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(This article was reprinted from Optionality, a community for employees, employers, transitioning workers, consultants, entrepreneurs, service providers, really anyone who is committed to exploring a future of work that works for everyone.)

A few years ago my sister did the unexpected. She joined a Big Tech company.

A 20-plus-year career academic, my sister was accustomed to preparing lectures, grading papers, and working on independent publishing projects. Now she was embedded on a team deliberately composed of “non-tech” expats from military, criminal justice, and other academic backgrounds to work on a stealth project that leveraged her deep researching skills.?

I was both pleasantly surprised and worried about my sister’s new job: surprised because I knew how hard it was for many with tech experience to land roles in this company and here she was, a history professor, hired to work on a high-profile, stealth project, for the very skills she’d developed over years; and worried because of the severe culture shock I anticipated she’d experience.?

You see, my sister had never worked a “Nine-to-Five” with KPIs, a set work schedule, or a company-issued laptop.

She’d written several books, delivered thousands of lectures and was used to working long hours with stringent deadlines, but she often worked independently, on her own schedule. Now she had back-to-back meetings, internal clients, a fob.

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A few weeks into the role she reported what she liked perhaps the most about the role: Her colleagues. She was in the beginning stages of a long, disorienting, sometimes isolating divorce and her co-workers, some literally half her age, took her under their wing, inviting her to lunch every day or out for drinks after work. She joined them when she could but most nights she needed to get home to make dinner for her kids.?

“I feel like I’m back in college!” she laughed, and not just because her colleagues reminded her of her former students. Everything, from setting up her laptop to taking the campus bus required new learning – an entirely new way of working.

I knew how different this role was from anything she had ever done before. I was proud of her.

But I could also sense the beginning of the end of her short tenure at this company.?

One night during our then-nightly check-in she told me she had to get to the office at some ungodly hour the next day to finish some work.?

I asked her why she didn't just finish her work that night so she could be done with it. And she responded: “Because my computer is at the office.”?

I was confused. “Don’t you have a laptop?”

“Yeah.”

“Why didn’t you bring it home?”

“Why would I do that? I’m done working for the day.”?

I thought back to the last time I’d kept my laptop at the office: It was 2001 and it was what would pass for a desktop today. That was, perhaps, the last year I’d had work boundaries.

I implored her to please, PLEASE bring her laptop home with her next time, not just to prevent her from having to go to the office early to finish her work on time, but to keep her job.?

“Yeah, I don’t think so,” she said. “I want to keep my work and home life separate.”?

In contrast I was at the time holding a leadership role at another Big Tech, clocking a standard twelve every work day, not counting weekends and travel, working from my phone and laptop at home, from airports, my daughter’s weekend gymnastics practices. Part of me admired my sister for holding so steadfastly to boundaries, and part of me wanted to shake into her the reality of knowledge work in the 21st century.?

We don’t clock in and out, Sweetie. We stay on the clock, or at the very least we appear always-on, as table stakes. To do anything less means you aren’t serious.

Not surprisingly my sister ended up leaving her job, by her choice; she didn’t feel there was a fit culturally. I wish I could end this story with, “and from then on, she worked on her own projects, on her own schedule, and worked happily ever after,” but that wouldn’t be true.

My sister did take other roles that played to her strengths of researching, presenting, writing, and educating people, but that also carried updated expectations of productivity.?

• She had to learn to have a device on her at all times, should her boss need to reach her while at Pilates. Harder still, she had to remember to check it.

• During COVID lockdowns she mastered presenting webinars from her home office by doing so hundreds of times to audiences domestic and abroad, and even troubleshooting when she lost connectivity at 4 a.m. in the morning.

• She learned the practice of “Slack hygiene” -- keeping notifications current, sending short missives from her phone, integrating with other applications, checking it regularly and responding to others, even while engaged in a meeting.

She’s asked me for advice on managing the dichotomy between critical thinking and the productivity skills that are meant to enable it. I’ve been working this way far longer than she has; I must have some hacks, right?

Sadly I don’t.

• I still keep too many browser tabs open, afraid if I close them I’ll never get back to that article, until eventually I have to reboot my computer.

• I sometimes forget if I’m in Zoom, Teams, or Google Meet. I need a minute to figure out what system to use, for which situation, depending on who I’m talking with. And I need two minutes to remember how to share my screen in that respective application.

• For non-work-related channels Slack has replaced email as a parking spot for the not-too-urgent.?I feel slightly threatened by seemingly innocuous statements like, “did you see my Slack?” because if you are asking I likely didn’t, and it suggests I was supposed to be monitoring it rather than focusing on what I’m actually doing.

• I accept I will likely never actively read, sort, or deal with the 24,901 unread emails in my Gmail account.

• I don’t see all of my texts, or clear them out. I stopped trying to unsubscribe from the political ones.

• I don’t start projects using AI. I start with what I want to say and then validate it on Chat GPT.

• I still take hand-written notes, in cursive, even when meetings are backed up with an AI notetaker.?

Some would say I am unproductive, resisting the inevitable future of work. I would say I’m still finding that place where I net out positive on work I want to do over work done solely to appear productive. Isn’t that the true end game?

The Optionality Guide to Decision-making During a Career Transition

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 (available in full on Optionality)

Part 2. Finding Your True North (available to Premium members; register on Optionality)

Part 3. De-risking Your Transition (available to Premium members; register on Optionality)

Jory Des Jardins is a fractional executive, startup advisor, and startup founder who has worked with B2B, B2C, and B2B2C companies on go-to-market, scale, and exit strategy. She co-founded BlogHer, a startup that achieved category-leading scale and was acquired in 2014, and is co-founder of Optionality, a community of practice for independent workers, giving structure to alternatives to the single-path career existence.