DEEP DIVE: The Optionality Guide to Decision-making During a Career Transition
Experts Weigh in on Optimizing for Time, Money, Happiness
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If there’s a word to describe me, decisive is not it. I rationalize this tendency by claiming I’m leaving options open, waiting to see if divine clarity will strike or if something better will present itself. And yet, the older I get the more I realize good things come to those who deliberately choose a course of action.
And when it comes to career matters, we are making choices. As of 2024, Gallup reports that over half (51%) of U.S. employees are either actively job hunting or monitoring job opportunities, a direct result of the "Great Resignation," where a large number of workers have voluntarily left their jobs in search of better pay, work-life balance, or advancement opportunities. In 2022, at the peak of this trend, about 4.5 million workers were quitting their jobs each month.
With hiring leveling off, fewer of us are opting for new full-time jobs, but more of us are choosing alternative careers. This year approximately 17% of U.S. workers reported 1099 income, up from 10.1% of workers in 2015, suggesting more freelancing, contract work, and side hustles. Career experimenting is at an all-time high.
How liberating. How inspiring. How debilitating.
Options are choices, not defaults. Keeping ALL options open can be a great way to languish.
There are some common conundrums the Optionality community grapples with:
Should I quit my job to pursue a passion project? When?
Should I switch industries?
Should I go back to school, 25 years after undergrad?
Should I adjust my lifestyle?
Should I go back to being a W2 employee?
Am I being rash, impulsive, reactionary, a fraidy cat, hormonal?
I’ve asked all of the above and reached to my personal kitchen cabinet advisory board — people whose opinions I trust and who have managed to make me think. Some have advised me directly, and some I reference regularly while pondering my next step. I’ve asked them for advice on how to make major decisions around career-impacting transitions like those above.
Laura Berman Fortgang, life coach and author of Now What?: 90 Days to a New Life Direction
Babs Rangaiah, executive coach, specializing in transitions, former media and marketing executive at Unilever, IBM, Paramount
Rishad Tobaccowala, Futurist and former media strategist, now solo practitioner and author of a Substack series on future-proofing one’s career and Rethinking Work: Seismic Changes in the Where, When, and Why (Feb 2025)
Shannon Power, a finance and operations executive specializing in growth companies, currently CFO at Scope AR.
Joanna Bloor, human potentialist, speaker, Optionality Advisor, WisdomExchange sage, and author of Tales of Potential: The Cinderella Story You Haven’t Heard
Patrice Cresci, CFP, financial advisor and principal, Team Hewins, LLC
Stephanie Agresta, communications executive, Founder and Managing Director of Ascendancy Events.
This guide is broken into three parts:
Part 1. Decision-making Pre-work: Adjusting Mindset
Part 2. Finding Your True North
Part 3. De-risking Your Transition
A resources guide is provided at the end.
Let’s dig in!
Part 1. Decision-making Pre-work: Adjusting Mindset
Prior to one of my less well-planned career transitions, I let my boredom and burnout get the best of me and left before I’d secured a role, assuming I would land something eventually. When that didn’t happen as quickly as planned I was stuck flat-footed, having to start my search from a place of having options to having to make options.
All was not lost; I consulted until I found the right fit for me, but I wouldn’t recommend quitting without, if not a confirmed job then a plan of pursuit for one.
Should I Stay or Should I Go?
We’ve all been there — so depleted in our current situation that we question whether we have enough energy to create options without getting out of our situation entirely.
“You don’t have to have it all figured out and have enough money to live on for the rest of your life, but it does take planning and careful consideration of how making a switch will impact those that depend on you,” says Laura Berman Fortgang, Career Reinvention Strategist, founder of Now What?® Coaching, and author of the book by the same name.
In my case, my biggest regret for quitting was running away from a situation without knowing where to run to, even if it wasn’t another job. If I’d had a do-over I may still have quit my job without another one lined up, but I would have already decided where to put my energy and why I was investing in myself. Says Fortgang:
"Many of us can live on less and make changes that allow us to do so. Big life changes come with a price but they are worth it if you feel like you are wasting your life away in a job or career that has run its course. If your health has been impacted by the stress of your job, you have to weigh things more quickly and heavily. No job is worth giving your life for."
So, assuming you are not in a health-threatening work situation, perhaps even enjoying your current work, but you feel in your gut that a transition is in your future, how can you explore new careers without impacting your livelihood?
The least risky way to prepare is by exploring new pathways while still in a role. In another case, when I was older and, presumably, wiser, I advised other companies, which opened me to tangential industries, business models and future roles. But there are other ways to gain new career exposure without foregoing a paycheck: Volunteering, serving on a nonprofit board or Special Interest Group at your company, joining a professional organization, investing in a skills workshop or professional development retreat, to name a few.
