The Second Try

It is amazing to me just how much better you can get at something on only your second attempt.

There are just so many “first-time” mistakes that are literally just that – things that you only do while learning the most basic elements of a task. As soon as you’ve experienced even one cycle of actions and results, your understanding is an order of magnitude greater. Compared to someone who’s never done something, the person who’s done it once is an expert.

Despite this, the fear of those initial mistakes makes people not attempt the action at all. Or discourages them after that first attempt. “I made so many errors,” they say, “I must be terrible at it, so once was enough.”

Quitting right before it gets good is silly! The first-time mistakes don’t last, and once they’re out of the way you can have such a blast. That wall is paper thin – go break through it!

Good & Narrow

I was speaking with someone yesterday about various impressive accomplishments one could achieve. He pointed out that many impressive accomplishments were no longer unique; even climbing Mt. Everest, while amazing, isn’t a win you could solely own.

Life offers you two solutions to this conundrum. One is to be the absolute best at some broad thing – climb Everest the fastest or something. Difficult in a world of so many people! Option Two is to narrow your focus. You might not be the only person to summit Everest, but maybe you could be the only one to do it blindfolded.

I’m not recommending that directly, of course. I’m just saying that one way to be the absolute best at something is to pick a niche.

Not only is it easier to be the best in a narrower field, but you’ll actually be more distinctive for it. The news doesn’t cover when people climb Everest any more. But it sure would if someone did it blindfolded.

Invisible Walls

Sometimes, there are huge things stopping us from moving forward, and we can’t see what they are. We think the way looks clear, and we’re confused when our forward momentum is halted – perhaps suddenly! Not only can the sudden stop be unpleasant because you thought you’d get to Point B and you didn’t, but in addition you might have even suffered some loss from the impact. Maybe you sank money into an investment and not only didn’t you get the return you wanted, you lost your stake. Maybe you thought things were going really well with the new person you’ve been seeing, and when it falls apart you’re not only left confused as to why, but you’ve also invested time and emotional effort that’s now lost.

There are some simple steps you can take that, while they can’t prevent this, can at least soften the blow. Don’t be too careless – if you charge ahead heedlessly, you can hit a wall you didn’t even know was there. Trust the opinions of a few others whose intelligence and insight you respect, and seek advice with some regularity. If you always go it alone, you only ever have one angle from which to view things, and maybe from another the wall wouldn’t have been quite so invisible. Don’t invest more than you’re willing to lose in any one endeavor; but remember, you can often bear greater losses than you think. You’ll earn back that money, and you have more emotional effort to give, and you’re not out of time yet.

And if, just if, you work in an office that has floor-to-ceiling glass paneling directly next to doorways, just… maybe watch where you’re going? Your face will hurt less.

Permission to Ask, Permission to Answer

I am extremely solutions-oriented. That can be both a strength and a weakness, and my goal is to make it less of the latter while retaining it as the former.

One of the “weakness” aspects of being solutions-oriented is you tend to view all problems as fundamentally “solvable” and thus approach them with that framework. Ask my wife how well that works out. Some situations are negative without necessarily having a solution, or perhaps the solution is just to support someone going through it.

I, on the other hand, have my sleeves permanently rolled up. I work. I’m not the “moral support” guy, I’m the fix-fix-fix guy. I’m aware of it, and so I’ve been trying for a few years now to get better at really actively listening and trying to judge when the other person or people need solutions or just need to bend an ear for a while. I’m proud to say I’ve actually been pretty successful, but I still have plenty of room for improvement.

I was talking to a truly brilliant co-worker of mine today, and she told me something that might seem obvious to people that aren’t me, but it was a radical departure from my standpoint. She said: “Don’t guess. Ask. Say, ‘I have some ideas for solutions that may work for you, but I want to make sure you need that first. Do you want to hear those or do you want to talk out your concerns a little more?’ No need to try to figure it out on your own.”

This is stellar advice! It’s a great communication tool even if, unlike me, you’re never wrong about whether or not someone wants solutions. Even if you can flawlessly figure that out for yourself, asking permission to offer solutions or ask more questions really helps the other person feel heard, understood, valid. It can help create a bridge between your intentions and their perception, which is always a good thing. And it can improve the quality of the solutions you offer!

This is such good advice for me that I’m legitimately excited for the next time I hear about someone else’s problem. I know that’s a weird thing to say, but hey – one problem at a time.


What tools do you use to understand yourself?

The study of the human mind is fascinating. One of the reasons is because it’s studied through so many different lenses – we look at the mind’s capabilities, what it will do in a business setting, how it impacts relationships, its health, its propensity to violence or addiction. People study broad trends and try to extract meaningful information about individuals from those averages.

What factors make someone a great leader? Prone to crime? A supportive spouse or awesome parent? Good at baseball? Terrible at appreciating art? A mathematical genius? An angry loner?

No one can know you as well as you know you, but there are two problems with considering yourself an expert on yourself:

  1. You’re the closest to the subject matter, sure, but that’s not always good. There’s a lot to be said for clinical detachment when it comes to honestly evaluating something.
  2. Just because you have the most intimate exposure to the subject matter, doesn’t mean you have the tools to evaluate what you should.

I can say “I know myself better than any psychiatrist!” but that’s obviously hubris. There are a million terms, trends, tools and techniques I’m completely ignorant about that would peel away layers of uncertainty.

So I look for tools I can use. I like personality tests, self-assessments, things like that. It might be dangerous to put too much stock in any one, but using many can give broad trends that smooth out the spikes. Anything to look “under the hood,” so to speak.

