping on a shirt you’d wear for days in a row were commonplace. At the end of day 1, the cook’s assistant—a young, hard-working, quiet Tanzanian named Benja—prepared us “water for wash”. This was a bowl of warm water left by our tent to wash our face, hands, and feet with. Being the amateurs that we were, we all passed on this that first day. This was a mistake we wouldn’t make again.

Kilimanjaro Arman Assadi 2015
Long hair, don’t care.

Dinner. My expectation for food on the mountain was porridge. And maybe something to dip in it. Our cook, Shakur, fed us breakfast, lunch, and dinner until our stomachs burst. The first dinner was exceptional. Always at least three courses, and always something new and creative. Presentation was key, another surprise.
We needed the calories, this was one of Babalou’s orders. Benja would serve the food and continue to fill our plates until it was all gone. Babalou always entered the mess tent as we were finishing dinner to see how we were feeling and chat about the next day’s schedule.
This would often go something like, “okay guys, for tomorrow you will need about 3-4 liters of water. We leave here by 8 AM. It’s an easy hike (this was his reverse psychology game), and we will be at the next camp in 6-8 hours. When you get there you will have some tea’s or coffee’s or Milo or hot chocolate. Then you have water for wash at 4:30 and you rest until dinner time.”

Snacks are key.
Snacks are key.

We began to expect Babalou to tell us exactly what we needed to do at every moment. And we began to enjoy this. Our minds were so occupied with the hike that Babalou’s instructions made life easier. Throughout the day he’d check on us and look at our faces. I think he was checking for symptoms from the altitude.
Sleep came easy that night. After dinner it was off to the tents. Myself, Daniel, and Jason in one. Nick and Amit in the other. After a quick change of clothes we got into our bags mummy-style. I threw on my headphones, started a new audiobookStephen King’s On Writing (my new favorite book about writing)—and within seconds it was off to dreamland…

Day 2 and 3 – Mount Kilimanjaro

“Oy! Oy!” It was Benja with his signature wake up call, promptly outside the tent at 6:30 AM.
Mornings were simple. Benja would zip the tent open and be holding a tray of cups with tea, coffee, or hot chocolate. We’d usually have this right in the tent while we were still warm and cozy. I went with the tea.
Outside the early morning air was fresh and the sun was crisp. “Water for wash” sat outside the tent. After a quick brush of our teeth (if we remembered), we’d head to the mess tent for breakfast, which again, was spot on thanks to Shakur, our all-star cook. Babalou came in and reviewed the day’s agenda, always with a smile. “How are you feeling guys? Super duper?! Okay guys, today we will be climbing some big rock and it will maybe will be hot so bring your sunny creams and sunny hats.”
With us, Babalou was always friendly and approachable. With his team, the same. He treated them as equals, but also demanded excellence. I admired him for this and enjoyed watching him in his craft. But like I said, he demanded excellence. When something wasn’t the way he wanted it, you’d hear that person’s name being called out with authority to fix the issue ASAP. As he often said, “your smile is our job guys”. He did whatever it took to make that happen.
After breakfast it was back to the tent to change into the day’s gear. In the lower parts of the mountain this usually consisted of a base layer, mid layer thermal, sun hat, and rain jacket in the day bag. Day 2 was my favorite hike. It was a difficult one with lots of big boulders and rocks, but this kept us engaged. The landscape was spectacular. At times we were barely clinging onto sharp rock walls and hopping from one boulder to the next, which felt more like mountaineering than hiking.
At the end of Day 2 we all felt better. While the day’s hike was still difficult, we’d began to get in the flow and our bodies started adjusting. The post-hike decompression of Day 2 was memorable. Our afternoon rest in the tents was accompanied by the soothing sound of rain splashing on the tent. It was the perfect complement to being bundled up in the sleeping bag. After sunset, temperatures dropped drastically and we’d need to wear multiple layers and a jacket to stay warm.
Day 3, we conquered Lava Rock. Again, this involved a lot of boulders and rocks, but it was even more treacherous than before. One small slip and you’d go tumbling down. The porters did it with ease, jumping from boulder to small rocks with 15-20 kg on their shoulders. We decided Babalou was actually part-gazelle. He’d often get bored and opt for a more difficult route just to spice things up.

