Around a decade ago, maybe a little more, I doodled in my spreadsheet to come up with a “retirement plan.” It ultimately boiled down to a certain number of cases to win, a certain amount of legal fees to bill. This was written as something like a career goal or plan, just “the way through” until the next thing.

I did the things.

At some point I got a little sloppy in my record keeping, but the goal lines were crossed. The goals weren’t lofty, just earn enough money to retire in the most minimal way possible. It was basically around 100 cases to win, along with a billing figure that was closely affiliated with the case count. I realized, almost in passing, a few years ago while reviewing tax returns for another purpose that I had long since crossed the line of my career billing goal, and checking my list just now confirmed I had gotten there by case count as well.

There was no fanfare or awards presentation, but sometime in 2024, more than a year ago, the ten year mark of my solo practice had been passed. The numbers that would have enabled retirement had come and gone, but of course, because of spending choices, didn’t put me where I am until an inheritance put me back on track. And now I’m basically here, but with some big asterisks. The numbers just barely work. But, I’m essentially semi-retired in a very real way.

What does semi-retired mean for me?

It means I get to be pickier about the cases that I take, because I’m not desperate for work. It means I get to start working on cases that are interesting long shots that probably won’t be profitable. It means I am free to do whatever work appeals to me, across the board, including work other than the practice of law.

I am truly free and it feels like somehow at the moment, it still ends up just feeling like another thing that makes me hard for others to relate to.

There are two different ways to say no and I think it’s important not to get mixed up.

One way to say no is to turn down opportunities. and within this, I would include certain specific no’s like “I’m not good enough” or “I’m not ready” and of course the worst of all, “I’m not worthy.”

But there is another very important kind of no, which is setting a boundary. To say “I’m not going to do that because it’s not right for me,” or “I understand that is what you want, but it is not what’s best for me” is very different from saying “I’m not going to take that chance because I don’t believe in a positive future.”

I’m sure there are narrow exceptions to this general rule, but good things in life come to those who take risks, not to those who indulge only their fears against taking action.

This of course comes back to two main topics in personal psychology that I’ve been studying for the last couple years, boundaries and attachment. These two things are very closely related, because people with attachment problems usually also have boundary problems, and people who learn to set and enforce healthy boundaries usually get that skill from a basis of secure attachment. There are many excellent and lengthy books on these topics, and I can’t expect to adequately summarize them in a blog post. But if I wanted to try, I would say that the essence of good boundaries is being able to recognize the difference between what is good for you versus what someone else desires, and the essence of secure attachment is similarly the ability to be confident that you’ll be OK even if this particular risk doesn’t work out. Secure attachment enables healthy boundaries.

People seem to mostly talk about secure attachment in the context of romantic relationships, but it really does touch on just about everything, particularly your ability to take risks in life. When you are not secure, every risk is amplified on the negative side. When you look at a potential risk like applying for a desired job or pursuing an attractive potential romantic partner, secure attachment allows you to say “the downside risk is manageable, so it’s worth taking a chance on the upside risk.” Insecure attachment, or simply the lack of secure attachment, tends to make a person fixate on and exaggerate the downside potential, the negative aspects of the risk, and often minimize the upside potential. Minimizing the upside potential while amplifying the adverse side of the risk equation is a pretty effective way to talk yourself out of anything. Surefire, even. If you amplify the negative (cost) while minimizing the positive, your math will always “rationally” land on “no.”

And yet we cannot fix this just by saying “yes to all.” The “yes man” concept can be a great exercise, but it’s a learning experience only. (There is a book and a movie directly on this topic, but it’s explored in many other places.) Saying yes to everything might be a great shortcut to taking bigger risks, but it’s also a recipe for burnout and bad boundaries. Saying yes to everything can indeed mean that you take that big adventure or challenging job, but it also might mean you get stuck babysitting while someone else does all the fun stuff. You need to be able to distinguish between the “nos” that enable you to say “yes” when you should, and the “nos” that really should be “yeses.”

I am by no means any kind of expert on this but increasingly I’m receiving confirmation that i’ve learned some things worth knowing and had some not quite unique but unusual enough experiences that there are people who want to know how and why. And the how is “By saying yes when fear might have otherwise led me to a no.” Going to law school, enlisting in the Navy, going river kayaking for the first time in a February when I was in bad physical shape, and yes, accepting that case that my paralegal didn’t like (and quit over) were all risks that paid off in one way or another. And of course the potential payoff was kind of obvious: (the benefits of each is easy to guess) but the costs or downside risks are also obvious enough. Law school could mean debt and lots of work and maybe wasted years, especially if you don’t get through the whole program. The Navy could have been a great career, but it could have led to a tragic premature demise; where it actually went for me was neither of the poles of that spectrum and took years for me to see how it really paid off (and boy did it pay off). Winter kayaking was nuts, and most people still think it is, but it became the best part of my life for a long time. These are prominent examples from my own life but the list from others lives would and does fill entire libraries. 

Did you ever take a big risk that paid off? Hopefully you did, and can articulate what that was. What could have gone wrong? What could have gone right? How did you get your mind to see the upside as worth the risk? Odds are good that it was either being down enough in some way to be willing to risk it all no matter what (rock bottom), or it was having the “faith” or “confidence” or just security it took to believe that taking the risk was worth it. 

Learning to say no at the right times helps you get there. And this is probably an easier thing to see in the other direction, unfortunately. Can you recall a time when you said yes for the wrong reasons, usually a sense of social obligation or frustration, and paid for it, perhaps dearly? Can you think of another time when you instead said no to something that you felt pressured to do but knew wasn’t good for you? 

The subtlety is indeed tough. How do you really know the difference between a good no, that is boundary protection or truly rational self-care, and a bad no, that is letting your fear and doubt take the wheel when it should be confidence or faith in command? I definitely don’t have an easy answer for that either, and if i did it would probably be the “happiness project” key i’ve been seeking. And yet, what was that key? Years of research confirmed that human happiness comes mostly from good social relationships, strong connections that do not drain your energy by more than they replenish you. And this is such a hard thing to get to from a position of trauma, loss, poverty, or disability. But I remain convinced that it is possible. I would never go as far as the “toxically positive” lies that anyone can do anything, or that “If I could do it, anyone can.” Neither of those things will ever be true, at least not in general. What I do believe is true is that everyone who has a bad life could get to a slightly or significantly better life if they are able to learn boundaries and security, and that there are in fact small and concrete steps, which I would generally categorize under “mindfulness”, that just about anyone could take to make small but significant improvements in their outcomes. 

