My Point of View by Ben Kenobi
Ben Kenobi writes in today about how he would like to figure out what to do now that he is retired, which he feels uneasy about. Listen now!
Ben Kenobi
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My point of view by Ben Kenobi

A long time ago, in a galaxy far, far away… a human being had regrets. That human being is all of us, because nobody gets through life without having some regrets. At the same time, the subject of today’s episode of Character Coaching is also dealing with a heavy case of the regrets, and it’s making his life pretty miserable. His name is Ben K., and he feels like he’s made some wrong career moves. 

For his entire life, Ben’s been running around the galaxy (or, uh, country….) fixing problems and putting out fires. After a long and taxing career, Ben has finally entered retirement, but he doesn’t feel at peace with his decision. Part of it’s because retirement doesn’t feel as fulfilling as he thought it would be, and the other part is that he keeps getting called back out to perform his old job when the situation requires it. On top of all that, he’s pretty shaken up, because he’s starting to wonder if he was even good at his old job back when he wasn’t retired. 

Is sort of situation familiar to you? If that’s the case, then this episode of Character Coaching is definitely for you!

And Ben, of course. Can’t forget Ben. 

Ben’s first journal entry: my point of view 

Entry One:

“Hello there! Hopefully I’m reaching you on a secure channel. My name is Ben, and up until recently I had a very important, singular job to do… watch over and eventually train my successor. Since my colleagues were… well I guess you could say we were downsized, I’ve been in a sort of self-imposed, semi-retirement so I can focus on this one task. Now things have changed. I’ve been forcefully brought out of retirement. Forced to run around the galaxy, feeling uneasy about what to do next, playing the part of a hero. I’m getting too old for this sort of thing. I’ve lost so much because of this job... regrettably much of it due to my own folly. Being in my line of work you don’t always get to retire… though I can’t say I was enjoying retirement. From my point of view it feels as if I haven’t any choices in life at all, that my destiny is spelled out in the stars. My master would tell me to remove all doubt and fear and to have faith. To stop trying and just do…What should I do?” — Ben K. 

First impressions: a destiny written in the stars 

Ben’s first journal entry felt pretty relatable, didn’t it? It certainly did to me. After making a lot of decisions and going through the motions, he’s finally looking back and assessing all the “damage” that’s happened in his life, if you will. Does he have regrets? Would he have done things differently?

Who knows? Wouldn’t all of us have done some things differently along the way?

While it certainly doesn’t pay to hang onto regret, regret can certainly be a useful tool in pointing you toward what you’d like to do next. Once you’re reassessing things, it helps to take control of the situation, look around and ask yourself, “Okay, that wasn’t the best outcome, but it doesn’t have to be like that going forward. What’s next?”

It’s important to ask that question for one simple reason: because we never want to be complacent in our own lives. No one’s life should be at the mercy of outside forces, but some of us end up in that position unwittingly (or because of the choices we’ve made). That doesn’t make us wrong for making those choices, but it also doesn’t make it right to hang onto certain lifestyle behaviors simply because we chose a certain life path a long time ago. 

As far as Ben’s situation goes, I need to ask him a few questions before I can give him any advice. After all, as coaches, the last thing we want to do is deliver some boilerplate life lessons and send Ben on his way. Doing that would be akin to giving Ben a bunch of advice that would be amazing if he were living our lives, but not his life. So, I’m going to get a little deeper here. 

The first questions I’d like to ask Ben are: what did you see yourself doing with your life when you were younger? And does that image conflict with what you always wanted to do, or is it in line with what you had planned? 

My next question involves Ben’s personal life. I’d ask: are you actually distancing yourself from your job, or are you distancing yourself from the feelings of regret you have over the mistakes you’ve made? Knowing the difference between these things will help us give much better advice regarding Ben’s specific situation. 

Let’s follow up with him, and go from there. 


  1. What did you see yourself doing at this point in your life?
  2. Are you distancing yourself from the actual job, or the feelings of regret over your own mistakes?

Next: a galaxy of regret


“I recall Qui-Gon would ask me why I was so concerned over where I was going and never with what I was doing at that moment. I thought I’d grown so much since those days but his words still seem to be lost on me.

When I thought of the future I felt certain my order would flourish and spread peace to those who were most in need of it… Now I sit and wait for my role to end while wondering about what could have been.

I’ve made so many mistakes that when I close my eyes they’re all I see. It’s hard for me to disconnect those feelings from what needs to be done.” 

What a spicy journal from our main man Ben. These kinds of journals are always particularly illuminating, because they give us a deeper window into our client’s emotional state. More than just getting his story, we’ve learned that one of Ben’s greatest problems in life is his relationship with regret. He regrets so much about the past that he feels paralyzed and unable to do anything about the future, even if he knows what needs to be done. 

Regret, while strong, is just another emotion. Like every emotion, it comes and goes. Unfortunately, when it starts to impact our lives in — sorry in advance for the pun — regrettable ways, then it’s no longer serving us in the same way other emotions might. Instead of helping us make choices about our future, we become petrified, and don’t make any decisions, because we’re too afraid that any decision we make will be the wrong one. 

Ben’s problem here is exactly that: he seems well-possessed enough to take charge and do what needs to be done for the good of his company… or universe… but he can’t seem to shake the feeling that no matter what he does, it’ll be wrong. If he could only get rid of some of those feelings of regret and dispense with his anxiety about the future, he’d remove any and all roadblocks to doing what he does best.

With that said, let’s check in again with Ben and get some answers to our following questions, shall we? 

Follow-up Questions: 

  1.  Is it too late to accomplish your goal of creating peace?
  2. You mention your teachers a lot, do you believe they didn’t make mistakes themselves?

The check-in: may the force be with me

Closing Journal:

“I go by Ben as a reminder of what I lost due to my own blindness. It appears, however, I am still willfully ignorant of many things. I blame myself for things that should have been obvious in hindsight, all because I refused to focus on the present while they were happening. I have a chance to be different now, to be more mindful of my surroundings than I was all those years ago. Retired or not, I am what I am. Within turbulent emotion there can be peace. Within chaos there can be harmony. I come from a long line of those who made many mistakes in their quest to help others, yet I do not regret ever following their example.Thank you, friend. May the force be with you.”

Ah, what a satisfying final journal entry from our friend Ben. It seems as though he’s come to the realization that simply dwelling on regret isn’t going to make him perform any better at the tasks he has set before him. More than that, he’s realized that his life hasn’t been wasted just because some of his plans didn’t work out… instead of that, he’s had a lifetime to learn how to move forward and become who he needs to be in order to succeed.

This is a great illustration of how many problems that seem physical and concrete are, instead, thinking problems. They begin in the mind and hinder us from living up to our true potential because we allow our errant thoughts to guide us. Once we break free from those errant thoughts, however, we’re able to see clearly and achieve our goals in a healthy and natural way. 

That’s amazing news for Ben, and even better news for the galaxy. If you’re interested in getting the same kind of coaching experience our friend just had, I’d highly encourage you to check out our main page and learn more about what we do here at The Journal That Talks Back!

Meant to go on a Star Trek instead of starting a Star War? Check out that time we coached Nog Ferengi.