Rocks of Kilimanjaro.

At this point we were approaching higher elevations and could definitely feel the altitude. It was important to pace our hiking, “pole pole” our guides would say. One quick move and you’d be catching your breathe for the next 20 minutes. No joke—the air was thin.
I’ll never forget the diverse landscapes we discovered each day. Maybe it was the altitude, but I started to imagine we were on a space expedition—each day’s terrain was like a new planet. It was like we were living out our own Interstellar journey. The scenery was that distinct and outrageous.
Did I mention the porters? Not only would they hike with all the gear, but they’d beat us to camp and have everything set up by the time we’d get there.
We’d heard that Day 3 was often the most difficult, other than summit night, and it didn’t disappoint. At this point we were all dealing with a variety of issues, outside of looking and feeling like filthy, I mean masculine, men. Sore legs, headaches, and in particular, Jason had picked up a virus in his throat/chest and was on his way toward an infection.
Babalou ensured we were following his instructions at every moment. Lots of water, “pole pole”, eat a lot, sleep a lot. I wondered if there were any “local remedies” for the altitude, and mentioned this to Babalou. He swiftly obliged and returned later with a little present.
The key, as Babalou would say daily, was “positive mind”. We never once allowed ourselves to think about not reaching the top. Sure, the journey is more important than the destination and all that, but we didn’t go to Africa just to walk around a mountain like tourists for a few days.
The summit was the goal—and it was in sight.
Slowly but surely, we were making our way up the mountain…

Day 4 and 5 – Mt. Kilimanjaro – Above The Clouds.

I woke up at 5:00 AM to meditate. In the mountains, darkness takes on a new meaning. Without liquor stores and street lamps to illuminate the sky, it’s just you and the galaxies above. I threw on a few layers, grabbed my headlamp, and walked until I found a big, cozy looking rock to sit on.
The mountain has magical effects on the mind. It forces you to give up your everyday needs (which you’ll discover are unnecessary luxuries) and find solace in uncomfortable situations is a powerful exercise. My mind was at peace. The aimless chatter in the skull relaxed in this new environment.
As I opened my eyes, I watched the sun rise, but like never before. I sat there on my rock, above the clouds. I’ll save you the hyperbolic adjectives about its beauty, and instead tell you this: it was the type of moment you’d wish for in a heaven. Which ironically enough, is available to us right here on earth.

Kilimanjaro Arman Assadi above the clouds
Above the clouds.

After chef Shakur’s breakfast, the morning got even better. Our guides and porters put on an impromptu a cappella concert, and began singing the three songs we’ll never forget: Jambo, Yo Mama, and Kilimanjaro.
My personal favorite was “Yo Mama”. As you can imagine, this put wide, unshakable grins on our faces and prepared us for the final days before the summit. Day 4 brought some of the best views and scenery imaginable. We were frequently above the clouds with blue sky’s. Mount Meru, another massive nearby peak, stared at us from miles away.
Day 5 was just as mesmerizing, but the chatter in the skull soon returned. It was the final hike before our big summit, and our attention shifted to the big night ahead. We had a shorter hike that day, only four hours. The plan was to arrive at camp. Eat. Rest. Eat again. Then try to sleep from 6 PM – 10 PM. At 10:30 PM it would be prime time.
I didn’t sleep a minute. Whether it was nerves or the altitude that caused my restlessness, I couldn’t do it. I lay there for hours, with nothing to do but wait.
This would mean I’d have to pull an all-nighter for the summit. 7-8 hours to the top, hang at the summit for 5-10 minutes, 2-3 hours back down to camp, rest one hour, then 3 more hours to the lower camp…
“In the mountains there are only two grades: You can either do it, or you can’t.” – Rusty Baille

