There Is No Boomer Succession Plan

How a generation that didn't form its successors is structuring around its own absence

One of the core elements of the American Transition I’ve been writing about is generational turnover and the crisis of leadership in America. As a nation, our institutional leadership has been dominated by Boomers for over 30 years. And starting long before the Boomers ascended to that position, we’ve had a sense in America that we face a growing leadership deficit, something attested by declining trust in institutions.

America needs to both navigate through generational turnover, and start rebuilding its leadership capacity.

A recent article in the New York Times on the future of the Metropolitan Museum of Art’s Costume Institute annual gala (gift link) sheds light on how some institutions and leaders are thinking about this transition to post-Boomer leadership.

Simply put, they aren’t planning for there to be one. The existing Boomer head of the Met Gala, longtime Vogue magazine supremo Anna Wintour, age 76, is sticking around. And the plan is that by the time she’s done, the gala will be financially superfluous.

The piece starts by asking about the future of the event given its high profile stature, very high dollar take, and high wattage leader in Anna Wintour.

For years, as the Met Gala has grown ever bigger, blanketing social media with pictures of guests in their finery, smashing cultural fund-raising records, teetering on the line between fabulous and ridiculous, the questions and controversies surrounding New York’s “party of the year” have likewise proliferated.

Could the shindig, nominally a benefit for the Costume Institute of the Metropolitan Museum of Art, get any more high-profile? When most of the country was struggling, should any institution be charging $100,000 a ticket for a party? And perhaps most important: What would happen when Anna Wintour, the evening’s mastermind and the woman who transformed it from a typical charity ball into an attention-guzzling juggernaut, retired?

…

What made the Costume Institute an anomaly in the museum ecosystem was that it raised most of its money via a party — one that had increasingly overshadowed almost every other activity of the museum itself, and that, like Wintour’s daytime employer, Condé Nast, seemed increasingly reliant on her presence and power. And though Wintour has been quick to say she is not going anywhere, she is 76 and last year relinquished day-to-day control of American Vogue to focus on her role as Condé’s chief content officer.

“Anna Wintour is not replaceable,” said William Norwich, the editor for fashion and interior design at Phaidon Press and a former editor at Vogue. [emphasis added]

This story is deeper than the Met. It illustrates a pattern of how many Boomers have led in American institutions. Wintour is a legendary editor. She was known as a fashion kingmaker and worked with a stable of photographers she helped make famous (or in some cases, more famous). But she is not especially notable as a developer of equivalent editorial talent, and seems not to have produced anyone who could plausibly succeed her at the Met Gala.

That failure seems characteristic of very top tier Boomer leaders. From what I’ve observed, they saw themselves as talent developers, but were unable to successfully create successors or protégés of similar accomplishment.

Two additional examples will illustrate. Mitch Daniels is widely seen as the greatest political leader in recent Indiana history. He was a transformational two-term governor. He gained national press for a successful transformational tenure as president of Purdue University. He was touted as a potential Presidential contender. He is associated with a leadership development program that bears his name, showing his commitment to the subject. Yet none of his protégés have come close to equalling his record. This is a big contrast to Daniels’ own mentor Richard Lugar, who not only helped develop Mitch Daniels himself, but multiple other very high impact local civic leaders whose names are not nationally known.

Another example is the legendary urban pastor Tim Keller, builder of New York’s Redeemer Presbyterian Church and the de facto creator of evangelicalism’s modern urban church movement. He invested a lot of personal time and money to train the next generation of pastors, something clearly very important to him. But none to date have become leaders or had impact on a similar scale.

It’s not obvious why this happened with Boomer leaders, but it’s worth studying in more detail. I have noticed that top Boomer leaders, like Wintour, tend not to surround themselves with people who might ever plausibly equal or upstage the boss someday. Or who have their own ideas. They want people who will completely subordinate themselves to the boss’ ambitions and vision. They also seem to believe that they alone have what it takes, which might account for why many of them hold on to their positions for so long.

Returning to the Met Gala, it appears that for quite some time the Met has realized it is not sustainable. Part of this is because it is the very nature of such events to rise and fall. Especially in fashion, we should be expecting things to be going in and out of style.

But Met leadership also recognizes that it simply will not be possible for anyone to plausibly fill Wintour’s shoes. What do you do when your leader is irreplaceable?

Their solution appears to have been underway for some time: save enough money from the last days of Wintour into an endowment so that the Costume Institute never has to raise funding again - or at least nothing like what it does now.

