Reading: Going ahead with Your Reinvention — Even in a Bad Economy

I am a new and reluctant empty-nester eager to explore the so-called “benefits” of my newfound (but not sought) freedom. So, in February 2020, before airplanes were grounded and “social” and “distancing” were conjoined,  I decided to take advantage of a business trip to California by tacking two extra days on the front end to putz around San Francisco. 

“Putzing” is new to my lexicon. In the past, there was simply none of it. Instead, I would skid into an event with seconds to spare and take the red-eye home afterward so as not to miss a family dinner or one of my four kids’ games.

On day three of my trip, I boarded a train to San Jose for the Watermark Silicon Valley Conference for Women to deliver a talk and moderate a panel of experts on the topic of Comeback Careers. My audience was women on the precipice of work-life transition: moms who took career breaks and want to return; middle managers looking ahead to reinvention in the second half of life; retirees who “aren’t done yet.”

This is a topic I know well. I’ve consulted, coached, and keynoted my way around it for the better part of two decades. As a returner who took a career break to raise my children and, more recently, as an entrepreneur who launched a new company at 55, I’ve lived it.

So there I was on the train, organizing my thoughts, considering which of the many inspiring career comeback stories in my arsenal I would tell when I was distracted by an incessant squeaking sound over my shoulder. I turned around to see two women: one of them, my age-ish, inflating and twisting elaborate balloon animals; and the other, twentysomething, sporting a large pair of furry pink mouse ears, watching. As we reached our common stop, I made small talk with the balloon artist in front of the train doors. 

“I worked in Finance for years, in Chicago, before we moved here to San Francisco,” she explained. “After the move, I took a career break to be home with my kids. I always thought I’d return to Finance but, instead, I’m doing this,” she continued, smiling and gesturing with her head toward the overflowing Hefty bags of colorful, inflated animals she dragged behind her.

Turns out, when she weighed her options of returning to the investment world or committing to her creative side hustle (kids’ parties), the latter won out.

Many factors influence our comeback career decisions. Money is the most influential of them— particularly now, as social distancing measures temporarily shut down the global economy. Financial confidence has been replaced with worry about family income stability, job security, benefits eligibility, and shrinking investment portfolios. Accordingly, I predict that we’ll see a surge of MBA-Moms returning to work, underpaid managers looking to pivot, and seasoned execs coming out of retirement, post-pandemic.

But my new San Francisco acquaintance had done very well during her work years and was married to a husband who made a good living; earning money was not her top priority, and probably isn’t still. 

With few financial demands, she could afford to be highly selective about her next chapter. I assumed she must really love entertaining at kids’ parties to have chosen balloon art as a career but, like so many stories, there was more to hers.

Her assistant (the young woman wearing the mouse ears) was the balloon artist’s learning-disabled daughter. When calculating her comeback career options, mom factored her daughter into the equation: As the parent of an adult child with few skills and fewer opportunities, wouldn’t it be great if she could find or create work that would meaningfully employ her daughter, too?

Watching the mother-daughter team step off the train, their colorful animal menagerie in tow, my heart was full — of admiration for mom’s loving, selfless decision, and of joy for the daughter who has a life of purpose because of her. I also felt a sense of validation for the work that my partner, Kelley, and I do every day. Some might call it “fluff,” but we spend hours doing the important work of digging deep to understand the client’s or student’s “why?” of relaunching her career or pivoting into a new one.

Of course,  if you are looking to make money now, the “do what you love and the money will follow” mantra won’t likely cut it for you. You may have to land work in a field where you are most skilled, and can command the best pay — and perhaps pursue yoga certification as a side gig.

Many of the women I’ve helped through private coaching, workshops, and my company’s courses — especially now — have a financial imperative for returning to work or making a career pivot. Oddly enough, a global health and economic crisis is a great career change motivator — a time to rethink common, pressing expenses like college, retirement, debt, and elder care. 

Understanding your values, motivations, and priorities (your why) for reentering work or making a career change matters more now than ever; it’s as important as understanding your strengths, skills, and experience (your what). If you are planning your next chapter, or being thrust into one due to current events, here are a few questions to get yourself thinking about and understanding your why:

1. What do you value most in your personal life and in the workplace?
   Examples: family, stability, flexibility, challenge, connection, recognition, status

2. What is motivating you to initiate your career comeback or pivot now?
   Examples: financial loss due to COVID-19, change in marital status, looming college expenses, desire for discretionary income, unplanned expenses, emptying “nest”

3. What are your top priorities for the new career you are pursuing?
   Examples: money, benefits, flexible hours, title, responsibilities, creative control, proximity to home

You may have a long list of factors or, like the balloon artist, you may have one that trumps all others. Find out what it really is by taking the time to ask yourself these questions. Answer them thoughtfully and honestly, and then be vigilant about finding or creating work that fulfills your why — be it crunching numbers, writing copy, or inflating and twisting balloons on the CalTrain. 

Covey Club Member Susan Rietano Davey is cofounder/owner of Prepare to Launch, LLC, a learning company that guides women through important work-life transitions. Through their Prepare to Launch U-branded courses, including their signature Career Relaunch Course, Susan and her partner, Kelley Biskupiak, help women find professional success and personal fulfillment along the continuum of work and life.