I write a lot about approaches to living life. Most of the time it’s of a spiritual bent, i.e., don’t look OUT to the world to heal what ails you inside. Look inside to heal what ails you inside.

Today’s approach to life is more of a practical/pragmatic variety. It’s about maximizing the good while minimizing the bad. What does that mean?

I’ll use my life to illustrate. When I was in my twenties and thirties, I was single. As I reached my upper twenties, I started to make some decent money.

Single and free

There was tons of upside to this life, spent mostly in Washington, D.C. It was mostly about one word: Freedom. I had zero attachments.

How did I take advantage of this state of affairs? In other words, how did I maximize this life situation? Let me count the ways…

Because I started making some money and had only me to spend it on, I did some spending. Not crazy spending. I’m not the Porsche, Gucci loafers kind of guy.

But I did buy a nice townhouse just north of Georgetown. And I put a hot tub in the back area (more on that later!).

Steaks and Sea Bass

There was a high-end grocery store called Sutton Place Gourmet literally 200 paces from my place (yes, anal me counted it once). I’d go there and buy Chilean Sea Bass, prime steaks, and all kinds of great produce.

But what’s good food without good wine? So I dove into the wine world, head first. I’d go to MacArthur Beverage, where wine God Robert Parker got his start, and buy cases of Bordeaux and the like.

My lobbying friend Bob always accused me of getting into wine solely to impress women. Which was, mostly, untrue. Though I’m not going to lie, making a woman a nice soy-marinated salmon with a good bottle of Sonoma Pinot Noir never hurt one’s chances of getting another date.

Fun in the hot tub

Back to the hot tub. I could write a whole article on this but suffice it to say that it became legendary in DC. We, mostly my friend John and I, had some amazing parties there after nights out on the town. But like Las Vegas, what happened at the hot tub stayed at the hot tub, so on we go to…

Travel. When one is single with a little extra cash, one travels. At least I did. I went to Israel for two weeks and toured the most historic area in human history. The Wall. The Dead Sea. The sunrise at Masada. Portugal for the World Expo.

And the Cannes Film Festival in 1998. We went to the Hotel du Cap for drinks where we saw Bruce Willis, Brooke Shields, Sharon Stone, and Winona Ryder.

A brush with the infamous Harvey Weinstein

True story. End of the night, after waiting forever and a day at the top of the stairs of the hotel entrance for our cab, it finally rolls up. At the bottom of the stairs Harvey Weinstein, with two Waify models in tow, heads for our cab. At which point I, who was slightly inebriated, yelled out, “HARVEY! Don’t you dare take our cab!”

He looks up at me, then says to the woman, “Who is that? I don’t know who that is…” We ran down the steps, got in our cab, and skedaddled. I knew back then that he was an awful guy, but not as awful as we all learned two decades later.

Minimizing the downsides of my single life

Alright, enough reminiscing about my good old single days. Let’s get into the minimize part of this life strategy.

I was single. Had decent money. And not responsible for anyone but me. Sounds great, right? And it was. But it wasn’t perfect.

What was missing? It can get lonely being single. Yes, I had a few long-termish girlfriends (6–12 months), but more often than not, I was single.

So how did I minimize this part of my life that was lacking? I got good at making sure I was seeing friends on weekends. I also stayed, and still do, in close touch on the phone with my family and some close friends from college. All this was in service of making sure I had regular human contact, something essential when one is single.

Marriage and kids

Now we take a 180-degree turn where my life flipped the other way. Remember those wacky, fun nights I mentioned? Well, in March of 2000, I met my wife on one of those.

We got married in 2005, had kids in 2008, 2010, and 2016, and here we are in 2023, one big, loud, boisterous, funny, and incredibly fortunate family.

What are the positives of this time of life that I try to maximize? They’re obvious. I have a lot of people around me. People who mean a lot to me.

So I go to tons of sporting events. Serve as an unpaid chauffeur, shuttling kids to practices, fast-food runs, friends’ houses, and the beach.

Dinners and Gerky Specials

I have fun making dinner every night, catching the news, and sipping a Gerky Special (vodka with fresh-squeezed grapefruit juice) as I go along.

I take my six-year-old to the beach (fifteen minutes away) and watch her have a fabulous time. Play tennis with my thirteen-year-old daughter. And watch my son play in most of his lacrosse games.

My wife and I have also had a blast making friends with the parents of our kids’ friends. We party together. Laugh together. Bitch and moan together. It has been one of the pleasant surprises of having kids.

Doesn’t sound as fun or exciting as my previous life, does it? But I wouldn’t trade it for the previous one for all the tea in China.

A better life by far

Why? Because my old life was all about me. My current life is far from it. Any of you with kids knows this. If it’s not a universal truth, it’s damn near it: People are generally happier the less they focus on themselves and the more they give their attention to others.

The downsides to this life are obvious. It’s hard for me to pick up and travel somewhere. I can. And I do. But it’s generally trips of three or four days, not two weeks. And I’m not heading to Paris for a four-day trip.

Kids and families cost a lot of money, too. So no more expensive wines. And I can’t remember the last time I had Chilean Sea Bass.

Not to mention, kids screaming at each other, or at me, or vice-versa, drives me crazy. Ditto wives.

But again, I wouldn’t trade this life for anything.

The takeaway

The key to this approach to life is to be hyper-focused on the positive side of what your situation offers. If you’re single, take advantage and go out and have fun. Travel. Play the field in your romantic life. Be spontaneous. And do your best to cultivate friendships to offset the lonely times.

If you’re married with kids, cherish those relationships. Reap the profound benefits that come from a life based on love and unselfishness.

Bottom line: Put a ton of attention on avoiding a ‘grass is greener on the other side of the pasture’ life.

“If only I was married and had kids I’d be so happy…”


“Man I wish I was single again and could chase any woman I wanted and do whatever I wanted whenever I wanted to…”

No. Don’t allow yourself to live in the moan zone.

Employ this life strategy and you’ll find that the grass under your feet is plenty green.