What’s the biggest career mistake you would gladly make again? 11 leading entrepreneurs tell us.

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“Mistakes are the growing pains of wisdom." -William Jordan

In career, and in life, we make mistakes. You can’t prevent them and avoiding them is a mistake in itself. Business leaders make many and have the scars to show for them. They can cause harm and loss, but they can also open doors and serve as learning opportunities.

We asked some of the Middle East’s business leaders and entrepreneurs a simple question:

What is the biggest mistake you made in your career that you would gladly do again if you go back in time?

Here is what 11 of them had to say:

Ihsan Jawad
Partner, Honeybee Technology Ventures
Previously:  CEO & cofounder, Zawya.com (acquired by Thomson Reuters in 2012)

One almost fatal mistake early on in Zawya's formation was to kick off operations with smaller capital than the business required.  This could have killed the business when things did not go to plans and indeed that's the main cause for most start up failures.

However, looking back at it now, I may just do it again as the situation made us take the right survival choices rather than just drift along and disappear into irrelevance. The real constraint resulting from that mistake forced us to get creative and innovative.

Rabea Ataya
CEO and Cofounder, Bayt.com
Also incubated a number of startups including GoNabit, Mumzworld.com, YallaMotor, and DoctorUna.com.
Previously: founder, InfoFort

“I have continually underestimated the complexity involved in starting new businesses.  This recurring mistake has been a blessing as I would have likely not taken on any new ventures had I understood a priori how challenging they would be.”

Hussam Khoury
President, Jabbar Internet Group
Cofounder, Maktoob.com (acquired by Yahoo in 2009)

The biggest mistake was to jump into a new idea or venture like Maktoob at a time that did not make sense, and with little study of the situation, with everyone around telling me you are crazy! 

Yousef Touqan
CEO, Flip Media

I think the best "mistake" I made was to choose to work with a young startup digital agency instead of taking a comfortable and safe client-side role as a Director of Marketing. I'm so proud of everything we have achieved together at Flip in the last 8 years, and I'd gladly do it all over again.

Omar Koudsi
Cofounder and CEO, Jeeran

"I can't think of one "big mistake" but I have made a ton of mistakes that have built up my experience and I am glad I went through them.  As they say, good judgment comes from experience, and experience comes from bad judgment."

Laith Zraikat
Founder, Olgot.com
Previously: Cofounder, Jeeran

The biggest mistake in my career was not getting some corporate experience before I started my company. In retrospect, it would have been impossible to have that anyway since I started back in 1997 while in my second year of university. There have been tremendous advantages to startup at that time and under those circumstances so I would gladly make that mistake again :)

Corporate experience will give you reference points when dealing with employees and trying to put yourself in their shoes. For me it was all guessing, as I was never an employee. In the least, they would not be looking at you as someone who has not been in their shoes. 

Rama Chakaki
Cofounder, Baraka Ventures

My biggest mistake was leaving my last corporate job as a COO, to startup a business in a domain I knew nothing about. 

I was in the IT and telecom sector, and yet my heart was in social causes & development. I felt we could combine both. I saw a need to explore a new business model that combined social and financial goals, as existing businesses often placed all the emphasis on a financial bottom line, with little attention paid to their social or environmental impact.

So I left the job, and risked all.  Because it was uncharted territory for me and unfamiliar to others in the region, I had to learn by trial and error.  I invested in social ventures that failed miserably, but I learned a lot from those failures.  

The flexibility of running my own business allowed me to step outside the office, work in the field and gain amazing insights on social and environmental challenges first hand.

Venturing into a "green field" also allowed me to explore creative ways to get things done.  The lack of financial support from third parties kept me alert to making the business run on a "bubble gum and shoe string" budget.

Perhaps it was a mistake to risk everything and invest my savings at a time when I could have been earning a significant salary in a booming economy.  But I became fearless where it came to financial risk and learned the merits of a values-driven business.  Best result: I am surrounded by a community who believes in social business.

Alper Celen
Founder & Managing Director, Commit Network

Most people quit their consulting jobs at McKinsey after many months of soul searching and rigorous comparison of numerous corporate opportunities.  So, when I quit McKinsey in 2009 to “become an entrepreneur” without a clear long-term plan, many thought that I had made a major career mistake.  

