5 Business Lessons from failing Kilimanjaro!

pink jacketLast month I started 2014 with a bang and conquered Kilimanjaro. I did not reach the highest summit, but I did have an awesome experience!

Although last year was pretty exciting (check out my review), I had a lot of downs in my personal life.

In order to challenge myself and take my business and life to the next level, I decided that I would make this the year that I conquered Kilimanjaro.

So, a bit of the background story…my fascination with Kilimanjaro started a decade ago during my first trip to Kenya.

We were at the border visiting a waterfall when my friend Joe (God Rest his Soul) asked me if I knew what that mountain was, and to be honest I didn’t think it looked that big, but when I found out it was Africa’s largest summit I told him, “One day I will climb that mountain!”

So here are some of the lessons I got from conquering that beast:

1.    Always start before you’re ready: I have always been naïve about how big the choices I make are, because I rarely go into extensive research of what it will be like, and what I will need to learn.

I think if I did, I’d probably be too afraid to start, and I would give everyone the award winning excuses not to start, which include, “I’m not the fittest, the most skilled, the best, or even the smartest,” but the difference is that I started.

How many times have you held yourself back thinking you need one more course? You need to read one more book? You need to ask one more person’s opinion?

Those are all self-made distractions and forms of procrastination that are part of missing out on how to grow your business & career, and live the life you truly deserve.


2.    Know where you are going: This will sound cliché, but if you don’t have vision, how will you know where you’re skygoing?

How the hell will you get there?

You have a choice to make: to live an awesome or average life.

Climbing Kilimanjaro was damn hard, and I might have been 150 meters shy of the top due to severe altitude sickness, but I would rather have pushed myself to climb 5700 meters than just say, “Oh, I will do it one day,” because the experience was epic!

Now I work with a lot of clients who are not clear on what they want; it affects their confidence and it affects their drive. Like for example, one of my readers from Dominican Republic just shared that because of her decision to choose what she wants, she has fast-tracked to become a senior manager in one of the leading banks in her country.

So where do you want to go? What do you want to achieve? Do you want to run a 5, 6 or 7 figure business?  Do you want to be working in the C-Level suite? Unless you decide and start to work on where you are going, it’s impossible to get there.

If you are not sure, you might want to check out my course Art of Living Your Purpose, which starts round two on March 10th.


3.     Plan like a mofo & expect the unexpected: Conquering a big beast like Kilimanjaro is seriously no joke. It took me a year of conscious thinking and 6 months of planning for it, but still I was not prepared enough for all the worst-case scenarios. I should have sought more advice from experienced people who’d gone before.

For example, the summit night temperature was -10 degrees colder than what’s normal for that time of year.

Have you thought about what you want? Do you get down and plan for it? Do you get various perspectives to see what’s missing? Be thorough, but don’t procrastinate – refer to first point.


Sunset4.    Understand the internal dialogue & that failure has its lessons too:  You know what I am talking about, right? That voice…That loud voice that sometimes self-sabotages with the constant thinking and obsession of a hundred reasons why you can’t do something.

It might be telling you that you are not good enough, not strong enough, not worth having it!

But the truth is, the voice is generally harsher than the reality, every one of you are put on this Earth for a reason!

During the night of the summit climb we were up at 11pm, planning to climb over 1000 meters with the temperature creeping to become colder and colder.  At around 6am I was tired, and most importantly I could barely feel my fingers.

The moment my fingers went numb, I felt that it was a sign; that I would not be able to do it and that I should not have been there. I fell to the floor and had my first breakdown of the year. I was terrified. I cried and cried, feeling that was it, I would be forced to go back down and I felt so sad that I was failing.

I was blessed with a wonderful guide, Lucas, who tried to warm my hands and hugged me, and the more I cried I started to say “You don’t understand I never fail, I cant fail…”

Having the breakdown was amazing, because it got me in touch with  unconscious internal dialogue, built up over the years with more and more challenges in business and life.

I wasn’t playing big because ultimately I wasn’t embracing uncertainty or thinking that the only constant is change! Instead I was staying within my newly-developed comfort zone of always succeeding.

How many times have you made decisions or chose activities that you knew you would excel at? How many times have you really gotten uncomfortable and felt really comfortable with uncertainty?


5.    Support system & having fun: Life and work without the support of vendors, teams and cheerleaders like friends and family would not be fun.


From the business side, if not for Milane (the newest member of my team) to hold the fort and make sure you got sexy tips while I was away, this trip would not be possible.

Also, if not for the whole team of porters and friends who were there, I would not have been able to do it.

Karima and I got altitude sickness around the same mark on the mountain. When she wanted to quit, I wouldn’t let her. When I had my breakdown, she wouldn’t let me. Without the support of the wonderful guides, Lucas and Habson, the success we achieved would not have happened!

Are you aware of your support system? Do you share with them how much they mean to you? Do you have any mentors or key influencers in the company who support you? Are you realizing in order to play bigger, there are other professionals, specialists, assistants and supporters you can add that can make a difference in your organization?

So I may not have reached the final summit, but I’m excited for pushing past the mental blocks and taking away from this experience!

What challenging experiences have you failed? What is the one thing you took away from it? We’d love to hear your thoughts

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