I have been trying to find a broader context for making career and life choices.

I am 58, so a lot of advice I hear is for a younger age group. I have been journaling, but not regularly. So my challenge or ‘problem’ is how can I evaluate my career situation and make decisions around that?

-Mark

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Hey Mark-

One of the more effective methods for conducting this sort of self-assessment is to give oneself the opportunity to step back, look at the big picture, and evaluate that larger context from an arm’s-length away, rather than from right in the midst of it.

The key benefit of this approach is that it grants you a little breathing room and separates you from the day-to-day concerns that might otherwise keep you distracted from or blind to what have become latent elements of your lifestyle.

It also also helps you to more clearly see the forest, rather than just the bark-patterns on the trees. It’s easy, if you’re not careful, to become so engrossed in those patterns that you never pause to ask yourself how you got there, where else you might go, and what else you might look at.

In practice, this may mean setting aside a weekend—yes, a whole weekend—to do nothing but think.

Sit with yourself, do nothing, stare at the wall, and allow your mind to wander where it will.

Allow yourself to mentally scroll through your worries and concerns, to flag them and understand them. Give yourself permission to think about what makes you happy, what fulfills you, what helps you feel productive and challenged and growth-oriented, and also what feels limiting and stressful and draining.

Consider each and every aspect of your life, from work to relationships to hobbies to diet, and ask yourself how you might tweak that network of behaviors and routines, make changes to it, so that you have more of the things that fulfill you and fewer of the things that deplete you.

One advantage of this approach is that it can help you understand how the pieces of your life fit together holistically—in the sense of every aspect of your life being connected to every other aspect of your life—while also providing you with insight into what you might do about these realizations.

More specific to work and career, think about how you want to spend your time each day, what types of work you feel comfortable putting out into the world, and what value you might add to the lives of others.

It’s remarkable how much more balanced life can feel if the work you do is structurally aligned with your beliefs and priorities.

Many of us spend vast quantities of time and money simply trying to put the pieces back together each night and weekend, subconsciously struggling to justify the energy and effort we’ve expended on work we don’t particularly care about, often through thoughtless consumption or other net-negative rituals.

A primary focus of this exercise should be making sure that you don’t accidentally rebuild your career and lifestyle and relationships, only to find that you’ve recalibrated in a direction that doesn’t actually serve you and your priorities.

As you look at your life in its totality, consider what you might do that both allows you to pay the bills, and feels right according to your own, personal moral standards. Even better is if you can identify some kind of work that challenges you and helps you grow, rather than incentivizing you to plateau as a person.

We’re often encouraged to pursue metrics of success that are not our own, and though it’s still not an absolutely certain and foolproof thing, stepping back and assessing the big picture in this way can help you figure out which measures are the right ones for you and what you want as a complex, unique individual.