Family Vacations and the Hollywood Writers Strike

How has your summer gone so far? 

I just sweated through four weeks, two countries, six cities, a handful of mostly uninspiring hotels (beige as far as the eye can see), 13 college visits, family reunions and more fast food than I ever thought I would eat. 

(no, chicken fingers covered in crushed Doritos do not taste as good as they look on the poster). 

So, move over George Clooney and the Hollywood Writers Strike, I’m jiving to do my own strike against the thankless role as volunteered family vacation planner. 

Part of the problem? High expectations, fueled via social media, which my friend Katherine Goldstein exposes in The Case Against Family Vacations. 

The other issue?

Well, let me ask you a question. 

Do you go into time off with an intense desire to make the most of in person time together and create meaningful experiences that can cement a sense of togetherness?

Yup. Me too! Summer vacations are the one and only opportunity for everything to gel, buoyed on sunbeams and rainbows! No pressure 😳

If that fails, I will revisionist history the crap out of it by doing a summer holiday book where only the best photos and memories get in, with happy stamps of dripping ice cream and watermelons, printed on glossy pages!

I tell the kids it’s so that they can remember what their cousins look like. But really, it’s cheaper than going to my therapist.

So, did you get a weird echoey twinge of, “why does that sound so familiar?”

If so, you may be foisting the same deranged perfectionistic striving on to your teams or workplaces in an age of hybrid work. 

(shiny faces in a brochure ain’t that far away from my happy summer photo book, folks)

Today is my first day “back at the office”. 

(Read: my laptop on my own desk instead of a hotel desk, train table or balanced on my lap in my sister-in-law’s Osim massage chair - not great for webinars, btw). 

What do I see in my inbox?

• “We’re just not getting the engagement from our teams we know we could. Can you help?”
• “With hybrid, we need to reimagine how we spend our in-person time vs asynchronous”
• “We want to create meaningful experiences that can support our culture and values as an organization”

My immediate reaction was a deep sense of empathy. 

I poured myself a 5 a.m. cup of coffee, thanking jet lag for the quiet of the house and thought about this desire for in-person connection we have that keeps turning out like a bad date.

Maybe some of my summer-vacation reflection thoughts can help you at work:

1. It’s not about you (or me) 

If I’m honest, my aspirations for engagement, interaction and togetherness were more about me feeling like everyone was engaged with, yes, me, and less about empowering the “team”. 

When I thought about it from the perspective of my family, we each had exceptional opportunities to connect to our network of extended family, friends and colleagues. My kids spent way more time with each other than they do at home, more time with their cousins and extended family. 

The opportunity to weave a larger network of support beyond the “core team” can amplify and supercharge our abilities and help everyone to flourish. If I’m not available, they have tons of people who support them.

Ask yourself if you’re measuring engagement by your own self-oriented metrics. Consider planning some time for your team to be together on their own without you. Engage with the wider world through community service, sports teams or planning a client event, rather than a forcing engagement around the conference table. 

2. You can’t plan serendipity

Some say that the harder you work, the luckier you get. Even last month’s Future Proof Masterclass on networking talked about showing up to connect. 

Hybrid is an opportunity to grant flexibility by more carefully designing when we come together in person, when we work alone, and how we connect in between. 

In an age of hybrid work and more limited time in the office, it can be tempting to supercharge that together time by scheduling it to death, striving to wring every last drop of collaborative effort from the time or requiring specific outputs from each hour spent in the office to make it justified.

The in-person time we had on our holiday that worked was often serendipitous, based on just being around each other. In fact, probably the most memorable moment was during a planning disaster. Realizing we had gotten the time of our show wrong, we all bolted out of Sichuan Gourmet and ran - the dozen of us - through the streets, zig zagging around tourists and performers on stilts. Anyone can see a Broadway show. Not every family can claim to have done a flash mob in Times Square. 

Teams are the same. Allow and hold space for magical moments, quiet conversation or other serendipitous connections to happen. Create the conditions for good things to happen.

3. Values are created from being together

Most of the time, the leader decides the values and tries to craft a journey of…indoctrination is perhaps too strong a word for it but not by much!

I expected we would go to the Metropolitan Museum, a favorite haunt of mine in my 20s when I made almost no money and my parents gave me a membership. My kids thought that Midtown Comics and an afternoon at the hotel watching Glee sounded better. 

Things worked best when we recognized that time was best spent finding the overlap of our Venn diagram of values and preferences rather than feeling disappointed in each other.

We all love food, so our time at Chelsea Market, walking the Highline and seeing New York from the top of The Edge was an example of great memories made. 

You may not be able to let your team at work be quite so individualistic - after all working together is part of why you have an organization at all. But some leaders who talk about things not working are investing less in creating a shared set of values than in trying to convince the rest of the office that their way is right. 

What would happen if you invested in time together to collectively create the best possible environment for the outcomes you want.

What insights is summer giving you about your work?

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