50 Reflections at 50

Like most people turning 50, my life has been a mix of good and bad, hard and easy (definitely more good than bad; the jury’s still out on hard vs. easy).

On the plus side, I have two wonderful kids. I’m healthy. I have a ton of friends, really close relationships with my family, and a burgeoning personal relationship that feels very meaningful. I’ve had a career so far that’s been fulfilling, engaging, challenging and lucrative in multiple fields. I have a lot of interests and ideas, and, luckily, I have the resources and ability to act on them. I also have all of the basics that I regularly take for granted, ranging from clean drinking water to freedom of speech to a safe place to live.

On the negative side, my marriage didn’t last, my childhood was pretty unpleasant, and it took me way too long to realize most of the things below, so I tortured myself for far longer than necessary (and sometimes still continue to do so).

Everything we do professionally — venture capital, political consulting, trying to end childhood hunger, trying to save democracy through mobile voting, trying to use technology to preserve basic rights, owning a bookstore, the Gotham Book Prize, writing fiction and nonfiction books, writing columns, teaching grad students, podcasting and the rest — is inherently hard, so there’s rarely a moment where things across the board just feel universally good on all fronts.

But overall, I feel like I’m finally getting the hang of it. I accept myself. I generally like myself. And I have a much better sense of who and what matters to me. So as I turn 50, I thought it’d be helpful to share a compilation of the most important lessons I’ve learned so far.

The Basics

(1) Being a person in the world is hard. We don’t know why we’re here, what we were before we got here, or what comes next. We feel multiple, conflicting emotions all of the time. And because everyone is torn between good and bad, selfish and selfless, most people’s lives are always uncertain and changing — to the point where it sometimes feels like the gods created humans solely to perform the most Shakespearean drama/ comedy/ tragedy ever.

It’s that ability to know wrong from right but still go either way on any given decision that makes humanity so fascinating and, sometimes, so awful. You wonder sometimes that if there is a God (I believe there is), why were humans created to be so imperfect rather than just automatically doing the right and smart thing every time. Maybe so we have free will. Maybe we’re still in the middle of the evolutionary process. Or maybe we are just entertainment.

(2) Life is not linear. There’s no one moment where you’ve made it and then everything is suddenly and continually great (this is known as the arrival fallacy, which means you’re never nearly as happy as you’d expect when you finally achieve something. The lesson, which I’ve learned the very hard way, is to be able to take joy and meaning from the process of trying to do something meaningful and impactful and difficult, independent of the outcome). It keeps bouncing up and down and it’s rare that everything is good or everything is bad at the same time. You never stop feeling or thinking, making life a constant process of adjustment, of trying to understand yourself, of facing down doubt, uncertainty and fear. And then doing it again. It can be a lot.

Truth is, it never really gets easier, but you do tend to learn what to worry about and what not to worry about and it turns out most things you worry about aren’t that big of a deal.

(3) Everything does not have to be perfect — or even good — for you to be happy. There’s too much going on and too many uncontrollable variables to make perfect — or even very good — the baseline for everything (and even when things are going well, there are still plenty of days where you just want to hide under the covers). You just have to accept that change is constant and nothing worthwhile is easy. And because life is simultaneously good and bad, a lot of the parts that are worth paying attention to tend to happen in the gray.

(4) We have a relatively brief time on this earth. The only quotient that ultimately matters is happiness. The only way to ultimately maximize that is to feel genuinely good about yourself. In many ways, it’s figuring out how the equation works best for you.

What will maximize the way I feel genuinely good about myself? Lifestyle? Status? Helping others? Solving problems? Creative output? Physical activity? It differs for everyone. But figuring it out is critical (this is what I like about Judaism. Since there’s no after life and no reincarnation in the Jewish worldview, all that matters is the life you lead here and now. And as I understand it, the thesis is that the better of a person you are, the happier you’ll be. I saw a sign recently that summed it up well: the reward for living a good life is living a good life).