Day 5 and 6 – The Summit of Mount Kilimanjaro

You know that classic war movie scene when the bomb siren goes off and the soldiers jolt out of bed like killing machines ready for battle? That was us. The moment we heard Benja say “oy!” at 10:30 PM from outside the tent, we sparked up, ready to climb.
Now instead of pulling out an assault weapon from under our pillow, it was a headlamp. With extra batteries, of course. Our battle boots sat right at the foot of the tent. 2-3 layers of socks on already. Outside it was around 5 °F (-15 °C). The higher we went, the colder and windier it’d get. Babalou—our amiable, gazelle-like guide—had performed a gear check earlier that day. Our objective was to put on layers ‘till we resembled the Michelin man.
We met for a quick final snack and tea/coffee in the mess tent. Babalou came in, more serious than ever before. This concerned me a little. You could tell shit was about to get real. He’d casually mention later that in September he had to evacuate four different hikers during their summit attempt back down the mountain. Altitude is no joke. At almost 20,000 feet high there is a risk of death.
“Guys, it is time. Listen—I want to see you all at the top. But don’t worry, from here on I have 97% success rate (he really said this). You won’t need much water tonight, only one liter. We won’t be taking any break, only short one for 1-2 minutes because it is too cold guys. We will try to stay together as one group, but we will split up if it is necessary.”
And so it began. The 5 of us boys, plus 3 guides and one porter who’d been given a privileged nod to join for the summit. Man, was it cold. The sky was pitch black and beautifully decorated with giant, lit up stars. The only thing you could see were these stars, your own two feet, and the heels of the person ahead of you. As one single file, we began to make our way up.
Is that a snow flake? My face formed a smile. We’d all talked about how perfect it would be if there was snow at the summit, a rare phenomenon during the dry season. “Beautiful. But maybe I’ll zip up this jacket a little higher”, I thought. As we walked, the flake soon morphed into an onslaught of sideways blowing wind and snow. The wind began to howl. It was a full on blizzard.
Not only would this be the longest hike of our seven days, but it was the steepest. We’d also be gaining the most elevation in one hike—from around 15,000 feet up to almost 20,000 in one night. Because of this, we had to take it slow. It was imperative. As the night went on, it felt more like a trudge than a walk. “Pole pole”, step-by-step, up the mountain we go.
The freezing temperatures and fierce winds left everything in sight frozen. Around the halfway mark, Nick noticed something out-of-place. It was a plaque, sitting on a big rock. We dusted off the snow and read the name of a young climber, a young man fallen too soon. He had died right there. I left my good thoughts with the man, while the thought of dying on the mountain left chills up my spine. Just a couple of weeks earlier a fellow blogger, Scott Dinsmore, had died while summiting Kilimanjaro. While it was an unfortunate, freak accident that took his life (a falling boulder), it was even more real and close to home.
I took a sip of water. I had to blow air back into my CamelBak hose to remove the water, otherwise it would freeze. Summit night brought the real mental and physical test. When you could see through the snow, you’d catch a glimpse of each of us struggling to take the next step. It required maximum effort to continuing stepping and stay calm. With each step came a deep inhale and exhale, then another step. Our big goal was to reach Stella Point as a team. From there, it would be only one hour to the summit as we’d walk around the crater.
By the 4th hour, my altitude headache had gone from an annoyance to an excruciating, nauseating migraine. Some of the crew came close to vomiting. Every 30-60 minutes we would pause to pop a “Gu”, a liquid energy supplement, which was the only thing we could stomach. I couldn’t tell if I was famished or full, my body was sending all sorts of signals but I couldn’t distinguish between each one. Babalou checked our faces for signs of life. The key was to let the body know what time it was. It was a time to fight. Not flight.
The first glimmer of light, both literally and metaphorically, began to illuminate our path just as we reached Stella Point. We finally saw the beautiful mountain we had been climbing the past seven hours. It was a spectacular view, and we couldn’t help but celebrate. All of us made it to the final checkpoint as a team. This was a huge accomplishment. However, apparently, a lot of climbers take the victory too far and fail during the last hour to the summit. We were at 18,652 feet (5,685 m). Staying here too long was dangerous. We took it slow, and began taking photos of the view quickly so our hands wouldn’t freeze up.
“Woah. Did you see how blue his lips were?” We were passing climbers walking the opposite direction that had already made it to the summit, along with others who were still trudging there like us. They looked like death. Bloodshot eyes, pale, veiny skin, blue lips, and emotionless faces. How or why some of them continued was beyond us…
We were finally approaching the summit. “Wow, we’re actually all going to make it!”, I thought. We were lucky to have no big groups behind us. We did it. We made it to the “roof of Africa”—19,341 ft (5,895 meters)—the peak of the tallest freestanding mountain in the world. We spent an entire 10 minutes at the top taking photos. We even mustered the energy for an “olé, olé olé olé!” chant as one. I grabbed my pipe (a new hobby) from bag and took my summit photo. “Piece of cake”, I said to Babalou with a laugh.