If you’ve been following my posts lately, you’ve seen me talk a bit about themes of manipulation and the neuroscience of arousal and anxiety. The neuroscience knowledge underpinning these ideas has come to me from several sources, with a prominent one being the book “Behave” by neuroscientist Robert Sapolsky. Sapolsky goes through the evidence gathered from FMRI studies and other brain imaging techniques by which the activity of the brain has now been pretty well mapped. We do not have the technology to read the actual content of neuron impulses, but what we can do is we can measure what areas of the brain are active and when, and correlate that to behavioral and cognitive outputs. Some of these studies consist of things like showing someone an image or playing a sound and measuring what part of the brain lights up. Others consist of measuring nerve impulses and response times. Studies along this line of inquiry are what led me a long time ago to reject the idea of strong free will.

Consider this experiment: the subject is stimulated with a hot touch (“hand on a stove”) and the activation of nerves and brain centers is measured. The objective measurements show that their physical response, pulling their hand away from the threatening object, happens physically before the nerve signal has had time to reach the brain. But when interviewed, the subject insists that they made a conscious choice to move their hand. This is a study that you could replicate at home if you wanted to; it’s an objective, irrefutable truth, that in at least some clear cut situations, human beings behave without conscious input and then after the fact insist that they decided consciously. This is essentially my baseline experimental input to reject the idea of strong free will, which is a phrase I used to refer to the idea that human beings act entirely out of voluntary choice and therefore can control their own behavior, and by extension are personally and morally responsible for their life outcomes. Because we often act before we are consciously aware of what we are doing, this worldview cannot be true.

So then we go deeper. Sapolsky’s book primarily focuses on the circumstances that stimulate activation of the amygdala and deactivation of the frontal cortex. What you need to know about these two brain structures is that the frontal cortex is essentially the center of both reason and empathy, and the amygdala is the “lizard brain” that acts impulsively and generally just unconsciously reacts to stimuli. You don’t think with your amygdala, it is where you act without thinking. But also, the amygdala sends signals to the frontal cortex that influence it in turn. Activation of the amygdala is essentially responsible for all of our worst behaviors. Racism, sexism, and other latent biases all come through the amygdala. This is part of why you can’t just decide not to be racist, incidentally, but that’s another chapter. The amygdala leads us to make impulsive decisions, to behave emotionally rather than rationally. And it turns out that to most corporations, all of that makes us better customers. And that idea is where I basically lose touch with society.

I have come to realize that social media is designed around the premise that an activated amygdala makes a person a better consumer of advertising. This can be phrased another way: A person who is in a state of mental anxiety and distress, aka a bad mood, is a better customer for social media platforms. This isn’t a secret; even Google won’t hide from you the actual published news articles revealing that indeed, Facebook was caught in the act of and even openly admitted to running experiments on users to stimulate a state of anxiety. This is at the core of their algorithms that determine what content you see as you scroll, and who sees the content that you post and when. And I have come to realize that this is now in all social media and essentially every social app or platform that we interact with. Ultimately, it’s about competing interests. You and the company do not have aligned interests, which is another way of saying that you don’t both want the same thing. When you go onto a social media platform, you want to get updates on the lives of your friends, be entertained, and share the stories and experiences of your life with others. But that is not ultimately what the owners of the platform want. What they want is to get other businesses to happily give them lots of money for ads, and having been on that side of things as well, I can lend you some surprising insights. First off, most ads are “pay per contact” so Facebook is heavily invested in not just showing you the ad but getting you to click on it. What makes a person more likely to click on an ad? My advertising consultant told me, back around 2019, that the best keywords to use to get clicks on your ads aren’t anything to do with the content of your ads themselves or the attributes of your particular target customer – in my case, people who were out of work and had a disability – but instead terms like “hillary clinton” and “donald trump” that simply correlated with people who tended to interact with ads more. Why is that? It’s because those topics of discussion provoke anxiety. When you go on Facebook or Reddit or TikTok to discuss politics, or labor issues, or the various ways you’ve been mistreated, you are yourself entering a state of heightened anxiety, and you are also stimulating anxiety in the people interacting with your posts. Why does the algorithm promote this content, when so much of it is vocally against their interests? The answer is because regardless of the content of the posts and comments, often stuff decrying the very problems these companies are amplifying, those posts are effective at stimulating a toxic state of mind that makes people more receptive to advertising. And they know, because they have the data that tells them that when people interact with a particular user on a group page, they become statistically more likely to click ads within the next few minutes. So, the algorithm works to promote content from individuals who provoke anxiety in others, and invites trolls and bullies to be the first to comment on posts.

This is of course the exact opposite of what you as a user want. When I go on a Facebook group, it’s often with the goal of finding an answer to an obscure question, in hopes that the large size of the group will help me connect with the obscure expert. But what happens instead is that the algorithm shows my post not to the expert who has a track record of calmly and politely explaining the relevant ideas, but instead to a bombastic bully who has no meaningful advice to offer, because the platform’s data has shown the bully does a good job of pushing other users into a mental state where they are more receptive to ads. So the parts of the experience that we as users and the mental health community feel are the worst, are actually the parts that the companies themselves are most interested in. The algorithm is directly working against your goals, directly trying to thwart you from having a positive experience, and ultimately actively and intentionally set up to harm you.

It turns out, though, that it’s not just Facebook. It’s basically any piece of software where this paradigm could possibly be applied. So games, especially mobile games, have gone from being stress relievers to little devices programmed to actually increase your stress, because that makes you more impulsive and more likely to either click the ad (they are all pay per click) or to engage in some microtransaction. And it really is absolutely everywhere on your phone; damn near every app you can get these days has ads, microtransactions, or both. The whole industry rapidly adopted that, and if you talk to individual workers at these companies, most of them will say we have to because the rest of the industry is already doing it. Where else? Search engines. retailers like Amazon, and now even in-person retailers are getting in on it as well, with a recent major newspaper article acknowledging that retailers have intentionally abandoned the old paradigm of making stores welcoming and inviting to stimulate “lingering” and impulse buys from boredom and comfort, in favor of the online data-driven paradigm of triggering anxiety and utilizing the worst parts of behavioral neuroscience to make us better customers, and worse consumers from the individual standpoint. It is absolutely everywhere.