(5) You don’t get points for extra suffering or being especially stoic or feeling like you’re more righteous than everyone else. You are responsible for yourself and when it’s over, there’s no second chance. Your life is what you make of it and nothing else. Having a long list of excuses and people to blame is useless (and quite annoying to everyone around you).

(6) Things happen because you make them happen. If having a real, material impact is truly important to you, then make sure you make the absolute most of every opportunity. Make sure you take real risk, have balls, question conventional wisdom, be relentless, not let criticism deter you, are willing to engage in uncomfortable conflict, and most importantly, do it because it genuinely, innately makes you feel good, not because someone else praised you for it or it checks a box somewhere (at my son’s graduation, the head of the middle school read a great poem that captures this last sentence perfectly. It’s called The Paradoxical Commandments by Dr Kent M. Keith).

If you can do that, there will be things in your life that you will feel really good about — feelings that will last and feelings you can turn to when times are hard. For example, the work we do at Tusk Philanthropies around hunger helps sustain me, especially when I’m dreading doing something at work and can then remind myself that the good feelings I get because we’ve helped feed nearly 13 million people on a regular basis only happened because my day job, good and bad, hard and easy, gives us the money to run and fund these anti-hunger campaigns.

(7) Each moment is equally important, with a handful of exceptions. Losing moments worrying about the future or lamenting the past accomplishes nothing. It just makes your life worse. You can’t change the past and you can’t really control the future.

It took me years to realize this and even longer to begin meditation. I now meditate daily and I’m glad that I do because it has helped me learn to be more present and to learn to appreciate the present more. But I tried multiple times to get into meditation and failed. It only finally worked when I genuinely wanted to have a new way to reach myself and not because it was on some list of things that healthy or happy people do. And not lamenting the past or fantasizing about the future is still a constant challenge.

Understanding and Accepting Yourself

(8) You have to learn to accept yourself, especially your negative qualities. You don’t need to be perfect. Everyone has flaws. Lots of them. If your flaws aren’t hurting anyone else, don’t worry about them and don’t hate yourself for them. You’ll live much easier and be much happier that way (and being truly okay with yourself is the best way to kneecap someone else’s judgment and take away their power).

(9) Give freely. Love freely. Receive freely. Turns out no one is keeping score.

(10) Be generous — with your time, with your money, with your compassion. Sometimes people burn you by accepting your help and not reciprocating or paying it forward to others. Some people are freeloaders. But in the grand scheme of things, it usually works out.

(11) A little kindness goes a long way. And holding grudges never works. It eats away at you more than it hurts the other person. That doesn’t mean not recognizing people who are toxic and avoiding them at all costs. There are people who absolutely should be cut out of your life, full stop, and recognizing that is critical. It just means trying to let them go fully so it’s not a burden on you.

Anger has been an issue for me throughout my life. It kind of makes sense — between whatever traumas you suffered as a child, as an adult, between unfairness, injustice, disappointment, failure, there are lots of things for each of us to be angry about. And I’d be lying if I said I haven’t used it at times to take on fights that maybe I otherwise wouldn’t have and sometimes that helped achieve things that didn’t seem achievable.

But at the same time, it’s toxic. It’s terrible for you. It just makes things worse and worse. I am by no means free and clear of it (not even close), but I finally understand that the best thing I can do for myself is to try hard to let it go (to be clear, this doesn’t mean that you have to take shit from anyone).

(12) Perspective is important but so is being kind to yourself. Lots of people around the world have it worse than you but that doesn’t make your problems any less significant to you. There are cultures that have much less money but much stronger family and community structures. Their lives are hard because not having resources makes it hard. Here in the United States (and across the western world), we have abundant resources, which makes life easier in many ways. But we’re told that happiness comes from obtaining stuff, when it really comes from relationships and fulfillment. There must be some way to reconcile the two where we can have the things that make life easier while still prioritizing the things that actually matter.

(13) If you had a rough childhood, there’s no need to hate the 6 year old you or the 12 year old you or the 16 year old you. That kid probably had a really rough time without the support to handle it. That kid deserves compassion, not disdain.

