Upgrade your OS this year. (And every year.)

From software, we have the idea of periodic updates to our devices’ operating system (OS). Every so often, maybe weekly (or monthly if you're me), you need to shut down your device, reboot and install updates that include new features, bug fixes and security patches.?

Why? Because the world changes.?

We need to periodically update our operating systems.

In adulthood, I’ve realized I need to do this too.?

On a personal level, I go on silent retreats each quarter to literally shut off my phone, be still, reflect and set goals for the next quarter. I started doing this when I was first leading two teams of 45+ people at age 26 and knew that if I didn’t step back and examine my life, I’d be a reactive manager to my teams, instead of being the intentional, mindful and strategic manager I knew my team needed (and I wanted to be).

That’s my version of shut down & reboot. It’s a tech detox of sorts and a way for my brain to disconnect, even if only for 36-48 hours from email, Instagram, Whatsapp and every other online social platform.

What updates are you installing?

I’m a voracious reader and love reading or taking classes to learn new skills, which is my version of “new features” to my operating system. My favorite books of 2022 will have to be a separate post, but in 2022, I took two classes: 10 weeks of online improv classes from Second City (inspired by a LinkedIn post from my brilliant friend, Michelle Vitus, CEO of Slate Advisors, which helps companies with personalized, value-driven career coaching) and a week of culinary classes at the Culinary Institute of America!

If you’re new to improv, or improvisational comedy, it’s a form of unscripted and unplanned comedy that’s produced comedy legends like Stephen Colbert, Tina Fey, Steve Carrell and the entire cast of SNL over the years.?

If you’re someone who struggles with perfectionism or anxiety, if you’ve gotten feedback that you’re “too polished" or "not relatable", or if you’re someone who is just looking for a non-addictive endorphin high, you should take improv classes. Each course was 3 hours one night a week for 5 weeks, and I laughed SO MUCH. There’s no homework, there’s nothing to lose and it’s one of the best dollar value investments I’ve ever made.?

I’ll do a separate post on the role of comedy/humor in my life, but this was life-changing.?

And that’s the point - you don’t know if a new skill or hobby will be life-changing until you try it!? And there’s so many cool skills and classes available online. And if you try one new class a year for the next decade, that’s 10 more skills you’ll never have tried otherwise - and may find something you’ll love getting better and better at for the next decade. (Worst case, you’ll have funny stories to tell about something you’re terrible at - like the time I tried Argentinean Tango…)

So what are “bug fixes” in this metaphor?

“Bug fixes” take the form of feedback from trusted friends and longtime mentors that I integrate into how I view the world and how I view myself. ?

At Stanford’s Graduate School of Business, there’s a deep value for receiving and giving feedback.? It’s almost a joke but the longer I live, the more I see that genuine feedback is a rarity.? Most people don’t have the courage - or the emotional skill - or don’t value the relationship enough to say the hard things with kindness, candor, and without ego.?

There’s the self we know (ie: the faults and talents we’re self-aware about) and then there’s the self we don’t know because we can’t see ourselves clearly.? And that’s where feedback, friends and mentors come in.? They see our blind spots, they see our best (and worst selves), they see our struggles and the places where we glide effortlessly without realizing that this magical thing we do is often hard for others.??

So in 2022, I formed a personal advisory council, drawing inspiration from the Lightmaker’s Manifesto, a course I took with IINDIVIDUAL.CO, and from collectivist cultures where we invite the collective wisdom from our elders and communities into our decision-making process. I run our hourlong session like a board meeting: updates from the last quarter, goals for the next quarter, progress on key metrics and the big questions that I want my advisors’ perspective and experience to weigh in on.?

In my most recent advisory council, as one of the key metrics, I shared my burn rate -? the amount of money I’ve spent to date on sabbatical, as a percentage of the total amount I planned to spend, feeling a mix of emotions when I flashed that number on screen: embarrassment, guilt, anxiety, vulnerability. Spending money is something fraught for me, given the life experience of my parents who were frugal to a fault in their struggle to survive as first generation immigrants.

And one of the wise members of my council, who has a decade or two of more life experience than me said to me, “The money will figure itself out; time is the thing you’ll have less and less of.” And I felt a wave of relief, needing to hear this from someone who knew me deeply but wasn’t my peer or my family.?

The advisory council doesn't have the answers to life’s big questions (only you can figure those out for yourself!) but these wise friends and mentors ask valuable questions, impart wisdom, and hold up the figurative mirror to me and help me figure out what matters to me and why.?

My invitation to you

In 2023, we’re past the pandemic but it has had a significant toll on everyone.? We’re less social, we’re more anxious, we’ve built up “muscles” that should atrophy (read: our addiction to social media and fear/uncertainty/doubt/outrage) and we need to build up skills that’ll help us be the people we want to be (intentional, proactive, values-driven, and gratitude-grounded).

This year, I hope you’ll take time to do for yourself each one of the three things we do every day (or week or month) for our laptops: 1) Turn off & reboot, 2) update our OS with new features and 3) install bug fixes.

Subscribe to my mailing list if you’d like to learn more about silent retreats & tech detoxing, and if you’re looking to learn a new skill (like giving feedback!), take my class on mindful management I’m teaching for Stanford’s Continuing Studies program where I'll be sharing some of the best frameworks, tools and best practices from the fields of cognitive neuroscience, psychology, communication & conflict mediation, so that we can have better conflict and better communication at work.

And if you’re enjoying my writing, you can follow along on substack, where I post my musings (that I sometimes turn into longer articles like these) or on Medium, where I post my longform autobiographical essays on identity & culture.?

However you’re starting 2023, I invite you to turn off, reboot, & update yourself this year.

Not because you’re not good enough - but because the world continues to change.

And we need to evolve with it.?

Tiffany Teng is a product & go-to-market fintech executive whose experience spans D2C & SaaS, startup & Fortune 50 in both the US and UK. While on sabbatical, she teaches, advises, coaches and writes on business, psychology, identity & management. Reach out at hello @ tiffanyteng.com.