This leaves me in a pretty uncomfortable position. What can be done about this? Many people, most people really, just accept it. They say there’s nothing to be done and it just is the way of the world, so might as well embrace it and just try to get your piece of it while you can. And I can’t do that. But what do I do instead? There’s no way for me to get the message out. Ironically, the platforms don’t mind me talking about it for one simple reason: because by talking about it, I’m doing what they want and getting people in a heightened state of anxiety. Talking about it doesn’t fix it, not directly, because for most people there is no accessible alternative. We are on these platforms because we don’t know of anywhere else to go. How are you going to stop using Google? There aren’t a lot of good alternatives. DuckDuckGo may not do as much cookie tracking, but it’s still driven by a search algorithm that is easily manipulated by marketers. You aren’t going to get meaningfully better results there than on Google; on both you will still get pages and pages of low quality chaff before you see any real quality content. And quitting any of these things is just like quitting any other addiction, except that also everyone around you is still deeply addicted and will actively try to engage FOMO to lure you back. The toxic establishments are everywhere and easy to find with prominent locations and giant signs along every road, while the less toxic alternatives are fewer and harder to find, and for the most part, reluctantly or not, engaging the same techniques on that same logic of “if we don’t do it our competitors will beat us.” And so it gets harder and harder every day to find mentally safe places to engage in basic commerce and the logistics of daily life, as well as to keep in touch with others and to stay entertained. It’s basically everywhere, pervading every corner of western civilization, in our pockets and hands, on the devices I am using to compose this thought.

I’m just not sure what to do with this information besides Quixotically try my best to share it, and I know ultimately that I won’t ever win.

I’m gonna summarize this as briefly as I can, though off the cuff because I didn’t think to prepare a post before cell service.

For years, one of the core struggles in my mental health has been dealing with social rejection. Most of us primarily think of rejection as in very specific contacts, like if you ask a person out on a date, but in fact we experience social rejection all over the place all the time and Facebook and online dating dial it up by 100. Social media is advertised as giving us increased ways to connect, but really what that translates to for the majority of people it’s just increased opportunities for rejection. Because I have 3000 Facebook friends, everything I post on here becomes an opportunity to be rejected by 3000 people at once. Completely toxic, and something I need to simply stop doing.

In truth, social rejection is completely unavoidable in any kind of setting where we encounter a lot of people. Social contact is critical to human health and survival, and like every need we have it comes with a limit which varies individually. When we hit our limit for social contact, we become incapable of having quality interactions. Most of us don’t think about this, but deal with it instinctively by altering the boundaries that we set up with people around us. This is healthy, and we should do it. It’s worse when you live in a city, because the nature of the setting forces you to interact with hundreds of people every day, and no matter how extroverted you are, you will run out of energy if to each person that you encounter on a city street you say hello and genuinely mean it. Many people don’t understand that this is happening in their lives, but it happens to everyone, and most people survive it by altering their behavior to minimize the psychological expense of contact with others. Blinders you could say; we simply avoid eye contact, often outright ignore each other, or just do our best to get through every interaction as superficially as possible. Almost all of us find this frustrating and almost everyone at some point has bemoaned the existence of the standard dialogue, how are you/fine, what’s up/nothing, etc. We all absolutely hate the insincerity of these strategies, we all depend on the strategy for survival. I had a bit of a false Enlightenment a few days ago when I thought that this was really just a reason why we shouldn’t live together in large numbers, but now I realize that it’s inherent; we will always need to find ways to survive crowded places, And crowded places will indeed be everywhere that people want to be for the rest of history. So, even though we all hate them, we do indeed have to nonetheless employ strategies to minimize the psychological cost of our daily interactions with all of these people.

Anyway, this became crystal clear to me traveling the Alaska highway and noticing that when there are fewer people around in general, we don’t work so hard to avoid each other, and for the first time in recent memory, almost nobody has tried to avoid me or brush me off in the last few days . It eventually got to a point where I had to self limit because otherwise I would be allowed to tell my whole life story everywhere I went. It was great at first being truly paid attention to, and then abruptly I hit that point where I had to start adjusting my behavior. Now it is more clear to me than ever before that I do you need to tell my stories, in full length, but on paper, and books and magazines and the like, and actualize my reality as a writer and not try to pretend to fulfill that need through another channel that wasn’t designed for it, a channel such as social media. I’m not gonna go quite as far as calling this a goodbye post, but lately every time I touch Facebook it becomes clearer that it is not the right place for me. I believe that Facebook is very intentionally optimized to be as toxic as possible, to very specifically overwhelm us with too much stimulus and simultaneously make us feel chronically rejected and keep us filled with a sense of longing for more. I am not speaking a conspiracy theory, this is very much the truth about how Facebook is intentionally designed for “engagement” and well-documented. It’s like a cigarette, it is meant to be bad for you.

So what’s the answer? First off, less of this. Instead, talk to your actual friends. Make a phone call, send a text if that’s all you have, visit someone in person if you can. Stop scrolling, stop checking for likes, and stop posting to places where nobody really wants to read what you have to say like groups we’re a lot of people or just they’re looking for fights because that’s how they get a sense of feeling recognized. And yeah that’s on purpose as well, Facebook is designed to get people arguing because apparently arguing is “engagement“ and that’s what sells their ad views. It’s not designed to inform or connect, it’s designed to addict and enslave. So, though I know that three or four of you have been wanting to use this to follow my journey, I haven’t been posting much largely for these reasons, and I’m not sure that will change. I do have messenger on my phone, and if you genuinely want to keep in touch, use that to send me other contact information. I won’t be deleting Facebook specifically anytime soon because it is a business necessity like it or not, but soon enough I will be converting my personal page to a professional page simply in order to help me reduce my emotional responsiveness to the lack of engagement when I post. I remain present all over the Internet as @Whitewaterlawyer including that with a .com, and who knows how soon, but eventually you will be able to find me at your local bookstore and on Kendall with a couple of titles specifically on the way. There will be a memoir of the 50 state journey and there will be a short essay book with a title similar to “everything I wish you had learned in college but didn’t.”

