Brad Feld

Tag: life dinner

A friend from a long time ago, who I hadn’t heard from in a while, sent me an email with a wonderful nugget in it.

I just got back from Oahu and had an interesting experience on Waikiki Beach.   My son and I were boogie boarding and there were several people taking surfing lessons out in the waves with instructors. As the intrepid beginners got up on their boards and surfed one of their first waves, the instructors would invariably be shouting directives to them.

One of them was, “Direction you look is the direction you go!”

I was wrestling with this last night at life dinner with Amy. I am still Nev’s spell, so my brain only partially belongs to me right now. We were talking about where we were going, both literally (as in “should we do an upcoming trip next week”) but more importantly, figuratively.

Our best life dinners are the ones where we talk about the direction we are heading in, why we are heading there, and if we want to head there. We generally get a little time each month on the first day of the month to discuss this; last night it consumed almost all of the conversation, at least when I wasn’t sneezing.

While this conversation is often fun, it’s occasionally difficult. Last night was a mix, as I realized there was lots of different places I was looking at, which was preventing me from going toward one of them. And, the ones that I most wanted to go to weren’t getting many looks.

Anyone who plays sports knows this metaphor well. But it’s equally as good as a metaphor for one’s professional and personal life.


It’s June 1st. And that means it’s Life Dinner. On the first day of every month, Amy and I go out to dinner. It’s not “date night” (we have plenty of those). Instead, it’s a special celebration of being alive. It’s a chance to reflect on the last month and talk about what’s coming up in the next month. And an opportunity to give each other a “non-Hallmark promoted holiday” gift.

Recommendation for all entrepreneurs: If you have a significant other, declare tonight life dinner.

Here’s how. Make a reservation right now at one of your favorite restaurants. Go out – just the two of you. Buy your significant other a gift. If you are male, buy her flowers in addition to the gift. If you are female, buy him flowers also (guys like flowers too.) Or chocolate – chocolate is always good. Turn off your cell phones and hand them to the other person. Spend a long slow dinner enjoying each others company. Talk about what happened last month – the good and the bad. Don’t argue or justify – just talk about what happened, and more importantly, how you felt about it. Remember positive feedback is more effective than negative feedback. But don’t forget to talk about difficult things or ongoing challenges. Just don’t try to solve the problems in real time – focus on empathy. And keep talking. If tears flow, that’s ok – it happens. Use it to get to a deeper level about what’s going on. But stay calm – focus on empathy. Make sure you shift to talk about what’s going on in the upcoming month. And remember the tears – and try to propose some changes to the tempo so the next month goes better. Being in a relationship with an entrepreneur is hard – possibly harder than being an entrepreneur. Recognize that and keep talking. If you drink, get a nice bottle of wine. Don’t be afraid to get a second one. Order dessert, even if you are on a diet, it’s life dinner after all. Take your time. Don’t ask for the bill before the table is completely clear and you are done talking. By this point you won’t feel like checking in to Foursquare or checking your email (it’s Friday night – nothing that can’t wait until tomorrow is going on) so enjoy the rest of the evening and night together. And don’t give each other back your phones until the morning.

Amy and I have been doing this for 12 years. We miss one or two a year – that’s ok as it’s part of our fail 12.5% of the time rule (I get to blow it one out of eight times.) Occasionally we’ll invite another couple – tonight we are having dinner with Bala Kamallakharan (the creator of Startup Iceland) and his wife Agusta who have been incredible hosts for us this week in Iceland. But usually it’s just the two of us.

Every now and then it’s a total disaster. I can remember at least two times where the tears were so intense that the waiters stayed away for a while. But we hung there and kept talking. And the tears eventually stopped and we got to a deeper place. And it was good, full of truthiness, and worth it.

Our gifts have ranged greatly over the years. Amy gets lot of art and jewelry. I get Tom’s shoes with skulls and crossbones, remote control fart machines, and a Range Rover. I think this month I’m getting a bunch of Puffin Made In Iceland Wool Hats. It evens out over time but it always brings a special smile to each of our faces when we see the other person enjoying their Life Dinner gift.

Try it. Tonight.