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Re-Entering the Workforce Post Divorce Part 2 of 4

Rachel Alexander Oct. 1, 2020

{5 minutes to read}  Before plunging headfirst into a job search, pause for some self-inquiry and goal setting. Like surveying a crowded room before entering, you might first step back and read the atmosphere. Rather than obfuscating or complicating this first step, I advocate for inserting a step that is both essential and conscientious — one that will make the other stairs easier to climb. Before loading the car and setting out on that cross-country road trip, one first maps the voyage and enters the destination into the GPS. That is what we will do together, here.

What is wanted in going back to work?

When approaching re-entering the world of work, one might do a self-inquiry in preparation for a session with Katherine Kirkinis, ED.M., M.A. of Wanderlust Careers, who consulted for this series. Some Wanderlust Careers-style questions might be:

  • What’s important to you — in general?

  • What are your financial needs and how immediate are they?

  • What would make you happy in the long term?

  • In what kinds of situations do you feel most at ease? Most challenged? Most fulfilled?

  • When and where have you succeeded in the past?

  • In which kinds of situations have you felt stultified, claustrophobic, overwhelmed — and why?

  • What sorts of tasks do you find fulfilling? Dull?

  • What are you willing to negotiate, and what is a deal-breaker?

  • What would your ideal work/career situation look like tomorrow? 6 months? 5 years?

  • What would you be willing and able to do in pursuit of that?

  • What do you miss about being in the workforce? What do you dread?

No Skill-Based Decisions 

Just because you can do it, doesn’t mean you should. A friend of mine has experience in accounting and bookkeeping, an employable skill, but he hates it.

Katherine and other coaches at Wanderlust Careers steer their clients away from making what they call “skill-based decisions.” A solely skill-based decision will likely not lead to long-term, sustainable work satisfaction. Given the goal is not only to get a job, but to enjoy it and to maintain it for a chosen duration, a career decision must be more comprehensively informed.

Your current skillset need not govern nor limit the jobs you pursue. Skills are gained and learned — you can add on to your skillset and use it to support the career direction you please. Furthermore, whatever skillset you currently have can likely be transferred into another career direction (e.g., a formal travel agent may have a strong set of logistical and organizational skills that could easily be applied to a variety of other positions — from operations to production).

Make a holistic career decision 


  • What environment do you like to work in? (eg. do you enjoy working alone or on a team?)

  • Do you work well when there’s noise or do you like a quiet space?

  • In which activities are you most alive? Most confident? Gratified?

  • Would you rather work from home (presuming a post-COVID-19 world)?

  • Do you prefer flexibility or do you enjoy the structure of a consistent schedule?

Answers to these questions help you make value-based decisions, in service of your life goals and your individuality.

What will really work for you, now?

How much effort are you willing — or currently able — to put into achieving the job of your dreams? For example, you may want a very well compensated position but are only willing to work 8 hours a week.

  • If prestige is important, how much effort and time are you willing to commit?

  • What is your risk tolerance versus need for a regular paycheck?

What are your current circumstances and how do they figure into your work plan?

Let’s say you have limited duration alimony for a term of four years. In that position, depending upon a slew of other factors, of course, you may have four years before you have to be fully self-supporting. That will inform your immediate options and shape your long-term plan. A term of alimony might provide the opportunity to take a lower paying position in order to gain experience in a chosen field or to focus on education to gain new skills — so that by the time alimony ends, you can garner the salary you will then require.

Conversely, if you need to be self-supporting out of the gate, the financial reality may call for a different approach. Katherine and her colleagues at Wanderlust Careers may help a client with a “dual-plan” wherein they strategize with the client to get a “stepping stone” position that allows them to earn an income immediately, while also taking actions towards long-term job satisfaction.

The next installment in this series addresses Wanderlust Careers’ Dual-Plan Approach and how it can help clients meet immediate needs while still moving towards long-term work gratification.