Otherwise, you know where to find me.

How embarrassing, it looks like my last post here was as I was wrapping up my first van life experiment, almost two years ago.

And it really wasn’t fair of me to ghost the page because there really was a lot going on over that time. I never really recapped the big 2020 road trip. I said nothing at all about the winter 2021 Grand Canyon kayaking trip. I didn’t share my learning experiences from a short-lived fast fire romantic relationship that overlapped with the GC trip, either. And then I’ve left this page in the dark – in favor of Facebook – about the latest stages of my journey.

Really, the truth is that I’ve mostly moved to my personal Facebook feed as my main online social outlet. In a lot of ways it’s just more convenient, if only because I know people are actually reading over there. This page gets very little feedback so I really don’t know who is reading it, and yes, I am an attention whore and crave feedback.

Anyway, here’s a paragraph on each of those events in case you need to understand my whole story just from this page.

A Facebook friend invited me to join him on a winter trip down the Grand Canyon last winter. It was the second time he invited me, the first having fallen through because I just had too many hearings to be able to keep the time off without doing serious financial damage. It was 18 days of paddling 228 miles in late January into February, ending the day before my 40th birthday. A month before that, I got a Facebook message out of the blue from someone who said she read this page and wanted to get to know me. Turned out she lived in Flagstaff, so I said let’s be friends so I don’t have to spend my birthday alone while on the road home from Flagstaff. We made a plan to meet up at the start of my trip, and we clicked. We texted on my InReach during the trip (I know, I shouldn’t have) and then dated for another couple months after. It ultimately didn’t work out so well, initially because of logistics but ultimately we just weren’t on the same timelines; she ended up marrying someone else within four months, which incidentally is the second time I’ve had that happen.

Anyway, the one good thing that came of that, apart from a lot of soul-searching about what I should be looking for in a mate, is that considering a cross-country move forced me to take a critical look at my finances, which were in bad shape. I made some tweaks in my life after that and did make some huge strides toward paying down debts in the last year or so.

Now, I’ve had another birthday and am now solidly “in my forties” which I guess is even more middle-aged than 40 was. And I’ve come to feel really acutely self-conscious about not being where I want to be. Where am I? Mostly stuck in Buffalo, working a lot but not really working that effectively, not traveling that much and paddling even less. I’ve only paddled 16 times this whole year so far, including pool sessions; I had that many just during the Grand trip last year, and indeed this is the lowest day count I’ve had YTD a third into the year in, well, years. And I’m just plain not happy. I’m socially isolated. My depression is pretty consistently bad. I don’t really feel like anything is really going that well. I feel like I’m stagnating, and I feel trapped.

I started really feeling this way more acutely around my birthday, but honestly it’s been brewing for a long time. I announced, to a limited audience anyway, my intention to make a bold move and exit Buffalo, selling my house and maybe heading to the Smokies, ideally buying some land right away. In the last couple months I’ve done a lot of research including a lot on the real estate side, and well, the numbers aren’t working. I’m not well-situated to get a mortgage right now, and while there is some land I could afford after selling my house, nothing I can afford is really that ideal for how I want to use it. And I haven’t quite worked out making my firm operate at full-capacity while I’m on the road. I thought I had, two years ago, but now I’m more attuned to my professional deficiencies and growth areas.

I’ve gone back and forth on folding my firm altogether to “retire” to full time nomadic life, or going nomadic while doing exactly the same work remotely, or at one point, maybe just staying the course a little while longer.

Here, by the way, is the argument for staying the course a little while longer: Over the last year, while working hard at the law practice and side hustling with rideshare, I’ve paid off or helpfully restructured almost $50k in bad debts. If I stay the course, I’m about another year I could finally have a decent financial profile with very low monthly expenses and a credit profile decently compatible with getting a modest mortgage and building my dream homestead/campground. Real estate prices have a fair shot of staying in a similar range over just a year or so. And if I am very careful with my practice, I may be better situated for a mortgage in terms of documented income, as well. However, it would look like capitulation; it would be going back on a commitment I made to myself to, basically, just fucking do it already, as I’ve been putting it off for too long.

The god’s honest truth of the matter is that waiting a while does make a lot of rational sense. My income is higher running the firm full-time and more hands-on. If I rush to move without tolerating distractions, I won’t really paddle much at all this summer, instead spending that time and money on logistics. And anyway, none of the classes I need for the next phase – more on that later – are even offered over the summer anyway, so leaving now versus in the fall doesn’t really help me, and finally I have made some tweaks to my practice that should allow me to travel and paddle most of the summer.

So, I guess we are kind of embarrassingly back in a kind of holding pattern, but that’s okay. This is going to be take three at the travel life, post-pandemic edition. I’ll try to keep you updated a little more than last year.

Oh, and I got a drone, so that’s kinda fun.

I know I haven’t posted in a while, but I’m going to resist the temptation to update you on all the developments of the last two years. Instead, I’m going to focus on the findings of my research.

As most of you know, my main drive in life is happiness, and I’ve spent the last decade on a quest to discover the keys to a happy life. I started by figuring out what happiness isn’t – and I think most of us who’ve put serious thought into it already know that. Happiness isn’t simply “the American dream” of a great career, material wealth and possessions, and an impressive spouse and family. All of those things are nice, yet we all know plenty of people who’ve checked all those boxes and are still miserable. Hell, people have been writing songs and novels on that very thesis for decades, maybe even centuries. For some reason, all the trappings of conventional success are not a guarantee of happiness. Now to be clear, they aren’t likely to necessarily hurt your chances of being happy; many happy people live very conventional lives with fulfilling careers, significant wealth, and conventionally impressive families. But we all know that won’t make you happy. 

