Dispatch - Q2 2023

Dispatch - Q2 2023

Ditch the ladder, climb the mountain

How to reject the on/off binary of work with a more holistic approach

Hello! And welcome to the Gather Dispatch, our quarterly report on the current and future state of work. You’re used to hearing stories from me, Cole Stryker. For International Women’s Month, we’re doing something a little different. It’s my pleasure to introduce freshly-minted Gatherer Amber Stryker, my brilliant wife, who recently took a leap of faith into the world of independent knowledge work. She’s taking the reins for this issue of the Dispatch, and we’ll hear her personal story, and those of a few other Gather women who’ve found empowerment in independent knowledge work. Take it away, Amber!

Stepping off the corporate ladder

Four years ago, I was working a full-time job at a blue chip firm. Every day, I would drag myself out of bed, kiss my husband and baby goodbye, and lug my pumping gear to work. This company’s parental leave policy and accommodations for breastfeeding parents were decent, but even still, it was a challenge to get through each day. I was always tired, and when the nanny is texting you that the baby has taken her first steps, the well-stocked office snack room is a cold comfort. 

It was then that I began to ask myself, “What am I doing? Is this worth it?” But my career was and is important to me. I love what I do for a living, and I felt compelled to pursue it and my duties as a mom with the same level of passion.

On paper, my career was exactly where I wanted it to be. I’d spent the previous decade working with global entertainment and beauty brands. I’d created nonprofit partnerships and helped run cause-marketing campaigns for top-tier talent like Lady Gaga, Nicki Minaj, Rihanna, Miley Cyrus, and Ariana Grande. I had the opportunity to help manage multi-million dollar giving programs and developed ambitious sustainability goals that would have a measurable impact on our environment. All the while I had a front-row seat to the formalization of social good programming into the exciting new field of ESG. I was there from the beginning, and my career path enabled me to authentically position myself as an experienced leader in the space.

When the pandemic hit, I went from five days in the office to zero. The lockdown was no picnic for working moms, but for me, there was a bold silver lining. I got to work from home, spend more time with the baby, and prepare for another one on the way. It was a lot easier to deal with the nausea, exhaustion, and other indignities of pregnancy in the comfort and privacy of home.

When my second baby arrived, I knew — pandemic or no — that I would never spend another day commuting and working for ten hours. I recognize that this line in the sand is born of privilege, and that many parents don’t have the luxury of choice. But I did, and I took the chance to work remotely full time. I was excited to balance my career with proximity to my kids throughout the day, while my nanny cared for them. Here was an opportunity to “have it all,” so to speak.

But even when working from home, I still wasn’t as available to my kids as I wanted to be. I was stuck on Zoom calls, shutting them out of my home office, muting my microphone and hoping that their sometimes anguished cries weren’t audible to my colleagues. Remote work was a game changer, but I wanted more control, more flexibility. I still felt like my life revolved around my work, and everything else was squeezed in wherever I could fit it. 

In mid-2022, I began thinking about the possibilities of an exit. I knew that the full time stay-at-home-mom route wasn’t for me. I really do love my work, and leaving the corporate world completely would have been a financial burden. I just wanted to shift my priorities, and a full-time job wouldn’t give me the flexibility to do that. 

My husband had been consulting on a freelance basis for most of his career, and I could see how this gave him the flexibility and freedom to spend exactly the amount of time that he wanted or needed with the kids. He watched our oldest child for her first six months during the day, after my parental leave expired. I’d get home from work, we’d make dinner, and then he’d decamp to his office to work through the evening while I handled childcare. This arrangement wasn’t always easy, but it enabled him to maintain an active status with his clients and preserve some of his income, while giving him the once-in-a-lifetime opportunity to bond with our child at a critical age. Plus, the technological shift that enabled the world to pivot to a remote-first model allowed for asynchronous collaborations, which gave him as much of a presence in the “workplace” as anyone else on the team, full-time or not.  