Or consider being partially tethered to your current company, through a fractional, consulting, or advisory arrangement. When I left the company that acquired mine, I negotiated a six-month part-time consulting engagement, working 25% time for the company, with a goal of transitioning my projects completely by the end of the term. This freed me up to advise other startups, attend conferences, and explore new industries. At other companies I’ve negotiated advisory relationships that enabled me to maintain connection with an industry, client base, equity and/or income stream while exploring new roles and building a new clientele.
When you know the What, but not the When
For executive coach Babs Rangaiah his transition took years of preparation and planning. Formerly a media and marketing executive at Unilever, IBM, and Paramount, Rangaiah started his exploration in the thick of his corporate career ten years ago, participating in a leadership program designed to help him find his "True North." After an intense week with coaches, academics, and various exercises, he discovered his purpose was to “inspire others to achieve their own greatness.”
"At the time, I was deeply focused on advancing my own career and aiming for a C-level position, so this revelation surprised me,” he says. "However, the more I reflected on it, the more it made sense. I had coached Little League, served on the board of a company that helped advance careers and found joy in inspiring and developing the people on my team and my colleagues to innovate and achieve great things.”
At the time, Rangaiah was in his mid-40s and knew that such a transition required time and a certain level of risk. He discussed the idea with his wife, who was supportive but wanted to make sure he wasn’t putting their school-age kids’ college education at risk. So he waited. Once his kids left for college he went back to school as well, earning a coaching certification at Columbia University and starting his own company, cc:babs
“I’ve been fortunate to experience some success and, more importantly, do things I love, that I’m very good at, with flexibility, on my own terms, with the gratification that comes with directly helping people with their careers and with all the income going to me instead of a company!” says Rangaiah, who specializes in coaching executives in transition.
"It’s a great place to be as I navigate the so-called 'back nine' of my career.
Coming from a place of Optionality vs desperation
How can we de-risk career transitions when we’re in a highly uncertain environment like an early-stage startup, or a heavily resourced but mercurial Big Tech? Consider your mindset while you are still in an organization. A mentally de-risking approach is what former agency executive, futurist, and author Rishad Tobaccowala describes as a company of one mindset.
"A Company of One mindset will allow one to stay longer, perform better and be happier at any company from small to midsized to giant while ensuring that one remains relevant and future proofed should one decide to move on or is at the wrong end of a “right sizing” or “delayering” initiative.
Five years after ending a 37-year full-time working career at a 100,000-plus person company, Tobaccowala suggests these practical ways of “future-proofing” while in a company:
"Invest time in learning and being exposed to the key trends in one’s field and take the time and if necessary use one’s own funds to ensure that one is using the latest tools.
Many of the latest tools are very cheap and so do not wait for a company to get them or give them. It is our job to be on the cutting edge so we are not left on the cutting floor.
Read and listen to the the best people in one’s fields. Everyone is accessible everywhere and often for free via You-Tube, podcasts, X, Tik-Tok, LinkedIn and other platforms. Professionals who are passionate about their craft can access and learn from anyone. Leverage everything the Learning and Development teams in your company provide. These are critical people. But if you need more ask for it or go get it on your own."
Too many people end up not being prepared when their company downsizes or their career stalls. They find that they do not have the skills that make them marketable and their reputation and networks are deeply limited and often over indexing in their own industry which might be in secular decline.
Do not outsource your future to your company.
When the choice is made for you
Most of us have, or will have, transition thrust upon us: A layoff, a catastrophic event, an illness, that blows up even the best-laid career plans. I recall my own explosion when it became clear to me that a role I had taken was having disastrous effects on my well-being. My instinct was to not miss a beat and start interviewing with other organizations, for roles I wasn’t even sure I wanted in the long-term. A friend, noting how unfocused and peripatetic I sounded in describing my next move implored me to stop meeting with companies until I was in a better state of mind.
"Decisions made under emotional stress tend to often be wrong,” says Tobaccowala. "So it is best to be calm or seek out people who can help one see clearly and feel calm."
Early in our careers we’re told that good things come to those who act. But only later do we realize that acting on emotional impulse can exacerbate a bad situation. A close friend of mine had a period of deep transition, including a divorce, death in her family, and extreme dissatisfaction with her job. She quit her job with no transition plan and eventually landed on her feet, but not without having to endure more disruption, isolation, and personal and financial distress.
Says Tobaccowala: "Calmness means not confusing activity with outcome and not appearing desperate. Just as banks often do not lend money to the people who most need it the likelihood of being hired when you most need a gig or appear desperate is slim since the buyer wonders what is wrong with us. So calmness is all.”
So let’s assume you are calm. How does one ultimately know they are ready to decide on a path of action?
Continue the series: