New writing: "Me Time"

Sailing Through Last Year

January 9th, 2021

Kai, Kevin, and Bailey in front of a garage door in Japan

People & Company team retreat in Osaka, January 2020

My friend Gary Chou shared with me that “climbing the ladder” is a faulty analogy for navigating a career. What’s a better analogy? Sailing.

Caveat: I’ve never sailed 😬. But… making decisions about work and in my case building a small biz has felt akin to what I imagine it’s like to sail open waters. You develop a sense of where you’re headed. The seas change. Winds pick up in certain directions. You adjust, and do so continually.

2020 felt like sailing unpredictable waters with my team in separate boats. We clung to out-of-reach destinations, recruited new crew mates and savored both painful and beautiful days along the way.

Changing Winds

The partners at People & Company, Kai, Bailey and I, met up in Osaka at the start of 2020 to lay out our “WOOP”: the Wishes, Outcomes, Obstacles and Plans for the year. The north star that emerged was to “Build the business.”

We were on the heels of publishing Get Together.  There was an uptick in inbound interest for our community strategy sprints and labs. Bailey and I moved into a new Chinatown office. And, we set the clearest goals in our partnership’s short history around revenue and book sales.

A few weeks later, we were wrapping two days of client strategy sessions in NYC as COVID swelled. I remember asking myself, “Is this one of the last times for awhile that we’re gonna work like this? In-person, in the same room… Is how we work about to change?”

Alongside the majority of people on planet Earth, our daily lives did change. From a business standpoint, the hardest part wasn’t adjusting our approach with clients or going virtual as a team. The hardest part was letting go of those goals we set together in Japan.

We had the privilege last year of working with clients across sectors and around the world—each connecting people in innovative ways. From government partners like GIC (Singapore’s sovereign fund) and Export Development Canada to startups like Substack and Special X to nonprofits like Future Now and the Surfrider Foundation. We offered guidance and facilitated finding clarity.

But as Bailey put it at our EOY retro:

“We had set a bar for success. People & Company had a revenue goal. For the first time in awhile! And like two Straight-A students, Kevin and I drowned ourselves trying to reach that bar.”

As it became clear we would fall short on our revenue goals we took it as failure, even during this pandemic. We didn’t stop to ask, “Are those goals the right goals right now? Do they need to change? Do they capture what we’re really after?”

It’s taken time and a reframe to say that we are proud of last year—the 2020 iteration of P&C. We made six-figure revenue. We sold almost 5,000 books. We worked with 30+ clients in different capacities. We are in business and grateful to remain partners.

Writing now, my toxic stubbornness around our goals feels silly. But sometimes we fall in love with destinations. And it’s hard to acknowledge that perhaps we need to change course or stop off to resupply along the way.

Taking Care of the Crew

Like countless others, our team canceled plans, postponed weddings, kept distance from family and friends, and grieved lost loved ones. These were heavy moments. I personally hit a wall—feeling roasted by the time we reached Thanksgiving.

Screenshots from Zoom meetings

A year in Zoom

We also experienced joy. We jumped rope, made food, welcomed new family members into the world, settled into new homes, and connected with new communities.

The number one rule at People & Company is this: “We are people first.” I wrote two years ago: “Our personal wellbeing and the wellbeing of those we care about is more important than this company.”

Today, I’d remix that statement to say, “Our personal wellbeing and the wellbeing of those we care about fuels this company.” At least at our scale, People & Company grinds to a halt when our batteries are low. And doing our best to take care of each other, draft off of one another, and not only recharge but also maintain reserves is essential for whatever we do next.

This ship is nothing without its crew.

Adding crew mates

One of the goals we did achieve was to have more humans at our 2020 holiday party. For all of the different organizations we’ve gotten to work with, our team remained tiny leading up to last year. The 2019 P&C holiday party involved Kevin and Bailey sending a selfie to Kai from a two-person booth at a sushi restaurant.

Our thesis is to build *with* people. Those progressive acts of partnerships enable us to make a bigger impact with a community and often lead to a more fulfilling personal experience. So this year, P&C practiced what we preach. We built *with* more people. We brought on a dozen+ contractors, launched our podcast correspondent program (shoutout to Mia, Maggie, Marjorie and Whitney!), invited pod listeners behind the scenes, signed on new vendors, and even hired our first part-time employee (sup, Katie).

Bringing more people into People & Company became one of the most purposeful aspects of work last year. I felt physically isolated. During a nine-month stretch, I saw Bailey in-person twice and Kai zero times. Not once did I see my immediate family.

But I collaborated with more people this past year than the prior three years with P&C. And at a time where a lot of companies tightened budgets, it felt defiant to compensate more freelancers with more money than we ever have.

I’m proud of that. Paying people to do work they want to do at rates they’re happy with is rad. Especially, at this time. Hiring folks is a fulfilling aspect of navigating the small biz world and part of why we set the revenue goals we did.

We may set sail for a certain destination but the crew is what determines whether we enjoy the journey.

In my experience, building a business hasn’t been a linear path or even a winding one. There’s more uncertainty. It takes navigating unknowns and responding to forces at play.

Sailing through 2020 was a next level course for me in navigating change. Setting and sticking to an initial direction, even if you expect to iterate, sometimes just doesn’t work. We learned that for ourselves and in our work with our clients

In facing such uncertainty, we were reminded how much your crew matters. So this coming year we’re remixing how we partner with individuals and teams. The most valuable service we can offer is being a consistent, long-term partner—spending time with leaders over time, not merely dropping in for intensive moments. (More on that soon.) But if you’d like to partner with us in 2021, you can expect us to go deeper together than one-offs. And know that, as a crew mate, we will expect your attendance at our 2021 holiday party.

For myself, my team, you and the communities you care about, I wish you a safe passage and a supportive crew along your own journey this coming year.

Tagged: Entrepreneurship, People & Company, Small Business