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. 

When you hear the phrase “supply side,” you probably think of Reagonomics and “trickle down theory.”  And if you are on the left, you’ve probably observed that it doesn’t really work.  As an economic stimulus policy, “supply side economics” is the idea of stimulating the economy by lowering taxes for the sellers of products and services, in hopes that it will “trickle down” in the form of various kinds of spending that results, in terms of pay to workers and supply chains, in more people getting paid.  It doesn’t work, though, because economics doesn’t work that way.  People who have money choose to invest based on demand, not based on their own resources. Lowering costs does not lead to producers producing more, it just increases the surplus that they can save.  They still behave as rational econs, producing only as much as they can profitably sell, and selling it at whatever price the market will bear.  All economists know (but many won’t say out loud) that stimulative economic policies are more impactful when the money is given to poor people, who always spend it all back into the economy.  

In terms of drug policy, when I say “supply side” what I mean is that the efforts of law enforcement are more focused on trying to disrupt the supply chains of harmful products, rather than focusing on measures to reduce the demand for them.  For example, they spend money on policing the national borders for potential drug imports, and on policing regional and local drug dealers to break supply chains.  These efforts don’t work in terms of economics, though, for a simple reason: supply follows demand.  When they consumer still wants the product but a supplier has been disrupted, the consumer will just go to another supplier.  If the volume available for sale is decreased, then the remaining suppliers will raise their prices, and the rise in price will increase the incentive for someone new to start producing or importing.  The market self-corrects, and the supply chain is always restored after the momentary disruption.  The only real effect is that a few individuals suffer along the way.  But the effort never actually leads to “less drugs in circulation” in the long term.  Instead, it just increases the magnitude of the school to prison pipeline, as “drug dealer” remains the most lucrative opportunity for many young people.  The supply side approach to drug enforcement is ultimately a jobs program; it keeps the turnover rate high among drug dealers, such that the economy is always hiring for that position, and also gives police officers and prison guards, who might otherwise be violent criminals themselves, justification to be employed by the government.  

If we as a society actually cared about drug abuse as a systemic problem and wanted to really solve it, we would be better served to address the demand side, which means a few things that we don’t want to talk about.  Of course we start with treatment programs and alternative medications like Methodone, to give addicts a physical pathway out of addiction.  But what we should really be doing is addressing root causes.  There are really two main causes of substance abuse and they are poverty and medical problems.  We could fix many substance abuse problems by giving people a worthwhile reason to stay sober, like a good job or academic opportunity; and we could solve many more by giving people easy access to quality healthcare to actually troubleshoot and treat causes of chronic pain or mental illness, rather than leaving people to self-medicate in potentially harmful ways.  Of course, solving our national mental health crisis is not as simple as just passing a funding bill to put one extra therapist in every town free of charge.  Our mental health crisis isn’t from a lack of therapists (though that exacerbates it).  It’s from a culture of scarcity, competition, and relentless demands on our energy.  It’s from social media and pop culture that inundates us with fake connection and makes it harder to get our basic needs for love and belonging actually met.  It’s from cultural messaging that gives people endless reasons to feel inadequate or unworthy, and too few pathways to meaningful fulfillment.  Unfortunately, none of these things is trivial to solve, or even to show progress within a single elected term of office, so our system of “accountability” that punishes politicians who engage in long term policy planning prevents us from even trying.  

Incidentally, all of this applies to guns as well as drugs. While some categories of gun crime can be reduced by adding friction to the purchase process, determined criminals are seldom deterred by a mild inconvenience in having to seek a different supplier, and as long as the demand is unchanged, a black market will always arise to fill that demand. This is especially true when supply constraints are only regional, such as restricting gun purchases in New York but not in adjacent Vermont, or Illinois but not adjacent Indiana and Iowa. We would get more consistent results if we turned levers on the demand side and reduced the number of people seeking these harmful objects and their willingness to pay higher prices for them, than by essentially just moving the supply curve to increase the equilibrium price.