So what does? My serious question for happiness began in earnest at a precise moment, essentially during my winter job during my second year of law school at the end of 2011 and beginning of 2012. That’s when I realized my attempts to live the life I imagined others wanted me to live were a failure on all fronts; not only wasn’t I achieving it, it was a bad goal in the first place. At that time I came out to my family and my few friends about my mental illness, set boundaries with my family I’d never set before, and adopted a “yes man” mentality with a decision to start affirmatively doing things that I wanted to do and not let anyone tell me what I couldn’t do. And honestly, it worked pretty well for a while. I learned a lot about happiness and I definitely became much happier. But I didn’t get all the way there. I can say now that my decision to prioritize recreation over work in an extreme way was not a winning strategy for happiness. In the end I ended up failing at both; I didn’t become a world-class kayaker or even really a respectable athlete, I didn’t find a way to make a living kayaking or life coaching, and along the way I neglected my career and worsened my long-term financial standing. So my new thing is recognizing that path as a well-intended failure. Happiness, it turns out, is not as simple as just doing what you want to do all the time. So what now? What is the next evolution in my pursuit of happiness?

I’m writing this from my rental car outside my workplace in West Palm Beach, enjoying a nice break from Buffalo’s bleak weather, and engaged in one of the practices I think I have kind of figured out: optimizing my work situations to allow me satisfaction and productivity in my work while simultaneously and consequently creating enjoyable life opportunities. What exactly am I doing right now, and how does it fit in on the path to happiness? Well, for one thing, I’m fulfilling multiple “values” at once. I’m helping people, I’m making money, I’ll be getting some exercise shortly, and I’m having fun. I’m living the dream of doing what I love vocationally and having fun along the way. One happiness theorist I’ve spoken with privately would say I’m creating a mutually beneficial experience to satisfy several of my priorities at once. 

I just read a book called “The Subtle Art of Not Giving a F-k.” I’ve actually read a lot of self-help books on happiness, including some that weren’t even published that I came across in my research. I’ve found a lot of common themes in them, and let’s distill it a bit. What themes do most “happiness experts” agree on? We could maybe think of these as tried and true rules to happiness, but I hate the idea of setting up rules, so let’s just call them guidelines or principles. 

So the first principle that most happiness experts seem to agree on is intentionality. Regardless of their personal frameworks, happiness experts all agree that a happy life is derived from intentional choices. We could also call this volition. The dictionary calls that just “the faculty or power of using one’s will.” I most concede that there are some, particularly in the religious frameworks, who claim to reject the idea of self-direction and personal choice, but I don’t think they’re even being internally honest with that. 

You have to make a lot of intentional choices to be happy. You have to choose your metrics. You have to choose your priorities. You have to choose what matters and what does not, and who you will try to satisfy and who you will ignore. Some theorists seem to believe that the very act of making a choice is the critical element, but most agree that choices matter because of how happiness is personal. 

And that’s the second principle: happiness is personal. My advice is limited in value because what works for me may not working for you, in several ways. For example, if I told you the key to my happiness was creating a work situation that created recreational opportunities and facilitated travel and hobbies, it would be bad advice in two key ways. First, and most gurus miss this, this particular pathway simply isn’t an option for many people. I’m extremely fortunate, and a common mistake among gurus (lookin at you Tim Ferris) is assuming that everyone has the same resources and opportunities. We don’t. The universe gifted me with a string intellect and a demographic background that allowed me to get a great education, and dumb luck landed me a flexible career. But I could just as easily have been stuck in unskilled work, or even disabled like the people I usually work for. For those people, advice derived from my career would be worthless. No, your path is going to be different from mine in many ways. We have to distill the fundamentals that can be translated, and honestly that’s the hardest part of happiness coaching. I can give you broad principles, as can a lot of authors, but we simply cannot come up with a plan for you. It’s got to be personal. 

What else? The third commonly held principle in happiness research is priorities. You simply have to decide what does and does not matter to you. This is really just a fusion of the first two principles, so maybe I’m wrong to call it a third. The beauty is there are no strict rules, and there’s no authority on this either; I’m merely trying to help you find some principles. 

I’ve got to level with you on my results. As I said, I’ve been working on happiness for a decade, and part of that for me has been managing clinical depression. A big mission for me has been to prove that you can be happy even with mental illness or disability, and yeah, honestly, it’s hard sometimes. So maybe another principle we could add about happiness is that it’s hard. I know that sucks. I know you want an easy way. I can’t offer you one. If it exists, I haven’t found it. Anyone who tries to sell you an easy path to happiness is lying to you, they’re manipulating your desires for personal gain. And I don’t know, maybe they really think it is easy, because it was for them, because they got lucky. I’m probably the least successful person you’ll encounter in the happiness world, and yet here I am, broke and struggling in my businesses, slipping into crippling depression from time to time, and making a literal career of complaining about stuff not working out for people. That’s all true. And yet… I don’t think I’m failing in my quest for happiness.

That’s my final revelation: that it’s a process, not a destination, and yes it’s entirely possible to be happy through suffering and failure. So that’s principle four: it’s a continual process.  It’s not about arriving somewhere.  It’s about how you live day to day.

I’ve written or said quite a bit there so I’m going to cut it off now and call that today’s overview. Tell me in the comments section where you think I should go with the next post. Tell me if there’s a point I should elaborate on, or I guess you could also tell me if you think I’m wasting my time here. The bottom line is that you’re going to have to figure out your own ultimate answers and your own process, but I want to help you however I can. 

Who’s Ready

My major new project for 2019 is a new social networking app called Who’s Ready.  I’ve got a whole web site set up about the app, at www.whosready.app, along with a facebook page at facebook.com/whosreadyapp, and some other social media as well.  So I don’t have to tell you everything about it right here, but maybe I should tell the story of how it came to me.

If you’ve been following this page or the other places where I narrate my life, you know that I travel a lot and that my main passion in life is outdoor activities – mostly whitewater kayaking, but a few other activities as well.  Whenever I find myself in a new place I want to get out and explore, at least go for a hike, and I often wish I had company to do it with.  I struggled for a while using Facebook groups to find activity partners, but I find the solution woefully inadequate for many reasons.  I wanted a way to just push a button and find nearby like-minded adventurers, and didn’t understand why in 2018 there isn’t an app for that.  So, I decided to build it.  My financial situation improved somewhat in 2018 and I finally had the ability to start financing other projects beyond my law process, albeit just barely.  So I wrote up a complete design spec for the app, worked on finding a name (a more difficult process than you might imagine), went looking for a programmer, and formed a corporation.  I found a programmer who could build the MVP version of the app for a price I could afford, and set up a contract.  At this point we’re behind schedule but hopefully within a week or two of having a product in the Google Play Store, and within a few months we’ll be on the iPhone as well and charging forward with more features and a viable business model.