But there were other concerns. When you’re a married couple and one of you is independent, it’s smooth sailing. My husband and kids were always covered under my insurance. And if he ever got dropped by a client, we could rely on my steady income to float us until he picked up a new gig. Although he sometimes earned more in terms of salary, my job was always the financial “anchor” for the family. So it felt a little precarious for us both to go independent at the same time. What if we both lost a major gig? How would we pay for insurance on the open market? 

There are other apprehensions that full-timers have which I shared to one degree or another. Would my career progress decelerate? Would I have the same level of visibility with important stakeholders? Where would I be in ten years if I wasn’t able to “climb the corporate ladder” in the same way? Was I closing the door on reaching my full potential? What if I succeeded, and end up with way more work than I have now, and pressure to spend even less time with my family than I did when I was working full time?

Even though I’d never felt a strong entrepreneurial urge, my husband helped me recognize that I’d developed enough skills to offer a service to the world that would be in increasingly high demand. My community also gave me the confidence to take the plunge. I participated in a coaching group led by executive coach Lis Best, where she inspires impact leaders to rethink what ambition means for their careers and lives as a whole. Along with friends and colleagues, my community helped me understand that I would quickly be able to win business as a team of one, and eventually those accounts would need more help, and I would be able to delegate work to entire teams that I would run. 

I started my consulting business the day after New Year’s, and so far, I’m thriving. I was able to arrange to consult for my previous employer, and I picked up two other gigs supporting ESG efforts in the tech and apparel industries. I spend roughly 20 hours a week building my business, and the remaining 20 with my kids, which is a ratio that feels right, for right now. This might change. When my second kid goes off to preschool, I might pick up additional hours. Or maybe I’ll want to take a couple summer months off for a long vacation. Who knows? For the first time ever, the choice is mine.

In 1982, Cosmopolitan magazine editor Helen Gurley Brown, published a book called “Having it all: Love, Success, Sex, Money . . . Even if You’re Starting With Nothing.” The phrase, “Having it all,” became a feminist watchword for a generation of women ahead of me in the corporate world, so much so that 40 years later, it’s become sort of a cliche joke, the kind of thing women say with a wink to evoke an outdated wave of feminism overly fixated on balancing work and the rest of a woman’s life. 

It was probably as obvious then as it is now that almost nobody really gets to “have it all,” and what women — what anyone really wants is to be able to find their own balance, to chart their own course. Independent knowledge work is allowing me to do just that.

Not a pause — a pivot

I had the opportunity to be part of the most recent Gather Dispatch podcast episode, alongside Gather’s Mimi Sun Longo, Mindy Raf, and Cat Soroush. We talked about how independent knowledge work has served us as women, how going independent has inspired us to reject the on/off binary of full-time work, and how we’ve found alternatives to the “corporate ladder” mindset. 

“I think we should start with just saying there are no rules,” says Mimi. “We’re leaving the ladder. It’s all directions.” 

What Mimi meant was that the corporate ladder mentality implies a linear path, where there’s only one way to advance: straight up — or in some tragic cases — down. What going independent helped us all realize is that it’s better to think of one’s career as a non-linear, choose-your-own-adventure experience. While we struggled to come up with a good metaphor in the moment (Mindy’s image of “a million little step stools” and Cat’s of Beauty and the Beast’s Belle swinging across her library on a wheeled ladder will live rent free in my head for a while), I think a good metaphor might be a mountain with many routes to the top. 

I live in Los Angeles, and one of my favorite getaways is Yosemite National Park, which contains a mountain that draws elite climbers from around the world. Anyone who’s seen the documentary Free Solo can attest to how climbers take many approaches to ascend the daunting face of El Capitan. There are several routes of varying difficulty, many with long lateral — or even descending — stretches, which ultimately wend their way to the top. That’s how I think about work now. I am no longer in a two-dimensional space, and a choice to prioritize non-work experiences like family, community, hobbies, travel, or creative pursuits, aren’t a step backward or even standing still. They’re all moving forward, just in a different direction. It’s a holistic way of thinking about work and life, rather than a false binary of two opposing forces that one must balance.

Maybe your ambition is not conventionally oriented towards scaling as high as you can toward the C-suite. Cat brought up the idea that women often feel pressured to relentlessly pursue corporate advancement at the risk of being seen as less ambitious or plateauing or not wanting to grow. 

“Sometimes it feels like women can’t win,” she said. “There’s always comments made about how you make a decision. I have friends with kids, and I’ve watched them struggle with how to split their life, and there’s always a critique either way. If you choose to step away from your career and be a full-time mom, you’re not ambitious. If you choose to split your time, you’re not a dedicated enough parent, something’s going to be said about how you choose to spend your time. 

Maybe you actually do just want to slow down for a while? That’s not a pause or a step back, it’s a valid ambition. There can still be learning and growth even if a movement doesn’t involve a formal promotion or pay bump.

“Really I would love to see women doing exactly what they want,” said Cat. “And that might look very different for everybody. And that’s very much okay.”

Another advantage to the independent knowledge work model is that it allows you step outside of a box that you might not even realize you’re in until you’re outside of it. Mimi was working in a bakery before a big career pivot into project management. She’d been at the bakery for a while, and had the realization that the next rung “up” would have her running the bakery, a role she didn’t really want. 

“I started really thinking about what would come next. I’d heard about project management from my husband who’s in software engineering, and my brother who works in graphic design,” said Mimi. “They both thought, ‘Oh, you already do this on a much more difficult, exhausting platform. Why don’t we see if you can work in tech?’ When I moved into the corporate world, all of a sudden, the ceiling changed. I thought I’d reached the top, and now there was an extra floor of space that I could move through, rather than up and down.”

“Sometimes you get stuck thinking you have to stay in your vertical,” said Cat. “Or think that you can’t leave your industry, without realizing how transferable your skills really are, and how easily you could weave them into a different job. So many people think they can’t make a move because they’re not equipped to do it or don’t have the right experience or education or resume.”

“If you’re only in a specific environment or culture, you tend to get tunnel vision,” said Mindy. “And there are all these other worlds out there. But if you don’t know they’re there, you can’t see them as possibilities.”

“I always feel this urge to want to be involved in more and know more,” said Mimi. “And sometimes a new opportunity shows itself during an inconvenient time, and I forget that I can just say ‘No.’ And I get caught up in this overachieving mindset, wanting to commit more time to all the things I’m part of, instead of taking the moment to actually say, ‘Okay, what is my direction intentionally going to be instead of just falling up the stairs?’” 

“There’s nothing wrong with the corporate ladder, per se,” said Mindy, who spent years as a comedy writer. “I was once at a point where I’d been freelancing for so long, and I was completely burnt out — to a crisp. And I took a corporate job with a coffee break and a happy hour and someone telling me what to do. For a few years, that felt blissful. Eventually I realized it wasn’t for me, but I needed it at the time. It depends on where you’re at, and what you need. We can recognize the goodness of structure.” Mindy sees her current role as a consultant as a kind of happy medium, giving her a balance of flexibility and structure.

Mimi’s a rock star. Mindy’s a comedian. Cat paints and draws. I’m not as creative as these three, but we all have pursuits in life that bring us joy and meaning. I don’t like to think of side projects, hobbies, and extracurriculars as “side hustles” — even if we are trying to aggressively monetize our talents and passions. They’re parts of a whole, all essential to who we are as humans. 

Permissionless leadership

Mindy further noted that going independent enables women to bypass longstanding hierarchies that have favored traditionally male styles of leadership. There is a lot of data about how women get passed over for leadership roles. We’ve all heard the statistics. We know that women have to work harder for less pay, less respect, and at a slower career progression. I entered my 30s at the crest of the “Girlboss,” revolution, a time when women were expected to overachieve, to “lean in” and grab opportunities that might otherwise fall into the laps of average men. 

Some women have been socialized to expect less and think less of themselves. Forbes explains this “confidence gap”:

For example, when asked how much they agreed with the statement “I performed well on the test” on a scale of 1 to 100, the average woman ranked her performance at 46 — but the average man reported a 61. That’s a difference of one-third. And note that the women, who underestimated their performance, were closer to the truth than the men who overrated their performance.

Obviously this needs to change at a systemic level, but going independent allows women to take positions of leadership without having to ask for permission in an organizational hierarchy that may have been slanted in favor of males for many decades. 

Mimi, Mindy, and Cat have embraced permissionless leadership for a long time, and I have much to learn from them and other women who are charting their own course. This year, I’m embracing permissionless leadership for my family, for my career — for me.

Trust but verify

Of course, all the ink in the world can’t print a contract that’s air-tight enough to ensure real trust. If a boss or a worker wants to screw you, they can often find a way to do it even when decent contracts are in place. Nobody wants to go to court over a few paychecks, so how do you safeguard yourself as a worker or as a boss? If at all possible, you’ve got to try to work with people you know and trust. 

We spoke with Christopher Kienle, who currently serves as a VP at a national insurance firm. Christopher is a repeat Gather client, who has hired and embedded Gather teams within 4 organizations over the last 6 years. He keeps coming back for more because he’s developed an unparalleled level of trust with Gather as a brand. Trust is so important to Kienle that he puts comparatively less stock in contracts.

“Gather is the only company I’ve trusted over the years to put together contracts with lesser-defined scopes of work without me worrying that I’m going to get screwed in the end,” he says. 

But Kienle has found that even tightly-scoped contracts can be abused by workers. If a contractor or vendor wants to overcharge you, they will find an “above board” way to do it, with change orders and overages, or by overbilling hours. 

“I’ve been burned by agencies and contractors where we spent a lot of money and I feel like I don’t have a lot to show for it,” he says. 

That’s not to argue that change orders and overages aren’t sometimes justifiable compensation for out-of-scope work, but that both managers and workers ideally should aim to work with people who will “do the right thing” throughout the relationship. 

“I used to be a consultant and I’m empathetic toward contractors,” says Kienle. “I don’t want to abuse agencies or individuals. At the end of the day, I want to feel good that I got value, and I want you to feel like we treated you right.”

You can’t always pick your boss or your workers, but at least with independent knowledge work, you can more easily stick with good clients and managers as they move from firm to firm. Kienle’s history with Gather is a testament to the value of this approach. 

Hiring people from a brand that he’s come to trust eliminates a lot of stress, but like any manager, Kienle has been in situations where workers were not performing to his expectations. In this scenario, he tries to proactively resolve such issues early. 

“I ask them what they’re working on, and challenge them to summarize what they’ve been doing.” In many cases, more communication can reveal a solution. “But if they can’t account for their time, at some point it becomes not just a circumstantial performance issue, but a character flaw.”

In the scenario where he’s had to deal with the type of quiet quitter who really is shamelessly phoning it in, he’s had to make tough decisions to end working relationships. 

“I didn’t like doing it,” he says, “but not acting decisively would hurt my credibility as a leader.”

Kienle says that it can take a good six months or so to get to know a person well enough to trust them. But once you have established a baseline of trust, you want to keep that relationship going as long as you can. And that’s what keeps him hiring from the talent pool at Gather. 

In independent knowledge work, you end up working with multiple clients and multiple teams at a time. It can be easy to let these folks come and go from your professional life, but it can be advantageous to keep track of the people who’ve treated you with respect. Mutual trust doesn’t come easy, and it takes a long time to build. But if you can build a roster of trusted colleagues over the years, you can chart out a career working with good people. And when you have that, you’ll never want to quit, quietly or otherwise. 

Thanks for joining us for the Spring Dispatch. In the next issue, we’re going to explore how generative AI is going to change everything about the future of work, and what you’ll need to do to avoid being replaced by a robot. 

And don’t forget to check out the Gather Dispatch podcast, hosted by Jason Oberholtzer and Mimi Sun Longo. It’s a discussion where people from across the extended Gather Network can discuss the future of independent work from a variety of perspectives.

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