of course that doesn’t actually make any literal sense in context, it’s just background music . But you know, I am finally on the road. I haven’t quite gotten very far just yet, as I write this, or dictate it anyway, I am leaving Richmond where, once again, someone I connected with for supplies along the way had questions about my story. This is a conundrum that I posted about on Facebook the other day: I am trying to learn to listen and seek the stories of others, yet, what actually happens is that people ask me question after question and I don’t get to stop talking. Of course there’s a skill deficit to that as well, and I am trying to learn how to stop talking and listen, how to stop telling my story and instead invite someone else’s story. Sometimes it’s hard to ask for the story, when it may not be a comfortable story. I find sometimes that I am scared to ask for someone’s story because I don’t want to hear the tragedy, I don’t want to feel inclined to try to solve their problems, or I just don’t want to feel bad for how much kinder life has been to me than to them. That is why I am on this particular journey, particularly to cope with the idea that I cannot fix the world, I cannot make life fair for the countless people to whom life is not fair in worse ways than how it is not fair to me.

Richmond is not really on the way, but this is not a trip about the most direct route in the first place. I’m trying to figure out my best way to camp and travel as things change, as my body is a little bit worse than it was on the last cross country trip two years ago , and I was pretty miserable that time as well. We don’t really talk much about being miserable while traveling, and that time I was directly punished for it; the woman I was visiting was very upset that I said negative things about the trip, as though The travel being unpleasant was somehow a judgment on her. But the simple fact was, I just wasn’t comfortable. And I’m not now.

So, I’ve been working on upgrading my bougie SUV camping routine, and I am very much on the fence about quite possibly upgrading to an all out camper once again. I invested in a custom mattress of the largest size that I can fit in the Volvo while still having any space at all for gear, and while I have gotten out of the habit of traveling with a cooler at all, this lime situation has me needing to keep medication cold, and so I went looking on Facebook for a good quality car fridge, which led me to Richmond. Of course, by the time I got to Richmond, the guy with the fridge for sale had stopped responding, so I went back on marketplace and found one in Asheville that is actually an even better deal, and while I was in Richmond I found somebody selling some AirTags that I need for the security of all of this gear. And then I met that person, a couple actually, and they asked questions about my story, and I guess I just kind of started talking, and then I walked away, and then they walked back up to me and we started talking again, and I guess I told them bits of my story and answered their questions for around half an hour, and I still kind of regret that I didn’t ask more questions about them and their story. I think right now I’m broken on empathy, I’m just not succeeding at properly caring more about others than myself, and I think that is really why I need this particular trip.

I’m thinking about books, and themes from different stories I have read over the years. The one I want to read again right now, but it’s not on Audible, it’s Robert Pirsig’s Zen and the Art of Motorcycle Maintenance. I feel like that really is the trip that I am on right now, chasing Phaedrus. I also feel a little bit like Thoreau in the version he tells of his Walden pond experience, although I don’t believe him and never did. Thoreau wanted to tell a story about self-reliance, and failed at it; in fact, I think he was the first archetype of the clueless self-help writer. Here’s the story of Thoreau: Henry was a privileged young man who was bored in life, and I think that he felt for some reason but he just couldn’t cut it in competitive society, and so he decided to go and run away and do things on his own. And so he tells the story about how he went into the woods and basically built this whole little country estate for himself using only the labor of his hands and blah blah blah. The truth is, he went camping on his family’s property. He was not poor, he was not starting with nothing, he pretended to start with nothing by imagining the things that he already had to be free and available to everyone, which frankly is exactly the mistake that every self-help writer makes. it is the fundamental problem of privilege.

