In the Messy Middle
Donald Barthelme famously ends one of his short stories with the sentence, “Endings are elusive, middles are nowhere to be found, but worst of all is to begin, to begin, to begin.” Beginnings, among writers and in business, are typically seen as both the toughest and most crucial parts. So much has been written about how to start an enterprise, how to come up with new ideas, how to hire (or get hired). But it’s in the middle where the important work happens. Where a team comes together, where new ideas slowly transform into fact, where agonizing decisions must be made—that all happens in the messy middle, not in the magical beginnings or tidy ends.
In this issue:
Getting through the hard parts
Embracing the mess
The messy middle for neat freaks
In praise of middle management
The messy Barca-Messi divorce
15 questions
Updates from the House
Updates from Residents
“There’s no recipe for building a high-tech company,” writes Ben Horowitz in The Hard Thing About Hard Things. “There’s no recipe for leading a group of people out of trouble; there’s no recipe for making a series of hit songs; there’s no recipe for playing NFL quarterback; there’s no recipe for running for president; and there’s no recipe for motivating teams when your business has turned to crap. That’s the hard thing about hard things—there is no formula for dealing with them.” There may be rules and recipes for first dates, introductions, and a startup’s investment stage, but once the initial flush of romance (and venture cash) is over, the formulas must be invented.
To get through the rough parts of our work—to come up with those formulas, to find our way out of a messy middle—the first thing necessary is commitment. As House co-founder Tim Leberecht wrote in The Business Romantic, commitment “means we bring our fullest selves, including our autonomy, to the job.” It requires vulnerability—the proverbial skin in the game—and strength. The words “vulnerable” and “strong” may seem like opposites, but it takes strength to be open, to let others lend their own strengths to our projects instead of acting like we have it all under control, and it takes courage to stick with a problem when things get tough. The middle is where we decide not to quit.
— Eva Talmadge
It’s also where we make a mess
There’s a saying about messy desks and genius—often in the form of a misquotation from Albert Einstein—that both is and isn’t true. (What Einstein said was this: “If a cluttered desk is a sign of a cluttered mind, of what then is an empty desk a sign?”) Creativity and messiness are often thought to go hand in hand, as are disorganization and intelligence. As for the question of the uses of a messy desk, science has several answers: Cleaner settings are known to promote more generosity, healthier eating, and less crime.
But in one study a messy office was associated with more interesting and creative ideas. “Being in a messy room,” said one of the researchers, “led to something that firms, industries, and societies want more of: creativity.”
Messes, more prosaically, are also associated with having better things to do than straighten up. Making the presentation look neat or tidying the office before clients arrive are important when you want to show someone you’ve made an effort for them. We show respect not only for ourselves in our appearance. But when the only people nearby are your colleagues, when the work you want to share is internal, and the meeting more about getting things done than looking good, a mess is fine. A mess means you’re busy moving forward. It’s not time to recover yet, or to dither as you neaten up the ends.
Middles are messy for a reason. Think of the difficulties that you’re facing in your work not as a set of obstacles, but more like compost. Let the disorder inspire you to get creative. Allow new, wild, and “bad” ideas to get tossed around and heaped onto the mess. Then give up on it—for a day or two, or a week or two. Let the fields of the mind fall fallow. Then get back in there, dirty your hands, and play.
— Eva Talmadge
But what if I’m a neat freak?
I do not like a mess. I like it when my apartment looks like a page out of a Scandinavian magazine. I can spend large chunks of a day devoting myself to getting the dust off of all the surfaces of my home. I tidy up my toddler’s Legos overnight even though I know the effort is Sisyphean, that he’ll make the same mess again tomorrow. The task calms me, I tell myself. Or maybe what I really want is to feel like I’m in control.
But one thing I learned this year, after having a second kid, was that big messes make me happy. Right now my desk is covered in mail I haven’t had time to open, a broken (electronic) tablet that I still intend to hack open and fix, and paper notebooks with ideas in them that I haven’t finished writing down. My rooms are filling up with boxes in preparation for a move. But the mess means I’ve been doing other things, like writing. Like calling friends and cooking meals instead of cleaning. A mess means I’m living my life instead of planning for it.
— Eva Talmadge
Should we all be middle managers?
As I approach my 30s, marvelling at “the young kids” on TikTok and on the streets of Berlin as they live through their many “first times,” part of me feels nostalgic, and the other feels relieved. I no longer have to prove myself. And I feel more lost than ever.
Is this the famous midlife crisis, just a bit early?
Jason Dorsey, generational researcher, says yes: “Middle age to those previous generations was a very literal term—the middle of your life. Millennials are not feeling half their life is over; they just don’t feel as young as they used to. They no longer view themselves as the young, hip, trendsetting generation. They’re not young and hip; they’re in middle management.”
Yes, I’m in middle management—not a wise retiree, not in the C-suite, and not a rebellious newbie, either. Unfortunately the first association with middle management is mediocracy, and worse: Type “Are middle managers” into a Google search and the questions that pop up are “obsolete?” “useless?” “so bad?” And yet as work and organizations become more fluid, one could argue that middle management is very necessary. Zahira Jaser, assistant professor at the University of Sussex Business School, proclaims the real value of middle managers lies in the role of building crucial relationships:
“In my 20 years of being one and then researching them, however, I have developed great respect for middle managers. They are the engine of the business, the cogs that make things work, the glue that keeps companies together. Especially as remote and hybrid work takes over—and the distance between employees increases—middle managers are more important than ever. The most effective ones are in possession of humane, sophisticated communications skills and the knack to mediate and find common grounds between actors at different levels in the organization.”
The world could use more middle managers.
