The Art of Reflection – How to Stop Living in Your Disappointments.

When you look back on your year are you hard on yourself? 

Most entrepreneurs are. 

Maybe it’s because when we do look back the parts that stay with us the longest are the disappointments we experienced. 

Why do we hang on to our disappointments? 

There is a lot of psychology behind all this and this post is not meant to be therapy, but in terms of your business it can be helpful to understand what’s happening. 

I do a design component at my events addressing this very thing where people look at their past year and, without fail, everyone forgets or downplays their victories. 

How do you get an accurate perspective on past accomplishments? 

To shed some light and appreciate what you’ve achieved during the year ask yourself the following questions.

During the year: 

1. What were your major victories in your business?

2. What were your major victories in your personal life?

3. What achievement are you most proud of?

4. What was the biggest risk you took?

5. What new skills, perspectives or insights did you gain that will positively affect your


6. What important life lesson(s) did you gain?

7. Did you have a major setback(s)?  If yes, how did you handle it and what was the final


8. What progress or ground did you take towards the future you are building?

What makes you happy about last year? 

Your responses can help you realize the full richness of your accomplishments and the lasting meaning that it has in your life – meaning that you may have been overlooking.

Looking Back in Order to Plan Ahead - How to End the Year in a Really Great Way

People have different relationships with the ending of one year and the beginning of another. Some people love this time of reflection and planning while others, not so much. 

Regardless of what side of the fence you land the end of the year always brings with it something else – the start of a new one and the chance to improve. 

Looking back in order to plan ahead can pay huge dividends in both our business and personal life. 

Many people hate looking back. Why is that?

When we look back on the current year it’s human nature to focus more on what went wrong instead of what went well. Regrets are natural.

Using this simple exercise this year I discovered that I was tired of struggling with a necessary (but annoying) component of my business that I dreaded doing. I learned it was draining my energy and passion and I regretted not doing anything about it sooner. So instead of struggling I hired a professional to take that part over.

What a huge learning – and relief - for me! I can now focus on what I’m best at, and love to do. And I wouldn’t have been able to do that without releasing some regrets.

How do you release regret?


Ask yourself some very pointed, very specific questions. And write down your very pointed and specific answers. 

At the top of the page write: 

When I look back at my year… 

What did I deal with, resolve or in some way handle for the first time? 

What did I decide I would never do again?

What lesson(s), painful or otherwise, did I learn? 

What did I improve or advance in some way? 

What new insights and perspectives did I gain? 

In what areas of my business/life did I succeed? 

In what areas of my business/life did I fail? 

What new life ambitions did I create? 

The real key to getting past the regret is to ‘recover’: rethinking and reframing past events allows you to let go and move forward. But you can’t do any of that without first acknowledging - the good as well as the bad. 

And remember, the insights don’t all need to be about the business. Using this reflection technique I rekindled my passion for learning how to surf.  Now I can look forward to building my business and recommitting to a personal passion this year. All I had to do was take a quick look at the current year before I plan ahead for the one coming. 

Too many of us drift from one year into the next without fully realizing what we’ve accomplished and what we can accomplish in the year ahead. 

Using these questions can help you understand and acknowledge what you’ve learned and can have a direct, and potentially huge, impact on your upcoming year – it has on mine. 

If you had one big disappointment from last year that you could reflect upon, acknowledge and release what would that be? How would letting that go help you in the year ahead?