In fact, having compassion for yourself in general is a very good idea (the key is being able to be compassionate while still holding yourself accountable for your choices and learning from them). Now that I no longer hate the child I was (bullied relentlessly for years and years), I’m also now able to see some bright spots from the past too. Nostalgia is now allowed and that’s a new (and nice) experience for me.

(14) The only right path is the one that feels right to you. So while it’s good to get opinions from people you trust — the only opinion that ultimately matters is your own. There’s no reason to let anyone else dictate your preferences or choices (conventional wisdom is highly overrated and likely just reflects the best interests of someone who isn’t you).

This is why it’s weird to me that people pledge their allegiance to the Democratic Party or the Republican Party, or even worse, base their identity around it (and I get the tribal need to belong to something). Those party bosses you’re being led by could give two shits about you other than milking you for donations. You’re just being used. Once you’re letting other people think for you or dictate right and wrong for you, you’re already lost. Don’t give them that power.

More broadly, after spending three decades in government and politics and seeing firsthand how all of it works — city government, state government, federal government, executive branch, agencies, legislative branch, running campaigns — this is my take on how to see the system and how to fix it.

(15) There is no such thing as moral purity. Every thinking person has different views. You don’t have to agree with someone on every single thing in order to interact with them. Nor should you let anyone else tell you how to think or what to believe. Figure out what your own moral compass is, live by it and don’t worry what anyone else says (and stay off social media if at all possible).

The worst people are those who claim purity, decry everyone else, issue endless judgments, act self-righteous, tweet endlessly and then when you actually look at the tangible good they do — do they give away their money, do they volunteer, do they proactively seek to help people every day — almost invariably, they do nothing useful for anyone.

Fulfillment (and money)

(16) Fulfillment is one of the two key factors to achieving happiness (relationships, covered below, is the other). Fulfillment can come from your work, your volunteer activities, your hobbies, your family, your faith. But it means feeling good about something you do and then enjoying the contentment it brings. Living without it, or just tying it to external markers of success, is a recipe for misery.

(17) Money matters a lot — but only to a certain point. If the end goal is happiness, money’s utility trails off after a while. The dopamine hits from buying stuff wear off fast (the hits from doing meaningful things that help people last a lot longer).

As I understand it, dopamine is more about the anticipation of a reward than its receipt.

So when you buy something, you may be excited about it and you may then enjoy it but it’s a transaction so it wears off (also why spending on experiences has a higher ROI). When you’re doing something good for someone else, the value lives on, especially if it’s an ongoing act like volunteering every week. Now, the two are not mutually exclusive. There’s no reason you can’t have nice things and help others.

That’s why the hedonic treadmill exists and is undefeated. So you need money, yes, of course, especially if you don’t have enough to afford the basics (shelter, food, clothing, health care, utilities). It’s helpful, but in and of itself, it’s not enough to guarantee happiness.

I learned this the hard way. Money was never a major focus for me personally or professionally. Power, attention and influence was. And then something weird happened. In the mid-2010s, I realized that the remaining items on my checklist — running a presidential campaign and working in the White House — weren’t things I actually wanted to do. It was good to realize that, but then I felt totally lost.

Because I was making money for the first time in my life, that became my focus. I then became too obsessed with money. Talked about it too much. Tried to make that the new definition of myself. Of course that didn’t work (other than making me look like a schmuck), because it didn’t actually mean anything.

I didn’t recover until we started doing the hunger and mobile voting work when I realized that I still cared about the same things — influencing and shaping public policy — but from a different perch than working directly in government or politics. It got even better once we added P&T Knitwear, the Gotham Book Prize and Mayday Health. And even better when I started writing books and podcasting and teaching and having a creative and intellectual outlet. But even then, still no eternal bliss.

(18) The only lasting legacy is because you did, created or changed something meaningful that truly made someone’s life better. You’re not even doing this because you’re a good person or selfless person. You’re doing it because it’s the way to produce the greatest emotional and psychological return for yourself.

