Someone very dear to me just hit 60 days sober. I’m so incredibly proud of them, and I think those thoughts are worth sharing.

My life has been impacted negatively by substance abuse many, many times. I’m fortunate that I never personally fell into the trap of addiction – fortunate because I certainly lived a life that could have led there in my 20’s. But I’ve had people that I care about, very close to me, whose lives were worsened, shortened, or even ended because of this abuse. I’ve seen children heavily impacted by a parent’s abuse. I’ve seen families destroyed by it.

I don’t think of myself as a puritan. I don’t tell people that they should never drink, or stand on a street corner proselytizing about the evils of some substance or another.

But I do advocate for freedom. Almost everything I write about, think about, or care about in some way centers around the philosophy of making yourself more independent, more in control – more free. I try to point out shackles people didn’t even know they had and give advice on how to shed those chains.

We aren’t robots. We have a million influences on us that we didn’t choose. We have innate biases and bad habits and unhealthy emotions and societal constraints and all sorts of other things we have to fight against every day. So the last thing we need is something else to weigh us down, shackles we don ourselves, things that weaken us against the others.

No matter what flaws we have, it is always worth examining them and seeking, if not to overcome them, then to craft a life where they do the least amount of harm. Exert the least amount of control over us.

So if you drink, I won’t judge. But let me give you advice – go sober for a while. Just prove that you can. Take the extra time to test your theory that you’re the one in control. If you are, you’ll gain a month’s clarity and a few extra dollars and then you can do what you want. Or maybe, just maybe, you’ll find that you don’t want to don those shackles again. This could be anything, really – drinking. Drugs. Facebook. Video games. Porn. Whatever. Just give it a rest for a while. And with a clear head, see if you’d actually choose to go back.

And for you, who did that and has not gone back – I love you and I’m proud of you.

You, Inc.

Think of yourself like a business.

Businesses often make decisions fundamentally differently than individuals do, but you can gain a lot from thinking in a similar way.

Businesses have clients, not employers. The successful ones care deeply about those clients, but they recognize that they’re the core architects of their activity. Businesses aren’t groveling and begging, they’re advertising. That’s what you should be doing. Information about you should be plentiful, positive, and easy to find. Don’t hide.

Businesses invest in themselves for the long term. They keep immediate costs as low as possible, but successful businesses know when to spend money on things that will have a very positive long-term return on investment. Think about traditional higher ed – the standard argument in its favor is that while it’s ridiculously expensive, it pays off more in the long run. But there are things that are many orders of magnitude cheaper than a college education that will pay off way more. Just taking a writing course, learning a programming language, or attending a workshop can be far, far more beneficial. As a good rule of thumb, make sure you’re spending more on stuff like that each month than you are on luxuries you don’t need.

On that note – successful businesses tend to only buy things that (they at least have good reason to believe) will make them more money than they cost. Businesses don’t have consumption goods. You might buy a fancy house for the social status, but a business buys a fancy office because it believes it will attract more customers. Are you getting better job offers because of your sports car?

Of course, you’re a person and not a business. You have feelings and care about enjoying the pleasures of life. You should – why else live? But don’t buy those things first. First, buy things that will pay for the other things.

Want an example? Let’s say you want a fancy new car – like $500/month payments fancy. And let’s say you could even afford it. Still don’t. Instead, take that money and invest in something that will return at least $500/month – like a new online business, the equipment to do a side hustle, or even an investment in an existing organization that will pay that dividend. Heck, buy a lawn mower and enough posters and Yelp ads until you’re making an extra $500/month mowing lawns.

Then buy the fancy new car.

This is a dramatic change in thinking for most people. But it can produce dramatic results. If you run your life like a business, the biggest dividend will be freedom.

Some Assembly Required

I have a great admiration for the concept of the assembly line.

Inputs enter on one side, there’s a series of defined, meticulously-curated actions, and then an output emerges from the other end. It’s a thing of beauty.

You can think of a lot of the processes in your life as working like that, and then you can find it easier to make improvements. If you think of all outside stimuli as inputs – from unwelcome news to challenging assignments to interesting blog posts – you can create a series of tasks to do for each of them.

Where do you put things to keep track of them? How do you devote time to them? Who do you speak to about them? All of these questions are stops on the assembly line.

It might seem a little mechanical, but many of the tasks in your life are just that. You shouldn’t put everything on the assembly line; some things are sublime and deserve to be treated as a whole experience. But not everything – some things just need to be processed.

Keeping them separate leaves you more time for the good stuff.


If you take any major circumstance in your life, you can trace its history back to a point where a tiny change would have made it all different. It’s possible that tiny change might even be before you were born, but it’s still there. Somewhere out there is a man who stared at airplanes flying in the sky his whole childhood and then grew up to become a pilot; if his bedroom had been on the other side of the house he’d have seen the train yard instead and maybe become an engineer.

At some point, you met someone who changed your life. Maybe you’re very aware of it and maybe you have no idea, but it happened. Maybe your parents’ first meeting was quite the chance encounter, and one late bus could have meant you were never born.

