When in conversation about co-founding, running, fundraising, and eventually selling a start-up, there is one question that is guaranteed to come up. I hate this question. And that question is: “What would you do differently if you knew then what you know now?”

My stock answer is “nothing.” Because, I continue: it’s an unanswerable question, at least if you’re being honest. Because, I’ll add: if knew then what I know now, I would have entirely different decisions to make at any given step. One change would create a Sliding Doors cascade of changes. Finally, I’ll conclude: I did what I thought was the next right thing working with the information, experience, resources, expertise, and intentions at that moment.

I realize these stock answers don’t deliver what people may want to hear from someone with my experience, so I often continue by sharing that there are a couple of really big picture things I’ve learned that can help people in similar circumstances. [I'll share a link to those things below, but I’m here to talk about something else right now.]

It’s funny that I’m anti-second-guessing about professional decisions, because I am also the person who still remembers the girl I was mean to once in junior high and feel ashamed. I’m the person who sometimes randomly remembers the time I mistook one someone for another someone and felt deeply guilty, despite not having seen either of those someones in a decade. I’m still the person who remembers with horror what I will call a Chadwick Boseman moment, where I commented on how thin a friend of mine I hadn’t seen lately looked…like it was a good thing…and then found out shortly thereafter that he was ill, in fact dying.

I have no problem with personal recriminations, so I’m not sure why I cut myself so much slack about my professional decisions.

Mulling over the Buffy episodes I watched this week (Season 3’s The Wish and Amends) is what got me thinking about this much-reviled question on my morning walk today. And I had a little brainstorm (which often happens to me while strolling my neighborhood).

You cannot recreate your past, you can only create your future. And you’re walking into every decision with, as I said above, the information, experience, resources, expertise, and intentions you have marshaled up until this very moment.

This week’s Buffy episodes were really about these two sides of the coin. In S3E9, The Wish, we get a kind of It’s a Wonderful Life vision of Sunnydale if Buffy had never come to town. In case you’ve forgotten how dark It’s a Wonderful Life is for much of the movie, the dystopian and dark Buffy-less Sunnydale is a reasonable analog here. The character who wished for this in a moment of weakness regrets it almost immediately. (Quicker than Jimmy Stewart does in IAWL.) The day is saved when Giles, the wise Watcher, takes a risk that he hopes will reverse the wish. When asked how he knows the next reality will be any better than the current one, he says only, “It has to be.” He doesn’t have certainty, but he knows where he’s been, and everything leading up to that moment results in his decision.

In S3E10, Amends, the episode title says it all. The vampire with a soul, Angel, is tortured by knowing the awful things he did before he got his soul back. And believes there is no way he can make sufficient amends. The only solution he sees is to let himself be destroyed. He believes that is the right (and strong) thing to do. Buffy is not having it. She tells him he has the chance from here on forward to do real good, to make amends, and most of all that “…strong is fighting. It’s hard, and it’s painful, and it’s every day. It’s what we have to do…”

That is absolutely one of the over-arching themes of Buffy the Vampire Slayer, a sort of twist on the famous JFK quote:

And again, the through line is that they do these hard things without certainty.

I love both episodes because they tell us that life is not a one-way street with no exits or U-turns (something else I’m fond of saying.) We may not be able to change our past. We may not be able to foresee our future (or potential futures), but we can keep gathering more information, learning from our experiences, building more resources, honing our expertise, and further cementing our intentions.

We can make amends. AND we can abide by another famous quote, this time by Maya Angelou:

Ever moving forward.

So, tell me: Having done what you did then, what do you know now??

PS: I promised you two big picture lessons I’ve learned from what “I did then.” You’ll find both lessons in this interview I did for the PreVetted podcast…one about fundraising (or not) and one about valuations, exits, and how they’re more about vibes than you probably realize. Maybe one day I’ll write a newsletter just about those two lessons, but in the meantime, you can listen to this conversation and hear them now

Bonus: here’s what my meal planner tool looks like now. You can use it yourself…it lives on your local device. Let me know if you’d like the prompt I made, so you can create your own custom meal planner.

I am constantly saying that we need to hold institutions (e.g. big tech and government) responsible to do better making policy around AI than they did around social media. Hindsight is 20/20 right? So, i had a stern talking to with myself about my scornful initial reaction one big tech company at least doing something. Performative? Perhaps. Better than ignoring the conversation altogether? I have to believe yes.

I watched Season 3, episodes 9 (The Wish recap) and 10 (Amends recap)…which aired on December 8 and 15, 1998 respectively.

The core #BuffyLifeLesson in The Wish is not just be careful what you wish for: Although that’s there for sure. At its heart the lesson is hoping for a better world is worth doing, even without certainty. Yes, Giles takes a risk to get things back to the way they were. And that’s the first step.

The core #BuffyLifeLesson in Amends is that beyond hoping, there is action. And fighting for the world we want. First we see Giles, in the previous episode, take a risk to get things back to the way we were. And then in this episode Buffy admits to Angel that being strong and fighting is hard. But it’s what we can do to make the future better. It reminds me of Samwise Gamgee’s speech in The Two Towers, “…there’s some good in this world, Mr. Frodo, and it’s worth fighting for…” I feel this way today, when things in the world feel so very tough. That yes, I’d like to get some things back to the way they were, and then yes, I’d like to keep fighting to make them better. If you feel that way, you might want to watch Sam’s speech, like I just did. 😿

I’m here every week, using pop culture (and Buffy the Vampire Slayer right now) as a jumping off point for everything I’m thinking about professional leadership, personal development, political philosophy, and pop culture. I would love you to join me by subscribing. And I would love you to share the link with other nerds like us!