I think that this entry has to be kind of a table of contents, and I think that I need to spell out what it is that I am learning about and thinking about and writing about. Make no mistake, this trip is a midlife crisis. It really is a crisis. I should know by now who I am and what I’m doing and why, but I just feel like it’s not working. I’ve done all of the things that you’re supposed to do, but not really, not at all. I haven’t compromised, I haven’t settled down, I truly have not learned to love and I absolutely have not learned anywhere close to how to receive love. If I am honest with myself in a way that I seldom openly am, the truth of the matter is that my life has been governed by something resembling a hero complex, what the young people are now calling “protagonist syndrome”. Now, I think their criticism goes over the top. True, it is kind of all about me, but it’s still about what I can do for others. It’s about trying to solve all of the problems of the world, and settling for spending my entire life solving problems of individuals, problems that are depressing as hell because my solution is not a complete solution. What I do is I help people who are broke because they are broken, and because I cannot help them not be broken I try to help them be a little bit less broke. And it’s not working. I tell myself the starfish story and how it’s important to make a difference in each individual life that I can regardless of how many other people are still suffering, but it doesn’t work. My dominant emotion tends to become that of Schindler at the end of Schindler‘s List, lamenting that he couldn’t do more. By the way, it’s not like I’m great; I’m lazy as hell, I barely work any hours, I rely on other people to get everything done for me basically. But you know, I make the hard decisions, I give the advice, I know what to do. But I am burnt out.

My father always told me that he didn’t know anything about practicing law or running a business or any of the weird things that I do, but what he did know was that what I was doing was not working, not in the way that I needed it to, and he said that the smart money move was for me to find something else to do, and he was right. So you know, that, but it’s not so easy to just quit so along the way I might as well start by simply taking a little break, clear my head a little bit, get back into a literary mindset.

I tried to take a day off, but it didn’t work. I hired a replacement and told my staff that I was on leave, I told the government I was on leave, and it was not enough. Ultimately, it has been a process over time to gradually pull back, as I delegate more, and I finally got the government to honor a short moratorium on my hearings altogether. For six weeks, which should be enough for me to have one proper day in the eye of the storm – three weeks after the last hearing to stop worrying about it, and then a few hours before I start worrying about the next one three weeks later. I have at least three weeks of driving before I get to the Arctic, about as much on the way home, and kind of an open ended question in the middle. It might honestly depend on when I run out of money. After that, I come back to life, I recommit, I find the next mission and I truly enter middle age.

I almost forgot the day but a news story reminded me – the one year anniversary of war beginning in Ukraine, which happened actually at around the same time. In fact my last message to her – after the fact – was about heading home because of the war.

Megan was a COVID boater, one of many who started out in 2020 when outdoors was the only way to socialize in person. Her entire career in the sport was less than two years, but of course she came across as much more experienced than that when I met her in spring 2021. She had charged hard into the sport, learned and classed up quickly, dedicated the time and effort to doing it right. She brought this level of enthusiasm that a lot of us only aspired to, and I think quickly became a low level role model for it.

Megan’s death impacted me very deeply for a few reasons. She and I weren’t super close friends, by normal metrics. We had only met in person a few times, though we interacted a lot online. But she was part of this particularly devoted subset of the community that made a point of putting whitewater kayaking at the center of our lives. When she died, on a hazard we all knew about on an otherwise unremarkable low class run, it hit me deep on a “she was us” level. Each and every kayaker who heard the story saw how it could have been any one of us. Megan wasn’t the most experienced, no, but we all related to her. We had all made similar decisions at some point. “Watch out for that wood in that rapid” was a warning all of us had seen before, and going for it anyway was a choice almost all of us had made at least once. And when we heard the story I think each of us experienced the story in our minds firsthand. We all visualized it happening to us, and we all viscerally knew how real it was.

Megan was a good person, and a good member of our community, our tribe. She was not reckless but smart and respectful of the water and of the idea of a smart and safe progression through the sport. She didn’t really do anything wrong. Yes, critics could armchair quarterback how maybe she underestimated the hazard or overestimated her skill, or how the whole crew got in over their heads without realizing it. For me, the “what ifs” included that I was a qualified boater, someone with good SWR knowledge, and I had chosen not to be there for my own reasons. I was forced to wonder what could’ve been different if I’d been there. If her line would’ve been just a bit different if I’d been in the crew and nothing would’ve happened at all, or if another rescuer might’ve made the difference to save her after it did go wrong. I had bailed not because I thought the run was too dangerous, just not worth the hassle. I didn’t feel like a class 2 run that would involve a lot of little portages would be worth the hassle of having to find daycare for my dog and delay some work tasks. It wasn’t that I felt the run was deadly, it was that I thought it was inconvenient. And that kind of rocked my mental world a little.