We think of the history of our lives as resilient – as if the way it’s unfolded so far is the way it must always have unfolded. But the tiniest changes could have re-written the whole tapestry.

That applies to the future, too. Tiny changes can have incredible, far-reaching impacts if they occur early enough.

Sometimes we get a chance to do a small favor, and even though the effort is low, it’s equally easy to not do it. The reward seems minor, even inconsequential.

Do it anyway. Send that email, make that call, lend that dollar. We can’t possibly predict all the long-term consequences of all of our actions, but I’m willing to bet that if you make more of your actions good and kind and generous than not, that the long-term effects will trend that way too. It might be three generations before it happens, but someday someone will say that you’re the reason their life is good.


Deciding to take action can seem sudden. As a result, people will decide to take action… a long time from now. “I’m definitely going to take that painting course! Next summer.” Somehow, a million things happen between now and then and you don’t do it.

Saying “I’m going to take that painting class – tomorrow!” can seem impulsive. So we’re scared of it, and we buffer our decisions with too much extra time. The reality is that the suddenness only feels that way because you’re measuring the incorrect length of time. The time between when you finally decide to take action and when you take that action should be short – as short as possible. What makes it not sudden at all is when you realize that the time period being referred to is the gap between when you finally decide to take action and the very first time you wanted to.

That gap could be years.

If you take a long time to decide, so be it. That’s in the past. But once you decide, don’t fool yourself into thinking you can decide on behalf of some future version of you that might never come into existence. You can only control the Present Day You, and that’s the person that has to take the action you decided on.

Go forth, and wreak havoc.


I’ve been a bit of a slacker on my workout for the last week or so. But my oldest daughter really likes working out with me, so today she requested that as a daddy-daughter activity. It’s easier to put off your workout when it’s just for you. How can I say no to her?

You can generate a lot of good habits in your life by tying them to other things you want to do. I always invite my kids along with my chores. When my three-year-old says “I wanna help!” while I’m doing dishes or cooking dinner, I always find something for her to do, even if it’s just holding a can of peas or drying a spatula.

I encourage my kids to join in the things I have to do, so they’ll want to do those things. That in turn keeps me motivated to do them, like today. I got a really solid workout in because my daughter just wanted to spend the time. If I played video games with her that’s what she would want to do, so instead I try to tie as much of our activities together to positive things. Reading time, workout time, cleaning time, etc.

Connect the things you want to do with the things you have to do. It’ll help.

Keep Doing What Doesn’t Work

I often think about the usability of advice versus its “absolute value.”

For instance, let’s say I ask you “What’s the fastest way to get to San Francisco?” You could answer “fly the Lockheed SR-71 Blackbird” and technically be correct. You would also be wildly unhelpful, since there’s zero chance of me doing that. More practical but less “technically correct” advice would be to book a non-stop flight on a commercial airline.

In that example, it’s easy to see the difference between the “best” answer and the most helpful answer. It’s not always that easy, though. One of our big hangups is when we give advice that is both good in an absolute sense, and easy for us to follow personally, but that the person receiving the advice can’t utilize fully for some reason.

Here’s an example: you’ve lost a lot of weight and gotten healthy lately, and your friend asks you for advice. You tell them that you joined a gym with a pool because swimming is super good exercise, and you went swimming every day. This is good advice, and it clearly worked for you. Your friend, however, is deathly afraid of water.

The advice is still good in the “absolute value” sense. But your friend can’t use it. Now, you can try to force the issue by trying to convince your friend that a fear of water is unfounded, that logically they’re in no danger in an indoor pool in a gym with a lifeguard on duty, and that their phobia is standing in the way of their progress. And you’d be wasting your breath.

Instead, just give them the best advice that’s actually useful for them. That might be #4 on the actual list, but if it’s the one they can use, it’s the best one.

A really common version of this that I encounter follows this pattern. Let’s say Bob comes to me for advice. Bob says, “I’m doing X, and I’ve been doing it a hundred times a week for 6 months, and it isn’t working. Help me out here.”

I say: “No problem. Stop doing X; it isn’t working. Instead, do Y and you’ll get good results.”

And then Bob says back: “But that’s really strange! All the standard wisdom says do X!”

I used to get really frustrated. I used to waste a lot of breath trying to explain to people the faulty logic of telling me that X had been failing again and again but then defending it as a good option because the “conventional wisdom” said to do it. I used to try to actually get into all the deeper reasons behind why X might have been a good idea once before, but times have changed, blah blah blah.

That didn’t help me, it didn’t help Bob.

Here’s what I started saying that helped a lot: “Okay, then keep doing X too. Just also do Y. That way you get the best of both worlds.”

In this case “keep doing the thing that isn’t working” actually became good advice, because it was the only thing that made them also do the thing that would work. The sunk cost fallacy and “conventional wisdom” bias are both huge influences on people’s ability to think clearly, so instead of fighting it, just work around it. As long as the thing that isn’t working isn’t directly countering the thing that will work, doing both is fine. They’ll gradually abandon X when they see Y is working all on their own.

Give the best advice someone can use, and help the person they are.