My McKinsey colleagues had a hard time understanding how I could take on such a risk with a wife and new baby to support.  My friends thought that the first step after the Firm was the most important in one’s career and that I should have taken a director or CXO position in a tech company instead of founding my own startup. 

On most accounts, my choice to let go of a dream career and guaranteed income and benefits as a consultant seemed like a mistake. Yet, I would make that mistake all over again if given the chance. The truth is that the best reason for invention is necessity. Without fully facing the risks of being an entrepreneur, I would not have met the people that I met, I would not have had the ideas that I had, and my company Commit would not have shaped as it did.  Thus, my advice to aspiring entrepreneurs is often summarized in one word: “quit!” 

Of course, be sensible in doing so and calculate your options in case of failure.

Mona Ataya
Founder, Mumzworld.com
Previously: Cofounder, Bayt.com

All choices I have made and will continue to make are based on the data I have at the time, my experience and my “gut” as the final tipping point.  Some of these choices were perhaps not the best, but were resulting in learning nonetheless. So I don’t consider any of these choices mistakes, but rather pieces of the puzzle that are guiding me to where I need to be.

Fadi Ghandour
Founder & Vice Chairman, Aramex
Cofounder & Director, MENA Venture Investments

For me, there are no “biggest mistakes.” There are a series of many smaller ones that are gems of knowledge in my life and I am sure in the life of every entrepreneur.

That is how we have built our businesses over the decades, making mistakes and failing and learning along the way. I am a firm believer (out of experience) that through failure you learn, and that through many small failures, you learn everything.

Trial and error has been a guiding principle for me ever since I can remember. Not because I took it up deliberately, but as I was building the business, I discovered that as I try things, and take decisions (many of them every day), I am making judgment errors, and other mistakes. But I also discovered that every “bad decision” I have made was something that stuck in my mind, (meaning I learned from it, that is why I remembered it) and these mistakes where the building blocks of my cumulative experience and knowledge. 

So I would never trade these mistakes ever... they are what got me here, and I would repeat them again and again. Just like working in a laboratory, you try and try to find the right formula that clicks.

Dany Farha
Cofounder & CEO, BECO Capital
Cofounder, Butlers, and Intercat
Previously: Cofounder of Bayt.com

I have had the privilege of being an instrumental part of and co-founding a multitude of businesses over the last 18 years. 

At the beginning of my entrepreneurial journey, I was adamant about performing all the core functions in the company.  I self-inflicted the painful process of shadowing not just core functions but key business areas that I determined could lead to the success or failure of the company, all the way down to fraud detection.

I spent many days, weeks and months performing these tasks myself, working very closely with store keepers, accountsclerks, delivery drivers, technicians, receptionists, sales managers, HR staff and more as I focused on learning many facets of the business.

This was a consistent mistake in that it was extremely tasking on my time, and I often worked 15 hour days, 6 days a week, to make up for my own key management duties. I was often rightly accused by my friends and partners of not delegating, being too “hands-on,” and trying to do too much.

I also did much of this reluctantly and didn’t always enjoy the process. But in hindsight, what seemed to be a consistent mistake, even 15 years on, now seems like a fantastic investment. The drawbacks can be severe, particularly slowing growth in the earlier years, especially when, as a founding managing partner, you are so instrumental in driving the growth of the business.  My pursuit for knowledge and functional excellence took away from my being strategic, creating an elaborate growth plan, hiring and managing talent to execute the plan and spending time with key stakeholders.

These actions worked against me eventually, but they were a “mistake” that I would repeat in a heartbeat. The benefits are innumerable. A detailed command of every aspect of your business, enabling you to better manage these functional managers in the future, understand what is possible and how to raise the bar and promote innovation. These skills are often transferrable, hence the ability to compound this knowledge and experience across functions and businesses. 

The pluses include camaraderie and being able to identify top performers; many of our stars came from the hidden bottom of the ranks.  Identifying new business opportunities, products and services, acquisitions and new markets also come out of this tiring process.

To demonstrate that we still walk the talk, my partner and I at BECO Capital are once again performing all the core functions ourselves, right down to the filing, and hiring key positions only once we’ve mastered all the details that go into building a high quality investment firm. The big pay-off today is for our portfolio companies as we transfer these experiences to inform them where appropriate.


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