My thinking about the sport has shifted in a few small ways and I’m not sure they are all for the better. Mentally, my focus solidified on rescue, instruction, and safety. I had been in the process of reassessing for a while, and after my own series of near misses culminating with an ambulance ride five years ago I was already dialing back and losing interest in the thrill seeking aspect of the sport. Instead I was struggling internally with whether to keep going at all, even as, on that trip, I was house hunting to more deeply commit my life to the paddling community. For me it had been kind of a Hail Mary, committing more deeply to account for my waning faith, like how some people start going to church more often as they start to lose certainty in their beliefs. And Megan’s death cemented a path for me.

It hit me hard and took a few days to really process. My first move was to get back out, just on class 2 at first. I wanted to practice safety drills and ropes but instead just took a mellow day to ponder the river. The day after that I went out on Kitzmiller for a personal first descent, and chose to walk the biggest rapid, being very mindful of every choice as I did. I went back home and immediately started looking for more training. I re-took the same SWR class I’d taken before, and noticed along the way that I enjoyed participating in the instruction side of it. The instructor agreed that I should pursue more of that. I went looking for a river kayaking instructor course, though work conflicts prevented me from making one work until the fall.

When the festival season started in April, I found myself avoiding them. I wasn’t sure why but I think I just felt overwhelmed. When Cheat Fest came I drove down to it, then changed my mind and took a random road trip instead, paddling a class 1 creek in Arkansas instead, and then I flew out west to take a Wilderness First Responder class.

Now, a year later, I’ve taken the classes to be a little more “certified” for safety and instruction, though not at the high level I might prefer. I’ve come to realize that the place I want to be in this sport is with the Megan Thompson’s of the sport – the enthusiastic beginners who could use a mentor and someone to set safety. I’m never going to run elite class 5 like the Stikine and I am fine with that. My goalpost has been moved to simply finding my place in the community in class 3 and 2 helping people safely learn and grow and experience this joy for themselves. Kayaking is ultimately about finding your place and learning to cooperate with natural forces beyond our control. The river is bigger and more powerful than any of us, and our way to enjoy it necessarily entails understanding that we are only floating through, driven by a current itself driven by forces bigger and more powerful than ourselves. To kayak down a river is to partake of fundamental forces of nature, to ride along in the cycle of water from ocean to mountaintop and back again, driven by the sun and the gravity of the earth and the moon. These are forces we need not try to control, but can nonetheless harness and ride to experience something most people never do. To ride a rapid through turbulent water, using the current and your skill to navigate around deadly rocks and holes, is to experience nature in a powerful way that is wholly different from just looking at it. This is a beautiful and priceless thing that we engage in, something worth sharing. Is it worth dying for? Maybe not. But among the ways to meet mortality, it’s not the worst. It’s not without purpose or beauty. Her life was not wasted, it was savored.

Megan will now forever more be a part of the lives of those who knew her, and her death itself will always be a part of how we interact with this sport that connects us to each other and the world. Let us remember and celebrate.

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 loved the design of the new iPhone X when it came out in 2017, but after trying one out for a week in early 2018 I decided to hold off for the next one.  My iPhone 7 was perfectly adequate at the time.  Then Apple introduced the iPhone Xs with a lot of subtle upgrades from the X including a new 512 gigabyte storage option, so I pulled the trigger on launch day.  I’ve now been actively using the iPhone Xs for almost four months and think I’m prepared to offer a brief review of it.

It’s really great.

Here’s what’s new or better coming from my old iPhone 7:

• Better cameras on front and back with Portrait Mode, zoom, and 4k video
• New “full-face” OLED screen
• Face ID
• Slightly larger
• Upgraded internals
• Louder speakers
• Better battery life
• Wireless charging

And a bunch of more subtle stuff.  iOS 12 adds a lot of new features as well but you don’t need a new iPhone for that, it works on all iPhones back to the 5S.

