Middlebrook spent his childhood in the United Kingdom, but left home at the age of sixteen to travel, hitchhiking overland from England to India and then onwards to China, where he took the Trans-Siberian Railway through Russia, before again hitchhiking the following year through the Sahara Desert into West Africa, with further trips to South America. By the age of twenty-three he had travelled to more than 60 countries. Upon returning to the UK, and heavily influenced by Project Tiger in India where he had worked for some time during his early travels, he undertook a Bachelor of Science Degree from the University of Northumbria in Newcastle on Environmental Management, eventually receiving a First Class (Hons) in 1993. Interested in geopolitics and development economics, and under the Professorship of the renowned Geopolitical specialist Ewan Anderson, in 2002 he completed a PhD from the University of Durham Centre for Middle Eastern and Islamic Studies UK on Public policy and Poverty, looking at employment and growth economics in Ethiopia and India.
According to an interview with The National Newspaper of the UAE, Middlebrook has advised nearly 40 governments and traveling to over 100 countries. Middlebrook claimed that his commitment to human development was motivated by the sickening events of the 1983-85 Ethiopian Famine, following which he lived and worked in Ethiopia for seven years with the European Union and UK Government.
Middlebrook is a recognized advocate of structural reforms, economic diversification and specialization in transition economies, all of which are essential for accelerating growth and creating jobs. He is highly critical of Western state building efforts in the MENA region in particular, which he believes are driven by dogmatic prescriptions that fail to take into consideration the emerging political economy. At the same time, he is critical of governments who fail to place citizens and the environment at the center of public policy, believing that reforming state and executive institutions can only be successful if a strong and consensual social compact exists, built around clear public and private relations. His work in the Middle East focuses on job creation economic models that are essentially more inclusive.
Middlebrook has led much of the regional economic development and cooperation work in Central Asia for the US Government, including conducting economic impact assessments on the proposed US$28 billion trade, transit, energy and resource corridors for the Proposed New Silk Road Project, going back to 2002. He works closely with former US Presidential Adviser S. Frederick Starr, Founder and Chairman of the Central Asia-Caucasus Institute in Johns Hopkins University. Middlebrook acknowledges that the New Silk Road plan has seen limited success, largely as a result of weak regional commitment and lack of consensus in the international community on the centrality of supporting the extractive, trade and transit economies as critical to financing state operations in Afghanistan.
Middlebrook worked for the European Union and World Bank, based in Kabul, from March 2002 until 2007. He led and coordinated the development of the first National Budget for then Minister of Finance Ashraf Ghani Ahmadzai in 2002 and 2003. In 2004 he coordinated and led the successful Securing Afghanistan's Future exercise for the Government of Afghanistan and World Bank; a seven-year US$27.5 billion public investment program presented to an international conference in Berlin attended by 65 finance and foreign ministers. The concept of a double-compact, between the donors and the government of Afghanistan on the one hand and between the government and people of Afghanistan on the other, underpinned the program of investment in Securing Afghanistan's Future. The exercise raised over USD8 billion in international support. At the request of Government, working on secondment from the Vice-President's Office of the World Bank, he led the drafting of the first PRSP and played a key role in delivering the final National Development Strategy. In 2006 he was invited by the US Council of Foreign Relations to make a presentation on Moving Forward: Post-Conflict Reconstruction in Afghanistan In 2010 he led the Economic and Infrastructure Development (EID) work presented at the 2010 Kabul International Conference attended by Hamid Karzai, Hillary Clinton and UN Secretary General Ban Ki-moon and in 2011 he led the Economic Impact Assessment team for the US Government on the New Silk Road Strategy. In 2009 he co-authored a UK Conservative Party Back Bench paper on Afghanistan with Member of Parliament Patrick Mercer and the former Commander of British Forces in Afghanistan Richard Kemp.
In 2011 Middlebrook initiated a report on the 'Costs of the Arab Spring: A Road Map for G20 and UN Support', which was widely covered on BBC, Aljazeera and CNN. Gulf News called the report 'The Arab Spring Report', given its definitive approach to identify the drivers of unrest and a framework of corrective measures required by regional and international actors. On going work includes development of a White Paper towards a Marshall Plan for the Middle East (an Arab Stabilization Plan) and reportage on EU Sanctions on Iran.
In late 2011 Middlebrook received a call from Majid Jafar, CEO of Crescent Petroleum, the Middle East's oldest private oil and gas company, and Vice-Chairman of the Board of the Crescent Group of Companies, to formulate a Marshall Plan for the Arab World – the Arab Stabilization Plan (ASP). The ASP calls for massive jobs creation and investment in critical infrastructure and was developed by a team led by Middlebrook, and peer reviewed by Gary Sick, who served on the U.S. National Security Council under Presidents Ford and Carter and Parag Khanna. The ASP has been presented at the World Economic Forum and Davos.
Middlebrook is an advocate of global justice, human rights and security, and has been actively involved efforts to strengthen global policy and the reform of the United Nations system. Since 2014 he has been involved with The Hague Institute for Global Justice Commission on Global Security, Justice and Governance, co-chaired by former U.S. Secretary of State Madeleine Albright and former Nigerian Foreign Minister Ibrahim Gambari, and Directed by Dr. Richard Ponzio. He led the first World Bank Public Expenditure Review on the Security Sector.
Middlebrook has also advised on Justice and National Security issues in Afghanistan, Egypt, Sierra Leone, Somalia, Southern Sudan and Liberia for the United Nations, World Bank and UK Government and was part of the OECD Peer Review team for the Global Handbook on Security Sector Reform. and is a member of the Cranfield University Security Sector Management National Security Working Group.
Middlebrook was one of the three founders of the Great Ethiopian Run with world record holder and Olympic champion Haile Gebrselassie and Abi Masefield in late 2000. Middlebrook presented the idea to Haile Gebrselassie and former Prime Minister Meles Zenawi, and Abi Masefield secured the support of Brendan Foster. Middlebrook introduced Haile to Olympic Athlete Richard Nerurkar who staked out the original route. The Great Ethiopian Run (Amharic: ታላቁ ሩጫ በኢትዮጵያ?) is an annual 10-kilometre road running event, which takes place in late November in Addis Ababa, Ethiopia. By 2005, the number of race entries had grown to 25,000 participants and by 2010 there were some 35,000 runners competing. The race is considered one of the largest sporting events in Africa.
When the Public Works: Generating Employment and Social Protection in Ethiopia, Lambert Academic Publishing. 2009. ISBN 978-3-8383-0672-8. He has co-authored work in multiple other publications.
Middlebrook is also British-born singer and songwriter Jamie Brooke. During the 1980s he supported acts such as English Pop Rock musicians Chas & Dave, 10cc and Howard Jones. His debut album Violet Symphony was written in Afghanistan, recorded in India and mastered in New York and is distributed by The Orchard, and is available on Virgin, MTV and iTunes.