If you're seeking Clarity and Confidence to Create, "What’s Next...."

... Join us on a Highland Hack, specially created for Executives in Transition.

An exciting, new collaboration between Walking Coach and The Fresh Air Learning Company, planned for Spring 2017.


What is a Highland Hack?

It's a life-changing journey on foot through some of Scotland’s finest  and most inspiring scenery with a select group of fellow business leaders, experienced guides and fascinating guest companions.

On 20 March 2017, a group of six 'executives in transition', plus guides, will set off on a 3.5 day journey from Bridge of Orchy to Fort William, on the northern section of the world-famous West Highland Way.

If you're dealing with, or preparing for a major transition in your work or life, this is a perfect opportunity to take time out to re-evaluate, re-energise and refocus on what's next for you.



  • Preparing to take up new role?
  • Considering a change in career direction?
  • Experiencing role redundancy and want to figure out your next move?
  • Going through a career or life-related transition that’s impacting your work?

If so, you could be having some of these thoughts and feelings:

  • “I’m sinking beneath the pressure of this new role. I worry that I might not deliver.”
  • “I’m unable to find space or time to think about the future.”
  • “I’m going round in circles. I can’t break out. I’m feeling increasingly anxious.”
  • “What are my options? There must be more than this hamster wheel?”
  • “Am I in the right place? Where can I be more fulfilled?”
  • “This next role is exciting. How could I best approach it?”

Any of these sound familiar?

Highland Hack for 'Executives in Transition' can provide the direction or break-through that you're looking for.  

Clear your mind, give yourself space and receive friendly, expert, 24/7 support, as you create your action plan for the future and acquire the clarity and confidence to take your next steps.


How does it work?

Highland Hack is a hotel-hopping journey on foot through the wild beauty of the Scottish Highlands. The route forms the northern section of the West Highland Way and is accessible to a wide range of fitness levels. It’s a perfect setting to relax, reflect, and re-energise around the big steps you need to make. 

You will be part of a small group of other senior leaders, closely supported by an experienced coaching team who are also outdoor leaders and senior executives in their own rights.

Typically there will be a combination of coaching one-to-ones and facilitated group discussions, as well as lots of opportunity for free conversation and time alone.

Fascinating guest companions will share their own inspiring “executive in transition” stories at points during the journey.

As soon as you sign up, we’ll be in touch to explore your personal hopes and needs for the trip. We’ll work together to craft a flexible programme that draws on the power of the group, the skills of the coaching team, and the natural environment itself. We’ll jointly review this each day on the walk and co-create continuously as we go, ensuring you eventually return home having achieved exactly what you need.


What about Travel, Accommodation and Food?

You will make your own way to our starting point, Bridge of Orchy, where we will gather on the afternoon/evening of Monday - Day 1. At journey’s end you will make your way home from Fort William on the morning of Friday - Day 4.

We recommend you travel there by rail on the West Highland Line from Glasgow. The scenery is fabulous.

Each night we will stay in a different hotel and each day, your overnight bags will be transferred onward in our dedicated support vehicle. Hotels are all of a good standard, have a typical, welcoming Scottish charm and are set in stunning locations.  

Accommodation is sole occupancy (unless you request otherwise) and all meals are included. 

A welcome awaits at The Lime Tree, Fort William

A welcome awaits at The Lime Tree, Fort William

To see our selected hotels, click on the links below (opens in a new window).

Day 1.  Bridge of Orchy Hotel

Day 2. Clachaig Inn, Glencoe

Day 3. Macdonald Hotel, Kinlochleven

Day 4. Lime Tree, Fort William


How fit do You need to be?

Over three days, we will walk along the prepared tracks of the West Highland Way for 5 – 7 hours per day, travelling at a pace which allows for comfortable conversation. Each day begins with a short ascent, typically of around 250 metres and less than an hour of slow-paced walking. Throughout each day, we will also have plenty of stops for refreshments and to take in the natural world around us. 

If you have any concerns about this level of activity, feel free to contact us to discuss further.

What about the weather?

Scottish weather is wonderfully variable and an integral part of the experience! We will provide guidance on appropriate kit and clothing, and our outdoor leaders will check in with you regularly throughout our trip, ensuring your comfort and safety at all times. 

Highland Hack was quite simply the best discovery and learning experience I have been on. The small group and guest companion format was powerful, as was the tremendous coaching support available to us individually throughout the inspirational three-day journey. ~ Matthew, Business Owner

Your Investment

The fee for participating in Highland Hack - Executives in Transition is £2495 + vat.

This covers,

  • The bringing together of a powerful, mutually supportive group of fellow “executives in transition”and the facilitation of group discussions as required over 3.5 days.
  • Personal 1:1 coaching as required over 3.5 days, tailored to support individual needs, and the opportunity to carry this coaching relationship forward if required. 
  • Inspirational guest companions who will share their “executive in transition” stories.
  • Three full days of expertly guided walking along the upper reaches of the iconic West Highland Way. 
  • A mixed male/female support team of three. All experienced coaches, outdoor leaders, first aiders, and senior executives in their own rights.
  • Four nights hotel accommodation on a full board basis in double/twin rooms, en suite and single occupancy. Hotels have wifi.
  • Daily baggage transfers between hotels.
  • Dedicated Land Rover Discovery as support vehicle .
  • Collection from, and drop off at local railway stations.
  • 15% discount in-store and on-line at Cotswold Outdoor.

Meet the team

SANDRA CUNNINGHAM – Sandra is a Professional Certified Coach (accredited by International Coach Federation) with 15 years’ experience in supporting clients through major career/life transitions. No stranger to dealing with transition herself, she was previously an international marketing executive, directing from various management boards, then a senior communications consultant for large private and public sector clients. Now, founder and director at Walking Coach, she integrates her passion for, and knowledge of nature-based development with her coaching expertise, to create transformational outdoor experiences for leaders and their teams. Sandra is also a qualified hill walking leader.


DAVE STEWART – Dave is the MD of the Fresh Air Learning Company and originator of the Highland Hack concept. He works closely with ambitious organisations to develop their key leaders and teams.  His passion for the outdoors and experiential learning stems from early days in Scottish Mountain Rescue, and UK Special Forces. A Chartered Director and holder of various Fellowships and Masters, he has been an “executive in transition” a number of times across the private, public and not-for-profit sectors. He is also a highly sought after consultant, coach, facilitator, and mountain leader. 


3RD TEAM MEMBER – We will also be accompanied by a third team member who will drive our support vehicle and be a qualified outdoor leader.

Soon to be announced.




next steps....

These journeys are run for select groups of six senior leaders only, so please be ready to book early in order to secure your place.

Understandably, you will have questions. We would too!

In the first instance, feel free to contact Sandra by email or call her on +44 (0) 7980 747682.

Questions for Dave? Or want to go firm and book?  Email Dave here or call him on +44 (0) 7776 153 428. 

Once we receive a firm booking from you, we will confirm availability and invoice you for a non-refundable 50% deposit (returnable only if we have to cancel the journey).  

Upon receipt of payment, we will email you immediately with full joining details for Highland Hack - Executives in Transition. 


Highland Hack has been variously described as a "health club without walls", a "sandpit in which to develop and test ideas", a "business network to provide challenge and support", and an "open-air classroom to pick up some great skills and knowledge".

For us, it is simply what we love to do!

We look forward to walking with you, and providing you with an inspiring, memorable and high value experience that helps you get clear and confident about your next steps.

Download the PDF Brochure here.