That’s why there are so many miserable rich people. They miss the point, and then they double down on thinking that more status and more stuff will make them happy. It’s a little ironic that for many people who made their money because they’re good at math, when it comes to the most important equation of all, they miss the underlying precept.

Ultimately, the internal narrative matters a lot more than the external one. Of course we all need affirmation and validation (especially me). But if you only value getting it from third parties, you’ll always be off balance.

(19) If you do anything meaningful, anything new, anything different, anything hard, people will criticize you. So what? Fuck them. No one likes being judged and everyone (despite what they claim) cares what other people say about them. But if fear of criticism is your baseline, you will never achieve anything meaningful.

I spent most of my childhood just trying to fit in. It never worked. Things only changed once I realized that the way to gain acceptance was by leaning into being myself, no matter how different that was from everyone else. Since then, I’ve been able to accept that I’m an outlier in most situations. All in all, accepting that has worked well for me.

(20) Fear of interpersonal conflict is another strong deterrent to doing meaningful things. Most people don’t like adversity (I know I don’t) but ultimately, running a business, changing laws or social norms, disrupting conventional wisdom or doing anything meaningful and difficult invariably puts you in a position where you will come into conflict with someone else (usually someone who benefits from the status quo). You have to be willing to endure that.

However, I’ve also learned (the hard way, as usual) that the potential conflict with someone that you build up in your mind is usually much worse than the actual conflict, plus imagining and rehashing it endlessly doesn’t solve the underlying problem anyway. So to the extent you can just let it come and deal with it, that will make you a lot happier.

Relationships

(21) Good relationships mean finding people you like and trust and feel safe with. It doesn’t matter if it’s family or friends or colleagues or classmates or neighbors or anything else. It’s just important to have them.

I’ve made a habit of collecting friends, partly because I had so few as a kid and partly because it just really enriches my life. It’s not that hard to find common ground with people (especially if you’re curious and ask a lot of questions) and a text every month or two is usually enough to keep things going in the times between seeing someone.

The science shows you don’t need a lot of friends or close relationships to be happy (a few is enough) but I’ve also found that keeping in touch with dozens of people also isn’t that hard. It’s also why the best thing I’ve bought since I started making money was my Mets season tickets. I can bring three people to every game, so it’s a great way to see friends or make new ones.

(22) No one owes you anything.

(23) Stay away from people with a victimization mentality or people who have one standard for themselves and another for everyone else. They can only make you unhappy. Also, those people who are not actually nice but it’s okay because they’re fun and they’re nice to you? They will turn on you sooner or later. The constant victims, the blameless, the stuck, the assholes — engage with them at your own risk.

(24) How you treat people doesn’t just impact your success. The way you behave towards others shapes the way you feel about yourself.

(25) Most people just want to feel heard and seen and respected, more than even getting what they want.

(26) Ask questions. Be curious. Let people talk about themselves. It’s more interesting, it makes them happy, and it makes them like you a lot more than if you just drone on about how great you are.

It turns out the best thing about hosting a podcast is that interviewing people constantly has made me a much better conversationalist in general. But not talking about myself is still a challenge. For example, I struggled with whether or not to include hyperlinks in this document. On one hand, it’s unquestionably a form of bragging. On the other, who would want to read all of this without seeing that I’ve done enough interesting things to merit their consideration in the first place?

The answer landed on what I’ve learned in my struggle for self-acceptance. I have flaws, just like everyone. Lots of them. If those flaws are hurting other people, I need to do something about them. But the kinds of flaws that were just hurting me — insecurity, need for validation, need to seem invulnerable, need for constant achievement, need for constant action — sometimes did more harm by hating myself for them than just by accepting that it’s part of who I am. So the need to prove myself publicly is, unfortunately, part of who I am. I try to be mindful of it but I also accept it. And I included the hyperlinks.

