Back in 2022, I wrote a post called 20 Things I've Learned as a Systems (Over) Thinker—”over” was in parentheses—and I've since received so much feedback about that post. I recently re-shared it on LinkedIn and it obviously strikes a chord. And so I thought that for this episode, I would just quickly go through that list, provide a little bit of extra color, and hopefully clarify some things.

I'll be back to interviewing guests in the next episode, but I'd just like to experiment with this format and be curious what you think.

Here is the list for reference:

* Take care of yourself. Your brain is working overtime—all the time. Practice “radical” recovery.

* You may spend a lot longer thinking about things than most people. Pace your delivery.

* If you go deep first, and then simplify…keep in mind that you don’t need to show all of your work.

* Your default description of (almost) any problem will be too threatening/overwhelming.

* Do your deepest thinking with co-conspirators (not the people you’re trying to influence).

* Informal influence is often not formally recognized. Prepare mentally for this.

* The people you’re trying to influence spend 98% of their day overwhelmed by business as usual.

* Remember to also do the job you were hired to do (if you don’t you’ll be easier to discount).

* Seek “quick wins”, but know that most meaningful things will take a while.

* Some things take ages to materialize. It is discontinuous, not continuous.

* Make sure to celebrate your wins. They will be few and far between, so savor the moment.

* The people who support you in private may not be able to support you in public. Accept that.

* Hack existing power structures—it’s much easier than trying to change them.

* Consider becoming a formal leader. It’s harder in many ways, but you’ll have more leverage. What’s stopping you?

* In lieu of being a formal leader, make sure to partner with people who actually “own” the area of change.

* Watch out for imposing your worldview on people. Have you asked about what people care about?.

* You’ll need a support network. And not just a venting network. Real support.

* “Know when to fold ‘em”. Listen to Kenny Rogers The Gambler. Leave on your own terms.

* Don’t confuse being able to sense/see system dynamics, with being about to “control” them. You can’t.

* Grapple with your demons, and make sure not to wrap up too much of your identity in change

TRANSCRIPT

[00:33 ] Take care of yourself. Your brain is working overtime all the time. Practice radical recovery.

I would basically find myself at the end of a multi day effort . I wasn't aware of just how tired I was and just how fried I was. How muddled my thoughts were. And I think part of the reason for that is if you enjoy going deep on things, and if you enjoy picking things apart, and if you enjoy analyzing things, you sometimes don't notice just how much effort that takes and how much bandwidth that takes.

And so it was important for me to try to set aside time to just completely disconnect, not jump into another thinking topic, not jump into something else that had high cognitive load, but try to strive for zero cognitive load. One of my favorite things is just watching cartoons with my son. Because I completely disconnect.

[01:29 ] You may spend a lot longer thinking about things and most people. Pace your delivery.

So if you've spent many hours going deep on something, you can't walk into a meeting and expect someone in three minutes to follow your thought process. It's just not going to work. You're going to have to pace your delivery to bring someone along on that journey.

And if you're good at analyzing things. If you're good at this type of systems thinking or overthinking, you can go so far in a couple hours. You can focus and go so deep. And there's no way you're going to be able to deliver all that information to someone. You have to get really really, really high level and rewind. And be super deliberate about how you deliver that information.

[02:17 ] If you go deep first and then simplify, keep in mind that you don't need to show all of your work.

So what I used to notice is that I would keep all of my work and the three bullets. And I would start with the three bullets and say, well, this is where I arrived at. And I felt like it was important because for some reason it's important to me to show how I got there.

So instead of just saying, here's the solution, do this. I would say let's try to unpack all the layers of this particular problem and how I arrived at this particular solution.

It turns out that that can greatly diminish the impact of the destination that you arrived at. And honestly it can open you up to all sorts of debate. It can open you up to all sorts of questions. And somehow it makes you seem less confident about what you're doing.

Now, not that I agree with any of that and I wish it could be different, but realistically you don't need to drag people through the whole mess.

[03:17 ] Your default description of almost any problem will be too threatening or overwhelming.

This is something I've had to come to grips with. The default detail that I want to go into on something is just going to seem threatening.

And the more I try to sugarcoat it the more weird it sounds also. So this is a tough one to come to grips with, but the important point here is understanding that the depth that you go into on something and the thoughtfulness you try to put into something and the different perspectives you try to discuss can be very threatening.

In fact, I used to think that describing something as a systemic issue was in fact less threatening. Because in some ways, by describing it that way you understood that well, there's a lot of contributing factors. There's not one person to blame here. There's a lot going on. And we're going to be able to figure this out. Or so I thought.

Realistically, when people hear systemic issue, when you don't point to one specific person or one specific situation and say, that's, what's messed up, it's actually highly threatening. So keep that in mind.

[04:24 ] Do your deepest thinking with co-conspirators not the people you're trying to influence.

In an ideal world, at least for me, everything would be co-designed. Everything would be a result of deeply exploring things with everyone involved. And you would arrive at the solutions that everyone believed in.

That's not the case, in many situations.

You might have other people that you're close with who are willing to go on this deeper journey to understand what the problem is. And I call those co-conspirators in this case. These are fellow system overthinkers who don't mind the ambiguity, who don't mind exploring different paths and then rewinding. Who don't mind dredging up these particular issues and looking at them from different angles.

Realistically, if you're trying to influence someone, it might be a good idea to bring them on that journey. But it might actually completely defeat your cause to bring them on that journey. So in that particular situation, if the person you're trying to influence isn't necessarily on that wavelength, and doesn't want to take that journey with you, you don't bring them along that particular journey. And you might be more influential in the long run.

[05:36 ] Informal influence is often not formally recognized. Prepare mentally for this.

If you're expecting the same kind of recognition that goes to people with formal influence and formal authority, you'll probably go off track. In fact, I think if you're seeking that, if you're seeking that recognition, if you're seeking to be in the limelight, if you're seeking that kind of gratitude publicly, you will be sorely disappointed. And it will probably send you off track.

So you have to prepare mentally for the fact that many of the things you do will influence informally in ways that people might not be able to immediately recognize. You might have a small number of people come up to you and say, you know, I really liked what you did there. Thank you so much. I really appreciate it. But it's not going to be this groundswell thing. You're not going to win the president's club trip to Hawaii or something with your sales team. And as long as you prepare mentally for that, I think you can be in good shape.

[06:39 ] The people you're trying to influence spend 98% of their day overwhelmed by businesses usual.

If you're trying to influence senior leaders you need to understand that they are really busy. This seems to be such common sense. But if you imagine that they're going to have any amount of time to go deep or as deep as you've been going on something, and appreciate all the nuances-- if you're expecting that-- you're going to be disappointed.

So you need to imagine that you are delivering the message to people who are overwhelmed. Who are under incredibly high cognitive load. Who are not necessarily in the right frame of mind to explore some kind of systemic issue.

You have to be prepared for that. Remember, you've set aside a couple hours to go deep on something. You've had all this time to do this focused work on something. This person is getting bombarded by every single person in the company. Back and forth.