It’s a stage many of us know too well from our relationships, whether romantic or business-related—or, in my case, both. When I tell people how I first came to the House at the initial Lisbon gathering in 2017, feeling like I had won the lottery, then entering a freelance relationship before saying yes, wholeheartedly, one year later, I realize how the House and I, and we as an organization, have matured. What began as an idea is growing into what we’ve wanted it to be: a manifestation of beautiful business. We’re right there too, in the messy middle, figuring out structures and processes that are meaningful, not stifling; creating an ever-open space for dreaming—with some discipline; staying rooted as we struggle to evolve.
Managing the middle, through the middle, is where love is made concrete. It’s where things get more frustrating and complicated, where you have to work harder to honor your commitments, and face tough decisions and conflicts that have been there all along.
And equally, it’s where new curiosity, collaborations, and contracts are waiting to be birthed. A departure and a homecoming together—which is also, not coincidentally, how we plan to gather this fall, too.
—Monika Jiang
The Barca-Messi divorce and the way out of the messy middle
No matter how hard I’ve tried, how stubbornly I’ve denied the facts or claimed indifference, I just couldn’t stop thinking about it over the past few days: Lionel Messi, the GOAT (greatest of all time) footballer, is leaving his lifelong club, FC Barcelona—Barca, as the fans, and I’m one of them, call it. It is the unfathomable, unhappy end of a fairy tale that wasn’t supposed to end that way, driving almost everyone with a heart for football, including Messi himself, to tears.
The reasons for the divorce are sound and sober: Barca’s finances simply didn’t add up any more. With Messi on the books, 110 percent of the club’s income was absorbed by players’ wages—an untenable situation by the Spanish league’s financial fair play rules, even though re-signing Messi (who is now most likely joining Qatari-cash-fueled Paris St. Germain as a free agent) would have brought the club significant additional revenue (there’s more complexity to it, as Sid Lowe explains in The Guardian).
Barca’s president, Joan Laporta, exclaimed, “not even the greatest player is bigger than the club,” and that he had to make the tough decision to let Messi go for the sake of the club’s future. The fans are understandably upset, even inconsolable, especially about the way this all went down, as a shocking final twist in the never-ending Messi-Barca saga. Some of them said on social media they are going to break up with their club for good.
The true fans, however, once the dust has settled and the initial grief has ebbed, will realize that Messi’s departure is not just an economic necessity but also a philosophical opening: a new era where talent from Barca’s acclaimed academy can break through the ranks.
Given the circumstances, Laporta’s decision is an example of responsible and clear-sighted leadership—and at the same time an emotional escalation, a powerful act of irrationality. The predicament Barca’s president found himself in was the result of years of obscene mismanagement (expect a throng of case studies written about it) by his predecessor. The club overstayed in a bygone era, foolishly believing in nostalgia as a self-fulfilling prophecy. It overspent and under-prepared for dire times, including COVID-19.
Undeniably, Messi’s departure is a huge loss for Barca, but it is also a cathartic act, a moment of clarity, and an opportunity for reinvention. Barca boasts that it is “more than a club,” and the Messi exit proves just that, not only because the club ultimately prioritized institution over the individual, but also because sport alone has never been the full story. Barca’s history is saddled with politics, cabal, excesses, drama, and tragedy. It is a spectacle on and off the pitch, and despite the best intentions to organize it, Barca remains a messy organization, virtually unmanageable and prone to eccentricity. But it’s exactly that messiness, that wild and utter chaos, that is and will always be at the heart of the beautiful game.
Over the past decade, business interests and commercial agendas have vulgarized football and turned it into a machine with too many games and too many parties profiting from them. On and off the pitch, performances have become more athletic and science-based, brutally optimized and data-driven, but the Messi saga reminds us—ironically, as the result of financial maneuvering—that the world of football still remains beautifully unpredictable. In every game, it is the error that advances the plot. Just like in life.
This messiness is worth celebrating. The writer Katie Roiphe, in her 2011 book, In Praise of Messy Lives, observes our “cultural preoccupation with healthiness above all else.” These lines may sound tone-deaf in pandemic times, but her heralding unhealthiness as the source of vitality is still intriguing.
Take Barca. Financially and politically, the club is the epitome of an unhealthy club—it always has been. It will rip your heart out as a fan, and if you are a player, coach, or manager—even a once-in-a-century phenomenon like Messi—it will spit you out eventually because you cannot possibly deal with the mood of the club’s members, the socios, or are simply not excellent enough in your performance. For Barca, the expectation has always been to produce success and beauty at once, and that is (mostly) an impossible if not tragic pursuit.
So it had to end that way, exactly.
There are many who project that Barca without Messi will descend into mediocrity, no longer able to compete for titles, forced to being an “also-ran” in the boring middle. But the truth is that with Messi the club has been stuck in the middle for many years now. It had long lost its edge, its ambition, inspiration, and character. It had been lacking a new vision, just like the middle-aged couple who want to breathe fresh life into their relationship with a special dinner on their anniversary and end up in the same neighborhood joint around the corner they always go to, struggling to open the play differently, just this one time.
As the Barca-Messi divorce has shown, there are only two ways out of the messy middle:
Embrace the messiness.
Or get out!
—Tim Leberecht
15 questions
Are you middle-aged?
Or just in the middle of things?
Does being in the middle make you feel like you’re at the center?
Or make you feel left out?
Are you a middle manager?
Are you where you thought you’d end up?
Did you know that stars (the kind in space) have midlife crises?
Do you consider yourself middle-class?
Did you know most people, mistakenly, do?
What is the biggest mess you’ve ever made?
Proud of it?
Do you think better when your desk is cluttered or tidy?
Do you have time to tidy up?
Look back: See any projects you abandoned in the middle that could be picked up again?
How many months of “middleness” can you tolerate? How many years?
