Why Successful People Do Not Always Feel Successful

I was chatting to a business owner I know very well a little while ago. By many peoples standards, including my own, he owns a very successful business that turns over in excess of $50m a year.


I was curious to know when he had realised that he had achieved success in business, but his response surprised me.


He told me that he did not consider himself to have achieved success because he had not achieved all his goals yet.


His answer really made me stop and think about how we evaluate our success and when we allow ourselves to feel it.


For every one of us success means something different, it’s totally unique to each of us. We all want to experience that feeling of being successful in our lives, so why do so few actually feel they actually achieve it?


Here are five reasons why successful people don’t always feel as  successful as they are.



  1. Their goals and milestones are not clearly defined.


Imagine you are in a car and decide to go for a drive. If you don’t know where your destination is and what you want to see along the way, how will you know when you have got there?


You are going to spend a long time driving around without ever knowing if you have arrived. You might enjoy the journey for a while but in the end you are going to start to feel frustrated by your lack of direction and achievement.


This is why goal setting in business is so important. You need to have big goals as well as smaller milestones, so you know when to celebrate.


Celebrating your small wins will help to keep you motivated to and keep moving towards your destination.


Relevant Article: Five Steps to Making Your Big Idea Happen



  1. You have attached an outcome that doesn’t happen to the achievement of a goal.


When I started my business, the results that I am achieving now seemed very allusive and out of reach. I remember setting myself a goal back then, that when I had secured my 10th client I would crack open a $150 bottle champagne I had been gifted by an old employer.


I passed that goal a long time ago but the champagne remained undrunk.


The reason for this is because when I set the goal I had also believed that the outcome of achieving that milestone would be that I would by then have a predictable system for securing new clients and I would feel like I had my shit together.


Funnily enough after 10 clients I didn’t….! So therefore despite reaching the goal I had set myself, I didn’t feel success and didn’t celebrate.


But the fact is that it is a valid and worthy milestone that deserves to be celebrated. The outcome is also a valid one too but I had mismatched the milestone and the outcome. We are always learning and growing and the path to mastery is a long one.


So we must celebrate the small wins along the way in the knowledge that our ultimate outcomes will come as long as we continue on our path.


Relevant Article: How to Execute Your Ideas and Start Winning



  1. You are swept along in your daily whirl wind and don’t stop to acknowledge your achievements.


As business owners we are often so busy that the achievement of our goals and milestones are forgotten or missed. By the time you have realised that they were achieved, the moment has passed and you don’t celebrate or allow yourself to feel the success you have accomplished.


Don’t allow your goals to be something you write just once a year, put in a draw and then forget until next year. Keep them on the wall by your desk, review them at least weekly (preferably daily) to make sure they are on track and you don’t miss your wins.


As soon as you achieve a goal or a milestone, celebrate immediately and acknowledge your success!



  1. You are comparing yourself to someone else’s journey and not your own.


No matter how much we achieve, there will always be someone else who as achieved more, in less time or is doing something differently to you.


The thing is, that is their journey and not yours. If I compared the work I do with business owners with Tony Robbins Business Mastery seminars I could allow myself to feel like a failure.


No two peoples journeys will ever be the same and the path you choose, the point where you are both on your paths and the timescale for walking that path are going to be uniquely different.


The only comparison worth making is where you are on your path compared to where you need to be.


We must strive for our own progress and to live our own best life, not someone else’s.


We must strive for our own progress, to live our own best life, not someone else’s. Click To Tweet


Relevant Article: Why You Should Stop Comparing Yourself to Others



  1. You are looking at where you have not yet been, instead of at how far you have come.


In the case of the businessman I talked about at the start of this article, who grew his business from nothing and is now turning over $50m a year, he was looking at what he hadn’t yet achieved instead of what he had achieved.


When measuring success it in terms of your current goals, that will always changing as you grow, develop and achieve, you will never feel successful, no matter how much you accomplish.


There will always be something new you want to conquer so therefore that feeling of success will be forever elusive.


The only true way to measure success is to look back towards where you started and realise just how far you have actually come. Then you will be able to recognise your success.


This businessman came from a poor background and started with nothing. He now employs over 200 people, has a beautiful family, gives back by taking an active role in projects in his community and has won numerous awards in recognition of his business success and community work.


By helping this man to look back at how much he has achieved already, he was able for the first time to realise just how successful he really is.



Claire Whitelaw Brown
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Claire Whitelaw Brown

Business Consultant at CWB Growth Business Strategies
Claire is a business strategist passionate about helping accountants grow revenue, profits and cash flow.

As well as being a Chartered Management Accountant (CIMA) and ex-CFO with over 20 years experience, she has also worked extensively with small and medium sized business owners to help them grow profitable businesses.

She's also a certified coach, NLP practitioner, Metadynamics TM Consultant and contributor for Kochie’s Business Builders.
Claire Whitelaw Brown
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