Summit. Somehow found the energy to bust out my pipe.
Summit. Somehow found the energy to bust out my pipe.

I was mostly speechless. I imagined I’d have a lot of thoughts, but the last eight hours had taken its toll. My head was pounding, but I smiled. I couldn’t get rid of that smile. As we made our way down, I began to think about why people do crazy things and test their limits.
I was reminded of “The Iceman”, Wim Hof, who says it’s in the moments where we have no control and comfort that we can exercise our ability to just be okay. No matter what the external circumstances are, we can be okay. It’s a way to know you do have control. There is a power in this knowledge, and it isn’t only for the thrill-seekers. At least, that’s how it seemed as I walked down the mountain.
As I mulled over these scattered thoughts, I found the next few hours of descent even harder than the climb up, as odd as that sounds. My left knee began to collapse and could hold no weight. An old MCL issue was creeping up, and there was nothing I could do, so I grabbed a hiking pole and turned the limp into a pimp walk and kept going. As we went lower, the headache exchanged with the knee pain, but I was thankful to be done with the altitude sickness.
We made it down to camp and passed through the blizzard into a more stable climate. We were soaked. We were given just one hour to rest, and then we’d continue moving down to a lower camp. All our gear and clothes, including base layers for some of us, was drenched. We fell on our mats like wet logs and passed out for 30 minutes. After what felt like seconds, we put our damp clothes back on and made our way down for another few hours.
By the end of Day 6, we had hiked 18.5 hours in two days. For me, this was done on zero sleep. Tomorrow would be the final day on Mount Kilimanjaro. We did it, all of us.
That night, I slept like a dormant volcano…

Day 7 – Final day on Mt. Kilimanjaro

It was time to celebrate.
We woke up in the morning and had only a few hours left to reach the gate and board the bus back to the outpost lodge. We were almost done, but first, that mornings celebrations.
The ritual is to present the porters and guides their tip on this final day. We piled our cash together and handed Babalou a slip with the amounts for each person. Babalou lined up the whole team and began reading out loud how much each person had earned. Later, Babu AKA baby face, our older assistant guide, pulled us aside. “I feel like I’m flying. Wow. I can’t believe it. Everyone will be celebrating with their families tonight!”
Next, we put much of our gear together and donated it to the porters. I felt really great about this because many of the porters had basic supplies and gear. In some ways it could be more valuable than the cash, which would likely go to their families.
It was finally time to party. The whole team began to sing and dance to out three theme songs. One porter in particular was my favorite, his enthusiasm for life would shine through in these moments as he’d bust out his moves for the songs. He couldn’t hold back his wide smile.
Babalou, being the orchestrator he is, got the whole team to sing happy birthday to Nick —another special moment. Once we made it down, we climbed into the bus to head back home. We stopped at a local store and grabbed some beers for everyone.
As Babalou presented us with our official certificates, we sipped on Kilimanjaro beer and sang along like we’d known Swahili our whole lives…
“Jambo! Wooo! Jambo wana!…


I think we peeled back this layer of invisible bullshit our normal reality has imprinted on us. It was like leaving the machine for a bit and being realizing you can be OK without conventional luxuries. We thought we were free and self-directed, but in some ways we’re still taking a traditional path.
We still have empty goals that we think will make us happy “some day”. We still have this complicated formula for how we think we’ll eventually be free, be happy. But don’t we already have all that? Do we actually need those things to take that big victorious sigh of relief and just feel good?
On the mountain, all that’s gone. You find a way to just be content. And it makes you realize…what if we don’t need to escape to feel that every day? What if we can live with a simple gratitude regardless of external events and circumstances? I like that idea, and that’s what I’ve brought back with me.

