Optionality

I attended a couple of events last week, both focused on women, and was struck by two seemingly conflicting threads. At one event (Tatyana Kanzaveli's Women in GenAI event), featuring a panel of women VC partners, the investors concurred they would only invest in a company if the founders were sufficiently “committed.” Meaning, they were not building their start-up as a side hustle or while trying to hold down a “real” job that paid their bills. Of course, my immediate thought was about how unencumbered at the least and, more likely, how privileged you have to be to be able to do that. This conflation of being 100% focused and being “committed” certainly favors some demographics over others. Being “committed” doesn’t pay your rent, and it doesn’t take care of your elderly parents, and it doesn’t cover childcare, and it doesn’t provide healthcare. The second women-focused event (Elena Krasnoperova's Women of Wisdom event on portfolio careers) was populated with women who had these kind of real and costly?life?commitments. Certainly, some had nest eggs and cushions and the financial wherewithal to start something and focus on it 100%. But many did not. These were experienced women, expert multi-taskers and jugglers, and seasoned enough to feel a passion and purpose for what they were working on. The kind of women I’d bet money on, in other words. Author, entrepreneur and bookstore owner Fran Hauser was a recent guest on an?Optionality?webinar, and talked about how she gradually shifted to her new, independent portfolio career for a year while staying in a lucrative and high-level executive role…both to mitigate risk, and also to make sure she enjoyed the life she was imagining creating. This sounds eminently reasonable and smart to me. ????♀? All to say, Jory Des Jardins closed out "Pivot Month" at Optionality by posting a deep dive (link in comments) on the various advice and insights we gleaned from various experts during the month. The advice was pragmatic and focused on how to make change within the life commitments you have.

We're wrapping up Pivot Month at Optionality with a guide on -- what else? -- #careerpivots. For our guide we asked expert Pivoters on how to change things up without blowing things up. Thanks to the experts I've cited here: Alexander Shartsis, a colleague and go-to-market expert whose work supporting pivoting founders provided the ideal backdrop for anyone having to pivot quickly and effectively. Fran Hauser, former media executive, whose pivots to investor, author, and bookstore owner are as inspiring as they are instructive. She provided super-actionable advice in our February webinar on structuring a pivot while still in a role. Susan Mernit, whose transition from tech exec to nonprofit exec to AI consultant to nonprofits was equally instructive. Susan's candor on #ageism in #tech and #media, and her decision to come out of retirement but work strategically was inspiring. Delida Costin who offered up her strategy toward pivoting away from a career that was comfortable but unfulfilling to one where she made her mark on the world of high growth startups. And how she thinks of her new pivot, supporting high-potential in-house lawyers who want to have impact. Betsy Tong, whose recent guide for Optionality, Automating the Portfolio of You, was a crowd-pleaser and enables next best steps. The guide is available to our premium members, hope you will consider joining us and accessing this wisdom, as well has connecting directly with other members where we workshop career options, connect each other with resources and de-risk your exploration into new careers.

Optionality advisor Susan Mernit is hosting a free workshop for non-profits to show them how they can use AI to streamline and enhance their operations. Her approach of tackling one common task for non-profits (creating an Acceptable Use policy) takes this from a general guidance and advice webinar to, instead, a practical and tactical hands-on workshop that shows you by letting you DO a thing. Sounds brilliant to us!

I’m Great—So Why Isn’t Anyone Calling? Find out how I used AI to open doors I never thought possible. Click on the link in comments to Optionality's Substack for the article. Every job I ever had was handed to me. I didn’t pitch. I didn’t post. I was picked—because my work spoke for itself. Until I left corporate. And the phone stopped ringing. I thought: Surely, they’ll call. They know I’m great. But the world doesn’t work like that anymore. The people getting hired, booked, and paid? They know how to make their value visible. I had to learn that the hard way. Click the link in comments. Join the discussion at Optionality.

?? Thinking about a career pivot? Let’s talk about it! ?? Excited to be speaking alongside the amazing Fran Hauser in Optionality s February Member Webinar: The Pathways to Big Pivots on Wednesday, February 19, at 11:30 AM PT / 2:30 PM ET. Pivoting can be exhilarating—and daunting. Whether you’re dreaming of opening a bookstore like Fran or redefining your work after a “retirement” like I did, big career changes come with questions: ? What triggers a career pivot? ? How do you navigate uncertainty? ? What are the practical steps—money, healthcare, positioning your skills? Fran and I will share into our experiences, talk about lessons learned and strategies for decision-making, and how to stay grounded through change. ?? Join us live to ask your pivot questions! If you can’t make it, register to receive the recording. Register here, and feel free to share this with someone considering a big career shift. https://lnkd.in/g4Sn9MSE? #CareerPivot,? #BigMoves,? #NonprofitLeadership,? #Entrepreneurship.? #Webinar, #LifelongLearning,? #Optionality

Our theme this month is Pivots, so we're going to set the table by sharing some pivots from our lives, and how they got us to where we are today (bumps in the road, and all). Join us live at 1PM PT Thursday.

Our first #Conversationality in 2025 was delayed by something so 2020...a bout of COVID. So we've rescheduled our overview: What were our biggest learnings and epiphanies coming out of 2024? What are the new habits and new directions we want to integrate into 2025? Both individually and for Optionality. Join us live via LinkedIn Live, and all Optionality members get the recording afterwards. (https://optionality.life)

Our first #Conversationality in 2025 is going to be a bit of an overview. What were our biggest learnings and epiphanies coming out of 2024? What are the new habits and new directions we want to integrate into 2025? Both individually and for Optionality. Join us live via LinkedIn Live, and all Optionality members get the recording afterwards. (https://optionality.life)

Last Optionality open thread of the year: What's your no-fail trick to lifting yourself out of a seasonal slump, even just a little bit or temporarily? Click the link in the comments to share your tips with the Optionality community, or just share here in comments for ME!!!

FACING UNCERTAINTY? BE PREPARED! Advisor and investor Jennifer Coogan will break down the essentials to pack in your career "go-bag." Whether you’re striking out for greener pastures, feel at risk of being put out to pasture, or just want to ease anxiety, Jenny will issue you marching orders to feel well-equipped for an uncertain career future.