“Buy it with your heart and then run it with your head.”

Photo by Michael Fenton on Unsplash

My friend Charlie O’Donnell writes a weekly newsletter for tech that I highly recommend subscribing to. An issue from a few week’s ago told the story of a man who wanted to buy a restaurant. A very specific restaurant that was not, as it happens, for sale. When he finally persuaded the owner to sell it to him the offer was insane. As he agonized over what to do his girlfriend told him “Buy it with your heart and then run it with your head.”

It’s such a great line. I get asked, pretty frequently, what made me quit my corporate marketing job at Return Path and start Path Forward. It was, without question, a “buy with your heart” decision. It wasn’t a completely illogical — it was a staff position that still afforded me the income and benefits I needed for my family. Matt, my Board chair, had secured a significant level of funding to get us started. (The guy buying the restaurant was simultaneously wrestling with the meaningless of all the stuff — including a Ferrari — he owned. Let’s be clear that it’s a lot easier to make a decision with your heart when you are starting in a place of material security.)

But it was a decision with a lot of risk, both generally (many new businesses, both for profit and nonprofit, fail) and specifically (I’d never run any kind of business and never even worked in a nonprofit).

And yet. I can’t explain fully why I was so convinced it was the right move, but it was one that was driven almost purely by heart.

But I’ve run it with my head. I’ve focused on building a great team, including finding an amazing VP who is good at all the things I suck at. I’ve focused on building our partnerships with employers as the engine of both short term revenue and long term growth. I’ve talked to literally hundreds of people seeking wisdom and advice so I can make good decisions and avoid obvious pitfalls. That isn’t to say I haven’t made mistakes. I’ve made PLENTY and I’ve made some really, really big ones. But I can honestly say that I haven’t made mistakes that were the result of running with my heart. The passion I have for our cause runs deep in me and it drives me in an intrinsic way. But the day-to-day decisions I make are driven by a clear-eyed sense of what I think will make our organization successful so that it can continue to fulfill its mission for years to come.