We made it through the blizzard to the top.
We made it through the blizzard to the top.

If you’re interested in learning more about Mount Kilimanjaro, check out this awesome infographic below…

Kilimanjaro Infographic

10 Must Have Apps for the Travel Lover

Total Reading Time: 5 minutes.
It was the late Summer of 2013 and I had just finished traveling all throughout Southeast Asia for 97 days. This was my first experience with traveling while working, and many lessons were learned. The most difficult aspect of these nomadic 3+ months was not knowing who or what to trust when it came to: accommodations, transportation, and general information.
Whether you have to occasionally travel for work, or are a location-independent entrepreneur, full-time vagabond, digital nomad, or travel junkie—there are a handful of apps and services that are critical to your survival. The issue is knowing which ones.
As we already know—there is an app for just about everything—although we’re still waiting on the one that prints greenbacks. Every day a new app company launches looking to earn the trust of the travel community.
Since my initial overseas voyage, I’ve been averaging around one trip every two weeks. Sometimes these travels are domestic, while other times they’re international. At this point, I’ve tested enough services and apps to know what is essential, and what is superfluous.
In this guide I’ll outline the best and top must-have apps for the frequent (or occasional) traveler. I’ll also include sign-up links, and where available, I’ll include codes to discounts and bonuses for signing up.

Travel Accommodations

1. Airbnb

Airbnb travel app
It’s only fitting that this is the first app listed, because it’s also my favorite. Airbnb is indispensable. I’ve used this incredible service all around the world to find beautiful homes, beach bungalows, modern apartments, and even private rooms. And I’ve also been a host, so I know and trust them inside and out.
If you don’t already know about this app, you’re in for a treat.
Use this link to sign up now and get $25 toward your travel.

2. Hotel Tonight

hotel tonight travel app
If you like to travel last minute like me (or just happen to need a place to stay ASAP), Hotel Tonight is your new best friend. This wonderfully designed app gives you incredible deals at hotels worldwide. The app now also allows you to book in advance, not just the same day.
You can download the app here and use my promo code AASSADI3 to get $25 off your first booking.

3. app
Similar to Hotel Tonight, this app from is essential for travelers and lets you book both in advance and get access to last minute deals. What I like most about this app is the abundance of choice. While Hotel Tonight hand picks just several deals for each day, provides access to a wider variety.
You can download the app here.

4. Hostelworld

Hostelworld travel app
Hostels can be a fantastic way to meet other travelers, and a great way to get to know a city. There are some incredible hostels in various parts of the world, and Hostelworld has been my go-to app for this. While there are other competitors in this space, this app has been my favorite.
You can download the app here.

5. Couchsurfing

Couchsurfing is first and foremost a community. If you’re on a low budget and still want to travel the world, or simply enjoy meeting interesting people, Couchsurfing will be your new favorite travel app/service.
I’m often asked if this is safe and trustworthy. Close friends have used the service to travel the world for free and made lifelong friends. Plus, there are verifications and a review system.
You can check out the service here.


6. Lyft and Uber

The two big giants of ride-sharing, Lyft and Uber, are essential for travel. The days of traditional car rentals are long gone, and the on-demand economy is here to serve our every need. Want a car to pick you up from anywhere in minutes? You need these two apps.
As the first ever official Lyft user/passenger (yes, seriously, and I still have no plaque for this cough) I tend to favor Lyft when I can. I also find that the drivers are more sociable, and the experience is similar to getting a ride from a friend of a friend.
The app you use depends on your style and its availability, so give both a try if you can. Lyft is currently only in the U.S., but expanding globally. Here’s a full list of cities.
You can download the app here and you’ll also receive $20 in Lyft credit towards your first ride.
Uber is available in 58 countries. Not cities. I used Uber all throughout Rome, Italy during a recent trip for cheaper than a taxi. Here’s a full list of cities. I find Uber to be professional and fast.
You can download the app here and even claim a free ride worth up to $20.

