On Positivity

2026.01.25

CXXXVI

[Positivity is Hard; Everyone Suffers; What is a Great Thing?; Glass Half Full; Glass Has a Hole in the Bottom; One Gratitude a Day]

Thesis: You can safely overcome the fear that positivity will hold you back by being grateful for one thing a day.

[Positivity is Hard]

It's really hard to think positively all of the time. In my experience, this is particularly true for high agency, high drive people who are trying to do some “Great Thing.”

Last week, I got dinner with someone who bootstrapped & sold his company for 9 figures, and he was saying that he even after his exit, he caught himself trying to do more:

This isn’t rare, either. I don't know if I've ever met an exited founder who is "done" after they've exited. They’re still restless and want to do “more.”

Even from high agency people who aren't starting and selling companies, I hear very often about a voice in the back of their head saying they're not doing enough, they need to do “more.” And, there’s this fear that if they let go of that voice, then they will fail to do the Great Thing they’re trying to do.

Based on my content, I would guess that a lot of my readers have this restlessness and anxiety, just like I do. Well, I'd be absolutely lying if I told you that I knew how to deal with it. I certainly don't.

But, I have some observations from living in circles full of this kind of restless, high agency person for the last 6 years of my life, and from being fortunate enough to meet many such people who have "won" the game, so to speak.

The most important thing that I think we could all use reminding of is that sometimes being grateful for challenges won’t jeopardize our chances of success.

[Everyone Suffers]

Suffering is part of life. Everyone suffers.

So, I think it's a bit of a delusion to say that suffering is a necessary condition for building something great--for the time being, suffering is a given if you live on the Earth as a human. We could also say that suffering, by the same logic, is a necessary condition for drinking coffee or tea.

Still, there is definitely something different in the relationship high achievers tend to have with discomfort.

Achieving Great Things tends to take a certain level of accepting uncertainty & long hours & delayed gratification & focus, all of which are not very "easy" to do. It's Type 2 fun, as they say.

I don't think that the person who pursues these things aggressively is "categorically different" than a person who does not, but the person who pursues these things definitely has to stay in uncomfortable situations longer than would be necessary if they were comfortable with a mean outcome.

In my own life, I used to be super uncomfortable getting on sales calls. Then, after forcing myself on hundreds or thousands of them, I eventually got comfortable. If you can imagine willingly doing hundreds of hours of something uncomfortable to achieve your goal, then you really do know what I’m talking about.

And now, I do other things I’m uncomfortable with: raise prices, get more aggressive on sales calls, speak with more confidence, automate systems.

If I want to achieve my current goal, I will have to keep doing things I’m not exactly comfortable with.

I think the same is the case for anyone pursuing a big, interesting goals.

[What is a Great Thing?]

I've been vague about what a Great Thing is. That’s a problem, because I do think that picking a Great Thing, or some ambitious goal, is a really good first step to curb some undue anxiety.

Anecdotally, the high achievers who have some goal to work towards seem less anxious than the ones who don’t.

In other words, I do think a lot of anxiety can from not knowing what you actually want or aggressively pursuing something that you don’t actually want.

Last week, I spoke with a founder friends who raised $20M. She said something to me that I totally agreed with:

I whole heartedly agree with her stance, both economically and emotionally.

Economically, she's already raised $20M over 3 rounds & has 35 employees. That means she owns less of her company than I do. A $20M exit for me would mean I don’t ever have to work again, but for her it would probably not mean that.

More importantly, emotionally, she has decided she is to "IPO or bust." Selling for $20M is not an IPO, so it is, by the definition of her goal, a defacto bust.

On the other hand, I’m basically trying to earn myself a trust fund by building the RenTech of sales, either through revenue taken as profit over a number of years or via exit price. Then, I will build other things I am curious about.

My goal is very, very different than hers.

If we had our conversation without that context in mind, the conversation would basically be incoherent: if I thought she had my goal, and she thought I had her goal, we would both think the other was crazy!

For my desired outcome, it would be foolish to hire anyone at my exact stage, let alone 35 people. For her desired outcome, not having 35 employees would basically be suicide.

