I Only Have 7 Trips Left. On Managing Work / Life Balance, Love & Family

Like many people these days, I spent much of my 20’s and early 30’s thinking about work & fun and not too much about “the future.” Like characters from one of my favorite novels “The Unbearable Lightness of Being” life seemed very light.

My first son was born the day before my 35th birthday so the decade that followed was very heavy and consequential. Life mattered for more than my pure enjoyment — I had to be responsible for the futures of these two lovable, little boys. I still worked hard and the balance of my time and energy went into family. My relationships narrowed to a smaller set of people who really mattered to me, my number of frivolous hobbies dwindled to only the most valuable and time became my scarcest commodity. If you’ve lived a decade with young children you know that it’s both unbelievably rewarding and also physically and emotionally exhausting.

Many of my friends and colleagues also find themselves in the “sandwich years” of aging parents where responsibilities increase for your elders at the same time as for your kids and mortality becomes a reality. During this decade we lost a close family member we loved to cancer and realized that life is too short and if we didn’t take advantage of the blessings we had to spend time together we would be shortchanging ourselves and our children.

So for the past 7 years we have ramped up the amount of sibling, cousin, grandparent, extended family time we could and we have loved every minute of this. I started thinking about “how many Thanksgivings, July 4ths or holidays we really had all together” and when you do the math it is daunting.

I already had a sense of the heaviness (in a good way) of my forties when I came across this excellent post on one of my favorite blogs WaitButWhy entitled “The Tail End,” in which the author uses pictographs to bring the succinctness of life and family time to reality. The author was 34 when he wrote this and estimated that if he’s REALLY lucky he has at best 60 Super Bowls left

If I assume that I’m 10 years less lucky (and live to 84) and I happen to be 49 years old now that means the Eagles have only about 35 more tries to win their first Super Bowl. Now you can see the urgency of Carson Wentz fulfilling his full expectations! It’s on you, Carson. I’ll do my best to make it to 90 but I’m still counting on you.

But seriously I sent this Tail End article recently to my brothers and sister recently to remind them why it was

important that we all get together for Thanksgiving this year. In kid years I have just 4 more Thanksgivings until my eldest son goes to college so I don’t have many to spare. And while I fully expect my children to come back for family vacations post high school, I’m also a realist about life and an advocate of independence.

It took losing my wife’s brother to realize how little time we all had together and the importance of getting together every family vacation we could but I also look at this as the gift that Tom gave us all in our lifetimes. And I think about Tom at every family gathering whether it’s Tania’s family gathering or mine. I am now the age Tom was when he passed away (49) and I don’t take for granted the time I have on this Earth.

So last year I talked with my wife about how few “nuclear family” trips we had been able to take given all of the extended family trips that were so important to us and we committed to doing 2 nuclear family trips per year until Jacob is in college (and of course we plan to continue this for years after and we have Andy for 8 more years!).

I just returned this weekend from our 3rd of 10 trips (70% to go!) and this time I decided not to bring my computer. I put on an out-of-office notice (see below) and received some of the nicest emails and text messages including from my good friend Michael Broukhim who ensures me that he and his brother Danny still vacation with their parents and Mike & Danny are both in their 30s! (I vacationed with my parents, too, until I got engaged at 33).

I was reading the saddest story this morning about a Silicon Valley lawyer who struggled with work/life balance and stress and the pressures of modern life of keeping up with the Jones’s and competing at the top levels in tech startup life. It’s a really sad but important story that I hope you’ll read. It is written by the ex-wife of a corporate lawyer in Silicon Valley who struggled with drug addiction and trying to maintain his status atop his field with the stresses that go with this. She titled it “The Lawyer, the Addict.

I’m not perfect and like many of you still struggle with work / life balance. I was blessed in life not to have chemical dependency issues or depression but I’ve seen it all around me and take the live’s of some people I was close to. It’s why I try to write about and be available to people who suffer from depression. It’s why I try to be open about how stressful being a founder really was and how stressful being a VC is even for an obviously “privileged class” and how physically unhealthy being a founder was to me. As you will see if you read the Lawyer, Addict piece — even highly successful people can succumb to the pressures of peer expectations and relative performance that is entirely self made destruction but real nonetheless.

I love my wife and I love my children. I think some of our fondest memories will be the goofy time we spent during our travels as opposed to the planned itineraries. We’ll remember all of the games of Hearts. We’ll remember when Andy fell down the hill into the bushes (but was ok). We’ll remember throwing the football on the beach with Troy Aikman (the nicest pro football player you’ll ever meet who even with no cameras around and even once he found out we were Eagles fans was still so gracious to my boys). We’ll remember Daddy accidentally shoving an entire Serrano chili pepper into his mouth because it was dark outside and he thought it was a carrot. And we’ll remember how much time Mom spent meticulously planning with love so that our entire family could enjoy every moment.

If you’re caught on the hamster wheel, recognizing it and trying to take some actions is the first step. Having just gotten back from my first proper 2-week vacation (as opposed to extended family gathering) since 2009 I can tell you it was truly life fulfilling. I’m now ready to come back to work feeling really refreshed. As a side note if you’ve never been to Alaska it is truly one of the most beautiful, spectacular and awe-inspiring places I’ve visited.


Below was my out-of-office reply in hopes of inspiring at least some of you to seek out your own work / life balanced vacations in the years ahead…

4 Years

Thank you for writing to me and forgive me for not responding right away.

About a year ago I was sitting down with my wife and talking about life and realizing that my two boys were about to pass me in height and in their minds they would soon be passing me, too, in worldly knowledge. As if! My eldest son was in 8th grade at the time. Like many of you, my wife & I worked our butts off in our 20s and 30s. When we had kids we did everything we could to balance daily existence, jobs, being great parents and, well, sleep. Every chance for a vacation was an opportunity to see grandparents, aunts & uncles, cousins and childhood friends. We love our families and cherish these visits but it’s different than nuclear-family downtime.

Now we face high school. And we realize we only have 4 years left as a nuclear family until we send Jacob to college. I’m even a bit verklempt as I type this. So Tania & I promised ourselves 2 great trips a year with just our nuclear family. 8 more nuclear-family vacations to create memories that we hope last beyond our time on this planet. We love our boys and our family and at this pivotal moment we also want to model good behavior where we don’t spend the entirety of our trip doing emails or checking Facebook.

So we’re off to Alaska. We won’t be 100% unplugged but we plan to as much as possible so we likely won’t see your email. When I get back I don’t plan to spend 50 hours processing old emails. So here are my asks

  1. If it’s urgent please email xxxxxxxxxxx who will help. He really doesn’t mind — even if it’s just directing you to somebody else at Upfront who can help. If it’s future scheduling of a meeting for me please email xxxxxxxxxxx. If it really needs my attention please text me (I don’t mind) but know that we may not have perfect text messaging coverage. Jori has my itinerary and can find me. No, we’re not going on a cruise. Why does everybody always ask that when you tell them you’re going to Alaska?!?

  2. If it can wait please email me again on July 15th. This is the single longest true vacation I have taken since 2009 and I can’t tell you how excited I am to recharge the batteries and crush my kids at Hearts.

3. If you find yourself today or in the future at the same life stage as I am, find a way to truly check out. You don’t get these days back. So I’m going to make the most of my 8 trips and 4 years. I hope if you’re able to you will one day, too.

I Only Have 7 Trips Left. On Managing Work / Life Balance, Love & Family was originally published in Both Sides of the Table on Medium, where people are continuing the conversation by highlighting and responding to this story.