7. Getaround and Turo (formerly RelayRides)

While Uber and Lyft are great for on-demand rides, sometimes you’ll want to rent a car for a few hours, or even days. Why not borrow someone’s car for a fraction of the price? That’s where car-sharing comes in. No membership fees, and a wide variety of cars available on-demand.
Tesla anyone? I no longer use traditional rental car services, thanks to the two apps below.
Turo is fully available in cities throughout the U.S. Here’s a full list of cities.
Getaround is currently available in the San Francisco Bay Area, San Diego, Austin, Portland and Chicago. Sign up for the service here, and you’ll also receive $25 of driving credit.

8. Zipcar

Car sharing is great, but the service is still expanding. If you need a car and want it done quickly, Zipcar is the way to go. They do have a membership fee, but what I love most about Zipcar is its wide availability in most cities throughout the U.S., Canada, and even some in Europe. Here’s a full list of cities.
You can sign up here and download the app, plus receive a $25 bonus toward your account.

Travel Information

9. TripAdvisor

tripadvisor travel app
This app does it all and can be used all around the world in even the most remote cities/countries. Find reviews for just about anything, get a list of top things to do, plan and book your trip, check flights, download maps for offline use, and much more.
You can download the app here.

10. TripIt

tripit travel app
This all-in-one travel app stores your entire itinerary and all pertinent information in an easy to use interface. Stop sifting through your email to find your flight number or hotel’s address—TripIt can handle it for you.
You can download the app here.

Information & Resources

11. Fancy Hands

With all these apps you may start to get overwhelmed with the planning and researching side of things. Did I mention I don’t actually do any of it myself?
I use a virtual assistant service called Fancy Hands that handles it all.
When most people hear personal assistant they think, “I can’t afford that!” Well, it’s not expensive to get started, they’re only $29.99 a month. And you can also get 50% off your first month with this link—so only $14.99 to start. Do it.
Here’s my complete review on Fancy Hands along with best practices and tips for getting started.

12. Snapchat

snapcode Arman Assadi
This is my Snapcode! Just point your Snapchat camera at this image to add me.

Not a travel app you say? I beg to differ. No wanderlust-driven excursion is complete without the best social media app available right now. What better way to connect with your family, friends, followers, and share stories in the moment?
I’ll be exhibit A. Just click here to add me or point your Snapchat camera at the image above to add me on the Snap and get ready for a mix of off-the-dome philosophical rants, random voice impressions, and adventures around the world.

Photo credit: Lost AdelaideCC license

How to Live a Location Independent Freedom Lifestyle

If you could be anywhere in the world right now, where would you be?
Those that live a location independent lifestyle can truly be anywhere, at anytime. Some of them even do it full-time.
A big reason I left my job at Google (and the “job” world in general) was because no matter how hard I tried I couldn’t escape the feeling of being locked down. When you work for someone else, you’re obligated to be where they want you to be. There are very few exceptions, and most are temporary.
In America, we’re only given a standard issue two weeks of vacation time per year. Having a love for travel and experiencing life in different parts of the world does not work well with this policy.
So what are you supposed to do?
Watch the short video below to learn more.

Living a Location Independent Lifestyle

This is a snippet of my life, how it actually is. I didn’t film this on the beach and try to sell you on some cheesy dream (although that might have have looked cooler). All I’m exposing is freedom.
Solopreneurs, entrepreneurs, and digital nomads all around the world are living this way right now. Many of them have created niche online businesses that support the lifestyle of their choice. And others have even evolved far beyond that, devoting themselves to contributing on a grand scale, and still having the flexibility that a location independent lifestyle provides.
Most of these people are not traditional entrepreneurs, these are modern-day solopreneurs. People using the skills they already have to build a product, offer a service, and launch small online businesses. Solopreneurs are people who are finding the intersection between what the world needs, what they love, and what they already know.
With a location independent lifestyle, you can be anywhere in the world. You can build a business around your lifestyle, not the other way around. Many solopreneurs travel a lot. Others just like the flexibility and idea of being able to work from a cafe, a friend’s house, or home.
If you’re like me, you enjoy having a home base, but you love being able to travel, mix work with play, and explore different parts of the world for no reason at all.
Life should be fulfilling, in every way. We shouldn’t have to work to live and trade our time for our freedom.
Make the decision today to begin building a Freedom Lifestyle. Decide once and for all and don’t look back. The only thing you’ll regret is not trying.

