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 so 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. If you want to catch just a few moments of our trip you can find them on Instagram.

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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.

Jacob.

May 21st 2016.

It is the day that you mark an important occasion, your Bar Mitzvah. And I want to stop on that thought — “mark an occasion.”

My first-cousin Sam, who came from Dallas said it best. “I made sure to be here even though it’s easier to just skip travel because there are so few occasions in life where the whole family gets together and I wanted to be a part of that. And weddings and Bar Mitzvot are much happier occasions than funerals.”

Occasions.

It is engrained in us in Judaism to respect your family and to mark important occasions. And as I think about what has defined my own character all these years is the foundation in family & occasions instilled in me by your Bubbie and Zeide when I was your age.

On today’s occasion you cross a threshold from boy to man and truly become independent.

14 years ago your mother and I were married. We lived in London at the time, right next to Hyde Park. On most weekend days we jogged around the park and jokingly talked about how one day instead of jogging around the park we would be pushing a stroller.

One year later we were doing just that. We couldn’t imagine a world in which we had kids and then in just one day — April 29th 2003 — we couldn’t imagine a world in which we didn’t.

What most parents imagine when they have children are the baby years and the toddler years. You imagine these little bundles of joy as little extensions of yourself. As a parent it’s still about “you” because you can’t imagine a world or a child that is independent of you.

And yet here we are, 13 years after you were born, watching a truly independent human being emerge.

And of course I don’t always like what I see:

• You’ll soon pass me in height
• You long ago passed me in xBox skills
• My ability to still help you in math and science probably has a short shelf life
• And although it’s questionable, I’d probably concede that you’re probably better at soccer by now

But aside from these small nits, your mom and I couldn’t be more proud of the person you’ve become.

In short we’ve watched you become independent and grow from a little boy to a young man.

They say becoming a “bar mitzvah” is about this — “becoming a man.” When I was in your shoes standing at the bimah I thought this was strange. I didn’t feel like a man at all. I had a high voice, I didn’t have a clue what I wanted to be in my life and my world still centered around my parents and family.

Only now, with the fullness of time, do I realize how much of a man one has already become at 13. Much of your personality and your character are set. You may have much book learning in school to do and of course you’ll learn about friendship, love and responsibility but the person you’ll one day become when your own children stand at the bimah is already — you.

And your mother and I are so proud of what we see and so optimistic for your future.

You have always been kind to others and you hated when you observed others on the playground who were mean to others. When your mom and I asked you about your school friends you would usually respond in fairness language like, “He doesn’t play well with people” or “He’s a ball hog.”

You always wanted friends who were kind to other people and that’s what you’ve always been.

Of course one of our favorite stories was when you were just 4 and you told me that a boy was being mean to you on the playground.

I told you — jokingly of course — that we should go and rough him up. You walked up to the boy with me and when we got really close you looked at him and started barking. Rough. Rough.

Your sense of fairness and empathy will take you far in life.

You have always had such a great sense of humor. You love to crack jokes, be the class clown or come up with witty or sarcastic responses. You love to laugh and to make others laugh. Your mom tells me that your sarcasm gene must come from my side of the family.

Jacob, you enjoy life and this enjoyment will lead to fulfillment in life.

You love to compete. Whether on the soccer field in the classroom or watching NFL football games — you like to win. But we’ve noticed and appreciated that you don’t want to win at all costs. You’ve always had a strong sense of sportsmanship and when the game is over you move on rather than dwell.

Losing gracefully is an important skill in life. And as a Philadelphia Eagles fan. You can’t let set backs affect you. Take it on the chin and move on.

Competitiveness with sportsmanship will help you succeed in life.

You have a sense of adventure. You’re always up for trying new things. You love to travel to new places and try new things. We’ve taken so many road trips and vacations together, tried new hobbies from surfing to paddle boarding to seeing Broadway shows or learning about new cultures.

Your sense of adventure and curiosity will lead you to experience life to its fullest.

But mostly I’m proud about your openness to love. I saw it when you were a small child chasing around your big cousins and idolizing them and how quickly you adopted this big-cousin role with the seven little cousins who came much after you.

Nothing will make you happier in life than opening your heart to loving others.

So, Jacob. While 13 years ago your mother and I imagined bringing a baby into this world and giving it all of our love — we were never able to imagine the world beyond a baby in a stroller in a park or a toddler running in a field kicking a soccer ball. Before parenthood that’s as far as the mind can see.

But while I stand here today, watching you become a man, I can finally visualize your future.

You have already become the wonderful human being we had always hoped you would be. We already know that you are kind, funny, competitive, adventurous and loving. And now begins the building of the one new important attribute you will acquire — independence.

Take your new-found independence with pride and enjoyment. Take your independence and make mistakes in life and learn from them.

Use your independence to figure out who you want to be in life, not who others — including your mom and dad — want you to become. As long as you promise to become an engineer.

Use your own independence to be good to yourself. You can only truly be good to others if you love yourself first and foremost. And always be good to others.

Mark occasions. Show up. Be present. Do the harder work of traveling when family gathers and when you’re older put in the time to plan for your own family to spend time together. Occasions are all we have in life.

You are a product of your parents. And luckily for you I met your mom and you got her smarts and good looks.

But we are products of our parents. Of Zeide. And Bubbie. And Papa and Kay. We pass down our values to you as they did to us and as we hope you will to your children one day. May you get to stand on the bimah one day as I get to today knowing that you upheld this tradition. That you marked this occasion.

Becoming an adult is about accepting your own responsibilities for the choices you make in life. That’s what independence is. That is the moment you are at in your life and once you acquire independence it is a gift you will have for life.

We can’t wait to see what you do with it.

Congratulations on all that you have achieved. And on your transition to a Bar Mitzvah.

We love you.

A Letter to My Son on Becoming Independent was originally published in Both Sides of the Table on Medium, where people are continuing the conversation by highlighting and responding to this story.