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Risk vs. Regret

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'I'd rather regret the things I've done than regret the things I haven't done.'

Lucille Ball


I just had lunch with a friend. They're 25 years older than me and they have lots of regrets. 

The regret of not doing more with their life - not carving out a career they love, not travelling more and not living somewhere they like.

Regrets are painful, they damage self-esteem and they wear us down. Research shows that 76% of regrets are about things we didn't do - things that would have taken us closer to our ideal selves, our ideal lives. 

“In the end…we only regret the chances we didn’t take, the relationships we were afraid to have, and the decisions we waited too long to make.” - Lewis Carroll

People tell me every day that they aren't risk-takers. They are too scared to change careers, to go after a life that they know would make them happier. 

They say things like: 


  • What if I don't like it?
  • What if I'm not good at it?
  • What if I fail? 
  • What will people think? 


I understand these fears, they're normal, I've had them too. But they blind us from the risk of regret. The risk of knowing we didn't even really try to create the life we wanted. 

What's the worst-case scenario if you pursue the things you really want? If they don't work out, go back to what you used to do, people may see you fail, and it may cost you some money, some time or energy. All things you can recover from and overcome. 

But, what's the worst case (and likely) scenario if you don't? You look back on your life with regrets - when you can't do anything about them, which is why they hurt so much. 

So you tell me, what is the biggest risk? 

If you think you're not a risk taker - but you aren't going after the things that are important to you, think again. 

If you have a change you want to make in your life, but something is holding you back, don't risk regret. 


Join the hundreds of people who have opened up to me in the last year, utilising the power of conversation to find the confidence to move forward. 


Recently my availability has become lower than ever, however, I have reserved a space for five of my subscribers who really want to overcome their fears and make an important change in their lives.


You can apply for a Free one-off conversation involving a life-changing visualisation exercise that will empower you to move forward. 
Click here to see if I have availability

If you want some motivation, watch
this compelling video from Prince Ea.


Subscribe to Work-Life Harmony Wednesdays  to receive a free weekly email that will help you live a more healthy, balanced and fulfilling life.

'I had a true breakthrough session with Simon. In just our first session together, he was able to identify the root fears blocking me and through his thought-provoking questions helped me come up with a solution to break that pattern.


I wasn't expecting this level of breakthrough in my first session with him, but was very pleasantly surprised! HIGHLY HIGHLY RECOMMEND HIM to help unlock your highest potential!'

- Shreya - Management Consultant, London

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Written by Simon Tomkins

31 August 2023
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