Photo link: Mural in RioCC license

How and What to Pack for Your Next Travel Adventure

Ah…packing. The unpleasant, lingering step-sister of traveling.
In this short video you’ll learn how and what to pack for your next travel adventure. During this particular trip, I’ll also be working from abroad. You’ll get an overview of all the tools and equipment I recommend you carry if you’ll be doing the same.
For the traveling solopreneur and digital nomad, it’s all about balancing work and play. You don’t want to feel guilty about exploring, but you also want to stay productive. I had to mess up a few times to learn the lessons. The first time it really hit me was when I made this video in Southeast Asia.
Having the right tools and packing correctly is a big part of it. Whether you’re on vacation, a workationor just living the Freedom Lifestyle — there’s something in this video for you.

How and What to Pack for Your next Travel Adventure


List of Tools to Pack the next Time You Travel

  1. Tumi Carry-On 22″ Luggage
  2. Apple 13″ MacBook Pro with Retina Display
  3. Kindle Paperwhite with Wi-Fi
  4. Moleskin Classic Notebook
  5. Charles Schwab Bank ATM card  — Reference articleGet Rid of ATM Fees Once and for All
  6. Chase Sapphire Preferred
  7. CitiBusiness AAdvantage World Master Card
  8. Moo Business Cards
  9. 3m Nexcare Moisturizing Hand Sanitizer
  10. Travel Power Adapter
  11. Mophie Juice Pack Powerstation
  12. Rode Smartlav Lavalier Microphone for iPhone and Smartphones
  13. Samson Go Mic Compact USB Microphone
  14. Ethernet USB Adapter
  15. Bose QuietComfort 25 Headphones
  16. Xertube Resistance Band
  17. Adidas Men’s Sport Performance Climalite (for the gentleman)
  18. eBags Packing Cubes

Bonus items not mentioned in video:

  1. AirComfy Inflatable Travel Pillow (I never leave home without it)
  2. The Noteboard Pocket-Size Dry-Erase Board
  3. Tortuga Backpacks (awesome all-in-one alternative — a friend’s company)
  4. Portable and Adjustable Tripod Stand Holder for Smartphone for shooting videos)
  5. Case Logic Macbook Pro Sleeve (waterproof)

This list of equipment and electronics is constantly evolving. The clothes and gear you pack can change based on the destination, but it’s also generally the same.
But who knows, I might discover some different undies one day.
What are some items you can’t travel without? Do you have any tips for packing light?

6 Odd Ways to Be Productive While Traveling

Total Reading Time: 5 minutes.
It was only after four days that the feelings of responsibility and guilt began setting in. I was halfway around the world, settling into life in Southeast Asia. It was a completely new reality. The culture was intoxicating and I was ready to learn more about this exotic world.
The purpose of the trip was simple: to travel, work, and live the Freedom Lifestyle to the fullest. As you might guess, this isn’t an easy task, but it’s doable.
You’ve been there, we all have. You finally break away from the day-to-day routine and get an opportunity to travel, work remotely, or just work from home for a couple days. Yet, your mind starts playing this constant internal tug-of-war. It becomes a battle of work vs. play.

Staying Productive: How Do you Balance Work and Play?