Just because you drive the car every day doesn’t mean you know how the engine works, but at the same time you do have information a mechanic can’t have; you know all the subtleties of exactly when the weird noise happens or under what conditions the gear slips. You know the symptoms better, even if you don’t possess the tools needed to diagnose the actual problem.

It’s worth seeking out those tools, but don’t ever forget that you’re driving. The best approach is a blended one – evaluate yourself as carefully and critically as you can, and seek outside tools and expertise when you reach the limit of your own evaluation. How else can you improve?


Where do you do your best work?

For as long as I’ve lived on my own, I’ve always maintained a dedicated office space of some kind. When I was young, my father ran a business out of the home and had converted one of the first-floor bedrooms into an office for his work, and to this day that room in that house is still his “office.” He’s long since retired, but he still has a room configured that way. It looks exactly the way you think it would look, being the home office of a man who spent his entire career working with audio/visual equipment and electronics.

Mine were always significantly neater (I’m far more of a minimalist than my father), but I also always kept a space like that. I didn’t have my own business like my dad did, but at many points in my career I did various freelance things, and even between them I’ve always liked having a specific space for writing and other projects.

When people make decisions about their careers, they’re often motivated by things other than (or in addition to) salary and job description. The “side perks” are often equally important, like commute time or office culture. One of these perks that is more and more desired and sought-after is the ability to work remotely at least some of the time. That was never high on my list of priorities – I didn’t have strong feelings either way about it. Despite this, I’ve found myself in roles where I work 99% remotely for the past half a decade.

Since I already had a home office (I always do), and didn’t really seek out remote work for that reason, I haven’t given a lot of thought to my work environment. I just worked where I was. But in those five years a lot has changed. My number of children tripled, and the amount of stuff they have has increased by a factor of approximately 100. The amount of noise they make has increased to a level incomprehensible by man.

So for these and other reasons, I’ve decided to try out a co-working space. I’m sitting here right now! I found a great little one less than ten minutes from my house, with a very reasonable price point and all the amenities I need for my work and other projects. In fact, I came here late last night and had some of the most productive few hours of work I’ve had in a while (it’s available 24/7, a huge selling point for me).

The additional benefit was not only high-productivity work hours, but when I got back home I just… didn’t work any more. A historically difficult thing for me. But I just didn’t unpack my laptop.

The problem you run into when you don’t make deliberate decisions about things is that those decisions get made anyway, they just get made in fuzzy default ways by the universe. So me just sort of sliding into “working from home” as my default without taking the time to really establish what that means, especially in the face of a growing family, meant that there were a lot of negatives. The lines between when I was working and when I wasn’t became less clear. I was both always working (bad for the home life) and always available for my family (bad for work productivity). So in many ways I got the worst of both worlds.

Now I’m aiming for a “best of both worlds” situation instead. A co-working space means I can put clear bright lines between my work time and my home time, but the fact that I still technically work remotely means I still have 100% flexibility to be available to either as I need. If one of the kids has a doctor’s appointment or something, I don’t need to be “in the office,” but it being otherwise available to me means I can be at work when I’m at work and home when I’m home.

December is going to be intense on both the work and the home fronts, so a little structure sounds wonderful. What environment do you craft for yourself to maximize your sanity?

New Month's Resolution – December 2019

November was a fast-paced month with many changes. I believe I accomplished my goal of “hitting the ground running” in my new role at work, which has been incredibly rewarding. I work on an absolutely amazing and supportive team, and it’s a great environment in which to do good work.

That being said, there were definitely a few setbacks overall, some of which were expected and some of which weren’t, and that’s making me re-evaluate my plan for the last 31 days of the year.

  1. I did get a lot of reading done, but the pattern changed significantly. Most of the time I don’t read one book at a time; when I had physical books there used to be a dozen with bookmarks in them on various end tables throughout my house at any given time. Thank goodness for my Kindle. So if I read 4 books in a month, it’s not because I read one per week. Rather, I’d read one for 30 minutes, another for an hour, 4 chapters of a different one, back to the second one for a few pages, etc. Because of this, I’ve come to notice certain patterns in my reading – the more books I have “open” at any given time, the more deeply (ironically!) I’m diving into a specific topic. If I only have a few, I’m reading casually, but many means I’m trying to absorb everything about a topic. That’s what this month has been like. Still, I’m scaling down my reading requirements for December, because I have so many projects on my plate – some days it was very hard to get 30 minutes to myself to read.
  2. The schedule I’d tried to set for myself with work isn’t going exactly according to plan. Without going into too much detail, I essentially now wear two different hats at my job – I still do my old job, but have also taken on the responsibilities of the new role. I tried to segment the two into different days of the week, but the two sets of responsibilities just don’t want to be organized that way, so I’m going to re-evaluate that. Dividing up the day into segmented hour blocks will probably work better than dividing up the week.
  3. The holidays! I never seem to remember just how disruptive they’ll be, but I lose lots of time during them. Maybe it’s because for the last several years, my growing family has meant that each year’s holiday season has actually been significantly more hectic than the prior year’s, so I’m caught off-guard each time. I don’t really have a good solution to this one, other than to remember that there are actually only like 4 working days in December, apparently.

So here are my resolutions for December:

  1. Finish the rough draft for my book. Extremely doable based on my pace, but I have to be aware of which days actually allow for writing.
  2. Wrap up all my other projects so that going into January I have a clean slate to take on more. That includes both personal projects and my current work assignment.
  3. Research a more intense work-out/exercise regimen for January. I like mine, but I’ve sort of plateaued on it, and I want to have something new to implement right away after this month.

This is a great month for resolutions. It’s too easy to put things off and say you’ll make them New Year’s Resolutions, but my first version of this post was me talking about why that’s bunk. If it’s worth doing, do it today.