5 Strategies to Live with No Regrets as a Founder

By board advisor, Deri Llewellyn-Davies

No one wants to come to the end of their lives full of regret. As a founder, mistakes are part of the journey, but what you want to minimise is the impact that they have on you personally, and your growth as a business. I’ve identified 5 key regrets people have admitted to and shared my strategies to avoid repeating them and instead, live with meaning and purpose.

Regret #1 – Not Going on that Adventure

This regret aligns with my own drive for travel, adventure and experiencing the world. However I uncovered something deeper; a regret that goes beyond just seeing new places. For most people, it wasn’t just about travel, it was about experiencing life to the full. This included breaking from routine, saying yes to new experiences, embracing their curiosity and the unknown and seeking adventure before it’s too late.

How do you reframe your mindset so you can make sure you don’t fall into the trap? Consider the following:

• Don’t wait for “one day.” The perfect time will never come. Make adventure a priority now.
• Travel, even if it’s local. Step outside of your normal patterns and expose yourself to new ideas, people, and perspectives.
• Take action—whether it’s booking a trip, learning a new skill, or pushing yourself into unfamiliar territory.

Regret #2 – Not Living Your Truth 

This one is functional. Living a life that aligns with your truth is one of the greatest forms of freedom. When running a business, it is natural to want to have as much freedom as possible, otherwise you wouldn’t have chosen to work for yourself. But managing that freedom can be overwhelming. With so many options and few people telling you what to do, focusing on what will bring you the most satisfaction and meaningful results is hard. So many people spend years or even a lifetime wearing masks, conforming to expectations and suppressing their real desires or steering away from difficult truths. This ultimately comes at a cost – a life that is unfulfilled, inauthentic, and regretful. 

Be honest with yourself, be clear about your goals. Make choices that reflect your values, not just what is convenient or comfortable or what other founders are doing. Be proud about distinguishing yourself, don’t be afraid to experiment and speak your truth even when it is hard. Authenticity will always attract the right people who will help you on your journey. Whether they are a mentor or someone on your team, they will enable opportunities for you and help you evolve.

Truth requires courage, but nothing is more painful than realising you have lived someone else’s life.

Regret #3 – Not Pursuing Mastery

This one may surprise some, but not everyone. There has never been a better time than now to develop mastery. Access to knowledge, technology and opportunity has never been greater and thus being an entrepreneur is more enticing and realistic as a result. Some people in the end settle for mediocrity, never truly hone a skill, craft or expertise. Mastery isn’t just about professional success; it’s about deep fulfilment and leaving a lasting impact. Regardless of your niche, deciding what sort of legacy you want to leave

Identify what fascinates you and commit to continuous learning. Invest in yourself, whether through coaching, training, reading, or hobbies. Furthermore, mastery doesn’t just have to revolve around professional success, the lessons can be carried throughout the different chapters of your life, and you can leave something for future generations to learn from.

Regret #4 – Neglecting Family & Friends

This regret will eat away at you over time. Don’t let this one slip. As time goes on, the deeper this regret becomes. The time you could have spent with loved ones you will never get back. Careers, ambition, and personal goals are great and healthy to have, but don’t let them take precedence over relationships. Many realise later on that the moment with family and friends brought true wealth and happiness, rather than materialistic things that only spark joy for a brief spell. 

My main advice, and something I make a priority, is to not “find” time but make time. Schedule regular check-ins with your internal team, plan family activities, and dedicate hours for mealtimes and relaxation. You don’t have to live by a calendar, but blocking those key times for just loved ones is imperative to stay grounded and remind yourself of what you have to be grateful for. Practising gratitude pays in spades. Don’t aim for perfection, just be visible and engaged. Work on your listening, learn how to be a better partner, and strengthen the relationships you have. Reach out to people you haven’t spoken to in a while and re-ignite those friendships. Entrepreneurship can sometimes be a lonely endeavour, re-connect and keep your distance from those who hold you back. The action is simple – just do.

Regret #5 – Not Following Your Own Path

As you would expect, the regrets get deeper and more profound as we progress. This one is significant. Some of you may already be on the right path. For those who aren’t, we have work to do. Unfortunately, too many people choose a life or career that others expect of them rather than what truly aligns with their values. Fear of change, financial uncertainty, or external pressure keeps people locked in careers, relationships, and lifestyles that don’t fulfil them. This regret builds over time, slowly turning into frustration, resentment, and, eventually, the painful realisation that time has run out.

To combat this, be brutally honest with yourself. Are you living a life on your terms or someone else’s? We touched on this with another regret, but it’s important to reinforce the notion so you can make a difference. Take the small steps to build that momentum. Start by making choices that align with who you truly are, not what you are told to be. There are a lot of influencers in the entrepreneurial world, but that doesn’t mean you have to give in to their vision. Own your uniqueness, find guidance through a mentor or a coach, and carve out your path that doesn’t take notice of doubters. 

Final thoughts 

There is one regret that ties them all together – the regret of inaction. The things you don’t say, the paths you don’t take, the moments you don’t prioritise, the skills you never master. Regret isn’t about what went wrong – it’s about what was never tried. If you try one of these things and they don’t work out, that’s fine. Don’t punish yourself for trying. Be bolder with your choices, don’t question the outcome and act on your desires. Ask yourself, right now: What’s one thing you can do today to avoid a future regret?

Now, go do it.

About Deri Llewellyn-Davies, board advisor and co-founder of Freedom Founders

https://www.linkedin.com/in/thestrategyman/?originalSubdomain=uk

With a thrill for adventure and the unknown, having climbed 5 of the world’s highest summits, completed ironman and run 6 marathons across the Sahara Desert, Deri Llewellyn-Davies has a deep belief that anything is possible.

As a No1 best-selling author of Strategy on a Page and Life’s great adventure, Board advisor, international speaker and mentor, Deri has been shaping attitudes and ideas in business for over three decades and his unique methodologies and theories have been adopted in board rooms around the world. Through his work, he has uncovered what it takes to be a strategic leader and how to turn inspiration into meaningful change.

Having advised over 327 boards, Deri has accumulated all he has learnt and turned his attention to co-founding Freedom Founders. This is a deeply connected global community of  ambitious founders with programmes and curriculums designed to support their journey through navigating the unique challenges of scaling their businesses, ultimately inspiring and empowering them to succeed in business and life.

Deri lives near Malvern with his family and is a proud dad to four children, 4 chickens, 2 dogs. He continues his life of adventure and is currently planning for Everest 2027 and some new world record attempts with Project Cant.