I Stayed Too Long

A conversation over sushi changed how I think about capability. Recorded version inside.

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Jon and I went out to omakase last week in the West Village. Date nights are hard to schedule with a toddler, but we make time to be together, just the two of us. Late into the meal, a man in his 50’s sitting alone at the bar struck up a conversation with us.

We started chatting and learned that he had recently started writing on Substack after shutting down his hedge fund. Although he spent his whole career in finance and had access to both the capital and connections to keep growing his fund, he retired.

When pressed about it he said: “I learned I was a great manager. I was a great leader. But I wasn’t a great capital allocator.”

He explained that being mid-career and closing down a hedge fund with over a billion dollars under management was tough. It was difficult to explain to his investors that the investing game just wasn’t for him. And he didn’t want to spend the rest of his life being mediocre at something, even if he was widely perceived as successful.

Recognizing that something impressive to others is not your particular strength is an important form of self-awareness.

Staying with something just because you’re capable of doing it can become a trap, especially when the work sounds elite and pays well. But the opportunity cost of staying in a role you are merely good at is never discovering what you could be exceptional at.

This conversation resonated with me because I’ve often approached work asking the question, “Can I do this?” And, as it turns out, I can do a lot of things. But most capable people can do a lot of things. Just because you can do it doesn’t mean you should.

I’ve stuck out many jobs longer than I wanted to just because I could do them, or even do them well.

The harder and more honest question to ask is, “Am I unusually suited to this?”

That requires a deeper level of introspection that notices what work you feel at ease with. It’s the work where your particular combination of skills, experiences and intuitions give you an edge.

If you’re unsure, ask: What work do people come to me for again and again? What is the thing people recommend me for when I’m not in the room? What type of work is easeful and joyful?

At the end of the evening when we said goodbye to our sushi friend, I didn’t find it impressive that he was a former hedge fund manager. But I did find it impressive that he had the courage to leave in pursuit of discovering what he thought might be his life mission.

Instead of asking, “Can I do this?” ask, “Am I unusually suited to do this?”

That’s where you’ll find your edge.


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Frontier Tech Roundup — SheFi Edition 🏇


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SheFi Global Events + Opportunities 🌎

Stay connected with SheFi around the world. From meetups and summits to workshops and special partner events, this is where you’ll find the can’t-miss gatherings happening across our global community.

09/23-30 Sicily: Roots & ReFi: RSVP here

Our global ambassador Julia is hosting a retreat in Sicily for women in the blockchain and AI space this September. We’ll spend 4 days in the picturesque fishing village of Scopello, on the edge of the Zingaro nature reserve, and 3 in Ragusa, the southeast tip of the island. We’ll visit the olive groves on the land GrowFi and RiFai Sicilia have purchased for regenerative farming funded by regenerative finance, and spend long days exploring Sicily, eating well, swimming, sailing and plenty of other activities.

The retreat will have a positive sum effect on both the participants and the environment! Find the information here and reach out to Jul directly if you’re interested.

Opportunity: BITCOIN TREASURIES - Delegate Application: Apply here

30 women. 30 sponsored seats. One seat at the table.

Applications are now open for the Women in Bitcoin Delegate Program at Bitcoin Treasuries Conference 2026 in New York City.

We’re selecting 30 women working across Digital Assets/Crypto, TradFi and FinTech for fully sponsored conference seats and dedicated Women in Bitcoin cohort programming.

📍 SECOND, New York City
📅 September 28, 2026
⏰ Applications close September 18


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Crypto Events 🌎

Going to ETHCC, Token2049 or Devcon? Join our Global Events Telegram Chat: https://t.me/shefisummit

  • 09/23 Munich: Ethereum Munich #7 🥨: RSVP here

  • 09/25 London: Coffee & Breakfast, with STUK and Altitude: RSVP here

  • 09/26 Chicago: LOVABLE × KARAOKE: Build the future of karaoke…. Then sing with it!: RSVP here

  • 09/26 Istanbul: Monad Blitz İstanbul v2: RSVP here

  • 09/28 Zurich: Blockstories Horizon 2026: Zurich Summit: RSVP here

  • 09/29-10/02 Washington DC/NYC: The Future of Money, Governance, and the Law: RSVP here

  • 09/29 Turkey: Grok Bot Meetup Istanbul w/ Neon Apps & RevenueCat: RSVP here

  • 10/06 Singapore: OKX Now, Singapore: RSVP here

  • 10/06 Singapore: SH3 Connects Coffee Meetup Singapore Edition Token2049 💫: RSVP here

  • 10/08 San Francisco: InTheRoom: Trust, Presence & Connection - #SFTechWeek: RSVP here

  • 10/16 Washington: Groundwork: RSVP here

  • 10/19 Florianópolis: IslandDAO v5: Florianópolis Brazil: RSVP here

  • 11/17-18 Florida: EthWomen Florida: RSVP here

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