I’m excited and terrified about this new venture.  Once again, I find myself in a role I’d fantasized about but had never visualized actually achieving – first that happened with my career as a lawyer, and now with the role of “software CEO.”  Wow.  Of course any fool with a checkbook and a pen can become a CEO by starting his or her own company, it’s meaningless until it translates to actual success, and we just aren’t there yet.  There’s a lot I’m going to have to do to get this thing off the ground.  Building it is just step 1.  I also have to market it and get people to use it.  Because it’s a social app, its success and utility are 100% dependent on how many people decide to download and use it.  It will be more fun and more useful with a million users than with a hundred users.  So my job, and it’s a big job, is to accelerate the growth of the user base as quickly as I can, to create a great experience for users.  That means advertising, attending events, and talking to people.  It’ll be fun, but it’ll still be hard work, and there will be a lot of disappointment and frustration along the way.

I’m super stoked about it.  Check out the web site and Facebook page today, and hopefully by the time you’re reading this you’ll also be able to download it on the App Store of your preferred platform.

Some of you may have heard of GoRuck. They make backpacks, and to sell more backpacks they invented the sport of “rucking” and started hosting “GoRuck challenge” events in various cities. So they’re known among the adventure/obstacle racing circles and have been on my radar for years. Their bags are highly optimized for air travel, sized well to serve as carryons, particularly for “one bag” travel.

Considering how much I fly, I’ve wanted one for a while. So when a little bit of unexpected money came in a few weeks ago, I decided to indulge. With free shipping and the military discount, their flagship GR1 bag came to about $225, a sum I could reasonably manage out of my recent “found money” pool. I received the bag and excitedly packed for my first travel ordeal with it, a series of single overnights back and forth between Western NY and the south.

Sadly, the bag underperformed, although by only a little. It turned out that an overnight business trip with my recreational items added (suit, dress shoes and hiking boots, dress shirt, change of base layer, toiletries, laptop, chargers and cables, other electronics,bathing suit, towel) just barely fit in the bag, not leaving room for food, and with some access and organizational problems.

Of course the solution was obvious: upgrade to the slightly larger GR2 bag, which has the same height and width but is much deeper, yet still supposedly sized to fit under an A321 seat. I decided to upgrade my bag, but since I got such a great deal on it, it made more sense to resell than return. I listed it on Reddit, priced modestly at $15 more than I paid for it, plus shipping. I got a few replies but one intrigued me: would you trade for a 34l GR2? Since that was my exact ultimate goal, it was a resounding “hell yes.” So we started planning the exchange. But how do two adventurers swap gear without meeting?

A few ideas were floated but none that solved the trust problem. I could cover shipping, that’s fair since I’m getting the better deal, but that means I’m shipping my $300 bag to a stranger in the blind hope that he ships it back, with no real recourse if he doesn’t.

He texted me from a number that my phone identified as “San Francisco.” That was a little intriguing if unsurprising; seems like half of Reddit is from the Bay Area. But so are a few of my friends. Real friends I haven’t seen in years. And I was just sitting around wishing I was on a trip in my RV, but stymied by a waiting period on a loan. So I posted to Facebook and messaged people, checked JetBlue, and sure enough I could throw together a trip on miles. So I headed to San Francisco to trade backpacks.

The trip was not without snags. Delays stacked on delays and eventually I arrived at SFO around midnight – apparently after my rental car agency closed for the night. There was one agency left open, and by my math the line would be going a good three hours, assuming they really had a dozen cars. Dan messaged me on Facebook. “You okay? Need rescue?” Yes. So I took a $35 uber to his place, listening to Muslim propaganda along the way in a car with disturbingly detuned headlights.

And Dan and I talked well into the night about all the things we needed to talk about, and it was good, and then I left for three hours on a quest for a rental car that involved some walking, some Starbucks budgeting, a train, a good deal of hiking, and finally a “fuck it, I’ll get an uber” for the last four miles. Then a hell of a shuttle, then another line, then a Jeep, and then hauling ass to the drop point.

Louis was waiting for me at the mall. I don’t know Louis, but we’re social media friends now. He wears scrubs so he must do something medical. Maybe he’s a doctor but I didn’t ask. The exchange now included a second bag, a GoRuck Bullet, and cash. We swapped, played with Venmo on our phones, and parted ways.

I had a few small missions planned in San Francisco proper. First lunch, at a little Mexican place Louis recommended. Good burrito. Next REI to exchange Christmas socks (wrong size) and top up camping gear – a way to secure my sleeping bag to the GoRuck and some camp fuel. Then Safeway for groceries- apples, granola, beef jerky, and of course water and beer. Then the road to Yosemite, showing… 6 hours? How did it go from 3 to 6? I underestimated traffic it seems.

So instead I decided to meet Gabe last night and embark to Yosemite during daylight the next day. Gabe told me about a place for a little hike along the way where I could try out my Bullet Ruck and not skip leg day. I logged just two miles but caught a beautiful sunset in a surreal pasture of hills adjacent to affluent suburbs. Feasted on In-n-Out burgers, then sleep.

Work woke me this morning as usual. I spent some time on various obligations and felt productive. I’m not really on vacation after all; I worked in the airport and on the plane and wherever else I get the chance. After all the nominal purpose of this mission is to make future business trips more efficient. After work and another gratuitous shower I got an indulgent California breakfast ?$15 pancakes) and headed east.

I finally arrived at the park gates at 4 pm, and received my coveted lifetime pass instead of paying. And was told that my plans were all wrong. I would need to head to the valley campsites and hope there was a spot left. There was, and I walked in the door for it at 4:58, the nick of time. I found the spot and quickly took off in search of a trailhead. Hiked through the sunset and got some mediocre pictures, then to camp to set up.

It’s funny how sometimes the best parts just don’t translate well to writing. That short hike was powerful. And yet it was private. It was my own experience, shared perhaps with millions judging by the well-worn rocks. I came back rejuvenated. What have I been missing? This is something I needed. I am glad I came.