(27) The main regrets I tend to have is if I mistreated someone. Most of the rest is just trial and error. Making amends and making sure you don’t repeat the error is very important if you did hurt someone. But if you mainly hurt yourself, embarrassed yourself, lost your own money or something where it’s a regret but the impact is mainly limited to you, just give yourself a clean slate and move on.

(28) When in doubt, show empathy. Everyone is struggling with something. If we’re all nicer to each other, life is a lot better for everyone. You feel better when you have positive interactions with people. It’s that simple. Treating life like a zero sum game is ultimately a recipe for misery, even when you’re on the winning side.

Trump, in my view, is the ultimate zero sum person. And he’s prima facie why that approach doesn’t work. He’s checked every conceivable box for being rich, famous, powerful, high status, living in total luxury, etc… And that dude is always angry and always hurt. Who would want to be like that?

(29) Everyone is making it up as they go along. Everyone. Everyone has traumas, issues, things in their past that heavily influence their judgment and opinions. Which means no one is unbiased or objective. So take their opinions, advice, views with many grains of salt. And, especially, when you’re finding a life partner, try to find someone whose issues and traumas are not inherently combustible with yours. There’s no such thing as a person without issues. But if their issues aren’t things that bother you that much, they’re a lot easier to be with than if their issues inherently trigger your issues.

(30) There is no such thing as a perfect parent. You can’t bat 1.000. You will make mistakes and fail. That’s just how it goes. When you make a mistake (like you yell at your kid when it really wasn’t necessary), just brush it off and get back up to the plate (or use whatever sports cliche you prefer here). I still haven’t figured out much of parenting yet, but from what I’ve learned over the last 17 years, flooding the zone (to keep the sports cliches going) with love, support, time, empathy and focus goes a very long way.

(31) Feel free to say no sometimes. Not doing everything anyone wants is not only reasonable, it’s essential for survival. Living just for yourself is the road to unhappiness, but so is living with a crushing sense of obligation or guilt (it’s very easy to confuse feelings of obligation with moral correctness. Sometimes they may overlap but usually one has little to do with the other. I’m finally just figuring this all out now). When you help people solely because you feel like you have to, it often makes you resentful. When you help people because you genuinely want to, it usually makes you happy.

(32) Your complaints, criticisms and judgments? No one wants to hear them. No one. 98% of the time, keep them to yourself.

Professional success

(33) Society way overvalues IQ and academic pedigree, while undervaluing many of the qualities that are far more likely to indicate someone’s ability to succeed, especially in a non-linear, non-traditional context. Yes, intelligence matters, but only as a baseline. There are only a handful of jobs — cancer researcher, quantum physicist — where each additional IQ point may make a difference. For the rest, once you meet a certain threshold, when it comes to career success, IQ is mainly irrelevant. We give people too much power simply for meeting one definition of intelligence (academic performance and IQ work best for very conventional, laddered jobs in the professional class like lawyer or investment banker or management consultant, but in my experience, that’s about it).

(34) Creativity is really important. If you can only see and do what others set out for you, your options are limited. Creativity comes into play in all kinds of ways — developing an idea, pitching an idea, turning no into yes, negotiating — every single day. “Thinking out of the box” is a cliche but if you can’t do it, you’re limited to operating within someone else’s construct. Ideally, you can both think through a concept linearly and question its underlying truth at the same time.

(35) Character matters a lot. If your underlying character is honest, consistent and stable, people can rely on that. That goes a long way.

Hustle and work ethic are two different things. To be clear, if you lack a serious work ethic, you’re already out of the game (you were never really in it in the first place). When I ran Mike Bloomberg’s mayoral campaign, I would send him an email every day at 5am laying out everything going on. When I started Tusk Strategies, we continued the practice with our clients (though at 7am). This is what I’m talking about when I say work ethic. Not just staying until 6pm instead of 5. If you’re not willing to put in that kind of work, that’s fine, but scale back your expectations and ambitions accordingly.