A lot of people hesitate to try out the new phones because of, basically, the home button.  They like the comfortable and familiar nature of it, the intuitive approach, and the Touch ID sensor.  Let me say that it didn’t take long at all for me to not miss the home button at all.  First off, Touch ID doesn’t hold a candle to Face ID, at least for me personally.  With my paper-thin skin, I was never able to get consistent unlocking from the fingerprint sensor, so most of the time Touch ID just meant having to enter a passcode.  Face ID means I have to look at the phone and swipe to unlock, and it works with wet hands, gloves, etc.  Sunglasses don’t throw it off.  Hats and helmets don’t either.  In fact, I can even be bundled up for winter kayaking with my Buff neck warmer and my half-cut helmet and it still works, although a full-face helmet obviously throws it off.  It works in the dark.  Bed can be tough if my face is half-buried in a pillow, but if I turn my head so my face is exposed it’s fine even sideways.  In short, I rarely have an issue unlocking with Face ID, whereas Touch ID was always hit or miss.

The gesture approach to switching apps is also an improvement.  With the old home button, you returned to the home screen or unlocked with a single press of the button, and used a double press to activate the app switcher.  With the new system, you return home or unlock with a fast swipe from the bottom, and access the app switcher by swiping up about an inch.  Now you can also switch apps just by sliding your finger along the bottom of the screen, which I find myself doing all the time.  It’s basically alt-tab for an iPhone.  Brilliant.  I love it.

Now, the other function of the home button was Siri, which has now moved oddly enough to the power button.  That means the new gesture for Siri was the old gesture for powering off the phone, and powering off the phone now takes a chord of two buttons.  But I got used to it quick and I think I even prefer it now.  Siri is her same old half-reliable self- sadly Apple still has a lot of work to do there.  But activating it is no problem.

The home key and Touch ID are the only things you lose going from an iPhone 7 or 8 to the iPhone X or Xs, or the new Xr.  Everything else is pure upgrade.  The screen!  Big and beautiful.  Now, “the notch” has a lot of critics, and here’s how I look at it: I don’t think of it as a notch taking away from the screen, I look at it as “ears” adding to it.  Think about it – on an iPhone 8 (and every previous iPhone), the screen cuts off below the earpiece and goes straight across, with the status par taking up about the top 1/8 inch of screen.  But with the iPhone X and up, you get two little bits of extra screen next to the earpiece and front camera cluster, and Apple has moved the status bar stuff up to those new spaces that used to be just plain glass.  More screen!  Not just the more screen up top, but also reclaiming the space that used to be status bar.  And the bottom is bigger too, with a whole extra vertical inch of screen between the two reclaimed areas.  That’s awesome!  And the screen itself is stellar – higher resolution than the 8 and 7 (although less than the + phones – get the Max for that) and because it’s an OLED, the blacks are totally black.

The display also has Apple’s True Tone color management, which doesn’t seem like a big deal until you compare it against a phone that doesn’t have it, like the Google Pixel.  I find it impossible to describe but basically the colors just look better – it looks “right” and next to it everything else looks wrong.  Killer display.

So next I could talk about the cameras, and they’re killer.  Not just the back camera, which is outstanding, but the front camera, which is the best selfie cam I’ve ever used (although bested by the Pixel in one way – more on that below).

I could post more photos, but you can just check my instagram, @whitewaterlawyer, for more.

So photos are great.  What else is great?  Sound quality for playing music and other audio.  Just great, not really much to say.  The weight and feel of the phone in the hand, although in full candor I use it with a Mous case and not bare.  The raw power of the CPU/GPU combo is great, although admittedly it’s just plain overkill – it’s more than twice as fast as the iPhone 7 which already ran all my apps very well.