How do you stay productive when you’re outside of your normal environment and/or comfort zone? When traveling, you’re presented with limitless possibilities of how you can go about your day. You’re continuously dazzled by “the new”.
This Southeast Asia adventure lasted 97 days. During the adventure I had to experiment and try many different strategies to stay productive. It wasn’t easy, and I made plenty of mistakes. After all, I was both traveling and working on multiple business projects. I learned some big lessons and was even able to pull off a product launch at the tail end of the trip — but only after learning those lessons.
Travel shouldn’t prevent the work from getting done. My readers expect content, regardless of the environment I’m in. Your customers, clients, and/or readers expect the same.
After all, living a Freedom Lifestyle is all about being able to do what you want, when you want, how you want (and even with who you want). I sat down recently and brainstormed some strategies for working more productively, maintaining your rituals, and still having fun while traveling.

The Strategy: Simplify

Keep things simple. Every experience and situation is different. There is no one-size fits all solution. The main idea is to avoid doing what doesn’t work. Focus on the 80/20 of your business/work.
Simplify as much as possible. You will not have as much time as you’re used to.
The key is to focus on two areas: the highest revenue generating activities, and high lifetime value work.

6 Tips to Stay Productive While Traveling Without Feeling Guilty

These strategies are useful for solopreneurs when they’re traveling, visiting family/friends, or working in any new environment.
They’re also useful for everyday humans who might be working from home, working remotely, or traveling for business.

1. Don’t Set a Schedule

If you set a schedule, you’ll set yourself up for disappointment. Even if you’re traveling alone, it’s likely someone or something is going to pull you away from your work. Plus, you want to have that flexibility. That’s the whole point.
If you get pulled away, you’ll feel awful and guilty. The goal is to avoid this feeling as much as possible.
Instead, set constraints, which is what Dr. Seuss did. Or at least set minimum thresholds. You can decide on the number of hours you must “work” every single day. Hit that number, and you’re good.
Decide whether it’s best to work in the morning, afternoon, or evening. But whatever you do, hit that goal. For example, during my trip to Brazil for the World Cup I made a goal to spend at least 3 hours per day working.

2. Have an Accountability Partner

Have someone either work with you at the exact same times, or check in with you daily to make sure you’ve hit your target. This can be someone from your company, or a business partner. But you can also hire a friend for the job.
Discuss the plan in advance and tell them how important it is for the both of you to hit your daily goal for hours worked. If there’s no incentive for this person to hold you accountable (they won’t also be working), make it fun for them.
For each day you don’t hit your goals:
A) You give them a dollar. Each time you don’t hit your goal, the money owed doubles.
B) You have to donate money to a cause you are against. Note from Arman: I like this one 🙂
C) You have to donate money to a charity of their choice.
D) You have to do them a favor. Or they get to make you do something.

3. Work Anytime and Anywhere You Have Time

This is a key lesson I learned and shared in this video. You never know when there will be some downtime.
Be prepared, carry your gear everywhere, and always be willing to put in some work — even if it’s only ten minutes.

4. Work Offline

You can brainstorm, mind-map, write, plan, design, and do so many more activities offline.
Don’t prevent yourself from working just because you don’t have Wi-FI. You’ll find that working offline is quite fulfilling. You’ll have less distractions, and will do better work.
Carry a pen and moleskin notebook at all times. Use your devices in offline mode. You don’t have to be online to get real work done.

5. Have the Right Tools

Invest in the right tools to make working from anywhere as easy as possible. Whether it be a USB microphone, a good set of noise-cancelling headphones, or a travel adapter. Invest in the tools you need now. If you don’t, you may regret it.
Natalie Sisson, of Suitcase Entrepreneur, has a ton of content on this topic. Here’s a list of some travel tools to help you work from anywhere.

6. Work When Others Are Around

This isn’t conventional advice, I know.
If you wait until you have free time, or try to break free from your friends or travel group, you’ll never get anything done. That free time will never come. It’s hard to break away from the group.
So what’s a traveling solopreneur to do?
Work in front of them. Pop on your headphones, get in the zone, and get to work. If you do this a few times, you’ll get awesome results.
This works because the people around you will see that you are serious about your work. They’ll respect the time you’re putting in, and will make it easier for you to make time.

What tips or advice do you have for staying productive while working remotely? Are there any methods or tools you rely on?
Photo credit: Sunny Saturday on Ipanema BeachCC License