So I came back to the campsite and set up my hammock. Had some challenges with equipment failing but in the end it worked out. I crashed a campfire and chatted with a couple from Berkeley who come here often; they gave me a drink. I needed sleep and took it, and I am now recovering from my second wind with the help of Ambien. Goodnight.

One part of my work that I really enjoy is traveling to cover cases all over the country. This is usually a service I perform as a contractor for other attorneys when their clients move to a different area, but I sometimes encounter the same need for my own clients and do it myself. That means I go on a lot of very short business trips, as little as 24 hours, and I fly a lot more than most people, often twice a month or more.

So let me share some tips from a frequent flyer. Note that your needs may be different from mine, but for the attorney on business travel, this should be a helpful guide.

Luggage

Most airlines allow travelers to carry two bags on board the plane, and require additional bags to be checked to the baggage compartment, usually for a fee. Checking baggage is a hassle and a risk, so I try to avoid it except in special circumstances like a long trip or if I’m bringing bulky gear like kayaking or skiing equipment.

Most frequent flyers use rolling luggage as a carry on, and if that’s what you want to do it’s not hard to find good luggage suited for the purpose. However, I have found rolling luggage to come with a lot of downsides, and after years of trial and error I’ve switched to using a backpack instead. Why a backpack? The main reason is that it’s much easier to carry around the airport, especially if you need to run which is inevitable once in a while to make a short connection in a large airport. The next advantage of a backpack is that it more easily fits into the smaller overhead bins common to the smaller airplanes that fly into more remote airports. Finally, since backpacks are less common on planes than rolling luggage, it’s much less likely that someone else will accidentally take your bag.

Now, backpacks vary a lot, and it’s easy to spend a fortune on a good travel backpack such as the GoRuck GR1 or GR2, but I haven’t found that necessary. What’s nice about the GoRucks is that they are shaped like conventional rolling bags, which makes them easy to pack and they hold a lot, but I’ve found that a simple student-type backpack is more than sufficient for most trips. I use a low-end North Face bag that I bought for $30 at a climbing festival. Before that, I was pretty happy with the Eastpack school bag I bought for college in 1999. A large backpack holds more than the largest rolling bag that would fit in the same space, but can be stuffed into a slightly smaller space, so you can freely use a relatively large day pack. I don’t recommend larger “backpacking” backpacks, but they may be acceptable for longer trips.

The second bag should be some variation of a laptop bag. I use a courier bag from REI that provides good storage for a laptop and basic business needs and then some. Check with your preferred airline for recommended dimensions and ideally get something that fits your volume needs but still fits under the seat.  I don’t personally recommend spending a lot on this bag, but to some professionals image matters, so buy whatever you like.

What to bring

Again this is assuming a short overnight business trip of just a day or two.

In the backpack or rolling bag:

• Change of clothes (base layer) and work shoes
• Hygiene supplies – some like to rely on what hotels provide, but I prefer my own shower supplies so I bring that in a ziplock bag, along with toothbrush and toothpaste, nail clippers (you never know), a small bottle of mouthwash, and optionally a small “sample” bottle of cologne. Personally I don’t shave, but if you do, bring just a razor; most hotels have shaving cream available for free. Oh, bring deodorant; hotels rarely have any to give you. I get my toothpaste from the hotel front desk periodically; I have never bought a travel tube of toothpaste.
• Recreational clothing – most trips include at least a few hours of downtime and I prefer not to spend that wearing a suit, so I tend to bring comfortable clothes if I don’t wear them to the airport (see below). I usually bring a bathing suit as there’s usually a hotel at the pool even if it’s not a beach destination, and I’m often traveling from Buffalo in the winter. Bring your own towel if you’re planning a beach trip; you may not be able to use one from the hotel depending on your checkout time.
• Sandals – flip flops are great to wear in hotel showers and to the pool or beach.
• Medication – if you are reliant on any kind of medication, I recommend keeping a few days supply in each of your bags.

And that’s it for the backpack, unless you have a special need or desire; there are no set rules here.

The smaller courier/laptop bag

The second bag that shows under the seat in front of you is more critical, and I try to fit as many of my essentials in it as possible.

Your mobile office – for me, this consists of quite a few items:

• Laptop (in a neoprene sleeve)
• Laptop power adapter and cord
• Portable scanner – less essential now that phones can scan but still nice if you expect to receive documents
• Power cords and adapters for phone and headphones, and for your smart watch if you have one
• Flash drive (several in my case)
• Any adapters you might need (especially if you have one of the newer USB-C laptops)
• Any paperwork you will need for the trip – best to print it in advance as hotel facilities are unreliable

Other electronics:

• Bluetooth or wired headphones- these are really essential for longer flights
• Portable power pack – every frequent traveler should own one of these. You’ll use and rely on your phone more while traveling, and if you use Bluetooth headphones they could die over the course of several flights. If you don’t have one, grab a cheap small one on Amazon, but get one big enough to charge your phone a few times.
• Car charger – I use a dual USB lighter jack adapter to plug my phone in to the rental car. It’s less essential now that most cars have a USB port, but you can’t rely on that as you never know when you’ll be stuck in a 2013 Elantra.
• Aux cord – in case you get stuck in a car without Bluetooth. Most of them at least have an aux port.
• Vent clip phone holder – to hold your phone in view in the rental car for navigation

Optional electronics:

• Kindle or tablet- I used to carry these to use in flights, but I don’t anymore. I now consider it dead weight but if it’s worth it to you, bring it.
• GPS unit – I use my phone, but if you prefer a stand-alone unit it may be worth the space and weight to you.
• Ezpass – it’s not a bad idea to get a spare to keep in your travel bag. In certain areas this will save you on tolls versus renting one from the rental car agency. On the other hand it really sucks if you forget it in the rental, and the more you have in the car the more you can forget.

I don’t carry these last few items, because for my needs it’s better to keep it simple, but do what works for you and you decide what’s worth carrying.

Clothes: I pack my work clothes in my work bag for a few reasons. They’re less likely to get wrinkled there than in your backpack, and this bag is less likely than the bin bag to get lost or stolen. If you lose a bag, you want to minimize what you need to buy on site, and the last thing you want is to be scrambling for a replacement suit at 8 AM before work.