(36) There are many very, very hard workers who don’t know how to think about making new things happen. They think about the task at hand and then they think about the next task at hand. Hustle means seeing opportunities at the margins and pursuing them. It means taking one more shot before giving up. It means being able to pivot right when everyone else is moving left or going home. Give me someone with hustle and creativity over someone with an Ivy League degree all day long.

In my experience, talent + work ethic + courage = success.

(37) It is very difficult to have non-linear success doing what’s already been done. But keep in mind, going from zero to one is incredibly hard. Every single time. It never gets easier.

You do get a little more used to failure over time but it still always sucks. I had a really bad run professionally from 2020–2022 where I created and funded a SPAC that failed, then a tele-religion startup called Exalt that failed (to the point where I can’t even find a hyperlink for it), and then ran Andrew Yang for Mayor of NYC, which failed. It was a rough stretch.

But the reason I don’t ruminate and obsess about those losses too, too much is because I took new risks and some of those paid off. The only way to get over the failures and take new risks is through perseverance. It’s like those Olympic athletes who got up to train at 4am every day throughout their childhood — this is what it takes to truly do something new, different and meaningful. It helps to have certain skills for sure, but a lot of it is just really hard work.

(38) Being able to sell is even more important. In any business, the people who can generate revenue are simply more valuable than people who just execute really well. Whether you’re selling an idea, a widget, a company, a tv show, a vacuum cleaner, a consulting contract, a rug or anything else, if you can sell, if you can create, if you can make shit happen — your value is exponentially higher. Executors are much easier to find.

(39) Street smarts also matter. We live and work in a competitive world. Street smarts mean you see who’s going to fuck you and you stop it before it happens. You see when someone is lying. You see when something is just off. It keeps you out of trouble and helps you quickly write off people who are full of shit.

(40) Speed matters. There are professions where exactitude is required but in most cases, if you can produce twice as much as everyone else in the same period of time, you’re twice as valuable (or at least a lot more valuable). If productivity is the ultimate measure of work, then speed is the greatest facilitator of productivity. In almost every case, something that’s 88% as good and done in 50% of the time is much, much better than something that’s 98% good and took 100% of the allotted time. Don’t let the perfect be the enemy of the good is a cliche, but it’s also usually true.

(41) Ability to handle failure is critical. No one truly succeeds at everything they do every time out. If that happens, they’re taking far too little risk. The bigger the idea, the bigger the swing, the greater the odds of failure. It took us two years and countless no’s to raise our first venture fund. It took multiple factors to make us a success, but relentlessness helped get us from zero to one as much as anything.

Achieving anything worthwhile means taking the risk, again and again. It also means letting yourself feel good about the process, rather than putting all of your emotions into the result. As we saw above, the arrival fallacy already tells us that waiting to feel good at the very end rarely works, but beyond that, this is a complicated, difficult world. If you’re doing something hard to try to make it better, there’s tremendous value in that, regardless of the outcome.

I have to remind myself of this a lot with our work on mobile voting. I know firsthand how fucked up our current electoral system is. I know firsthand how technology can transform processes and behavior. I know firsthand what motivates both politicians and voters. And I’ve put a huge amount of my money, reputation and political capital into trying to fix democracy by making mobile voting possible. It is insanely hard. We may not succeed anytime soon. I get criticized publicly all of the time. But we’re trying and that’s enough. It has to be.

(42) Being non-judgmental is very important. Let people be who they are. Letting people just be is a lot easier and better than creating or living in a constant sense of tension and disapproval. If you don’t like them, don’t deal with them. This applies to every section of this list, not just professional success.

Ways to save time and get more done (this section gets very granular)

Most people feel like they don’t have enough time to get everything done. I never feel that way. Some of it is just luck — I happen to think fast, work fast, write fast — so I can get a lot done quickly. But some of it is the basis of habits I’ve developed that make me more efficient. For example:

(43) I do things right now. If I get an email or text that can be dealt with immediately, I just respond. I don’t put it off. If there’s something I know I need to do, rather than making a note to do it, I just do it. It creates a mindset of efficiency and productivity.

