Our weekly advice column from Giselle Massi, a former journalist with The Denver Post.

G: A close friend is deep in thought these days as he contemplates the next phase of his life. Not quite a senior, not quite middle-aged, many professionals who are just like him spend a good chunk of time looking back on their career and know in their gut there really is something much more fulfilling that might be ahead for them… if only. They may also admit to themselves and to those in their circle that they have stayed way too long in their comfy, familiar job. The one they have outgrown or no longer enjoy.

Sometimes staying put is the result of certain obligations, like those to family or to having to pay off debts. Or maybe it’s about putting a gifted child (or two) through private lessons and higher education or keeping up with child support payments. It is all too easy to mistakenly think that making the leap, pivot, or move to a different position but still in their field – or taking up something unrelated – would have served them far better than where they find themselves now, as cushy and “risk free” as their life seems to have become. There’s no guarantee one way or the other. Things happen that are out of one’s control, whether one makes the leap or doesn’t.

I see employment and personal fulfillment as difficult and thrilling as walking a tight rope. The steps must be made carefully. We can only come to certain realizations about those steps when we are willing to see with an open heart while using our rational side, and without harsh judgment.

Not everything is meant to happen at a set time, place or order. For example, people come into our lives who suddenly can open doors for us that we didn’t even realize we wanted to pass through. Or shut us out, to our chagrin, and then invite us later to the party. What is constant through the ups and downs of doing something that matters to us, to earn a living and pay one’s way (and often pay other people’s way!), is the persistent challenge of getting to the core of what one truly wants to achieve in life. Because that core shifts as we evolve into our various incarnations.

Striving for that truth is a process involving much self-talk and introspection, as well as talking with trusted advisers. By process, I mean a passage of time, where analysis and investigation will reveal one’s nature and passions, and time is spent researching what compatible work exists, that will bring it all together. The win-win-win result. The right work gets performed by the right person at the right time.

My friend is quite computer savvy, so he used the assistance of artificial intelligence programs to help with the self-examination. He compiled what he called an Identity Report. It was a long document that itemized his strengths, weaknesses, interests, priorities, talents, patterns, and traits, that serves as his individualized map. The purpose of this document is to help him clarify who he is now, and who he aspires to become, all within the context of what was revealed about his nature and patterns, by many AI questions and prompts.

The map also shows what obstacles, or what I like to call “self-sabotages” are now front and center, holding a person back from “getting on with it,” as my dad would say. Creating one’s identity, getting on with it, is actually a life-long endeavor, made more challenging because of those ever-changing, niggling blocks of resistance.

The Identity Report organized the information in a non-judgmental narrative, so he can review it and consider what rings true, or truer. And over time, he may see that it needs updating to keep him aligned with “what he thinks he wants” to how seriously he is orienting his choices so as to enhance the likelihood he will be successful in his goals.

I reviewed the document carefully and could immediately see that it wasn’t designed to spell out exactly the next right thing he was to do regarding manifesting his dream job or life. It was too ambiguous, but that is actually a good thing, as many of us who are aware of hallucinating Ai know to be careful about taking career or life counseling from the chain of ones and zeros traveling at warp speed through massive data centers.

To help sharpen the focus and vision, I presented him with three questions. Assuming the AI Identity Report was fully accurate, if he were reading it as if it were about someone he knew, what recommendations/suggestions/directions would he say to them? I told him he would have to take a day or two to answer this, as it requires a bit of dissociation, to get enough distance and perspective to see himself.

I also asked how long he thought he had, time wise, to achieve/manifest the largest, “most special to you” desired aspiration.

And finally, was he willing to forfeit achieving that aspiration, or reducing the extent of it, to get and keep an intimate partner relationship?

This is an assignment that many people, whether currently employed or long out of the paycheck pursuit grind, may find of great value. It’s an effective way to check in with your core self, to consider whether the elements of “you” that have been the bedrock of your reality is truly the ideal identity for you or simply a faux.

Giselle M. Massi is the author of “We are Here for a Purpose: HOW TO FIND YOURS” and the novel “Just Dance the Steps.” Her romantasy “WYNTER’S DREAM” is now available. Giselle was a journalist with The Denver Post for 16 years and writes the newspaper advice column TELL GISELLE. Contact her at www.gisellemassi.com.