The Higher You Rise, the More Alone You Are

Why the smartest leaders in higher ed are making their biggest decisions in isolation — and what it’s costing them

This an adaptation of my most recent visit to the Funding the Future NOW, podcast with Dr. Randy Dirks.

When a university president paused mid-conversation and said, “I don’t know why I’m telling you this,” he didn’t take it as a throwaway comment.

He took it as a distress signal.

The call had already run past the 30-minute mark. The president had let go of his VP and was considering restructuring the role to combine marketing, communications, and development under one person. On paper, it was a structural question. But the longer they talked, the clearer it became: this wasn’t really about org charts.

It was about pressure. And the absence of anyone safe enough to share it with.

His conference peers might share intel with competing institutions. He wasn’t particularly comfortable sharing it with leadership team. He was making high-stakes decisions in total isolation — and the pressure was building.”

That conversation became what Freeman calls “proof of concept.” It’s the reason he does what he does.

The Paradox at the Top

Dr. Daniel Freeman is an executive thought partner for senior leaders — presidents, CEOs, entrepreneurs, and athletic directors — navigating the moments that define their tenures. And the thing he keeps encountering, over and over, is a paradox: the higher someone rises, the more surrounded they become, and the less they can actually say.

“The higher we get, the tougher it is to have awareness of everything going on,” he explained.

“If you don’t have the processes and systems that allow for creativity and proactivity, you become reactive.”

He uses a vivid image to describe what good leadership actually looks like: standing on a balcony, looking down at the stage below — seeing the full play while still understanding every actor in it.

“As a leader, you need that 30,000-foot view. But to be a truly in-depth leader, you also need to understand how the trees make up the forest. How they interact with each other. How to spot disease. How to fill in the gaps.”

Most leaders can’t hold both at once. And without someone outside the institution to think with, they stop trying. They start reacting instead.

The Three Misalignments That Derail Philanthropic Relationships

Freeman’s lens is sociological — he’s trained to see hidden incentives, unspoken power structures, the gap between what people say and what they mean. And when it comes to philanthropic relationships, he sees three misalignments that consistently distort a leader’s perception of reality.

1. Judging the book by its cover.

“I’ve met so many people who walk into a meeting and immediately shut down because the donor didn’t look like what they expected.” The car wasn’t right. The clothes weren’t right. The person didn’t speak with the polish they anticipated.

It’s the “millionaire next door” problem — and it cuts both ways. Leaders dismiss genuine donors who don’t fit the mold, and get dazzled by those who talk a big game but can’t back it up. Freeman referenced a widely reported case where a university president and VP of advancement both lost their jobs after a promised nine-figure gift turned out to be unverified.

2. Not trusting your top fundraiser as the expert.

“If you’re a president going into a philanthropic meeting with your top fundraiser, that fundraiser should be your expert.” They’ve built the relationship. They understand the timeline — which, Freeman notes, is almost never as fast as leaders would like.

But when ego enters the room, things go sideways. “No one expects the president to be the expert at everything. The same regard you give the president for overseeing the institution should be extended to the fundraiser who has built that relationship.”

3. Treating every meeting like it’s only about the check.

Freeman tells a story from his time in Philadelphia. A donor gave $250. He called to thank them and build the relationship. The donor told him later — it was a test.

“They wanted to see: are you going to be a good steward? Are you going to treat me well even when the dollar amount is small?” That person eventually made a $50,000 gift, then initiated significant planned giving that closed after Freeman had moved on.

“If you treat every interaction as a transaction,” he said, “you’ll miss the transformation.”

What a Pulled Hamstring Can Teach You About Leadership

Before Freeman became an executive thought partner, he spent over 15 years as an athletic coach. And one of the most important things he learned wasn’t from a playbook — it was from exercise physiology.

“The point of issue is never actually where the issue is occurring.”

Back pain might mean the glutes aren’t activating. A pulled hamstring during sprints often means the athlete’s training never put that muscle through the required range of motion. The body isn’t failing — it’s guarding itself against something it wasn’t prepared for.

Freeman takes this principle directly into his work with leaders. The visible problem is almost never the real problem.

When that president was restructuring his VP role, the presenting issue was organizational design. The real issue was isolation, pressure, and the absence of a trusted thinking partner.

“I listen for the next answer,” Freeman said, “not the next question.”

Quick vs. Fast: Rethinking Urgency

One of the most clarifying reframes Freeman offers is the distinction between quickness and speed — borrowed, again, from his coaching background.

“Speed is how fast you go from point A to point B. Quickness is how efficiently you perform within a given space.”

He wants leaders to make quick decisions — thoughtful, efficient ones — not fast ones driven by urgency and reaction.

“If everything feels urgent, that tells me something important: the processes and systems aren’t in place to have seen it coming.”

The solution isn’t to slow down for the sake of it. It’s to build the kind of systems that allow the people closest to the work to handle today’s problems — freeing leaders to think proactively about what’s coming next.

“When you bring in intellectually stimulating conversation from outside the institution, it allows people to think beyond themselves. And then we can build the systems that let them be creative and proactive — instead of reactive — because they’re no longer the only person carrying the weight of the decision.”

A Few Things About Daniel Freeman

Best piece of professional advice he’s ever received: “If someone has made up their mind, they’re not going to change it. There’s nothing you can do except radically accept it.”

What he’d tell his 20-year-old self: “Be present in everything you’re doing and accept that you cannot control the outcomes you want. You have to adapt around the situations you’re in.”

The failure that set him up for success: Running a golf fundraiser 10 days after a major event — ordering four kebab varieties for 90 people, only for the caterer to make 90 of each. The event barely broke even. The next year, he was planning nine months out, had built a committee, assigned someone to oversee catering, and could actually be present for what mattered.

Where he goes to fully disconnect: Utrecht, Netherlands. He went with his doctoral program, then again with his wife on their honeymoon. “When I’m in Utrecht, the phone goes down — and you will not hear from me.”

Dr. Daniel Freeman works with senior leaders in higher education and the nonprofit sector as an executive thought partner. You can find him at fundraisewithdan.com or on LinkedIn at LinkedIn.com/DanTheEdDMan. Mention this interview and he’ll share his new ebook on executive thought partnership.

This piece is adapted from a conversation on the Funding the Future Now podcast, hosted by Dr. Randy Dirks. Available on Spotify and YouTube.