(44) I do as many things as possible at once. This is not a great personality trait overall and I’ve tried to be more present in general, but there’s no reason you can’t send emails during a non-critical zoom call or no reason why you can’t go back through starred emails when you’re sitting in transit. Most things don’t require 100% of your attention or brainpower. Might as well use the remainder wisely (recent science suggests my approach is totally wrong and that happiness increases materially as you focus on what you’re doing and nothing else. With that said, my approach is a good way to get shit done. And generally speaking, life is more interesting if you have a lot of interesting things going on at the same time).

(45) I don’t waste time doing stupid things. I don’t use social media (other than to tweet out a new podcast or column), I don’t use Tik Tok, I don’t use YouTube, I don’t even really surf the internet. I watch tv but solely with the intent of watching specific shows or games. I read a ton of fiction but I stop after 40 pages if I’m not into it. I listen to music or podcasts but usually while also doing something else. Doing all of the things I need to do and want to do is time consuming enough without losing more time to things that are almost objectively useless.

(46) I keep big picture lists of everything I’m doing in the big picture so whenever there is a free minute, I can go through the list and see what comes to mind, remember something I haven’t done yet, ask questions, check in, give people some attention, etc… I run through the list at least a few times a day. I also don’t end each workday until that day’s to-do list is complete, the next day’s is written, and all calls, texts and emails are returned or dealt with.

(47) Attending some things are really important like weddings, funerals, birthdays. But you can skip most stuff: galas, cocktail parties, happy hours, networking events, breakfast speeches, conferences — anything that’s mostly just a lot of small talk. There’s no tangible benefit to any of this (unless being a connector is your only true value add). I go to almost nothing and if it has hurt my career, I haven’t noticed.

I also don’t serve on nonprofit boards. I find I can be much more effective just doing things directly, whether through my own foundation or just helping organizations with money, ideas and connections. The things that boards seem to offer — status, prestige, networking — mainly feel like a waste of time.

(48) I start my day early. I wake up between 5 and 5:30 and go into a morning routine that, if I can get it all done, allows me to then be more focused and productive during the day. That typically includes working out, prayer, meditation, taking care of the pets, getting the kids ready for school, making breakfast, reading the newspapers, etc…

(49) As I’ve gotten older, I’ve realized that focusing on my health leads to better long term productivity (and happiness) than just cranking through stuff endlessly so I now, finally, prioritize sleep, therapy, going to the gym, meditation and eating (reasonably) healthy.

Now that I feel like my perspective is finally in the right place, as I turn 50, I’m really excited for the (hopefully) next 50 years. I want to make the most of them and that means investing real time and resources in exercise, nutrition, sleep and emotional health.

(50) If you can, keeping your life as compact as possible helps. For around 15 years, my apartment, office and the kids’ school were all in the same neighborhood. This isn’t feasible for everyone but the tradeoffs made in terms of space were worth it for not having a commute. I also outsource everything I possibly can. Laundry, grocery shopping, driving, reservations, whatever it is, if there’s an option to pay someone else to do it, I choose that option. My time is more valuable than money. Obviously, this only works if you have money to spare.

A few final thoughts

I was having dinner with an old friend the other night. He lives in Chicago and I live in New York so while we text a lot, we only see each other a few times a year. We were talking about what we want for our kids. It boiled down to this:

I want them to be safe, healthy and happy. I want them to find people they love and who love them — people who treat them with decency, respect, empathy and kindness. I want them to figure out what they enjoy doing and I want them to do that, either as their profession, or if not, as a significant part of their lives. I can’t make life easy enough for them to be constantly happy because they are human and they will struggle. The main thing I can do is be there for them, both proactively and whenever they need me.

I think that captures life pretty well overall — find people you want to be there for and who want to be there for you, find things to do that bring you a sense of fulfillment, prioritize those two things and you’ll mainly be okay.

There’s a lot of life we don’t understand. We probably never will. But this is the world we have. This is the chance we have. And the good news is, making the most of it is something that each and every one one of us can do.