Richard Oakes on “The Equation” – improving life, one day at a time

This event followed our previous roundtable with Matthew Syed in sharing inspiring, transferable lessons from the world of sport. It gave an opportunity for our attendees to think creatively and share ideas with their peers in a relaxed, fine-dining environment.  

Here are the key lessons that Richard shared with us on the evening: 

The importance of balance

The true measure of the performance of an individual or team is the level at which they can perform sustainably for the long-term. A short-term boost in performance and output can feel motivating, but can also result in feelings of burnout and disappointment.  

Managing your own performance and that of your team, all comes down to striking a balance between the energy you put into your work and your longer-term wellbeing. You should also look for balance across your professional and personal lives.  

Defining your purpose and values

To succeed and stay focused, even during times of challenge and adversity calls for a clear specific purpose and values. You might choose to define these at individual level, group level, or even both.  

 This will help you determine the right steps to take when unexpected events throw you off course. A strong purpose, underpinned by appropriate values can outlast the short-term demands of a specific task or challenge and keep you focused on the right actions.  

Laying firm foundations

Success in sport, work or life depends on constantly refining the fundamentals of what you do. Whether it’s physical fitness in sport, or legal knowledge for an in-house lawyer, refining those fundamentals over time is just as important – if not more so – than acquiring new skills.  

New emerging trends will always generate a lot of attention, and we always recommend that in-house lawyers should keep a close eye on them. However, that shouldn’t be at the expense of the proven fundamentals of your role.  

Having a plan and being intentional

As an individual and as a leader of a team, setting a clear vision and plan which you pursue intentionally can be highly motivating. As a leader, you may have a clear vision in your own mind, but without transferring this into a written plan, your team may lack the clarity they need.  

Articulating very specific goals may be enough in some instances. However, complex goals may call for a more intricate approach, where you articulate how the goals will be achieved, as well as the steps that are needed to complete them.  

The Stoic mindset – “The obstacle is the way”

In recent years, interest in Stoic philosophy has surged and it has proven particularly popular in the world of elite sport. One popular concept from the Stoics is that “the obstacle is the way”. Richard encourages individuals and teams to see obstacles as something to think creatively to overcome, rather than something to avoid and work around.  

Finding a way around a problem can be tempting and can even feel more creative. However, this might not be as novel or original as you think. There is often much greater value and less competition, when you embrace the opportunity within the obstacle and find a way to overcome it.  

Process over prize

Some of the most successful people in work or business achieve great things by taking a counterintuitive approach to work and life. Rather than focusing directly on the big prize or outcome, they set a habit of taking the small but consistent steps that will move them closer to their goal.  

This gives you a daily goal to achieve and a sense of fulfilment every day, rather than having to wait months or years for a big event or win. Knowing that you have improved at your craft can also help you feel accomplished and successful, even if you fail to win a big prize or event.  

Bringing ‘The Equation’ to life for in-house legal teams 

We’re very grateful to Richard for giving our guests the inspiration, clarity and novel perspectives needed to lead their teams to success. The simple, down-to-earth concepts he shared can transfer very effectively to help legal teams thrive, even in the most challenging times.  

More about the Expanding Horizons series for General Counsel and Heads of Legal

Feedback from guests at our first two roundtable events has been extremely positive and complimentary. The last of our three events takes place in April 2026 and we look forward to sharing more actionable insights once the series has concluded.  

About Richard Oakes

Richard is best-known as an elite cyclist and was an eight-time UCI World Masters Cycling Champion. He set a new Masters World Hour Record in 2023, aged 54. Richard co-founded and rode for Team Ohten Aveas. 

As CEO of Ohten Group – a social technology group – he now works with businesses and their communities around the world to help realise their full potential, by focusing on the wellbeing of their people and on creating great client experiences.