There’s really only two things that I don’t like about my iPhone Xs, and both are inherent to all iPhones.  The first is the way incoming calls are handled.  Just flat-out awful.  When the phone rings, the call dialogue fills the screen and can’t be dismissed without either answering the call or sending it to voicemail.  If you don’t want to talk and don’t want to send a “you’re not important to me” message, you have to wait it out.  Not nice.

My other complaint is peculiar to my personal use case: my phone is buggy as hell, which I’ve figured out is due to a host of bugs inherited through my backup. I’ve had iPhones since an 8gb 3G in 2008, and every time I’ve gotten a new one, I’ve set it up by restoring all data from a backup of my previous one.  I do this to preserve the data in the 100+ apps I use, along with things like my accumulated text messages and photos.  But it turns out that over the course of many repeated backup and restore operations, the backup itself picks up little glitches, and because you can’t selectively restore, in some cases setting up an iPhone from a backup can result in weird behavior.  None of it is severe, but I’ve got weird glitches like options missing from my settings menus and search not always working right.  I haven’t yet decided these problems are worth the hassle of “setting up as a new iPhone” even though, at least, Apple has moved most non-app data into iCloud so I wouldn’t lose any texts, photos, or notes.  I’d just have to re-download and configure all of my apps one at a time, manually enter all of my email accounts, etc.  Not a fun project for a rainy day.

The Pixel 3

Because Who’s Ready will be launching first on Android, I found myself in need of an Android phone.  Now, picking out a new iPhone is pretty easy – you pick a size, storage capacity, and color, and that’s about it.  Picking an Android phone is a whole other matter.  Once you’ve settled on screen size and storage capacity, you might still have dozens of choices.  I wanted something similar in size to my iPhone and at least 32 gigabytes of storage, and needed something with the latest version of Android that I could keep up to date for a few years.  That sadly didn’t narrow it down too much so I just looked at what was on sale for Black Friday and read a bunch of reviews.  I almost bought Samsung’s S9 for $519 on the BF special on Amazon, but then I saw that Google was offering the Pixel 3 for basically half price on their Google Fi service – $200 off up front and a $200 service credit.  Fi works out cheaper than adding a line on Verizon as long as I don’t use too much data, so I pulled the trigger, even though I probably would’ve been fine with a cheaper Fi phone from Motorola or LG.

Some of this is about Android, and some of it is about the Pixel.  Because I’m new to Android, I’m not really sure which is which for some things.

First, a lot of the hardware is similar to my iPhone.  The dimensions of the phone are almost identical.  There’s no headphone jack.  The rear camera is single instead of dual, but the front camera is dual.  The screen is an OLED of about the same resolution but a little smaller since there are bezels on the top and bottom.

Some comparisons:

Camera – Both the front and rear cameras are on the Pixel great and while I personally think the iPhone cameras are better, a lot of reviewers feel the opposite.  I really like the dual front cameras, though – the Pixel adds a separate wide-angle selfie cam, which is noticeably wider than the iPhone and means it’s now possible to get great selfies with my dog which is really difficult with the iPhone.  The rear camera is single-lens so the portrait mode is not going to be as good as the iPhone.  I haven’t played with the portrait mode that much – I just don’t like the interface of the camera and found that when I had both phones handy, I usually reached for the iPhone.  But I did spend some time at the dog park shooting exclusively with the Pixel.  It takes decent action shots, but on the whole I was just not impressed.  It’s definitely not bad.  And maybe it’s the screen more than the camera.  But the images just don’t pop off the screen like they do on the iPhone.  Ultimately I see this category as a tie.

Screen – The Pixel has an OLED screen just like the iPhone, so it’s also got a high resolution and great true blacks.  Plus, unlike the iPhone, Android supports an “always on” display, so a portion of the screen is lit up with time and date and notification icons even when the phone is locked (sidebar, I don’t like the notification icons, more on that below).  But the screen lacks an equivalent to Apple’s True Tone, which makes it noticeably dull in colors in various settings when held next to the iPhone.  It usually looks a little more “blue” than the iPhone and is harsher on the eyes.