However, by both knowing what we are actually after, we can have a very sane and level headed conversation that is not anxiety inducing for either of us. We know that most comparisons we could do would be pretty meaningless or misleading.

On the other hand, if either of us spoke to someone who did not know what they wanted, that person might be tempted to just adopt one of our goals and compare themselves to it. Than can create a lot of anxiety on it’s own.

Of course I’m closer to MY goal than you are to MY goal! I’ve been working at MY goal for a while now.

But, there’s a really good chance you’re closer to YOUR goal than I am to YOUR goal. You won’t be able to see that if you don’t know what YOUR goal is, and you’ll just increase your own anxiety by judging yourself by my goal. Maybe you want to publish a bestselling novel or be a news anchor for a major station or start a non profit to bring potable water to Africa—judging yourself against someone bootstrapping a B2B SaaS is an outlandish thing to do.

Knowing your goal will help you move faster, make more clear decisions, and reduce anxiety. It doesn’t have to be the goal for the rest of your life—just a clear direction to move toward. Even if it shifts later, that’s okay.

(If you don’t know your goal, here is a post I wrote on doing something you’re passionate about that could be helpful)

[Glass Half Full]

Okay, so we're an anxious, high achieving person. We a) know our goal, and b) we're hellbent on achieving it. But, we're still anxious.

I see this all the time in myself and others.

Anxiety can be helpful. It can be a good driver and fuel to keep going. And among the crowd I've spoken of, there is this unspoken fear that if you lose that anxiety, you'll stop moving forward and fail.

I’d be lying if I said I didn’t have this fear myself. Is there a solution? I don’t know!

Regardless, something you can do that I really don’t believe will jeopardize your progress is to think with the glass half full at least once a day. In my experience, this can give you a positive boost that makes you actually move faster.

Whenever you're faced with a challenge or a task, you get to decide how you can perceive it.

Some business examples:

• "I have to push this bug fix" -> "I get to make the platform more reliable."

• "I have to deal with a customer support request" -> "My customers care enough to submit support requests."

• "I have to take 10 back to back sales calls" -> "I have tons of chances to grow my business."

You GET to overcome the challenges to achieve your goal. That’s a very, very fortunate position to be in.

I'm grateful that my co founder, Jack, is very good at this. He’s much better at it than I am & seeing him do it reminds me to do it.

It sounds simple enough... so why does it warrant a blog post? Because it's really, really easy to forget. Especially when some challenges genuinely are a waste of time and need to be removed.

[Glass Has a Hole in the Bottom]

You can only optimize for one thing, and we've already established that the number one priority is NOT having a great mood all the time. The number one priority is achieving the great thing, which requires sacrifice, and it requires action, even when we don’t feel like it.

And, a lot of the times, being hyper critical really helps.

If, for an example, you have to do some low complexity repetitive task for every user you onboard, it would be dangerous to just be optimistic about doing that. "I get to support my users, yay!"

Really, that's exactly the kind of task that you very likely should remove or automate. Training yourself to get dopamine whenever you have to do a task that should be eliminated or automated will not help you achieve your goal. Look at a task and saying, “This sucks, why am I doing it, how can I make it easier?”, on the other hand, can bring you closer to the goal.

And, it’s important to be pessimistic enough to stay vigilant against real risks to your business. This feels a lot less like “Glass Half Full” and more like worrying that your glass could sprout a hole in the bottom of it at any given time.*

_{*Jim Collins would call this Productive Paranoia}

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[One Gratitude a Day]

So what the hell is the point of this post?

Be positive but not too positive? The Glass is Half Full until it's not?

What I'm saying is this:

Truly, not every single thing is a threat. Somethings really are beautiful opportunities.

If you don't see that, maybe force yourself to reframe one challenge as a positive thing per day.

It doesn't mean that you don't address the challenge, it just means you approach it with a positive attitude and as an opportunity to grow closer to your goal.

I promise that if you "fail," it's not because you were grateful for at least one thing a day.

Live Deeply,