So my suit pants and dress shirt get folded and go in my courier bag. I put them in a plastic grocery bag for more protection. My tie also goes in this bag. Socks and base layer go in the other bag; in an emergency I can just keep on what I’m already wearing.

Medication: you should have a few days supply of any essential medications in each bag, including “PRN” medications, and OTC essentials like Advil or Aleve and motion sickness pills if that’s your thing. Imodium and antacid are a good idea too.

Secondary ID and form of payment – Losing your wallet on the road is a nightmare, and in some cities and airports business travelers are targeted by pickpockets and muggers. I keep my passport and a backup credit card in my courier bag.

On your person:

Clothing- I dress oddly for transit. I wear my sneakers, comfortable casual pants, a t-shirt, my smartwatch, sunglasses, and my suit jacket.

Why the suit jacket? It’s almost impossible to stuff it in a bag without wrinkling it, short of using an absurdly bulky and expensive garment bag. Plus it has pockets and comes off easily, so it spares me from having to unload pockets at airport security. Trust me, this will save your time. And it’s a cool look.

In my wallet I have the two most essential “optional” items: my Nexus card for the TSA Precheck security line, and my American Express card.

I can’t sing the praises of TSA Precheck enough. You can buy into it as a stand-alone product for $25 a year if you have an enhanced driver’s license, but you get it for free with a NEXUS or Global Entry card, which is just $50 every five years and also speeds you through the US ground border crossings.

Similarly, I can’t get over American Express for business travel. Which Amex is right for you is a whole other article, but I am not aware of any card that beats them for transaction tracking, fraud protection, travel perks, and loss protection. My favorite feature for business travel is how easy the web site makes it to generate expense reports for client billing. If someone else is paying your bills, there’s no other card that comes close. And if you get one of their premium cards a lot of other perks kick in, like free rental car insurance, life and injury insurance, travel bookings, and of course reward points.

I don’t travel with much cash at all if I can avoid it, but if it makes you feel safer stuff a few 20 dollar bills in a hidden spot in each of your bags. A little cash is nice to enable things like eating at street vendors, but I seldom need it, and for tracking purposes I prefer to spend every dollar of a trip on the Amex anyway. However it’s a great idea to have a few dollars in quarters in your bag for city parking.

And that’s about it. If you use this as your packing list for business travel, you’ll be lean and fast at the airport while having everything you are ever likely to need.

Lifestyle design is a phrase I stole from Timothy Ferriss’s book “The Four-hour Work Week.” It refers to the idea of taking charge of your complete life and living a lifestyle that you’ve actively designed rather than simply following along with what society or your family dictated for you.

I’d actually been working on lifestyle design for a while, but I was drifting aimlessly until encountering a few key events and people. I began thinking of lifestyle design around Christmas of 2011 when I realized that my life at the time was a joke. I was a second year law student with no real hobbies, no close friends, and seriously troubled relationships within my family. I was also morbidly obese and in denial of some slowly deteriorating health conditions as a result.

The first encounter that started moving me toward lifestyle design at that point was a legal colleague at the firm I was working with at the time, a fashionable and motivated young lawyer named Will. Will was doing ordinary work at a mediocre firm, but he was clearly very good at it, and he loved what he did. It was clear that he loved his life. He was always well-dressed and had a great attitude. I learned a little from him about the law, but really his main influence was to make me envious of his personal fashion. I realized that certain factors were holding me back from dressing like he did and carrying myself with confidence.  Will was also a model of lifestyle design in other ways; he created his own employment terms at the firm, working from home more often than not and setting his own hours, and I would later learn that the firm was a deliberate step in a planned career that would take him to running his own business on his own terms.

The second encounter was with my own father. Some details are personal, but a family crisis made me realize how much of my life I’d been basing on what I perceived as my family’s expectations of me. Christmas 2011 was a minor family crisis that forced me to reevaluate some of those relationships, and somehow it was enough for me to realize that passively accepting these relationships without personally dictating terms was holding me back. So I made a minor adjustment and started including my own interests in the terms of my personal relationships. That is to say, I started setting boundaries and asking that my needs be met.

The third encounter was with a law school classmate. When I returned to school for the spring semester, I took some small steps myself toward developing a healthier lifestyle, like buying a new bike and starting to ride it in the snow. I’d been thinking for years about getting back into skiing and kayaking, since I lived close to places to do those things, but I hadn’t done them for some reason. A few weeks into the semester I met a girl who casually mentioned that she did these things, so I jumped on the opportunity and started doing them with her. In the long run that friendship didn’t work out, but I will never forget the role that she had as a catalyst of lifestyle change.

At that point the pattern of meaningful encounters was set. There were more, many more. The guy who got me into adventure racing. The people who taught me the basics of whitewater. A few lawyers, a few women, a financial guru, and a number of people living lives I found enviable.

When I met Eric Jackson, I was primed and hungry for more information on lifestyle design. That’s why I asked him for his book – and why he shared it with me. I started with that manuscript and then started doing what all competent writers must do: reading. I devoured every lifestyle-related “self help” book I could find. I also focused my podcast habit more specifically on “life hack” topics.

Some of the books that I read and at least somewhat recommend included:

• Malcolm Gladwell’s Outliers and David and Goliath
• Nick Offerman’s Paddle Your Own Canoe
• Timothy Ferriss’s The Four Hour Work Week
• Steves Levitt and Dubner’s Freakonomics (and the podcast)

And a few others. I also added a few podcasts such as Hidden Brain and How I Built This, and started watching and listening to TED talks. Recently I’ve also been reading and listening to some financial people who talk about early retirement and moving to a “work optional” lifestyle, mainly Mr. Money Mustache.

All of these sources can be distilled to one sentence: To live the life that you want, you need to zealously focus on what you really want, and be willing to sacrifice everything else to get it.

You don’t need to read or listen to anything on this list if you have it in you to do that.

So that’s lifestyle design in a nutshell. I talk about it a lot. I scare women away in bars bringing it up. I sometimes inspire and sometimes annoy by obsessing about it. But it colors my choices and why and how I do the things I do. It is simply about designing the life that you want to live, and then committing to live that life.

And on that note, it’s time for me to take a break from writing, do an hour of real work, and go to the beach.