Would the brands and people willing to pony up these exorbitant sums to be in one another’s orbits instead pocket the money [after Wintour is gone]? And if so, what would that mean for the future of the Costume Institute, a department that has been almost fully dependent on the gala as a source of its annual funds since the party began, in 1948?

Could it even survive without the extravaganza?

It turns out the museum itself has been quietly working on an answer.

“Since 2016, we have been putting some money that we raised for the gala aside into a quasi endowment,” Andrew Bolton, the Costume Institute’s curator in charge, said this month.

And by 2030 — possibly as soon as 2028 — the Costume Institute will have saved enough of a nest egg to potentially support its own basic operations for the foreseeable future, no matter what happens in the greater museum economy or with the gala itself.

…

Though [Costume Institute curator-in-charge Andrew] Bolton and a museum spokeswoman said it was museum policy not to discuss specific department finances, and though the Met does not break out such numbers in its annual report, they did acknowledge the Costume Institute fund had been formally created in 2016 and was, like most of the museum’s endowments, run by the Met’s investment and development teams…Still, some back-of-the-envelope math is possible. Given that the operating budget of the Costume Institute is approximately $5 million a year, it would most likely require an endowment of between $100 and $130 million. (According to the American Alliance of Museums, 5 percent is the average draw of an endowment fund.) The gala has raised $166.5 million over the past 10 years, so subtracting the operating costs and the amount that goes directly to the Met would suggest there is approximately $106 million in the fund (a bit less if there were unusual expenses one year). This year’s gala added a record-setting $42 million to that sum, so if the party continues on the financial trajectory it has set for another two to three years, that would easily ensure enough capital in the fund to allow the department to essentially live off the interest going forward.

This plan has obviously been ongoing for some time.

To some extent, this is a smart move. The Met recognized that there was no next generation leader that could sustain the event at its current level. So they created an endowment to sustain the Costume Institute without pressure on Wintour’s ultimate successor to continue raising huge dollars via the gala every year is a good idea.

Tim Keller’s succession plan at Redeemer Pres had some similar attributes. After he officially retired as pastor, he used his star power to conduct a large fundraising campaign that no successor could plausibly pull off - about $100 million. He also split his church into three separate, smaller church entities with shared services between them. I said at the time, and still believe it, was a really great plan. There simply wasn’t, and in his case perhaps never could have been, a successor with the kind of star power and competence necessary to sustain the enterprise in its previous form.

It seems likely that many institutions will follow a variation on this path: maximize the return on current Boomer leadership, while structuring around a future with a diminished role for leadership - and possibly the institution itself - once the Boomer leader is no longer there.

This is actually the right move in many cases. When there’s no obvious high stature successor, or institutional sustainability is in question, institutions where it’s feasible should be thinking about this kind of approach. (This was not necessary, however, at Purdue, where Daniels recruited a solid successor in Mung Chiang, someone who was largely formed at Stanford and Princeton, outside of the Daniels ecosystem).

However, there’s another side to the Met Gala story specifically. Wintour took over an event tradition nearly 50 years old. She transformed it into something bigger and bolder than anything her predecessors could have conceived of. But she also squeezed much of the juice out of it such that when she in turn does ultimately hand the baton to a successor, it’s likely destined to diminish rather than continue growing. Her successor will never have the ability to do what Wintour herself did with it, regardless of how talented that successor might be. As Bolton, who is Gen X, put it cryptically, “It’ll be interesting to see how it’s going to evolve.”

This reminds me of how at a partnership I used to work for, as soon as the last Boomer made full partner, they IPO’d the company and capitalized all the future returns for themselves. Future generations would never get the opportunity previous ones had. Or think about how the United States went from $3 trillion in debt when the first Boomer became President to $39 trillion today. No future generation will ever get the same benefit of being able to borrow $36 trillion that they won’t have to pay back.

As a rule, institutions should not allow themselves to become over-optimized around a single person (or generation), no matter how talented, in ways that sacrifices the long-term trajectory of the institution or future generations.

Part of leaving a place better than when you found it means making sure its future stewards have the same or better opportunities than you had. Our failure to do that in America writ large - or at least the widespread feeling that we’ve failed - is why so many people think the American Dream is dead.

Perhaps the most important part of getting through the American Transition is to reset the game board here, so that people think they are on a personal, institutional, and national upward escalator extending behind and ahead of them through time.

Cover image: Anna Wintour by UKinUSA/Wikimedia, CC BY-SA 2.0