Interface – This is more about Android than the Pixel specifically, but I think it’s a big piece that has to be considered when choosing a phone.  The interface in iOS is just plain beautiful, and it’s impossible to fully appreciate the beauty and elegance of iOS without spending some time on Android.  Everything about it is polished and smooth.  I give particular credit to the screen fonts.  Text on the iPhone is crisp and soft in just the right places, with smooth lettering and perfect kerning.  Even fine print is clear and legible.  Not so on the Pixel.  Many have pointed out that Android supports custom fonts, but I shouldn’t have to customize a phone to get something easy to read.  The default system font is just harsh on the eyes if you’re looking at the phone for more than a few minutes.  This applies to everything you do on the phone – apps like Facebook and Instagram, every Reddit app, even just texting.  The font is downright jagged compared to the default text on an iPhone.  And you can’t customize it without downloading third-party software to modify the Pixel, which I’m just not all about.

Some things about Android are hands down better than the iPhone, but not many that I’ve noticed.  People say that notifications in general are better but I’m not sure I agree; the icon routine just results in a cluttered status bar and makes clearing notifications a mandatory chore instead of optional like on the iPhone.  But incoming notifications are unobtrusive, and here’s the killer – that even applies to phone calls.  When an Android phone rings, you can answer or send to voicemail like an iPhone, but you can also finish your text message or whatever else you were doing before dealing with the call, or you can look up some info about the contact in an app, or you can slide the notification away and let the call silently ring out.  That is excellent.

A lot of people love the customization that Android allows.  I do not.  I like being able to customize my devices, but I only care a little bit.  Give me a great home screen layout for sure.  But I shouldn’t have to spend time organizing my phone just to make it usable.  With the default launcher on the Pixel, you can’t just have all the icons you want on the main screen – you have to customize it, and you have to manually plant each icon on a screen.  They don’t automatically sort, they just sit wherever on the screen you happen to drop them.  You can add various “widgets” to the home screen, which is nice, but gimmicky.  I added the calendar, but it doesn’t work so well, partly because the built in apps often just suck.  I can’t figure out how to display multiple accounts in the calendar, for instance; in fact I’ve found the phone almost useless for email and calendar because of how user-friendly it isn’t.  I can’t figure out how to get it to default to an account other than the one associated with the Google Fi line, nor can you log out of that account.  I did eventually figure out how to add a second Google account but it wasn’t intuitive.  Very little about this interface is intuitive, at least to a seasoned Apple user.

Part of this customization is that while the phone comes with a baffling array of apps, many of which I don’t know the purpose of, it is lacking a few of the basics. There’s no voice memo recorder.  The notes app has a half-assed voice memo feature that’s supposed to suffice, but it’s “voice activated” which means it stops recording when you take a breath, and you have to look at the screen to use it.  Useless.  Apparently true Android users use Google Assistant to take voice notes.  I haven’t had much luck with Google Assistant – the phone has a gimmicky “squeeze to activate” feature where pressure sensors on the sides of the phone serve no function but to activate Assistant.  Why they had to use subtle pressure sensors instead of a good old fashioned button is a mystery to me.  But it just doesn’t work.  It’s impossible to activate it while the phone is being held in a dashboard mount, and half the time I try to use it, it starts to come up but then disappears before I can actually use it.  Ultimately, and ironically, it’s easier to use Google Assistant on an iPhone where there’s at least a screen icon for it.  I don’t like how this is implemented.

Speakers – the Pixel uses valuable front space for two large speaker grills instead of a bigger screen like the iPhone.  Yet in spite of that, the sound quality is crap.  Well, I don’t know, it’s probably better than a lot of phones.  But it’s not even close to the sound quality of the iPhone Xs.  It’s merely okay, which is again baffling considering how much showmanship they’ve put into the physical design of the speakers.  Maybe I’m missing something, but the same track on Spotify sounds tinny on the Pixel and great on the iPhone.

On the whole, the Pixel is a good quality phone with all the features you need, but in terms of polish and user interface it just doesn’t come close to the iPhone.

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.